feat(coderd/x/chatd/chatdebug): add types, context, and model normalization

Change-Id: If8181146f2f06d0d01b5fdb1046eaff930b7ba5d
Signed-off-by: Thomas Kosiewski <tk@coder.com>

.agents/skills/deep-review/SKILL.md

@@ -111,8 +111,8 @@ Tier 2 file filters:
 
 - **Modernization Reviewer**: one instance per language present in the diff. Filter by extension:
   - Go: `*.go` — reference `.claude/docs/GO.md` before reviewing.
-  - TypeScript: `*.ts` `*.tsx`
-  - React: `*.tsx` `*.jsx`
+  - TypeScript: `*.ts` `*.tsx`: reference `.agents/skills/deep-review/references/typescript.md` before reviewing.
+  - React: `*.tsx` `*.jsx`: reference `.agents/skills/deep-review/references/react.md` before reviewing.
 
   `.tsx` files match both TypeScript and React filters. Spawn both instances when the diff contains `.tsx` changes — TS covers language-level patterns; React covers component and hooks patterns. Before spawning, verify each instance's filter produces a non-empty diff. Skip instances whose filtered diff is empty.
 
@@ -155,9 +155,11 @@ File scope: {filter from step 2}.
 Output file: {REVIEW_DIR}/{role-name}.md
 ```
 
-For the Modernization Reviewer (Go), add after the methodology line:
+For Modernization Reviewer instances, add the language reference after the methodology line:
 
-> Read `.claude/docs/GO.md` as your Go language reference before reviewing.
+- **Go:** `Read .claude/docs/GO.md as your Go language reference before reviewing.`
+- **TypeScript:** `Read .agents/skills/deep-review/references/typescript.md as your TypeScript language reference before reviewing.`
+- **React:** `Read .agents/skills/deep-review/references/react.md as your React language reference before reviewing.`
 
 For re-reviews, append to both Tier 1 and Tier 2 prompts:
 

.agents/skills/deep-review/references/react.md

@@ -0,0 +1,305 @@
+# Modern React (18–19.2) + Compiler 1.0 — Reference
+
+Reference for writing idiomatic React. Covers what changed, what it replaced, and what to reach for. Includes React Compiler patterns — what the compiler handles automatically, what it changes semantically, and how to verify its behavior empirically. Scope: client-side SPA patterns only. Server Components, `use server`, and `use client` directives are framework-specific and omitted. Check the project's React version and compiler config before reaching for newer APIs.
+
+## How modern React thinks differently
+
+**Concurrent rendering** (18): React can now pause, interrupt, and resume renders. This is the foundation everything else builds on. Most existing code "just works," but components that produce side effects during render (mutations, subscriptions, network calls in the render body) are unsafe and will misbehave. Concurrent features are opt-in — they only activate when you use a concurrent API like `startTransition` or `useDeferredValue`.
+
+**Urgent vs. non-urgent updates** (18): The `startTransition` / `useTransition` API introduces a formal split between updates that must feel immediate (typing, clicking) and updates that can be interrupted (filtering a large list, navigating to a new screen). Non-urgent updates yield to urgent ones mid-render. Use this instead of `setTimeout` or manual debounce when you want the UI to stay responsive during expensive re-renders.
+
+**Actions** (19): Async functions passed to `startTransition` are called "Actions." They automatically manage pending state, error handling, and optimistic updates as a unit. The `useActionState` hook and `<form action={fn}>` prop are built on this. The pattern replaces the hand-rolled `isPending/setIsPending` + `try/catch` + `setError` boilerplate that was previously necessary for every data mutation.
+
+**Automatic batching** (18): State updates are now batched everywhere — inside `setTimeout`, `Promise.then`, native event handlers, etc. Previously batching only happened inside React-managed event handlers. If you genuinely need a synchronous flush, use `flushSync`.
+
+**Automatic memoization** (Compiler 1.0): React Compiler is a build-time Babel plugin that automatically inserts memoization into components and hooks. It replaces manual `useMemo`, `useCallback`, and `React.memo` — including conditional memoization and memoization after early returns, which manual APIs cannot express. The compiler only processes components and hooks, not standalone functions. It understands data flow and mutability through its own HIR (High-level Intermediate Representation), so it can memoize more granularly than a human would. Projects adopt it incrementally — typically via path-based Babel overrides or the `"use memo"` directive. Components that violate the Rules of React are silently skipped (no build error), so the automated lint tools that check compiler compatibility matter.
+
+## Replace these patterns
+
+The left column reflects patterns common before React 18/19. Write the right column instead. The "Since" column tells you the minimum React version required.
+
+| Old pattern                                                       | Modern replacement                                                             | Since |
+| ----------------------------------------------------------------- | ------------------------------------------------------------------------------ | ----- |
+| `ReactDOM.render(<App />, el)`                                    | `createRoot(el).render(<App />)`                                               | 18    |
+| `ReactDOM.hydrate(<App />, el)`                                   | `hydrateRoot(el, <App />)`                                                     | 18    |
+| `ReactDOM.unmountComponentAtNode(el)`                             | `root.unmount()`                                                               | 18    |
+| `ReactDOM.findDOMNode(this)`                                      | DOM ref: `const ref = useRef(); ref.current`                                   | 18    |
+| `<Context.Provider value={v}>`                                    | `<Context value={v}>`                                                          | 19    |
+| `React.forwardRef((props, ref) => ...)`                           | `function Comp({ ref, ...props }) { ... }` (ref as a regular prop)             | 19    |
+| String ref `ref="input"` in class components                      | Callback ref or `createRef()`                                                  | 19    |
+| `Heading.propTypes = { ... }`                                     | TypeScript / ES6 type annotations                                              | 19    |
+| `Component.defaultProps = { ... }` on function components         | ES6 default parameters `({ text = 'Hi' })`                                     | 19    |
+| Legacy Context: `contextTypes` + `getChildContext`                | `React.createContext()` + `contextType`                                        | 19    |
+| `import { act } from 'react-dom/test-utils'`                      | `import { act } from 'react'`                                                  | 19    |
+| `import ShallowRenderer from 'react-test-renderer/shallow'`       | `import ShallowRenderer from 'react-shallow-renderer'`                         | 19    |
+| Manual `isPending` state around async calls                       | `const [isPending, startTransition] = useTransition()`                         | 18    |
+| Manual optimistic state + revert logic                            | `useOptimistic(currentValue)`                                                  | 19    |
+| `useEffect` to subscribe to external stores                       | `useSyncExternalStore(subscribe, getSnapshot)`                                 | 18    |
+| Hand-rolled unique ID (counter, random, index)                    | `useId()` — SSR-safe, hydration-safe                                           | 18    |
+| `useEffect` to inject `<title>` or `<meta>` / `react-helmet`      | Render `<title>`, `<meta>`, `<link>` directly in components; React hoists them | 19    |
+| `ReactDOM.useFormState(action, initial)` (Canary name)            | `useActionState(action, initial)`                                              | 19    |
+| `useReducer<React.Reducer<State, Action>>(reducer)`               | `useReducer(reducer)` — infers from the reducer function                       | 19    |
+| `<div ref={current => (instance = current)} />` (implicit return) | `<div ref={current => { instance = current }} />` (explicit block body)        | 19    |
+| `useRef<T>()` with no argument                                    | `useRef<T>(undefined)` or `useRef<T \| null>(null)` — argument is now required | 19    |
+| `MutableRefObject<T>` type annotation                             | `RefObject<T>` — all refs are mutable now; `MutableRefObject` is deprecated    | 19    |
+| `React.createFactory('button')`                                   | `<button />` JSX                                                               | 19    |
+| `useMemo(() => expr, [deps])` in compiled components              | `const val = expr;` — compiler memoizes automatically                          | C 1.0 |
+| `useCallback(fn, [deps])` in compiled components                  | `const fn = () => { ... };` — compiler memoizes automatically                  | C 1.0 |
+| `React.memo(Component)` in compiled components                    | Plain component — compiler skips re-render when props are unchanged            | C 1.0 |
+| `eslint-plugin-react-compiler` (standalone)                       | `eslint-plugin-react-hooks@latest` (compiler rules merged into recommended)    | C 1.0 |
+| `useRef` + `useLayoutEffect` for stable callbacks                 | `useEffectEvent(fn)` — compiler handles both, but `useEffectEvent` is clearer  | 19.2  |
+
+## New capabilities
+
+These enable things that weren't practical before. Reach for them in the described situations.
+
+| What                                                                 | Since   | When to use it                                                                                                                                                                                                                                                                                                                                                                                                                                                              |
+| -------------------------------------------------------------------- | ------- | --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
+| `useTransition()` / `startTransition()`                              | 18      | Mark a state update as non-urgent so React can interrupt it to handle clicks or keystrokes. The `isPending` boolean lets you show a loading indicator without blocking the UI.                                                                                                                                                                                                                                                                                              |
+| `useDeferredValue(value, initialValue?)`                             | 18 / 19 | Defer re-rendering a slow subtree: pass the deferred value as a prop, wrap the expensive child in `memo`. Unlike debounce, uses no fixed timeout — renders as soon as the browser is idle. The `initialValue` arg (19) avoids a flash on first render.                                                                                                                                                                                                                      |
+| `useId()`                                                            | 18      | Generate a stable, SSR-consistent ID for accessibility attributes (`htmlFor`, `aria-describedby`). Do not use for list keys.                                                                                                                                                                                                                                                                                                                                                |
+| `useSyncExternalStore(subscribe, getSnapshot, getServerSnapshot?)`   | 18      | Subscribe to external (non-React) state stores safely under concurrent rendering. Preferred over `useEffect`-based subscriptions in libraries.                                                                                                                                                                                                                                                                                                                              |
+| `useActionState(action, initialState)`                               | 19      | Manage an async mutation: returns `[state, wrappedAction, isPending]`. Handles pending, result, and error state as a unit. Replaces the manual `isPending` + `try/catch` + `setError` pattern.                                                                                                                                                                                                                                                                              |
+| `useOptimistic(currentValue)`                                        | 19      | Show a speculative value while an async Action is in flight. Returns `[optimisticValue, setOptimistic]`. React automatically reverts to `currentValue` when the transition settles.                                                                                                                                                                                                                                                                                         |
+| `use(promiseOrContext)`                                              | 19      | Read a promise or Context value inside a component or custom hook. Unlike hooks, `use` can be called conditionally (after early returns). Promises must come from a cache — do not create them during render.                                                                                                                                                                                                                                                               |
+| `useFormStatus()` (from `react-dom`)                                 | 19      | Read `{ pending, data, method, action }` of the nearest parent `<form>` Action. Works across component boundaries without prop drilling — useful for submit buttons inside design-system components.                                                                                                                                                                                                                                                                        |
+| `useEffectEvent(fn)`                                                 | 19.2    | Extract a non-reactive callback from an effect. The function sees the latest props/state without being listed in deps, and is never stale. Replaces the `useRef`-and-mutate-in-layout-effect workaround for stable event-like callbacks. The compiler has built-in knowledge of this hook and correctly prunes its return value from effect dependency arrays. Both `useEffectEvent` and the old ref workaround compile cleanly; `useEffectEvent` is preferred for clarity. |
+| `<Activity>`                                                         | 19.2    | Hide part of the UI while preserving its state and DOM. React deprioritizes updates to hidden content. Use via framework APIs for route prerendering or tab preservation — not a direct replacement for CSS `visibility`.                                                                                                                                                                                                                                                   |
+| `captureOwnerStack()`                                                | 19.1    | Dev-only API that returns a string showing which components are responsible for rendering the current component (owner stack, not call stack). Useful for custom error overlays. Returns `null` in production.                                                                                                                                                                                                                                                              |
+| `<form action={fn}>`                                                 | 19      | Pass an async function as a form's `action` prop. React handles submission, pending state, and automatic form reset on success. Works with `useActionState` and `useFormStatus`.                                                                                                                                                                                                                                                                                            |
+| Ref cleanup function                                                 | 19      | Return a cleanup function from a ref callback: `ref={el => { ...; return () => cleanup(); }}`. React calls it on unmount. Replaces the pattern of checking `el === null` in the callback.                                                                                                                                                                                                                                                                                   |
+| `<link rel="stylesheet" precedence="default">`                       | 19      | Declare a stylesheet next to the component that needs it. React deduplicates and inserts it in the correct order before revealing Suspense content.                                                                                                                                                                                                                                                                                                                         |
+| `preinit`, `preload`, `prefetchDNS`, `preconnect` (from `react-dom`) | 19      | Imperatively hint the browser to load resources early. Call from render or event handlers. React deduplicates hints across the component tree.                                                                                                                                                                                                                                                                                                                              |
+| React Compiler (`babel-plugin-react-compiler`)                       | C 1.0   | Build-time automatic memoization for components and hooks. Install, add to Babel/Vite pipeline. Projects typically start with path-based overrides to compile a subset of files.                                                                                                                                                                                                                                                                                            |
+| `"use memo"` directive                                               | C 1.0   | Opt a single function into compilation when using `compilationMode: 'annotation'`. Place at the start of the function body. Module-level `"use memo"` at the top of a file compiles all functions in that file.                                                                                                                                                                                                                                                             |
+| `"use no memo"` directive                                            | C 1.0   | Temporary escape hatch — skip compilation for a specific component or hook that causes a runtime regression. Not a permanent solution. Place at the start of the function body.                                                                                                                                                                                                                                                                                             |
+| Compiler-powered ESLint rules                                        | C 1.0   | Rules for purity, refs, set-state-in-render, immutability, etc. now ship in `eslint-plugin-react-hooks` recommended preset. Surface Rules-of-React violations even without the compiler installed. Note: some projects use Biome instead — check project lint config.                                                                                                                                                                                                       |
+
+## Key APIs
+
+### `useTransition` and `startTransition` (18)
+
+`useTransition` returns `[isPending, startTransition]`. Wrap any state update that is not directly tied to the user's current gesture inside `startTransition`. React will render the old UI while computing the new one, and `isPending` is `true` during that window.
+
+In React 19, `startTransition` can accept an async function (an "Action"). React sets `isPending` to `true` for the entire duration of the async work, not just during the synchronous part.
+
+```tsx
+// 18: synchronous transition
+const [isPending, startTransition] = useTransition();
+startTransition(() => setQuery(input));
+
+// 19: async Action — isPending stays true until the await settles
+startTransition(async () => {
+	const err = await updateName(name);
+	if (err) setError(err);
+});
+```
+
+Use `startTransition` (the module-level export) when you cannot use the hook (outside a component, in a router callback, etc.).
+
+### `useDeferredValue` (18 / 19)
+
+Creates a "lagging" copy of a value. Pass it to a memoized, expensive component so that React can render the stale UI while computing the updated one.
+
+```tsx
+// 19: initialValue shows '' on first render; avoids loading flash
+const deferred = useDeferredValue(searchQuery, "");
+return <Results query={deferred} />; // Results wrapped in memo
+```
+
+`deferred !== searchQuery` while the deferred render is in progress — use this to show a "stale" indicator.
+
+### `useActionState` (19)
+
+Replaces the `useState` + `isPending` + `try/catch` + `setError` boilerplate for any async operation that can be retried or submitted as a form.
+
+```tsx
+const [error, submitAction, isPending] = useActionState(
+	async (prevState, formData) => {
+		const err = await updateName(formData.get("name"));
+		if (err) return err; // returned value becomes next state
+		redirect("/profile");
+		return null;
+	},
+	null, // initialState
+);
+
+// Use submitAction as the form's action prop or call it directly
+<form action={submitAction}>
+	<input name="name" />
+	<button disabled={isPending}>Save</button>
+	{error && <p>{error}</p>}
+</form>;
+```
+
+### `useOptimistic` (19)
+
+Shows a speculative value immediately while an async Action is in progress. React automatically reverts to the server-confirmed value when the Action resolves or rejects.
+
+```tsx
+const [optimisticName, setOptimisticName] = useOptimistic(currentName);
+
+const submit = async (formData) => {
+	const newName = formData.get("name");
+	setOptimisticName(newName); // shows immediately
+	await updateName(newName); // reverts if this throws
+};
+```
+
+### `use()` (19)
+
+Unlike hooks, `use` can appear after conditional statements. Two primary uses:
+
+**Reading a promise** (must be stable — from a cache, not created inline):
+
+```tsx
+function Comments({ commentsPromise }) {
+	const comments = use(commentsPromise); // suspends until resolved
+	return comments.map((c) => <p key={c.id}>{c.text}</p>);
+}
+```
+
+**Reading context after an early return** (hooks cannot appear after `return`):
+
+```tsx
+function Heading({ children }) {
+	if (!children) return null;
+	const theme = use(ThemeContext); // valid here; hooks would not be
+	return <h1 style={{ color: theme.color }}>{children}</h1>;
+}
+```
+
+### `useSyncExternalStore` (18)
+
+The correct way for libraries (and app code) to subscribe to non-React state. Prevents tearing under concurrent rendering.
+
+```tsx
+const value = useSyncExternalStore(
+	store.subscribe, // called when store changes
+	store.getSnapshot, // returns current value (must be stable reference if unchanged)
+	store.getServerSnapshot, // optional: for SSR
+);
+```
+
+## Verifying compiler behavior
+
+The compiler is a black box unless you inspect its output. When reviewing code in compiled paths, run the compiler on the specific code to see what it actually does. Do not guess — verify.
+
+**Run the compiler on a code snippet:**
+
+```sh
+cd site && node -e "
+const {transformSync} = require('@babel/core');
+const code = \`<paste component here>\`;
+const diagnostics = [];
+const result = transformSync(code, {
+  plugins: [
+    ['@babel/plugin-syntax-typescript', {isTSX: true}],
+    ['babel-plugin-react-compiler', {
+      logger: {
+        logEvent(_, event) {
+          if (event.kind === 'CompileError' || event.kind === 'CompileSkip') {
+            diagnostics.push(event.detail?.toString?.()?.substring(0, 200));
+          }
+        },
+      },
+    }],
+  ],
+  filename: 'test.tsx',
+});
+console.log('Compiled:', result.code.includes('_c('));
+if (diagnostics.length) console.log('Diagnostics:', diagnostics);
+console.log(result.code);
+"
+```
+
+**Reading compiled output:**
+
+- `const $ = _c(N)` — allocates N memoization cache slots.
+- `if ($[n] !== dep)` — cache invalidation guard. Re-computes when `dep` changes (referential equality).
+- `if ($[n] === Symbol.for("react.memo_cache_sentinel"))` — one-time initialization. Runs once on first render, cached forever after. This is how the compiler handles expressions with no reactive dependencies.
+- `_temp` functions — pure callbacks the compiler hoisted out of the component body.
+
+**Check all compiled files at once:**
+
+```sh
+cd site && pnpm run lint:compiler
+```
+
+This runs the compiler on every file in the compiled paths and reports CompileError / CompileSkip diagnostics. Zero diagnostics means all functions compiled cleanly.
+
+**What the compiler catches vs. what it does not:**
+
+The compiler emits `CompileError` for mutations of props, state, or hook arguments during render, and for `ref.current` access during render. The project's lint pipeline catches these automatically — do not flag them in review.
+
+The compiler does **not** flag impure function calls during render (`Math.random()`, `Date.now()`, `new Date()`). Instead it silently memoizes them with a sentinel guard, freezing the value after first render. This changes semantics without any diagnostic. Verify suspicious calls by running the compiler and checking for sentinel guards in the output.
+
+## Pitfalls
+
+Things that are easy to get wrong even when you know the modern API exists. Check your output against these.
+
+**Effects run twice in development with StrictMode.** React 18 intentionally mounts → unmounts → remounts every component in dev to surface effects that are not resilient to remounting. This is not a bug. If an effect breaks on the second mount, it is missing a cleanup function. Write `return () => cleanup()` from every effect that sets up a subscription, timer, or external resource.
+
+**Concurrent rendering can call render multiple times.** The render function (component body) may be called more than once before React commits to the DOM. Side effects (mutations, subscriptions, logging) in the render body will run multiple times. Move them into `useEffect` or event handlers.
+
+**Do not create promises during render and pass them to `use()`.** A new promise is created every render, causing an infinite suspend-retry loop. Create the promise outside the component (module level), or use a caching library (SWR, React Query, `cache()` from React) to stabilize it.
+
+**`useOptimistic` reverts automatically — do not fight it.** The optimistic value is a presentation layer only. When the Action settles, React replaces it with the real `currentValue` you passed in. Do not try to sync optimistic state back to your real state; let React handle the revert.
+
+**`flushSync` opts out of automatic batching.** If third-party code or a browser API (e.g. `ResizeObserver`) calls `setState` and you need synchronous DOM flushing, wrap with `flushSync(() => setState(...))`. This is a last resort; prefer letting React batch.
+
+**`forwardRef` still works in React 19 but will be deprecated.** Function components accept `ref` as a plain prop now. New code should use the prop directly. Existing `forwardRef` wrappers continue to work without changes; migrate when convenient.
+
+**`<Activity>` does not unmount.** Content inside a hidden `<Activity>` boundary stays mounted. Effects keep running. Use it for preserving scroll position or form state, not for preventing expensive mounts — use lazy loading for that.
+
+**TypeScript: implicit returns from ref callbacks are now type errors.** In React 19, returning anything other than a cleanup function (or nothing) from a ref callback is rejected by the TypeScript types. The most common case is arrow-function refs that implicitly return the DOM node:
+
+```tsx
+// Error in React 19 types:
+<div ref={el => (instance = el)} />
+
+// Fix — use a block body:
+<div ref={el => { instance = el; }} />
+```
+
+**TypeScript: `useRef` now requires an argument.** `useRef<T>()` with no argument is a type error. Pass `undefined` for mutable refs or `null` for DOM refs you initialize on mount: `useRef<T>(undefined)` / `useRef<HTMLDivElement | null>(null)`.
+
+**`useId` output format changed across versions.** React 18 produced `:r0:`. React 19.1 changed it to `«r0»`. React 19.2 changed it again to `_r0`. Do not parse or depend on the specific format — treat it as an opaque string.
+
+**`useFormStatus` reads the nearest parent `<form>` with a function `action`.** It does not reflect native HTML form submissions — only React Actions. A submit button that is a sibling of `<form>` (rather than a descendant) will not see the form's status.
+
+**Context as a provider (`<Context>`) requires React 19; `<Context.Provider>` still works.** Do not use `<Context>` shorthand in a codebase that needs to support React 18. The two forms can coexist during migration.
+
+**Compiler freezes impure expressions silently.** `Math.random()`, `Date.now()`, `new Date()`, and `window.innerWidth` in a component body all compile without diagnostics. The compiler wraps them in a sentinel guard (`Symbol.for("react.memo_cache_sentinel")`) that runs the expression once and caches the result forever. The value never updates on re-render. Fix: move to a `useState` initializer (`useState(() => Math.random())`), `useEffect`, or event handler.
+
+**Component granularity affects compiler optimization.** When one pattern in a component causes a `CompileError` (e.g., a necessary `ref.current` read during render), the compiler skips the **entire** component. If the rest of the component would benefit from compilation, extract the non-compilable pattern into a small child component. This keeps the parent compiled.
+
+**The compiler only memoizes components and hooks.** Standalone utility functions (even expensive ones called during render) are not compiled. If a utility function is truly expensive, it still needs its own caching strategy outside of React (e.g., a module-level cache, `WeakMap`, etc.).
+
+**Changing memoization can shift `useEffect` firing.** A value that was unstable before compilation may become stable after, causing an effect that depended on it to fire less often. Conversely, future compiler changes may alter memoization granularity. Effects that use memoized values as dependencies should be resilient to these changes — they should be true synchronization effects, not "run this when X changes" hacks.
+
+## Behavioral changes that affect code
+
+- **Automatic batching** (18): State updates in `setTimeout`, `Promise.then`, `addEventListener` callbacks, etc. are now batched into a single re-render. Previously only React synthetic event handlers were batched. Code that relied on unbatched updates (reading DOM synchronously after each `setState`) must use `flushSync`.
+
+- **StrictMode double-invoke** (18): In development, every component is mounted → unmounted → remounted with the previous state. Every effect runs cleanup → setup twice on initial mount. `useMemo` and `useCallback` also double-invoke their functions. Production behavior is unchanged. If a test or component breaks under this, the component had a latent cleanup bug.
+
+- **StrictMode ref double-invoke** (19): In development, ref callbacks are also invoked twice on mount (attach → detach → attach). Return a cleanup function from the ref callback to handle detach correctly.
+
+- **StrictMode memoization reuse** (19): During the second pass of double-rendering, `useMemo` and `useCallback` now reuse the cached result from the first pass instead of calling the function again. Components that are already StrictMode-compatible should not notice a difference.
+
+- **Suspense fallback commits immediately** (19): When a component suspends, React now commits the nearest `<Suspense>` fallback without waiting for sibling trees to finish rendering. After the fallback is shown, React "pre-warms" suspended siblings in the background. This makes fallbacks appear faster but changes the order of rendering work.
+
+- **Error re-throwing removed** (19): Errors that are not caught by an Error Boundary are now reported to `window.reportError` (not re-thrown). Errors caught by an Error Boundary go to `console.error` once. If your production monitoring relied on the re-thrown error, add handlers to `createRoot`: `createRoot(el, { onUncaughtError, onCaughtError })`.
+
+- **Transitions in `popstate` are synchronous** (19): Browser back/forward navigation triggers synchronous transition flushing. This ensures the URL and UI update together atomically during history navigation.
+
+- **`useEffect` from discrete events flushes synchronously** (18): Effects triggered by a click or keydown (discrete events) are now flushed synchronously before the browser paints, consistent with `useLayoutEffect` for those cases.
+
+- **Hydration mismatches treated as errors** (18 / improved in 19): Text content mismatches between server HTML and client render revert to client rendering up to the nearest `<Suspense>` boundary. React 19 logs a single diff instead of multiple warnings, making mismatches much easier to diagnose.
+
+- **New JSX transform required** (19): The automatic JSX runtime introduced in 2020 (`react/jsx-runtime`) is now mandatory. The classic transform (which required `import React from 'react'` in every file) is no longer supported. Most toolchains have already shipped the new transform; check your Babel or TypeScript config if you see warnings.
+
+- **UMD builds removed** (19): React no longer ships UMD bundles. Load via npm and a bundler, or use an ESM CDN (`import React from "https://esm.sh/react@19"`).
+
+- **React Compiler automatic memoization** (Compiler 1.0): Build-time Babel plugin that inserts memoization into components and hooks. Components that follow the Rules of React are automatically memoized; components that violate them are silently skipped (no build error, no runtime change). The compiler can memoize conditionally and after early returns — things impossible with manual `useMemo`/`useCallback`. Works with React 17+ via `react-compiler-runtime`; best with React 19+. Projects adopt incrementally via path-based Babel overrides, `compilationMode: 'annotation'`, or the `"use memo"` / `"use no memo"` directives. Check the project's Vite/Babel config to know which paths are compiled. Compiled components show a "Memo ✨" badge in React DevTools.

.agents/skills/deep-review/references/typescript.md

@@ -0,0 +1,199 @@
+# Modern TypeScript (5.0–6.0 RC) — Reference
+
+Reference for writing idiomatic TypeScript. Covers what changed, what it replaced, and what to reach for. Respect the project's minimum TypeScript version: don't emit features from a version newer than what the project targets. Check `package.json` and `tsconfig.json` before writing code.
+
+## How modern TypeScript thinks differently
+
+The 5.x era resolves years of module system ambiguity and cleans house on legacy options. Three themes dominate:
+
+**Module semantics are explicit.** `--verbatimModuleSyntax` (5.0) makes import/export intent visible in source: type imports must carry `type`, value imports stay. Combined with `--module preserve` or `--moduleResolution bundler`, the compiler now accurately models what bundlers and modern runtimes actually do. `import defer` (5.9) extends the model to deferred evaluation.
+
+**Resource lifetimes are first-class.** `using` and `await using` (5.2) provide deterministic cleanup without `try/finally`. Any object implementing `Symbol.dispose` participates. `DisposableStack` handles ad-hoc multi-resource cleanup in functions where creating a full class is overkill.
+
+**Inference is smarter about what it knows.** Inferred type predicates (5.5) let `.filter(x => x !== undefined)` produce `T[]` instead of `(T | undefined)[]` automatically. `NoInfer<T>` (5.4) gives library authors precise control over which parameters drive inference. Narrowing now survives closures after last assignment, constant indexed accesses, and `switch (true)` patterns.
+
+**TypeScript 6.0 is a transition release toward 7.0** (the Go-native port). It turns years of soft deprecations into errors and changes several defaults. Most impactful: `types` defaults to `[]` (must list `@types` packages explicitly), `rootDir` defaults to `.`, `strict` defaults to `true`, `module` defaults to `esnext`. Projects relying on implicit behavior need explicit config. Check the deprecations section before upgrading.
+
+## Replace these patterns
+
+The left column reflects patterns still common before TypeScript 5.x. Write the right column instead. The "Since" column tells you the minimum TypeScript version required.
+
+| Old pattern                                                                                                      | Modern replacement                                                                                                           | Since  |
+| ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | ------ |
+| `--experimentalDecorators` + legacy decorator signatures                                                         | Standard decorators (TC39): `function dec(target, context: ClassMethodDecoratorContext)` — no flag needed                    | 5.0    |
+| Requiring callers to add `as const` at call sites                                                                | `<const T extends HasNames>(arg: T)` — `const` modifier on type parameter                                                    | 5.0    |
+| `--importsNotUsedAsValues` + `--preserveValueImports`                                                            | `--verbatimModuleSyntax`                                                                                                     | 5.0    |
+| `import { Foo } from "..."` when `Foo` is only used as a type                                                    | `import { type Foo } from "..."` or `import type { Foo } from "..."`                                                         | 5.0    |
+| `"extends": "@tsconfig/strictest/tsconfig.json"` chain                                                           | `"extends": ["@tsconfig/strictest/tsconfig.json", "./tsconfig.base.json"]` (array form)                                      | 5.0    |
+| `try { ... } finally { resource.close(); resource.delete(); }`                                                   | `using resource = acquireResource()` — calls `[Symbol.dispose]()` automatically                                              | 5.2    |
+| `try { ... } finally { await resource.close() }`                                                                 | `await using resource = acquireAsyncResource()`                                                                              | 5.2    |
+| Ad-hoc cleanup with multiple `try/finally` blocks                                                                | `using cleanup = new DisposableStack(); cleanup.defer(() => ...)`                                                            | 5.2    |
+| `import data from "./data.json" assert { type: "json" }`                                                         | `import data from "./data.json" with { type: "json" }`                                                                       | 5.3    |
+| `.filter(Boolean)` or `.filter(x => !!x)` to remove nulls                                                        | `.filter(x => x !== undefined)` or `.filter(x => x !== null)` (infers type predicate)                                        | 5.5    |
+| Extra phantom type param to block inference bleed: `<C extends string, D extends C>`                             | `NoInfer<C>` on the parameter you don't want to drive inference                                                              | 5.4    |
+| `/** @typedef {import("./types").Foo} Foo */` in JS files                                                        | `/** @import { Foo } from "./types" */` (JSDoc `@import` tag)                                                                | 5.5    |
+| `myArray.reverse()` mutating in place                                                                            | `myArray.toReversed()` (returns new array)                                                                                   | 5.2    |
+| `myArray.sort(cmp)` mutating in place                                                                            | `myArray.toSorted(cmp)` (returns new array)                                                                                  | 5.2    |
+| `const copy = [...arr]; copy[i] = v`                                                                             | `arr.with(i, v)` (returns new array)                                                                                         | 5.2    |
+| Manual `has`/`get`/`set` pattern on `Map`                                                                        | `map.getOrInsert(key, defaultValue)` or `getOrInsertComputed(key, fn)`                                                       | 6.0 RC |
+| `new RegExp(str.replace(/[.\*+?^${}()\[\]\\]/g, '\\$&'))`                                                        | `new RegExp(RegExp.escape(str))`                                                                                             | 6.0 RC |
+| `--moduleResolution node` (node10)                                                                               | `--moduleResolution nodenext` (Node.js) or `--moduleResolution bundler` (bundlers/Bun)                                       | 6.0 RC |
+| `"baseUrl": "./src"` + `"@app/*": ["app/*"]` in paths                                                            | Remove `baseUrl`; use `"@app/*": ["./src/app/*"]` in paths directly                                                          | 6.0 RC |
+| `module Foo { export const x = 1; }`                                                                             | `namespace Foo { export const x = 1; }`                                                                                      | 6.0 RC |
+| `export * from "..."` when all re-exported members are types                                                     | `export type * from "..."` (or `export type * as ns from "..."`)                                                             | 5.0    |
+| `function f(): undefined { return undefined; }` — explicit return required in `: undefined`-returning function   | Remove the `return` entirely; `undefined`-returning functions no longer require any return statement                         | 5.1    |
+| Manual type predicate annotation on a simple arrow: `(x: T \| undefined): x is T => x !== undefined`             | Remove the annotation; TypeScript infers `x is T` from `!== null/undefined` and `instanceof` checks automatically            | 5.5    |
+| `const val = obj[key]; if (typeof val === "string") { use(val); }` — extract to const to narrow indexed access   | `if (typeof obj[key] === "string") { obj[key].toUpperCase(); }` directly — both `obj` and `key` must be effectively constant | 5.5    |
+| Copy narrowed `let`/param to a `const`, or restructure code to escape stale closure narrowing after reassignment | Remove the copy; narrowing survives into closures created after the last assignment to the variable                          | 5.4    |
+| `(arr as string[]).filter(...)` or restructure to avoid "not callable" errors on `string[] \| number[]`          | Call `.filter`, `.find`, `.some`, `.every`, `.reduce` directly on union-of-array types                                       | 5.2    |
+| `if`/`else` chain used to work around lack of narrowing inside a `switch (true)` body                            | `switch (true)` — each `case` condition now narrows the tested variable in its clause                                        | 5.3    |
+
+## New capabilities
+
+These enable things that weren't practical before. Reach for them in the described situations.
+
+| What                                            | Since  | When to use it                                                                                                                                                                                                                                |
+| ----------------------------------------------- | ------ | --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
+| `using` / `await using` declarations            | 5.2    | Any resource needing deterministic cleanup (file handles, DB connections, locks, event listeners). Object must implement `Symbol.dispose` / `Symbol.asyncDispose`.                                                                            |
+| `DisposableStack` / `AsyncDisposableStack`      | 5.2    | Ad-hoc multi-resource cleanup without creating a class. Call `.defer(fn)` right after acquiring each resource. Stack disposes in LIFO order.                                                                                                  |
+| `const` modifier on type parameters             | 5.0    | Force `const`-like (literal/readonly tuple) inference at call sites without requiring callers to write `as const`. Constraint must use `readonly` arrays.                                                                                     |
+| Decorator metadata (`Symbol.metadata`)          | 5.2    | Attach and read per-class metadata from decorators via `context.metadata`. Retrieved as `MyClass[Symbol.metadata]`. Requires `Symbol.metadata ??= Symbol(...)` polyfill.                                                                      |
+| `NoInfer<T>` utility type                       | 5.4    | Prevent a parameter from contributing inference candidates for `T`. Use when one argument should be the "source of truth" and others should only be checked against it.                                                                       |
+| Inferred type predicates                        | 5.5    | Filter callbacks that test for `!== null` or `instanceof` now automatically produce a type predicate. `Array.prototype.filter` then narrows the result array type.                                                                            |
+| `--isolatedDeclarations`                        | 5.5    | Require explicit return types on exported declarations. Unlocks parallel declaration emit by external tooling (esbuild, oxc, etc.) without needing a full type-checker pass.                                                                  |
+| `${configDir}` in tsconfig paths                | 5.5    | Anchor `typeRoots`, `paths`, `outDir`, etc. in a shared base tsconfig to the _consuming_ project's directory, not the shared file's location.                                                                                                 |
+| Always-truthy/nullish check errors              | 5.6    | Catches regex literals in `if`, arrow functions as comparators, `?? 100` on non-nullable left side, misplaced parentheses. No API to call; existing bugs now surface as errors.                                                               |
+| Iterator helper methods (`IteratorObject`)      | 5.6    | Built-in iterators from `Map`, `Set`, generators, etc. now have `.map()`, `.filter()`, `.take()`, `.drop()`, `.flatMap()`, `.toArray()`, `.reduce()`, etc. Use `Iterator.from(iterable)` to wrap any iterable.                                |
+| `--noUncheckedSideEffectImports`                | 5.6    | Error when a side-effect import (`import "..."`) resolves to nothing. Catches typos in polyfill or CSS imports.                                                                                                                               |
+| `--noCheck`                                     | 5.6    | Skip type checking entirely during emit. Useful for separating "fast emit" from "thorough check" pipeline stages, especially with `--isolatedDeclarations`.                                                                                   |
+| `--rewriteRelativeImportExtensions`             | 5.7    | Rewrite `.ts`→`.js`, `.tsx`→`.jsx`, `.mts`→`.mjs`, `.cts`→`.cjs` in relative imports during emit. Required when writing `.ts` imports for Node.js strip-types mode and still needing `.js` output for library distribution.                   |
+| `--erasableSyntaxOnly`                          | 5.8    | Error on constructs that can't be type-stripped by Node.js `--experimental-strip-types`: `enum`, `namespace` with code, parameter properties, `import =` aliases.                                                                             |
+| `require()` of ESM under `--module nodenext`    | 5.8    | Node.js 22+ allows CJS to `require()` ESM files (no top-level `await`). TypeScript now allows this under `nodenext` without error.                                                                                                            |
+| `import defer * as ns from "..."`               | 5.9    | Defer module _evaluation_ (not loading) until first property access. Module is loaded and verified at import time; side-effects are delayed. Only works with `--module preserve` or `esnext`.                                                 |
+| `Set` algebra methods                           | 5.5    | Non-mutating: `union`, `intersection`, `difference`, `symmetricDifference` → new `Set`. Predicate: `isSubsetOf`, `isSupersetOf`, `isDisjointFrom` → `boolean`. Requires `esnext` or `es2025` lib.                                             |
+| `Object.groupBy` / `Map.groupBy`                | 5.4    | Group an iterable into buckets by key function. Return type has all keys as optional (not every key is guaranteed present). Requires `esnext` or `es2024`+ lib.                                                                               |
+| `Temporal` API types                            | 6.0 RC | `Temporal.Now`, `Temporal.Instant`, `Temporal.PlainDate`, etc. Available under `esnext` or `esnext.temporal` lib. Usable in runtimes that already ship it (V8 118+, SpiderMonkey, etc.).                                                      |
+| `@satisfies` in JSDoc                           | 5.0    | Validates that a JS expression satisfies a type without widening it — the TS `satisfies` operator for `.js` files. Write `/** @satisfies {MyType} */` above the declaration or inline on a parenthesized expression.                          |
+| `@overload` in JSDoc                            | 5.0    | Declare multiple call signatures for a JS function. Each JSDoc comment tagged `@overload` is treated as a distinct overload; the final JSDoc comment (without `@overload`) describes the implementation signature.                            |
+| Getter/setter with completely unrelated types   | 5.1    | `get style(): CSSStyleDeclaration` and `set style(v: string)` can now have fully unrelated types, provided both have explicit type annotations. Previously the getter type was required to be a subtype of the setter type.                   |
+| `instanceof` narrowing via `Symbol.hasInstance` | 5.3    | When a class defines `static [Symbol.hasInstance](val: unknown): val is T`, the `instanceof` operator now narrows to the predicate type `T`, not the class type itself. Useful when the runtime check and the structural type differ.         |
+| Regex literal syntax checking                   | 5.5    | TypeScript validates regex literal syntax: malformed groups, nonexistent backreferences, named capture mismatches, and features not available at the current `--target`. No API needed; existing latent bugs surface as errors automatically. |
+| `--build` continues past intermediate errors    | 5.6    | `tsc --build` no longer stops at the first failing project. All projects are built and errors reported together. Use `--stopOnBuildErrors` to restore the old stop-on-first-error behavior. Useful for monorepos during upgrades.             |
+| `--module node18`                               | 5.8    | Stable `--module` flag for Node.js 18 semantics: disallows `require()` of ESM (unlike `nodenext`) and still allows import assertions. Use when pinned to Node 18 and not ready for `nodenext` behavior changes.                               |
+| `--module node20`                               | 5.9    | Stable `--module` flag for Node.js 20 semantics: permits `require()` of ESM, rejects import assertions. Implies `--target es2023` (unlike `nodenext`, which floats to `esnext`).                                                              |
+
+## Key APIs
+
+### `Disposable` / `AsyncDisposable` / stacks (5.2)
+
+Global types provided by TypeScript's lib (requires `esnext.disposable` or `esnext` in `lib`):
+
+- `Disposable` — `{ [Symbol.dispose](): void }`
+- `AsyncDisposable` — `{ [Symbol.asyncDispose](): PromiseLike<void> }`
+- `DisposableStack` — `defer(fn)`, `use(resource)`, `adopt(value, disposeFn)`, `move()`. Is itself `Disposable`.
+- `AsyncDisposableStack` — async equivalent. Is itself `AsyncDisposable`.
+- `SuppressedError` — thrown when both the scope body and a `[Symbol.dispose]` throw. `.error` holds the dispose-phase error; `.suppressed` holds the original error.
+
+Polyfill the symbols in older runtimes:
+
+```ts
+Symbol.dispose ??= Symbol("Symbol.dispose");
+Symbol.asyncDispose ??= Symbol("Symbol.asyncDispose");
+```
+
+### Decorator context types (5.0)
+
+Each decorator kind receives a typed context object as its second parameter:
+
+- `ClassDecoratorContext`
+- `ClassMethodDecoratorContext`
+- `ClassGetterDecoratorContext`
+- `ClassSetterDecoratorContext`
+- `ClassFieldDecoratorContext`
+- `ClassAccessorDecoratorContext`
+
+All context objects have `.name`, `.kind`, `.static`, `.private`, and `.metadata`. Method/getter/setter/accessor contexts also have `.addInitializer(fn)` for running code at construction time.
+
+### `IteratorObject` (5.6)
+
+`IteratorObject<T, TReturn, TNext>` is the new type for built-in iterable iterators. Key methods: `map`, `filter`, `take`, `drop`, `flatMap`, `forEach`, `reduce`, `some`, `every`, `find`, `toArray`. Not the same as the pre-existing structural `Iterator<T>` protocol.
+
+- Generators produce `Generator<T>` which extends `IteratorObject`.
+- `Map.prototype.entries()` returns `MapIterator<[K, V]>`, `Set.prototype.values()` returns `SetIterator<T>`, etc.
+- `Iterator.from(iterable)` converts any `Iterable` to an `IteratorObject`.
+- `AsyncIteratorObject` exists for async parity.
+- `--strictBuiltinIteratorReturn` (new `--strict`-mode flag in 5.6) makes the return type of `BuiltinIteratorReturn` be `undefined` instead of `any`, catching unchecked `done` access.
+
+### Array copying methods (5.2)
+
+Declared on `Array`, `ReadonlyArray`, and all `TypedArray` types. Use these instead of the mutating variants when you need to preserve the original:
+
+| Mutating                           | Non-mutating copy                     |
+| ---------------------------------- | ------------------------------------- |
+| `arr.sort(cmp)`                    | `arr.toSorted(cmp)`                   |
+| `arr.reverse()`                    | `arr.toReversed()`                    |
+| `arr.splice(start, del, ...items)` | `arr.toSpliced(start, del, ...items)` |
+| `arr[i] = v`                       | `arr.with(i, v)`                      |
+
+## Pitfalls
+
+Things easy to get wrong even when you know the modern API exists. Check your output against these.
+
+**tsconfig defaults changed hard in 6.0.** `types: []` means no `@types/*` packages load implicitly. If you see floods of "cannot find name 'process'" or "cannot find module 'fs'" after upgrading to 6.0, add `"types": ["node"]` (or whatever you need) to `compilerOptions`. `rootDir: "."` means a project with source in `src/` will emit to `dist/src/` instead of `dist/` — add `"rootDir": "./src"` explicitly. `strict: true` by default means projects with loose code see new errors.
+
+**`using` requires a runtime polyfill on older runtimes.** `Symbol.dispose` and `Symbol.asyncDispose` don't exist before Node.js 18.x / Chrome 120. Add the two-line polyfill at your entry point. `DisposableStack` and `AsyncDisposableStack` need a more substantial polyfill (e.g. from `@microsoft/using-polyfill`).
+
+**`using` disposes in LIFO order.** Resources declared later in a scope are disposed first. Declare in the order you want reversed cleanup (acquisition order). `DisposableStack.defer` also runs in LIFO order.
+
+**Inferred type predicates have if-and-only-if semantics.** `x => !!x` does NOT infer `x is NonNullable<T>` because `0`, `""`, and `false` are falsy but not absent. TypeScript correctly refuses the predicate. Use `x => x !== undefined` or `x => x !== null` for precise null/undefined filters. If a predicate isn't being inferred, the false branch is probably ambiguous.
+
+**`--verbatimModuleSyntax` breaks CJS `require` emit.** Under this flag ESM `import`/`export` is emitted verbatim. You cannot produce `require()` calls from standard `import` syntax. For CJS output you must use `import foo = require("foo")` and `export = { ... }` syntax explicitly.
+
+**`NoInfer<T>` doesn't prevent `T` from being resolved, only from being contributed at that position.** Other parameters can still infer `T`. It means "don't use me as an inference candidate", not "block `T` from being resolved".
+
+**`--isolatedDeclarations` requires explicit return types on all exports.** Exported arrow functions, function declarations, and class methods all need annotations if their return type isn't trivially inferrable from a literal or type assertion. Editor quick-fixes can add them automatically.
+
+**Standard decorators are incompatible with `--experimentalDecorators`.** Different type signatures, metadata model, and emit. A decorator written for one will not work with the other. `--emitDecoratorMetadata` is not supported with standard decorators. Don't mix the two systems in one project.
+
+**`import defer` does not downlevel.** TypeScript does not transform `import defer` to polyfill-compatible code. The module is still _loaded_ eagerly (must exist); only _evaluation_ is deferred. Only use it under `--module preserve` or `esnext` with a runtime or bundler that supports it.
+
+**`--erasableSyntaxOnly` prohibits parameter properties.** `constructor(public x: number)` is not allowed. Expand to an explicit field declaration plus assignment in the constructor body.
+
+**Closure narrowing is invalidated if the variable is assigned anywhere in a nested function.** TypeScript cannot know when a nested function will run, so any assignment to a `let`/param inside a nested function — even a no-op like `value = value` — invalidates narrowing for all closures in the outer scope. Only the outer "no further assignments after this point" pattern is safe.
+
+**Constant indexed access narrowing requires both `obj` and `key` to be unmodified between the check and the use.** If either is a `let` that could be reassigned, TypeScript will not narrow `obj[key]`. Extract the value to a `const` in that case.
+
+**`switch (true)` narrowing does not carry across fall-through cases.** In a `switch (true)`, each `case` condition narrows independently. A variable narrowed in `case typeof x === "string":` that falls through to the next case will have its narrowing widened by the next condition, not accumulated from the previous one.
+
+**`const` type parameter modifier falls back when constraint is mutable.** `<const T extends string[]>(args: T)` falls back to `string[]` because `readonly ["a", "b"]` isn't assignable to `string[]`. Use `<const T extends readonly string[]>` for arrays.
+
+**`assert` import syntax errors under `--module nodenext` since 5.8.** Any remaining `import x from "..." assert { ... }` must be updated to `import x from "..." with { ... }`.
+
+**`Array.prototype.filter(x => x !== null)` now narrows to non-null (5.5).** This is almost always correct, but if you intentionally needed the nullable type downstream, add an explicit annotation: `const items: (T | null)[] = arr.filter(x => x !== null)`.
+
+## Behavioral changes that affect code
+
+- **All enums are union enums** (5.0): Every enum member gets its own literal type. Out-of-domain literal assignment to an enum type now errors. Cross-enum assignment between enums with identical names but differing values now errors.
+- **Relational operators no longer allow implicit string/number coercions** (5.0): `ns > 4` where `ns: number | string` is a type error. Use `+ns > 4` to explicitly coerce.
+- **`--module`/`--moduleResolution` must agree on node flavor** (5.2): Mixing `--module nodenext` with `--moduleResolution bundler` is an error. Use `--module nodenext` alone or `--module esnext --moduleResolution bundler`.
+- **Deprecations from 5.0 become hard errors in 5.5**: `--importsNotUsedAsValues`, `--preserveValueImports`, `--target ES3`, `--out`, and several others are fully removed in 5.5. They can no longer be specified, even with `"ignoreDeprecations": "5.0"`. Migrate to `--verbatimModuleSyntax` for the import flags.
+- **Type-only imports conflicting with local values** (5.4): Under `--isolatedModules`, `import { Foo } from "..."` where a local `let Foo` also exists now errors. Use `import type { Foo }` or `import { type Foo }`.
+- **Reference directives no longer synthesized or preserved in declaration emit** (5.5): `/// <reference types="node" />` TypeScript used to add automatically is no longer emitted. User-written directives are dropped unless they carry `preserve="true"`. Update library `tsconfig.json` if you relied on this.
+- **`.mts` files never emit CJS; `.cts` files never emit ESM** (5.6): Regardless of `--module` setting. Previously the extension was ignored in some modes.
+- **JSON imports under `--module nodenext` require `with { type: "json" }`** (5.7): `import data from "./config.json"` without the attribute is now a type error.
+- **`TypedArray`s are now generic** (5.7): `Uint8Array` is `Uint8Array<TArrayBuffer extends ArrayBufferLike = ArrayBufferLike>`. Code passing `Buffer` (from `@types/node`) to typed-array parameters may see new errors. Update `@types/node` to a version that matches.
+- **`import assert { ... }` is an error under `--module nodenext`** (5.8): Node.js 22 dropped support for the old syntax. Use `with { ... }`.
+- **`types` defaults to `[]` in 6.0**: All implicit `@types/*` loading stops. Add an explicit `"types": ["node"]` or the array will remain empty. Using `"types": ["*"]` restores the 5.x behavior.
+- **`rootDir` defaults to `.` (the tsconfig directory) in 6.0**: Previously inferred from the common ancestor of all source files. Projects with `"include": ["./src"]` and no explicit `rootDir` will now emit into `dist/src/` instead of `dist/`. Add `"rootDir": "./src"` to fix.
+- **`strict` defaults to `true` in 6.0**: Projects that were implicitly not strict will see new errors. Set `"strict": false` explicitly if you're not ready to fix them.
+- **`--baseUrl` deprecated in 6.0** and no longer acts as a module resolution root. Add explicit prefixes to your `paths` entries instead.
+- **`--moduleResolution node` (node10) deprecated in 6.0**: Removed in 7.0. Migrate to `nodenext` or `bundler`.
+- **`amd`, `umd`, `systemjs`, `none` module targets deprecated in 6.0**: Removed in 7.0. Migrate to a bundler.
+- **`--outFile` removed in 6.0**: Use a bundler (esbuild, Rollup, Webpack, etc.).
+- **`module Foo { }` syntax removed in 6.0**: Rename all such declarations to `namespace Foo { }`.
+- **`--esModuleInterop false` and `--allowSyntheticDefaultImports false` removed in 6.0**: Safe interop is now always on. Default imports from CJS modules (`import express from "express"`) are always valid.
+- **Explicit `typeRoots` disables upward `node_modules/@types` fallback** (5.1): When `typeRoots` is specified and a lookup fails in those directories, TypeScript no longer walks parent directories for `@types`. If you relied on the fallback, add `"./node_modules/@types"` explicitly to your `typeRoots` array.
+- **`super.` on instance field properties is a type error** (5.3): Calling `super.foo()` where `foo` is a class field (arrow function assigned in the constructor) rather than a prototype method now errors. Instance fields don't exist on the prototype; `super.field` is `undefined` at runtime.
+- **`--build` always emits `.tsbuildinfo`** (5.6): Previously only written when `--incremental` or `--composite` was set. Now written unconditionally in any `--build` invocation. Update `.gitignore` or CI artifact management if needed.
+- **`.mts`/`.cts` extensions and `package.json` `"type"` respected in all module modes** (5.6): Format-specific extensions and the `"type"` field inside `node_modules` are now honored regardless of `--module` setting (except `amd`, `umd`, `system`). A `.mts` file will never emit CJS output even under `--module commonjs`.
+- **Granular return expression checking** (5.8): Each branch of a conditional expression (`cond ? a : b`) directly inside a `return` statement is now checked individually against the declared return type. Previously an `any`-typed branch could silently suppress type errors in the other branch.

.github/cherry-pick-bot.yml

@@ -1,2 +0,0 @@
-enabled: true
-preservePullRequestTitle: true

.github/dependabot.yaml

@@ -82,9 +82,6 @@ updates:
       mui:
         patterns:
           - "@mui*"
-      radix:
-        patterns:
-          - "@radix-ui/*"
       react:
         patterns:
           - "react"
@@ -94,12 +91,6 @@ updates:
       emotion:
         patterns:
           - "@emotion*"
-        exclude-patterns:
-          - "jest-runner-eslint"
-      jest:
-        patterns:
-          - "jest"
-          - "@types/jest"
       vite:
         patterns:
           - "vite*"

.github/workflows/backport.yaml

@@ -0,0 +1,178 @@
+# Automatically backport merged PRs to the last N release branches when the
+# "backport" label is applied. Works whether the label is added before or
+# after the PR is merged.
+#
+# Usage:
+#   1. Add the "backport" label to a PR targeting main.
+#   2. When the PR merges (or if already merged), the workflow detects the
+#      latest release/* branches and opens one cherry-pick PR per branch.
+#
+# The created backport PRs follow existing repo conventions:
+#   - Branch:  backport/<pr>-to-<version>
+#   - Title:   <original PR title> (#<pr>)
+#   - Body:    links back to the original PR and merge commit
+
+name: Backport
+on:
+  pull_request_target:
+    branches:
+      - main
+    types:
+      - closed
+      - labeled
+
+permissions:
+  contents: write
+  pull-requests: write
+
+# Prevent duplicate runs for the same PR when both 'closed' and 'labeled'
+# fire in quick succession.
+concurrency:
+  group: backport-${{ github.event.pull_request.number }}
+
+jobs:
+  detect:
+    name: Detect target branches
+    if: >
+      github.event.pull_request.merged == true &&
+      contains(github.event.pull_request.labels.*.name, 'backport')
+    runs-on: ubuntu-latest
+    outputs:
+      branches: ${{ steps.find.outputs.branches }}
+    steps:
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+        with:
+          # Need all refs to discover release branches.
+          fetch-depth: 0
+
+      - name: Find latest release branches
+        id: find
+        run: |
+          # List remote release branches matching the exact release/2.X
+          # pattern (no suffixes like release/2.31_hotfix), sort by minor
+          # version descending, and take the top 3.
+          BRANCHES=$(
+            git branch -r \
+              | grep -E '^\s*origin/release/2\.[0-9]+$' \
+              | sed 's|.*origin/||' \
+              | sort -t. -k2 -n -r \
+              | head -3
+          )
+
+          if [ -z "$BRANCHES" ]; then
+            echo "No release branches found."
+            echo "branches=[]" >> "$GITHUB_OUTPUT"
+            exit 0
+          fi
+
+          # Convert to JSON array for the matrix.
+          JSON=$(echo "$BRANCHES" | jq -Rnc '[inputs | select(length > 0)]')
+          echo "branches=$JSON" >> "$GITHUB_OUTPUT"
+          echo "Will backport to: $JSON"
+
+  backport:
+    name: "Backport to ${{ matrix.branch }}"
+    needs: detect
+    if: needs.detect.outputs.branches != '[]'
+    runs-on: ubuntu-latest
+    strategy:
+      matrix:
+        branch: ${{ fromJson(needs.detect.outputs.branches) }}
+      fail-fast: false
+    env:
+      PR_NUMBER: ${{ github.event.pull_request.number }}
+      PR_TITLE: ${{ github.event.pull_request.title }}
+      PR_URL: ${{ github.event.pull_request.html_url }}
+      MERGE_SHA: ${{ github.event.pull_request.merge_commit_sha }}
+      SENDER: ${{ github.event.sender.login }}
+    steps:
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+        with:
+          # Full history required for cherry-pick.
+          fetch-depth: 0
+
+      - name: Cherry-pick and open PR
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+        run: |
+          set -euo pipefail
+
+          RELEASE_VERSION="${{ matrix.branch }}"
+          # Strip the release/ prefix for naming.
+          VERSION="${RELEASE_VERSION#release/}"
+          BACKPORT_BRANCH="backport/${PR_NUMBER}-to-${VERSION}"
+
+          git config user.name "github-actions[bot]"
+          git config user.email "41898282+github-actions[bot]@users.noreply.github.com"
+
+          # Check if backport branch already exists (idempotency for re-runs).
+          if git ls-remote --exit-code origin "refs/heads/${BACKPORT_BRANCH}" >/dev/null 2>&1; then
+            echo "Backport branch ${BACKPORT_BRANCH} already exists, skipping."
+            exit 0
+          fi
+
+          # Create the backport branch from the target release branch.
+          git checkout -b "$BACKPORT_BRANCH" "origin/${RELEASE_VERSION}"
+
+          # Cherry-pick the merge commit. Use -x to record provenance and
+          # -m1 to pick the first parent (the main branch side).
+          CONFLICTS=false
+          if ! git cherry-pick -x -m1 "$MERGE_SHA"; then
+            echo "::warning::Cherry-pick to ${RELEASE_VERSION} had conflicts."
+            CONFLICTS=true
+
+            # Abort the failed cherry-pick and create an empty commit
+            # explaining the situation.
+            git cherry-pick --abort
+            git commit --allow-empty -m "Cherry-pick of #${PR_NUMBER} requires manual resolution
+
+          The automatic cherry-pick of ${MERGE_SHA} to ${RELEASE_VERSION} had conflicts.
+          Please cherry-pick manually:
+
+              git cherry-pick -x -m1 ${MERGE_SHA}"
+          fi
+
+          git push origin "$BACKPORT_BRANCH"
+
+          TITLE="${PR_TITLE} (#${PR_NUMBER})"
+          BODY=$(cat <<EOF
+          Backport of ${PR_URL}
+
+          Original PR: #${PR_NUMBER} — ${PR_TITLE}
+          Merge commit: ${MERGE_SHA}
+          Requested by: @${SENDER}
+          EOF
+          )
+
+          if [ "$CONFLICTS" = true ]; then
+            TITLE="${TITLE} (conflicts)"
+            BODY="${BODY}
+
+          > [!WARNING]
+          > The automatic cherry-pick had conflicts.
+          > Please resolve manually by cherry-picking the original merge commit:
+          >
+          > \`\`\`
+          > git fetch origin ${BACKPORT_BRANCH}
+          > git checkout ${BACKPORT_BRANCH}
+          > git reset --hard origin/${RELEASE_VERSION}
+          > git cherry-pick -x -m1 ${MERGE_SHA}
+          > # resolve conflicts, then push
+          > \`\`\`"
+          fi
+
+          # Check if a PR already exists for this branch (idempotency
+          # for re-runs).
+          EXISTING_PR=$(gh pr list --head "$BACKPORT_BRANCH" --base "$RELEASE_VERSION" --state all --json number --jq '.[0].number // empty')
+          if [ -n "$EXISTING_PR" ]; then
+            echo "PR #${EXISTING_PR} already exists for ${BACKPORT_BRANCH}, skipping."
+            exit 0
+          fi
+
+          gh pr create \
+            --base "$RELEASE_VERSION" \
+            --head "$BACKPORT_BRANCH" \
+            --title "$TITLE" \
+            --body "$BODY" \
+            --assignee "$SENDER" \
+            --reviewer "$SENDER"

.github/workflows/cherry-pick.yaml

@@ -0,0 +1,152 @@
+# Automatically cherry-pick merged PRs to the latest release branch when the
+# "cherry-pick" label is applied. Works whether the label is added before or
+# after the PR is merged.
+#
+# Usage:
+#   1. Add the "cherry-pick" label to a PR targeting main.
+#   2. When the PR merges (or if already merged), the workflow detects the
+#      latest release/* branch and opens a cherry-pick PR against it.
+#
+# The created PRs follow existing repo conventions:
+#   - Branch:  backport/<pr>-to-<version>
+#   - Title:   <original PR title> (#<pr>)
+#   - Body:    links back to the original PR and merge commit
+
+name: Cherry-pick to release
+on:
+  pull_request_target:
+    branches:
+      - main
+    types:
+      - closed
+      - labeled
+
+permissions:
+  contents: write
+  pull-requests: write
+
+# Prevent duplicate runs for the same PR when both 'closed' and 'labeled'
+# fire in quick succession.
+concurrency:
+  group: cherry-pick-${{ github.event.pull_request.number }}
+
+jobs:
+  cherry-pick:
+    name: Cherry-pick to latest release
+    if: >
+      github.event.pull_request.merged == true &&
+      contains(github.event.pull_request.labels.*.name, 'cherry-pick')
+    runs-on: ubuntu-latest
+    env:
+      PR_NUMBER: ${{ github.event.pull_request.number }}
+      PR_TITLE: ${{ github.event.pull_request.title }}
+      PR_URL: ${{ github.event.pull_request.html_url }}
+      MERGE_SHA: ${{ github.event.pull_request.merge_commit_sha }}
+      SENDER: ${{ github.event.sender.login }}
+    steps:
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+        with:
+          # Full history required for cherry-pick and branch discovery.
+          fetch-depth: 0
+
+      - name: Cherry-pick and open PR
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+        run: |
+          set -euo pipefail
+
+          # Find the latest release branch matching the exact release/2.X
+          # pattern (no suffixes like release/2.31_hotfix).
+          RELEASE_BRANCH=$(
+            git branch -r \
+              | grep -E '^\s*origin/release/2\.[0-9]+$' \
+              | sed 's|.*origin/||' \
+              | sort -t. -k2 -n -r \
+              | head -1
+          )
+
+          if [ -z "$RELEASE_BRANCH" ]; then
+            echo "::error::No release branch found."
+            exit 1
+          fi
+
+          # Strip the release/ prefix for naming.
+          VERSION="${RELEASE_BRANCH#release/}"
+          BACKPORT_BRANCH="backport/${PR_NUMBER}-to-${VERSION}"
+
+          echo "Target branch: $RELEASE_BRANCH"
+          echo "Backport branch: $BACKPORT_BRANCH"
+
+          # Check if backport branch already exists (idempotency for re-runs).
+          if git ls-remote --exit-code origin "refs/heads/${BACKPORT_BRANCH}" >/dev/null 2>&1; then
+            echo "Branch ${BACKPORT_BRANCH} already exists, skipping."
+            exit 0
+          fi
+
+          git config user.name "github-actions[bot]"
+          git config user.email "41898282+github-actions[bot]@users.noreply.github.com"
+
+          # Create the backport branch from the target release branch.
+          git checkout -b "$BACKPORT_BRANCH" "origin/${RELEASE_BRANCH}"
+
+          # Cherry-pick the merge commit. Use -x to record provenance and
+          # -m1 to pick the first parent (the main branch side).
+          CONFLICT=false
+          if ! git cherry-pick -x -m1 "$MERGE_SHA"; then
+            CONFLICT=true
+            echo "::warning::Cherry-pick to ${RELEASE_BRANCH} had conflicts."
+
+            # Abort the failed cherry-pick and create an empty commit with
+            # instructions so the PR can still be opened.
+            git cherry-pick --abort
+            git commit --allow-empty -m "cherry-pick of #${PR_NUMBER} failed — resolve conflicts manually
+
+          Cherry-pick of ${MERGE_SHA} onto ${RELEASE_BRANCH} had conflicts.
+          To resolve:
+            git fetch origin ${BACKPORT_BRANCH}
+            git checkout ${BACKPORT_BRANCH}
+            git cherry-pick -x -m1 ${MERGE_SHA}
+            # resolve conflicts
+            git push origin ${BACKPORT_BRANCH}"
+          fi
+
+          git push origin "$BACKPORT_BRANCH"
+
+          BODY=$(cat <<EOF
+          Cherry-pick of ${PR_URL}
+
+          Original PR: #${PR_NUMBER} — ${PR_TITLE}
+          Merge commit: ${MERGE_SHA}
+          Requested by: @${SENDER}
+          EOF
+          )
+
+          TITLE="${PR_TITLE} (#${PR_NUMBER})"
+          if [ "$CONFLICT" = true ]; then
+            TITLE="[CONFLICT] ${TITLE}"
+          fi
+
+          # Check if a PR already exists for this branch (idempotency
+          # for re-runs). Use --state all to catch closed/merged PRs too.
+          EXISTING_PR=$(gh pr list --head "$BACKPORT_BRANCH" --base "$RELEASE_BRANCH" --state all --json number --jq '.[0].number // empty')
+          if [ -n "$EXISTING_PR" ]; then
+            echo "PR #${EXISTING_PR} already exists for ${BACKPORT_BRANCH}, skipping."
+            exit 0
+          fi
+
+          NEW_PR_URL=$(
+            gh pr create \
+              --base "$RELEASE_BRANCH" \
+              --head "$BACKPORT_BRANCH" \
+              --title "$TITLE" \
+              --body "$BODY" \
+              --assignee "$SENDER" \
+              --reviewer "$SENDER"
+          )
+
+          # Comment on the original PR to notify the author.
+          COMMENT="Cherry-pick PR created: ${NEW_PR_URL}"
+          if [ "$CONFLICT" = true ]; then
+            COMMENT="${COMMENT} (⚠️ conflicts need manual resolution)"
+          fi
+          gh pr comment "$PR_NUMBER" --body "$COMMENT"

.github/workflows/ci.yaml

@@ -35,7 +35,7 @@ jobs:
       tailnet-integration: ${{ steps.filter.outputs.tailnet-integration }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -157,7 +157,7 @@ jobs:
     runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -204,7 +204,7 @@ jobs:
 
       # Needed for helm chart linting
       - name: Install helm
-        uses: azure/setup-helm@1a275c3b69536ee54be43f2070a358922e12c8d4 # v4.3.1
+        uses: azure/setup-helm@dda3372f752e03dde6b3237bc9431cdc2f7a02a2 # v5.0.0
         with:
           version: v3.9.2
         continue-on-error: true
@@ -247,7 +247,7 @@ jobs:
     runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -272,7 +272,7 @@ jobs:
     if: ${{ !cancelled() }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -327,7 +327,7 @@ jobs:
     timeout-minutes: 20
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -379,7 +379,7 @@ jobs:
           - windows-2022
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -575,7 +575,7 @@ jobs:
     timeout-minutes: 25
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -637,7 +637,7 @@ jobs:
     timeout-minutes: 25
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -709,7 +709,7 @@ jobs:
     timeout-minutes: 20
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -736,7 +736,7 @@ jobs:
     timeout-minutes: 20
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -769,7 +769,7 @@ jobs:
     name: ${{ matrix.variant.name }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -849,7 +849,7 @@ jobs:
     if: needs.changes.outputs.site == 'true' || needs.changes.outputs.ci == 'true'
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -870,7 +870,7 @@ jobs:
       # the check to pass. This is desired in PRs, but not in mainline.
       - name: Publish to Chromatic (non-mainline)
         if: github.ref != 'refs/heads/main' && github.repository_owner == 'coder'
-        uses: chromaui/action@07791f8243f4cb2698bf4d00426baf4b2d1cb7e0 # v13.3.5
+        uses: chromaui/action@f191a0224b10e1a38b2091cefb7b7a2337009116 # v16.0.0
         env:
           NODE_OPTIONS: "--max_old_space_size=4096"
           STORYBOOK: true
@@ -902,7 +902,7 @@ jobs:
       # infinitely "in progress" in mainline unless we re-review each build.
       - name: Publish to Chromatic (mainline)
         if: github.ref == 'refs/heads/main' && github.repository_owner == 'coder'
-        uses: chromaui/action@07791f8243f4cb2698bf4d00426baf4b2d1cb7e0 # v13.3.5
+        uses: chromaui/action@f191a0224b10e1a38b2091cefb7b7a2337009116 # v16.0.0
         env:
           NODE_OPTIONS: "--max_old_space_size=4096"
           STORYBOOK: true
@@ -930,7 +930,7 @@ jobs:
 
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -1005,7 +1005,7 @@ jobs:
     if: always()
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -1043,7 +1043,7 @@ jobs:
     runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -1097,7 +1097,7 @@ jobs:
       IMAGE: ghcr.io/coder/coder-preview:${{ steps.build-docker.outputs.tag }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -1479,7 +1479,7 @@ jobs:
     if: needs.changes.outputs.db == 'true' || needs.changes.outputs.ci == 'true' || github.ref == 'refs/heads/main'
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 

.github/workflows/dependabot.yaml

@@ -23,7 +23,7 @@ jobs:
     steps:
       - name: Dependabot metadata
         id: metadata
-        uses: dependabot/fetch-metadata@21025c705c08248db411dc16f3619e6b5f9ea21a # v2.5.0
+        uses: dependabot/fetch-metadata@ffa630c65fa7e0ecfa0625b5ceda64399aea1b36 # v3.0.0
         with:
           github-token: "${{ secrets.GITHUB_TOKEN }}"
 

.github/workflows/deploy.yaml

@@ -36,7 +36,7 @@ jobs:
       verdict: ${{ steps.check.outputs.verdict }} # DEPLOY or NOOP
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -65,7 +65,7 @@ jobs:
       packages: write # to retag image as dogfood
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -142,7 +142,7 @@ jobs:
     needs: deploy
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 

.github/workflows/docker-base.yaml

@@ -38,7 +38,7 @@ jobs:
     if: github.repository_owner == 'coder'
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 

.github/workflows/dogfood.yaml

@@ -26,7 +26,7 @@ jobs:
     runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-4' || 'ubuntu-latest' }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -125,7 +125,7 @@ jobs:
       id-token: write
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 

.github/workflows/linear-release.yaml

@@ -5,8 +5,6 @@ on:
     branches:
       - main
       - "release/2.[0-9]+"
-  release:
-    types: [published]
 
 permissions:
   contents: read
@@ -29,9 +27,9 @@ jobs:
 
       - name: Detect next release version
         id: version
-        # Find the highest release/2.X branch (exact pattern, no suffixes like
-        # release/2.31_hotfix) and derive the next minor version for the release
-        # currently in development on main.
+        # Find the highest release/2.X branch (exact pattern, no suffixes
+        # like release/2.31_hotfix) and derive the next minor version for
+        # the release currently in development on main.
         run: |
           LATEST_MINOR=$(git branch -r | grep -E '^\s*origin/release/2\.[0-9]+$' | \
             sed 's/.*release\/2\.//' | sort -n | tail -1)
@@ -40,8 +38,10 @@ jobs:
             echo "skip=true" >> "$GITHUB_OUTPUT"
             exit 0
           fi
-          echo "version=2.$((LATEST_MINOR + 1))" >> "$GITHUB_OUTPUT"
+          NEXT="2.$((LATEST_MINOR + 1))"
+          echo "version=$NEXT" >> "$GITHUB_OUTPUT"
           echo "skip=false" >> "$GITHUB_OUTPUT"
+          echo "Detected next release: $NEXT"
 
       - name: Sync issues
         id: sync
@@ -51,6 +51,7 @@ jobs:
           access_key: ${{ secrets.LINEAR_ACCESS_KEY }}
           command: sync
           version: ${{ steps.version.outputs.version }}
+          name: ${{ steps.version.outputs.version }}
           timeout: 300
 
   sync-release-branch:
@@ -76,6 +77,7 @@ jobs:
           access_key: ${{ secrets.LINEAR_ACCESS_KEY }}
           command: sync
           version: ${{ steps.version.outputs.version }}
+          name: ${{ steps.version.outputs.version }}
           timeout: 300
 
   code-freeze:
@@ -106,38 +108,3 @@ jobs:
           version: ${{ steps.version.outputs.version }}
           timeout: 300
 
-  complete:
-    name: Complete Linear release
-    if: github.event_name == 'release'
-    runs-on: ubuntu-latest
-    steps:
-      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
-        with:
-          persist-credentials: false
-
-      - name: Extract release version
-        id: version
-        # Strip "v" prefix and patch: "v2.31.0" -> "2.31". Also detect whether
-        # this is a minor release (v*.*.0) — patch releases (v2.31.1, v2.31.2,
-        # ...) are grouped into the same Linear release and must not re-complete
-        # it after it has already shipped.
-        run: |
-          VERSION=$(echo "$TAG" | sed 's/^v//' | cut -d. -f1,2)
-          echo "version=$VERSION" >> "$GITHUB_OUTPUT"
-          if [[ "$TAG" =~ ^v[0-9]+\.[0-9]+\.0$ ]]; then
-            echo "is_minor=true" >> "$GITHUB_OUTPUT"
-          else
-            echo "is_minor=false" >> "$GITHUB_OUTPUT"
-          fi
-        env:
-          TAG: ${{ github.event.release.tag_name }}
-
-      - name: Complete release
-        id: complete
-        if: steps.version.outputs.is_minor == 'true'
-        uses: linear/linear-release-action@755d50b5adb7dd42b976ee9334952745d62ceb2d # v0.6.0
-        with:
-          access_key: ${{ secrets.LINEAR_ACCESS_KEY }}
-          command: complete
-          version: ${{ steps.version.outputs.version }}
-          timeout: 300

.github/workflows/nightly-gauntlet.yaml

@@ -28,7 +28,7 @@ jobs:
           - windows-2022
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 

.github/workflows/pr-auto-assign.yaml

@@ -15,7 +15,7 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 

.github/workflows/pr-cherry-pick-check.yaml

@@ -0,0 +1,93 @@
+# Ensures that only bug fixes are cherry-picked to release branches.
+# PRs targeting release/* must have a title starting with "fix:" or "fix(scope):".
+name: PR Cherry-Pick Check
+
+on:
+  # zizmor: ignore[dangerous-triggers] Only reads PR metadata and comments; does not checkout PR code.
+  pull_request_target:
+    types: [opened, reopened, edited]
+    branches:
+      - "release/*"
+
+permissions:
+  pull-requests: write
+
+jobs:
+  check-cherry-pick:
+    runs-on: ubuntu-latest
+    steps:
+      - name: Harden Runner
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
+        with:
+          egress-policy: audit
+
+      - name: Check PR title for bug fix
+        uses: actions/github-script@60a0d83039c74a4aee543508d2ffcb1c3799cdea # v7.0.1
+        with:
+          script: |
+            const title = context.payload.pull_request.title;
+            const prNumber = context.payload.pull_request.number;
+            const baseBranch = context.payload.pull_request.base.ref;
+            const author = context.payload.pull_request.user.login;
+
+            console.log(`PR #${prNumber}: "${title}" -> ${baseBranch}`);
+
+            // Match conventional commit "fix:" or "fix(scope):" prefix.
+            const isBugFix = /^fix(\(.+\))?:/.test(title);
+
+            if (isBugFix) {
+              console.log("PR title indicates a bug fix. No action needed.");
+              return;
+            }
+
+            console.log("PR title does not indicate a bug fix. Commenting.");
+
+            // Check for an existing comment from this bot to avoid duplicates
+            // on title edits.
+            const { data: comments } = await github.rest.issues.listComments({
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+              issue_number: prNumber,
+            });
+
+            const marker = "<!-- cherry-pick-check -->";
+            const existingComment = comments.find(
+              (c) => c.body && c.body.includes(marker),
+            );
+
+            const body = [
+              marker,
+              `👋 Hey @${author}!`,
+              "",
+              `This PR is targeting the \`${baseBranch}\` release branch, but its title does not start with \`fix:\` or \`fix(scope):\`.`,
+              "",
+              "Only **bug fixes** should be cherry-picked to release branches. If this is a bug fix, please update the PR title to match the conventional commit format:",
+              "",
+              "```",
+              "fix: description of the bug fix",
+              "fix(scope): description of the bug fix",
+              "```",
+              "",
+              "If this is **not** a bug fix, it likely should not target a release branch.",
+            ].join("\n");
+
+            if (existingComment) {
+              console.log(`Updating existing comment ${existingComment.id}.`);
+              await github.rest.issues.updateComment({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                comment_id: existingComment.id,
+                body,
+              });
+            } else {
+              await github.rest.issues.createComment({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                issue_number: prNumber,
+                body,
+              });
+            }
+
+            core.warning(
+              `PR #${prNumber} targets ${baseBranch} but is not a bug fix. Title must start with "fix:" or "fix(scope):".`,
+            );

.github/workflows/pr-cleanup.yaml

@@ -19,7 +19,7 @@ jobs:
       packages: write
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 

.github/workflows/pr-deploy.yaml

@@ -39,7 +39,7 @@ jobs:
       PR_OPEN: ${{ steps.check_pr.outputs.pr_open }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -76,7 +76,7 @@ jobs:
     runs-on: "ubuntu-latest"
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -184,7 +184,7 @@ jobs:
       pull-requests: write # needed for commenting on PRs
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -228,7 +228,7 @@ jobs:
       CODER_IMAGE_TAG: ${{ needs.get_info.outputs.CODER_IMAGE_TAG }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -288,7 +288,7 @@ jobs:
       PR_HOSTNAME: "pr${{ needs.get_info.outputs.PR_NUMBER }}.${{ secrets.PR_DEPLOYMENTS_DOMAIN }}"
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 

.github/workflows/release-validation.yaml

@@ -14,7 +14,7 @@ jobs:
 
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 

.github/workflows/release.yaml

@@ -9,6 +9,7 @@ on:
         options:
           - mainline
           - stable
+          - rc
       release_notes:
         description: Release notes for the publishing the release. This is required to create a release.
       dry_run:
@@ -80,7 +81,7 @@ jobs:
       version: ${{ steps.version.outputs.version }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -119,13 +120,23 @@ jobs:
             exit 1
           fi
 
-          # 2.10.2 -> release/2.10
+          # Derive the release branch from the version tag.
+          # Non-RC releases must be on a release/X.Y branch.
+          # RC tags are allowed on any branch (typically main).
           version="$(./scripts/version.sh)"
-          release_branch=release/${version%.*}
-          branch_contains_tag=$(git branch --remotes --contains "${GITHUB_REF}" --list "*/${release_branch}" --format='%(refname)')
-          if [[ -z "${branch_contains_tag}" ]]; then
-            echo "Ref tag must exist in a branch named ${release_branch} when creating a release, did you use scripts/release.sh?"
-            exit 1
+          # Strip any pre-release suffix first (e.g. 2.32.0-rc.0 -> 2.32.0)
+          base_version="${version%%-*}"
+          # Then strip patch to get major.minor (e.g. 2.32.0 -> 2.32)
+          release_branch="release/${base_version%.*}"
+
+          if [[ "$version" == *-rc.* ]]; then
+            echo "RC release detected — skipping release branch check (RC tags are cut from main)."
+          else
+            branch_contains_tag=$(git branch --remotes --contains "${GITHUB_REF}" --list "*/${release_branch}" --format='%(refname)')
+            if [[ -z "${branch_contains_tag}" ]]; then
+              echo "Ref tag must exist in a branch named ${release_branch} when creating a non-RC release, did you use scripts/release.sh?"
+              exit 1
+            fi
           fi
 
           if [[ -z "${CODER_RELEASE_NOTES}" ]]; then
@@ -531,6 +542,9 @@ jobs:
           if [[ $CODER_RELEASE_CHANNEL == "stable" ]]; then
             publish_args+=(--stable)
           fi
+          if [[ $CODER_RELEASE_CHANNEL == "rc" ]]; then
+            publish_args+=(--rc)
+          fi
           if [[ $CODER_DRY_RUN == *t* ]]; then
             publish_args+=(--dry-run)
           fi
@@ -563,6 +577,35 @@ jobs:
           VERSION: ${{ steps.version.outputs.version }}
           CREATED_LATEST_TAG: ${{ steps.build_docker.outputs.created_latest_tag }}
 
+      # Mark the Linear release as shipped.
+      - name: Extract Linear release version
+        if: ${{ !inputs.dry_run }}
+        id: linear_version
+        run: |
+          # Skip RC releases — they must not complete the Linear release.
+          if [[ "$VERSION" == *-rc* ]]; then
+            echo "RC release (${VERSION}), skipping Linear release completion."
+            echo "skip=true" >> "$GITHUB_OUTPUT"
+            exit 0
+          fi
+          # Strip patch to get the Linear release version (e.g. 2.32.0 -> 2.32).
+          linear_version=$(echo "$VERSION" | cut -d. -f1,2)
+          echo "version=$linear_version" >> "$GITHUB_OUTPUT"
+          echo "skip=false" >> "$GITHUB_OUTPUT"
+          echo "Completing Linear release ${linear_version}"
+        env:
+          VERSION: ${{ steps.version.outputs.version }}
+
+      - name: Complete Linear release
+        if: ${{ !inputs.dry_run && steps.linear_version.outputs.skip != 'true' }}
+        continue-on-error: true
+        uses: linear/linear-release-action@755d50b5adb7dd42b976ee9334952745d62ceb2d # v0.6.0
+        with:
+          access_key: ${{ secrets.LINEAR_ACCESS_KEY }}
+          command: complete
+          version: ${{ steps.linear_version.outputs.version }}
+          timeout: 300
+
       - name: Authenticate to Google Cloud
         uses: google-github-actions/auth@7c6bc770dae815cd3e89ee6cdf493a5fab2cc093 # v3.0.0
         with:
@@ -614,7 +657,7 @@ jobs:
           retention-days: 7
 
       - name: Send repository-dispatch event
-        if: ${{ !inputs.dry_run }}
+        if: ${{ !inputs.dry_run && inputs.release_channel != 'rc' }}
         uses: peter-evans/repository-dispatch@28959ce8df70de7be546dd1250a005dd32156697 # v4.0.1
         with:
           token: ${{ secrets.CDRCI_GITHUB_TOKEN }}
@@ -630,7 +673,7 @@ jobs:
 
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -702,11 +745,11 @@ jobs:
     name: Publish to winget-pkgs
     runs-on: windows-latest
     needs: release
-    if: ${{ !inputs.dry_run }}
+    if: ${{ !inputs.dry_run && inputs.release_channel != 'rc' }}
 
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 

.github/workflows/scorecard.yml

@@ -20,7 +20,7 @@ jobs:
 
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -47,6 +47,6 @@ jobs:
 
       # Upload the results to GitHub's code scanning dashboard.
       - name: "Upload to code-scanning"
-        uses: github/codeql-action/upload-sarif@5d4e8d1aca955e8d8589aabd499c5cae939e33c7 # v3.29.5
+        uses: github/codeql-action/upload-sarif@c10b8064de6f491fea524254123dbe5e09572f13 # v3.29.5
         with:
           sarif_file: results.sarif

.github/workflows/security.yaml

@@ -27,7 +27,7 @@ jobs:
     runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -40,7 +40,7 @@ jobs:
         uses: ./.github/actions/setup-go
 
       - name: Initialize CodeQL
-        uses: github/codeql-action/init@5d4e8d1aca955e8d8589aabd499c5cae939e33c7 # v3.29.5
+        uses: github/codeql-action/init@c10b8064de6f491fea524254123dbe5e09572f13 # v3.29.5
         with:
           languages: go, javascript
 
@@ -50,7 +50,7 @@ jobs:
           rm Makefile
 
       - name: Perform CodeQL Analysis
-        uses: github/codeql-action/analyze@5d4e8d1aca955e8d8589aabd499c5cae939e33c7 # v3.29.5
+        uses: github/codeql-action/analyze@c10b8064de6f491fea524254123dbe5e09572f13 # v3.29.5
 
       - name: Send Slack notification on failure
         if: ${{ failure() }}

.github/workflows/stale.yaml

@@ -18,7 +18,7 @@ jobs:
       pull-requests: write
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -96,7 +96,7 @@ jobs:
       contents: write
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -120,7 +120,7 @@ jobs:
       actions: write
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 

.github/workflows/typos.toml

@@ -36,6 +36,7 @@ typ = "typ"
 styl = "styl"
 edn = "edn"
 Inferrable = "Inferrable"
+IIF = "IIF"
 
 [files]
 extend-exclude = [

.github/workflows/weekly-docs.yaml

@@ -21,7 +21,7 @@ jobs:
       pull-requests: write # required to post PR review comments by the action
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -49,8 +49,10 @@ jobs:
       # TODO: Remove this workaround once action-linkspector sets
       # package-manager-cache: false in its internal setup-node step.
       # See: https://github.com/UmbrellaDocs/action-linkspector/issues/54
-      - name: Enable corepack
-        run: corepack enable pnpm
+      - name: Enable corepack and create pnpm store
+        run: |
+          corepack enable pnpm
+          mkdir -p "$(pnpm store path --silent)"
 
       - name: Check Markdown links
         uses: umbrelladocs/action-linkspector@37c85bcde51b30bf929936502bac6bfb7e8f0a4d # v1.4.1

.gitignore

@@ -103,3 +103,6 @@ PLAN.md
 
 # Ignore any dev licenses
 license.txt
+-e 
+# Agent planning documents (local working files).
+docs/plans/

AGENTS.md

@@ -110,6 +110,9 @@ app, err := api.Database.GetOAuth2ProviderAppByClientID(ctx, clientID)
 - For experimental or unstable API paths, skip public doc generation with
   `// @x-apidocgen {"skip": true}` after the `@Router` annotation. This
   keeps them out of the published API reference until they stabilize.
+- Experimental chat endpoints in `coderd/exp_chats.go` omit swagger
+  annotations entirely. Do not add `@Summary`, `@Router`, or other
+  swagger comments to handlers in that file.
 
 ### Database Query Naming
 

Makefile

@@ -91,6 +91,59 @@ define atomic_write
 		mv "$$tmpfile" "$@" && rm -rf "$$tmpdir"
 endef
 
+# Helper binary targets. Built with go build -o to avoid caching
+# link-stage executables in GOCACHE. Each binary is a real Make
+# target so parallel -j builds serialize correctly instead of
+# racing on the same output path.
+
+_gen/bin/apitypings: $(wildcard scripts/apitypings/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/apitypings
+
+_gen/bin/auditdocgen: $(wildcard scripts/auditdocgen/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/auditdocgen
+
+_gen/bin/check-scopes: $(wildcard scripts/check-scopes/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/check-scopes
+
+_gen/bin/clidocgen: $(wildcard scripts/clidocgen/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/clidocgen
+
+_gen/bin/dbdump: $(wildcard coderd/database/gen/dump/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./coderd/database/gen/dump
+
+_gen/bin/examplegen: $(wildcard scripts/examplegen/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/examplegen
+
+_gen/bin/gensite: $(wildcard scripts/gensite/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/gensite
+
+_gen/bin/apikeyscopesgen: $(wildcard scripts/apikeyscopesgen/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/apikeyscopesgen
+
+_gen/bin/metricsdocgen: $(wildcard scripts/metricsdocgen/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/metricsdocgen
+
+_gen/bin/metricsdocgen-scanner: $(wildcard scripts/metricsdocgen/scanner/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/metricsdocgen/scanner
+
+_gen/bin/modeloptionsgen: $(wildcard scripts/modeloptionsgen/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/modeloptionsgen
+
+_gen/bin/typegen: $(wildcard scripts/typegen/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/typegen
+
 # Shared temp directory for atomic writes. Lives at the project root
 # so all targets share the same filesystem, and is gitignored.
 # Order-only prerequisite: recipes that need it depend on | _gen
@@ -201,6 +254,7 @@ endif
 
 clean:
 	rm -rf build/ site/build/ site/out/
+	rm -rf _gen/bin
 	mkdir -p build/
 	git restore site/out/
 .PHONY: clean
@@ -654,8 +708,8 @@ lint/go:
 	go tool github.com/coder/paralleltestctx/cmd/paralleltestctx -custom-funcs="testutil.Context" ./...
 .PHONY: lint/go
 
-lint/examples:
-	go run ./scripts/examplegen/main.go -lint
+lint/examples: | _gen/bin/examplegen
+	_gen/bin/examplegen -lint
 .PHONY: lint/examples
 
 # Use shfmt to determine the shell files, takes editorconfig into consideration.
@@ -693,8 +747,8 @@ lint/actions/zizmor:
 .PHONY: lint/actions/zizmor
 
 # Verify api_key_scope enum contains all RBAC <resource>:<action> values.
-lint/check-scopes: coderd/database/dump.sql
-	go run ./scripts/check-scopes
+lint/check-scopes: coderd/database/dump.sql | _gen/bin/check-scopes
+	_gen/bin/check-scopes
 .PHONY: lint/check-scopes
 
 # Verify migrations do not hardcode the public schema.
@@ -734,8 +788,8 @@ lint/typos: build/typos-$(TYPOS_VERSION)
 # The pre-push hook is allowlisted, see scripts/githooks/pre-push.
 #
 # pre-commit uses two phases: gen+fmt first, then lint+build. This
-# avoids races where gen's `go run` creates temporary .go files that
-# lint's find-based checks pick up. Within each phase, targets run in
+# avoids races where gen creates temporary .go files that lint's
+# find-based checks pick up. Within each phase, targets run in
 # parallel via -j. It fails if any tracked files have unstaged
 # changes afterward.
 
@@ -949,8 +1003,8 @@ gen/mark-fresh:
 
 # Runs migrations to output a dump of the database schema after migrations are
 # applied.
-coderd/database/dump.sql: coderd/database/gen/dump/main.go $(wildcard coderd/database/migrations/*.sql)
-	go run ./coderd/database/gen/dump/main.go
+coderd/database/dump.sql: coderd/database/gen/dump/main.go $(wildcard coderd/database/migrations/*.sql) | _gen/bin/dbdump
+	_gen/bin/dbdump
 	touch "$@"
 
 # Generates Go code for querying the database.
@@ -988,6 +1042,7 @@ coderd/httpmw/loggermw/loggermock/loggermock.go: coderd/httpmw/loggermw/logger.g
 
 codersdk/workspacesdk/agentconnmock/agentconnmock.go: codersdk/workspacesdk/agentconn.go
 	go generate ./codersdk/workspacesdk/agentconnmock/
+	./scripts/format_go_file.sh "$@"
 	touch "$@"
 
 $(AIBRIDGED_MOCKS): enterprise/aibridged/client.go enterprise/aibridged/pool.go
@@ -1066,88 +1121,88 @@ enterprise/aibridged/proto/aibridged.pb.go: enterprise/aibridged/proto/aibridged
 		--go-drpc_opt=paths=source_relative \
 		./enterprise/aibridged/proto/aibridged.proto
 
-site/src/api/typesGenerated.ts: site/node_modules/.installed $(wildcard scripts/apitypings/*) $(shell find ./codersdk $(FIND_EXCLUSIONS) -type f -name '*.go') | _gen
-	$(call atomic_write,go run -C ./scripts/apitypings main.go,./scripts/biome_format.sh)
+site/src/api/typesGenerated.ts: site/node_modules/.installed $(wildcard scripts/apitypings/*) $(shell find ./codersdk $(FIND_EXCLUSIONS) -type f -name '*.go') | _gen _gen/bin/apitypings
+	$(call atomic_write,_gen/bin/apitypings,./scripts/biome_format.sh)
 
 site/e2e/provisionerGenerated.ts: site/node_modules/.installed provisionerd/proto/provisionerd.pb.go provisionersdk/proto/provisioner.pb.go
 	(cd site/ && pnpm run gen:provisioner)
 	touch "$@"
 
-site/src/theme/icons.json: site/node_modules/.installed $(wildcard scripts/gensite/*) $(wildcard site/static/icon/*) | _gen
+site/src/theme/icons.json: site/node_modules/.installed $(wildcard scripts/gensite/*) $(wildcard site/static/icon/*) | _gen _gen/bin/gensite
 	tmpdir=$$(mktemp -d -p _gen) && tmpfile=$$(realpath "$$tmpdir")/$(notdir $@) && \
-		go run ./scripts/gensite/ -icons "$$tmpfile" && \
+		_gen/bin/gensite -icons "$$tmpfile" && \
 		./scripts/biome_format.sh "$$tmpfile" && \
 		mv "$$tmpfile" "$@" && rm -rf "$$tmpdir"
 
-examples/examples.gen.json: scripts/examplegen/main.go examples/examples.go $(shell find ./examples/templates) | _gen
-	$(call atomic_write,go run ./scripts/examplegen/main.go)
+examples/examples.gen.json: scripts/examplegen/main.go examples/examples.go $(shell find ./examples/templates) | _gen _gen/bin/examplegen
+	$(call atomic_write,_gen/bin/examplegen)
 
-coderd/rbac/object_gen.go: scripts/typegen/rbacobject.gotmpl scripts/typegen/main.go coderd/rbac/object.go coderd/rbac/policy/policy.go | _gen
-	$(call atomic_write,go run ./scripts/typegen/main.go rbac object)
+coderd/rbac/object_gen.go: scripts/typegen/rbacobject.gotmpl scripts/typegen/main.go coderd/rbac/object.go coderd/rbac/policy/policy.go | _gen _gen/bin/typegen
+	$(call atomic_write,_gen/bin/typegen rbac object)
 	touch "$@"
 
-# NOTE: depends on object_gen.go because `go run` compiles
-# coderd/rbac which includes it.
+# NOTE: depends on object_gen.go because the generator build
+# compiles coderd/rbac which includes it.
 coderd/rbac/scopes_constants_gen.go: scripts/typegen/scopenames.gotmpl scripts/typegen/main.go coderd/rbac/policy/policy.go \
-	coderd/rbac/object_gen.go | _gen
+	coderd/rbac/object_gen.go | _gen _gen/bin/typegen
 	# Write to a temp file first to avoid truncating the package
 	# during build since the generator imports the rbac package.
-	$(call atomic_write,go run ./scripts/typegen/main.go rbac scopenames)
+	$(call atomic_write,_gen/bin/typegen rbac scopenames)
 	touch "$@"
 
 # NOTE: depends on object_gen.go and scopes_constants_gen.go because
-# `go run` compiles coderd/rbac which includes both.
+# the generator build compiles coderd/rbac which includes both.
 codersdk/rbacresources_gen.go: scripts/typegen/codersdk.gotmpl scripts/typegen/main.go coderd/rbac/object.go coderd/rbac/policy/policy.go \
-	coderd/rbac/object_gen.go coderd/rbac/scopes_constants_gen.go | _gen
+	coderd/rbac/object_gen.go coderd/rbac/scopes_constants_gen.go | _gen _gen/bin/typegen
 	# Write to a temp file to avoid truncating the target, which
 	# would break the codersdk package and any parallel build targets.
-	$(call atomic_write,go run scripts/typegen/main.go rbac codersdk)
+	$(call atomic_write,_gen/bin/typegen rbac codersdk)
 	touch "$@"
 
 # NOTE: depends on object_gen.go and scopes_constants_gen.go because
-# `go run` compiles coderd/rbac which includes both.
+# the generator build compiles coderd/rbac which includes both.
 codersdk/apikey_scopes_gen.go: scripts/apikeyscopesgen/main.go coderd/rbac/scopes_catalog.go coderd/rbac/scopes.go \
-	coderd/rbac/object_gen.go coderd/rbac/scopes_constants_gen.go | _gen
+	coderd/rbac/object_gen.go coderd/rbac/scopes_constants_gen.go | _gen _gen/bin/apikeyscopesgen
 	# Generate SDK constants for external API key scopes.
-	$(call atomic_write,go run ./scripts/apikeyscopesgen)
+	$(call atomic_write,_gen/bin/apikeyscopesgen)
 	touch "$@"
 
 # NOTE: depends on object_gen.go and scopes_constants_gen.go because
-# `go run` compiles coderd/rbac which includes both.
+# the generator build compiles coderd/rbac which includes both.
 site/src/api/rbacresourcesGenerated.ts: site/node_modules/.installed scripts/typegen/codersdk.gotmpl scripts/typegen/main.go coderd/rbac/object.go coderd/rbac/policy/policy.go \
-	coderd/rbac/object_gen.go coderd/rbac/scopes_constants_gen.go | _gen
-	$(call atomic_write,go run scripts/typegen/main.go rbac typescript,./scripts/biome_format.sh)
+	coderd/rbac/object_gen.go coderd/rbac/scopes_constants_gen.go | _gen _gen/bin/typegen
+	$(call atomic_write,_gen/bin/typegen rbac typescript,./scripts/biome_format.sh)
 
-site/src/api/countriesGenerated.ts: site/node_modules/.installed scripts/typegen/countries.tstmpl scripts/typegen/main.go codersdk/countries.go | _gen
-	$(call atomic_write,go run scripts/typegen/main.go countries,./scripts/biome_format.sh)
+site/src/api/countriesGenerated.ts: site/node_modules/.installed scripts/typegen/countries.tstmpl scripts/typegen/main.go codersdk/countries.go | _gen _gen/bin/typegen
+	$(call atomic_write,_gen/bin/typegen countries,./scripts/biome_format.sh)
 
-site/src/api/chatModelOptionsGenerated.json: scripts/modeloptionsgen/main.go codersdk/chats.go | _gen
-	$(call atomic_write,go run ./scripts/modeloptionsgen/main.go | tail -n +2,./scripts/biome_format.sh)
+site/src/api/chatModelOptionsGenerated.json: scripts/modeloptionsgen/main.go codersdk/chats.go | _gen _gen/bin/modeloptionsgen
+	$(call atomic_write,_gen/bin/modeloptionsgen | tail -n +2,./scripts/biome_format.sh)
 
-scripts/metricsdocgen/generated_metrics: $(GO_SRC_FILES) | _gen
-	$(call atomic_write,go run ./scripts/metricsdocgen/scanner)
+scripts/metricsdocgen/generated_metrics: $(GO_SRC_FILES) | _gen _gen/bin/metricsdocgen-scanner
+	$(call atomic_write,_gen/bin/metricsdocgen-scanner)
 
-docs/admin/integrations/prometheus.md: node_modules/.installed scripts/metricsdocgen/main.go scripts/metricsdocgen/metrics scripts/metricsdocgen/generated_metrics | _gen
+docs/admin/integrations/prometheus.md: node_modules/.installed scripts/metricsdocgen/main.go scripts/metricsdocgen/metrics scripts/metricsdocgen/generated_metrics | _gen _gen/bin/metricsdocgen
 	tmpdir=$$(mktemp -d -p _gen) && tmpfile=$$(realpath "$$tmpdir")/$(notdir $@) && cp "$@" "$$tmpfile" && \
-		go run scripts/metricsdocgen/main.go --prometheus-doc-file="$$tmpfile" && \
+		_gen/bin/metricsdocgen --prometheus-doc-file="$$tmpfile" && \
 		pnpm exec markdownlint-cli2 --fix "$$tmpfile" && \
 		pnpm exec markdown-table-formatter "$$tmpfile" && \
 		mv "$$tmpfile" "$@" && rm -rf "$$tmpdir"
 
-docs/reference/cli/index.md: node_modules/.installed scripts/clidocgen/main.go examples/examples.gen.json $(GO_SRC_FILES) | _gen
+docs/reference/cli/index.md: node_modules/.installed scripts/clidocgen/main.go examples/examples.gen.json $(GO_SRC_FILES) | _gen _gen/bin/clidocgen
 	tmpdir=$$(mktemp -d -p _gen) && \
 		tmpdir=$$(realpath "$$tmpdir") && \
 		mkdir -p "$$tmpdir/docs/reference/cli" && \
 		cp docs/manifest.json "$$tmpdir/docs/manifest.json" && \
-		CI=true DOCS_DIR="$$tmpdir/docs" go run ./scripts/clidocgen && \
+		CI=true DOCS_DIR="$$tmpdir/docs" _gen/bin/clidocgen && \
 		pnpm exec markdownlint-cli2 --fix "$$tmpdir/docs/reference/cli/*.md" && \
 		pnpm exec markdown-table-formatter "$$tmpdir/docs/reference/cli/*.md" && \
 		for f in "$$tmpdir/docs/reference/cli/"*.md; do mv "$$f" "docs/reference/cli/$$(basename "$$f")"; done && \
 		rm -rf "$$tmpdir"
 
-docs/admin/security/audit-logs.md: node_modules/.installed coderd/database/querier.go scripts/auditdocgen/main.go enterprise/audit/table.go coderd/rbac/object_gen.go | _gen
+docs/admin/security/audit-logs.md: node_modules/.installed coderd/database/querier.go scripts/auditdocgen/main.go enterprise/audit/table.go coderd/rbac/object_gen.go | _gen _gen/bin/auditdocgen
 	tmpdir=$$(mktemp -d -p _gen) && tmpfile=$$(realpath "$$tmpdir")/$(notdir $@) && cp "$@" "$$tmpfile" && \
-		go run scripts/auditdocgen/main.go --audit-doc-file="$$tmpfile" && \
+		_gen/bin/auditdocgen --audit-doc-file="$$tmpfile" && \
 		pnpm exec markdownlint-cli2 --fix "$$tmpfile" && \
 		pnpm exec markdown-table-formatter "$$tmpfile" && \
 		mv "$$tmpfile" "$@" && rm -rf "$$tmpdir"

agent/agent.go

@@ -38,6 +38,7 @@ import (
 	"cdr.dev/slog/v3"
 	"github.com/coder/clistat"
 	"github.com/coder/coder/v2/agent/agentcontainers"
+	"github.com/coder/coder/v2/agent/agentcontextconfig"
 	"github.com/coder/coder/v2/agent/agentexec"
 	"github.com/coder/coder/v2/agent/agentfiles"
 	"github.com/coder/coder/v2/agent/agentgit"
@@ -101,6 +102,8 @@ type Options struct {
 	ReportMetadataInterval       time.Duration
 	ServiceBannerRefreshInterval time.Duration
 	BlockFileTransfer            bool
+	BlockReversePortForwarding   bool
+	BlockLocalPortForwarding     bool
 	Execer                       agentexec.Execer
 	Devcontainers                bool
 	DevcontainerAPIOptions       []agentcontainers.Option // Enable Devcontainers for these to be effective.
@@ -213,6 +216,8 @@ func New(options Options) Agent {
 		subsystems:                         options.Subsystems,
 		logSender:                          agentsdk.NewLogSender(options.Logger),
 		blockFileTransfer:                  options.BlockFileTransfer,
+		blockReversePortForwarding:         options.BlockReversePortForwarding,
+		blockLocalPortForwarding:           options.BlockLocalPortForwarding,
 
 		prometheusRegistry: prometheusRegistry,
 		metrics:            newAgentMetrics(prometheusRegistry),
@@ -279,6 +284,8 @@ type agent struct {
 	sshServer                          *agentssh.Server
 	sshMaxTimeout                      time.Duration
 	blockFileTransfer                  bool
+	blockReversePortForwarding         bool
+	blockLocalPortForwarding           bool
 
 	lifecycleUpdate            chan struct{}
 	lifecycleReported          chan codersdk.WorkspaceAgentLifecycle
@@ -308,12 +315,13 @@ type agent struct {
 	containerAPI        *agentcontainers.API
 	gitAPIOptions       []agentgit.Option
 
-	filesAPI   *agentfiles.API
-	gitAPI     *agentgit.API
-	processAPI *agentproc.API
-	desktopAPI *agentdesktop.API
-	mcpManager *agentmcp.Manager
-	mcpAPI     *agentmcp.API
+	filesAPI         *agentfiles.API
+	gitAPI           *agentgit.API
+	processAPI       *agentproc.API
+	desktopAPI       *agentdesktop.API
+	mcpManager       *agentmcp.Manager
+	mcpAPI           *agentmcp.API
+	contextConfigAPI *agentcontextconfig.API
 
 	socketServerEnabled bool
 	socketPath          string
@@ -329,12 +337,14 @@ func (a *agent) TailnetConn() *tailnet.Conn {
 func (a *agent) init() {
 	// pass the "hard" context because we explicitly close the SSH server as part of graceful shutdown.
 	sshSrv, err := agentssh.NewServer(a.hardCtx, a.logger.Named("ssh-server"), a.prometheusRegistry, a.filesystem, a.execer, &agentssh.Config{
-		MaxTimeout:          a.sshMaxTimeout,
-		MOTDFile:            func() string { return a.manifest.Load().MOTDFile },
-		AnnouncementBanners: func() *[]codersdk.BannerConfig { return a.announcementBanners.Load() },
-		UpdateEnv:           a.updateCommandEnv,
-		WorkingDirectory:    func() string { return a.manifest.Load().Directory },
-		BlockFileTransfer:   a.blockFileTransfer,
+		MaxTimeout:                 a.sshMaxTimeout,
+		MOTDFile:                   func() string { return a.manifest.Load().MOTDFile },
+		AnnouncementBanners:        func() *[]codersdk.BannerConfig { return a.announcementBanners.Load() },
+		UpdateEnv:                  a.updateCommandEnv,
+		WorkingDirectory:           func() string { return a.manifest.Load().Directory },
+		BlockFileTransfer:          a.blockFileTransfer,
+		BlockReversePortForwarding: a.blockReversePortForwarding,
+		BlockLocalPortForwarding:   a.blockLocalPortForwarding,
 		ReportConnection: func(id uuid.UUID, magicType agentssh.MagicSessionType, ip string) func(code int, reason string) {
 			var connectionType proto.Connection_Type
 			switch magicType {
@@ -396,11 +406,17 @@ func (a *agent) init() {
 	gitOpts := append([]agentgit.Option{agentgit.WithClock(a.clock)}, a.gitAPIOptions...)
 	a.gitAPI = agentgit.NewAPI(a.logger.Named("git"), pathStore, gitOpts...)
 	desktop := agentdesktop.NewPortableDesktop(
-		a.logger.Named("desktop"), a.execer, a.scriptRunner.ScriptBinDir(),
+		a.logger.Named("desktop"), a.execer, a.scriptRunner.ScriptBinDir(), nil,
 	)
 	a.desktopAPI = agentdesktop.NewAPI(a.logger.Named("desktop"), desktop, a.clock)
 	a.mcpManager = agentmcp.NewManager(a.logger.Named("mcp"))
 	a.mcpAPI = agentmcp.NewAPI(a.logger.Named("mcp"), a.mcpManager)
+	a.contextConfigAPI = agentcontextconfig.NewAPI(func() string {
+		if m := a.manifest.Load(); m != nil {
+			return m.Directory
+		}
+		return ""
+	})
 	a.reconnectingPTYServer = reconnectingpty.NewServer(
 		a.logger.Named("reconnecting-pty"),
 		a.sshServer,
@@ -1358,7 +1374,7 @@ func (a *agent) handleManifest(manifestOK *checkpoint) func(ctx context.Context,
 				// lifecycle transition to avoid delaying Ready.
 				// This runs inside the tracked goroutine so it
 				// is properly awaited on shutdown.
-				if mcpErr := a.mcpManager.Connect(a.gracefulCtx, manifest.Directory); mcpErr != nil {
+				if mcpErr := a.mcpManager.Connect(a.gracefulCtx, a.contextConfigAPI.MCPConfigFiles()); mcpErr != nil {
 					a.logger.Warn(ctx, "failed to connect to workspace MCP servers", slog.Error(mcpErr))
 				}
 			})

agent/agent_internal_test.go

@@ -1,6 +1,8 @@
 package agent
 
 import (
+	"path/filepath"
+	"runtime"
 	"testing"
 
 	"github.com/google/uuid"
@@ -8,10 +10,22 @@ import (
 
 	"cdr.dev/slog/v3"
 	"cdr.dev/slog/v3/sloggers/slogtest"
+	"github.com/coder/coder/v2/agent/agentcontextconfig"
 	"github.com/coder/coder/v2/agent/proto"
+	agentsdk "github.com/coder/coder/v2/codersdk/agentsdk"
 	"github.com/coder/coder/v2/testutil"
 )
 
+// platformAbsPath constructs an absolute path that is valid
+// on the current platform. On Windows, paths must include a
+// drive letter to be considered absolute.
+func platformAbsPath(parts ...string) string {
+	if runtime.GOOS == "windows" {
+		return `C:\` + filepath.Join(parts...)
+	}
+	return "/" + filepath.Join(parts...)
+}
+
 // TestReportConnectionEmpty tests that reportConnection() doesn't choke if given an empty IP string, which is what we
 // send if we cannot get the remote address.
 func TestReportConnectionEmpty(t *testing.T) {
@@ -42,3 +56,41 @@ func TestReportConnectionEmpty(t *testing.T) {
 	require.Equal(t, proto.Connection_DISCONNECT, req1.GetConnection().GetAction())
 	require.Equal(t, "because", req1.GetConnection().GetReason())
 }
+
+func TestContextConfigAPI_InitOnce(t *testing.T) {
+	// Not parallel: uses t.Setenv to clear env vars.
+
+	// Clear env vars so defaults are used and the test is
+	// hermetic regardless of the surrounding environment.
+	t.Setenv(agentcontextconfig.EnvInstructionsDirs, "")
+	t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
+	t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
+	t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
+	t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
+
+	// After the fix, contextConfigAPI is set once in init() and
+	// never reassigned. Config() evaluates lazily via the
+	// manifest, so there is no concurrent write to race with.
+	dir1 := platformAbsPath("dir1")
+	dir2 := platformAbsPath("dir2")
+
+	a := &agent{}
+	a.manifest.Store(&agentsdk.Manifest{Directory: dir1})
+	a.contextConfigAPI = agentcontextconfig.NewAPI(func() string {
+		if m := a.manifest.Load(); m != nil {
+			return m.Directory
+		}
+		return ""
+	})
+
+	mcpFiles1 := a.contextConfigAPI.MCPConfigFiles()
+	require.NotEmpty(t, mcpFiles1)
+	require.Contains(t, mcpFiles1[0], dir1)
+
+	// Simulate manifest update on reconnection -- no field
+	// reassignment needed, the lazy closure picks it up.
+	a.manifest.Store(&agentsdk.Manifest{Directory: dir2})
+	mcpFiles2 := a.contextConfigAPI.MCPConfigFiles()
+	require.NotEmpty(t, mcpFiles2)
+	require.Contains(t, mcpFiles2[0], dir2)
+}

agent/agent_test.go

@@ -986,6 +986,161 @@ func TestAgent_TCPRemoteForwarding(t *testing.T) {
 	requireEcho(t, conn)
 }
 
+func TestAgent_TCPLocalForwardingBlocked(t *testing.T) {
+	t.Parallel()
+	ctx := testutil.Context(t, testutil.WaitLong)
+
+	rl, err := net.Listen("tcp", "127.0.0.1:0")
+	require.NoError(t, err)
+	defer rl.Close()
+	tcpAddr, valid := rl.Addr().(*net.TCPAddr)
+	require.True(t, valid)
+	remotePort := tcpAddr.Port
+
+	//nolint:dogsled
+	agentConn, _, _, _, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, o *agent.Options) {
+		o.BlockLocalPortForwarding = true
+	})
+	sshClient, err := agentConn.SSHClient(ctx)
+	require.NoError(t, err)
+	defer sshClient.Close()
+
+	_, err = sshClient.Dial("tcp", fmt.Sprintf("127.0.0.1:%d", remotePort))
+	require.ErrorContains(t, err, "administratively prohibited")
+}
+
+func TestAgent_TCPRemoteForwardingBlocked(t *testing.T) {
+	t.Parallel()
+	ctx := testutil.Context(t, testutil.WaitLong)
+
+	//nolint:dogsled
+	agentConn, _, _, _, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, o *agent.Options) {
+		o.BlockReversePortForwarding = true
+	})
+	sshClient, err := agentConn.SSHClient(ctx)
+	require.NoError(t, err)
+	defer sshClient.Close()
+
+	localhost := netip.MustParseAddr("127.0.0.1")
+	randomPort := testutil.RandomPortNoListen(t)
+	addr := net.TCPAddrFromAddrPort(netip.AddrPortFrom(localhost, randomPort))
+	_, err = sshClient.ListenTCP(addr)
+	require.ErrorContains(t, err, "tcpip-forward request denied by peer")
+}
+
+func TestAgent_UnixLocalForwardingBlocked(t *testing.T) {
+	t.Parallel()
+	if runtime.GOOS == "windows" {
+		t.Skip("unix domain sockets are not fully supported on Windows")
+	}
+	ctx := testutil.Context(t, testutil.WaitLong)
+	tmpdir := testutil.TempDirUnixSocket(t)
+	remoteSocketPath := filepath.Join(tmpdir, "remote-socket")
+
+	l, err := net.Listen("unix", remoteSocketPath)
+	require.NoError(t, err)
+	defer l.Close()
+
+	//nolint:dogsled
+	agentConn, _, _, _, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, o *agent.Options) {
+		o.BlockLocalPortForwarding = true
+	})
+	sshClient, err := agentConn.SSHClient(ctx)
+	require.NoError(t, err)
+	defer sshClient.Close()
+
+	_, err = sshClient.Dial("unix", remoteSocketPath)
+	require.ErrorContains(t, err, "administratively prohibited")
+}
+
+func TestAgent_UnixRemoteForwardingBlocked(t *testing.T) {
+	t.Parallel()
+	if runtime.GOOS == "windows" {
+		t.Skip("unix domain sockets are not fully supported on Windows")
+	}
+	ctx := testutil.Context(t, testutil.WaitLong)
+	tmpdir := testutil.TempDirUnixSocket(t)
+	remoteSocketPath := filepath.Join(tmpdir, "remote-socket")
+
+	//nolint:dogsled
+	agentConn, _, _, _, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, o *agent.Options) {
+		o.BlockReversePortForwarding = true
+	})
+	sshClient, err := agentConn.SSHClient(ctx)
+	require.NoError(t, err)
+	defer sshClient.Close()
+
+	_, err = sshClient.ListenUnix(remoteSocketPath)
+	require.ErrorContains(t, err, "streamlocal-forward@openssh.com request denied by peer")
+}
+
+// TestAgent_LocalBlockedDoesNotAffectReverse verifies that blocking
+// local port forwarding does not prevent reverse port forwarding from
+// working. A field-name transposition at any plumbing hop would cause
+// both directions to be blocked when only one flag is set.
+func TestAgent_LocalBlockedDoesNotAffectReverse(t *testing.T) {
+	t.Parallel()
+	ctx := testutil.Context(t, testutil.WaitLong)
+
+	//nolint:dogsled
+	agentConn, _, _, _, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, o *agent.Options) {
+		o.BlockLocalPortForwarding = true
+	})
+	sshClient, err := agentConn.SSHClient(ctx)
+	require.NoError(t, err)
+	defer sshClient.Close()
+
+	// Reverse forwarding must still work.
+	localhost := netip.MustParseAddr("127.0.0.1")
+	var ll net.Listener
+	for {
+		randomPort := testutil.RandomPortNoListen(t)
+		addr := net.TCPAddrFromAddrPort(netip.AddrPortFrom(localhost, randomPort))
+		ll, err = sshClient.ListenTCP(addr)
+		if err != nil {
+			t.Logf("error remote forwarding: %s", err.Error())
+			select {
+			case <-ctx.Done():
+				t.Fatal("timed out getting random listener")
+			default:
+				continue
+			}
+		}
+		break
+	}
+	_ = ll.Close()
+}
+
+// TestAgent_ReverseBlockedDoesNotAffectLocal verifies that blocking
+// reverse port forwarding does not prevent local port forwarding from
+// working.
+func TestAgent_ReverseBlockedDoesNotAffectLocal(t *testing.T) {
+	t.Parallel()
+	ctx := testutil.Context(t, testutil.WaitLong)
+
+	rl, err := net.Listen("tcp", "127.0.0.1:0")
+	require.NoError(t, err)
+	defer rl.Close()
+	tcpAddr, valid := rl.Addr().(*net.TCPAddr)
+	require.True(t, valid)
+	remotePort := tcpAddr.Port
+	go echoOnce(t, rl)
+
+	//nolint:dogsled
+	agentConn, _, _, _, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, o *agent.Options) {
+		o.BlockReversePortForwarding = true
+	})
+	sshClient, err := agentConn.SSHClient(ctx)
+	require.NoError(t, err)
+	defer sshClient.Close()
+
+	// Local forwarding must still work.
+	conn, err := sshClient.Dial("tcp", fmt.Sprintf("127.0.0.1:%d", remotePort))
+	require.NoError(t, err)
+	defer conn.Close()
+	requireEcho(t, conn)
+}
+
 func TestAgent_UnixLocalForwarding(t *testing.T) {
 	t.Parallel()
 	if runtime.GOOS == "windows" {
@@ -3007,7 +3162,7 @@ func TestAgent_Speedtest(t *testing.T) {
 
 func TestAgent_Reconnect(t *testing.T) {
 	t.Parallel()
-	ctx := testutil.Context(t, testutil.WaitShort)
+	ctx := testutil.Context(t, testutil.WaitLong)
 	logger := testutil.Logger(t)
 	// After the agent is disconnected from a coordinator, it's supposed
 	// to reconnect!
@@ -3020,7 +3175,8 @@ func TestAgent_Reconnect(t *testing.T) {
 		logger,
 		agentID,
 		agentsdk.Manifest{
-			DERPMap: derpMap,
+			DERPMap:   derpMap,
+			Directory: "/test/workspace",
 		},
 		statsCh,
 		fCoordinator,
@@ -3033,13 +3189,19 @@ func TestAgent_Reconnect(t *testing.T) {
 	})
 	defer closer.Close()
 
-	call1 := testutil.RequireReceive(ctx, t, fCoordinator.CoordinateCalls)
-	require.Equal(t, client.GetNumRefreshTokenCalls(), 1)
-	close(call1.Resps) // hang up
-	// expect reconnect
+	// Each iteration forces the agent to reconnect by closing
+	// the current coordinate call while the tracked HTTP server
+	// goroutine (from connection 1's createTailnet) is still
+	// alive, widening the race window.
+	const reconnections = 5
+	for i := range reconnections {
+		call := testutil.RequireReceive(ctx, t, fCoordinator.CoordinateCalls)
+		require.Equal(t, i+1, client.GetNumRefreshTokenCalls())
+		close(call.Resps) // hang up — triggers reconnect
+	}
+	// Verify final reconnect succeeds.
 	testutil.RequireReceive(ctx, t, fCoordinator.CoordinateCalls)
-	// Check that the agent refreshes the token when it reconnects.
-	require.Equal(t, client.GetNumRefreshTokenCalls(), 2)
+	require.Equal(t, reconnections+1, client.GetNumRefreshTokenCalls())
 	closer.Close()
 }
 

agent/agentcontainers/api_test.go

@@ -2862,6 +2862,126 @@ func TestAPI(t *testing.T) {
 			"rebuilt agent should include updated display apps")
 	})
 
+	// Verify that when a terraform-managed subagent is injected into
+	// a devcontainer, the Directory field sent to Create reflects
+	// the container-internal workspaceFolder from devcontainer
+	// read-configuration, not the host-side workspace_folder from
+	// the terraform resource. This is the scenario described in
+	// https://linear.app/codercom/issue/PRODUCT-259:
+	//   1. Non-terraform subagent → directory = /workspaces/foo (correct)
+	//   2. Terraform subagent → directory was stuck on host path (bug)
+	t.Run("TerraformDefinedSubAgentUsesContainerInternalDirectory", func(t *testing.T) {
+		t.Parallel()
+
+		if runtime.GOOS == "windows" {
+			t.Skip("Dev Container tests are not supported on Windows (this test uses mocks but fails due to Windows paths)")
+		}
+
+		var (
+			ctx    = testutil.Context(t, testutil.WaitMedium)
+			logger = slogtest.Make(t, &slogtest.Options{IgnoreErrors: true}).Leveled(slog.LevelDebug)
+			mCtrl  = gomock.NewController(t)
+
+			terraformAgentID = uuid.New()
+			containerID      = "test-container-id"
+
+			// Given: A container with a host-side workspace folder.
+			terraformContainer = codersdk.WorkspaceAgentContainer{
+				ID:           containerID,
+				FriendlyName: "test-container",
+				Image:        "test-image",
+				Running:      true,
+				CreatedAt:    time.Now(),
+				Labels: map[string]string{
+					agentcontainers.DevcontainerLocalFolderLabel: "/home/coder/project",
+					agentcontainers.DevcontainerConfigFileLabel:  "/home/coder/project/.devcontainer/devcontainer.json",
+				},
+			}
+
+			// Given: A terraform-defined devcontainer whose
+			// workspace_folder is the HOST-side path (set by provisioner).
+			terraformDevcontainer = codersdk.WorkspaceAgentDevcontainer{
+				ID:              uuid.New(),
+				Name:            "terraform-devcontainer",
+				WorkspaceFolder: "/home/coder/project",
+				ConfigPath:      "/home/coder/project/.devcontainer/devcontainer.json",
+				SubagentID:      uuid.NullUUID{UUID: terraformAgentID, Valid: true},
+			}
+
+			fCCLI = &fakeContainerCLI{
+				containers: codersdk.WorkspaceAgentListContainersResponse{
+					Containers: []codersdk.WorkspaceAgentContainer{terraformContainer},
+				},
+				arch: runtime.GOARCH,
+			}
+
+			// Given: devcontainer read-configuration returns the
+			// CONTAINER-INTERNAL workspace folder.
+			fDCCLI = &fakeDevcontainerCLI{
+				upID: containerID,
+				readConfig: agentcontainers.DevcontainerConfig{
+					Workspace: agentcontainers.DevcontainerWorkspace{
+						WorkspaceFolder: "/workspaces/project",
+					},
+					MergedConfiguration: agentcontainers.DevcontainerMergedConfiguration{
+						Customizations: agentcontainers.DevcontainerMergedCustomizations{
+							Coder: []agentcontainers.CoderCustomization{{}},
+						},
+					},
+				},
+			}
+
+			mSAC        = acmock.NewMockSubAgentClient(mCtrl)
+			createCalls = make(chan agentcontainers.SubAgent, 1)
+			closed      bool
+		)
+
+		mSAC.EXPECT().List(gomock.Any()).Return([]agentcontainers.SubAgent{}, nil).AnyTimes()
+
+		mSAC.EXPECT().Create(gomock.Any(), gomock.Any()).DoAndReturn(
+			func(_ context.Context, agent agentcontainers.SubAgent) (agentcontainers.SubAgent, error) {
+				agent.AuthToken = uuid.New()
+				createCalls <- agent
+				return agent, nil
+			},
+		).Times(1)
+
+		mSAC.EXPECT().Delete(gomock.Any(), gomock.Any()).DoAndReturn(func(_ context.Context, _ uuid.UUID) error {
+			assert.True(t, closed, "Delete should only be called after Close")
+			return nil
+		}).AnyTimes()
+
+		api := agentcontainers.NewAPI(logger,
+			agentcontainers.WithContainerCLI(fCCLI),
+			agentcontainers.WithDevcontainerCLI(fDCCLI),
+			agentcontainers.WithDevcontainers(
+				[]codersdk.WorkspaceAgentDevcontainer{terraformDevcontainer},
+				[]codersdk.WorkspaceAgentScript{{ID: terraformDevcontainer.ID, LogSourceID: uuid.New()}},
+			),
+			agentcontainers.WithSubAgentClient(mSAC),
+			agentcontainers.WithSubAgentURL("test-subagent-url"),
+			agentcontainers.WithWatcher(watcher.NewNoop()),
+		)
+		api.Start()
+		defer func() {
+			closed = true
+			api.Close()
+		}()
+
+		// When: The devcontainer is created (triggering injection).
+		err := api.CreateDevcontainer(terraformDevcontainer.WorkspaceFolder, terraformDevcontainer.ConfigPath)
+		require.NoError(t, err)
+
+		// Then: The subagent sent to Create has the correct
+		// container-internal directory, not the host path.
+		createdAgent := testutil.RequireReceive(ctx, t, createCalls)
+		assert.Equal(t, terraformAgentID, createdAgent.ID,
+			"agent should use terraform-defined ID")
+		assert.Equal(t, "/workspaces/project", createdAgent.Directory,
+			"directory should be the container-internal path from devcontainer "+
+				"read-configuration, not the host-side workspace_folder")
+	})
+
 	t.Run("Error", func(t *testing.T) {
 		t.Parallel()
 

agent/agentcontextconfig/api.go

@@ -0,0 +1,340 @@
+package agentcontextconfig
+
+import (
+	"cmp"
+	"io"
+	"net/http"
+	"os"
+	"path/filepath"
+	"regexp"
+	"strings"
+
+	"github.com/go-chi/chi/v5"
+
+	"github.com/coder/coder/v2/coderd/httpapi"
+	"github.com/coder/coder/v2/codersdk"
+	"github.com/coder/coder/v2/codersdk/workspacesdk"
+)
+
+// Env var names for context configuration. Prefixed with EXP_
+// to indicate these are experimental and may change.
+const (
+	EnvInstructionsDirs = "CODER_AGENT_EXP_INSTRUCTIONS_DIRS"
+	EnvInstructionsFile = "CODER_AGENT_EXP_INSTRUCTIONS_FILE"
+	EnvSkillsDirs       = "CODER_AGENT_EXP_SKILLS_DIRS"
+	EnvSkillMetaFile    = "CODER_AGENT_EXP_SKILL_META_FILE"
+	EnvMCPConfigFiles   = "CODER_AGENT_EXP_MCP_CONFIG_FILES"
+)
+
+const (
+	maxInstructionFileBytes = 64 * 1024
+	maxSkillMetaBytes       = 64 * 1024
+)
+
+// markdownCommentPattern strips HTML comments from instruction
+// file content for security (prevents hidden prompt injection).
+var markdownCommentPattern = regexp.MustCompile(`<!--[\s\S]*?-->`)
+
+// invisibleRunePattern strips invisible Unicode characters that
+// could be used for prompt injection.
+//
+//nolint:gocritic // Non-ASCII char ranges are intentional for invisible Unicode stripping.
+var invisibleRunePattern = regexp.MustCompile(
+	"[\u00ad\u034f\u061c\u070f" +
+		"\u115f\u1160\u17b4\u17b5" +
+		"\u180b-\u180f" +
+		"\u200b\u200d\u200e\u200f" +
+		"\u202a-\u202e" +
+		"\u2060-\u206f" +
+		"\u3164" +
+		"\ufe00-\ufe0f" +
+		"\ufeff" +
+		"\uffa0" +
+		"\ufff0-\ufff8]",
+)
+
+// skillNamePattern validates kebab-case skill names.
+var skillNamePattern = regexp.MustCompile(
+	`^[a-z0-9]+(-[a-z0-9]+)*$`,
+)
+
+// Default values for agent-internal configuration. These are
+// used when the corresponding env vars are unset.
+const (
+	DefaultInstructionsDir  = "~/.coder"
+	DefaultInstructionsFile = "AGENTS.md"
+	DefaultSkillsDir        = ".agents/skills"
+	DefaultSkillMetaFile    = "SKILL.md"
+	DefaultMCPConfigFile    = ".mcp.json"
+)
+
+// API exposes the resolved context configuration through the
+// agent's HTTP API.
+type API struct {
+	workingDir func() string
+}
+
+// NewAPI accepts a closure that returns the working directory.
+// The directory is evaluated lazily on each call to Config(),
+// so the caller can update it after construction.
+func NewAPI(workingDir func() string) *API {
+	if workingDir == nil {
+		workingDir = func() string { return "" }
+	}
+	return &API{workingDir: workingDir}
+}
+
+// Config reads env vars, resolves paths, reads instruction files,
+// and discovers skills. Returns the HTTP response and the resolved
+// MCP config file paths (used only agent-internally). Exported
+// for use by tests.
+func Config(workingDir string) (workspacesdk.ContextConfigResponse, []string) {
+	// TrimSpace all env vars before cmp.Or so that a
+	// whitespace-only value falls through to the default
+	// consistently. ResolvePaths also trims each comma-
+	// separated entry, but without pre-trimming here a
+	// bare " " would bypass cmp.Or and produce nil.
+	instructionsDir := cmp.Or(strings.TrimSpace(os.Getenv(EnvInstructionsDirs)), DefaultInstructionsDir)
+	instructionsFile := cmp.Or(strings.TrimSpace(os.Getenv(EnvInstructionsFile)), DefaultInstructionsFile)
+	skillsDir := cmp.Or(strings.TrimSpace(os.Getenv(EnvSkillsDirs)), DefaultSkillsDir)
+	skillMetaFile := cmp.Or(strings.TrimSpace(os.Getenv(EnvSkillMetaFile)), DefaultSkillMetaFile)
+	mcpConfigFile := cmp.Or(strings.TrimSpace(os.Getenv(EnvMCPConfigFiles)), DefaultMCPConfigFile)
+
+	resolvedInstructionsDirs := ResolvePaths(instructionsDir, workingDir)
+	resolvedSkillsDirs := ResolvePaths(skillsDir, workingDir)
+
+	// Read instruction files from each configured directory.
+	parts := readInstructionFiles(resolvedInstructionsDirs, instructionsFile)
+
+	// Also check the working directory for the instruction file,
+	// unless it was already covered by InstructionsDirs.
+	if workingDir != "" {
+		seenDirs := make(map[string]struct{}, len(resolvedInstructionsDirs))
+		for _, d := range resolvedInstructionsDirs {
+			seenDirs[d] = struct{}{}
+		}
+		if _, ok := seenDirs[workingDir]; !ok {
+			if entry, found := readInstructionFileFromDir(workingDir, instructionsFile); found {
+				parts = append(parts, entry)
+			}
+		}
+	}
+
+	// Discover skills from each configured skills directory.
+	skillParts := discoverSkills(resolvedSkillsDirs, skillMetaFile)
+	parts = append(parts, skillParts...)
+
+	// Guarantee non-nil slice to signal agent support.
+	if parts == nil {
+		parts = []codersdk.ChatMessagePart{}
+	}
+
+	return workspacesdk.ContextConfigResponse{
+		Parts: parts,
+	}, ResolvePaths(mcpConfigFile, workingDir)
+}
+
+// ContextPartsFromDir reads instruction files and discovers skills
+// from a specific directory, using default file names. This is used
+// by the CLI chat context commands to read context from an arbitrary
+// directory without consulting agent env vars.
+func ContextPartsFromDir(dir string) []codersdk.ChatMessagePart {
+	var parts []codersdk.ChatMessagePart
+
+	if entry, found := readInstructionFileFromDir(dir, DefaultInstructionsFile); found {
+		parts = append(parts, entry)
+	}
+
+	// Reuse ResolvePaths so CLI skill discovery follows the same
+	// project-relative path handling as agent config resolution.
+	skillParts := discoverSkills(
+		ResolvePaths(strings.Join([]string{DefaultSkillsDir, "skills"}, ","), dir),
+		DefaultSkillMetaFile,
+	)
+	parts = append(parts, skillParts...)
+
+	// Guarantee non-nil slice.
+	if parts == nil {
+		parts = []codersdk.ChatMessagePart{}
+	}
+
+	return parts
+}
+
+// MCPConfigFiles returns the resolved MCP configuration file
+// paths for the agent's MCP manager.
+func (api *API) MCPConfigFiles() []string {
+	_, mcpFiles := Config(api.workingDir())
+	return mcpFiles
+}
+
+// Routes returns the HTTP handler for the context config
+// endpoint.
+func (api *API) Routes() http.Handler {
+	r := chi.NewRouter()
+	r.Get("/", api.handleGet)
+	return r
+}
+
+func (api *API) handleGet(rw http.ResponseWriter, r *http.Request) {
+	response, _ := Config(api.workingDir())
+	httpapi.Write(r.Context(), rw, http.StatusOK, response)
+}
+
+// readInstructionFiles reads instruction files from each given
+// directory. Missing directories are silently skipped. Duplicate
+// directories are deduplicated.
+func readInstructionFiles(dirs []string, fileName string) []codersdk.ChatMessagePart {
+	var parts []codersdk.ChatMessagePart
+	seen := make(map[string]struct{}, len(dirs))
+	for _, dir := range dirs {
+		if _, ok := seen[dir]; ok {
+			continue
+		}
+		seen[dir] = struct{}{}
+		if part, found := readInstructionFileFromDir(dir, fileName); found {
+			parts = append(parts, part)
+		}
+	}
+	return parts
+}
+
+// readInstructionFileFromDir scans a directory for a file matching
+// fileName (case-insensitive) and reads its contents.
+func readInstructionFileFromDir(dir, fileName string) (codersdk.ChatMessagePart, bool) {
+	dirEntries, err := os.ReadDir(dir)
+	if err != nil {
+		return codersdk.ChatMessagePart{}, false
+	}
+
+	for _, e := range dirEntries {
+		if e.IsDir() {
+			continue
+		}
+		if strings.EqualFold(strings.TrimSpace(e.Name()), fileName) {
+			filePath := filepath.Join(dir, e.Name())
+			content, truncated, ok := readAndSanitizeFile(filePath, maxInstructionFileBytes)
+			if !ok {
+				return codersdk.ChatMessagePart{}, false
+			}
+			if content == "" {
+				return codersdk.ChatMessagePart{}, false
+			}
+			return codersdk.ChatMessagePart{
+				Type:                 codersdk.ChatMessagePartTypeContextFile,
+				ContextFilePath:      filePath,
+				ContextFileContent:   content,
+				ContextFileTruncated: truncated,
+			}, true
+		}
+	}
+	return codersdk.ChatMessagePart{}, false
+}
+
+// readAndSanitizeFile reads the file at path, capping the read
+// at maxBytes to avoid unbounded memory allocation. It sanitizes
+// the content (strips HTML comments and invisible Unicode) and
+// returns the result. Returns false if the file cannot be read.
+func readAndSanitizeFile(path string, maxBytes int64) (content string, truncated bool, ok bool) {
+	f, err := os.Open(path)
+	if err != nil {
+		return "", false, false
+	}
+	defer f.Close()
+
+	// Read at most maxBytes+1 to detect truncation without
+	// allocating the entire file into memory.
+	raw, err := io.ReadAll(io.LimitReader(f, maxBytes+1))
+	if err != nil {
+		return "", false, false
+	}
+
+	truncated = int64(len(raw)) > maxBytes
+	if truncated {
+		raw = raw[:maxBytes]
+	}
+
+	s := sanitizeInstructionMarkdown(string(raw))
+	if s == "" {
+		return "", truncated, true
+	}
+	return s, truncated, true
+}
+
+// sanitizeInstructionMarkdown strips HTML comments, invisible
+// Unicode characters, and CRLF line endings from instruction
+// file content.
+func sanitizeInstructionMarkdown(content string) string {
+	content = strings.ReplaceAll(content, "\r\n", "\n")
+	content = strings.ReplaceAll(content, "\r", "\n")
+	content = markdownCommentPattern.ReplaceAllString(content, "")
+	content = invisibleRunePattern.ReplaceAllString(content, "")
+	return strings.TrimSpace(content)
+}
+
+// discoverSkills walks the given skills directories and returns
+// metadata for every valid skill it finds. Body and supporting
+// file lists are NOT included; chatd fetches those on demand
+// via read_skill. Missing directories or individual errors are
+// silently skipped.
+func discoverSkills(skillsDirs []string, metaFile string) []codersdk.ChatMessagePart {
+	seen := make(map[string]struct{})
+	var parts []codersdk.ChatMessagePart
+
+	for _, skillsDir := range skillsDirs {
+		entries, err := os.ReadDir(skillsDir)
+		if err != nil {
+			continue
+		}
+
+		for _, entry := range entries {
+			if !entry.IsDir() {
+				continue
+			}
+
+			metaPath := filepath.Join(skillsDir, entry.Name(), metaFile)
+			f, err := os.Open(metaPath)
+			if err != nil {
+				continue
+			}
+			raw, err := io.ReadAll(io.LimitReader(f, maxSkillMetaBytes+1))
+			_ = f.Close()
+			if err != nil {
+				continue
+			}
+			if int64(len(raw)) > maxSkillMetaBytes {
+				raw = raw[:maxSkillMetaBytes]
+			}
+
+			name, description, _, err := workspacesdk.ParseSkillFrontmatter(string(raw))
+			if err != nil {
+				continue
+			}
+
+			// The directory name must match the declared name.
+			if name != entry.Name() {
+				continue
+			}
+			if !skillNamePattern.MatchString(name) {
+				continue
+			}
+
+			// First occurrence wins across directories.
+			if _, ok := seen[name]; ok {
+				continue
+			}
+			seen[name] = struct{}{}
+
+			skillDir := filepath.Join(skillsDir, entry.Name())
+			parts = append(parts, codersdk.ChatMessagePart{
+				Type:                     codersdk.ChatMessagePartTypeSkill,
+				SkillName:                name,
+				SkillDescription:         description,
+				SkillDir:                 skillDir,
+				ContextFileSkillMetaFile: metaFile,
+			})
+		}
+	}
+
+	return parts
+}

agent/agentcontextconfig/api_test.go

@@ -0,0 +1,485 @@
+package agentcontextconfig_test
+
+import (
+	"os"
+	"path/filepath"
+	"strings"
+	"testing"
+
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/agent/agentcontextconfig"
+	"github.com/coder/coder/v2/codersdk"
+)
+
+// filterParts returns only the parts matching the given type.
+func filterParts(parts []codersdk.ChatMessagePart, t codersdk.ChatMessagePartType) []codersdk.ChatMessagePart {
+	var out []codersdk.ChatMessagePart
+	for _, p := range parts {
+		if p.Type == t {
+			out = append(out, p)
+		}
+	}
+	return out
+}
+
+func writeSkillMetaFileInRoot(t *testing.T, skillsRoot, name, description string) string {
+	t.Helper()
+
+	skillDir := filepath.Join(skillsRoot, name)
+	require.NoError(t, os.MkdirAll(skillDir, 0o755))
+	require.NoError(t, os.WriteFile(
+		filepath.Join(skillDir, "SKILL.md"),
+		[]byte("---\nname: "+name+"\ndescription: "+description+"\n---\nSkill body"),
+		0o600,
+	))
+
+	return skillDir
+}
+
+func writeSkillMetaFile(t *testing.T, dir, name, description string) string {
+	t.Helper()
+	return writeSkillMetaFileInRoot(t, filepath.Join(dir, ".agents", "skills"), name, description)
+}
+
+func TestContextPartsFromDir(t *testing.T) {
+	t.Parallel()
+
+	t.Run("ReturnsInstructionFilePart", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		instructionPath := filepath.Join(dir, "AGENTS.md")
+		require.NoError(t, os.WriteFile(instructionPath, []byte("project instructions"), 0o600))
+
+		parts := agentcontextconfig.ContextPartsFromDir(dir)
+		contextParts := filterParts(parts, codersdk.ChatMessagePartTypeContextFile)
+		skillParts := filterParts(parts, codersdk.ChatMessagePartTypeSkill)
+
+		require.Len(t, parts, 1)
+		require.Len(t, contextParts, 1)
+		require.Empty(t, skillParts)
+		require.Equal(t, instructionPath, contextParts[0].ContextFilePath)
+		require.Equal(t, "project instructions", contextParts[0].ContextFileContent)
+		require.False(t, contextParts[0].ContextFileTruncated)
+	})
+
+	t.Run("ReturnsSkillParts", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		skillDir := writeSkillMetaFile(t, dir, "my-skill", "A test skill")
+
+		parts := agentcontextconfig.ContextPartsFromDir(dir)
+		contextParts := filterParts(parts, codersdk.ChatMessagePartTypeContextFile)
+		skillParts := filterParts(parts, codersdk.ChatMessagePartTypeSkill)
+
+		require.Len(t, parts, 1)
+		require.Empty(t, contextParts)
+		require.Len(t, skillParts, 1)
+		require.Equal(t, "my-skill", skillParts[0].SkillName)
+		require.Equal(t, "A test skill", skillParts[0].SkillDescription)
+		require.Equal(t, skillDir, skillParts[0].SkillDir)
+		require.Equal(t, "SKILL.md", skillParts[0].ContextFileSkillMetaFile)
+	})
+
+	t.Run("ReturnsSkillPartsFromSkillsDir", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		skillDir := writeSkillMetaFileInRoot(
+			t,
+			filepath.Join(dir, "skills"),
+			"my-skill",
+			"A test skill",
+		)
+
+		parts := agentcontextconfig.ContextPartsFromDir(dir)
+		contextParts := filterParts(parts, codersdk.ChatMessagePartTypeContextFile)
+		skillParts := filterParts(parts, codersdk.ChatMessagePartTypeSkill)
+
+		require.Len(t, parts, 1)
+		require.Empty(t, contextParts)
+		require.Len(t, skillParts, 1)
+		require.Equal(t, "my-skill", skillParts[0].SkillName)
+		require.Equal(t, "A test skill", skillParts[0].SkillDescription)
+		require.Equal(t, skillDir, skillParts[0].SkillDir)
+		require.Equal(t, "SKILL.md", skillParts[0].ContextFileSkillMetaFile)
+	})
+
+	t.Run("ReturnsEmptyForEmptyDir", func(t *testing.T) {
+		t.Parallel()
+
+		parts := agentcontextconfig.ContextPartsFromDir(t.TempDir())
+
+		require.NotNil(t, parts)
+		require.Empty(t, parts)
+	})
+
+	t.Run("ReturnsCombinedResults", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		instructionPath := filepath.Join(dir, "AGENTS.md")
+		require.NoError(t, os.WriteFile(instructionPath, []byte("combined instructions"), 0o600))
+		skillDir := writeSkillMetaFile(t, dir, "combined-skill", "Combined test skill")
+
+		parts := agentcontextconfig.ContextPartsFromDir(dir)
+		contextParts := filterParts(parts, codersdk.ChatMessagePartTypeContextFile)
+		skillParts := filterParts(parts, codersdk.ChatMessagePartTypeSkill)
+
+		require.Len(t, parts, 2)
+		require.Len(t, contextParts, 1)
+		require.Len(t, skillParts, 1)
+		require.Equal(t, instructionPath, contextParts[0].ContextFilePath)
+		require.Equal(t, "combined instructions", contextParts[0].ContextFileContent)
+		require.Equal(t, "combined-skill", skillParts[0].SkillName)
+		require.Equal(t, skillDir, skillParts[0].SkillDir)
+	})
+}
+
+func setupConfigTestEnv(t *testing.T, overrides map[string]string) string {
+	t.Helper()
+
+	fakeHome := t.TempDir()
+	t.Setenv("HOME", fakeHome)
+	t.Setenv("USERPROFILE", fakeHome)
+	t.Setenv(agentcontextconfig.EnvInstructionsDirs, "")
+	t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
+	t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
+	t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
+	t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
+
+	for key, value := range overrides {
+		t.Setenv(key, value)
+	}
+
+	return fakeHome
+}
+
+func TestConfig(t *testing.T) {
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
+	t.Run("Defaults", func(t *testing.T) {
+		setupConfigTestEnv(t, nil)
+
+		workDir := platformAbsPath("work")
+		cfg, mcpFiles := agentcontextconfig.Config(workDir)
+
+		// Parts is always non-nil.
+		require.NotNil(t, cfg.Parts)
+		// Default MCP config file is ".mcp.json" (relative),
+		// resolved against the working directory.
+		require.Equal(t, []string{filepath.Join(workDir, ".mcp.json")}, mcpFiles)
+	})
+
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
+	t.Run("CustomEnvVars", func(t *testing.T) {
+		optInstructions := t.TempDir()
+		optSkills := t.TempDir()
+		optMCP := platformAbsPath("opt", "mcp.json")
+		setupConfigTestEnv(t, map[string]string{
+			agentcontextconfig.EnvInstructionsDirs: optInstructions,
+			agentcontextconfig.EnvInstructionsFile: "CUSTOM.md",
+			agentcontextconfig.EnvSkillsDirs:       optSkills,
+			agentcontextconfig.EnvSkillMetaFile:    "META.yaml",
+			agentcontextconfig.EnvMCPConfigFiles:   optMCP,
+		})
+
+		// Create files matching the custom names so we can
+		// verify the env vars actually change lookup behavior.
+		require.NoError(t, os.WriteFile(filepath.Join(optInstructions, "CUSTOM.md"), []byte("custom instructions"), 0o600))
+		skillDir := filepath.Join(optSkills, "my-skill")
+		require.NoError(t, os.MkdirAll(skillDir, 0o755))
+		require.NoError(t, os.WriteFile(
+			filepath.Join(skillDir, "META.yaml"),
+			[]byte("---\nname: my-skill\ndescription: custom meta\n---\n"),
+			0o600,
+		))
+
+		workDir := platformAbsPath("work")
+		cfg, mcpFiles := agentcontextconfig.Config(workDir)
+
+		require.Equal(t, []string{optMCP}, mcpFiles)
+		ctxFiles := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeContextFile)
+		require.Len(t, ctxFiles, 1)
+		require.Equal(t, "custom instructions", ctxFiles[0].ContextFileContent)
+		skillParts := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeSkill)
+		require.Len(t, skillParts, 1)
+		require.Equal(t, "my-skill", skillParts[0].SkillName)
+		require.Equal(t, "META.yaml", skillParts[0].ContextFileSkillMetaFile)
+	})
+
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
+	t.Run("WhitespaceInFileNames", func(t *testing.T) {
+		fakeHome := setupConfigTestEnv(t, map[string]string{
+			agentcontextconfig.EnvInstructionsFile: "  CLAUDE.md  ",
+		})
+		t.Setenv(agentcontextconfig.EnvInstructionsDirs, fakeHome)
+
+		workDir := t.TempDir()
+		// Create a file matching the trimmed name.
+		require.NoError(t, os.WriteFile(filepath.Join(fakeHome, "CLAUDE.md"), []byte("hello"), 0o600))
+
+		cfg, _ := agentcontextconfig.Config(workDir)
+
+		ctxFiles := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeContextFile)
+		require.Len(t, ctxFiles, 1)
+		require.Equal(t, "hello", ctxFiles[0].ContextFileContent)
+	})
+
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
+	t.Run("CommaSeparatedDirs", func(t *testing.T) {
+		a := t.TempDir()
+		b := t.TempDir()
+		setupConfigTestEnv(t, map[string]string{
+			agentcontextconfig.EnvInstructionsDirs: a + "," + b,
+		})
+
+		// Put instruction files in both dirs.
+		require.NoError(t, os.WriteFile(filepath.Join(a, "AGENTS.md"), []byte("from a"), 0o600))
+		require.NoError(t, os.WriteFile(filepath.Join(b, "AGENTS.md"), []byte("from b"), 0o600))
+
+		workDir := t.TempDir()
+		cfg, _ := agentcontextconfig.Config(workDir)
+
+		ctxFiles := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeContextFile)
+		require.Len(t, ctxFiles, 2)
+		require.Equal(t, "from a", ctxFiles[0].ContextFileContent)
+		require.Equal(t, "from b", ctxFiles[1].ContextFileContent)
+	})
+
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
+	t.Run("ReadsInstructionFiles", func(t *testing.T) {
+		workDir := t.TempDir()
+		fakeHome := setupConfigTestEnv(t, nil)
+
+		// Create ~/.coder/AGENTS.md
+		coderDir := filepath.Join(fakeHome, ".coder")
+		require.NoError(t, os.MkdirAll(coderDir, 0o755))
+		require.NoError(t, os.WriteFile(
+			filepath.Join(coderDir, "AGENTS.md"),
+			[]byte("home instructions"),
+			0o600,
+		))
+
+		cfg, _ := agentcontextconfig.Config(workDir)
+
+		ctxFiles := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeContextFile)
+		require.NotNil(t, cfg.Parts)
+		require.Len(t, ctxFiles, 1)
+		require.Equal(t, "home instructions", ctxFiles[0].ContextFileContent)
+		require.Equal(t, filepath.Join(coderDir, "AGENTS.md"), ctxFiles[0].ContextFilePath)
+		require.False(t, ctxFiles[0].ContextFileTruncated)
+	})
+
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
+	t.Run("ReadsWorkingDirInstructionFile", func(t *testing.T) {
+		setupConfigTestEnv(t, nil)
+		workDir := t.TempDir()
+
+		// Create AGENTS.md in the working directory.
+		require.NoError(t, os.WriteFile(
+			filepath.Join(workDir, "AGENTS.md"),
+			[]byte("project instructions"),
+			0o600,
+		))
+
+		cfg, _ := agentcontextconfig.Config(workDir)
+
+		// Should find the working dir file (not in instruction dirs).
+		ctxFiles := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeContextFile)
+		require.NotNil(t, cfg.Parts)
+		require.Len(t, ctxFiles, 1)
+		require.Equal(t, "project instructions", ctxFiles[0].ContextFileContent)
+		require.Equal(t, filepath.Join(workDir, "AGENTS.md"), ctxFiles[0].ContextFilePath)
+	})
+
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
+	t.Run("TruncatesLargeInstructionFile", func(t *testing.T) {
+		setupConfigTestEnv(t, nil)
+		workDir := t.TempDir()
+		largeContent := strings.Repeat("a", 64*1024+100)
+		require.NoError(t, os.WriteFile(filepath.Join(workDir, "AGENTS.md"), []byte(largeContent), 0o600))
+
+		cfg, _ := agentcontextconfig.Config(workDir)
+
+		ctxFiles := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeContextFile)
+		require.Len(t, ctxFiles, 1)
+		require.True(t, ctxFiles[0].ContextFileTruncated)
+		require.Len(t, ctxFiles[0].ContextFileContent, 64*1024)
+	})
+
+	sanitizationTests := []struct {
+		name     string
+		input    string
+		expected string
+	}{
+		{
+			name:     "SanitizesHTMLComments",
+			input:    "visible\n<!-- hidden -->content",
+			expected: "visible\ncontent",
+		},
+		{
+			name:     "SanitizesInvisibleUnicode",
+			input:    "before\u200bafter",
+			expected: "beforeafter",
+		},
+		{
+			name:     "NormalizesCRLF",
+			input:    "line1\r\nline2\rline3",
+			expected: "line1\nline2\nline3",
+		},
+	}
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
+	for _, tt := range sanitizationTests {
+		t.Run(tt.name, func(t *testing.T) {
+			setupConfigTestEnv(t, nil)
+			workDir := t.TempDir()
+			require.NoError(t, os.WriteFile(
+				filepath.Join(workDir, "AGENTS.md"),
+				[]byte(tt.input),
+				0o600,
+			))
+
+			cfg, _ := agentcontextconfig.Config(workDir)
+
+			ctxFiles := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeContextFile)
+			require.Len(t, ctxFiles, 1)
+			require.Equal(t, tt.expected, ctxFiles[0].ContextFileContent)
+		})
+	}
+
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
+	t.Run("DiscoversSkills", func(t *testing.T) {
+		fakeHome := t.TempDir()
+		t.Setenv("HOME", fakeHome)
+		t.Setenv("USERPROFILE", fakeHome)
+		t.Setenv(agentcontextconfig.EnvInstructionsDirs, fakeHome)
+		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
+		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
+		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
+
+		workDir := t.TempDir()
+		skillsDir := filepath.Join(workDir, ".agents", "skills")
+		t.Setenv(agentcontextconfig.EnvSkillsDirs, skillsDir)
+
+		// Create a valid skill.
+		skillDir := filepath.Join(skillsDir, "my-skill")
+		require.NoError(t, os.MkdirAll(skillDir, 0o755))
+		require.NoError(t, os.WriteFile(
+			filepath.Join(skillDir, "SKILL.md"),
+			[]byte("---\nname: my-skill\ndescription: A test skill\n---\nSkill body"),
+			0o600,
+		))
+
+		cfg, _ := agentcontextconfig.Config(workDir)
+
+		skillParts := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeSkill)
+		require.Len(t, skillParts, 1)
+		require.Equal(t, "my-skill", skillParts[0].SkillName)
+		require.Equal(t, "A test skill", skillParts[0].SkillDescription)
+		require.Equal(t, skillDir, skillParts[0].SkillDir)
+		require.Equal(t, "SKILL.md", skillParts[0].ContextFileSkillMetaFile)
+	})
+
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
+	t.Run("SkipsMissingDirs", func(t *testing.T) {
+		nonExistent := filepath.Join(t.TempDir(), "does-not-exist")
+		setupConfigTestEnv(t, map[string]string{
+			agentcontextconfig.EnvInstructionsDirs: nonExistent,
+			agentcontextconfig.EnvSkillsDirs:       nonExistent,
+		})
+
+		workDir := t.TempDir()
+		cfg, _ := agentcontextconfig.Config(workDir)
+
+		// Non-nil empty slice (signals agent supports new format).
+		require.NotNil(t, cfg.Parts)
+		require.Empty(t, cfg.Parts)
+	})
+
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
+	t.Run("MCPConfigFilesResolvedSeparately", func(t *testing.T) {
+		optMCP := platformAbsPath("opt", "custom.json")
+		fakeHome := setupConfigTestEnv(t, map[string]string{
+			agentcontextconfig.EnvMCPConfigFiles: optMCP,
+		})
+		t.Setenv(agentcontextconfig.EnvInstructionsDirs, fakeHome)
+
+		workDir := t.TempDir()
+		_, mcpFiles := agentcontextconfig.Config(workDir)
+
+		require.Equal(t, []string{optMCP}, mcpFiles)
+	})
+
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
+	t.Run("SkillNameMustMatchDir", func(t *testing.T) {
+		fakeHome := setupConfigTestEnv(t, nil)
+		t.Setenv(agentcontextconfig.EnvInstructionsDirs, fakeHome)
+
+		workDir := t.TempDir()
+		skillsDir := filepath.Join(workDir, "skills")
+		t.Setenv(agentcontextconfig.EnvSkillsDirs, skillsDir)
+
+		// Skill name in frontmatter doesn't match directory name.
+		skillDir := filepath.Join(skillsDir, "wrong-dir-name")
+		require.NoError(t, os.MkdirAll(skillDir, 0o755))
+		require.NoError(t, os.WriteFile(
+			filepath.Join(skillDir, "SKILL.md"),
+			[]byte("---\nname: actual-name\ndescription: mismatch\n---\n"),
+			0o600,
+		))
+
+		cfg, _ := agentcontextconfig.Config(workDir)
+		skillParts := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeSkill)
+		require.Empty(t, skillParts)
+	})
+
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
+	t.Run("DuplicateSkillsFirstWins", func(t *testing.T) {
+		fakeHome := setupConfigTestEnv(t, nil)
+		t.Setenv(agentcontextconfig.EnvInstructionsDirs, fakeHome)
+
+		workDir := t.TempDir()
+		skillsDir1 := filepath.Join(workDir, "skills1")
+		skillsDir2 := filepath.Join(workDir, "skills2")
+		t.Setenv(agentcontextconfig.EnvSkillsDirs, skillsDir1+","+skillsDir2)
+
+		// Same skill name in both directories.
+		for _, dir := range []string{skillsDir1, skillsDir2} {
+			skillDir := filepath.Join(dir, "dup-skill")
+			require.NoError(t, os.MkdirAll(skillDir, 0o755))
+			require.NoError(t, os.WriteFile(
+				filepath.Join(skillDir, "SKILL.md"),
+				[]byte("---\nname: dup-skill\ndescription: from "+filepath.Base(dir)+"\n---\n"),
+				0o600,
+			))
+		}
+
+		cfg, _ := agentcontextconfig.Config(workDir)
+		skillParts := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeSkill)
+		require.Len(t, skillParts, 1)
+		require.Equal(t, "from skills1", skillParts[0].SkillDescription)
+	})
+}
+
+func TestNewAPI_LazyDirectory(t *testing.T) {
+	t.Setenv(agentcontextconfig.EnvInstructionsDirs, "")
+	t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
+	t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
+	t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
+	t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
+
+	dir := ""
+	api := agentcontextconfig.NewAPI(func() string { return dir })
+
+	// Before directory is set, MCP paths resolve to nothing.
+	mcpFiles := api.MCPConfigFiles()
+	require.Empty(t, mcpFiles)
+
+	// After setting the directory, MCPConfigFiles() picks it up.
+	dir = platformAbsPath("work")
+	mcpFiles = api.MCPConfigFiles()
+	require.NotEmpty(t, mcpFiles)
+	require.Equal(t, []string{filepath.Join(dir, ".mcp.json")}, mcpFiles)
+}

agent/agentcontextconfig/resolve.go

@@ -0,0 +1,55 @@
+package agentcontextconfig
+
+import (
+	"os"
+	"path/filepath"
+	"strings"
+)
+
+// ResolvePath resolves a single path that may be absolute,
+// home-relative (~/ or ~), or relative to the given base
+// directory. Returns an absolute path. Empty input returns empty.
+func ResolvePath(raw, baseDir string) string {
+	raw = strings.TrimSpace(raw)
+	if raw == "" {
+		return ""
+	}
+	switch {
+	case raw == "~":
+		home, err := os.UserHomeDir()
+		if err != nil {
+			return ""
+		}
+		return home
+	case strings.HasPrefix(raw, "~/"):
+		home, err := os.UserHomeDir()
+		if err != nil {
+			return ""
+		}
+		return filepath.Join(home, raw[2:])
+	case filepath.IsAbs(raw):
+		return raw
+	default:
+		if baseDir == "" {
+			return ""
+		}
+		return filepath.Join(baseDir, raw)
+	}
+}
+
+// ResolvePaths splits a comma-separated list of paths and
+// resolves each entry independently. Empty entries and entries
+// that resolve to empty strings are skipped.
+func ResolvePaths(raw, baseDir string) []string {
+	if strings.TrimSpace(raw) == "" {
+		return nil
+	}
+	parts := strings.Split(raw, ",")
+	out := make([]string, 0, len(parts))
+	for _, p := range parts {
+		if resolved := ResolvePath(p, baseDir); resolved != "" {
+			out = append(out, resolved)
+		}
+	}
+	return out
+}

agent/agentcontextconfig/resolve_test.go

@@ -0,0 +1,152 @@
+package agentcontextconfig_test
+
+import (
+	"path/filepath"
+	"runtime"
+	"testing"
+
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/agent/agentcontextconfig"
+)
+
+// platformAbsPath constructs an absolute path that is valid
+// on the current platform. On Windows paths must include a
+// drive letter to be considered absolute.
+func platformAbsPath(parts ...string) string {
+	if runtime.GOOS == "windows" {
+		return `C:\` + filepath.Join(parts...)
+	}
+	return "/" + filepath.Join(parts...)
+}
+
+func TestResolvePath(t *testing.T) { //nolint:tparallel // subtests using t.Setenv cannot be parallel
+	t.Run("EmptyInput", func(t *testing.T) {
+		t.Parallel()
+		require.Equal(t, "", agentcontextconfig.ResolvePath("", platformAbsPath("base")))
+	})
+
+	t.Run("WhitespaceOnly", func(t *testing.T) {
+		t.Parallel()
+		require.Equal(t, "", agentcontextconfig.ResolvePath("   ", platformAbsPath("base")))
+	})
+
+	// Tests that use t.Setenv cannot be parallel.
+	t.Run("TildeAlone", func(t *testing.T) {
+		fakeHome := t.TempDir()
+		t.Setenv("HOME", fakeHome)
+		t.Setenv("USERPROFILE", fakeHome)
+		got := agentcontextconfig.ResolvePath("~", platformAbsPath("base"))
+		require.Equal(t, fakeHome, got)
+	})
+
+	t.Run("TildeSlashPath", func(t *testing.T) {
+		fakeHome := t.TempDir()
+		t.Setenv("HOME", fakeHome)
+		t.Setenv("USERPROFILE", fakeHome)
+		got := agentcontextconfig.ResolvePath("~/docs/readme", platformAbsPath("base"))
+		require.Equal(t, filepath.Join(fakeHome, "docs", "readme"), got)
+	})
+
+	t.Run("AbsolutePath", func(t *testing.T) {
+		t.Parallel()
+		p := platformAbsPath("etc", "coder")
+		got := agentcontextconfig.ResolvePath(p, platformAbsPath("base"))
+		require.Equal(t, p, got)
+	})
+
+	t.Run("RelativePath", func(t *testing.T) {
+		t.Parallel()
+		base := platformAbsPath("work")
+		got := agentcontextconfig.ResolvePath("foo/bar", base)
+		require.Equal(t, filepath.Join(base, "foo", "bar"), got)
+	})
+
+	t.Run("RelativePathWithWhitespace", func(t *testing.T) {
+		t.Parallel()
+		base := platformAbsPath("work")
+		got := agentcontextconfig.ResolvePath("  foo/bar  ", base)
+		require.Equal(t, filepath.Join(base, "foo", "bar"), got)
+	})
+
+	t.Run("RelativePathWithEmptyBaseDir", func(t *testing.T) {
+		t.Parallel()
+		got := agentcontextconfig.ResolvePath(".agents/skills", "")
+		require.Equal(t, "", got)
+	})
+}
+
+func TestResolvePath_HomeUnset(t *testing.T) {
+	// Cannot be parallel — modifies HOME env var.
+	t.Setenv("HOME", "")
+	// Also clear USERPROFILE for Windows compatibility.
+	t.Setenv("USERPROFILE", "")
+
+	require.Equal(t, "", agentcontextconfig.ResolvePath("~", platformAbsPath("base")))
+	require.Equal(t, "", agentcontextconfig.ResolvePath("~/docs", platformAbsPath("base")))
+}
+
+func TestResolvePaths(t *testing.T) { //nolint:tparallel // subtests using t.Setenv cannot be parallel
+	t.Run("EmptyString", func(t *testing.T) {
+		t.Parallel()
+		require.Nil(t, agentcontextconfig.ResolvePaths("", platformAbsPath("base")))
+	})
+
+	t.Run("WhitespaceOnly", func(t *testing.T) {
+		t.Parallel()
+		require.Nil(t, agentcontextconfig.ResolvePaths("   ", platformAbsPath("base")))
+	})
+
+	t.Run("SingleEntry", func(t *testing.T) {
+		t.Parallel()
+		p := platformAbsPath("abs", "path")
+		got := agentcontextconfig.ResolvePaths(p, platformAbsPath("base"))
+		require.Equal(t, []string{p}, got)
+	})
+
+	// Tests that use t.Setenv cannot be parallel.
+	t.Run("MultipleEntries", func(t *testing.T) {
+		fakeHome := t.TempDir()
+		t.Setenv("HOME", fakeHome)
+		t.Setenv("USERPROFILE", fakeHome)
+		b := platformAbsPath("b")
+		base := platformAbsPath("base")
+		got := agentcontextconfig.ResolvePaths("~/a,"+b+",rel", base)
+		require.Equal(t, []string{
+			filepath.Join(fakeHome, "a"),
+			b,
+			filepath.Join(base, "rel"),
+		}, got)
+	})
+
+	t.Run("TrimsWhitespace", func(t *testing.T) {
+		t.Parallel()
+		a := platformAbsPath("a")
+		b := platformAbsPath("b")
+		got := agentcontextconfig.ResolvePaths("  "+a+" , "+b+"  ", platformAbsPath("base"))
+		require.Equal(t, []string{a, b}, got)
+	})
+
+	t.Run("SkipsEmptyEntries", func(t *testing.T) {
+		t.Parallel()
+		a := platformAbsPath("a")
+		b := platformAbsPath("b")
+		got := agentcontextconfig.ResolvePaths(a+",,"+b+",", platformAbsPath("base"))
+		require.Equal(t, []string{a, b}, got)
+	})
+
+	t.Run("TrailingComma", func(t *testing.T) {
+		t.Parallel()
+		p := platformAbsPath("only")
+		got := agentcontextconfig.ResolvePaths(p+",", platformAbsPath("base"))
+		require.Equal(t, []string{p}, got)
+	})
+
+	t.Run("RelativePathSkippedWhenBaseDirEmpty", func(t *testing.T) {
+		fakeHome := t.TempDir()
+		t.Setenv("HOME", fakeHome)
+		t.Setenv("USERPROFILE", fakeHome)
+		got := agentcontextconfig.ResolvePaths("~/.coder,.agents/skills", "")
+		require.Equal(t, []string{filepath.Join(fakeHome, ".coder")}, got)
+	})
+}

agent/agentproc/process.go

@@ -148,6 +148,11 @@ func (m *manager) start(req workspacesdk.StartProcessRequest, chatID string) (*p
 	for k, v := range req.Env {
 		cmd.Env = append(cmd.Env, fmt.Sprintf("%s=%s", k, v))
 	}
+	// Propagate the chat ID so child processes (e.g.
+	// GIT_ASKPASS) can send it back to the server.
+	if chatID != "" {
+		cmd.Env = append(cmd.Env, fmt.Sprintf("CODER_CHAT_ID=%s", chatID))
+	}
 
 	if err := cmd.Start(); err != nil {
 		cancel()

agent/agentssh/agentssh.go

@@ -117,6 +117,10 @@ type Config struct {
 	X11MaxPort *int
 	// BlockFileTransfer restricts use of file transfer applications.
 	BlockFileTransfer bool
+	// BlockReversePortForwarding disables reverse port forwarding (ssh -R).
+	BlockReversePortForwarding bool
+	// BlockLocalPortForwarding disables local port forwarding (ssh -L).
+	BlockLocalPortForwarding bool
 	// ReportConnection.
 	ReportConnection reportConnectionFunc
 	// Experimental: allow connecting to running containers via Docker exec.
@@ -190,7 +194,7 @@ func NewServer(ctx context.Context, logger slog.Logger, prometheusRegistry *prom
 	}
 
 	forwardHandler := &ssh.ForwardedTCPHandler{}
-	unixForwardHandler := newForwardedUnixHandler(logger)
+	unixForwardHandler := newForwardedUnixHandler(logger, config.BlockReversePortForwarding)
 
 	metrics := newSSHServerMetrics(prometheusRegistry)
 	s := &Server{
@@ -229,8 +233,15 @@ func NewServer(ctx context.Context, logger slog.Logger, prometheusRegistry *prom
 				wrapped := NewJetbrainsChannelWatcher(ctx, s.logger, s.config.ReportConnection, newChan, &s.connCountJetBrains)
 				ssh.DirectTCPIPHandler(srv, conn, wrapped, ctx)
 			},
-			"direct-streamlocal@openssh.com": directStreamLocalHandler,
-			"session":                        ssh.DefaultSessionHandler,
+			"direct-streamlocal@openssh.com": func(srv *ssh.Server, conn *gossh.ServerConn, newChan gossh.NewChannel, ctx ssh.Context) {
+				if s.config.BlockLocalPortForwarding {
+					s.logger.Warn(ctx, "unix local port forward blocked")
+					_ = newChan.Reject(gossh.Prohibited, "local port forwarding is disabled")
+					return
+				}
+				directStreamLocalHandler(srv, conn, newChan, ctx)
+			},
+			"session": ssh.DefaultSessionHandler,
 		},
 		ConnectionFailedCallback: func(conn net.Conn, err error) {
 			s.logger.Warn(ctx, "ssh connection failed",
@@ -250,6 +261,12 @@ func NewServer(ctx context.Context, logger slog.Logger, prometheusRegistry *prom
 		// be set before we start listening.
 		HostSigners: []ssh.Signer{},
 		LocalPortForwardingCallback: func(ctx ssh.Context, destinationHost string, destinationPort uint32) bool {
+			if s.config.BlockLocalPortForwarding {
+				s.logger.Warn(ctx, "local port forward blocked",
+					slog.F("destination_host", destinationHost),
+					slog.F("destination_port", destinationPort))
+				return false
+			}
 			// Allow local port forwarding all!
 			s.logger.Debug(ctx, "local port forward",
 				slog.F("destination_host", destinationHost),
@@ -260,6 +277,12 @@ func NewServer(ctx context.Context, logger slog.Logger, prometheusRegistry *prom
 			return true
 		},
 		ReversePortForwardingCallback: func(ctx ssh.Context, bindHost string, bindPort uint32) bool {
+			if s.config.BlockReversePortForwarding {
+				s.logger.Warn(ctx, "reverse port forward blocked",
+					slog.F("bind_host", bindHost),
+					slog.F("bind_port", bindPort))
+				return false
+			}
 			// Allow reverse port forwarding all!
 			s.logger.Debug(ctx, "reverse port forward",
 				slog.F("bind_host", bindHost),

agent/agentssh/forward.go

@@ -35,8 +35,9 @@ type forwardedStreamLocalPayload struct {
 // streamlocal forwarding (aka. unix forwarding) instead of TCP forwarding.
 type forwardedUnixHandler struct {
 	sync.Mutex
-	log      slog.Logger
-	forwards map[forwardKey]net.Listener
+	log                        slog.Logger
+	forwards                   map[forwardKey]net.Listener
+	blockReversePortForwarding bool
 }
 
 type forwardKey struct {
@@ -44,10 +45,11 @@ type forwardKey struct {
 	addr      string
 }
 
-func newForwardedUnixHandler(log slog.Logger) *forwardedUnixHandler {
+func newForwardedUnixHandler(log slog.Logger, blockReversePortForwarding bool) *forwardedUnixHandler {
 	return &forwardedUnixHandler{
-		log:      log,
-		forwards: make(map[forwardKey]net.Listener),
+		log:                        log,
+		forwards:                   make(map[forwardKey]net.Listener),
+		blockReversePortForwarding: blockReversePortForwarding,
 	}
 }
 
@@ -62,6 +64,10 @@ func (h *forwardedUnixHandler) HandleSSHRequest(ctx ssh.Context, _ *ssh.Server,
 
 	switch req.Type {
 	case "streamlocal-forward@openssh.com":
+		if h.blockReversePortForwarding {
+			log.Warn(ctx, "unix reverse port forward blocked")
+			return false, nil
+		}
 		var reqPayload streamLocalForwardPayload
 		err := gossh.Unmarshal(req.Payload, &reqPayload)
 		if err != nil {

agent/api.go

@@ -32,6 +32,7 @@ func (a *agent) apiHandler() http.Handler {
 	r.Mount("/api/v0/processes", a.processAPI.Routes())
 	r.Mount("/api/v0/desktop", a.desktopAPI.Routes())
 	r.Mount("/api/v0/mcp", a.mcpAPI.Routes())
+	r.Mount("/api/v0/context-config", a.contextConfigAPI.Routes())
 
 	if a.devcontainers {
 		r.Mount("/api/v0/containers", a.containerAPI.Routes())

agent/proto/agent.proto

@@ -98,6 +98,21 @@ message Manifest {
 	repeated WorkspaceApp apps = 11;
 	repeated WorkspaceAgentMetadata.Description metadata = 12;
 	repeated WorkspaceAgentDevcontainer devcontainers = 17;
+	repeated WorkspaceSecret secrets = 19;
+}
+
+// WorkspaceSecret is a secret included in the agent manifest
+// for injection into a workspace.
+message WorkspaceSecret {
+	// Environment variable name to inject (e.g. "GITHUB_TOKEN").
+	// Empty string means this secret is not injected as an env var.
+	string env_name = 1;
+	// File path to write the secret value to (e.g.
+	// "~/.aws/credentials"). Empty string means this secret is not
+	// written to a file.
+	string file_path = 2;
+	// The decrypted secret value.
+	bytes value = 3;
 }
 
 message WorkspaceAgentDevcontainer {

agent/x/agentdesktop/api.go

@@ -1,12 +1,19 @@
 package agentdesktop
 
 import (
+	"context"
 	"encoding/json"
+	"errors"
+	"io"
+	"mime/multipart"
 	"net/http"
+	"net/textproto"
 	"strconv"
+	"sync"
 	"time"
 
 	"github.com/go-chi/chi/v5"
+	"github.com/google/uuid"
 
 	"cdr.dev/slog/v3"
 	"github.com/coder/coder/v2/agent/agentssh"
@@ -47,6 +54,9 @@ type API struct {
 	logger  slog.Logger
 	desktop Desktop
 	clock   quartz.Clock
+
+	closeMu sync.Mutex
+	closed  bool
 }
 
 // NewAPI creates a new desktop streaming API.
@@ -66,6 +76,10 @@ func (a *API) Routes() http.Handler {
 	r := chi.NewRouter()
 	r.Get("/vnc", a.handleDesktopVNC)
 	r.Post("/action", a.handleAction)
+	r.Route("/recording", func(r chi.Router) {
+		r.Post("/start", a.handleRecordingStart)
+		r.Post("/stop", a.handleRecordingStop)
+	})
 	return r
 }
 
@@ -116,6 +130,9 @@ func (a *API) handleAction(rw http.ResponseWriter, r *http.Request) {
 	ctx := r.Context()
 	handlerStart := a.clock.Now()
 
+	// Update last desktop action timestamp for idle recording monitor.
+	a.desktop.RecordActivity()
+
 	// Ensure the desktop is running and grab native dimensions.
 	cfg, err := a.desktop.Start(ctx)
 	if err != nil {
@@ -480,9 +497,205 @@ func (a *API) handleAction(rw http.ResponseWriter, r *http.Request) {
 
 // Close shuts down the desktop session if one is running.
 func (a *API) Close() error {
+	a.closeMu.Lock()
+	if a.closed {
+		a.closeMu.Unlock()
+		return nil
+	}
+	a.closed = true
+	a.closeMu.Unlock()
+
 	return a.desktop.Close()
 }
 
+// decodeRecordingRequest decodes and validates a recording request
+// from the HTTP body, returning the recording ID. Returns false if
+// the request was invalid and an error response was already written.
+func (*API) decodeRecordingRequest(rw http.ResponseWriter, r *http.Request) (string, bool) {
+	ctx := r.Context()
+	var req struct {
+		RecordingID string `json:"recording_id"`
+	}
+	if err := json.NewDecoder(r.Body).Decode(&req); err != nil {
+		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
+			Message: "Failed to decode request body.",
+			Detail:  err.Error(),
+		})
+		return "", false
+	}
+	if req.RecordingID == "" {
+		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
+			Message: "Missing recording_id.",
+		})
+		return "", false
+	}
+	if _, err := uuid.Parse(req.RecordingID); err != nil {
+		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
+			Message: "Invalid recording_id format.",
+			Detail:  "recording_id must be a valid UUID.",
+		})
+		return "", false
+	}
+	return req.RecordingID, true
+}
+
+func (a *API) handleRecordingStart(rw http.ResponseWriter, r *http.Request) {
+	ctx := r.Context()
+	recordingID, ok := a.decodeRecordingRequest(rw, r)
+	if !ok {
+		return
+	}
+
+	a.closeMu.Lock()
+	if a.closed {
+		a.closeMu.Unlock()
+		httpapi.Write(ctx, rw, http.StatusServiceUnavailable, codersdk.Response{
+			Message: "Desktop API is shutting down.",
+		})
+		return
+	}
+	a.closeMu.Unlock()
+
+	if err := a.desktop.StartRecording(ctx, recordingID); err != nil {
+		if errors.Is(err, ErrDesktopClosed) {
+			httpapi.Write(ctx, rw, http.StatusServiceUnavailable, codersdk.Response{
+				Message: "Desktop API is shutting down.",
+			})
+			return
+		}
+		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
+			Message: "Failed to start recording.",
+			Detail:  err.Error(),
+		})
+		return
+	}
+
+	httpapi.Write(ctx, rw, http.StatusOK, codersdk.Response{
+		Message: "Recording started.",
+	})
+}
+
+func (a *API) handleRecordingStop(rw http.ResponseWriter, r *http.Request) {
+	ctx := r.Context()
+
+	recordingID, ok := a.decodeRecordingRequest(rw, r)
+	if !ok {
+		return
+	}
+
+	a.closeMu.Lock()
+	if a.closed {
+		a.closeMu.Unlock()
+		httpapi.Write(ctx, rw, http.StatusServiceUnavailable, codersdk.Response{
+			Message: "Desktop API is shutting down.",
+		})
+		return
+	}
+	a.closeMu.Unlock()
+
+	// Stop recording (idempotent).
+	// Use a context detached from the HTTP request so that if the
+	// connection drops, the recording process can still shut down
+	// gracefully. WithoutCancel preserves request-scoped values.
+	stopCtx, stopCancel := context.WithTimeout(context.WithoutCancel(r.Context()), 30*time.Second)
+	defer stopCancel()
+	artifact, err := a.desktop.StopRecording(stopCtx, recordingID)
+	if err != nil {
+		if errors.Is(err, ErrUnknownRecording) {
+			httpapi.Write(ctx, rw, http.StatusNotFound, codersdk.Response{
+				Message: "Recording not found.",
+				Detail:  err.Error(),
+			})
+			return
+		}
+		if errors.Is(err, ErrRecordingCorrupted) {
+			httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
+				Message: "Recording is corrupted.",
+				Detail:  err.Error(),
+			})
+			return
+		}
+		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
+			Message: "Failed to stop recording.",
+			Detail:  err.Error(),
+		})
+		return
+	}
+	defer artifact.Reader.Close()
+	defer func() {
+		if artifact.ThumbnailReader != nil {
+			_ = artifact.ThumbnailReader.Close()
+		}
+	}()
+
+	if artifact.Size > workspacesdk.MaxRecordingSize {
+		a.logger.Warn(ctx, "recording file exceeds maximum size",
+			slog.F("recording_id", recordingID),
+			slog.F("size", artifact.Size),
+			slog.F("max_size", workspacesdk.MaxRecordingSize),
+		)
+		httpapi.Write(ctx, rw, http.StatusRequestEntityTooLarge, codersdk.Response{
+			Message: "Recording file exceeds maximum allowed size.",
+		})
+		return
+	}
+
+	// Discard the thumbnail if it exceeds the maximum size.
+	// The server-side consumer also enforces this per-part, but
+	// rejecting it here avoids streaming a large thumbnail over
+	// the wire for nothing.
+	if artifact.ThumbnailReader != nil && artifact.ThumbnailSize > workspacesdk.MaxThumbnailSize {
+		a.logger.Warn(ctx, "thumbnail file exceeds maximum size, omitting",
+			slog.F("recording_id", recordingID),
+			slog.F("size", artifact.ThumbnailSize),
+			slog.F("max_size", workspacesdk.MaxThumbnailSize),
+		)
+		_ = artifact.ThumbnailReader.Close()
+		artifact.ThumbnailReader = nil
+		artifact.ThumbnailSize = 0
+	}
+
+	// The multipart response is best-effort: once WriteHeader(200) is
+	// called, CreatePart failures produce a truncated response without
+	// the closing boundary. The server-side consumer handles this
+	// gracefully, preserving any parts read before the error.
+	mw := multipart.NewWriter(rw)
+	defer mw.Close()
+	rw.Header().Set("Content-Type", "multipart/mixed; boundary="+mw.Boundary())
+	rw.WriteHeader(http.StatusOK)
+
+	// Part 1: video/mp4 (always present).
+	videoPart, err := mw.CreatePart(textproto.MIMEHeader{
+		"Content-Type": {"video/mp4"},
+	})
+	if err != nil {
+		a.logger.Warn(ctx, "failed to create video multipart part",
+			slog.F("recording_id", recordingID),
+			slog.Error(err))
+		return
+	}
+	if _, err := io.Copy(videoPart, artifact.Reader); err != nil {
+		a.logger.Warn(ctx, "failed to write video multipart part",
+			slog.F("recording_id", recordingID),
+			slog.Error(err))
+		return
+	}
+
+	// Part 2: image/jpeg (present only when thumbnail was extracted).
+	if artifact.ThumbnailReader != nil {
+		thumbPart, err := mw.CreatePart(textproto.MIMEHeader{
+			"Content-Type": {"image/jpeg"},
+		})
+		if err != nil {
+			a.logger.Warn(ctx, "failed to create thumbnail multipart part",
+				slog.F("recording_id", recordingID),
+				slog.Error(err))
+			return
+		}
+		_, _ = io.Copy(thumbPart, artifact.ThumbnailReader)
+	}
+}
+
 // coordFromAction extracts the coordinate pair from a DesktopAction,
 // returning an error if the coordinate field is missing.
 func coordFromAction(action DesktopAction) (x, y int, err error) {

agent/x/agentdesktop/api_test.go

@@ -4,12 +4,22 @@ import (
 	"bytes"
 	"context"
 	"encoding/json"
+	"errors"
+	"fmt"
+	"io"
+	"mime"
+	"mime/multipart"
 	"net"
 	"net/http"
 	"net/http/httptest"
+	"os"
+	"slices"
+	"strings"
+	"sync"
 	"testing"
 	"time"
 
+	"github.com/google/uuid"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 	"golang.org/x/xerrors"
@@ -21,6 +31,16 @@ import (
 	"github.com/coder/quartz"
 )
 
+// Test recording UUIDs used across tests.
+const (
+	testRecIDDefault         = "870e1f02-8118-4300-a37e-4adb0117baf3"
+	testRecIDStartIdempotent = "250a2ffb-a5e5-4c94-9754-4d6a4ab7ba20"
+	testRecIDStopIdempotent  = "38f8a378-f98f-4758-a4ae-950b44cf989a"
+	testRecIDConcurrentA     = "8dc173eb-23c6-4601-a485-b6dfb2a42c3a"
+	testRecIDConcurrentB     = "fea490d4-70f0-4798-a181-29d65ce25ae1"
+	testRecIDRestart         = "75173a0d-b018-4e2e-a771-defa3fc6af69"
+)
+
 // Ensure fakeDesktop satisfies the Desktop interface at compile time.
 var _ agentdesktop.Desktop = (*fakeDesktop)(nil)
 
@@ -43,6 +63,16 @@ type fakeDesktop struct {
 	lastTyped   string
 	lastKeyDown string
 	lastKeyUp   string
+
+	thumbnailData []byte // if set, StopRecording includes a thumbnail
+
+	// Recording tracking (guarded by recMu).
+	recMu         sync.Mutex
+	recordings    map[string]string // ID → file path
+	stopCalls     []string          // recording IDs passed to StopRecording
+	recStopCh     chan string       // optional: signaled when StopRecording is called
+	startCount    int               // incremented on each new recording start
+	activityCount int               // incremented by RecordActivity
 }
 
 func (f *fakeDesktop) Start(context.Context) (agentdesktop.DisplayConfig, error) {
@@ -107,11 +137,145 @@ func (f *fakeDesktop) CursorPosition(context.Context) (x int, y int, err error)
 	return f.cursorPos[0], f.cursorPos[1], nil
 }
 
+func (f *fakeDesktop) StartRecording(_ context.Context, recordingID string) error {
+	f.recMu.Lock()
+	defer f.recMu.Unlock()
+	if f.recordings == nil {
+		f.recordings = make(map[string]string)
+	}
+	if path, ok := f.recordings[recordingID]; ok {
+		// Check if already stopped (file still exists but stop was
+		// called). For the fake, a stopped recording means its ID
+		// appears in stopCalls. In that case, remove the old file
+		// and start fresh.
+		stopped := slices.Contains(f.stopCalls, recordingID)
+		if !stopped {
+			// Active recording - no-op.
+			return nil
+		}
+		// Completed recording - discard old file, start fresh.
+		_ = os.Remove(path)
+		delete(f.recordings, recordingID)
+	}
+	f.startCount++
+	tmpFile, err := os.CreateTemp("", "fake-recording-*.mp4")
+	if err != nil {
+		return err
+	}
+	_, _ = tmpFile.Write([]byte(fmt.Sprintf("fake-mp4-data-%s-%d", recordingID, f.startCount)))
+	_ = tmpFile.Close()
+	f.recordings[recordingID] = tmpFile.Name()
+	return nil
+}
+
+func (f *fakeDesktop) StopRecording(_ context.Context, recordingID string) (*agentdesktop.RecordingArtifact, error) {
+	f.recMu.Lock()
+	defer f.recMu.Unlock()
+	if f.recordings == nil {
+		return nil, agentdesktop.ErrUnknownRecording
+	}
+	path, ok := f.recordings[recordingID]
+	if !ok {
+		return nil, agentdesktop.ErrUnknownRecording
+	}
+	f.stopCalls = append(f.stopCalls, recordingID)
+	if f.recStopCh != nil {
+		select {
+		case f.recStopCh <- recordingID:
+		default:
+		}
+	}
+	file, err := os.Open(path)
+	if err != nil {
+		return nil, err
+	}
+	info, err := file.Stat()
+	if err != nil {
+		_ = file.Close()
+		return nil, err
+	}
+	artifact := &agentdesktop.RecordingArtifact{
+		Reader: file,
+		Size:   info.Size(),
+	}
+	if f.thumbnailData != nil {
+		artifact.ThumbnailReader = io.NopCloser(bytes.NewReader(f.thumbnailData))
+		artifact.ThumbnailSize = int64(len(f.thumbnailData))
+	}
+	return artifact, nil
+}
+
+func (f *fakeDesktop) RecordActivity() {
+	f.recMu.Lock()
+	f.activityCount++
+	f.recMu.Unlock()
+}
+
 func (f *fakeDesktop) Close() error {
 	f.closed = true
+	f.recMu.Lock()
+	defer f.recMu.Unlock()
+	for _, path := range f.recordings {
+		_ = os.Remove(path)
+	}
 	return nil
 }
 
+// failStartRecordingDesktop wraps fakeDesktop and overrides
+// StartRecording to always return an error.
+type failStartRecordingDesktop struct {
+	fakeDesktop
+	startRecordingErr error
+}
+
+func (f *failStartRecordingDesktop) StartRecording(_ context.Context, _ string) error {
+	return f.startRecordingErr
+}
+
+// corruptedStopDesktop wraps fakeDesktop and overrides
+// StopRecording to always return ErrRecordingCorrupted.
+type corruptedStopDesktop struct {
+	fakeDesktop
+}
+
+func (*corruptedStopDesktop) StopRecording(_ context.Context, _ string) (*agentdesktop.RecordingArtifact, error) {
+	return nil, agentdesktop.ErrRecordingCorrupted
+}
+
+// oversizedFakeDesktop wraps fakeDesktop and expands recording files
+// beyond MaxRecordingSize when StopRecording is called.
+type oversizedFakeDesktop struct {
+	fakeDesktop
+}
+
+func (f *oversizedFakeDesktop) StopRecording(ctx context.Context, recordingID string) (*agentdesktop.RecordingArtifact, error) {
+	artifact, err := f.fakeDesktop.StopRecording(ctx, recordingID)
+	if err != nil {
+		return nil, err
+	}
+	// Close the original reader since we're going to re-open after truncation.
+	artifact.Reader.Close()
+
+	// Look up the path from the fakeDesktop recordings.
+	f.fakeDesktop.recMu.Lock()
+	path := f.fakeDesktop.recordings[recordingID]
+	f.fakeDesktop.recMu.Unlock()
+
+	// Expand the file to exceed the maximum recording size.
+	if err := os.Truncate(path, workspacesdk.MaxRecordingSize+1); err != nil {
+		return nil, err
+	}
+	// Re-open the truncated file.
+	file, err := os.Open(path)
+	if err != nil {
+		return nil, err
+	}
+	return &agentdesktop.RecordingArtifact{
+		Reader: file,
+		Size:   workspacesdk.MaxRecordingSize + 1,
+	}, nil
+}
+
 func TestHandleDesktopVNC_StartError(t *testing.T) {
 	t.Parallel()
 
@@ -134,6 +298,37 @@ func TestHandleDesktopVNC_StartError(t *testing.T) {
 	assert.Equal(t, "Failed to start desktop session.", resp.Message)
 }
 
+func TestHandleAction_CallsRecordActivity(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &fakeDesktop{
+		startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	body := agentdesktop.DesktopAction{
+		Action:     "left_click",
+		Coordinate: &[2]int{100, 200},
+	}
+	b, err := json.Marshal(body)
+	require.NoError(t, err)
+
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/action", bytes.NewReader(b))
+	req.Header.Set("Content-Type", "application/json")
+
+	handler := api.Routes()
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	fake.recMu.Lock()
+	count := fake.activityCount
+	fake.recMu.Unlock()
+	assert.Equal(t, 1, count, "handleAction should call RecordActivity exactly once")
+}
+
 func TestHandleAction_Screenshot(t *testing.T) {
 	t.Parallel()
 
@@ -574,3 +769,644 @@ func TestHandleAction_CursorPositionReturnsDeclaredCoordinates(t *testing.T) {
 	// Native (960,540) in 1920x1080 should map to declared space in 1280x720.
 	assert.Equal(t, "x=640,y=360", resp.Output)
 }
+
+func TestRecordingStartStop(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &fakeDesktop{
+		startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	// Start recording.
+	startBody, err := json.Marshal(map[string]string{"recording_id": testRecIDDefault})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(startBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Stop recording.
+	stopBody, err := json.Marshal(map[string]string{"recording_id": testRecIDDefault})
+	require.NoError(t, err)
+	rr = httptest.NewRecorder()
+	req = httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+	parts := parseMultipartParts(t, rr.Header().Get("Content-Type"), rr.Body.Bytes())
+	assert.Equal(t, []byte("fake-mp4-data-"+testRecIDDefault+"-1"), parts["video/mp4"])
+}
+
+func TestRecordingStartFails(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &failStartRecordingDesktop{
+		fakeDesktop: fakeDesktop{
+			startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+		},
+		startRecordingErr: xerrors.New("start recording error"),
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	body, err := json.Marshal(map[string]string{"recording_id": uuid.New().String()})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(body))
+	handler.ServeHTTP(rr, req)
+
+	assert.Equal(t, http.StatusInternalServerError, rr.Code)
+
+	var resp codersdk.Response
+	err = json.NewDecoder(rr.Body).Decode(&resp)
+	require.NoError(t, err)
+	assert.Equal(t, "Failed to start recording.", resp.Message)
+}
+
+func TestRecordingStartIdempotent(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &fakeDesktop{
+		startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	// Start same recording twice - both should succeed.
+	for range 2 {
+		body, err := json.Marshal(map[string]string{"recording_id": testRecIDStartIdempotent})
+		require.NoError(t, err)
+		rr := httptest.NewRecorder()
+		req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(body))
+		handler.ServeHTTP(rr, req)
+		require.Equal(t, http.StatusOK, rr.Code)
+	}
+
+	// Stop once, verify normal response.
+	stopBody, err := json.Marshal(map[string]string{"recording_id": testRecIDStartIdempotent})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+	parts := parseMultipartParts(t, rr.Header().Get("Content-Type"), rr.Body.Bytes())
+	assert.Equal(t, []byte("fake-mp4-data-"+testRecIDStartIdempotent+"-1"), parts["video/mp4"])
+}
+
+func TestRecordingStopIdempotent(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &fakeDesktop{
+		startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	// Start recording.
+	startBody, err := json.Marshal(map[string]string{"recording_id": testRecIDStopIdempotent})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(startBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Stop twice - both should succeed with identical data.
+	var videoParts [2][]byte
+	for i := range 2 {
+		body, err := json.Marshal(map[string]string{"recording_id": testRecIDStopIdempotent})
+		require.NoError(t, err)
+		recorder := httptest.NewRecorder()
+		request := httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(body))
+		handler.ServeHTTP(recorder, request)
+		require.Equal(t, http.StatusOK, recorder.Code)
+		parts := parseMultipartParts(t, recorder.Header().Get("Content-Type"), recorder.Body.Bytes())
+		videoParts[i] = parts["video/mp4"]
+	}
+	assert.Equal(t, videoParts[0], videoParts[1])
+}
+
+func TestRecordingStopInvalidIDFormat(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &fakeDesktop{
+		startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	body, err := json.Marshal(map[string]string{"recording_id": "not-a-uuid"})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(body))
+	handler.ServeHTTP(rr, req)
+	assert.Equal(t, http.StatusBadRequest, rr.Code)
+}
+
+func TestRecordingStopUnknownRecording(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &fakeDesktop{
+		startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	// Send a valid UUID that was never started - should reach
+	// StopRecording, get ErrUnknownRecording, and return 404.
+	body, err := json.Marshal(map[string]string{"recording_id": uuid.New().String()})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(body))
+	handler.ServeHTTP(rr, req)
+	assert.Equal(t, http.StatusNotFound, rr.Code)
+
+	var resp codersdk.Response
+	err = json.NewDecoder(rr.Body).Decode(&resp)
+	require.NoError(t, err)
+	assert.Equal(t, "Recording not found.", resp.Message)
+}
+
+func TestRecordingStopOversizedFile(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &oversizedFakeDesktop{
+		fakeDesktop: fakeDesktop{
+			startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+		},
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	// Start recording.
+	recID := uuid.New().String()
+	startBody, err := json.Marshal(map[string]string{"recording_id": recID})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(startBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Stop recording - file exceeds max size, expect 413.
+	stopBody, err := json.Marshal(map[string]string{"recording_id": recID})
+	require.NoError(t, err)
+	rr = httptest.NewRecorder()
+	req = httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
+	handler.ServeHTTP(rr, req)
+	assert.Equal(t, http.StatusRequestEntityTooLarge, rr.Code)
+
+	var resp codersdk.Response
+	err = json.NewDecoder(rr.Body).Decode(&resp)
+	require.NoError(t, err)
+	assert.Equal(t, "Recording file exceeds maximum allowed size.", resp.Message)
+}
+
+func TestRecordingMultipleSimultaneous(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &fakeDesktop{
+		startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	// Start two recordings with different IDs.
+	for _, id := range []string{testRecIDConcurrentA, testRecIDConcurrentB} {
+		body, err := json.Marshal(map[string]string{"recording_id": id})
+		require.NoError(t, err)
+		rr := httptest.NewRecorder()
+		req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(body))
+		handler.ServeHTTP(rr, req)
+		require.Equal(t, http.StatusOK, rr.Code)
+	}
+
+	// Stop both and verify each returns its own data.
+	expected := map[string][]byte{
+		testRecIDConcurrentA: []byte("fake-mp4-data-" + testRecIDConcurrentA + "-1"),
+		testRecIDConcurrentB: []byte("fake-mp4-data-" + testRecIDConcurrentB + "-2"),
+	}
+	for _, id := range []string{testRecIDConcurrentA, testRecIDConcurrentB} {
+		body, err := json.Marshal(map[string]string{"recording_id": id})
+		require.NoError(t, err)
+		rr := httptest.NewRecorder()
+		req := httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(body))
+		handler.ServeHTTP(rr, req)
+		require.Equal(t, http.StatusOK, rr.Code)
+		parts := parseMultipartParts(t, rr.Header().Get("Content-Type"), rr.Body.Bytes())
+		assert.Equal(t, expected[id], parts["video/mp4"])
+	}
+}
+
+func TestRecordingStartMalformedBody(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &fakeDesktop{
+		startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader([]byte("not json")))
+	handler.ServeHTTP(rr, req)
+	assert.Equal(t, http.StatusBadRequest, rr.Code)
+}
+
+func TestRecordingStartEmptyID(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &fakeDesktop{
+		startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	body, err := json.Marshal(map[string]string{"recording_id": ""})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(body))
+	handler.ServeHTTP(rr, req)
+	assert.Equal(t, http.StatusBadRequest, rr.Code)
+}
+
+func TestRecordingStopEmptyID(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &fakeDesktop{
+		startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	body, err := json.Marshal(map[string]string{"recording_id": ""})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(body))
+	handler.ServeHTTP(rr, req)
+	assert.Equal(t, http.StatusBadRequest, rr.Code)
+}
+
+func TestRecordingStopMalformedBody(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &fakeDesktop{
+		startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader([]byte("not json")))
+	handler.ServeHTTP(rr, req)
+	assert.Equal(t, http.StatusBadRequest, rr.Code)
+}
+
+func TestRecordingStartAfterCompleted(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &fakeDesktop{
+		startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	// Step 1: Start recording.
+	startBody, err := json.Marshal(map[string]string{"recording_id": testRecIDRestart})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(startBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Step 2: Stop recording (gets first MP4 data).
+	stopBody, err := json.Marshal(map[string]string{"recording_id": testRecIDRestart})
+	require.NoError(t, err)
+	rr = httptest.NewRecorder()
+	req = httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+	firstParts := parseMultipartParts(t, rr.Header().Get("Content-Type"), rr.Body.Bytes())
+	firstData := firstParts["video/mp4"]
+	require.NotEmpty(t, firstData)
+
+	// Step 3: Start again with the same ID - should succeed
+	// (old file discarded, new recording started).
+	rr = httptest.NewRecorder()
+	req = httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(startBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Step 4: Stop again - should return NEW MP4 data.
+	rr = httptest.NewRecorder()
+	req = httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+	secondParts := parseMultipartParts(t, rr.Header().Get("Content-Type"), rr.Body.Bytes())
+	secondData := secondParts["video/mp4"]
+	require.NotEmpty(t, secondData)
+
+	// The two recordings should have different data because the
+	// fake increments a counter on each fresh start.
+	assert.NotEqual(t, firstData, secondData,
+		"restarted recording should produce different data")
+}
+
+func TestRecordingStartAfterClose(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &fakeDesktop{
+		startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+
+	handler := api.Routes()
+
+	// Close the API before sending the request.
+	api.Close()
+
+	body, err := json.Marshal(map[string]string{"recording_id": uuid.New().String()})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(body))
+	handler.ServeHTTP(rr, req)
+
+	assert.Equal(t, http.StatusServiceUnavailable, rr.Code)
+
+	var resp codersdk.Response
+	err = json.NewDecoder(rr.Body).Decode(&resp)
+	require.NoError(t, err)
+	assert.Equal(t, "Desktop API is shutting down.", resp.Message)
+}
+
+func TestRecordingStartDesktopClosed(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	// StartRecording returns ErrDesktopClosed to simulate a race
+	// where the desktop is closed between the API-level check and
+	// the desktop-level StartRecording call.
+	fake := &failStartRecordingDesktop{
+		fakeDesktop: fakeDesktop{
+			startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+		},
+		startRecordingErr: agentdesktop.ErrDesktopClosed,
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	body, err := json.Marshal(map[string]string{"recording_id": uuid.New().String()})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(body))
+	handler.ServeHTTP(rr, req)
+
+	assert.Equal(t, http.StatusServiceUnavailable, rr.Code)
+
+	var resp codersdk.Response
+	err = json.NewDecoder(rr.Body).Decode(&resp)
+	require.NoError(t, err)
+	assert.Equal(t, "Desktop API is shutting down.", resp.Message)
+}
+
+func TestRecordingStopCorrupted(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &corruptedStopDesktop{
+		fakeDesktop: fakeDesktop{
+			startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+		},
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	// Start a recording so the stop has something to find.
+	recID := uuid.New().String()
+	startBody, err := json.Marshal(map[string]string{"recording_id": recID})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(startBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Stop returns ErrRecordingCorrupted.
+	stopBody, err := json.Marshal(map[string]string{"recording_id": recID})
+	require.NoError(t, err)
+	rr = httptest.NewRecorder()
+	req = httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
+	handler.ServeHTTP(rr, req)
+
+	assert.Equal(t, http.StatusInternalServerError, rr.Code)
+
+	var respStop codersdk.Response
+	err = json.NewDecoder(rr.Body).Decode(&respStop)
+	require.NoError(t, err)
+	assert.Equal(t, "Recording is corrupted.", respStop.Message)
+}
+
+// parseMultipartParts parses a multipart/mixed response and returns
+// a map from Content-Type to body bytes.
+func parseMultipartParts(t *testing.T, contentType string, body []byte) map[string][]byte {
+	t.Helper()
+	_, params, err := mime.ParseMediaType(contentType)
+	require.NoError(t, err, "parse Content-Type")
+	boundary := params["boundary"]
+	require.NotEmpty(t, boundary, "missing boundary")
+	mr := multipart.NewReader(bytes.NewReader(body), boundary)
+	parts := make(map[string][]byte)
+	for {
+		part, err := mr.NextPart()
+		if errors.Is(err, io.EOF) {
+			break
+		}
+		require.NoError(t, err, "unexpected multipart parse error")
+		ct := part.Header.Get("Content-Type")
+		data, readErr := io.ReadAll(part)
+		require.NoError(t, readErr)
+		parts[ct] = data
+	}
+	return parts
+}
+
+func TestHandleRecordingStop_WithThumbnail(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	// Create a fake JPEG header: 0xFF 0xD8 0xFF followed by 509 zero bytes.
+	thumbnail := make([]byte, 512)
+	thumbnail[0] = 0xff
+	thumbnail[1] = 0xd8
+	thumbnail[2] = 0xff
+
+	fake := &fakeDesktop{
+		startCfg:      agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+		thumbnailData: thumbnail,
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	// Start recording.
+	recID := uuid.New().String()
+	startBody, err := json.Marshal(map[string]string{"recording_id": recID})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(startBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Stop recording.
+	stopBody, err := json.Marshal(map[string]string{"recording_id": recID})
+	require.NoError(t, err)
+	rr = httptest.NewRecorder()
+	req = httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Verify multipart response.
+	ct := rr.Header().Get("Content-Type")
+	assert.True(t, strings.HasPrefix(ct, "multipart/mixed"),
+		"expected multipart/mixed Content-Type, got %s", ct)
+
+	parts := parseMultipartParts(t, ct, rr.Body.Bytes())
+	assert.Len(t, parts, 2, "expected exactly 2 parts (video + thumbnail)")
+
+	// The fake writes "fake-mp4-data-<id>-<counter>" as the MP4 content.
+	expectedMP4 := []byte("fake-mp4-data-" + recID + "-1")
+	assert.Equal(t, expectedMP4, parts["video/mp4"])
+	assert.Equal(t, thumbnail, parts["image/jpeg"])
+}
+
+func TestHandleRecordingStop_NoThumbnail(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &fakeDesktop{
+		startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	// Start recording.
+	recID := uuid.New().String()
+	startBody, err := json.Marshal(map[string]string{"recording_id": recID})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(startBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Stop recording.
+	stopBody, err := json.Marshal(map[string]string{"recording_id": recID})
+	require.NoError(t, err)
+	rr = httptest.NewRecorder()
+	req = httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Verify multipart response.
+	ct := rr.Header().Get("Content-Type")
+	assert.True(t, strings.HasPrefix(ct, "multipart/mixed"),
+		"expected multipart/mixed Content-Type, got %s", ct)
+
+	parts := parseMultipartParts(t, ct, rr.Body.Bytes())
+	assert.Len(t, parts, 1, "expected exactly 1 part (video only)")
+
+	expectedMP4 := []byte("fake-mp4-data-" + recID + "-1")
+	assert.Equal(t, expectedMP4, parts["video/mp4"])
+}
+
+func TestHandleRecordingStop_OversizedThumbnail(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	// Create thumbnail data that exceeds MaxThumbnailSize.
+	oversizedThumb := make([]byte, workspacesdk.MaxThumbnailSize+1)
+	oversizedThumb[0] = 0xff
+	oversizedThumb[1] = 0xd8
+	oversizedThumb[2] = 0xff
+
+	fake := &fakeDesktop{
+		startCfg:      agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+		thumbnailData: oversizedThumb,
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	// Start recording.
+	recID := uuid.New().String()
+	startBody, err := json.Marshal(map[string]string{"recording_id": recID})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(startBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Stop recording.
+	stopBody, err := json.Marshal(map[string]string{"recording_id": recID})
+	require.NoError(t, err)
+	rr = httptest.NewRecorder()
+	req = httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Verify multipart response contains only the video part.
+	ct := rr.Header().Get("Content-Type")
+	assert.True(t, strings.HasPrefix(ct, "multipart/mixed"),
+		"expected multipart/mixed Content-Type, got %s", ct)
+
+	parts := parseMultipartParts(t, ct, rr.Body.Bytes())
+	assert.Len(t, parts, 1, "expected exactly 1 part (video only, oversized thumbnail discarded)")
+
+	expectedMP4 := []byte("fake-mp4-data-" + recID + "-1")
+	assert.Equal(t, expectedMP4, parts["video/mp4"])
+}

agent/x/agentdesktop/desktop.go

@@ -2,7 +2,10 @@ package agentdesktop
 
 import (
 	"context"
+	"io"
 	"net"
+
+	"golang.org/x/xerrors"
 )
 
 // Desktop abstracts a virtual desktop session running inside a workspace.
@@ -58,10 +61,57 @@ type Desktop interface {
 	// CursorPosition returns the current cursor coordinates.
 	CursorPosition(ctx context.Context) (x, y int, err error)
 
+	// RecordActivity marks the desktop as having received user
+	// interaction, resetting the idle-recording timer.
+	RecordActivity()
+
+	// StartRecording begins recording the desktop to an MP4 file
+	// using the caller-provided recording ID. Safe to call
+	// repeatedly - active recordings continue unchanged, stopped
+	// recordings are discarded and restarted. Concurrent recordings
+	// are supported.
+	StartRecording(ctx context.Context, recordingID string) error
+
+	// StopRecording finalizes the recording identified by the given
+	// ID. Idempotent - safe to call on an already-stopped recording.
+	// Returns a RecordingArtifact that the caller can stream. The
+	// caller must close the artifact when done. Returns an error if
+	// the recording ID is unknown.
+	StopRecording(ctx context.Context, recordingID string) (*RecordingArtifact, error)
+
 	// Close shuts down the desktop session and cleans up resources.
 	Close() error
 }
 
+// ErrUnknownRecording is returned by StopRecording when the
+// recording ID is not recognized.
+var ErrUnknownRecording = xerrors.New("unknown recording ID")
+
+// ErrDesktopClosed is returned when an operation is attempted on a
+// closed desktop session.
+var ErrDesktopClosed = xerrors.New("desktop closed")
+
+// ErrRecordingCorrupted is returned by StopRecording when the
+// recording process was force-killed and the artifact is likely
+// incomplete or corrupt.
+var ErrRecordingCorrupted = xerrors.New("recording corrupted: process was force-killed")
+
+// RecordingArtifact is a finalized recording returned by StopRecording.
+// The caller streams the artifact and must call Close when done. The
+// artifact remains valid even if the same recording ID is restarted
+// or the desktop is closed while the caller is reading.
+type RecordingArtifact struct {
+	// Reader is the MP4 content. Callers must close it when done.
+	Reader io.ReadCloser
+	// Size is the byte length of the MP4 content.
+	Size int64
+	// ThumbnailReader is the JPEG thumbnail. May be nil if no
+	// thumbnail was produced. Callers must close it when done.
+	ThumbnailReader io.ReadCloser
+	// ThumbnailSize is the byte length of the thumbnail.
+	ThumbnailSize int64
+}
+
 // DisplayConfig describes a running desktop session.
 type DisplayConfig struct {
 	Width   int // native width in pixels

agent/x/agentdesktop/portabledesktop.go

@@ -3,6 +3,7 @@ package agentdesktop
 import (
 	"context"
 	"encoding/json"
+	"errors"
 	"fmt"
 	"net"
 	"os"
@@ -11,6 +12,7 @@ import (
 	"runtime"
 	"strconv"
 	"sync"
+	"sync/atomic"
 	"time"
 
 	"golang.org/x/xerrors"
@@ -18,6 +20,7 @@ import (
 	"cdr.dev/slog/v3"
 	"github.com/coder/coder/v2/agent/agentexec"
 	"github.com/coder/coder/v2/codersdk/workspacesdk"
+	"github.com/coder/quartz"
 )
 
 // portableDesktopOutput is the JSON output from
@@ -49,32 +52,66 @@ type screenshotOutput struct {
 	Data string `json:"data"`
 }
 
+// recordingProcess tracks a single desktop recording subprocess.
+type recordingProcess struct {
+	cmd        *exec.Cmd
+	filePath   string
+	thumbPath  string
+	stopped    bool
+	killed     bool          // true when the process was SIGKILLed
+	done       chan struct{} // closed when cmd.Wait() returns
+	waitErr    error         // set before done is closed
+	stopOnce   sync.Once
+	idleCancel context.CancelFunc // cancels the per-recording idle goroutine
+	idleDone   chan struct{}      // closed when idle goroutine exits
+}
+
+// maxConcurrentRecordings is the maximum number of active (non-stopped)
+// recordings allowed at once. This prevents resource exhaustion.
+const maxConcurrentRecordings = 5
+
+// idleTimeout is the duration of desktop inactivity after which all
+// active recordings are automatically stopped.
+const idleTimeout = 10 * time.Minute
+
 // portableDesktop implements Desktop by shelling out to the
 // portabledesktop CLI via agentexec.Execer.
 type portableDesktop struct {
 	logger       slog.Logger
 	execer       agentexec.Execer
 	scriptBinDir string // coder script bin directory
+	clock        quartz.Clock
 
-	mu      sync.Mutex
-	session *desktopSession // nil until started
-	binPath string          // resolved path to binary, cached
-	closed  bool
+	mu                  sync.Mutex
+	session             *desktopSession // nil until started
+	binPath             string          // resolved path to binary, cached
+	closed              bool
+	recordings          map[string]*recordingProcess // guarded by mu
+	lastDesktopActionAt atomic.Int64
 }
 
 // NewPortableDesktop creates a Desktop backed by the portabledesktop
 // CLI binary, using execer to spawn child processes. scriptBinDir is
-// the coder script bin directory checked for the binary.
+// the coder script bin directory checked for the binary. If clk is
+// nil, a real clock is used.
 func NewPortableDesktop(
 	logger slog.Logger,
 	execer agentexec.Execer,
 	scriptBinDir string,
+	clk quartz.Clock,
 ) Desktop {
-	return &portableDesktop{
+	if clk == nil {
+		clk = quartz.NewReal()
+	}
+	pd := &portableDesktop{
 		logger:       logger,
 		execer:       execer,
 		scriptBinDir: scriptBinDir,
+		clock:        clk,
+		recordings:   make(map[string]*recordingProcess),
 	}
+	pd.lastDesktopActionAt.Store(clk.Now().UnixNano())
+	return pd
 }
 
 // Start launches the desktop session (idempotent).
@@ -83,7 +120,7 @@ func (p *portableDesktop) Start(ctx context.Context) (DisplayConfig, error) {
 	defer p.mu.Unlock()
 
 	if p.closed {
-		return DisplayConfig{}, xerrors.New("desktop is closed")
+		return DisplayConfig{}, ErrDesktopClosed
 	}
 
 	if err := p.ensureBinary(ctx); err != nil {
@@ -313,23 +350,386 @@ func (p *portableDesktop) CursorPosition(ctx context.Context) (x int, y int, err
 	return result.X, result.Y, nil
 }
 
-// Close shuts down the desktop session and cleans up resources.
-func (p *portableDesktop) Close() error {
+// StartRecording begins recording the desktop to an MP4 file.
+// Three-state idempotency: active recordings are no-ops,
+// completed recordings are discarded and restarted.
+func (p *portableDesktop) StartRecording(ctx context.Context, recordingID string) error {
+	// Ensure the desktop session is running before acquiring the
+	// recording lock. Start is independently locked and idempotent.
+	if _, err := p.Start(ctx); err != nil {
+		return xerrors.Errorf("ensure desktop session: %w", err)
+	}
+
 	p.mu.Lock()
 	defer p.mu.Unlock()
 
+	if p.closed {
+		return ErrDesktopClosed
+	}
+
+	// Three-state idempotency:
+	// - Active recording → no-op, continue recording.
+	// - Completed recording → discard old file, start fresh.
+	// - Unknown ID → fall through to start a new recording.
+	if rec, ok := p.recordings[recordingID]; ok {
+		if !rec.stopped {
+			select {
+			case <-rec.done:
+				// Process exited unexpectedly; treat as completed
+				// so we fall through to discard the old file and
+				// restart.
+			default:
+				// Active recording - no-op, continue recording.
+				return nil
+			}
+		}
+		// Completed recording - discard old file, start fresh.
+		if err := os.Remove(rec.filePath); err != nil && !errors.Is(err, os.ErrNotExist) {
+			p.logger.Warn(ctx, "failed to remove old recording file",
+				slog.F("recording_id", recordingID),
+				slog.F("file_path", rec.filePath),
+				slog.Error(err),
+			)
+		}
+		if err := os.Remove(rec.thumbPath); err != nil && !errors.Is(err, os.ErrNotExist) {
+			p.logger.Warn(ctx, "failed to remove old thumbnail file",
+				slog.F("recording_id", recordingID),
+				slog.F("thumbnail_path", rec.thumbPath),
+				slog.Error(err),
+			)
+		}
+		delete(p.recordings, recordingID)
+	}
+
+	// Check concurrent recording limit.
+	if p.lockedActiveRecordingCount() >= maxConcurrentRecordings {
+		return xerrors.Errorf("too many concurrent recordings (max %d)", maxConcurrentRecordings)
+	}
+
+	// GC sweep: remove stopped recordings with stale files.
+	p.lockedCleanStaleRecordings(ctx)
+
+	if err := p.ensureBinary(ctx); err != nil {
+		return xerrors.Errorf("ensure portabledesktop binary: %w", err)
+	}
+
+	filePath := filepath.Join(os.TempDir(), "coder-recording-"+recordingID+".mp4")
+	thumbPath := filepath.Join(os.TempDir(), "coder-recording-"+recordingID+".thumb.jpg")
+
+	// Use a background context so the process outlives the HTTP
+	// request that triggered it.
+	procCtx, procCancel := context.WithCancel(context.Background())
+
+	//nolint:gosec // portabledesktop is a trusted binary resolved via ensureBinary.
+	cmd := p.execer.CommandContext(procCtx, p.binPath, "record",
+		// The following options are used to speed up the recording when the desktop is idle.
+		// They were taken out of an example in the portabledesktop repo.
+		// There's likely room for improvement to optimize the values.
+		"--idle-speedup", "20",
+		"--idle-min-duration", "0.35",
+		"--idle-noise-tolerance", "-38dB",
+		"--thumbnail", thumbPath,
+		filePath)
+
+	if err := cmd.Start(); err != nil {
+		procCancel()
+		return xerrors.Errorf("start recording process: %w", err)
+	}
+
+	rec := &recordingProcess{
+		cmd:       cmd,
+		filePath:  filePath,
+		thumbPath: thumbPath,
+		done:      make(chan struct{}),
+	}
+	go func() {
+		rec.waitErr = cmd.Wait()
+		close(rec.done)
+		// avoid a context resource leak by canceling the context
+		procCancel()
+	}()
+
+	p.recordings[recordingID] = rec
+
+	p.logger.Info(ctx, "started desktop recording",
+		slog.F("recording_id", recordingID),
+		slog.F("file_path", filePath),
+		slog.F("pid", cmd.Process.Pid),
+	)
+
+	// Record activity so a recording started on an already-idle
+	// desktop does not stop immediately.
+	p.lastDesktopActionAt.Store(p.clock.Now().UnixNano())
+
+	// Spawn a per-recording idle goroutine.
+	idleCtx, idleCancel := context.WithCancel(context.Background())
+	rec.idleCancel = idleCancel
+	rec.idleDone = make(chan struct{})
+	go func() {
+		defer close(rec.idleDone)
+		p.monitorRecordingIdle(idleCtx, rec)
+	}()
+
+	return nil
+}
+
+// StopRecording finalizes the recording. Idempotent - safe to call
+// on an already-stopped recording. Returns a RecordingArtifact
+// that the caller can stream. The caller must close the Reader
+// on the returned artifact to avoid leaking file descriptors.
+func (p *portableDesktop) StopRecording(ctx context.Context, recordingID string) (*RecordingArtifact, error) {
+	p.mu.Lock()
+	rec, ok := p.recordings[recordingID]
+	if !ok {
+		p.mu.Unlock()
+		return nil, ErrUnknownRecording
+	}
+
+	p.lockedStopRecordingProcess(ctx, rec, false)
+	killed := rec.killed
+	p.mu.Unlock()
+
+	p.logger.Info(ctx, "stopped desktop recording",
+		slog.F("recording_id", recordingID),
+		slog.F("file_path", rec.filePath),
+	)
+
+	if killed {
+		return nil, ErrRecordingCorrupted
+	}
+
+	// Open the file and return an artifact. Each call opens a fresh
+	// file descriptor so the caller is insulated from restarts and
+	// desktop close.
+	f, err := os.Open(rec.filePath)
+	if err != nil {
+		return nil, xerrors.Errorf("open recording artifact: %w", err)
+	}
+	info, err := f.Stat()
+	if err != nil {
+		_ = f.Close()
+		return nil, xerrors.Errorf("stat recording artifact: %w", err)
+	}
+	artifact := &RecordingArtifact{
+		Reader: f,
+		Size:   info.Size(),
+	}
+	// Attach thumbnail if the subprocess wrote one.
+	thumbFile, err := os.Open(rec.thumbPath)
+	if err != nil {
+		p.logger.Warn(ctx, "thumbnail not available",
+			slog.F("thumbnail_path", rec.thumbPath),
+			slog.Error(err))
+		return artifact, nil
+	}
+	thumbInfo, err := thumbFile.Stat()
+	if err != nil {
+		_ = thumbFile.Close()
+		p.logger.Warn(ctx, "thumbnail stat failed",
+			slog.F("thumbnail_path", rec.thumbPath),
+			slog.Error(err))
+		return artifact, nil
+	}
+	if thumbInfo.Size() == 0 {
+		_ = thumbFile.Close()
+		p.logger.Warn(ctx, "thumbnail file is empty",
+			slog.F("thumbnail_path", rec.thumbPath))
+		return artifact, nil
+	}
+	artifact.ThumbnailReader = thumbFile
+	artifact.ThumbnailSize = thumbInfo.Size()
+	return artifact, nil
+}
+
+// lockedStopRecordingProcess stops a single recording via stopOnce.
+// It sends SIGINT, waits up to 15 seconds for graceful exit, then
+// SIGKILLs. When force is true the process is SIGKILLed immediately
+// without attempting a graceful shutdown. Must be called while p.mu
+// is held; the lock is held for the full duration so that no
+// concurrent StopRecording caller can read rec.stopped = true
+// before the process has finished writing the MP4 file.
+//
+//nolint:revive // force flag keeps shared stopOnce/cleanup logic in one place.
+func (p *portableDesktop) lockedStopRecordingProcess(ctx context.Context, rec *recordingProcess, force bool) {
+	rec.stopOnce.Do(func() {
+		if force {
+			_ = rec.cmd.Process.Kill()
+			rec.killed = true
+		} else {
+			_ = interruptRecordingProcess(rec.cmd.Process)
+			timer := p.clock.NewTimer(15*time.Second, "agentdesktop", "stop_timeout")
+			defer timer.Stop()
+			select {
+			case <-rec.done:
+			case <-ctx.Done():
+				_ = rec.cmd.Process.Kill()
+				rec.killed = true
+			case <-timer.C:
+				_ = rec.cmd.Process.Kill()
+				rec.killed = true
+			}
+		}
+		rec.stopped = true
+		if rec.idleCancel != nil {
+			rec.idleCancel()
+		}
+	})
+	// NOTE: We intentionally do not wait on rec.done here.
+	// If goleak is added to this package's tests, this may
+	// need revisiting to avoid flakes.
+}
+
+// lockedActiveRecordingCount returns the number of recordings that
+// are still actively running. Must be called while p.mu is held.
+// The max concurrency is low (maxConcurrentRecordings = 5), so a
+// full scan is cheap and avoids maintaining a separate counter.
+func (p *portableDesktop) lockedActiveRecordingCount() int {
+	active := 0
+	for _, rec := range p.recordings {
+		if rec.stopped {
+			continue
+		}
+		select {
+		case <-rec.done:
+		default:
+			active++
+		}
+	}
+	return active
+}
+
+// lockedCleanStaleRecordings removes stopped recordings whose temp
+// files are older than one hour. Must be called while p.mu is held.
+func (p *portableDesktop) lockedCleanStaleRecordings(ctx context.Context) {
+	for id, rec := range p.recordings {
+		if !rec.stopped {
+			continue
+		}
+		info, err := os.Stat(rec.filePath)
+		if err != nil {
+			// File already removed or inaccessible; clean up
+			// any leftover thumbnail and drop the entry.
+			if err := os.Remove(rec.thumbPath); err != nil && !errors.Is(err, os.ErrNotExist) {
+				p.logger.Warn(ctx, "failed to remove stale thumbnail file",
+					slog.F("recording_id", id),
+					slog.F("thumbnail_path", rec.thumbPath),
+					slog.Error(err),
+				)
+			}
+			delete(p.recordings, id)
+			continue
+		}
+		if p.clock.Since(info.ModTime()) > time.Hour {
+			if err := os.Remove(rec.filePath); err != nil && !errors.Is(err, os.ErrNotExist) {
+				p.logger.Warn(ctx, "failed to remove stale recording file",
+					slog.F("recording_id", id),
+					slog.F("file_path", rec.filePath),
+					slog.Error(err),
+				)
+			}
+			if err := os.Remove(rec.thumbPath); err != nil && !errors.Is(err, os.ErrNotExist) {
+				p.logger.Warn(ctx, "failed to remove stale thumbnail file",
+					slog.F("recording_id", id),
+					slog.F("thumbnail_path", rec.thumbPath),
+					slog.Error(err),
+				)
+			}
+			delete(p.recordings, id)
+		}
+	}
+}
+
+// Close shuts down the desktop session and cleans up resources.
+func (p *portableDesktop) Close() error {
+	p.mu.Lock()
 	p.closed = true
-	if p.session != nil {
-		p.session.cancel()
-		// Xvnc is a child process — killing it cleans up the X
-		// session.
-		_ = p.session.cmd.Process.Kill()
-		_ = p.session.cmd.Wait()
-		p.session = nil
+
+	// Force-kill all active recordings. The stopOnce inside
+	// lockedStopRecordingProcess makes this safe for
+	// already-stopped recordings.
+	for _, rec := range p.recordings {
+		p.lockedStopRecordingProcess(context.Background(), rec, true)
+	}
+
+	// Snapshot recording file paths and idle goroutine channels
+	// for cleanup, then clear the map.
+	type recEntry struct {
+		id        string
+		filePath  string
+		thumbPath string
+		idleDone  chan struct{}
+	}
+	var allRecs []recEntry
+	for id, rec := range p.recordings {
+		allRecs = append(allRecs, recEntry{id: id, filePath: rec.filePath, thumbPath: rec.thumbPath, idleDone: rec.idleDone})
+		delete(p.recordings, id)
+	}
+	session := p.session
+	p.session = nil
+	p.mu.Unlock()
+
+	// Wait for all per-recording idle goroutines to exit.
+	for _, entry := range allRecs {
+		if entry.idleDone != nil {
+			<-entry.idleDone
+		}
+	}
+
+	// Remove all recording files and wait for the session to
+	// exit with a timeout so a slow filesystem or hung process
+	// cannot block agent shutdown indefinitely.
+	cleanupDone := make(chan struct{})
+	go func() {
+		defer close(cleanupDone)
+		for _, entry := range allRecs {
+			if err := os.Remove(entry.filePath); err != nil && !errors.Is(err, os.ErrNotExist) {
+				p.logger.Warn(context.Background(), "failed to remove recording file on close",
+					slog.F("recording_id", entry.id),
+					slog.F("file_path", entry.filePath),
+					slog.Error(err),
+				)
+			}
+			if err := os.Remove(entry.thumbPath); err != nil && !errors.Is(err, os.ErrNotExist) {
+				p.logger.Warn(context.Background(), "failed to remove thumbnail file on close",
+					slog.F("recording_id", entry.id),
+					slog.F("thumbnail_path", entry.thumbPath),
+					slog.Error(err),
+				)
+			}
+		}
+		if session != nil {
+			session.cancel()
+			if err := session.cmd.Process.Kill(); err != nil {
+				p.logger.Warn(context.Background(), "failed to kill portabledesktop process",
+					slog.Error(err),
+				)
+			}
+			if err := session.cmd.Wait(); err != nil {
+				var exitErr *exec.ExitError
+				if !errors.As(err, &exitErr) {
+					p.logger.Warn(context.Background(), "portabledesktop process exited with error",
+						slog.Error(err),
+					)
+				}
+			}
+		}
+	}()
+	timer := p.clock.NewTimer(15*time.Second, "agentdesktop", "close_cleanup_timeout")
+	defer timer.Stop()
+	select {
+	case <-cleanupDone:
+	case <-timer.C:
+		p.logger.Warn(context.Background(), "timed out waiting for close cleanup")
 	}
 	return nil
 }
 
+// RecordActivity marks the desktop as having received user
+// interaction, resetting the idle-recording timer.
+func (p *portableDesktop) RecordActivity() {
+	p.lastDesktopActionAt.Store(p.clock.Now().UnixNano())
+}
+
 // runCmd executes a portabledesktop subcommand and returns combined
 // output. The caller must have previously called ensureBinary.
 func (p *portableDesktop) runCmd(ctx context.Context, args ...string) (string, error) {
@@ -397,3 +797,31 @@ func (p *portableDesktop) ensureBinary(ctx context.Context) error {
 
 	return xerrors.New("portabledesktop binary not found in PATH or script bin directory")
 }
+
+// monitorRecordingIdle watches for desktop inactivity and stops the
+// given recording when the idle timeout is reached.
+func (p *portableDesktop) monitorRecordingIdle(ctx context.Context, rec *recordingProcess) {
+	timer := p.clock.NewTimer(idleTimeout, "agentdesktop", "recording_idle")
+	defer timer.Stop()
+
+	for {
+		select {
+		case <-timer.C:
+			lastNano := p.lastDesktopActionAt.Load()
+			lastAction := time.Unix(0, lastNano)
+			elapsed := p.clock.Since(lastAction)
+			if elapsed >= idleTimeout {
+				p.mu.Lock()
+				p.lockedStopRecordingProcess(context.Background(), rec, false)
+				p.mu.Unlock()
+				return
+			}
+			// Activity happened; reset with remaining budget.
+			timer.Reset(idleTimeout-elapsed, "agentdesktop", "recording_idle")
+		case <-rec.done:
+			return
+		case <-ctx.Done():
+			return
+		}
+	}
+}

agent/x/agentdesktop/portabledesktop_internal_test.go

@@ -2,6 +2,7 @@ package agentdesktop
 
 import (
 	"context"
+	"io"
 	"os"
 	"os/exec"
 	"path/filepath"
@@ -9,13 +10,17 @@ import (
 	"strings"
 	"sync"
 	"testing"
+	"time"
 
+	"github.com/google/uuid"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 
 	"cdr.dev/slog/v3/sloggers/slogtest"
 	"github.com/coder/coder/v2/agent/agentexec"
 	"github.com/coder/coder/v2/pty"
+	"github.com/coder/coder/v2/testutil"
+	"github.com/coder/quartz"
 )
 
 // recordedExecer implements agentexec.Execer by recording every
@@ -86,6 +91,7 @@ func TestPortableDesktop_Start_ParsesOutput(t *testing.T) {
 		execer:       rec,
 		scriptBinDir: t.TempDir(),
 		binPath:      "portabledesktop", // pre-set so ensureBinary is a no-op
+		clock:        quartz.NewReal(),
 	}
 
 	ctx := t.Context()
@@ -117,6 +123,7 @@ func TestPortableDesktop_Start_Idempotent(t *testing.T) {
 		execer:       rec,
 		scriptBinDir: t.TempDir(),
 		binPath:      "portabledesktop",
+		clock:        quartz.NewReal(),
 	}
 
 	ctx := t.Context()
@@ -159,6 +166,7 @@ func TestPortableDesktop_Screenshot(t *testing.T) {
 		execer:       rec,
 		scriptBinDir: t.TempDir(),
 		binPath:      "portabledesktop",
+		clock:        quartz.NewReal(),
 	}
 
 	ctx := t.Context()
@@ -184,6 +192,7 @@ func TestPortableDesktop_Screenshot_WithTargetDimensions(t *testing.T) {
 		execer:       rec,
 		scriptBinDir: t.TempDir(),
 		binPath:      "portabledesktop",
+		clock:        quartz.NewReal(),
 	}
 
 	ctx := t.Context()
@@ -282,6 +291,7 @@ func TestPortableDesktop_MouseMethods(t *testing.T) {
 				execer:       rec,
 				scriptBinDir: t.TempDir(),
 				binPath:      "portabledesktop",
+				clock:        quartz.NewReal(),
 			}
 
 			err := tt.invoke(t.Context(), pd)
@@ -289,7 +299,6 @@ func TestPortableDesktop_MouseMethods(t *testing.T) {
 
 			cmds := rec.allCommands()
 			require.NotEmpty(t, cmds, "expected at least one command")
-
 			// Find at least one recorded command that contains
 			// all expected argument substrings.
 			found := false
@@ -367,6 +376,7 @@ func TestPortableDesktop_KeyboardMethods(t *testing.T) {
 				execer:       rec,
 				scriptBinDir: t.TempDir(),
 				binPath:      "portabledesktop",
+				clock:        quartz.NewReal(),
 			}
 
 			err := tt.invoke(t.Context(), pd)
@@ -423,6 +433,7 @@ func TestPortableDesktop_Close(t *testing.T) {
 		execer:       rec,
 		scriptBinDir: t.TempDir(),
 		binPath:      "portabledesktop",
+		clock:        quartz.NewReal(),
 	}
 
 	ctx := t.Context()
@@ -445,7 +456,7 @@ func TestPortableDesktop_Close(t *testing.T) {
 	// Subsequent Start must fail.
 	_, err = pd.Start(ctx)
 	require.Error(t, err)
-	assert.Contains(t, err.Error(), "desktop is closed")
+	assert.Contains(t, err.Error(), "desktop closed")
 }
 
 // --- ensureBinary tests ---
@@ -539,7 +550,483 @@ func TestEnsureBinary_NotFound(t *testing.T) {
 	assert.Contains(t, err.Error(), "not found")
 }
 
+func TestPortableDesktop_StartRecording(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	rec := &recordedExecer{
+		scripts: map[string]string{
+			"record": `trap 'exit 0' INT; sleep 120 & wait`,
+			"up":     `printf '{"vncPort":5901,"geometry":"1920x1080"}\n' && sleep 120`,
+		},
+	}
+
+	clk := quartz.NewReal()
+	pd := &portableDesktop{
+		logger:       logger,
+		execer:       rec,
+		scriptBinDir: t.TempDir(),
+		clock:        clk,
+		binPath:      "portabledesktop",
+		recordings:   make(map[string]*recordingProcess),
+	}
+	pd.lastDesktopActionAt.Store(clk.Now().UnixNano())
+
+	ctx := t.Context()
+	recID := uuid.New().String()
+	err := pd.StartRecording(ctx, recID)
+	require.NoError(t, err)
+
+	cmds := rec.allCommands()
+	require.NotEmpty(t, cmds)
+	// Find the record command (not the up command).
+	found := false
+	for _, cmd := range cmds {
+		joined := strings.Join(cmd, " ")
+		if strings.Contains(joined, "record") && strings.Contains(joined, "coder-recording-"+recID) {
+			found = true
+			assert.Contains(t, joined, "--thumbnail", "record command should include --thumbnail flag")
+			break
+		}
+	}
+	assert.True(t, found, "expected a record command with the recording ID")
+
+	require.NoError(t, pd.Close())
+}
+
+func TestPortableDesktop_StartRecording_ConcurrentLimit(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	rec := &recordedExecer{
+		scripts: map[string]string{
+			"record": `trap 'exit 0' INT; sleep 120 & wait`,
+			"up":     `printf '{"vncPort":5901,"geometry":"1920x1080"}\n' && sleep 120`,
+		},
+	}
+
+	clk := quartz.NewReal()
+	pd := &portableDesktop{
+		logger:       logger,
+		execer:       rec,
+		scriptBinDir: t.TempDir(),
+		clock:        clk,
+		binPath:      "portabledesktop",
+		recordings:   make(map[string]*recordingProcess),
+	}
+	pd.lastDesktopActionAt.Store(clk.Now().UnixNano())
+
+	ctx := t.Context()
+
+	for i := range maxConcurrentRecordings {
+		err := pd.StartRecording(ctx, uuid.New().String())
+		require.NoError(t, err, "recording %d should succeed", i)
+	}
+
+	err := pd.StartRecording(ctx, uuid.New().String())
+	require.Error(t, err)
+	assert.Contains(t, err.Error(), "too many concurrent recordings")
+
+	require.NoError(t, pd.Close())
+}
+
+func TestPortableDesktop_StopRecording_ReturnsArtifact(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	rec := &recordedExecer{
+		scripts: map[string]string{
+			"record": `trap 'exit 0' INT; sleep 120 & wait`,
+			"up":     `printf '{"vncPort":5901,"geometry":"1920x1080"}\n' && sleep 120`,
+		},
+	}
+
+	clk := quartz.NewReal()
+	pd := &portableDesktop{
+		logger:       logger,
+		execer:       rec,
+		scriptBinDir: t.TempDir(),
+		clock:        clk,
+		binPath:      "portabledesktop",
+		recordings:   make(map[string]*recordingProcess),
+	}
+	pd.lastDesktopActionAt.Store(clk.Now().UnixNano())
+
+	ctx := t.Context()
+	recID := uuid.New().String()
+	err := pd.StartRecording(ctx, recID)
+	require.NoError(t, err)
+
+	// Write a dummy MP4 file at the expected path so StopRecording
+	// can open it as an artifact.
+	filePath := filepath.Join(os.TempDir(), "coder-recording-"+recID+".mp4")
+	require.NoError(t, os.WriteFile(filePath, []byte("fake-mp4-data"), 0o600))
+	t.Cleanup(func() { _ = os.Remove(filePath) })
+
+	artifact, err := pd.StopRecording(ctx, recID)
+	require.NoError(t, err)
+	defer artifact.Reader.Close()
+	assert.Equal(t, int64(len("fake-mp4-data")), artifact.Size)
+
+	// No thumbnail file exists, so ThumbnailReader should be nil.
+	assert.Nil(t, artifact.ThumbnailReader, "ThumbnailReader should be nil when no thumbnail file exists")
+
+	require.NoError(t, pd.Close())
+}
+
+func TestPortableDesktop_StopRecording_WithThumbnail(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	rec := &recordedExecer{
+		scripts: map[string]string{
+			"record": `trap 'exit 0' INT; sleep 120 & wait`,
+			"up":     `printf '{"vncPort":5901,"geometry":"1920x1080"}\n' && sleep 120`,
+		},
+	}
+
+	clk := quartz.NewReal()
+	pd := &portableDesktop{
+		logger:       logger,
+		execer:       rec,
+		scriptBinDir: t.TempDir(),
+		clock:        clk,
+		binPath:      "portabledesktop",
+		recordings:   make(map[string]*recordingProcess),
+	}
+	pd.lastDesktopActionAt.Store(clk.Now().UnixNano())
+
+	ctx := t.Context()
+	recID := uuid.New().String()
+	err := pd.StartRecording(ctx, recID)
+	require.NoError(t, err)
+
+	// Write a dummy MP4 file at the expected path.
+	filePath := filepath.Join(os.TempDir(), "coder-recording-"+recID+".mp4")
+	require.NoError(t, os.WriteFile(filePath, []byte("fake-mp4-data"), 0o600))
+	t.Cleanup(func() { _ = os.Remove(filePath) })
+
+	// Write a thumbnail file at the expected path.
+	thumbPath := filepath.Join(os.TempDir(), "coder-recording-"+recID+".thumb.jpg")
+	thumbContent := []byte("fake-jpeg-thumbnail")
+	require.NoError(t, os.WriteFile(thumbPath, thumbContent, 0o600))
+	t.Cleanup(func() { _ = os.Remove(thumbPath) })
+
+	artifact, err := pd.StopRecording(ctx, recID)
+	require.NoError(t, err)
+	defer artifact.Reader.Close()
+
+	assert.Equal(t, int64(len("fake-mp4-data")), artifact.Size)
+
+	// Thumbnail should be attached.
+	require.NotNil(t, artifact.ThumbnailReader, "ThumbnailReader should be non-nil when thumbnail file exists")
+	defer artifact.ThumbnailReader.Close()
+	assert.Equal(t, int64(len(thumbContent)), artifact.ThumbnailSize)
+
+	// Read and verify thumbnail content.
+	thumbData, err := io.ReadAll(artifact.ThumbnailReader)
+	require.NoError(t, err)
+	assert.Equal(t, thumbContent, thumbData)
+
+	require.NoError(t, pd.Close())
+}
+
+func TestPortableDesktop_StopRecording_UnknownID(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	rec := &recordedExecer{
+		scripts: map[string]string{
+			"record": `trap 'exit 0' INT; sleep 120 & wait`,
+		},
+	}
+
+	clk := quartz.NewReal()
+	pd := &portableDesktop{
+		logger:       logger,
+		execer:       rec,
+		scriptBinDir: t.TempDir(),
+		clock:        clk,
+		binPath:      "portabledesktop",
+		recordings:   make(map[string]*recordingProcess),
+	}
+	pd.lastDesktopActionAt.Store(clk.Now().UnixNano())
+
+	ctx := t.Context()
+	_, err := pd.StopRecording(ctx, uuid.New().String())
+	require.ErrorIs(t, err, ErrUnknownRecording)
+
+	require.NoError(t, pd.Close())
+}
+
 // Ensure that portableDesktop satisfies the Desktop interface at
 // compile time. This uses the unexported type so it lives in the
 // internal test package.
 var _ Desktop = (*portableDesktop)(nil)
+
+func TestPortableDesktop_IdleTimeout_StopsRecordings(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	rec := &recordedExecer{
+		scripts: map[string]string{
+			"record": `trap 'exit 0' INT; sleep 120 & wait`,
+			"up":     `printf '{"vncPort":5901,"geometry":"1920x1080"}\n' && sleep 120`,
+		},
+	}
+
+	clk := quartz.NewMock(t)
+	pd := &portableDesktop{
+		logger:       logger,
+		execer:       rec,
+		scriptBinDir: t.TempDir(),
+		clock:        clk,
+		binPath:      "portabledesktop",
+		recordings:   make(map[string]*recordingProcess),
+	}
+	pd.lastDesktopActionAt.Store(clk.Now().UnixNano())
+
+	ctx := t.Context()
+	recID := uuid.New().String()
+
+	// Install the trap before StartRecording so it is guaranteed
+	// to catch the idle monitor's NewTimer call regardless of
+	// goroutine scheduling.
+	trap := clk.Trap().NewTimer("agentdesktop", "recording_idle")
+
+	err := pd.StartRecording(ctx, recID)
+	require.NoError(t, err)
+
+	// Verify recording is active.
+	pd.mu.Lock()
+	require.False(t, pd.recordings[recID].stopped)
+	pd.mu.Unlock()
+
+	// Wait for the idle monitor timer to be created and release
+	// it so the monitor enters its select loop.
+	trap.MustWait(ctx).MustRelease(ctx)
+	trap.Close()
+
+	// The stop-all path calls lockedStopRecordingProcess which
+	// creates a per-recording 15s stop_timeout timer.
+	stopTrap := clk.Trap().NewTimer("agentdesktop", "stop_timeout")
+
+	// Advance past idle timeout to trigger the stop-all.
+	clk.Advance(idleTimeout).MustWait(ctx)
+
+	// Wait for the stop timer to be created, then release it.
+	stopTrap.MustWait(ctx).MustRelease(ctx)
+	stopTrap.Close()
+
+	// Advance past the 15s stop timeout so the process is
+	// forcibly killed. Without this the test depends on the real
+	// shell handling SIGINT promptly, which is unreliable on
+	// macOS CI runners (the flake in #1461).
+	clk.Advance(15 * time.Second).MustWait(ctx)
+
+	// The recording process should now be stopped.
+	require.Eventually(t, func() bool {
+		pd.mu.Lock()
+		defer pd.mu.Unlock()
+		rec, ok := pd.recordings[recID]
+		return ok && rec.stopped
+	}, testutil.WaitShort, testutil.IntervalFast)
+
+	require.NoError(t, pd.Close())
+}
+
+func TestPortableDesktop_IdleTimeout_ActivityResetsTimer(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	rec := &recordedExecer{
+		scripts: map[string]string{
+			"record": `trap 'exit 0' INT; sleep 120 & wait`,
+			"up":     `printf '{"vncPort":5901,"geometry":"1920x1080"}\n' && sleep 120`,
+		},
+	}
+
+	clk := quartz.NewMock(t)
+	pd := &portableDesktop{
+		logger:       logger,
+		execer:       rec,
+		scriptBinDir: t.TempDir(),
+		clock:        clk,
+		binPath:      "portabledesktop",
+		recordings:   make(map[string]*recordingProcess),
+	}
+	pd.lastDesktopActionAt.Store(clk.Now().UnixNano())
+
+	ctx := t.Context()
+	recID := uuid.New().String()
+
+	// Install the trap before StartRecording so it is guaranteed
+	// to catch the idle monitor's NewTimer call regardless of
+	// goroutine scheduling.
+	trap := clk.Trap().NewTimer("agentdesktop", "recording_idle")
+
+	err := pd.StartRecording(ctx, recID)
+	require.NoError(t, err)
+
+	// Wait for the idle monitor timer to be created.
+	trap.MustWait(ctx).MustRelease(ctx)
+	trap.Close()
+
+	// Advance most of the way but not past the timeout.
+	clk.Advance(idleTimeout - time.Minute)
+
+	// Record activity to reset the timer.
+	pd.RecordActivity()
+
+	// Trap the Reset call that the idle monitor makes when it
+	// sees recent activity.
+	resetTrap := clk.Trap().TimerReset("agentdesktop", "recording_idle")
+
+	// Advance past the original idle timeout deadline. The
+	// monitor should see the recent activity and reset instead
+	// of stopping.
+	clk.Advance(time.Minute)
+
+	resetTrap.MustWait(ctx).MustRelease(ctx)
+	resetTrap.Close()
+
+	// Recording should still be active because activity was
+	// recorded.
+	pd.mu.Lock()
+	require.False(t, pd.recordings[recID].stopped)
+	pd.mu.Unlock()
+
+	require.NoError(t, pd.Close())
+}
+
+func TestPortableDesktop_IdleTimeout_MultipleRecordings(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	rec := &recordedExecer{
+		scripts: map[string]string{
+			"record": `trap 'exit 0' INT; sleep 120 & wait`,
+			"up":     `printf '{"vncPort":5901,"geometry":"1920x1080"}\n' && sleep 120`,
+		},
+	}
+
+	clk := quartz.NewMock(t)
+	pd := &portableDesktop{
+		logger:       logger,
+		execer:       rec,
+		scriptBinDir: t.TempDir(),
+		clock:        clk,
+		binPath:      "portabledesktop",
+		recordings:   make(map[string]*recordingProcess),
+	}
+	pd.lastDesktopActionAt.Store(clk.Now().UnixNano())
+
+	ctx := t.Context()
+	recID1 := uuid.New().String()
+	recID2 := uuid.New().String()
+
+	// Trap idle timer creation for both recordings.
+	trap := clk.Trap().NewTimer("agentdesktop", "recording_idle")
+
+	err := pd.StartRecording(ctx, recID1)
+	require.NoError(t, err)
+
+	// Wait for first recording's idle timer.
+	trap.MustWait(ctx).MustRelease(ctx)
+
+	err = pd.StartRecording(ctx, recID2)
+	require.NoError(t, err)
+
+	// Wait for second recording's idle timer.
+	trap.MustWait(ctx).MustRelease(ctx)
+	trap.Close()
+
+	// Trap the stop timers that will be created when idle fires.
+	stopTrap := clk.Trap().NewTimer("agentdesktop", "stop_timeout")
+
+	// Advance past idle timeout.
+	clk.Advance(idleTimeout).MustWait(ctx)
+
+	// Each idle monitor goroutine serializes on p.mu, so the
+	// second stop timer is only created after the first stop
+	// completes. Advance past the 15s stop timeout after each
+	// release so the process is forcibly killed instead of
+	// depending on SIGINT (unreliable on macOS — see #1461).
+	stopTrap.MustWait(ctx).MustRelease(ctx)
+	clk.Advance(15 * time.Second).MustWait(ctx)
+	stopTrap.MustWait(ctx).MustRelease(ctx)
+	clk.Advance(15 * time.Second).MustWait(ctx)
+	stopTrap.Close()
+
+	// Both recordings should be stopped.
+	require.Eventually(t, func() bool {
+		pd.mu.Lock()
+		defer pd.mu.Unlock()
+		r1, ok1 := pd.recordings[recID1]
+		r2, ok2 := pd.recordings[recID2]
+		return ok1 && r1.stopped && ok2 && r2.stopped
+	}, testutil.WaitShort, testutil.IntervalFast)
+
+	require.NoError(t, pd.Close())
+}
+
+func TestPortableDesktop_StartRecording_ReturnsErrDesktopClosed(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	rec := &recordedExecer{
+		scripts: map[string]string{
+			"up": `printf '{"vncPort":5901,"geometry":"1920x1080"}\n' && sleep 120`,
+		},
+	}
+
+	clk := quartz.NewReal()
+	pd := &portableDesktop{
+		logger:       logger,
+		execer:       rec,
+		scriptBinDir: t.TempDir(),
+		clock:        clk,
+		binPath:      "portabledesktop",
+		recordings:   make(map[string]*recordingProcess),
+	}
+	pd.lastDesktopActionAt.Store(clk.Now().UnixNano())
+
+	// Start and close the desktop so it's in the closed state.
+	ctx := t.Context()
+	_, err := pd.Start(ctx)
+	require.NoError(t, err)
+	require.NoError(t, pd.Close())
+
+	// StartRecording should now return ErrDesktopClosed.
+	err = pd.StartRecording(ctx, uuid.New().String())
+	require.ErrorIs(t, err, ErrDesktopClosed)
+}
+
+func TestPortableDesktop_Start_ReturnsErrDesktopClosed(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	rec := &recordedExecer{
+		scripts: map[string]string{
+			"up": `printf '{"vncPort":5901,"geometry":"1920x1080"}\n' && sleep 120`,
+		},
+	}
+
+	pd := &portableDesktop{
+		logger:       logger,
+		execer:       rec,
+		scriptBinDir: t.TempDir(),
+		clock:        quartz.NewReal(),
+		binPath:      "portabledesktop",
+		recordings:   make(map[string]*recordingProcess),
+	}
+	pd.lastDesktopActionAt.Store(pd.clock.Now().UnixNano())
+
+	ctx := t.Context()
+	_, err := pd.Start(ctx)
+	require.NoError(t, err)
+	require.NoError(t, pd.Close())
+
+	_, err = pd.Start(ctx)
+	require.ErrorIs(t, err, ErrDesktopClosed)
+}

agent/x/agentdesktop/portabledesktop_stop_other.go

@@ -0,0 +1,12 @@
+//go:build !windows
+
+package agentdesktop
+
+import "os"
+
+// interruptRecordingProcess sends a SIGINT to the recording process
+// for graceful shutdown. On Unix, os.Interrupt is delivered as
+// SIGINT which lets the recorder finalize the MP4 container.
+func interruptRecordingProcess(p *os.Process) error {
+	return p.Signal(os.Interrupt)
+}

agent/x/agentdesktop/portabledesktop_stop_windows.go

@@ -0,0 +1,10 @@
+package agentdesktop
+
+import "os"
+
+// interruptRecordingProcess kills the recording process directly
+// because os.Process.Signal(os.Interrupt) is not supported on
+// Windows and returns an error without delivering a signal.
+func interruptRecordingProcess(p *os.Process) error {
+	return p.Kill()
+}

agent/x/agentmcp/manager.go

@@ -6,7 +6,6 @@ import (
 	"fmt"
 	"io/fs"
 	"os"
-	"path/filepath"
 	"slices"
 	"strings"
 	"sync"
@@ -70,16 +69,40 @@ func NewManager(logger slog.Logger) *Manager {
 	}
 }
 
-// Connect discovers .mcp.json in dir and connects to all
-// configured servers. Failed servers are logged and skipped.
-func (m *Manager) Connect(ctx context.Context, dir string) error {
-	path := filepath.Join(dir, ".mcp.json")
-	configs, err := ParseConfig(path)
-	if err != nil {
-		if errors.Is(err, fs.ErrNotExist) {
-			return nil
+// Connect reads MCP config files at the given absolute paths and
+// connects to all configured servers. Failed servers are logged
+// and skipped. Missing config files are silently skipped.
+func (m *Manager) Connect(ctx context.Context, mcpConfigFiles []string) error {
+	var allConfigs []ServerConfig
+	for _, configPath := range mcpConfigFiles {
+		configs, err := ParseConfig(configPath)
+		if err != nil {
+			if errors.Is(err, fs.ErrNotExist) {
+				continue
+			}
+			m.logger.Warn(ctx, "failed to parse MCP config",
+				slog.F("path", configPath),
+				slog.Error(err),
+			)
+			continue
 		}
-		return xerrors.Errorf("parse mcp config: %w", err)
+		allConfigs = append(allConfigs, configs...)
+	}
+
+	// Deduplicate by server name; first occurrence wins.
+	seen := make(map[string]struct{})
+	deduped := make([]ServerConfig, 0, len(allConfigs))
+	for _, cfg := range allConfigs {
+		if _, ok := seen[cfg.Name]; ok {
+			continue
+		}
+		seen[cfg.Name] = struct{}{}
+		deduped = append(deduped, cfg)
+	}
+	allConfigs = deduped
+
+	if len(allConfigs) == 0 {
+		return nil
 	}
 
 	// Connect to servers in parallel without holding the
@@ -95,7 +118,7 @@ func (m *Manager) Connect(ctx context.Context, dir string) error {
 		connected []connectedServer
 	)
 	var eg errgroup.Group
-	for _, cfg := range configs {
+	for _, cfg := range allConfigs {
 		eg.Go(func() error {
 			c, err := m.connectServer(ctx, cfg)
 			if err != nil {
@@ -164,7 +187,11 @@ func (*Manager) connectServer(ctx context.Context, cfg ServerConfig) (*client.Cl
 	connectCtx, cancel := context.WithTimeout(ctx, connectTimeout)
 	defer cancel()
 
-	if err := c.Start(connectCtx); err != nil {
+	// Use the parent ctx (not connectCtx) so the subprocess outlives
+	// the connect/initialize handshake. connectCtx bounds only the
+	// Initialize call below. The subprocess is cleaned up when the
+	// Manager is closed or ctx is canceled.
+	if err := c.Start(ctx); err != nil {
 		_ = c.Close()
 		return nil, xerrors.Errorf("start %q: %w", cfg.Name, err)
 	}

agent/x/agentmcp/manager_internal_test.go

@@ -1,6 +1,11 @@
 package agentmcp
 
 import (
+	"bufio"
+	"context"
+	"encoding/json"
+	"fmt"
+	"os"
 	"testing"
 
 	"github.com/mark3labs/mcp-go/mcp"
@@ -8,6 +13,7 @@ import (
 	"github.com/stretchr/testify/require"
 
 	"github.com/coder/coder/v2/codersdk/workspacesdk"
+	"github.com/coder/coder/v2/testutil"
 )
 
 func TestSplitToolName(t *testing.T) {
@@ -193,3 +199,118 @@ func TestConvertResult(t *testing.T) {
 		})
 	}
 }
+
+// TestConnectServer_StdioProcessSurvivesConnect verifies that a stdio MCP
+// server subprocess remains alive after connectServer returns. This is a
+// regression test for a bug where the subprocess was tied to a short-lived
+// connectCtx and killed as soon as the context was canceled.
+func TestConnectServer_StdioProcessSurvivesConnect(t *testing.T) {
+	t.Parallel()
+
+	if os.Getenv("TEST_MCP_FAKE_SERVER") == "1" {
+		// Child process: act as a minimal MCP server over stdio.
+		runFakeMCPServer()
+		return
+	}
+
+	// Get the path to the test binary so we can re-exec ourselves
+	// as a fake MCP server subprocess.
+	testBin, err := os.Executable()
+	require.NoError(t, err)
+
+	cfg := ServerConfig{
+		Name:      "fake",
+		Transport: "stdio",
+		Command:   testBin,
+		Args:      []string{"-test.run=^TestConnectServer_StdioProcessSurvivesConnect$"},
+		Env:       map[string]string{"TEST_MCP_FAKE_SERVER": "1"},
+	}
+
+	ctx := testutil.Context(t, testutil.WaitLong)
+	m := &Manager{}
+	client, err := m.connectServer(ctx, cfg)
+	require.NoError(t, err, "connectServer should succeed")
+	t.Cleanup(func() { _ = client.Close() })
+
+	// At this point connectServer has returned and its internal
+	// connectCtx has been canceled. The subprocess must still be
+	// alive. Verify by listing tools (requires a live server).
+	listCtx, listCancel := context.WithTimeout(ctx, testutil.WaitShort)
+	defer listCancel()
+	result, err := client.ListTools(listCtx, mcp.ListToolsRequest{})
+	require.NoError(t, err, "ListTools should succeed — server must be alive after connect")
+	require.Len(t, result.Tools, 1)
+	assert.Equal(t, "echo", result.Tools[0].Name)
+}
+
+// runFakeMCPServer implements a minimal JSON-RPC / MCP server over
+// stdin/stdout, just enough for initialize + tools/list.
+func runFakeMCPServer() {
+	scanner := bufio.NewScanner(os.Stdin)
+	for scanner.Scan() {
+		line := scanner.Bytes()
+
+		var req struct {
+			JSONRPC string          `json:"jsonrpc"`
+			ID      json.RawMessage `json:"id"`
+			Method  string          `json:"method"`
+		}
+		if err := json.Unmarshal(line, &req); err != nil {
+			continue
+		}
+
+		var resp any
+		switch req.Method {
+		case "initialize":
+			resp = map[string]any{
+				"jsonrpc": "2.0",
+				"id":      req.ID,
+				"result": map[string]any{
+					"protocolVersion": "2025-03-26",
+					"capabilities": map[string]any{
+						"tools": map[string]any{},
+					},
+					"serverInfo": map[string]any{
+						"name":    "fake-server",
+						"version": "0.0.1",
+					},
+				},
+			}
+		case "notifications/initialized":
+			// No response needed for notifications.
+			continue
+		case "tools/list":
+			resp = map[string]any{
+				"jsonrpc": "2.0",
+				"id":      req.ID,
+				"result": map[string]any{
+					"tools": []map[string]any{
+						{
+							"name":        "echo",
+							"description": "echoes input",
+							"inputSchema": map[string]any{
+								"type":       "object",
+								"properties": map[string]any{},
+							},
+						},
+					},
+				},
+			}
+		default:
+			resp = map[string]any{
+				"jsonrpc": "2.0",
+				"id":      req.ID,
+				"error": map[string]any{
+					"code":    -32601,
+					"message": "method not found",
+				},
+			}
+		}
+
+		out, err := json.Marshal(resp)
+		if err != nil {
+			continue
+		}
+		_, _ = fmt.Fprintf(os.Stdout, "%s\n", out)
+	}
+}

biome.jsonc

@@ -3,11 +3,13 @@
 		"enabled": true,
 		"clientKind": "git",
 		"useIgnoreFile": true,
-		"defaultBranch": "main",
+		"defaultBranch": "main"
 	},
 	"files": {
-		"includes": ["**", "!**/pnpm-lock.yaml"],
-		"ignoreUnknown": true,
+		// static/*.html are Go templates with {{ }} directives that
+		// Biome's HTML parser does not support.
+		"includes": ["**", "!**/pnpm-lock.yaml", "!**/static/*.html"],
+		"ignoreUnknown": true
 	},
 	"linter": {
 		"rules": {
@@ -15,7 +17,7 @@
 				"noSvgWithoutTitle": "off",
 				"useButtonType": "off",
 				"useSemanticElements": "off",
-				"noStaticElementInteractions": "off",
+				"noStaticElementInteractions": "off"
 			},
 			"correctness": {
 				"noUnusedImports": "warn",
@@ -24,9 +26,9 @@
 				"noUnusedVariables": {
 					"level": "warn",
 					"options": {
-						"ignoreRestSiblings": true,
-					},
-				},
+						"ignoreRestSiblings": true
+					}
+				}
 			},
 			"style": {
 				"noNonNullAssertion": "off",
@@ -47,7 +49,7 @@
 						"paths": {
 							"react": {
 								"message": "React 19 no longer requires forwardRef. Use ref as a prop instead.",
-								"importNames": ["forwardRef"],
+								"importNames": ["forwardRef"]
 							},
 							// "@mui/material/Alert": "Use components/Alert/Alert instead.",
 							// "@mui/material/AlertTitle": "Use components/Alert/Alert instead.",
@@ -115,10 +117,10 @@
 							"@emotion/styled": "Use Tailwind CSS instead.",
 							// "@emotion/cache": "Use Tailwind CSS instead.",
 							// "components/Stack/Stack": "Use Tailwind flex utilities instead (e.g., <div className='flex flex-col gap-4'>).",
-							"lodash": "Use lodash/<name> instead.",
-						},
-					},
-				},
+							"lodash": "Use lodash/<name> instead."
+						}
+					}
+				}
 			},
 			"suspicious": {
 				"noArrayIndexKey": "off",
@@ -129,14 +131,21 @@
 				"noConsole": {
 					"level": "error",
 					"options": {
-						"allow": ["error", "info", "warn"],
-					},
-				},
+						"allow": ["error", "info", "warn"]
+					}
+				}
 			},
 			"complexity": {
-				"noImportantStyles": "off", // TODO: check and fix !important styles
-			},
-		},
+				"noImportantStyles": "off" // TODO: check and fix !important styles
+			}
+		}
 	},
-	"$schema": "./node_modules/@biomejs/biome/configuration_schema.json",
+	"css": {
+		"parser": {
+			// Biome 2.3+ requires opt-in for @apply and other
+			// Tailwind directives.
+			"tailwindDirectives": true
+		}
+	},
+	"$schema": "./node_modules/@biomejs/biome/configuration_schema.json"
 }

buildinfo/buildinfo.go

@@ -87,6 +87,12 @@ func IsDevVersion(v string) bool {
 	return strings.Contains(v, "-"+develPreRelease)
 }
 
+// IsRCVersion returns true if the version has a release candidate
+// pre-release tag, e.g. "v2.31.0-rc.0".
+func IsRCVersion(v string) bool {
+	return strings.Contains(v, "-rc.")
+}
+
 // IsDev returns true if this is a development build.
 // CI builds are also considered development builds.
 func IsDev() bool {

buildinfo/buildinfo_test.go

@@ -102,3 +102,29 @@ func TestBuildInfo(t *testing.T) {
 		}
 	})
 }
+
+func TestIsRCVersion(t *testing.T) {
+	t.Parallel()
+
+	cases := []struct {
+		name     string
+		version  string
+		expected bool
+	}{
+		{"RC0", "v2.31.0-rc.0", true},
+		{"RC1WithBuild", "v2.31.0-rc.1+abc123", true},
+		{"RC10", "v2.31.0-rc.10", true},
+		{"RCDevel", "v2.33.0-rc.1-devel+727ec00f7", true},
+		{"DevelVersion", "v2.31.0-devel+abc123", false},
+		{"StableVersion", "v2.31.0", false},
+		{"DevNoVersion", "v0.0.0-devel+abc123", false},
+		{"BetaVersion", "v2.31.0-beta.1", false},
+	}
+
+	for _, c := range cases {
+		t.Run(c.name, func(t *testing.T) {
+			t.Parallel()
+			require.Equal(t, c.expected, buildinfo.IsRCVersion(c.version))
+		})
+	}
+}

cli/agent.go

@@ -17,6 +17,7 @@ import (
 	"strings"
 	"time"
 
+	"github.com/google/uuid"
 	"github.com/prometheus/client_golang/prometheus"
 	"golang.org/x/xerrors"
 	"gopkg.in/natefinch/lumberjack.v2"
@@ -52,6 +53,8 @@ func workspaceAgent() *serpent.Command {
 		slogJSONPath                   string
 		slogStackdriverPath            string
 		blockFileTransfer              bool
+		blockReversePortForwarding     bool
+		blockLocalPortForwarding       bool
 		agentHeaderCommand             string
 		agentHeader                    []string
 		devcontainers                  bool
@@ -272,11 +275,14 @@ func workspaceAgent() *serpent.Command {
 				logger.Info(ctx, "agent devcontainer detection not enabled")
 			}
 
-			reinitEvents := agentsdk.WaitForReinitLoop(ctx, logger, client)
+			reinitCtx, reinitCancel := context.WithCancel(ctx)
+			defer reinitCancel()
+			reinitEvents := agentsdk.WaitForReinitLoop(reinitCtx, logger, client)
 
 			var (
-				lastErr  error
-				mustExit bool
+				lastOwnerID uuid.UUID
+				lastErr     error
+				mustExit    bool
 			)
 			for {
 				prometheusRegistry := prometheus.NewRegistry()
@@ -315,10 +321,12 @@ func workspaceAgent() *serpent.Command {
 					SSHMaxTimeout:        sshMaxTimeout,
 					Subsystems:           subsystems,
 
-					PrometheusRegistry: prometheusRegistry,
-					BlockFileTransfer:  blockFileTransfer,
-					Execer:             execer,
-					Devcontainers:      devcontainers,
+					PrometheusRegistry:         prometheusRegistry,
+					BlockFileTransfer:          blockFileTransfer,
+					BlockReversePortForwarding: blockReversePortForwarding,
+					BlockLocalPortForwarding:   blockLocalPortForwarding,
+					Execer:                     execer,
+					Devcontainers:              devcontainers,
 					DevcontainerAPIOptions: []agentcontainers.Option{
 						agentcontainers.WithSubAgentURL(agentAuth.agentURL.String()),
 						agentcontainers.WithProjectDiscovery(devcontainerProjectDiscovery),
@@ -343,9 +351,32 @@ func workspaceAgent() *serpent.Command {
 				case <-ctx.Done():
 					logger.Info(ctx, "agent shutting down", slog.Error(context.Cause(ctx)))
 					mustExit = true
-				case event := <-reinitEvents:
-					logger.Info(ctx, "agent received instruction to reinitialize",
-						slog.F("workspace_id", event.WorkspaceID), slog.F("reason", event.Reason))
+				case event, ok := <-reinitEvents:
+					switch {
+					case !ok:
+						// Channel closed — the reinit loop exited
+						// (terminal 409 or context expired). Keep
+						// running the current agent until the parent
+						// context is canceled.
+						logger.Info(ctx, "reinit channel closed, running without reinit capability")
+						reinitEvents = nil
+						<-ctx.Done()
+						mustExit = true
+					case event.OwnerID != uuid.Nil && event.OwnerID == lastOwnerID:
+						// Duplicate reinit for same owner — already
+						// reinitialized. Cancel the reinit loop
+						// goroutine and keep the current agent.
+						logger.Info(ctx, "skipping redundant reinit, owner unchanged",
+							slog.F("owner_id", event.OwnerID))
+						reinitCancel()
+						reinitEvents = nil
+						<-ctx.Done()
+						mustExit = true
+					default:
+						lastOwnerID = event.OwnerID
+						logger.Info(ctx, "agent received instruction to reinitialize",
+							slog.F("workspace_id", event.WorkspaceID), slog.F("reason", event.Reason))
+					}
 				}
 
 				lastErr = agnt.Close()
@@ -466,6 +497,20 @@ func workspaceAgent() *serpent.Command {
 			Description: fmt.Sprintf("Block file transfer using known applications: %s.", strings.Join(agentssh.BlockedFileTransferCommands, ",")),
 			Value:       serpent.BoolOf(&blockFileTransfer),
 		},
+		{
+			Flag:        "block-reverse-port-forwarding",
+			Default:     "false",
+			Env:         "CODER_AGENT_BLOCK_REVERSE_PORT_FORWARDING",
+			Description: "Block reverse port forwarding through the SSH server (ssh -R).",
+			Value:       serpent.BoolOf(&blockReversePortForwarding),
+		},
+		{
+			Flag:        "block-local-port-forwarding",
+			Default:     "false",
+			Env:         "CODER_AGENT_BLOCK_LOCAL_PORT_FORWARDING",
+			Description: "Block local port forwarding through the SSH server (ssh -L).",
+			Value:       serpent.BoolOf(&blockLocalPortForwarding),
+		},
 		{
 			Flag:        "devcontainers-enable",
 			Default:     "true",

cli/clilog/clilog.go

@@ -104,7 +104,7 @@ func (b *Builder) Build(inv *serpent.Invocation) (log slog.Logger, closeLog func
 
 	addSinkIfProvided := func(sinkFn func(io.Writer) slog.Sink, loc string) error {
 		switch loc {
-		case "":
+		case "", "/dev/null":
 		case "/dev/stdout":
 			sinks = append(sinks, sinkFn(inv.Stdout))
 

cli/exp_chat.go

@@ -0,0 +1,194 @@
+package cli
+
+import (
+	"fmt"
+	"os"
+	"path/filepath"
+
+	"github.com/google/uuid"
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/agent/agentcontextconfig"
+	"github.com/coder/coder/v2/codersdk/agentsdk"
+	"github.com/coder/serpent"
+)
+
+func (r *RootCmd) chatCommand() *serpent.Command {
+	return &serpent.Command{
+		Use:   "chat",
+		Short: "Manage agent chats",
+		Long:  "Commands for interacting with chats from within a workspace.",
+		Handler: func(i *serpent.Invocation) error {
+			return i.Command.HelpHandler(i)
+		},
+		Children: []*serpent.Command{
+			r.chatContextCommand(),
+		},
+	}
+}
+
+func (r *RootCmd) chatContextCommand() *serpent.Command {
+	return &serpent.Command{
+		Use:   "context",
+		Short: "Manage chat context",
+		Long:  "Add or clear context files and skills for an active chat session.",
+		Handler: func(i *serpent.Invocation) error {
+			return i.Command.HelpHandler(i)
+		},
+		Children: []*serpent.Command{
+			r.chatContextAddCommand(),
+			r.chatContextClearCommand(),
+		},
+	}
+}
+
+func (*RootCmd) chatContextAddCommand() *serpent.Command {
+	var (
+		dir    string
+		chatID string
+	)
+	agentAuth := &AgentAuth{}
+	cmd := &serpent.Command{
+		Use:   "add",
+		Short: "Add context to an active chat",
+		Long: "Read instruction files and discover skills from a directory, then add " +
+			"them as context to an active chat session. Multiple calls " +
+			"are additive.",
+		Handler: func(inv *serpent.Invocation) error {
+			ctx := inv.Context()
+			ctx, stop := inv.SignalNotifyContext(ctx, StopSignals...)
+			defer stop()
+
+			if dir == "" && inv.Environ.Get("CODER") != "true" {
+				return xerrors.New("this command must be run inside a Coder workspace (set --dir to override)")
+			}
+
+			client, err := agentAuth.CreateClient()
+			if err != nil {
+				return xerrors.Errorf("create agent client: %w", err)
+			}
+
+			resolvedDir := dir
+			if resolvedDir == "" {
+				resolvedDir, err = os.Getwd()
+				if err != nil {
+					return xerrors.Errorf("get working directory: %w", err)
+				}
+			}
+			resolvedDir, err = filepath.Abs(resolvedDir)
+			if err != nil {
+				return xerrors.Errorf("resolve directory: %w", err)
+			}
+			info, err := os.Stat(resolvedDir)
+			if err != nil {
+				return xerrors.Errorf("cannot read directory %q: %w", resolvedDir, err)
+			}
+			if !info.IsDir() {
+				return xerrors.Errorf("%q is not a directory", resolvedDir)
+			}
+
+			parts := agentcontextconfig.ContextPartsFromDir(resolvedDir)
+			if len(parts) == 0 {
+				_, _ = fmt.Fprintln(inv.Stderr, "No context files or skills found in "+resolvedDir)
+				return nil
+			}
+
+			// Resolve chat ID from flag or auto-detect.
+			resolvedChatID, err := parseChatID(chatID)
+			if err != nil {
+				return err
+			}
+
+			resp, err := client.AddChatContext(ctx, agentsdk.AddChatContextRequest{
+				ChatID: resolvedChatID,
+				Parts:  parts,
+			})
+			if err != nil {
+				return xerrors.Errorf("add chat context: %w", err)
+			}
+
+			_, _ = fmt.Fprintf(inv.Stdout, "Added %d context part(s) to chat %s\n", resp.Count, resp.ChatID)
+			return nil
+		},
+		Options: serpent.OptionSet{
+			{
+				Name:        "Directory",
+				Flag:        "dir",
+				Description: "Directory to read context files and skills from. Defaults to the current working directory.",
+				Value:       serpent.StringOf(&dir),
+			},
+			{
+				Name:        "Chat ID",
+				Flag:        "chat",
+				Env:         "CODER_CHAT_ID",
+				Description: "Chat ID to add context to. Auto-detected from CODER_CHAT_ID, the only active chat, or the only top-level active chat.",
+				Value:       serpent.StringOf(&chatID),
+			},
+		},
+	}
+	agentAuth.AttachOptions(cmd, false)
+	return cmd
+}
+
+func (*RootCmd) chatContextClearCommand() *serpent.Command {
+	var chatID string
+	agentAuth := &AgentAuth{}
+	cmd := &serpent.Command{
+		Use:   "clear",
+		Short: "Clear context from an active chat",
+		Long: "Soft-delete all context-file and skill messages from an active chat. " +
+			"The next turn will re-fetch default context from the agent.",
+		Handler: func(inv *serpent.Invocation) error {
+			ctx := inv.Context()
+			ctx, stop := inv.SignalNotifyContext(ctx, StopSignals...)
+			defer stop()
+
+			client, err := agentAuth.CreateClient()
+			if err != nil {
+				return xerrors.Errorf("create agent client: %w", err)
+			}
+
+			resolvedChatID, err := parseChatID(chatID)
+			if err != nil {
+				return err
+			}
+
+			resp, err := client.ClearChatContext(ctx, agentsdk.ClearChatContextRequest{
+				ChatID: resolvedChatID,
+			})
+			if err != nil {
+				return xerrors.Errorf("clear chat context: %w", err)
+			}
+
+			if resp.ChatID == uuid.Nil {
+				_, _ = fmt.Fprintln(inv.Stdout, "No active chats to clear.")
+			} else {
+				_, _ = fmt.Fprintf(inv.Stdout, "Cleared context from chat %s\n", resp.ChatID)
+			}
+			return nil
+		},
+		Options: serpent.OptionSet{{
+			Name:        "Chat ID",
+			Flag:        "chat",
+			Env:         "CODER_CHAT_ID",
+			Description: "Chat ID to clear context from. Auto-detected from CODER_CHAT_ID, the only active chat, or the only top-level active chat.",
+			Value:       serpent.StringOf(&chatID),
+		}},
+	}
+	agentAuth.AttachOptions(cmd, false)
+	return cmd
+}
+
+// parseChatID returns the chat UUID from the flag value (which
+// serpent already populates from --chat or CODER_CHAT_ID). Returns
+// uuid.Nil if empty (the server will auto-detect).
+func parseChatID(flagValue string) (uuid.UUID, error) {
+	if flagValue == "" {
+		return uuid.Nil, nil
+	}
+	parsed, err := uuid.Parse(flagValue)
+	if err != nil {
+		return uuid.Nil, xerrors.Errorf("invalid chat ID %q: %w", flagValue, err)
+	}
+	return parsed, nil
+}

cli/exp_chat_test.go

@@ -0,0 +1,46 @@
+package cli_test
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/cli/clitest"
+)
+
+func TestExpChatContextAdd(t *testing.T) {
+	t.Parallel()
+
+	t.Run("RequiresWorkspaceOrDir", func(t *testing.T) {
+		t.Parallel()
+
+		inv, _ := clitest.New(t, "exp", "chat", "context", "add")
+
+		err := inv.Run()
+		require.Error(t, err)
+		require.Contains(t, err.Error(), "this command must be run inside a Coder workspace")
+	})
+
+	t.Run("AllowsExplicitDir", func(t *testing.T) {
+		t.Parallel()
+
+		inv, _ := clitest.New(t, "exp", "chat", "context", "add", "--dir", t.TempDir())
+
+		err := inv.Run()
+		if err != nil {
+			require.NotContains(t, err.Error(), "this command must be run inside a Coder workspace")
+		}
+	})
+
+	t.Run("AllowsWorkspaceEnv", func(t *testing.T) {
+		t.Parallel()
+
+		inv, _ := clitest.New(t, "exp", "chat", "context", "add")
+		inv.Environ.Set("CODER", "true")
+
+		err := inv.Run()
+		if err != nil {
+			require.NotContains(t, err.Error(), "this command must be run inside a Coder workspace")
+		}
+	})
+}

cli/exp_scaletest.go

@@ -1401,6 +1401,9 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *serpent.Command {
 				// Setup our workspace agent connection.
 				config := workspacetraffic.Config{
 					AgentID:       agent.ID,
+					WorkspaceID:   ws.ID,
+					WorkspaceName: ws.Name,
+					AgentName:     agent.Name,
 					BytesPerTick:  bytesPerTick,
 					Duration:      strategy.timeout,
 					TickInterval:  tickInterval,

cli/root.go

@@ -7,6 +7,7 @@ import (
 	"encoding/base64"
 	"encoding/json"
 	"errors"
+	"flag"
 	"fmt"
 	"io"
 	"net/http"
@@ -148,6 +149,7 @@ func (r *RootCmd) AGPLExperimental() []*serpent.Command {
 	return []*serpent.Command{
 		r.scaletestCmd(),
 		r.errorExample(),
+		r.chatCommand(),
 		r.mcpCommand(),
 		r.promptExample(),
 		r.rptyCommand(),
@@ -710,7 +712,7 @@ func (r *RootCmd) createHTTPClient(ctx context.Context, serverURL *url.URL, inv
 	transport = wrapTransportWithTelemetryHeader(transport, inv)
 	transport = wrapTransportWithUserAgentHeader(transport, inv)
 	if !r.noVersionCheck {
-		transport = wrapTransportWithVersionMismatchCheck(transport, inv, buildinfo.Version(), func(ctx context.Context) (codersdk.BuildInfoResponse, error) {
+		transport = wrapTransportWithVersionCheck(transport, inv, buildinfo.Version(), func(ctx context.Context) (codersdk.BuildInfoResponse, error) {
 			// Create a new client without any wrapped transport
 			// otherwise it creates an infinite loop!
 			basicClient := codersdk.New(serverURL)
@@ -1434,6 +1436,21 @@ func defaultUpgradeMessage(version string) string {
 	return fmt.Sprintf("download the server version with: 'curl -L https://coder.com/install.sh | sh -s -- --version %s'", version)
 }
 
+// serverVersionMessage returns a warning message if the server version
+// is a release candidate or development build. Returns empty string
+// for stable versions. RC is checked before devel because RC dev
+// builds (e.g. v2.33.0-rc.1-devel+hash) contain both tags.
+func serverVersionMessage(serverVersion string) string {
+	switch {
+	case buildinfo.IsRCVersion(serverVersion):
+		return fmt.Sprintf("the server is running a release candidate of Coder (%s)", serverVersion)
+	case buildinfo.IsDevVersion(serverVersion):
+		return fmt.Sprintf("the server is running a development version of Coder (%s)", serverVersion)
+	default:
+		return ""
+	}
+}
+
 // wrapTransportWithEntitlementsCheck adds a middleware to the HTTP transport
 // that checks for entitlement warnings and prints them to the user.
 func wrapTransportWithEntitlementsCheck(rt http.RoundTripper, w io.Writer) http.RoundTripper {
@@ -1452,10 +1469,10 @@ func wrapTransportWithEntitlementsCheck(rt http.RoundTripper, w io.Writer) http.
 	})
 }
 
-// wrapTransportWithVersionMismatchCheck adds a middleware to the HTTP transport
-// that checks for version mismatches between the client and server. If a mismatch
-// is detected, a warning is printed to the user.
-func wrapTransportWithVersionMismatchCheck(rt http.RoundTripper, inv *serpent.Invocation, clientVersion string, getBuildInfo func(ctx context.Context) (codersdk.BuildInfoResponse, error)) http.RoundTripper {
+// wrapTransportWithVersionCheck adds a middleware to the HTTP transport
+// that checks the server version and warns about development builds,
+// release candidates, and client/server version mismatches.
+func wrapTransportWithVersionCheck(rt http.RoundTripper, inv *serpent.Invocation, clientVersion string, getBuildInfo func(ctx context.Context) (codersdk.BuildInfoResponse, error)) http.RoundTripper {
 	var once sync.Once
 	return roundTripper(func(req *http.Request) (*http.Response, error) {
 		res, err := rt.RoundTrip(req)
@@ -1467,9 +1484,16 @@ func wrapTransportWithVersionMismatchCheck(rt http.RoundTripper, inv *serpent.In
 			if serverVersion == "" {
 				return
 			}
+			// Warn about non-stable server versions. Skip
+			// during tests to avoid polluting golden files.
+			if msg := serverVersionMessage(serverVersion); msg != "" && flag.Lookup("test.v") == nil {
+				warning := pretty.Sprint(cliui.DefaultStyles.Warn, msg)
+				_, _ = fmt.Fprintln(inv.Stderr, warning)
+			}
 			if buildinfo.VersionsMatch(clientVersion, serverVersion) {
 				return
 			}
+
 			upgradeMessage := defaultUpgradeMessage(semver.Canonical(serverVersion))
 			if serverInfo, err := getBuildInfo(inv.Context()); err == nil {
 				switch {

cli/root_internal_test.go

@@ -91,7 +91,7 @@ func Test_formatExamples(t *testing.T) {
 	}
 }
 
-func Test_wrapTransportWithVersionMismatchCheck(t *testing.T) {
+func Test_wrapTransportWithVersionCheck(t *testing.T) {
 	t.Parallel()
 
 	t.Run("NoOutput", func(t *testing.T) {
@@ -102,7 +102,7 @@ func Test_wrapTransportWithVersionMismatchCheck(t *testing.T) {
 		var buf bytes.Buffer
 		inv := cmd.Invoke()
 		inv.Stderr = &buf
-		rt := wrapTransportWithVersionMismatchCheck(roundTripper(func(req *http.Request) (*http.Response, error) {
+		rt := wrapTransportWithVersionCheck(roundTripper(func(req *http.Request) (*http.Response, error) {
 			return &http.Response{
 				StatusCode: http.StatusOK,
 				Header: http.Header{
@@ -131,7 +131,7 @@ func Test_wrapTransportWithVersionMismatchCheck(t *testing.T) {
 		inv := cmd.Invoke()
 		inv.Stderr = &buf
 		expectedUpgradeMessage := "My custom upgrade message"
-		rt := wrapTransportWithVersionMismatchCheck(roundTripper(func(req *http.Request) (*http.Response, error) {
+		rt := wrapTransportWithVersionCheck(roundTripper(func(req *http.Request) (*http.Response, error) {
 			return &http.Response{
 				StatusCode: http.StatusOK,
 				Header: http.Header{
@@ -159,6 +159,53 @@ func Test_wrapTransportWithVersionMismatchCheck(t *testing.T) {
 		expectedOutput := fmt.Sprintln(pretty.Sprint(cliui.DefaultStyles.Warn, fmtOutput))
 		require.Equal(t, expectedOutput, buf.String())
 	})
+
+	t.Run("ServerStableVersion", func(t *testing.T) {
+		t.Parallel()
+		r := &RootCmd{}
+		cmd, err := r.Command(nil)
+		require.NoError(t, err)
+		var buf bytes.Buffer
+		inv := cmd.Invoke()
+		inv.Stderr = &buf
+		rt := wrapTransportWithVersionCheck(roundTripper(func(req *http.Request) (*http.Response, error) {
+			return &http.Response{
+				StatusCode: http.StatusOK,
+				Header: http.Header{
+					codersdk.BuildVersionHeader: []string{"v2.31.0"},
+				},
+				Body: io.NopCloser(nil),
+			}, nil
+		}), inv, "v2.31.0", nil)
+		req := httptest.NewRequest(http.MethodGet, "http://example.com", nil)
+		res, err := rt.RoundTrip(req)
+		require.NoError(t, err)
+		defer res.Body.Close()
+		require.Empty(t, buf.String())
+	})
+}
+
+func Test_serverVersionMessage(t *testing.T) {
+	t.Parallel()
+
+	cases := []struct {
+		name     string
+		version  string
+		expected string
+	}{
+		{"Stable", "v2.31.0", ""},
+		{"Dev", "v0.0.0-devel+abc123", "the server is running a development version of Coder (v0.0.0-devel+abc123)"},
+		{"RC", "v2.31.0-rc.1", "the server is running a release candidate of Coder (v2.31.0-rc.1)"},
+		{"RCDevel", "v2.33.0-rc.1-devel+727ec00f7", "the server is running a release candidate of Coder (v2.33.0-rc.1-devel+727ec00f7)"},
+		{"Empty", "", ""},
+	}
+
+	for _, c := range cases {
+		t.Run(c.name, func(t *testing.T) {
+			t.Parallel()
+			require.Equal(t, c.expected, serverVersionMessage(c.version))
+		})
+	}
 }
 
 func Test_wrapTransportWithTelemetryHeader(t *testing.T) {

cli/ssh.go

@@ -52,6 +52,10 @@ import (
 
 const (
 	disableUsageApp = "disable"
+
+	// Retry transient errors during SSH connection establishment.
+	sshRetryInterval = 2 * time.Second
+	sshMaxAttempts   = 10 // initial + retries per step
 )
 
 var (
@@ -62,6 +66,53 @@ var (
 	workspaceNameRe         = regexp.MustCompile(`[/.]+|--`)
 )
 
+// isRetryableError checks for transient connection errors worth
+// retrying: DNS failures, connection refused, and server 5xx.
+func isRetryableError(err error) bool {
+	if err == nil || xerrors.Is(err, context.Canceled) {
+		return false
+	}
+	// Check connection errors before context.DeadlineExceeded because
+	// net.Dialer.Timeout produces *net.OpError that matches both.
+	if codersdk.IsConnectionError(err) {
+		return true
+	}
+	if xerrors.Is(err, context.DeadlineExceeded) {
+		return false
+	}
+	var sdkErr *codersdk.Error
+	if xerrors.As(err, &sdkErr) {
+		return sdkErr.StatusCode() >= 500
+	}
+	return false
+}
+
+// retryWithInterval calls fn up to maxAttempts times, waiting
+// interval between attempts. Stops on success, non-retryable
+// error, or context cancellation.
+func retryWithInterval(ctx context.Context, logger slog.Logger, interval time.Duration, maxAttempts int, fn func() error) error {
+	var lastErr error
+	attempt := 0
+	for r := retry.New(interval, interval); r.Wait(ctx); {
+		lastErr = fn()
+		if lastErr == nil || !isRetryableError(lastErr) {
+			return lastErr
+		}
+		attempt++
+		if attempt >= maxAttempts {
+			break
+		}
+		logger.Warn(ctx, "transient error, retrying",
+			slog.Error(lastErr),
+			slog.F("attempt", attempt),
+		)
+	}
+	if lastErr != nil {
+		return lastErr
+	}
+	return ctx.Err()
+}
+
 func (r *RootCmd) ssh() *serpent.Command {
 	var (
 		stdio               bool
@@ -277,10 +328,17 @@ func (r *RootCmd) ssh() *serpent.Command {
 				HostnameSuffix: hostnameSuffix,
 			}
 
-			workspace, workspaceAgent, err := findWorkspaceAndAgentByHostname(
-				ctx, inv, client,
-				inv.Args[0], cliConfig, disableAutostart)
-			if err != nil {
+			// Populated by the closure below.
+			var workspace codersdk.Workspace
+			var workspaceAgent codersdk.WorkspaceAgent
+			resolveWorkspace := func() error {
+				var err error
+				workspace, workspaceAgent, err = findWorkspaceAndAgentByHostname(
+					ctx, inv, client,
+					inv.Args[0], cliConfig, disableAutostart)
+				return err
+			}
+			if err := retryWithInterval(ctx, logger, sshRetryInterval, sshMaxAttempts, resolveWorkspace); err != nil {
 				return err
 			}
 
@@ -306,8 +364,13 @@ func (r *RootCmd) ssh() *serpent.Command {
 				wait = false
 			}
 
-			templateVersion, err := client.TemplateVersion(ctx, workspace.LatestBuild.TemplateVersionID)
-			if err != nil {
+			var templateVersion codersdk.TemplateVersion
+			fetchVersion := func() error {
+				var err error
+				templateVersion, err = client.TemplateVersion(ctx, workspace.LatestBuild.TemplateVersionID)
+				return err
+			}
+			if err := retryWithInterval(ctx, logger, sshRetryInterval, sshMaxAttempts, fetchVersion); err != nil {
 				return err
 			}
 
@@ -347,8 +410,12 @@ func (r *RootCmd) ssh() *serpent.Command {
 			// If we're in stdio mode, check to see if we can use Coder Connect.
 			// We don't support Coder Connect over non-stdio coder ssh yet.
 			if stdio && !forceNewTunnel {
-				connInfo, err := wsClient.AgentConnectionInfoGeneric(ctx)
-				if err != nil {
+				var connInfo workspacesdk.AgentConnectionInfo
+				if err := retryWithInterval(ctx, logger, sshRetryInterval, sshMaxAttempts, func() error {
+					var err error
+					connInfo, err = wsClient.AgentConnectionInfoGeneric(ctx)
+					return err
+				}); err != nil {
 					return xerrors.Errorf("get agent connection info: %w", err)
 				}
 				coderConnectHost := fmt.Sprintf("%s.%s.%s.%s",
@@ -384,23 +451,27 @@ func (r *RootCmd) ssh() *serpent.Command {
 						})
 						defer closeUsage()
 					}
-					return runCoderConnectStdio(ctx, fmt.Sprintf("%s:22", coderConnectHost), stdioReader, stdioWriter, stack)
+					return runCoderConnectStdio(ctx, fmt.Sprintf("%s:22", coderConnectHost), stdioReader, stdioWriter, stack, logger)
 				}
 			}
 
 			if r.disableDirect {
 				_, _ = fmt.Fprintln(inv.Stderr, "Direct connections disabled.")
 			}
-			conn, err := wsClient.
-				DialAgent(ctx, workspaceAgent.ID, &workspacesdk.DialAgentOptions{
+			var conn workspacesdk.AgentConn
+			if err := retryWithInterval(ctx, logger, sshRetryInterval, sshMaxAttempts, func() error {
+				var err error
+				conn, err = wsClient.DialAgent(ctx, workspaceAgent.ID, &workspacesdk.DialAgentOptions{
 					Logger:          logger,
 					BlockEndpoints:  r.disableDirect,
 					EnableTelemetry: !r.disableNetworkTelemetry,
 				})
-			if err != nil {
+				return err
+			}); err != nil {
 				return xerrors.Errorf("dial agent: %w", err)
 			}
 			if err = stack.push("agent conn", conn); err != nil {
+				_ = conn.Close()
 				return err
 			}
 			conn.AwaitReachable(ctx)
@@ -1578,16 +1649,27 @@ func WithTestOnlyCoderConnectDialer(ctx context.Context, dialer coderConnectDial
 func testOrDefaultDialer(ctx context.Context) coderConnectDialer {
 	dialer, ok := ctx.Value(coderConnectDialerContextKey{}).(coderConnectDialer)
 	if !ok || dialer == nil {
-		return &net.Dialer{}
+		// Timeout prevents hanging on broken tunnels (OS default is very long).
+		return &net.Dialer{
+			Timeout:   5 * time.Second,
+			KeepAlive: 30 * time.Second,
+		}
 	}
 	return dialer
 }
 
-func runCoderConnectStdio(ctx context.Context, addr string, stdin io.Reader, stdout io.Writer, stack *closerStack) error {
+func runCoderConnectStdio(ctx context.Context, addr string, stdin io.Reader, stdout io.Writer, stack *closerStack, logger slog.Logger) error {
 	dialer := testOrDefaultDialer(ctx)
-	conn, err := dialer.DialContext(ctx, "tcp", addr)
-	if err != nil {
-		return xerrors.Errorf("dial coder connect host: %w", err)
+	var conn net.Conn
+	if err := retryWithInterval(ctx, logger, sshRetryInterval, sshMaxAttempts, func() error {
+		var err error
+		conn, err = dialer.DialContext(ctx, "tcp", addr)
+		if err != nil {
+			return xerrors.Errorf("dial coder connect host %q over tcp: %w", addr, err)
+		}
+		return nil
+	}); err != nil {
+		return err
 	}
 	if err := stack.push("tcp conn", conn); err != nil {
 		return err

cli/ssh_internal_test.go

@@ -5,7 +5,9 @@ import (
 	"fmt"
 	"io"
 	"net"
+	"net/http"
 	"net/url"
+	"os"
 	"sync"
 	"testing"
 	"time"
@@ -226,6 +228,41 @@ func TestCloserStack_Timeout(t *testing.T) {
 	testutil.TryReceive(ctx, t, closed)
 }
 
+func TestCloserStack_PushAfterClose_ConnClosed(t *testing.T) {
+	t.Parallel()
+	ctx := testutil.Context(t, testutil.WaitShort)
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true}).Leveled(slog.LevelDebug)
+	uut := newCloserStack(ctx, logger, quartz.NewMock(t))
+
+	uut.close(xerrors.New("canceled"))
+
+	closes := new([]*fakeCloser)
+	fc := &fakeCloser{closes: closes}
+	err := uut.push("conn", fc)
+	require.Error(t, err)
+	require.Equal(t, []*fakeCloser{fc}, *closes, "should close conn on failed push")
+}
+
+func TestCoderConnectDialer_DefaultTimeout(t *testing.T) {
+	t.Parallel()
+	ctx := context.Background()
+
+	dialer := testOrDefaultDialer(ctx)
+	d, ok := dialer.(*net.Dialer)
+	require.True(t, ok, "expected *net.Dialer")
+	assert.Equal(t, 5*time.Second, d.Timeout)
+	assert.Equal(t, 30*time.Second, d.KeepAlive)
+}
+
+func TestCoderConnectDialer_Overridden(t *testing.T) {
+	t.Parallel()
+	custom := &net.Dialer{Timeout: 99 * time.Second}
+	ctx := WithTestOnlyCoderConnectDialer(context.Background(), custom)
+
+	dialer := testOrDefaultDialer(ctx)
+	assert.Equal(t, custom, dialer)
+}
+
 func TestCoderConnectStdio(t *testing.T) {
 	t.Parallel()
 
@@ -254,7 +291,7 @@ func TestCoderConnectStdio(t *testing.T) {
 
 	stdioDone := make(chan struct{})
 	go func() {
-		err = runCoderConnectStdio(ctx, ln.Addr().String(), clientOutput, serverInput, stack)
+		err = runCoderConnectStdio(ctx, ln.Addr().String(), clientOutput, serverInput, stack, logger)
 		assert.NoError(t, err)
 		close(stdioDone)
 	}()
@@ -448,3 +485,131 @@ func Test_getWorkspaceAgent(t *testing.T) {
 		assert.Contains(t, err.Error(), "available agents: [clark krypton zod]")
 	})
 }
+
+func TestIsRetryableError(t *testing.T) {
+	t.Parallel()
+
+	tests := []struct {
+		name      string
+		err       error
+		retryable bool
+	}{
+		{"Nil", nil, false},
+		{"ContextCanceled", context.Canceled, false},
+		{"ContextDeadlineExceeded", context.DeadlineExceeded, false},
+		{"WrappedContextCanceled", xerrors.Errorf("wrapped: %w", context.Canceled), false},
+		{"DNSError", &net.DNSError{Err: "no such host", Name: "example.com", IsNotFound: true}, true},
+		{"OpError", &net.OpError{Op: "dial", Net: "tcp", Err: &os.SyscallError{}}, true},
+		{"WrappedDNSError", xerrors.Errorf("connect: %w", &net.DNSError{Err: "no such host", Name: "example.com"}), true},
+		{"SDKError_500", codersdk.NewTestError(http.StatusInternalServerError, "GET", "/api"), true},
+		{"SDKError_502", codersdk.NewTestError(http.StatusBadGateway, "GET", "/api"), true},
+		{"SDKError_503", codersdk.NewTestError(http.StatusServiceUnavailable, "GET", "/api"), true},
+		{"SDKError_401", codersdk.NewTestError(http.StatusUnauthorized, "GET", "/api"), false},
+		{"SDKError_403", codersdk.NewTestError(http.StatusForbidden, "GET", "/api"), false},
+		{"SDKError_404", codersdk.NewTestError(http.StatusNotFound, "GET", "/api"), false},
+		{"GenericError", xerrors.New("something went wrong"), false},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			t.Parallel()
+			assert.Equal(t, tt.retryable, isRetryableError(tt.err))
+		})
+	}
+
+	// net.Dialer.Timeout produces *net.OpError that matches both
+	// IsConnectionError and context.DeadlineExceeded. Verify it is retryable.
+	t.Run("DialTimeout", func(t *testing.T) {
+		t.Parallel()
+		ctx, cancel := context.WithDeadline(context.Background(), time.Now())
+		defer cancel()
+		<-ctx.Done() // ensure deadline has fired
+		_, err := (&net.Dialer{}).DialContext(ctx, "tcp", "127.0.0.1:1")
+		require.Error(t, err)
+		// Proves the ambiguity: this error matches BOTH checks.
+		require.ErrorIs(t, err, context.DeadlineExceeded)
+		require.ErrorAs(t, err, new(*net.OpError))
+		assert.True(t, isRetryableError(err))
+		// Also when wrapped, as runCoderConnectStdio does.
+		assert.True(t, isRetryableError(xerrors.Errorf("dial coder connect: %w", err)))
+	})
+}
+
+func TestRetryWithInterval(t *testing.T) {
+	t.Parallel()
+
+	const interval = time.Millisecond
+	const maxAttempts = 3
+
+	dnsErr := &net.DNSError{Err: "no such host", Name: "example.com", IsNotFound: true}
+	logger := slogtest.Make(t, nil).Leveled(slog.LevelDebug)
+
+	t.Run("Succeeds_FirstTry", func(t *testing.T) {
+		t.Parallel()
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		attempts := 0
+		err := retryWithInterval(ctx, logger, interval, maxAttempts, func() error {
+			attempts++
+			return nil
+		})
+		require.NoError(t, err)
+		assert.Equal(t, 1, attempts)
+	})
+
+	t.Run("Succeeds_AfterTransientFailures", func(t *testing.T) {
+		t.Parallel()
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		attempts := 0
+		err := retryWithInterval(ctx, logger, interval, maxAttempts, func() error {
+			attempts++
+			if attempts < 3 {
+				return dnsErr
+			}
+			return nil
+		})
+		require.NoError(t, err)
+		assert.Equal(t, 3, attempts)
+	})
+
+	t.Run("Stops_NonRetryableError", func(t *testing.T) {
+		t.Parallel()
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		attempts := 0
+		err := retryWithInterval(ctx, logger, interval, maxAttempts, func() error {
+			attempts++
+			return xerrors.New("permanent failure")
+		})
+		require.ErrorContains(t, err, "permanent failure")
+		assert.Equal(t, 1, attempts)
+	})
+
+	t.Run("Stops_MaxAttemptsExhausted", func(t *testing.T) {
+		t.Parallel()
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		attempts := 0
+		err := retryWithInterval(ctx, logger, interval, maxAttempts, func() error {
+			attempts++
+			return dnsErr
+		})
+		require.Error(t, err)
+		assert.Equal(t, maxAttempts, attempts)
+	})
+
+	t.Run("Stops_ContextCanceled", func(t *testing.T) {
+		t.Parallel()
+		ctx, cancel := context.WithCancel(context.Background())
+
+		attempts := 0
+		err := retryWithInterval(ctx, logger, interval, maxAttempts, func() error {
+			attempts++
+			cancel()
+			return dnsErr
+		})
+		require.Error(t, err)
+		assert.Equal(t, 1, attempts)
+	})
+}

cli/sync_test.go

@@ -165,6 +165,37 @@ func TestSyncCommands_Golden(t *testing.T) {
 		clitest.TestGoldenFile(t, "TestSyncCommands_Golden/want_success", outBuf.Bytes(), nil)
 	})
 
+	t.Run("want_multiple_deps", func(t *testing.T) {
+		t.Parallel()
+		path, cleanup := setupSocketServer(t)
+		defer cleanup()
+
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		var outBuf bytes.Buffer
+		inv, _ := clitest.New(t, "exp", "sync", "want", "test-unit", "dep-1", "dep-2", "dep-3", "--socket-path", path)
+		inv.Stdout = &outBuf
+		inv.Stderr = &outBuf
+
+		err := inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		// Verify all dependencies were registered by checking status.
+		outBuf.Reset()
+		inv, _ = clitest.New(t, "exp", "sync", "status", "test-unit", "--socket-path", path, "--output", "json")
+		inv.Stdout = &outBuf
+		inv.Stderr = &outBuf
+
+		err = inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		// The output should mention all three dependencies.
+		output := outBuf.String()
+		require.Contains(t, output, "dep-1")
+		require.Contains(t, output, "dep-2")
+		require.Contains(t, output, "dep-3")
+	})
+
 	t.Run("complete", func(t *testing.T) {
 		t.Parallel()
 		path, cleanup := setupSocketServer(t)

cli/sync_want.go

@@ -11,17 +11,16 @@ import (
 
 func (*RootCmd) syncWant(socketPath *string) *serpent.Command {
 	cmd := &serpent.Command{
-		Use:   "want <unit> <depends-on>",
-		Short: "Declare that a unit depends on another unit completing before it can start",
-		Long:  "Declare that a unit depends on another unit completing before it can start. The unit specified first will not start until the second has signaled that it has completed.",
+		Use:   "want <unit> <depends-on> [depends-on...]",
+		Short: "Declare that a unit depends on other units completing before it can start",
+		Long:  "Declare that a unit depends on one or more other units completing before it can start. The unit specified first will not start until all subsequent units have signaled that they have completed.",
 		Handler: func(i *serpent.Invocation) error {
 			ctx := i.Context()
 
-			if len(i.Args) != 2 {
-				return xerrors.New("exactly two arguments are required: unit and depends-on")
+			if len(i.Args) < 2 {
+				return xerrors.New("at least two arguments are required: unit and one or more depends-on")
 			}
 			dependentUnit := unit.ID(i.Args[0])
-			dependsOn := unit.ID(i.Args[1])
 
 			opts := []agentsocket.Option{}
 			if *socketPath != "" {
@@ -34,8 +33,10 @@ func (*RootCmd) syncWant(socketPath *string) *serpent.Command {
 			}
 			defer client.Close()
 
-			if err := client.SyncWant(ctx, dependentUnit, dependsOn); err != nil {
-				return xerrors.Errorf("declare dependency failed: %w", err)
+			for _, dep := range i.Args[1:] {
+				if err := client.SyncWant(ctx, dependentUnit, unit.ID(dep)); err != nil {
+					return xerrors.Errorf("declare dependency failed: %w", err)
+				}
 			}
 
 			cliui.Info(i.Stdout, "Success")

cli/testdata/coder_agent_--help.golden

@@ -39,6 +39,12 @@ OPTIONS:
       --block-file-transfer bool, $CODER_AGENT_BLOCK_FILE_TRANSFER (default: false)
           Block file transfer using known applications: nc,rsync,scp,sftp.
 
+      --block-local-port-forwarding bool, $CODER_AGENT_BLOCK_LOCAL_PORT_FORWARDING (default: false)
+          Block local port forwarding through the SSH server (ssh -L).
+
+      --block-reverse-port-forwarding bool, $CODER_AGENT_BLOCK_REVERSE_PORT_FORWARDING (default: false)
+          Block reverse port forwarding through the SSH server (ssh -R).
+
       --boundary-log-proxy-socket-path string, $CODER_AGENT_BOUNDARY_LOG_PROXY_SOCKET_PATH (default: /tmp/boundary-audit.sock)
           The path for the boundary log proxy server Unix socket. Boundary
           should write audit logs to this socket.

cli/testdata/coder_exp_sync_--help.golden

@@ -16,7 +16,7 @@ SUBCOMMANDS:
     ping        Test agent socket connectivity and health
     start       Wait until all unit dependencies are satisfied
     status      Show unit status and dependency state
-    want        Declare that a unit depends on another unit completing before it
+    want        Declare that a unit depends on other units completing before it
                 can start
 
 OPTIONS:

cli/testdata/coder_exp_sync_want_--help.golden

@@ -1,13 +1,13 @@
 coder v0.0.0-devel
 
 USAGE:
-  coder exp sync want <unit> <depends-on>
+  coder exp sync want <unit> <depends-on> [depends-on...]
 
-  Declare that a unit depends on another unit completing before it can start
+  Declare that a unit depends on other units completing before it can start
 
-  Declare that a unit depends on another unit completing before it can start.
-  The unit specified first will not start until the second has signaled that it
-  has completed.
+  Declare that a unit depends on one or more other units completing before it
+  can start. The unit specified first will not start until all subsequent units
+  have signaled that they have completed.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_provisioner_jobs_list_--help.golden

@@ -11,7 +11,7 @@ OPTIONS:
   -O, --org string, $CODER_ORGANIZATION
           Select which organization (uuid or name) to use.
 
-  -c, --column [id|created at|started at|completed at|canceled at|error|error code|status|worker id|worker name|file id|tags|queue position|queue size|organization id|initiator id|template version id|workspace build id|type|available workers|template version name|template id|template name|template display name|template icon|workspace id|workspace name|logs overflowed|organization|queue] (default: created at,id,type,template display name,status,queue,tags)
+  -c, --column [id|created at|started at|completed at|canceled at|error|error code|status|worker id|worker name|file id|tags|queue position|queue size|organization id|initiator id|template version id|workspace build id|type|available workers|template version name|template id|template name|template display name|template icon|workspace id|workspace name|workspace build transition|logs overflowed|organization|queue] (default: created at,id,type,template display name,status,queue,tags)
           Columns to display in table output.
 
   -i, --initiator string, $CODER_PROVISIONER_JOB_LIST_INITIATOR

cli/testdata/coder_provisioner_jobs_list_--output_json.golden

@@ -58,7 +58,8 @@
       "template_display_name": "",
       "template_icon": "",
       "workspace_id": "===========[workspace ID]===========",
-      "workspace_name": "test-workspace"
+      "workspace_name": "test-workspace",
+      "workspace_build_transition": "start"
     },
     "logs_overflowed": false,
     "organization_name": "Coder"

cli/testdata/coder_server_--help.golden

@@ -211,6 +211,13 @@ AI BRIDGE PROXY OPTIONS:
           certificates not trusted by the system. If not provided, the system
           certificate pool is used.
 
+CHAT OPTIONS: 
+Configure the background chat processing daemon.
+
+      --chat-debug-logging-enabled bool, $CODER_CHAT_DEBUG_LOGGING_ENABLED (default: false)
+          Force chat debug logging on for every chat, bypassing the runtime
+          admin and user opt-in settings.
+
 CLIENT OPTIONS: 
 These options change the behavior of how clients interact with the Coder.
 Clients include the Coder CLI, Coder Desktop, IDE extensions, and the web UI.

cli/testdata/server-config.yaml.golden

@@ -757,6 +757,10 @@ chat:
   # How many pending chats a worker should acquire per polling cycle.
   # (default: 10, type: int)
   acquireBatchSize: 10
+  # Force chat debug logging on for every chat, bypassing the runtime admin and user
+  # opt-in settings.
+  # (default: false, type: bool)
+  debugLoggingEnabled: false
 aibridge:
   # Whether to start an in-memory aibridged instance.
   # (default: false, type: bool)

cli/usercreate_test.go

@@ -134,6 +134,7 @@ func TestUserCreate(t *testing.T) {
 		{
 			name: "ServiceAccount",
 			args: []string{"--service-account", "-u", "dean"},
+			err:  "Premium feature",
 		},
 		{
 			name: "ServiceAccountLoginType",

coderd/agentapi/connectionlog.go

@@ -85,7 +85,7 @@ func (a *ConnLogAPI) ReportConnection(ctx context.Context, req *agentproto.Repor
 		AgentName:        a.AgentName,
 		Type:             connectionType,
 		Code:             code,
-		Ip:               logIP,
+		IP:               logIP,
 		ConnectionID: uuid.NullUUID{
 			UUID:  connectionID,
 			Valid: true,

coderd/agentapi/connectionlog_test.go

@@ -152,7 +152,7 @@ func TestConnectionLog(t *testing.T) {
 					Int32: tt.status,
 					Valid: *tt.action == agentproto.Connection_DISCONNECT,
 				},
-				Ip:   expectedIP,
+				IP:   expectedIP,
 				Type: agentProtoConnectionTypeToConnectionLog(t, *tt.typ),
 				DisconnectReason: sql.NullString{
 					String: tt.reason,

coderd/agentapi/logs.go

@@ -77,8 +77,9 @@ func (a *LogsAPI) BatchCreateLogs(ctx context.Context, req *agentproto.BatchCrea
 	level := make([]database.LogLevel, 0)
 	outputLength := 0
 	for _, logEntry := range req.Logs {
-		output = append(output, logEntry.Output)
-		outputLength += len(logEntry.Output)
+		sanitizedOutput := agentsdk.SanitizeLogOutput(logEntry.Output)
+		output = append(output, sanitizedOutput)
+		outputLength += len(sanitizedOutput)
 
 		var dbLevel database.LogLevel
 		switch logEntry.Level {

coderd/agentapi/logs_test.go

@@ -139,6 +139,59 @@ func TestBatchCreateLogs(t *testing.T) {
 		require.True(t, publishWorkspaceAgentLogsUpdateCalled)
 	})
 
+	t.Run("SanitizesOutput", func(t *testing.T) {
+		t.Parallel()
+
+		dbM := dbmock.NewMockStore(gomock.NewController(t))
+		now := dbtime.Now()
+		api := &agentapi.LogsAPI{
+			AgentFn: func(context.Context) (database.WorkspaceAgent, error) {
+				return agent, nil
+			},
+			Database: dbM,
+			Log:      testutil.Logger(t),
+			TimeNowFn: func() time.Time {
+				return now
+			},
+		}
+
+		rawOutput := "before\x00middle\xc3\x28after"
+		sanitizedOutput := agentsdk.SanitizeLogOutput(rawOutput)
+		expectedOutputLength := int32(len(sanitizedOutput)) //nolint:gosec // Test-controlled string length is small.
+		req := &agentproto.BatchCreateLogsRequest{
+			LogSourceId: logSource.ID[:],
+			Logs: []*agentproto.Log{
+				{
+					CreatedAt: timestamppb.New(now),
+					Level:     agentproto.Log_WARN,
+					Output:    rawOutput,
+				},
+			},
+		}
+
+		dbM.EXPECT().InsertWorkspaceAgentLogs(gomock.Any(), database.InsertWorkspaceAgentLogsParams{
+			AgentID:      agent.ID,
+			LogSourceID:  logSource.ID,
+			CreatedAt:    now,
+			Output:       []string{sanitizedOutput},
+			Level:        []database.LogLevel{database.LogLevelWarn},
+			OutputLength: expectedOutputLength,
+		}).Return([]database.WorkspaceAgentLog{
+			{
+				AgentID:     agent.ID,
+				CreatedAt:   now,
+				ID:          1,
+				Output:      sanitizedOutput,
+				Level:       database.LogLevelWarn,
+				LogSourceID: logSource.ID,
+			},
+		}, nil)
+
+		resp, err := api.BatchCreateLogs(context.Background(), req)
+		require.NoError(t, err)
+		require.Equal(t, &agentproto.BatchCreateLogsResponse{}, resp)
+	})
+
 	t.Run("NoWorkspacePublishIfNotFirstLogs", func(t *testing.T) {
 		t.Parallel()
 

coderd/agentapi/subagent.go

@@ -71,7 +71,7 @@ func (a *SubAgentAPI) CreateSubAgent(ctx context.Context, req *agentproto.Create
 	// An ID is only given in the request when it is a terraform-defined devcontainer
 	// that has attached resources. These subagents are pre-provisioned by terraform
 	// (the agent record already exists), so we update configurable fields like
-	// display_apps rather than creating a new agent.
+	// display_apps and directory rather than creating a new agent.
 	if req.Id != nil {
 		id, err := uuid.FromBytes(req.Id)
 		if err != nil {
@@ -97,6 +97,16 @@ func (a *SubAgentAPI) CreateSubAgent(ctx context.Context, req *agentproto.Create
 			return nil, xerrors.Errorf("update workspace agent display apps: %w", err)
 		}
 
+		if req.Directory != "" {
+			if err := a.Database.UpdateWorkspaceAgentDirectoryByID(ctx, database.UpdateWorkspaceAgentDirectoryByIDParams{
+				ID:        id,
+				Directory: req.Directory,
+				UpdatedAt: createdAt,
+			}); err != nil {
+				return nil, xerrors.Errorf("update workspace agent directory: %w", err)
+			}
+		}
+
 		return &agentproto.CreateSubAgentResponse{
 			Agent: &agentproto.SubAgent{
 				Name:      subAgent.Name,

coderd/agentapi/subagent_test.go

@@ -1267,11 +1267,11 @@ func TestSubAgentAPI(t *testing.T) {
 					agentID, err := uuid.FromBytes(resp.Agent.Id)
 					require.NoError(t, err)
 
-					// And: The database agent's other fields are unchanged.
+					// And: The database agent's name, architecture, and OS are unchanged.
 					updatedAgent, err := db.GetWorkspaceAgentByID(dbauthz.AsSystemRestricted(ctx), agentID)
 					require.NoError(t, err)
 					require.Equal(t, baseChildAgent.Name, updatedAgent.Name)
-					require.Equal(t, baseChildAgent.Directory, updatedAgent.Directory)
+					require.Equal(t, "/different/path", updatedAgent.Directory)
 					require.Equal(t, baseChildAgent.Architecture, updatedAgent.Architecture)
 					require.Equal(t, baseChildAgent.OperatingSystem, updatedAgent.OperatingSystem)
 
@@ -1280,6 +1280,42 @@ func TestSubAgentAPI(t *testing.T) {
 					require.Equal(t, database.DisplayAppWebTerminal, updatedAgent.DisplayApps[0])
 				},
 			},
+			{
+				name: "OK_DirectoryUpdated",
+				setup: func(t *testing.T, db database.Store, agent database.WorkspaceAgent) *proto.CreateSubAgentRequest {
+					// Given: An existing child agent with a stale host-side
+					// directory (as set by the provisioner at build time).
+					childAgent := dbgen.WorkspaceAgent(t, db, database.WorkspaceAgent{
+						ParentID:        uuid.NullUUID{Valid: true, UUID: agent.ID},
+						ResourceID:      agent.ResourceID,
+						Name:            baseChildAgent.Name,
+						Directory:       "/home/coder/project",
+						Architecture:    baseChildAgent.Architecture,
+						OperatingSystem: baseChildAgent.OperatingSystem,
+						DisplayApps:     baseChildAgent.DisplayApps,
+					})
+
+					// When: Agent injection sends the correct
+					// container-internal path.
+					return &proto.CreateSubAgentRequest{
+						Id:        childAgent.ID[:],
+						Directory: "/workspaces/project",
+						DisplayApps: []proto.CreateSubAgentRequest_DisplayApp{
+							proto.CreateSubAgentRequest_WEB_TERMINAL,
+						},
+					}
+				},
+				check: func(t *testing.T, ctx context.Context, db database.Store, resp *proto.CreateSubAgentResponse, agent database.WorkspaceAgent) {
+					agentID, err := uuid.FromBytes(resp.Agent.Id)
+					require.NoError(t, err)
+
+					// Then: Directory is updated to the container-internal
+					// path.
+					updatedAgent, err := db.GetWorkspaceAgentByID(dbauthz.AsSystemRestricted(ctx), agentID)
+					require.NoError(t, err)
+					require.Equal(t, "/workspaces/project", updatedAgent.Directory)
+				},
+			},
 			{
 				name: "Error/MalformedID",
 				setup: func(t *testing.T, db database.Store, agent database.WorkspaceAgent) *proto.CreateSubAgentRequest {

coderd/apidoc/docs.go

@@ -1266,6 +1266,68 @@ const docTemplate = `{
                 ]
             }
         },
+        "/experimental/chats/config/retention-days": {
+            "get": {
+                "produces": [
+                    "application/json"
+                ],
+                "tags": [
+                    "Chats"
+                ],
+                "summary": "Get chat retention days",
+                "operationId": "get-chat-retention-days",
+                "responses": {
+                    "200": {
+                        "description": "OK",
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.ChatRetentionDaysResponse"
+                        }
+                    }
+                },
+                "security": [
+                    {
+                        "CoderSessionToken": []
+                    }
+                ],
+                "x-apidocgen": {
+                    "skip": true
+                }
+            },
+            "put": {
+                "consumes": [
+                    "application/json"
+                ],
+                "tags": [
+                    "Chats"
+                ],
+                "summary": "Update chat retention days",
+                "operationId": "update-chat-retention-days",
+                "parameters": [
+                    {
+                        "description": "Request body",
+                        "name": "request",
+                        "in": "body",
+                        "required": true,
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.UpdateChatRetentionDaysRequest"
+                        }
+                    }
+                ],
+                "responses": {
+                    "204": {
+                        "description": "No Content"
+                    }
+                },
+                "security": [
+                    {
+                        "CoderSessionToken": []
+                    }
+                ],
+                "x-apidocgen": {
+                    "skip": true
+                }
+            }
+        },
         "/experimental/watch-all-workspacebuilds": {
             "get": {
                 "produces": [
@@ -9452,6 +9514,212 @@ const docTemplate = `{
                 ]
             }
         },
+        "/users/{user}/secrets": {
+            "get": {
+                "produces": [
+                    "application/json"
+                ],
+                "tags": [
+                    "Secrets"
+                ],
+                "summary": "List user secrets",
+                "operationId": "list-user-secrets",
+                "parameters": [
+                    {
+                        "type": "string",
+                        "description": "User ID, username, or me",
+                        "name": "user",
+                        "in": "path",
+                        "required": true
+                    }
+                ],
+                "responses": {
+                    "200": {
+                        "description": "OK",
+                        "schema": {
+                            "type": "array",
+                            "items": {
+                                "$ref": "#/definitions/codersdk.UserSecret"
+                            }
+                        }
+                    }
+                },
+                "security": [
+                    {
+                        "CoderSessionToken": []
+                    }
+                ]
+            },
+            "post": {
+                "consumes": [
+                    "application/json"
+                ],
+                "produces": [
+                    "application/json"
+                ],
+                "tags": [
+                    "Secrets"
+                ],
+                "summary": "Create a new user secret",
+                "operationId": "create-a-new-user-secret",
+                "parameters": [
+                    {
+                        "type": "string",
+                        "description": "User ID, username, or me",
+                        "name": "user",
+                        "in": "path",
+                        "required": true
+                    },
+                    {
+                        "description": "Create secret request",
+                        "name": "request",
+                        "in": "body",
+                        "required": true,
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.CreateUserSecretRequest"
+                        }
+                    }
+                ],
+                "responses": {
+                    "201": {
+                        "description": "Created",
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.UserSecret"
+                        }
+                    }
+                },
+                "security": [
+                    {
+                        "CoderSessionToken": []
+                    }
+                ]
+            }
+        },
+        "/users/{user}/secrets/{name}": {
+            "get": {
+                "produces": [
+                    "application/json"
+                ],
+                "tags": [
+                    "Secrets"
+                ],
+                "summary": "Get a user secret by name",
+                "operationId": "get-a-user-secret-by-name",
+                "parameters": [
+                    {
+                        "type": "string",
+                        "description": "User ID, username, or me",
+                        "name": "user",
+                        "in": "path",
+                        "required": true
+                    },
+                    {
+                        "type": "string",
+                        "description": "Secret name",
+                        "name": "name",
+                        "in": "path",
+                        "required": true
+                    }
+                ],
+                "responses": {
+                    "200": {
+                        "description": "OK",
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.UserSecret"
+                        }
+                    }
+                },
+                "security": [
+                    {
+                        "CoderSessionToken": []
+                    }
+                ]
+            },
+            "delete": {
+                "tags": [
+                    "Secrets"
+                ],
+                "summary": "Delete a user secret",
+                "operationId": "delete-a-user-secret",
+                "parameters": [
+                    {
+                        "type": "string",
+                        "description": "User ID, username, or me",
+                        "name": "user",
+                        "in": "path",
+                        "required": true
+                    },
+                    {
+                        "type": "string",
+                        "description": "Secret name",
+                        "name": "name",
+                        "in": "path",
+                        "required": true
+                    }
+                ],
+                "responses": {
+                    "204": {
+                        "description": "No Content"
+                    }
+                },
+                "security": [
+                    {
+                        "CoderSessionToken": []
+                    }
+                ]
+            },
+            "patch": {
+                "consumes": [
+                    "application/json"
+                ],
+                "produces": [
+                    "application/json"
+                ],
+                "tags": [
+                    "Secrets"
+                ],
+                "summary": "Update a user secret",
+                "operationId": "update-a-user-secret",
+                "parameters": [
+                    {
+                        "type": "string",
+                        "description": "User ID, username, or me",
+                        "name": "user",
+                        "in": "path",
+                        "required": true
+                    },
+                    {
+                        "type": "string",
+                        "description": "Secret name",
+                        "name": "name",
+                        "in": "path",
+                        "required": true
+                    },
+                    {
+                        "description": "Update secret request",
+                        "name": "request",
+                        "in": "body",
+                        "required": true,
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.UpdateUserSecretRequest"
+                        }
+                    }
+                ],
+                "responses": {
+                    "200": {
+                        "description": "OK",
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.UserSecret"
+                        }
+                    }
+                },
+                "security": [
+                    {
+                        "CoderSessionToken": []
+                    }
+                ]
+            }
+        },
         "/users/{user}/status/activate": {
             "put": {
                 "produces": [
@@ -10205,12 +10473,26 @@ const docTemplate = `{
                 ],
                 "summary": "Get workspace agent reinitialization",
                 "operationId": "get-workspace-agent-reinitialization",
+                "parameters": [
+                    {
+                        "type": "boolean",
+                        "description": "Opt in to durable reinit checks",
+                        "name": "wait",
+                        "in": "query"
+                    }
+                ],
                 "responses": {
                     "200": {
                         "description": "OK",
                         "schema": {
                             "$ref": "#/definitions/agentsdk.ReinitializationEvent"
                         }
+                    },
+                    "409": {
+                        "description": "Conflict",
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.Response"
+                        }
                     }
                 },
                 "security": [
@@ -12647,11 +12929,16 @@ const docTemplate = `{
         "agentsdk.ReinitializationEvent": {
             "type": "object",
             "properties": {
+                "owner_id": {
+                    "type": "string",
+                    "format": "uuid"
+                },
                 "reason": {
                     "$ref": "#/definitions/agentsdk.ReinitializationReason"
                 },
-                "workspaceID": {
-                    "type": "string"
+                "workspace_id": {
+                    "type": "string",
+                    "format": "uuid"
                 }
             }
         },
@@ -12894,6 +13181,9 @@ const docTemplate = `{
                 "provider": {
                     "type": "string"
                 },
+                "provider_name": {
+                    "type": "string"
+                },
                 "started_at": {
                     "type": "string",
                     "format": "date-time"
@@ -13111,6 +13401,12 @@ const docTemplate = `{
         "codersdk.AIBridgeSessionThreadsTokenUsage": {
             "type": "object",
             "properties": {
+                "cache_read_input_tokens": {
+                    "type": "integer"
+                },
+                "cache_write_input_tokens": {
+                    "type": "integer"
+                },
                 "input_tokens": {
                     "type": "integer"
                 },
@@ -13126,6 +13422,12 @@ const docTemplate = `{
         "codersdk.AIBridgeSessionTokenUsageSummary": {
             "type": "object",
             "properties": {
+                "cache_read_input_tokens": {
+                    "type": "integer"
+                },
+                "cache_write_input_tokens": {
+                    "type": "integer"
+                },
                 "input_tokens": {
                     "type": "integer"
                 },
@@ -13143,6 +13445,12 @@ const docTemplate = `{
                         "$ref": "#/definitions/codersdk.AIBridgeAgenticAction"
                     }
                 },
+                "credential_hint": {
+                    "type": "string"
+                },
+                "credential_kind": {
+                    "type": "string"
+                },
                 "ended_at": {
                     "type": "string",
                     "format": "date-time"
@@ -13172,6 +13480,12 @@ const docTemplate = `{
         "codersdk.AIBridgeTokenUsage": {
             "type": "object",
             "properties": {
+                "cache_read_input_tokens": {
+                    "type": "integer"
+                },
+                "cache_write_input_tokens": {
+                    "type": "integer"
+                },
                 "created_at": {
                     "type": "string",
                     "format": "date-time"
@@ -13445,11 +13759,6 @@ const docTemplate = `{
                 "chat:delete",
                 "chat:read",
                 "chat:update",
-                "chat_automation:*",
-                "chat_automation:create",
-                "chat_automation:delete",
-                "chat_automation:read",
-                "chat_automation:update",
                 "coder:all",
                 "coder:apikeys.manage_self",
                 "coder:application_connect",
@@ -13659,11 +13968,6 @@ const docTemplate = `{
                 "APIKeyScopeChatDelete",
                 "APIKeyScopeChatRead",
                 "APIKeyScopeChatUpdate",
-                "APIKeyScopeChatAutomationAll",
-                "APIKeyScopeChatAutomationCreate",
-                "APIKeyScopeChatAutomationDelete",
-                "APIKeyScopeChatAutomationRead",
-                "APIKeyScopeChatAutomationUpdate",
                 "APIKeyScopeCoderAll",
                 "APIKeyScopeCoderApikeysManageSelf",
                 "APIKeyScopeCoderApplicationConnect",
@@ -14145,6 +14449,9 @@ const docTemplate = `{
                 },
                 "count": {
                     "type": "integer"
+                },
+                "count_cap": {
+                    "type": "integer"
                 }
             }
         },
@@ -14384,6 +14691,17 @@ const docTemplate = `{
             "properties": {
                 "acquire_batch_size": {
                     "type": "integer"
+                },
+                "debug_logging_enabled": {
+                    "type": "boolean"
+                }
+            }
+        },
+        "codersdk.ChatRetentionDaysResponse": {
+            "type": "object",
+            "properties": {
+                "retention_days": {
+                    "type": "integer"
                 }
             }
         },
@@ -14466,6 +14784,9 @@ const docTemplate = `{
                 },
                 "count": {
                     "type": "integer"
+                },
+                "count_cap": {
+                    "type": "integer"
                 }
             }
         },
@@ -14553,6 +14874,17 @@ const docTemplate = `{
                 }
             }
         },
+        "codersdk.CreateFirstUserOnboardingInfo": {
+            "type": "object",
+            "properties": {
+                "newsletter_marketing": {
+                    "type": "boolean"
+                },
+                "newsletter_releases": {
+                    "type": "boolean"
+                }
+            }
+        },
         "codersdk.CreateFirstUserRequest": {
             "type": "object",
             "required": [
@@ -14567,6 +14899,9 @@ const docTemplate = `{
                 "name": {
                     "type": "string"
                 },
+                "onboarding_info": {
+                    "$ref": "#/definitions/codersdk.CreateFirstUserOnboardingInfo"
+                },
                 "password": {
                     "type": "string"
                 },
@@ -15022,6 +15357,26 @@ const docTemplate = `{
                 }
             }
         },
+        "codersdk.CreateUserSecretRequest": {
+            "type": "object",
+            "properties": {
+                "description": {
+                    "type": "string"
+                },
+                "env_name": {
+                    "type": "string"
+                },
+                "file_path": {
+                    "type": "string"
+                },
+                "name": {
+                    "type": "string"
+                },
+                "value": {
+                    "type": "string"
+                }
+            }
+        },
         "codersdk.CreateWorkspaceBuildReason": {
             "type": "string",
             "enum": [
@@ -18797,6 +19152,9 @@ const docTemplate = `{
                 "template_version_name": {
                     "type": "string"
                 },
+                "workspace_build_transition": {
+                    "$ref": "#/definitions/codersdk.WorkspaceTransition"
+                },
                 "workspace_id": {
                     "type": "string",
                     "format": "uuid"
@@ -19048,7 +19406,6 @@ const docTemplate = `{
                 "audit_log",
                 "boundary_usage",
                 "chat",
-                "chat_automation",
                 "connection_log",
                 "crypto_key",
                 "debug_info",
@@ -19095,7 +19452,6 @@ const docTemplate = `{
                 "ResourceAuditLog",
                 "ResourceBoundaryUsage",
                 "ResourceChat",
-                "ResourceChatAutomation",
                 "ResourceConnectionLog",
                 "ResourceCryptoKey",
                 "ResourceDebugInfo",
@@ -20904,6 +21260,14 @@ const docTemplate = `{
                 }
             }
         },
+        "codersdk.UpdateChatRetentionDaysRequest": {
+            "type": "object",
+            "properties": {
+                "retention_days": {
+                    "type": "integer"
+                }
+            }
+        },
         "codersdk.UpdateCheckResponse": {
             "type": "object",
             "properties": {
@@ -21145,6 +21509,23 @@ const docTemplate = `{
                 }
             }
         },
+        "codersdk.UpdateUserSecretRequest": {
+            "type": "object",
+            "properties": {
+                "description": {
+                    "type": "string"
+                },
+                "env_name": {
+                    "type": "string"
+                },
+                "file_path": {
+                    "type": "string"
+                },
+                "value": {
+                    "type": "string"
+                }
+            }
+        },
         "codersdk.UpdateWorkspaceACL": {
             "type": "object",
             "properties": {
@@ -21600,6 +21981,35 @@ const docTemplate = `{
                 }
             }
         },
+        "codersdk.UserSecret": {
+            "type": "object",
+            "properties": {
+                "created_at": {
+                    "type": "string",
+                    "format": "date-time"
+                },
+                "description": {
+                    "type": "string"
+                },
+                "env_name": {
+                    "type": "string"
+                },
+                "file_path": {
+                    "type": "string"
+                },
+                "id": {
+                    "type": "string",
+                    "format": "uuid"
+                },
+                "name": {
+                    "type": "string"
+                },
+                "updated_at": {
+                    "type": "string",
+                    "format": "date-time"
+                }
+            }
+        },
         "codersdk.UserStatus": {
             "type": "string",
             "enum": [

coderd/apidoc/swagger.json

@@ -1103,6 +1103,60 @@
 				]
 			}
 		},
+		"/experimental/chats/config/retention-days": {
+			"get": {
+				"produces": ["application/json"],
+				"tags": ["Chats"],
+				"summary": "Get chat retention days",
+				"operationId": "get-chat-retention-days",
+				"responses": {
+					"200": {
+						"description": "OK",
+						"schema": {
+							"$ref": "#/definitions/codersdk.ChatRetentionDaysResponse"
+						}
+					}
+				},
+				"security": [
+					{
+						"CoderSessionToken": []
+					}
+				],
+				"x-apidocgen": {
+					"skip": true
+				}
+			},
+			"put": {
+				"consumes": ["application/json"],
+				"tags": ["Chats"],
+				"summary": "Update chat retention days",
+				"operationId": "update-chat-retention-days",
+				"parameters": [
+					{
+						"description": "Request body",
+						"name": "request",
+						"in": "body",
+						"required": true,
+						"schema": {
+							"$ref": "#/definitions/codersdk.UpdateChatRetentionDaysRequest"
+						}
+					}
+				],
+				"responses": {
+					"204": {
+						"description": "No Content"
+					}
+				},
+				"security": [
+					{
+						"CoderSessionToken": []
+					}
+				],
+				"x-apidocgen": {
+					"skip": true
+				}
+			}
+		},
 		"/experimental/watch-all-workspacebuilds": {
 			"get": {
 				"produces": ["application/json"],
@@ -8377,6 +8431,190 @@
 				]
 			}
 		},
+		"/users/{user}/secrets": {
+			"get": {
+				"produces": ["application/json"],
+				"tags": ["Secrets"],
+				"summary": "List user secrets",
+				"operationId": "list-user-secrets",
+				"parameters": [
+					{
+						"type": "string",
+						"description": "User ID, username, or me",
+						"name": "user",
+						"in": "path",
+						"required": true
+					}
+				],
+				"responses": {
+					"200": {
+						"description": "OK",
+						"schema": {
+							"type": "array",
+							"items": {
+								"$ref": "#/definitions/codersdk.UserSecret"
+							}
+						}
+					}
+				},
+				"security": [
+					{
+						"CoderSessionToken": []
+					}
+				]
+			},
+			"post": {
+				"consumes": ["application/json"],
+				"produces": ["application/json"],
+				"tags": ["Secrets"],
+				"summary": "Create a new user secret",
+				"operationId": "create-a-new-user-secret",
+				"parameters": [
+					{
+						"type": "string",
+						"description": "User ID, username, or me",
+						"name": "user",
+						"in": "path",
+						"required": true
+					},
+					{
+						"description": "Create secret request",
+						"name": "request",
+						"in": "body",
+						"required": true,
+						"schema": {
+							"$ref": "#/definitions/codersdk.CreateUserSecretRequest"
+						}
+					}
+				],
+				"responses": {
+					"201": {
+						"description": "Created",
+						"schema": {
+							"$ref": "#/definitions/codersdk.UserSecret"
+						}
+					}
+				},
+				"security": [
+					{
+						"CoderSessionToken": []
+					}
+				]
+			}
+		},
+		"/users/{user}/secrets/{name}": {
+			"get": {
+				"produces": ["application/json"],
+				"tags": ["Secrets"],
+				"summary": "Get a user secret by name",
+				"operationId": "get-a-user-secret-by-name",
+				"parameters": [
+					{
+						"type": "string",
+						"description": "User ID, username, or me",
+						"name": "user",
+						"in": "path",
+						"required": true
+					},
+					{
+						"type": "string",
+						"description": "Secret name",
+						"name": "name",
+						"in": "path",
+						"required": true
+					}
+				],
+				"responses": {
+					"200": {
+						"description": "OK",
+						"schema": {
+							"$ref": "#/definitions/codersdk.UserSecret"
+						}
+					}
+				},
+				"security": [
+					{
+						"CoderSessionToken": []
+					}
+				]
+			},
+			"delete": {
+				"tags": ["Secrets"],
+				"summary": "Delete a user secret",
+				"operationId": "delete-a-user-secret",
+				"parameters": [
+					{
+						"type": "string",
+						"description": "User ID, username, or me",
+						"name": "user",
+						"in": "path",
+						"required": true
+					},
+					{
+						"type": "string",
+						"description": "Secret name",
+						"name": "name",
+						"in": "path",
+						"required": true
+					}
+				],
+				"responses": {
+					"204": {
+						"description": "No Content"
+					}
+				},
+				"security": [
+					{
+						"CoderSessionToken": []
+					}
+				]
+			},
+			"patch": {
+				"consumes": ["application/json"],
+				"produces": ["application/json"],
+				"tags": ["Secrets"],
+				"summary": "Update a user secret",
+				"operationId": "update-a-user-secret",
+				"parameters": [
+					{
+						"type": "string",
+						"description": "User ID, username, or me",
+						"name": "user",
+						"in": "path",
+						"required": true
+					},
+					{
+						"type": "string",
+						"description": "Secret name",
+						"name": "name",
+						"in": "path",
+						"required": true
+					},
+					{
+						"description": "Update secret request",
+						"name": "request",
+						"in": "body",
+						"required": true,
+						"schema": {
+							"$ref": "#/definitions/codersdk.UpdateUserSecretRequest"
+						}
+					}
+				],
+				"responses": {
+					"200": {
+						"description": "OK",
+						"schema": {
+							"$ref": "#/definitions/codersdk.UserSecret"
+						}
+					}
+				},
+				"security": [
+					{
+						"CoderSessionToken": []
+					}
+				]
+			}
+		},
 		"/users/{user}/status/activate": {
 			"put": {
 				"produces": ["application/json"],
@@ -9038,12 +9276,26 @@
 				"tags": ["Agents"],
 				"summary": "Get workspace agent reinitialization",
 				"operationId": "get-workspace-agent-reinitialization",
+				"parameters": [
+					{
+						"type": "boolean",
+						"description": "Opt in to durable reinit checks",
+						"name": "wait",
+						"in": "query"
+					}
+				],
 				"responses": {
 					"200": {
 						"description": "OK",
 						"schema": {
 							"$ref": "#/definitions/agentsdk.ReinitializationEvent"
 						}
+					},
+					"409": {
+						"description": "Conflict",
+						"schema": {
+							"$ref": "#/definitions/codersdk.Response"
+						}
 					}
 				},
 				"security": [
@@ -11229,11 +11481,16 @@
 		"agentsdk.ReinitializationEvent": {
 			"type": "object",
 			"properties": {
+				"owner_id": {
+					"type": "string",
+					"format": "uuid"
+				},
 				"reason": {
 					"$ref": "#/definitions/agentsdk.ReinitializationReason"
 				},
-				"workspaceID": {
-					"type": "string"
+				"workspace_id": {
+					"type": "string",
+					"format": "uuid"
 				}
 			}
 		},
@@ -11472,6 +11729,9 @@
 				"provider": {
 					"type": "string"
 				},
+				"provider_name": {
+					"type": "string"
+				},
 				"started_at": {
 					"type": "string",
 					"format": "date-time"
@@ -11689,6 +11949,12 @@
 		"codersdk.AIBridgeSessionThreadsTokenUsage": {
 			"type": "object",
 			"properties": {
+				"cache_read_input_tokens": {
+					"type": "integer"
+				},
+				"cache_write_input_tokens": {
+					"type": "integer"
+				},
 				"input_tokens": {
 					"type": "integer"
 				},
@@ -11704,6 +11970,12 @@
 		"codersdk.AIBridgeSessionTokenUsageSummary": {
 			"type": "object",
 			"properties": {
+				"cache_read_input_tokens": {
+					"type": "integer"
+				},
+				"cache_write_input_tokens": {
+					"type": "integer"
+				},
 				"input_tokens": {
 					"type": "integer"
 				},
@@ -11721,6 +11993,12 @@
 						"$ref": "#/definitions/codersdk.AIBridgeAgenticAction"
 					}
 				},
+				"credential_hint": {
+					"type": "string"
+				},
+				"credential_kind": {
+					"type": "string"
+				},
 				"ended_at": {
 					"type": "string",
 					"format": "date-time"
@@ -11750,6 +12028,12 @@
 		"codersdk.AIBridgeTokenUsage": {
 			"type": "object",
 			"properties": {
+				"cache_read_input_tokens": {
+					"type": "integer"
+				},
+				"cache_write_input_tokens": {
+					"type": "integer"
+				},
 				"created_at": {
 					"type": "string",
 					"format": "date-time"
@@ -12015,11 +12299,6 @@
 				"chat:delete",
 				"chat:read",
 				"chat:update",
-				"chat_automation:*",
-				"chat_automation:create",
-				"chat_automation:delete",
-				"chat_automation:read",
-				"chat_automation:update",
 				"coder:all",
 				"coder:apikeys.manage_self",
 				"coder:application_connect",
@@ -12229,11 +12508,6 @@
 				"APIKeyScopeChatDelete",
 				"APIKeyScopeChatRead",
 				"APIKeyScopeChatUpdate",
-				"APIKeyScopeChatAutomationAll",
-				"APIKeyScopeChatAutomationCreate",
-				"APIKeyScopeChatAutomationDelete",
-				"APIKeyScopeChatAutomationRead",
-				"APIKeyScopeChatAutomationUpdate",
 				"APIKeyScopeCoderAll",
 				"APIKeyScopeCoderApikeysManageSelf",
 				"APIKeyScopeCoderApplicationConnect",
@@ -12709,6 +12983,9 @@
 				},
 				"count": {
 					"type": "integer"
+				},
+				"count_cap": {
+					"type": "integer"
 				}
 			}
 		},
@@ -12927,6 +13204,17 @@
 			"properties": {
 				"acquire_batch_size": {
 					"type": "integer"
+				},
+				"debug_logging_enabled": {
+					"type": "boolean"
+				}
+			}
+		},
+		"codersdk.ChatRetentionDaysResponse": {
+			"type": "object",
+			"properties": {
+				"retention_days": {
+					"type": "integer"
 				}
 			}
 		},
@@ -13009,6 +13297,9 @@
 				},
 				"count": {
 					"type": "integer"
+				},
+				"count_cap": {
+					"type": "integer"
 				}
 			}
 		},
@@ -13093,6 +13384,17 @@
 				}
 			}
 		},
+		"codersdk.CreateFirstUserOnboardingInfo": {
+			"type": "object",
+			"properties": {
+				"newsletter_marketing": {
+					"type": "boolean"
+				},
+				"newsletter_releases": {
+					"type": "boolean"
+				}
+			}
+		},
 		"codersdk.CreateFirstUserRequest": {
 			"type": "object",
 			"required": ["email", "password", "username"],
@@ -13103,6 +13405,9 @@
 				"name": {
 					"type": "string"
 				},
+				"onboarding_info": {
+					"$ref": "#/definitions/codersdk.CreateFirstUserOnboardingInfo"
+				},
 				"password": {
 					"type": "string"
 				},
@@ -13531,6 +13836,26 @@
 				}
 			}
 		},
+		"codersdk.CreateUserSecretRequest": {
+			"type": "object",
+			"properties": {
+				"description": {
+					"type": "string"
+				},
+				"env_name": {
+					"type": "string"
+				},
+				"file_path": {
+					"type": "string"
+				},
+				"name": {
+					"type": "string"
+				},
+				"value": {
+					"type": "string"
+				}
+			}
+		},
 		"codersdk.CreateWorkspaceBuildReason": {
 			"type": "string",
 			"enum": [
@@ -17187,6 +17512,9 @@
 				"template_version_name": {
 					"type": "string"
 				},
+				"workspace_build_transition": {
+					"$ref": "#/definitions/codersdk.WorkspaceTransition"
+				},
 				"workspace_id": {
 					"type": "string",
 					"format": "uuid"
@@ -17420,7 +17748,6 @@
 				"audit_log",
 				"boundary_usage",
 				"chat",
-				"chat_automation",
 				"connection_log",
 				"crypto_key",
 				"debug_info",
@@ -17467,7 +17794,6 @@
 				"ResourceAuditLog",
 				"ResourceBoundaryUsage",
 				"ResourceChat",
-				"ResourceChatAutomation",
 				"ResourceConnectionLog",
 				"ResourceCryptoKey",
 				"ResourceDebugInfo",
@@ -19195,6 +19521,14 @@
 				}
 			}
 		},
+		"codersdk.UpdateChatRetentionDaysRequest": {
+			"type": "object",
+			"properties": {
+				"retention_days": {
+					"type": "integer"
+				}
+			}
+		},
 		"codersdk.UpdateCheckResponse": {
 			"type": "object",
 			"properties": {
@@ -19427,6 +19761,23 @@
 				}
 			}
 		},
+		"codersdk.UpdateUserSecretRequest": {
+			"type": "object",
+			"properties": {
+				"description": {
+					"type": "string"
+				},
+				"env_name": {
+					"type": "string"
+				},
+				"file_path": {
+					"type": "string"
+				},
+				"value": {
+					"type": "string"
+				}
+			}
+		},
 		"codersdk.UpdateWorkspaceACL": {
 			"type": "object",
 			"properties": {
@@ -19857,6 +20208,35 @@
 				}
 			}
 		},
+		"codersdk.UserSecret": {
+			"type": "object",
+			"properties": {
+				"created_at": {
+					"type": "string",
+					"format": "date-time"
+				},
+				"description": {
+					"type": "string"
+				},
+				"env_name": {
+					"type": "string"
+				},
+				"file_path": {
+					"type": "string"
+				},
+				"id": {
+					"type": "string",
+					"format": "uuid"
+				},
+				"name": {
+					"type": "string"
+				},
+				"updated_at": {
+					"type": "string",
+					"format": "date-time"
+				}
+			}
+		},
 		"codersdk.UserStatus": {
 			"type": "string",
 			"enum": ["active", "dormant", "suspended"],

coderd/apikey.go

@@ -582,5 +582,20 @@ func (api *API) createAPIKey(ctx context.Context, params apikey.CreateParams) (*
 		Value:    sessionToken,
 		Path:     "/",
 		HttpOnly: true,
+		// MaxAge is set so the browser persists the cookie to disk rather
+		// than keeping it in memory as a session cookie. Standalone PWAs
+		// (display: standalone) run in their own browser process, and
+		// mobile OSes kill that process when the app is swiped away —
+		// deleting in-memory cookies and forcing an unexpected login.
+		//
+		// We use a long static value (1 year) instead of the key's
+		// LifetimeSeconds because the server refreshes the key's
+		// ExpiresAt on activity but does not re-set the cookie. Tying
+		// MaxAge to the key lifetime would cause the cookie to expire
+		// client-side even when the server-side key is still valid.
+		//
+		// Security is not affected: the server validates ExpiresAt on
+		// every request regardless of the cookie's MaxAge.
+		MaxAge: int((365 * 24 * time.Hour).Seconds()),
 	}), &newkey, nil
 }

coderd/apikey_test.go

@@ -394,6 +394,55 @@ func TestSessionExpiry(t *testing.T) {
 	}
 }
 
+// TestSessionCookieMaxAge verifies that the session cookie is a persistent
+// cookie (has MaxAge set) rather than a session cookie. Standalone PWAs
+// run in their own browser process and mobile OSes purge in-memory
+// (session) cookies when that process is killed, so the cookie must be
+// persisted to disk.
+func TestSessionCookieMaxAge(t *testing.T) {
+	t.Parallel()
+
+	ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
+	defer cancel()
+
+	client := coderdtest.New(t, nil)
+
+	// Create the first user (password-based login).
+	req := codersdk.CreateFirstUserRequest{
+		Email:    "testuser@coder.com",
+		Username: "testuser",
+		Password: "SomeSecurePassword!",
+	}
+	_, err := client.CreateFirstUser(ctx, req)
+	require.NoError(t, err)
+
+	// Login via the raw HTTP endpoint so we can inspect the Set-Cookie header.
+	loginURL, err := client.URL.Parse("/api/v2/users/login")
+	require.NoError(t, err)
+
+	res, err := client.Request(ctx, http.MethodPost, loginURL.String(), codersdk.LoginWithPasswordRequest{
+		Email:    req.Email,
+		Password: req.Password,
+	})
+	require.NoError(t, err)
+	defer res.Body.Close()
+	require.Equal(t, http.StatusCreated, res.StatusCode)
+
+	oneYear := int((365 * 24 * time.Hour).Seconds())
+	var found bool
+	for _, cookie := range res.Cookies() {
+		if cookie.Name == codersdk.SessionTokenCookie {
+			// MaxAge should be set to a long value so the browser
+			// persists the cookie to disk. The server handles real
+			// expiry via the API key's ExpiresAt field.
+			require.Equal(t, oneYear, cookie.MaxAge,
+				"Session cookie MaxAge should be set to 1 year for disk persistence")
+			found = true
+		}
+	}
+	require.True(t, found, "session cookie should be present in login response")
+}
+
 func TestAPIKey_OK(t *testing.T) {
 	t.Parallel()
 

coderd/audit.go

@@ -26,6 +26,11 @@ import (
 	"github.com/coder/coder/v2/codersdk"
 )
 
+// Limit the count query to avoid a slow sequential scan due to joins
+// on a large table. Set to 0 to disable capping (but also see the note
+// in the SQL query).
+const auditLogCountCap = 2000
+
 // @Summary Get audit logs
 // @ID get-audit-logs
 // @Security CoderSessionToken
@@ -66,7 +71,7 @@ func (api *API) auditLogs(rw http.ResponseWriter, r *http.Request) {
 		countFilter.Username = ""
 	}
 
-	// Use the same filters to count the number of audit logs
+	countFilter.CountCap = auditLogCountCap
 	count, err := api.Database.CountAuditLogs(ctx, countFilter)
 	if dbauthz.IsNotAuthorizedError(err) {
 		httpapi.Forbidden(rw)
@@ -81,6 +86,7 @@ func (api *API) auditLogs(rw http.ResponseWriter, r *http.Request) {
 		httpapi.Write(ctx, rw, http.StatusOK, codersdk.AuditLogResponse{
 			AuditLogs: []codersdk.AuditLog{},
 			Count:     0,
+			CountCap:  auditLogCountCap,
 		})
 		return
 	}
@@ -98,6 +104,7 @@ func (api *API) auditLogs(rw http.ResponseWriter, r *http.Request) {
 	httpapi.Write(ctx, rw, http.StatusOK, codersdk.AuditLogResponse{
 		AuditLogs: api.convertAuditLogs(ctx, dblogs),
 		Count:     count,
+		CountCap:  auditLogCountCap,
 	})
 }
 

coderd/coderd.go

@@ -168,6 +168,7 @@ type Options struct {
 	ConnectionLogger               connectionlog.ConnectionLogger
 	AgentConnectionUpdateFrequency time.Duration
 	AgentInactiveDisconnectTimeout time.Duration
+	ChatdInstructionLookupTimeout  time.Duration
 	AWSCertificates                awsidentity.Certificates
 	Authorizer                     rbac.Authorizer
 	AzureCertificates              x509.VerifyOptions
@@ -782,9 +783,10 @@ func New(options *Options) *API {
 			ReplicaID:                      api.ID,
 			SubscribeFn:                    options.ChatSubscribeFn,
 			MaxChatsPerAcquire:             int32(maxChatsPerAcquire), //nolint:gosec // maxChatsPerAcquire is clamped to int32 range above.
-			ProviderAPIKeys:                chatProviderAPIKeysFromDeploymentValues(options.DeploymentValues),
+			ProviderAPIKeys:                ChatProviderAPIKeysFromDeploymentValues(options.DeploymentValues),
 			AgentConn:                      api.agentProvider.AgentConn,
 			AgentInactiveDisconnectTimeout: api.AgentInactiveDisconnectTimeout,
+			InstructionLookupTimeout:       options.ChatdInstructionLookupTimeout,
 			CreateWorkspace:                api.chatCreateWorkspace,
 			StartWorkspace:                 api.chatStartWorkspace,
 			Pubsub:                         options.Pubsub,
@@ -1187,6 +1189,8 @@ func New(options *Options) *API {
 				r.Delete("/user-compaction-thresholds/{modelConfig}", api.deleteUserChatCompactionThreshold)
 				r.Get("/workspace-ttl", api.getChatWorkspaceTTL)
 				r.Put("/workspace-ttl", api.putChatWorkspaceTTL)
+				r.Get("/retention-days", api.getChatRetentionDays)
+				r.Put("/retention-days", api.putChatRetentionDays)
 				r.Get("/template-allowlist", api.getChatTemplateAllowlist)
 				r.Put("/template-allowlist", api.putChatTemplateAllowlist)
 			})
@@ -1221,6 +1225,13 @@ func New(options *Options) *API {
 					r.Delete("/", api.deleteChatUsageLimitGroupOverride)
 				})
 			})
+			r.Route("/user-provider-configs", func(r chi.Router) {
+				r.Get("/", api.listUserChatProviderConfigs)
+				r.Route("/{providerConfig}", func(r chi.Router) {
+					r.Put("/", api.upsertUserChatProviderKey)
+					r.Delete("/", api.deleteUserChatProviderKey)
+				})
+			})
 			r.Route("/{chat}", func(r chi.Router) {
 				r.Use(httpmw.ExtractChatParam(options.Database))
 				r.Get("/", api.getChat)
@@ -1234,6 +1245,7 @@ func New(options *Options) *API {
 					r.Get("/git", api.watchChatGit)
 				})
 				r.Post("/interrupt", api.interruptChat)
+				r.Post("/tool-results", api.postChatToolResults)
 				r.Post("/title/regenerate", api.regenerateChatTitle)
 				r.Get("/diff", api.getChatDiffContents)
 				r.Route("/queue/{queuedMessage}", func(r chi.Router) {
@@ -1596,6 +1608,15 @@ func New(options *Options) *API {
 
 						r.Get("/gitsshkey", api.gitSSHKey)
 						r.Put("/gitsshkey", api.regenerateGitSSHKey)
+						r.Route("/secrets", func(r chi.Router) {
+							r.Post("/", api.postUserSecret)
+							r.Get("/", api.getUserSecrets)
+							r.Route("/{name}", func(r chi.Router) {
+								r.Get("/", api.getUserSecret)
+								r.Patch("/", api.patchUserSecret)
+								r.Delete("/", api.deleteUserSecret)
+							})
+						})
 						r.Route("/notifications", func(r chi.Router) {
 							r.Route("/preferences", func(r chi.Router) {
 								r.Get("/", api.userNotificationPreferences)
@@ -1641,6 +1662,10 @@ func New(options *Options) *API {
 				r.Get("/gitsshkey", api.agentGitSSHKey)
 				r.Post("/log-source", api.workspaceAgentPostLogSource)
 				r.Get("/reinit", api.workspaceAgentReinit)
+				r.Route("/experimental", func(r chi.Router) {
+					r.Post("/chat-context", api.workspaceAgentAddChatContext)
+					r.Delete("/chat-context", api.workspaceAgentClearChatContext)
+				})
 				r.Route("/tasks/{task}", func(r chi.Router) {
 					r.Post("/log-snapshot", api.postWorkspaceAgentTaskLogSnapshot)
 				})

coderd/coderdtest/coderdtest.go

@@ -149,12 +149,13 @@ type Options struct {
 	OneTimePasscodeValidityPeriod time.Duration
 
 	// IncludeProvisionerDaemon when true means to start an in-memory provisionerD
-	IncludeProvisionerDaemon    bool
-	ProvisionerDaemonVersion    string
-	ProvisionerDaemonTags       map[string]string
-	MetricsCacheRefreshInterval time.Duration
-	AgentStatsRefreshInterval   time.Duration
-	DeploymentValues            *codersdk.DeploymentValues
+	IncludeProvisionerDaemon      bool
+	ChatdInstructionLookupTimeout time.Duration
+	ProvisionerDaemonVersion      string
+	ProvisionerDaemonTags         map[string]string
+	MetricsCacheRefreshInterval   time.Duration
+	AgentStatsRefreshInterval     time.Duration
+	DeploymentValues              *codersdk.DeploymentValues
 
 	// Set update check options to enable update check.
 	UpdateCheckOptions *updatecheck.Options
@@ -575,6 +576,7 @@ func NewOptions(t testing.TB, options *Options) (func(http.Handler), context.Can
 			// Force a long disconnection timeout to ensure
 			// agents are not marked as disconnected during slow tests.
 			AgentInactiveDisconnectTimeout: testutil.WaitShort,
+			ChatdInstructionLookupTimeout:  options.ChatdInstructionLookupTimeout,
 			AccessURL:                      accessURL,
 			AppHostname:                    options.AppHostname,
 			AppHostnameRegex:               appHostnameRegex,

coderd/coderdtest/swaggerparser.go

@@ -147,6 +147,10 @@ func parseSwaggerComment(commentGroup *ast.CommentGroup) SwaggerComment {
 	return c
 }
 
+func isExperimentalEndpoint(route string) bool {
+	return strings.HasPrefix(route, "/workspaceagents/me/experimental/")
+}
+
 func VerifySwaggerDefinitions(t *testing.T, router chi.Router, swaggerComments []SwaggerComment) {
 	assertUniqueRoutes(t, swaggerComments)
 	assertSingleAnnotations(t, swaggerComments)
@@ -165,6 +169,9 @@ func VerifySwaggerDefinitions(t *testing.T, router chi.Router, swaggerComments [
 			if strings.HasSuffix(route, "/*") {
 				return
 			}
+			if isExperimentalEndpoint(route) {
+				return
+			}
 
 			c := findSwaggerCommentByMethodAndRoute(swaggerComments, method, route)
 			assert.NotNil(t, c, "Missing @Router annotation")

coderd/coderdtest/users.go

@@ -123,6 +123,10 @@ func UsersPagination(
 	require.Contains(t, gotUsers[0].Name, "after")
 }
 
+type UsersFilterOptions struct {
+	CreateServiceAccounts bool
+}
+
 // UsersFilter creates a set of users to run various filters against for
 // testing.  It can be used to test filtering both users and group members.
 func UsersFilter(
@@ -130,11 +134,16 @@ func UsersFilter(
 	t *testing.T,
 	client *codersdk.Client,
 	db database.Store,
+	options *UsersFilterOptions,
 	setup func(users []codersdk.User),
 	fetch func(ctx context.Context, req codersdk.UsersRequest) []codersdk.ReducedUser,
 ) {
 	t.Helper()
 
+	if options == nil {
+		options = &UsersFilterOptions{}
+	}
+
 	firstUser, err := client.User(setupCtx, codersdk.Me)
 	require.NoError(t, err, "fetch me")
 
@@ -211,11 +220,13 @@ func UsersFilter(
 	}
 
 	// Add some service accounts.
-	for range 3 {
-		_, user := CreateAnotherUserMutators(t, client, orgID, nil, func(r *codersdk.CreateUserRequestWithOrgs) {
-			r.ServiceAccount = true
-		})
-		users = append(users, user)
+	if options.CreateServiceAccounts {
+		for range 3 {
+			_, user := CreateAnotherUserMutators(t, client, orgID, nil, func(r *codersdk.CreateUserRequestWithOrgs) {
+				r.ServiceAccount = true
+			})
+			users = append(users, user)
+		}
 	}
 
 	hashedPassword, err := userpassword.Hash("SomeStrongPassword!")

coderd/connectionlog/connectionlog.go

@@ -90,8 +90,8 @@ func (m *FakeConnectionLogger) Contains(t testing.TB, expected database.UpsertCo
 			t.Logf("connection log %d: expected Code %d, got %d", idx+1, expected.Code.Int32, cl.Code.Int32)
 			continue
 		}
-		if expected.Ip.Valid && cl.Ip.IPNet.String() != expected.Ip.IPNet.String() {
-			t.Logf("connection log %d: expected IP %s, got %s", idx+1, expected.Ip.IPNet, cl.Ip.IPNet)
+		if expected.IP.Valid && cl.IP.IPNet.String() != expected.IP.IPNet.String() {
+			t.Logf("connection log %d: expected IP %s, got %s", idx+1, expected.IP.IPNet, cl.IP.IPNet)
 			continue
 		}
 		if expected.UserAgent.Valid && cl.UserAgent.String != expected.UserAgent.String {

coderd/database/check_constraint.go

@@ -7,14 +7,10 @@ type CheckConstraint string
 // CheckConstraint enums.
 const (
 	CheckAPIKeysAllowListNotEmpty                    CheckConstraint = "api_keys_allow_list_not_empty"                      // api_keys
-	CheckChatAutomationEventsChatExclusivity         CheckConstraint = "chat_automation_events_chat_exclusivity"            // chat_automation_events
-	CheckChatAutomationTriggersCronFields            CheckConstraint = "chat_automation_triggers_cron_fields"               // chat_automation_triggers
-	CheckChatAutomationTriggersWebhookFields         CheckConstraint = "chat_automation_triggers_webhook_fields"            // chat_automation_triggers
-	CheckChatAutomationsMaxChatCreatesPerHourCheck   CheckConstraint = "chat_automations_max_chat_creates_per_hour_check"   // chat_automations
-	CheckChatAutomationsMaxMessagesPerHourCheck      CheckConstraint = "chat_automations_max_messages_per_hour_check"       // chat_automations
 	CheckChatModelConfigsCompressionThresholdCheck   CheckConstraint = "chat_model_configs_compression_threshold_check"     // chat_model_configs
 	CheckChatModelConfigsContextLimitCheck           CheckConstraint = "chat_model_configs_context_limit_check"             // chat_model_configs
 	CheckChatProvidersProviderCheck                  CheckConstraint = "chat_providers_provider_check"                      // chat_providers
+	CheckValidCredentialPolicy                       CheckConstraint = "valid_credential_policy"                            // chat_providers
 	CheckChatUsageLimitConfigDefaultLimitMicrosCheck CheckConstraint = "chat_usage_limit_config_default_limit_micros_check" // chat_usage_limit_config
 	CheckChatUsageLimitConfigPeriodCheck             CheckConstraint = "chat_usage_limit_config_period_check"               // chat_usage_limit_config
 	CheckChatUsageLimitConfigSingletonCheck          CheckConstraint = "chat_usage_limit_config_singleton_check"            // chat_usage_limit_config
@@ -37,4 +33,5 @@ const (
 	CheckTelemetryLockEventTypeConstraint            CheckConstraint = "telemetry_lock_event_type_constraint"               // telemetry_locks
 	CheckValidationMonotonicOrder                    CheckConstraint = "validation_monotonic_order"                         // template_version_parameters
 	CheckUsageEventTypeCheck                         CheckConstraint = "usage_event_type_check"                             // usage_events
+	CheckUserChatProviderKeysAPIKeyCheck             CheckConstraint = "user_chat_provider_keys_api_key_check"              // user_chat_provider_keys
 )

coderd/database/db2sdk/db2sdk.go

@@ -538,6 +538,12 @@ func WorkspaceAgent(derpMap *tailcfg.DERPMap, coordinator tailnet.Coordinator,
 	switch {
 	case workspaceAgent.Status != codersdk.WorkspaceAgentConnected && workspaceAgent.LifecycleState == codersdk.WorkspaceAgentLifecycleOff:
 		workspaceAgent.Health.Reason = "agent is not running"
+	case workspaceAgent.Status == codersdk.WorkspaceAgentConnecting:
+		// Note: the case above catches connecting+off as "not running".
+		// This case handles connecting agents with a non-off lifecycle
+		// (e.g. "created" or "starting"), where the agent binary has
+		// not yet established a connection to coderd.
+		workspaceAgent.Health.Reason = "agent has not yet connected"
 	case workspaceAgent.Status == codersdk.WorkspaceAgentTimeout:
 		workspaceAgent.Health.Reason = "agent is taking too long to connect"
 	case workspaceAgent.Status == codersdk.WorkspaceAgentDisconnected:
@@ -999,15 +1005,16 @@ func AIBridgeInterception(interception database.AIBridgeInterception, initiator
 		return sdkToolUsages[i].CreatedAt.Before(sdkToolUsages[j].CreatedAt)
 	})
 	intc := codersdk.AIBridgeInterception{
-		ID:          interception.ID,
-		Initiator:   MinimalUserFromVisibleUser(initiator),
-		Provider:    interception.Provider,
-		Model:       interception.Model,
-		Metadata:    jsonOrEmptyMap(interception.Metadata),
-		StartedAt:   interception.StartedAt,
-		TokenUsages: sdkTokenUsages,
-		UserPrompts: sdkUserPrompts,
-		ToolUsages:  sdkToolUsages,
+		ID:           interception.ID,
+		Initiator:    MinimalUserFromVisibleUser(initiator),
+		Provider:     interception.Provider,
+		ProviderName: interception.ProviderName,
+		Model:        interception.Model,
+		Metadata:     jsonOrEmptyMap(interception.Metadata),
+		StartedAt:    interception.StartedAt,
+		TokenUsages:  sdkTokenUsages,
+		UserPrompts:  sdkUserPrompts,
+		ToolUsages:   sdkToolUsages,
 	}
 	if interception.APIKeyID.Valid {
 		intc.APIKeyID = &interception.APIKeyID.String
@@ -1036,8 +1043,10 @@ func AIBridgeSession(row database.ListAIBridgeSessionsRow) codersdk.AIBridgeSess
 		StartedAt: row.StartedAt,
 		Threads:   row.Threads,
 		TokenUsageSummary: codersdk.AIBridgeSessionTokenUsageSummary{
-			InputTokens:  row.InputTokens,
-			OutputTokens: row.OutputTokens,
+			InputTokens:           row.InputTokens,
+			OutputTokens:          row.OutputTokens,
+			CacheReadInputTokens:  row.CacheReadInputTokens,
+			CacheWriteInputTokens: row.CacheWriteInputTokens,
 		},
 	}
 	// Ensure non-nil slices for JSON serialization.
@@ -1061,13 +1070,15 @@ func AIBridgeSession(row database.ListAIBridgeSessionsRow) codersdk.AIBridgeSess
 
 func AIBridgeTokenUsage(usage database.AIBridgeTokenUsage) codersdk.AIBridgeTokenUsage {
 	return codersdk.AIBridgeTokenUsage{
-		ID:                 usage.ID,
-		InterceptionID:     usage.InterceptionID,
-		ProviderResponseID: usage.ProviderResponseID,
-		InputTokens:        usage.InputTokens,
-		OutputTokens:       usage.OutputTokens,
-		Metadata:           jsonOrEmptyMap(usage.Metadata),
-		CreatedAt:          usage.CreatedAt,
+		ID:                    usage.ID,
+		InterceptionID:        usage.InterceptionID,
+		ProviderResponseID:    usage.ProviderResponseID,
+		InputTokens:           usage.InputTokens,
+		OutputTokens:          usage.OutputTokens,
+		CacheReadInputTokens:  usage.CacheReadInputTokens,
+		CacheWriteInputTokens: usage.CacheWriteInputTokens,
+		Metadata:              jsonOrEmptyMap(usage.Metadata),
+		CreatedAt:             usage.CreatedAt,
 	}
 }
 
@@ -1178,9 +1189,11 @@ func AIBridgeSessionThreads(
 		PageStartedAt: pageStartedAt,
 		PageEndedAt:   pageEndedAt,
 		TokenUsageSummary: codersdk.AIBridgeSessionThreadsTokenUsage{
-			InputTokens:  session.InputTokens,
-			OutputTokens: session.OutputTokens,
-			Metadata:     sessionTokenMeta,
+			InputTokens:           session.InputTokens,
+			OutputTokens:          session.OutputTokens,
+			CacheReadInputTokens:  session.CacheReadInputTokens,
+			CacheWriteInputTokens: session.CacheWriteInputTokens,
+			Metadata:              sessionTokenMeta,
 		},
 		Threads: threads,
 	}
@@ -1227,6 +1240,8 @@ func buildAIBridgeThread(
 	if rootIntc != nil {
 		thread.Model = rootIntc.Model
 		thread.Provider = rootIntc.Provider
+		thread.CredentialKind = string(rootIntc.CredentialKind)
+		thread.CredentialHint = rootIntc.CredentialHint
 		// Get first user prompt from root interception.
 		// A thread can only have one prompt, by definition, since we currently
 		// only store the last prompt observed in an interception.
@@ -1313,17 +1328,19 @@ func buildAIBridgeThread(
 
 // aggregateTokenUsage sums token usage rows and aggregates metadata.
 func aggregateTokenUsage(tokens []database.AIBridgeTokenUsage) codersdk.AIBridgeSessionThreadsTokenUsage {
-	var inputTokens, outputTokens int64
+	var inputTokens, outputTokens, cacheRead, cacheWrite int64
 	for _, tu := range tokens {
 		inputTokens += tu.InputTokens
 		outputTokens += tu.OutputTokens
-		// TODO: once https://github.com/coder/aibridge/issues/150 lands we
-		// should aggregate the other token types.
+		cacheRead += tu.CacheReadInputTokens
+		cacheWrite += tu.CacheWriteInputTokens
 	}
 	return codersdk.AIBridgeSessionThreadsTokenUsage{
-		InputTokens:  inputTokens,
-		OutputTokens: outputTokens,
-		Metadata:     aggregateTokenMetadata(tokens),
+		InputTokens:           inputTokens,
+		OutputTokens:          outputTokens,
+		CacheReadInputTokens:  cacheRead,
+		CacheWriteInputTokens: cacheWrite,
+		Metadata:              aggregateTokenMetadata(tokens),
 	}
 }
 
@@ -1516,10 +1533,29 @@ func nullInt64Ptr(v sql.NullInt64) *int64 {
 	return &value
 }
 
+func nullStringPtr(v sql.NullString) *string {
+	if !v.Valid {
+		return nil
+	}
+	value := v.String
+	return &value
+}
+
+func nullTimePtr(v sql.NullTime) *time.Time {
+	if !v.Valid {
+		return nil
+	}
+	value := v.Time
+	return &value
+}
+
 // Chat converts a database.Chat to a codersdk.Chat. It coalesces
 // nil slices and maps to empty values for JSON serialization and
 // derives RootChatID from the parent chain when not explicitly set.
-func Chat(c database.Chat, diffStatus *database.ChatDiffStatus) codersdk.Chat {
+// When diffStatus is non-nil the response includes diff metadata.
+// When files is non-empty the response includes file metadata;
+// pass nil to omit the files field (e.g. list endpoints).
+func Chat(c database.Chat, diffStatus *database.ChatDiffStatus, files []database.GetChatFileMetadataByChatIDRow) codersdk.Chat {
 	mcpServerIDs := c.MCPServerIDs
 	if mcpServerIDs == nil {
 		mcpServerIDs = []uuid.UUID{}
@@ -1572,6 +1608,19 @@ func Chat(c database.Chat, diffStatus *database.ChatDiffStatus) codersdk.Chat {
 		convertedDiffStatus := ChatDiffStatus(c.ID, diffStatus)
 		chat.DiffStatus = &convertedDiffStatus
 	}
+	if len(files) > 0 {
+		chat.Files = make([]codersdk.ChatFileMetadata, 0, len(files))
+		for _, row := range files {
+			chat.Files = append(chat.Files, codersdk.ChatFileMetadata{
+				ID:             row.ID,
+				OwnerID:        row.OwnerID,
+				OrganizationID: row.OrganizationID,
+				Name:           row.Name,
+				MimeType:       row.Mimetype,
+				CreatedAt:      row.CreatedAt,
+			})
+		}
+	}
 	if c.LastInjectedContext.Valid {
 		var parts []codersdk.ChatMessagePart
 		// Internal fields are stripped at write time in
@@ -1586,6 +1635,88 @@ func Chat(c database.Chat, diffStatus *database.ChatDiffStatus) codersdk.Chat {
 	return chat
 }
 
+func chatDebugAttempts(raw json.RawMessage) []map[string]any {
+	if len(raw) == 0 {
+		return nil
+	}
+
+	var attempts []map[string]any
+	if err := json.Unmarshal(raw, &attempts); err != nil {
+		return []map[string]any{{
+			"error": "malformed attempts payload",
+			"raw":   string(raw),
+		}}
+	}
+	return attempts
+}
+
+// rawJSONObject deserializes a JSON object payload for debug display.
+// If the payload is malformed, it returns a map with "error" and "raw"
+// keys preserving the original content for diagnostics.  Callers that
+// consume the result programmatically should check for the "error" key.
+func rawJSONObject(raw json.RawMessage) map[string]any {
+	if len(raw) == 0 {
+		return nil
+	}
+
+	var object map[string]any
+	if err := json.Unmarshal(raw, &object); err != nil {
+		return map[string]any{
+			"error": "malformed debug payload",
+			"raw":   string(raw),
+		}
+	}
+	return object
+}
+
+func nullRawJSONObject(raw pqtype.NullRawMessage) map[string]any {
+	if !raw.Valid {
+		return nil
+	}
+	return rawJSONObject(raw.RawMessage)
+}
+
+// ChatDebugRunSummary converts a database.ChatDebugRun to a
+// codersdk.ChatDebugRunSummary.
+func ChatDebugRunSummary(r database.ChatDebugRun) codersdk.ChatDebugRunSummary {
+	return codersdk.ChatDebugRunSummary{
+		ID:         r.ID,
+		ChatID:     r.ChatID,
+		Kind:       codersdk.ChatDebugRunKind(r.Kind),
+		Status:     codersdk.ChatDebugStatus(r.Status),
+		Provider:   nullStringPtr(r.Provider),
+		Model:      nullStringPtr(r.Model),
+		Summary:    rawJSONObject(r.Summary),
+		StartedAt:  r.StartedAt,
+		UpdatedAt:  r.UpdatedAt,
+		FinishedAt: nullTimePtr(r.FinishedAt),
+	}
+}
+
+// ChatDebugStep converts a database.ChatDebugStep to a
+// codersdk.ChatDebugStep.
+func ChatDebugStep(s database.ChatDebugStep) codersdk.ChatDebugStep {
+	return codersdk.ChatDebugStep{
+		ID:                  s.ID,
+		RunID:               s.RunID,
+		ChatID:              s.ChatID,
+		StepNumber:          s.StepNumber,
+		Operation:           codersdk.ChatDebugStepOperation(s.Operation),
+		Status:              codersdk.ChatDebugStatus(s.Status),
+		HistoryTipMessageID: nullInt64Ptr(s.HistoryTipMessageID),
+		AssistantMessageID:  nullInt64Ptr(s.AssistantMessageID),
+		NormalizedRequest:   rawJSONObject(s.NormalizedRequest),
+		NormalizedResponse:  nullRawJSONObject(s.NormalizedResponse),
+		Usage:               nullRawJSONObject(s.Usage),
+		Attempts:            chatDebugAttempts(s.Attempts),
+		Error:               nullRawJSONObject(s.Error),
+		Metadata:            rawJSONObject(s.Metadata),
+		StartedAt:           s.StartedAt,
+		UpdatedAt:           s.UpdatedAt,
+		FinishedAt:          nullTimePtr(s.FinishedAt),
+	}
+}
+
 // ChatRows converts a slice of database.GetChatsRow (which embeds
 // Chat plus HasUnread) to codersdk.Chat, looking up diff statuses
 // from the provided map. When diffStatusesByChatID is non-nil,
@@ -1595,9 +1726,9 @@ func ChatRows(rows []database.GetChatsRow, diffStatusesByChatID map[uuid.UUID]da
 	for i, row := range rows {
 		diffStatus, ok := diffStatusesByChatID[row.Chat.ID]
 		if ok {
-			result[i] = Chat(row.Chat, &diffStatus)
+			result[i] = Chat(row.Chat, &diffStatus, nil)
 		} else {
-			result[i] = Chat(row.Chat, nil)
+			result[i] = Chat(row.Chat, nil, nil)
 			if diffStatusesByChatID != nil {
 				emptyDiffStatus := ChatDiffStatus(row.Chat.ID, nil)
 				result[i].DiffStatus = &emptyDiffStatus
@@ -1690,3 +1821,41 @@ func ChatDiffStatus(chatID uuid.UUID, status *database.ChatDiffStatus) codersdk.
 
 	return result
 }
+
+// UserSecret converts a database ListUserSecretsRow (metadata only,
+// no value) to an SDK UserSecret.
+func UserSecret(secret database.ListUserSecretsRow) codersdk.UserSecret {
+	return codersdk.UserSecret{
+		ID:          secret.ID,
+		Name:        secret.Name,
+		Description: secret.Description,
+		EnvName:     secret.EnvName,
+		FilePath:    secret.FilePath,
+		CreatedAt:   secret.CreatedAt,
+		UpdatedAt:   secret.UpdatedAt,
+	}
+}
+
+// UserSecretFromFull converts a full database UserSecret row to an
+// SDK UserSecret, omitting the value and encryption key ID.
+func UserSecretFromFull(secret database.UserSecret) codersdk.UserSecret {
+	return codersdk.UserSecret{
+		ID:          secret.ID,
+		Name:        secret.Name,
+		Description: secret.Description,
+		EnvName:     secret.EnvName,
+		FilePath:    secret.FilePath,
+		CreatedAt:   secret.CreatedAt,
+		UpdatedAt:   secret.UpdatedAt,
+	}
+}
+
+// UserSecrets converts a slice of database ListUserSecretsRow to
+// SDK UserSecret values.
+func UserSecrets(secrets []database.ListUserSecretsRow) []codersdk.UserSecret {
+	result := make([]codersdk.UserSecret, 0, len(secrets))
+	for _, s := range secrets {
+		result = append(result, UserSecret(s))
+	}
+	return result
+}

coderd/database/db2sdk/db2sdk_test.go

@@ -210,6 +210,231 @@ func TestTemplateVersionParameter_BadDescription(t *testing.T) {
 	req.NotEmpty(sdk.DescriptionPlaintext, "broke the markdown parser with %v", desc)
 }
 
+func TestChatDebugRunSummary(t *testing.T) {
+	t.Parallel()
+
+	startedAt := time.Now().UTC().Round(time.Second)
+	finishedAt := startedAt.Add(5 * time.Second)
+
+	run := database.ChatDebugRun{
+		ID:         uuid.New(),
+		ChatID:     uuid.New(),
+		Kind:       "chat_turn",
+		Status:     "completed",
+		Provider:   sql.NullString{String: "openai", Valid: true},
+		Model:      sql.NullString{String: "gpt-4o", Valid: true},
+		Summary:    json.RawMessage(`{"step_count":3,"has_error":false}`),
+		StartedAt:  startedAt,
+		UpdatedAt:  finishedAt,
+		FinishedAt: sql.NullTime{Time: finishedAt, Valid: true},
+	}
+
+	sdk := db2sdk.ChatDebugRunSummary(run)
+
+	require.Equal(t, run.ID, sdk.ID)
+	require.Equal(t, run.ChatID, sdk.ChatID)
+	require.Equal(t, codersdk.ChatDebugRunKindChatTurn, sdk.Kind)
+	require.Equal(t, codersdk.ChatDebugStatusCompleted, sdk.Status)
+	require.NotNil(t, sdk.Provider)
+	require.Equal(t, "openai", *sdk.Provider)
+	require.NotNil(t, sdk.Model)
+	require.Equal(t, "gpt-4o", *sdk.Model)
+	require.Equal(t, map[string]any{"step_count": float64(3), "has_error": false}, sdk.Summary)
+	require.Equal(t, startedAt, sdk.StartedAt)
+	require.Equal(t, finishedAt, sdk.UpdatedAt)
+	require.NotNil(t, sdk.FinishedAt)
+	require.Equal(t, finishedAt, *sdk.FinishedAt)
+}
+
+func TestChatDebugRunSummary_NullableFieldsNil(t *testing.T) {
+	t.Parallel()
+
+	run := database.ChatDebugRun{
+		ID:        uuid.New(),
+		ChatID:    uuid.New(),
+		Kind:      "title_generation",
+		Status:    "in_progress",
+		Summary:   json.RawMessage(`{}`),
+		StartedAt: time.Now().UTC(),
+		UpdatedAt: time.Now().UTC(),
+	}
+
+	sdk := db2sdk.ChatDebugRunSummary(run)
+
+	require.Nil(t, sdk.Provider, "NULL Provider should map to nil")
+	require.Nil(t, sdk.Model, "NULL Model should map to nil")
+	require.Nil(t, sdk.FinishedAt, "NULL FinishedAt should map to nil")
+}
+
+func TestChatDebugStep(t *testing.T) {
+	t.Parallel()
+
+	startedAt := time.Now().UTC().Round(time.Second)
+	finishedAt := startedAt.Add(2 * time.Second)
+	attempts := json.RawMessage(`[
+		{
+			"attempt_number": 1,
+			"status": "completed",
+			"raw_request": {"url": "https://example.com"},
+			"raw_response": {"status": "200"},
+			"duration_ms": 123,
+			"started_at": "2026-03-01T10:00:01Z",
+			"finished_at": "2026-03-01T10:00:02Z"
+		}
+	]`)
+	step := database.ChatDebugStep{
+		ID:                uuid.New(),
+		RunID:             uuid.New(),
+		ChatID:            uuid.New(),
+		StepNumber:        1,
+		Operation:         "stream",
+		Status:            "completed",
+		NormalizedRequest: json.RawMessage(`{"messages":[]}`),
+		Attempts:          attempts,
+		Metadata:          json.RawMessage(`{"provider":"openai"}`),
+		StartedAt:         startedAt,
+		UpdatedAt:         finishedAt,
+		FinishedAt:        sql.NullTime{Time: finishedAt, Valid: true},
+	}
+
+	sdk := db2sdk.ChatDebugStep(step)
+
+	// Verify all scalar fields are mapped correctly.
+	require.Equal(t, step.ID, sdk.ID)
+	require.Equal(t, step.RunID, sdk.RunID)
+	require.Equal(t, step.ChatID, sdk.ChatID)
+	require.Equal(t, step.StepNumber, sdk.StepNumber)
+	require.Equal(t, codersdk.ChatDebugStepOperationStream, sdk.Operation)
+	require.Equal(t, codersdk.ChatDebugStatusCompleted, sdk.Status)
+	require.Equal(t, startedAt, sdk.StartedAt)
+	require.Equal(t, finishedAt, sdk.UpdatedAt)
+	require.Equal(t, &finishedAt, sdk.FinishedAt)
+
+	// Verify JSON object fields are deserialized.
+	require.NotNil(t, sdk.NormalizedRequest)
+	require.Equal(t, map[string]any{"messages": []any{}}, sdk.NormalizedRequest)
+	require.NotNil(t, sdk.Metadata)
+	require.Equal(t, map[string]any{"provider": "openai"}, sdk.Metadata)
+
+	// Verify nullable fields are nil when the DB row has NULL values.
+	require.Nil(t, sdk.HistoryTipMessageID, "NULL HistoryTipMessageID should map to nil")
+	require.Nil(t, sdk.AssistantMessageID, "NULL AssistantMessageID should map to nil")
+	require.Nil(t, sdk.NormalizedResponse, "NULL NormalizedResponse should map to nil")
+	require.Nil(t, sdk.Usage, "NULL Usage should map to nil")
+	require.Nil(t, sdk.Error, "NULL Error should map to nil")
+
+	// Verify attempts are preserved with all fields.
+	require.Len(t, sdk.Attempts, 1)
+	require.Equal(t, float64(1), sdk.Attempts[0]["attempt_number"])
+	require.Equal(t, "completed", sdk.Attempts[0]["status"])
+	require.Equal(t, float64(123), sdk.Attempts[0]["duration_ms"])
+	require.Equal(t, map[string]any{"url": "https://example.com"}, sdk.Attempts[0]["raw_request"])
+	require.Equal(t, map[string]any{"status": "200"}, sdk.Attempts[0]["raw_response"])
+}
+
+func TestChatDebugStep_NullableFieldsPopulated(t *testing.T) {
+	t.Parallel()
+
+	tipID := int64(42)
+	asstID := int64(99)
+	step := database.ChatDebugStep{
+		ID:                  uuid.New(),
+		RunID:               uuid.New(),
+		ChatID:              uuid.New(),
+		StepNumber:          2,
+		Operation:           "generate",
+		Status:              "completed",
+		HistoryTipMessageID: sql.NullInt64{Int64: tipID, Valid: true},
+		AssistantMessageID:  sql.NullInt64{Int64: asstID, Valid: true},
+		NormalizedRequest:   json.RawMessage(`{}`),
+		NormalizedResponse:  pqtype.NullRawMessage{RawMessage: json.RawMessage(`{"text":"hi"}`), Valid: true},
+		Usage:               pqtype.NullRawMessage{RawMessage: json.RawMessage(`{"tokens":10}`), Valid: true},
+		Error:               pqtype.NullRawMessage{RawMessage: json.RawMessage(`{"code":"rate_limit"}`), Valid: true},
+		Attempts:            json.RawMessage(`[]`),
+		Metadata:            json.RawMessage(`{}`),
+		StartedAt:           time.Now().UTC(),
+		UpdatedAt:           time.Now().UTC(),
+	}
+
+	sdk := db2sdk.ChatDebugStep(step)
+
+	require.NotNil(t, sdk.HistoryTipMessageID)
+	require.Equal(t, tipID, *sdk.HistoryTipMessageID)
+	require.NotNil(t, sdk.AssistantMessageID)
+	require.Equal(t, asstID, *sdk.AssistantMessageID)
+	require.NotNil(t, sdk.NormalizedResponse)
+	require.Equal(t, map[string]any{"text": "hi"}, sdk.NormalizedResponse)
+	require.NotNil(t, sdk.Usage)
+	require.Equal(t, map[string]any{"tokens": float64(10)}, sdk.Usage)
+	require.NotNil(t, sdk.Error)
+	require.Equal(t, map[string]any{"code": "rate_limit"}, sdk.Error)
+}
+
+func TestChatDebugStep_PreservesMalformedAttempts(t *testing.T) {
+	t.Parallel()
+
+	step := database.ChatDebugStep{
+		ID:                uuid.New(),
+		RunID:             uuid.New(),
+		ChatID:            uuid.New(),
+		StepNumber:        1,
+		Operation:         "stream",
+		Status:            "completed",
+		NormalizedRequest: json.RawMessage(`{"messages":[]}`),
+		Attempts:          json.RawMessage(`{"bad":true}`),
+		Metadata:          json.RawMessage(`{"provider":"openai"}`),
+		StartedAt:         time.Now().UTC(),
+		UpdatedAt:         time.Now().UTC(),
+	}
+
+	sdk := db2sdk.ChatDebugStep(step)
+	require.Len(t, sdk.Attempts, 1)
+	require.Equal(t, "malformed attempts payload", sdk.Attempts[0]["error"])
+	require.Equal(t, `{"bad":true}`, sdk.Attempts[0]["raw"])
+}
+
+func TestChatDebugRunSummary_PreservesMalformedSummary(t *testing.T) {
+	t.Parallel()
+
+	run := database.ChatDebugRun{
+		ID:        uuid.New(),
+		ChatID:    uuid.New(),
+		Kind:      "chat_turn",
+		Status:    "completed",
+		Summary:   json.RawMessage(`not-an-object`),
+		StartedAt: time.Now().UTC(),
+		UpdatedAt: time.Now().UTC(),
+	}
+
+	sdk := db2sdk.ChatDebugRunSummary(run)
+	require.Equal(t, "malformed debug payload", sdk.Summary["error"])
+	require.Equal(t, "not-an-object", sdk.Summary["raw"])
+}
+
+func TestChatDebugStep_PreservesMalformedRequest(t *testing.T) {
+	t.Parallel()
+
+	step := database.ChatDebugStep{
+		ID:                uuid.New(),
+		RunID:             uuid.New(),
+		ChatID:            uuid.New(),
+		StepNumber:        1,
+		Operation:         "stream",
+		Status:            "completed",
+		NormalizedRequest: json.RawMessage(`[1,2,3]`),
+		Attempts:          json.RawMessage(`[]`),
+		Metadata:          json.RawMessage(`"just-a-string"`),
+		StartedAt:         time.Now().UTC(),
+		UpdatedAt:         time.Now().UTC(),
+	}
+
+	sdk := db2sdk.ChatDebugStep(step)
+	require.Equal(t, "malformed debug payload", sdk.NormalizedRequest["error"])
+	require.Equal(t, "[1,2,3]", sdk.NormalizedRequest["raw"])
+	require.Equal(t, "malformed debug payload", sdk.Metadata["error"])
+	require.Equal(t, `"just-a-string"`, sdk.Metadata["raw"])
+}
+
 func TestAIBridgeInterception(t *testing.T) {
 	t.Parallel()
 
@@ -259,11 +484,13 @@ func TestAIBridgeInterception(t *testing.T) {
 			},
 			tokenUsages: []database.AIBridgeTokenUsage{
 				{
-					ID:                 uuid.New(),
-					InterceptionID:     interceptionID,
-					ProviderResponseID: "resp-123",
-					InputTokens:        100,
-					OutputTokens:       200,
+					ID:                    uuid.New(),
+					InterceptionID:        interceptionID,
+					ProviderResponseID:    "resp-123",
+					InputTokens:           100,
+					OutputTokens:          200,
+					CacheReadInputTokens:  50,
+					CacheWriteInputTokens: 10,
 					Metadata: pqtype.NullRawMessage{
 						RawMessage: json.RawMessage(`{"cache":"hit"}`),
 						Valid:      true,
@@ -413,6 +640,8 @@ func TestAIBridgeInterception(t *testing.T) {
 				require.Equal(t, tu.ProviderResponseID, result.TokenUsages[i].ProviderResponseID)
 				require.Equal(t, tu.InputTokens, result.TokenUsages[i].InputTokens)
 				require.Equal(t, tu.OutputTokens, result.TokenUsages[i].OutputTokens)
+				require.Equal(t, tu.CacheReadInputTokens, result.TokenUsages[i].CacheReadInputTokens)
+				require.Equal(t, tu.CacheWriteInputTokens, result.TokenUsages[i].CacheWriteInputTokens)
 			}
 
 			// Verify user prompts are converted correctly.
@@ -548,6 +777,10 @@ func TestChat_AllFieldsPopulated(t *testing.T) {
 			RawMessage: json.RawMessage(`[{"type":"context-file","context_file_path":"/AGENTS.md"}]`),
 			Valid:      true,
 		},
+		DynamicTools: pqtype.NullRawMessage{
+			RawMessage: json.RawMessage(`[{"name":"tool1","description":"test tool","inputSchema":{"type":"object"}}]`),
+			Valid:      true,
+		},
 	}
 	// Only ChatID is needed here. This test checks that
 	// Chat.DiffStatus is non-nil, not that every DiffStatus
@@ -557,14 +790,26 @@ func TestChat_AllFieldsPopulated(t *testing.T) {
 		ChatID: input.ID,
 	}
 
-	got := db2sdk.Chat(input, diffStatus)
+	fileRows := []database.GetChatFileMetadataByChatIDRow{
+		{
+			ID:             uuid.New(),
+			OwnerID:        input.OwnerID,
+			OrganizationID: uuid.New(),
+			Name:           "test.png",
+			Mimetype:       "image/png",
+			CreatedAt:      now,
+		},
+	}
+
+	got := db2sdk.Chat(input, diffStatus, fileRows)
 
 	v := reflect.ValueOf(got)
 	typ := v.Type()
 	// HasUnread is populated by ChatRows (which joins the
-	// read-cursor query), not by Chat, so it is expected
-	// to remain zero here.
-	skip := map[string]bool{"HasUnread": true}
+	// read-cursor query), not by Chat. Warnings is a transient
+	// field populated by handlers, not the converter. Both are
+	// expected to remain zero here.
+	skip := map[string]bool{"HasUnread": true, "Warnings": true}
 	for i := range typ.NumField() {
 		field := typ.Field(i)
 		if skip[field.Name] {
@@ -577,6 +822,112 @@ func TestChat_AllFieldsPopulated(t *testing.T) {
 	}
 }
 
+func TestChat_FileMetadataConversion(t *testing.T) {
+	t.Parallel()
+
+	ownerID := uuid.New()
+	orgID := uuid.New()
+	fileID := uuid.New()
+	now := dbtime.Now()
+
+	chat := database.Chat{
+		ID:                uuid.New(),
+		OwnerID:           ownerID,
+		LastModelConfigID: uuid.New(),
+		Title:             "file metadata test",
+		Status:            database.ChatStatusWaiting,
+		CreatedAt:         now,
+		UpdatedAt:         now,
+	}
+
+	rows := []database.GetChatFileMetadataByChatIDRow{
+		{
+			ID:             fileID,
+			OwnerID:        ownerID,
+			OrganizationID: orgID,
+			Name:           "screenshot.png",
+			Mimetype:       "image/png",
+			CreatedAt:      now,
+		},
+	}
+
+	result := db2sdk.Chat(chat, nil, rows)
+
+	require.Len(t, result.Files, 1)
+	f := result.Files[0]
+	require.Equal(t, fileID, f.ID)
+	require.Equal(t, ownerID, f.OwnerID, "OwnerID must be mapped from DB row")
+	require.Equal(t, orgID, f.OrganizationID, "OrganizationID must be mapped from DB row")
+	require.Equal(t, "screenshot.png", f.Name)
+	require.Equal(t, "image/png", f.MimeType)
+	require.Equal(t, now, f.CreatedAt)
+
+	// Verify JSON serialization uses snake_case for mime_type.
+	data, err := json.Marshal(f)
+	require.NoError(t, err)
+	require.Contains(t, string(data), `"mime_type"`)
+	require.NotContains(t, string(data), `"mimetype"`)
+}
+
+func TestChat_NilFilesOmitted(t *testing.T) {
+	t.Parallel()
+
+	chat := database.Chat{
+		ID:                uuid.New(),
+		OwnerID:           uuid.New(),
+		LastModelConfigID: uuid.New(),
+		Title:             "no files",
+		Status:            database.ChatStatusWaiting,
+		CreatedAt:         dbtime.Now(),
+		UpdatedAt:         dbtime.Now(),
+	}
+
+	result := db2sdk.Chat(chat, nil, nil)
+	require.Empty(t, result.Files)
+}
+
+func TestChat_MultipleFiles(t *testing.T) {
+	t.Parallel()
+
+	now := dbtime.Now()
+	file1 := uuid.New()
+	file2 := uuid.New()
+
+	chat := database.Chat{
+		ID:                uuid.New(),
+		OwnerID:           uuid.New(),
+		LastModelConfigID: uuid.New(),
+		Title:             "multi file test",
+		Status:            database.ChatStatusWaiting,
+		CreatedAt:         now,
+		UpdatedAt:         now,
+	}
+
+	rows := []database.GetChatFileMetadataByChatIDRow{
+		{
+			ID:             file1,
+			OwnerID:        chat.OwnerID,
+			OrganizationID: uuid.New(),
+			Name:           "a.png",
+			Mimetype:       "image/png",
+			CreatedAt:      now,
+		},
+		{
+			ID:             file2,
+			OwnerID:        chat.OwnerID,
+			OrganizationID: uuid.New(),
+			Name:           "b.txt",
+			Mimetype:       "text/plain",
+			CreatedAt:      now,
+		},
+	}
+
+	result := db2sdk.Chat(chat, nil, rows)
+	require.Len(t, result.Files, 2)
+	require.Equal(t, "a.png", result.Files[0].Name)
+	require.Equal(t, "b.txt", result.Files[1].Name)
+}
+
 func TestChatQueuedMessage_MalformedContent(t *testing.T) {
 	t.Parallel()
 

coderd/database/dbauthz/dbauthz.go

@@ -1627,6 +1627,13 @@ func (q *querier) BatchUpdateWorkspaceNextStartAt(ctx context.Context, arg datab
 	return q.db.BatchUpdateWorkspaceNextStartAt(ctx, arg)
 }
 
+func (q *querier) BatchUpsertConnectionLogs(ctx context.Context, arg database.BatchUpsertConnectionLogsParams) error {
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceConnectionLog); err != nil {
+		return err
+	}
+	return q.db.BatchUpsertConnectionLogs(ctx, arg)
+}
+
 func (q *querier) BulkMarkNotificationMessagesFailed(ctx context.Context, arg database.BulkMarkNotificationMessagesFailedParams) (int64, error) {
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceNotificationMessage); err != nil {
 		return 0, err
@@ -1694,13 +1701,6 @@ func (q *querier) CleanTailnetTunnels(ctx context.Context) error {
 	return q.db.CleanTailnetTunnels(ctx)
 }
 
-func (q *querier) CleanupDeletedMCPServerIDsFromChatAutomations(ctx context.Context) error {
-	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceChatAutomation); err != nil {
-		return err
-	}
-	return q.db.CleanupDeletedMCPServerIDsFromChatAutomations(ctx)
-}
-
 func (q *querier) CleanupDeletedMCPServerIDsFromChats(ctx context.Context) error {
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceChat); err != nil {
 		return err
@@ -1708,6 +1708,17 @@ func (q *querier) CleanupDeletedMCPServerIDsFromChats(ctx context.Context) error
 	return q.db.CleanupDeletedMCPServerIDsFromChats(ctx)
 }
 
+func (q *querier) ClearChatMessageProviderResponseIDsByChatID(ctx context.Context, chatID uuid.UUID) error {
+	chat, err := q.db.GetChatByID(ctx, chatID)
+	if err != nil {
+		return err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
+		return err
+	}
+	return q.db.ClearChatMessageProviderResponseIDsByChatID(ctx, chatID)
+}
+
 func (q *querier) CountAIBridgeInterceptions(ctx context.Context, arg database.CountAIBridgeInterceptionsParams) (int64, error) {
 	prep, err := prepareSQLFilter(ctx, q.auth, policy.ActionRead, rbac.ResourceAibridgeInterception.Type)
 	if err != nil {
@@ -1738,28 +1749,6 @@ func (q *querier) CountAuditLogs(ctx context.Context, arg database.CountAuditLog
 	return q.db.CountAuthorizedAuditLogs(ctx, arg, prep)
 }
 
-func (q *querier) CountChatAutomationChatCreatesInWindow(ctx context.Context, arg database.CountChatAutomationChatCreatesInWindowParams) (int64, error) {
-	automation, err := q.db.GetChatAutomationByID(ctx, arg.AutomationID)
-	if err != nil {
-		return 0, err
-	}
-	if err := q.authorizeContext(ctx, policy.ActionRead, automation); err != nil {
-		return 0, err
-	}
-	return q.db.CountChatAutomationChatCreatesInWindow(ctx, arg)
-}
-
-func (q *querier) CountChatAutomationMessagesInWindow(ctx context.Context, arg database.CountChatAutomationMessagesInWindowParams) (int64, error) {
-	automation, err := q.db.GetChatAutomationByID(ctx, arg.AutomationID)
-	if err != nil {
-		return 0, err
-	}
-	if err := q.authorizeContext(ctx, policy.ActionRead, automation); err != nil {
-		return 0, err
-	}
-	return q.db.CountChatAutomationMessagesInWindow(ctx, arg)
-}
-
 func (q *querier) CountConnectionLogs(ctx context.Context, arg database.CountConnectionLogsParams) (int64, error) {
 	// Just like the actual query, shortcut if the user is an owner.
 	err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceConnectionLog)
@@ -1871,26 +1860,26 @@ func (q *querier) DeleteApplicationConnectAPIKeysByUserID(ctx context.Context, u
 	return q.db.DeleteApplicationConnectAPIKeysByUserID(ctx, userID)
 }
 
-func (q *querier) DeleteChatAutomationByID(ctx context.Context, id uuid.UUID) error {
-	return deleteQ(q.log, q.auth, q.db.GetChatAutomationByID, q.db.DeleteChatAutomationByID)(ctx, id)
+func (q *querier) DeleteChatDebugDataAfterMessageID(ctx context.Context, arg database.DeleteChatDebugDataAfterMessageIDParams) (int64, error) {
+	chat, err := q.db.GetChatByID(ctx, arg.ChatID)
+	if err != nil {
+		return 0, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
+		return 0, err
+	}
+	return q.db.DeleteChatDebugDataAfterMessageID(ctx, arg)
 }
 
-// Triggers are sub-resources of an automation. Deleting a trigger
-// is a configuration change, so we authorize ActionUpdate on the
-// parent rather than ActionDelete.
-func (q *querier) DeleteChatAutomationTriggerByID(ctx context.Context, id uuid.UUID) error {
-	trigger, err := q.db.GetChatAutomationTriggerByID(ctx, id)
+func (q *querier) DeleteChatDebugDataByChatID(ctx context.Context, chatID uuid.UUID) (int64, error) {
+	chat, err := q.db.GetChatByID(ctx, chatID)
 	if err != nil {
-		return err
+		return 0, err
 	}
-	automation, err := q.db.GetChatAutomationByID(ctx, trigger.AutomationID)
-	if err != nil {
-		return err
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
+		return 0, err
 	}
-	if err := q.authorizeContext(ctx, policy.ActionUpdate, automation); err != nil {
-		return err
-	}
-	return q.db.DeleteChatAutomationTriggerByID(ctx, id)
+	return q.db.DeleteChatDebugDataByChatID(ctx, chatID)
 }
 
 func (q *querier) DeleteChatModelConfigByID(ctx context.Context, id uuid.UUID) error {
@@ -2075,6 +2064,20 @@ func (q *querier) DeleteOldAuditLogs(ctx context.Context, arg database.DeleteOld
 	return q.db.DeleteOldAuditLogs(ctx, arg)
 }
 
+func (q *querier) DeleteOldChatFiles(ctx context.Context, arg database.DeleteOldChatFilesParams) (int64, error) {
+	if err := q.authorizeContext(ctx, policy.ActionDelete, rbac.ResourceSystem); err != nil {
+		return 0, err
+	}
+	return q.db.DeleteOldChatFiles(ctx, arg)
+}
+
+func (q *querier) DeleteOldChats(ctx context.Context, arg database.DeleteOldChatsParams) (int64, error) {
+	if err := q.authorizeContext(ctx, policy.ActionDelete, rbac.ResourceSystem); err != nil {
+		return 0, err
+	}
+	return q.db.DeleteOldChats(ctx, arg)
+}
+
 func (q *querier) DeleteOldConnectionLogs(ctx context.Context, arg database.DeleteOldConnectionLogsParams) (int64, error) {
 	if err := q.authorizeContext(ctx, policy.ActionDelete, rbac.ResourceSystem); err != nil {
 		return 0, err
@@ -2188,17 +2191,23 @@ func (q *querier) DeleteUserChatCompactionThreshold(ctx context.Context, arg dat
 	return q.db.DeleteUserChatCompactionThreshold(ctx, arg)
 }
 
-func (q *querier) DeleteUserSecret(ctx context.Context, id uuid.UUID) error {
-	// First get the secret to check ownership
-	secret, err := q.GetUserSecret(ctx, id)
+func (q *querier) DeleteUserChatProviderKey(ctx context.Context, arg database.DeleteUserChatProviderKeyParams) error {
+	u, err := q.db.GetUserByID(ctx, arg.UserID)
 	if err != nil {
 		return err
 	}
-
-	if err := q.authorizeContext(ctx, policy.ActionDelete, secret); err != nil {
+	if err := q.authorizeContext(ctx, policy.ActionUpdatePersonal, u); err != nil {
 		return err
 	}
-	return q.db.DeleteUserSecret(ctx, id)
+	return q.db.DeleteUserChatProviderKey(ctx, arg)
+}
+
+func (q *querier) DeleteUserSecretByUserIDAndName(ctx context.Context, arg database.DeleteUserSecretByUserIDAndNameParams) (int64, error) {
+	obj := rbac.ResourceUserSecret.WithOwner(arg.UserID.String())
+	if err := q.authorizeContext(ctx, policy.ActionDelete, obj); err != nil {
+		return 0, err
+	}
+	return q.db.DeleteUserSecretByUserIDAndName(ctx, arg)
 }
 
 func (q *querier) DeleteWebpushSubscriptionByUserIDAndEndpoint(ctx context.Context, arg database.DeleteWebpushSubscriptionByUserIDAndEndpointParams) error {
@@ -2360,6 +2369,14 @@ func (q *querier) FetchVolumesResourceMonitorsUpdatedAfter(ctx context.Context,
 	return q.db.FetchVolumesResourceMonitorsUpdatedAfter(ctx, updatedAt)
 }
 
+func (q *querier) FinalizeStaleChatDebugRows(ctx context.Context, updatedBefore time.Time) (database.FinalizeStaleChatDebugRowsRow, error) {
+	// Background sweep operates across all chats.
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceChat); err != nil {
+		return database.FinalizeStaleChatDebugRowsRow{}, err
+	}
+	return q.db.FinalizeStaleChatDebugRows(ctx, updatedBefore)
+}
+
 func (q *querier) FindMatchingPresetID(ctx context.Context, arg database.FindMatchingPresetIDParams) (uuid.UUID, error) {
 	_, err := q.GetTemplateVersionByID(ctx, arg.TemplateVersionID)
 	if err != nil {
@@ -2437,14 +2454,8 @@ func (q *querier) GetActiveAISeatCount(ctx context.Context) (int64, error) {
 	return q.db.GetActiveAISeatCount(ctx)
 }
 
-// GetActiveChatAutomationCronTriggers is a system-level query used by
-// the cron scheduler. It requires read permission on all automations
-// (admin gate) because it fetches triggers across all orgs and owners.
-func (q *querier) GetActiveChatAutomationCronTriggers(ctx context.Context) ([]database.GetActiveChatAutomationCronTriggersRow, error) {
-	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceChatAutomation.All()); err != nil {
-		return nil, err
-	}
-	return q.db.GetActiveChatAutomationCronTriggers(ctx)
+func (q *querier) GetActiveChatsByAgentID(ctx context.Context, agentID uuid.UUID) ([]database.Chat, error) {
+	return fetchWithPostFilter(q.auth, policy.ActionRead, q.db.GetActiveChatsByAgentID)(ctx, agentID)
 }
 
 func (q *querier) GetActivePresetPrebuildSchedules(ctx context.Context) ([]database.TemplateVersionPresetPrebuildSchedule, error) {
@@ -2538,64 +2549,6 @@ func (q *querier) GetAuthorizationUserRoles(ctx context.Context, userID uuid.UUI
 	return q.db.GetAuthorizationUserRoles(ctx, userID)
 }
 
-func (q *querier) GetChatAutomationByID(ctx context.Context, id uuid.UUID) (database.ChatAutomation, error) {
-	return fetch(q.log, q.auth, q.db.GetChatAutomationByID)(ctx, id)
-}
-
-func (q *querier) GetChatAutomationEventsByAutomationID(ctx context.Context, arg database.GetChatAutomationEventsByAutomationIDParams) ([]database.ChatAutomationEvent, error) {
-	automation, err := q.db.GetChatAutomationByID(ctx, arg.AutomationID)
-	if err != nil {
-		return nil, err
-	}
-	if err := q.authorizeContext(ctx, policy.ActionRead, automation); err != nil {
-		return nil, err
-	}
-	return q.db.GetChatAutomationEventsByAutomationID(ctx, arg)
-}
-
-func (q *querier) GetChatAutomationTriggerByID(ctx context.Context, id uuid.UUID) (database.ChatAutomationTrigger, error) {
-	trigger, err := q.db.GetChatAutomationTriggerByID(ctx, id)
-	if err != nil {
-		return database.ChatAutomationTrigger{}, err
-	}
-	automation, err := q.db.GetChatAutomationByID(ctx, trigger.AutomationID)
-	if err != nil {
-		return database.ChatAutomationTrigger{}, err
-	}
-	if err := q.authorizeContext(ctx, policy.ActionRead, automation); err != nil {
-		return database.ChatAutomationTrigger{}, err
-	}
-	return trigger, nil
-}
-
-func (q *querier) GetChatAutomationTriggersByAutomationID(ctx context.Context, automationID uuid.UUID) ([]database.ChatAutomationTrigger, error) {
-	automation, err := q.db.GetChatAutomationByID(ctx, automationID)
-	if err != nil {
-		return nil, err
-	}
-	if err := q.authorizeContext(ctx, policy.ActionRead, automation); err != nil {
-		return nil, err
-	}
-	return q.db.GetChatAutomationTriggersByAutomationID(ctx, automationID)
-}
-
-func (q *querier) GetChatAutomations(ctx context.Context, arg database.GetChatAutomationsParams) ([]database.ChatAutomation, error) {
-	// Shortcut if the caller has broad read access (e.g. site admins
-	// / owners). The SQL filter is noticeable, so skip it when we
-	// can.
-	err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceChatAutomation.All())
-	if err == nil {
-		return q.db.GetChatAutomations(ctx, arg)
-	}
-
-	// Fall back to SQL-level row filtering for normal users.
-	prep, err := prepareSQLFilter(ctx, q.auth, policy.ActionRead, rbac.ResourceChatAutomation.Type)
-	if err != nil {
-		return nil, xerrors.Errorf("prepare chat automation SQL filter: %w", err)
-	}
-	return q.db.GetAuthorizedChatAutomations(ctx, arg, prep)
-}
-
 func (q *querier) GetChatByID(ctx context.Context, id uuid.UUID) (database.Chat, error) {
 	return fetch(q.log, q.auth, q.db.GetChatByID)(ctx, id)
 }
@@ -2632,6 +2585,59 @@ func (q *querier) GetChatCostSummary(ctx context.Context, arg database.GetChatCo
 	return q.db.GetChatCostSummary(ctx, arg)
 }
 
+func (q *querier) GetChatDebugLoggingAllowUsers(ctx context.Context) (bool, error) {
+	// The allow-users flag is a deployment-wide setting read by any
+	// authenticated chat user. We only require that an explicit actor
+	// is present in the context so unauthenticated calls fail closed.
+	if _, ok := ActorFromContext(ctx); !ok {
+		return false, ErrNoActor
+	}
+	return q.db.GetChatDebugLoggingAllowUsers(ctx)
+}
+
+func (q *querier) GetChatDebugRunByID(ctx context.Context, id uuid.UUID) (database.ChatDebugRun, error) {
+	run, err := q.db.GetChatDebugRunByID(ctx, id)
+	if err != nil {
+		return database.ChatDebugRun{}, err
+	}
+	// Authorize via the owning chat.
+	chat, err := q.db.GetChatByID(ctx, run.ChatID)
+	if err != nil {
+		return database.ChatDebugRun{}, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionRead, chat); err != nil {
+		return database.ChatDebugRun{}, err
+	}
+	return run, nil
+}
+
+func (q *querier) GetChatDebugRunsByChatID(ctx context.Context, arg database.GetChatDebugRunsByChatIDParams) ([]database.ChatDebugRun, error) {
+	chat, err := q.db.GetChatByID(ctx, arg.ChatID)
+	if err != nil {
+		return nil, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionRead, chat); err != nil {
+		return nil, err
+	}
+	return q.db.GetChatDebugRunsByChatID(ctx, arg)
+}
+
+func (q *querier) GetChatDebugStepsByRunID(ctx context.Context, runID uuid.UUID) ([]database.ChatDebugStep, error) {
+	run, err := q.db.GetChatDebugRunByID(ctx, runID)
+	if err != nil {
+		return nil, err
+	}
+	// Authorize via the owning chat.
+	chat, err := q.db.GetChatByID(ctx, run.ChatID)
+	if err != nil {
+		return nil, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionRead, chat); err != nil {
+		return nil, err
+	}
+	return q.db.GetChatDebugStepsByRunID(ctx, runID)
+}
+
 func (q *querier) GetChatDesktopEnabled(ctx context.Context) (bool, error) {
 	// The desktop-enabled flag is a deployment-wide setting read by any
 	// authenticated chat user and by chatd when deciding whether to expose
@@ -2684,6 +2690,10 @@ func (q *querier) GetChatFileByID(ctx context.Context, id uuid.UUID) (database.C
 	return file, nil
 }
 
+func (q *querier) GetChatFileMetadataByChatID(ctx context.Context, chatID uuid.UUID) ([]database.GetChatFileMetadataByChatIDRow, error) {
+	return fetchWithPostFilter(q.auth, policy.ActionRead, q.db.GetChatFileMetadataByChatID)(ctx, chatID)
+}
+
 func (q *querier) GetChatFilesByIDs(ctx context.Context, ids []uuid.UUID) ([]database.ChatFile, error) {
 	files, err := q.db.GetChatFilesByIDs(ctx, ids)
 	if err != nil {
@@ -2724,6 +2734,14 @@ func (q *querier) GetChatMessageByID(ctx context.Context, id int64) (database.Ch
 	return msg, nil
 }
 
+func (q *querier) GetChatMessageSummariesPerChat(ctx context.Context, createdAfter time.Time) ([]database.GetChatMessageSummariesPerChatRow, error) {
+	// Telemetry queries are called from system contexts only.
+	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceSystem); err != nil {
+		return nil, err
+	}
+	return q.db.GetChatMessageSummariesPerChat(ctx, createdAfter)
+}
+
 func (q *querier) GetChatMessagesByChatID(ctx context.Context, arg database.GetChatMessagesByChatIDParams) ([]database.ChatMessage, error) {
 	// Authorize read on the parent chat.
 	_, err := q.GetChatByID(ctx, arg.ChatID)
@@ -2772,6 +2790,14 @@ func (q *querier) GetChatModelConfigs(ctx context.Context) ([]database.ChatModel
 	return q.db.GetChatModelConfigs(ctx)
 }
 
+func (q *querier) GetChatModelConfigsForTelemetry(ctx context.Context) ([]database.GetChatModelConfigsForTelemetryRow, error) {
+	// Telemetry queries are called from system contexts only.
+	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceSystem); err != nil {
+		return nil, err
+	}
+	return q.db.GetChatModelConfigsForTelemetry(ctx)
+}
+
 func (q *querier) GetChatProviderByID(ctx context.Context, id uuid.UUID) (database.ChatProvider, error) {
 	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceDeploymentConfig); err != nil {
 		return database.ChatProvider{}, err
@@ -2801,6 +2827,15 @@ func (q *querier) GetChatQueuedMessages(ctx context.Context, chatID uuid.UUID) (
 	return q.db.GetChatQueuedMessages(ctx, chatID)
 }
 
+func (q *querier) GetChatRetentionDays(ctx context.Context) (int32, error) {
+	// Chat retention is a deployment-wide config read by dbpurge.
+	// Only requires a valid actor in context.
+	if _, ok := ActorFromContext(ctx); !ok {
+		return 0, ErrNoActor
+	}
+	return q.db.GetChatRetentionDays(ctx)
+}
+
 func (q *querier) GetChatSystemPrompt(ctx context.Context) (string, error) {
 	// The system prompt is a deployment-wide setting read during chat
 	// creation by every authenticated user, so no RBAC policy check
@@ -2879,6 +2914,14 @@ func (q *querier) GetChatsByWorkspaceIDs(ctx context.Context, ids []uuid.UUID) (
 	return fetchWithPostFilter(q.auth, policy.ActionRead, q.db.GetChatsByWorkspaceIDs)(ctx, ids)
 }
 
+func (q *querier) GetChatsUpdatedAfter(ctx context.Context, updatedAfter time.Time) ([]database.GetChatsUpdatedAfterRow, error) {
+	// Telemetry queries are called from system contexts only.
+	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceSystem); err != nil {
+		return nil, err
+	}
+	return q.db.GetChatsUpdatedAfter(ctx, updatedAfter)
+}
+
 func (q *querier) GetConnectionLogsOffset(ctx context.Context, arg database.GetConnectionLogsOffsetParams) ([]database.GetConnectionLogsOffsetRow, error) {
 	// Just like with the audit logs query, shortcut if the user is an owner.
 	err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceConnectionLog)
@@ -3441,11 +3484,11 @@ func (q *querier) GetPRInsightsPerModel(ctx context.Context, arg database.GetPRI
 	return q.db.GetPRInsightsPerModel(ctx, arg)
 }
 
-func (q *querier) GetPRInsightsRecentPRs(ctx context.Context, arg database.GetPRInsightsRecentPRsParams) ([]database.GetPRInsightsRecentPRsRow, error) {
+func (q *querier) GetPRInsightsPullRequests(ctx context.Context, arg database.GetPRInsightsPullRequestsParams) ([]database.GetPRInsightsPullRequestsRow, error) {
 	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceDeploymentConfig); err != nil {
 		return nil, err
 	}
-	return q.db.GetPRInsightsRecentPRs(ctx, arg)
+	return q.db.GetPRInsightsPullRequests(ctx, arg)
 }
 
 func (q *querier) GetPRInsightsSummary(ctx context.Context, arg database.GetPRInsightsSummaryParams) (database.GetPRInsightsSummaryRow, error) {
@@ -3754,18 +3797,18 @@ func (q *querier) GetTailnetPeers(ctx context.Context, id uuid.UUID) ([]database
 	return q.db.GetTailnetPeers(ctx, id)
 }
 
-func (q *querier) GetTailnetTunnelPeerBindings(ctx context.Context, srcID uuid.UUID) ([]database.GetTailnetTunnelPeerBindingsRow, error) {
+func (q *querier) GetTailnetTunnelPeerBindingsBatch(ctx context.Context, ids []uuid.UUID) ([]database.GetTailnetTunnelPeerBindingsBatchRow, error) {
 	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceTailnetCoordinator); err != nil {
 		return nil, err
 	}
-	return q.db.GetTailnetTunnelPeerBindings(ctx, srcID)
+	return q.db.GetTailnetTunnelPeerBindingsBatch(ctx, ids)
 }
 
-func (q *querier) GetTailnetTunnelPeerIDs(ctx context.Context, srcID uuid.UUID) ([]database.GetTailnetTunnelPeerIDsRow, error) {
+func (q *querier) GetTailnetTunnelPeerIDsBatch(ctx context.Context, ids []uuid.UUID) ([]database.GetTailnetTunnelPeerIDsBatchRow, error) {
 	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceTailnetCoordinator); err != nil {
 		return nil, err
 	}
-	return q.db.GetTailnetTunnelPeerIDs(ctx, srcID)
+	return q.db.GetTailnetTunnelPeerIDsBatch(ctx, ids)
 }
 
 func (q *querier) GetTaskByID(ctx context.Context, id uuid.UUID) (database.Task, error) {
@@ -4143,6 +4186,28 @@ func (q *querier) GetUserChatCustomPrompt(ctx context.Context, userID uuid.UUID)
 	return q.db.GetUserChatCustomPrompt(ctx, userID)
 }
 
+func (q *querier) GetUserChatDebugLoggingEnabled(ctx context.Context, userID uuid.UUID) (bool, error) {
+	u, err := q.db.GetUserByID(ctx, userID)
+	if err != nil {
+		return false, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionReadPersonal, u); err != nil {
+		return false, err
+	}
+	return q.db.GetUserChatDebugLoggingEnabled(ctx, userID)
+}
+
+func (q *querier) GetUserChatProviderKeys(ctx context.Context, userID uuid.UUID) ([]database.UserChatProviderKey, error) {
+	u, err := q.db.GetUserByID(ctx, userID)
+	if err != nil {
+		return nil, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionReadPersonal, u); err != nil {
+		return nil, err
+	}
+	return q.db.GetUserChatProviderKeys(ctx, userID)
+}
+
 func (q *querier) GetUserChatSpendInPeriod(ctx context.Context, arg database.GetUserChatSpendInPeriodParams) (int64, error) {
 	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceChat.WithOwner(arg.UserID.String())); err != nil {
 		return 0, err
@@ -4214,19 +4279,6 @@ func (q *querier) GetUserNotificationPreferences(ctx context.Context, userID uui
 	return q.db.GetUserNotificationPreferences(ctx, userID)
 }
 
-func (q *querier) GetUserSecret(ctx context.Context, id uuid.UUID) (database.UserSecret, error) {
-	// First get the secret to check ownership
-	secret, err := q.db.GetUserSecret(ctx, id)
-	if err != nil {
-		return database.UserSecret{}, err
-	}
-
-	if err := q.authorizeContext(ctx, policy.ActionRead, secret); err != nil {
-		return database.UserSecret{}, err
-	}
-	return secret, nil
-}
-
 func (q *querier) GetUserSecretByUserIDAndName(ctx context.Context, arg database.GetUserSecretByUserIDAndNameParams) (database.UserSecret, error) {
 	obj := rbac.ResourceUserSecret.WithOwner(arg.UserID.String())
 	if err := q.authorizeContext(ctx, policy.ActionRead, obj); err != nil {
@@ -4891,34 +4943,31 @@ func (q *querier) InsertChat(ctx context.Context, arg database.InsertChatParams)
 	return insert(q.log, q.auth, rbac.ResourceChat.WithOwner(arg.OwnerID.String()), q.db.InsertChat)(ctx, arg)
 }
 
-func (q *querier) InsertChatAutomation(ctx context.Context, arg database.InsertChatAutomationParams) (database.ChatAutomation, error) {
-	return insert(q.log, q.auth, rbac.ResourceChatAutomation.WithOwner(arg.OwnerID.String()).InOrg(arg.OrganizationID), q.db.InsertChatAutomation)(ctx, arg)
+func (q *querier) InsertChatDebugRun(ctx context.Context, arg database.InsertChatDebugRunParams) (database.ChatDebugRun, error) {
+	chat, err := q.db.GetChatByID(ctx, arg.ChatID)
+	if err != nil {
+		return database.ChatDebugRun{}, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
+		return database.ChatDebugRun{}, err
+	}
+	return q.db.InsertChatDebugRun(ctx, arg)
 }
 
-// Events are append-only records produced by the system when
-// triggers fire. We authorize ActionUpdate on the parent
-// automation because inserting an event is a side-effect of
-// processing the automation, not an independent create action.
-func (q *querier) InsertChatAutomationEvent(ctx context.Context, arg database.InsertChatAutomationEventParams) (database.ChatAutomationEvent, error) {
-	automation, err := q.db.GetChatAutomationByID(ctx, arg.AutomationID)
+// InsertChatDebugStep creates a new step in a debug run.  The underlying
+// SQL uses INSERT ... SELECT ... FROM chat_debug_runs to enforce that the
+// run exists and belongs to the specified chat.  If the run_id is invalid
+// or the chat_id doesn't match, the INSERT produces 0 rows and SQLC
+// returns sql.ErrNoRows.
+func (q *querier) InsertChatDebugStep(ctx context.Context, arg database.InsertChatDebugStepParams) (database.ChatDebugStep, error) {
+	chat, err := q.db.GetChatByID(ctx, arg.ChatID)
 	if err != nil {
-		return database.ChatAutomationEvent{}, err
+		return database.ChatDebugStep{}, err
 	}
-	if err := q.authorizeContext(ctx, policy.ActionUpdate, automation); err != nil {
-		return database.ChatAutomationEvent{}, err
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
+		return database.ChatDebugStep{}, err
 	}
-	return q.db.InsertChatAutomationEvent(ctx, arg)
-}
-
-func (q *querier) InsertChatAutomationTrigger(ctx context.Context, arg database.InsertChatAutomationTriggerParams) (database.ChatAutomationTrigger, error) {
-	automation, err := q.db.GetChatAutomationByID(ctx, arg.AutomationID)
-	if err != nil {
-		return database.ChatAutomationTrigger{}, err
-	}
-	if err := q.authorizeContext(ctx, policy.ActionUpdate, automation); err != nil {
-		return database.ChatAutomationTrigger{}, err
-	}
-	return q.db.InsertChatAutomationTrigger(ctx, arg)
+	return q.db.InsertChatDebugStep(ctx, arg)
 }
 
 func (q *querier) InsertChatFile(ctx context.Context, arg database.InsertChatFileParams) (database.InsertChatFileRow, error) {
@@ -5513,6 +5562,17 @@ func (q *querier) InsertWorkspaceResourceMetadata(ctx context.Context, arg datab
 	return q.db.InsertWorkspaceResourceMetadata(ctx, arg)
 }
 
+func (q *querier) LinkChatFiles(ctx context.Context, arg database.LinkChatFilesParams) (int32, error) {
+	chat, err := q.db.GetChatByID(ctx, arg.ChatID)
+	if err != nil {
+		return 0, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
+		return 0, err
+	}
+	return q.db.LinkChatFiles(ctx, arg)
+}
+
 func (q *querier) ListAIBridgeClients(ctx context.Context, arg database.ListAIBridgeClientsParams) ([]string, error) {
 	prep, err := prepareSQLFilter(ctx, q.auth, policy.ActionRead, rbac.ResourceAibridgeInterception.Type)
 	if err != nil {
@@ -5629,7 +5689,7 @@ func (q *querier) ListUserChatCompactionThresholds(ctx context.Context, userID u
 	return q.db.ListUserChatCompactionThresholds(ctx, userID)
 }
 
-func (q *querier) ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]database.UserSecret, error) {
+func (q *querier) ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]database.ListUserSecretsRow, error) {
 	obj := rbac.ResourceUserSecret.WithOwner(userID.String())
 	if err := q.authorizeContext(ctx, policy.ActionRead, obj); err != nil {
 		return nil, err
@@ -5637,6 +5697,16 @@ func (q *querier) ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]data
 	return q.db.ListUserSecrets(ctx, userID)
 }
 
+func (q *querier) ListUserSecretsWithValues(ctx context.Context, userID uuid.UUID) ([]database.UserSecret, error) {
+	// This query returns decrypted secret values and must only be called
+	// from system contexts (provisioner, agent manifest). REST API
+	// handlers should use ListUserSecrets (metadata only).
+	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceSystem); err != nil {
+		return nil, err
+	}
+	return q.db.ListUserSecretsWithValues(ctx, userID)
+}
+
 func (q *querier) ListWorkspaceAgentPortShares(ctx context.Context, workspaceID uuid.UUID) ([]database.WorkspaceAgentPortShare, error) {
 	workspace, err := q.db.GetWorkspaceByID(ctx, workspaceID)
 	if err != nil {
@@ -5718,13 +5788,6 @@ func (q *querier) PopNextQueuedMessage(ctx context.Context, chatID uuid.UUID) (d
 	return q.db.PopNextQueuedMessage(ctx, chatID)
 }
 
-func (q *querier) PurgeOldChatAutomationEvents(ctx context.Context, arg database.PurgeOldChatAutomationEventsParams) (int64, error) {
-	if err := q.authorizeContext(ctx, policy.ActionDelete, rbac.ResourceChatAutomation.All()); err != nil {
-		return 0, err
-	}
-	return q.db.PurgeOldChatAutomationEvents(ctx, arg)
-}
-
 func (q *querier) ReduceWorkspaceAgentShareLevelToAuthenticatedByTemplate(ctx context.Context, templateID uuid.UUID) error {
 	template, err := q.db.GetTemplateByID(ctx, templateID)
 	if err != nil {
@@ -5801,6 +5864,17 @@ func (q *querier) SoftDeleteChatMessagesAfterID(ctx context.Context, arg databas
 	return q.db.SoftDeleteChatMessagesAfterID(ctx, arg)
 }
 
+func (q *querier) SoftDeleteContextFileMessages(ctx context.Context, chatID uuid.UUID) error {
+	chat, err := q.db.GetChatByID(ctx, chatID)
+	if err != nil {
+		return err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
+		return err
+	}
+	return q.db.SoftDeleteContextFileMessages(ctx, chatID)
+}
+
 func (q *querier) TryAcquireLock(ctx context.Context, id int64) (bool, error) {
 	return q.db.TryAcquireLock(ctx, id)
 }
@@ -5871,58 +5945,6 @@ func (q *querier) UpdateAPIKeyByID(ctx context.Context, arg database.UpdateAPIKe
 	return update(q.log, q.auth, fetch, q.db.UpdateAPIKeyByID)(ctx, arg)
 }
 
-func (q *querier) UpdateChatAutomation(ctx context.Context, arg database.UpdateChatAutomationParams) (database.ChatAutomation, error) {
-	fetchFunc := func(ctx context.Context, arg database.UpdateChatAutomationParams) (database.ChatAutomation, error) {
-		return q.db.GetChatAutomationByID(ctx, arg.ID)
-	}
-	return updateWithReturn(q.log, q.auth, fetchFunc, q.db.UpdateChatAutomation)(ctx, arg)
-}
-
-func (q *querier) UpdateChatAutomationTrigger(ctx context.Context, arg database.UpdateChatAutomationTriggerParams) (database.ChatAutomationTrigger, error) {
-	trigger, err := q.db.GetChatAutomationTriggerByID(ctx, arg.ID)
-	if err != nil {
-		return database.ChatAutomationTrigger{}, err
-	}
-	automation, err := q.db.GetChatAutomationByID(ctx, trigger.AutomationID)
-	if err != nil {
-		return database.ChatAutomationTrigger{}, err
-	}
-	if err := q.authorizeContext(ctx, policy.ActionUpdate, automation); err != nil {
-		return database.ChatAutomationTrigger{}, err
-	}
-	return q.db.UpdateChatAutomationTrigger(ctx, arg)
-}
-
-func (q *querier) UpdateChatAutomationTriggerLastTriggeredAt(ctx context.Context, arg database.UpdateChatAutomationTriggerLastTriggeredAtParams) error {
-	trigger, err := q.db.GetChatAutomationTriggerByID(ctx, arg.ID)
-	if err != nil {
-		return err
-	}
-	automation, err := q.db.GetChatAutomationByID(ctx, trigger.AutomationID)
-	if err != nil {
-		return err
-	}
-	if err := q.authorizeContext(ctx, policy.ActionUpdate, automation); err != nil {
-		return err
-	}
-	return q.db.UpdateChatAutomationTriggerLastTriggeredAt(ctx, arg)
-}
-
-func (q *querier) UpdateChatAutomationTriggerWebhookSecret(ctx context.Context, arg database.UpdateChatAutomationTriggerWebhookSecretParams) (database.ChatAutomationTrigger, error) {
-	trigger, err := q.db.GetChatAutomationTriggerByID(ctx, arg.ID)
-	if err != nil {
-		return database.ChatAutomationTrigger{}, err
-	}
-	automation, err := q.db.GetChatAutomationByID(ctx, trigger.AutomationID)
-	if err != nil {
-		return database.ChatAutomationTrigger{}, err
-	}
-	if err := q.authorizeContext(ctx, policy.ActionUpdate, automation); err != nil {
-		return database.ChatAutomationTrigger{}, err
-	}
-	return q.db.UpdateChatAutomationTriggerWebhookSecret(ctx, arg)
-}
-
 func (q *querier) UpdateChatBuildAgentBinding(ctx context.Context, arg database.UpdateChatBuildAgentBindingParams) (database.Chat, error) {
 	chat, err := q.db.GetChatByID(ctx, arg.ID)
 	if err != nil {
@@ -5946,15 +5968,37 @@ func (q *querier) UpdateChatByID(ctx context.Context, arg database.UpdateChatByI
 	return q.db.UpdateChatByID(ctx, arg)
 }
 
-func (q *querier) UpdateChatHeartbeat(ctx context.Context, arg database.UpdateChatHeartbeatParams) (int64, error) {
-	chat, err := q.db.GetChatByID(ctx, arg.ID)
+func (q *querier) UpdateChatDebugRun(ctx context.Context, arg database.UpdateChatDebugRunParams) (database.ChatDebugRun, error) {
+	chat, err := q.db.GetChatByID(ctx, arg.ChatID)
 	if err != nil {
-		return 0, err
+		return database.ChatDebugRun{}, err
 	}
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
-		return 0, err
+		return database.ChatDebugRun{}, err
 	}
-	return q.db.UpdateChatHeartbeat(ctx, arg)
+	return q.db.UpdateChatDebugRun(ctx, arg)
+}
+
+func (q *querier) UpdateChatDebugStep(ctx context.Context, arg database.UpdateChatDebugStepParams) (database.ChatDebugStep, error) {
+	chat, err := q.db.GetChatByID(ctx, arg.ChatID)
+	if err != nil {
+		return database.ChatDebugStep{}, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
+		return database.ChatDebugStep{}, err
+	}
+	return q.db.UpdateChatDebugStep(ctx, arg)
+}
+
+func (q *querier) UpdateChatHeartbeats(ctx context.Context, arg database.UpdateChatHeartbeatsParams) ([]uuid.UUID, error) {
+	// The batch heartbeat is a system-level operation filtered by
+	// worker_id. Authorization is enforced by the AsChatd context
+	// at the call site rather than per-row, because checking each
+	// row individually would defeat the purpose of batching.
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceChat); err != nil {
+		return nil, err
+	}
+	return q.db.UpdateChatHeartbeats(ctx, arg)
 }
 
 func (q *querier) UpdateChatLabelsByID(ctx context.Context, arg database.UpdateChatLabelsByIDParams) (database.Chat, error) {
@@ -6662,6 +6706,17 @@ func (q *querier) UpdateUserChatCustomPrompt(ctx context.Context, arg database.U
 	return q.db.UpdateUserChatCustomPrompt(ctx, arg)
 }
 
+func (q *querier) UpdateUserChatProviderKey(ctx context.Context, arg database.UpdateUserChatProviderKeyParams) (database.UserChatProviderKey, error) {
+	u, err := q.db.GetUserByID(ctx, arg.UserID)
+	if err != nil {
+		return database.UserChatProviderKey{}, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdatePersonal, u); err != nil {
+		return database.UserChatProviderKey{}, err
+	}
+	return q.db.UpdateUserChatProviderKey(ctx, arg)
+}
+
 func (q *querier) UpdateUserDeletedByID(ctx context.Context, id uuid.UUID) error {
 	return deleteQ(q.log, q.auth, q.db.GetUserByID, q.db.UpdateUserDeletedByID)(ctx, id)
 }
@@ -6785,17 +6840,12 @@ func (q *querier) UpdateUserRoles(ctx context.Context, arg database.UpdateUserRo
 	return q.db.UpdateUserRoles(ctx, arg)
 }
 
-func (q *querier) UpdateUserSecret(ctx context.Context, arg database.UpdateUserSecretParams) (database.UserSecret, error) {
-	// First get the secret to check ownership
-	secret, err := q.db.GetUserSecret(ctx, arg.ID)
-	if err != nil {
+func (q *querier) UpdateUserSecretByUserIDAndName(ctx context.Context, arg database.UpdateUserSecretByUserIDAndNameParams) (database.UserSecret, error) {
+	obj := rbac.ResourceUserSecret.WithOwner(arg.UserID.String())
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, obj); err != nil {
 		return database.UserSecret{}, err
 	}
-
-	if err := q.authorizeContext(ctx, policy.ActionUpdate, secret); err != nil {
-		return database.UserSecret{}, err
-	}
-	return q.db.UpdateUserSecret(ctx, arg)
+	return q.db.UpdateUserSecretByUserIDAndName(ctx, arg)
 }
 
 func (q *querier) UpdateUserStatus(ctx context.Context, arg database.UpdateUserStatusParams) (database.User, error) {
@@ -6876,6 +6926,19 @@ func (q *querier) UpdateWorkspaceAgentConnectionByID(ctx context.Context, arg da
 	return q.db.UpdateWorkspaceAgentConnectionByID(ctx, arg)
 }
 
+func (q *querier) UpdateWorkspaceAgentDirectoryByID(ctx context.Context, arg database.UpdateWorkspaceAgentDirectoryByIDParams) error {
+	workspace, err := q.db.GetWorkspaceByAgentID(ctx, arg.ID)
+	if err != nil {
+		return err
+	}
+
+	if err := q.authorizeContext(ctx, policy.ActionUpdateAgent, workspace); err != nil {
+		return err
+	}
+
+	return q.db.UpdateWorkspaceAgentDirectoryByID(ctx, arg)
+}
+
 func (q *querier) UpdateWorkspaceAgentDisplayAppsByID(ctx context.Context, arg database.UpdateWorkspaceAgentDisplayAppsByIDParams) error {
 	workspace, err := q.db.GetWorkspaceByAgentID(ctx, arg.ID)
 	if err != nil {
@@ -7159,6 +7222,13 @@ func (q *querier) UpsertBoundaryUsageStats(ctx context.Context, arg database.Ups
 	return q.db.UpsertBoundaryUsageStats(ctx, arg)
 }
 
+func (q *querier) UpsertChatDebugLoggingAllowUsers(ctx context.Context, allowUsers bool) error {
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceDeploymentConfig); err != nil {
+		return err
+	}
+	return q.db.UpsertChatDebugLoggingAllowUsers(ctx, allowUsers)
+}
+
 func (q *querier) UpsertChatDesktopEnabled(ctx context.Context, enableDesktop bool) error {
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceDeploymentConfig); err != nil {
 		return err
@@ -7197,6 +7267,13 @@ func (q *querier) UpsertChatIncludeDefaultSystemPrompt(ctx context.Context, incl
 	return q.db.UpsertChatIncludeDefaultSystemPrompt(ctx, includeDefaultSystemPrompt)
 }
 
+func (q *querier) UpsertChatRetentionDays(ctx context.Context, retentionDays int32) error {
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceDeploymentConfig); err != nil {
+		return err
+	}
+	return q.db.UpsertChatRetentionDays(ctx, retentionDays)
+}
+
 func (q *querier) UpsertChatSystemPrompt(ctx context.Context, value string) error {
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceDeploymentConfig); err != nil {
 		return err
@@ -7240,13 +7317,6 @@ func (q *querier) UpsertChatWorkspaceTTL(ctx context.Context, workspaceTtl strin
 	return q.db.UpsertChatWorkspaceTTL(ctx, workspaceTtl)
 }
 
-func (q *querier) UpsertConnectionLog(ctx context.Context, arg database.UpsertConnectionLogParams) (database.ConnectionLog, error) {
-	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceConnectionLog); err != nil {
-		return database.ConnectionLog{}, err
-	}
-	return q.db.UpsertConnectionLog(ctx, arg)
-}
-
 func (q *querier) UpsertDefaultProxy(ctx context.Context, arg database.UpsertDefaultProxyParams) error {
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceSystem); err != nil {
 		return err
@@ -7389,6 +7459,28 @@ func (q *querier) UpsertTemplateUsageStats(ctx context.Context) error {
 	return q.db.UpsertTemplateUsageStats(ctx)
 }
 
+func (q *querier) UpsertUserChatDebugLoggingEnabled(ctx context.Context, arg database.UpsertUserChatDebugLoggingEnabledParams) error {
+	u, err := q.db.GetUserByID(ctx, arg.UserID)
+	if err != nil {
+		return err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdatePersonal, u); err != nil {
+		return err
+	}
+	return q.db.UpsertUserChatDebugLoggingEnabled(ctx, arg)
+}
+
+func (q *querier) UpsertUserChatProviderKey(ctx context.Context, arg database.UpsertUserChatProviderKeyParams) (database.UserChatProviderKey, error) {
+	u, err := q.db.GetUserByID(ctx, arg.UserID)
+	if err != nil {
+		return database.UserChatProviderKey{}, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdatePersonal, u); err != nil {
+		return database.UserChatProviderKey{}, err
+	}
+	return q.db.UpsertUserChatProviderKey(ctx, arg)
+}
+
 func (q *querier) UpsertWebpushVAPIDKeys(ctx context.Context, arg database.UpsertWebpushVAPIDKeysParams) error {
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceDeploymentConfig); err != nil {
 		return err
@@ -7560,7 +7652,3 @@ func (q *querier) ListAuthorizedAIBridgeSessionThreads(ctx context.Context, arg
 func (q *querier) GetAuthorizedChats(ctx context.Context, arg database.GetChatsParams, _ rbac.PreparedAuthorized) ([]database.GetChatsRow, error) {
 	return q.GetChats(ctx, arg)
 }
-
-func (q *querier) GetAuthorizedChatAutomations(ctx context.Context, arg database.GetChatAutomationsParams, _ rbac.PreparedAuthorized) ([]database.ChatAutomation, error) {
-	return q.GetChatAutomations(ctx, arg)
-}

coderd/database/dbauthz/dbauthz_test.go

@@ -338,10 +338,9 @@ func (s *MethodTestSuite) TestAuditLogs() {
 }
 
 func (s *MethodTestSuite) TestConnectionLogs() {
-	s.Run("UpsertConnectionLog", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		ws := testutil.Fake(s.T(), faker, database.WorkspaceTable{})
-		arg := database.UpsertConnectionLogParams{Ip: defaultIPAddress(), Type: database.ConnectionTypeSsh, WorkspaceID: ws.ID, OrganizationID: ws.OrganizationID, ConnectionStatus: database.ConnectionStatusConnected, WorkspaceOwnerID: ws.OwnerID}
-		dbm.EXPECT().UpsertConnectionLog(gomock.Any(), arg).Return(database.ConnectionLog{}, nil).AnyTimes()
+	s.Run("BatchUpsertConnectionLogs", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		arg := database.BatchUpsertConnectionLogsParams{}
+		dbm.EXPECT().BatchUpsertConnectionLogs(gomock.Any(), arg).Return(nil).AnyTimes()
 		check.Args(arg).Asserts(rbac.ResourceConnectionLog, policy.ActionUpdate)
 	}))
 	s.Run("GetConnectionLogsOffset", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
@@ -401,6 +400,17 @@ func (s *MethodTestSuite) TestChats() {
 		dbm.EXPECT().UnarchiveChatByID(gomock.Any(), chat.ID).Return([]database.Chat{chat}, nil).AnyTimes()
 		check.Args(chat.ID).Asserts(chat, policy.ActionUpdate).Returns([]database.Chat{chat})
 	}))
+	s.Run("LinkChatFiles", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		arg := database.LinkChatFilesParams{
+			ChatID:       chat.ID,
+			MaxFileLinks: int32(codersdk.MaxChatFileIDs),
+			FileIds:      []uuid.UUID{uuid.New()},
+		}
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		dbm.EXPECT().LinkChatFiles(gomock.Any(), arg).Return(int32(0), nil).AnyTimes()
+		check.Args(arg).Asserts(chat, policy.ActionUpdate).Returns(int32(0))
+	}))
 	s.Run("PinChatByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		chat := testutil.Fake(s.T(), faker, database.Chat{})
 		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
@@ -451,6 +461,89 @@ func (s *MethodTestSuite) TestChats() {
 		dbm.EXPECT().DeleteChatQueuedMessage(gomock.Any(), args).Return(nil).AnyTimes()
 		check.Args(args).Asserts(chat, policy.ActionUpdate).Returns()
 	}))
+	s.Run("DeleteChatDebugDataAfterMessageID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		arg := database.DeleteChatDebugDataAfterMessageIDParams{ChatID: chat.ID, MessageID: 123}
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		dbm.EXPECT().DeleteChatDebugDataAfterMessageID(gomock.Any(), arg).Return(int64(1), nil).AnyTimes()
+		check.Args(arg).Asserts(chat, policy.ActionUpdate).Returns(int64(1))
+	}))
+	s.Run("DeleteChatDebugDataByChatID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		dbm.EXPECT().DeleteChatDebugDataByChatID(gomock.Any(), chat.ID).Return(int64(1), nil).AnyTimes()
+		check.Args(chat.ID).Asserts(chat, policy.ActionUpdate).Returns(int64(1))
+	}))
+	s.Run("FinalizeStaleChatDebugRows", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		updatedBefore := dbtime.Now()
+		row := database.FinalizeStaleChatDebugRowsRow{RunsFinalized: 1, StepsFinalized: 2}
+		dbm.EXPECT().FinalizeStaleChatDebugRows(gomock.Any(), updatedBefore).Return(row, nil).AnyTimes()
+		check.Args(updatedBefore).Asserts(rbac.ResourceChat, policy.ActionUpdate).Returns(row)
+	}))
+	s.Run("GetChatDebugLoggingAllowUsers", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		dbm.EXPECT().GetChatDebugLoggingAllowUsers(gomock.Any()).Return(true, nil).AnyTimes()
+		check.Args().Asserts().Returns(true)
+	}))
+	s.Run("GetChatDebugRunByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		run := database.ChatDebugRun{ID: uuid.New(), ChatID: chat.ID}
+		dbm.EXPECT().GetChatDebugRunByID(gomock.Any(), run.ID).Return(run, nil).AnyTimes()
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		check.Args(run.ID).Asserts(chat, policy.ActionRead).Returns(run)
+	}))
+	s.Run("GetChatDebugRunsByChatID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		runs := []database.ChatDebugRun{{ID: uuid.New(), ChatID: chat.ID}}
+		arg := database.GetChatDebugRunsByChatIDParams{ChatID: chat.ID, LimitVal: 100}
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		dbm.EXPECT().GetChatDebugRunsByChatID(gomock.Any(), arg).Return(runs, nil).AnyTimes()
+		check.Args(arg).Asserts(chat, policy.ActionRead).Returns(runs)
+	}))
+	s.Run("GetChatDebugStepsByRunID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		run := database.ChatDebugRun{ID: uuid.New(), ChatID: chat.ID}
+		steps := []database.ChatDebugStep{{ID: uuid.New(), RunID: run.ID, ChatID: chat.ID}}
+		dbm.EXPECT().GetChatDebugRunByID(gomock.Any(), run.ID).Return(run, nil).AnyTimes()
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		dbm.EXPECT().GetChatDebugStepsByRunID(gomock.Any(), run.ID).Return(steps, nil).AnyTimes()
+		check.Args(run.ID).Asserts(chat, policy.ActionRead).Returns(steps)
+	}))
+	s.Run("InsertChatDebugRun", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		arg := database.InsertChatDebugRunParams{ChatID: chat.ID, Kind: "chat_turn", Status: "in_progress"}
+		run := database.ChatDebugRun{ID: uuid.New(), ChatID: chat.ID}
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		dbm.EXPECT().InsertChatDebugRun(gomock.Any(), arg).Return(run, nil).AnyTimes()
+		check.Args(arg).Asserts(chat, policy.ActionUpdate).Returns(run)
+	}))
+	s.Run("InsertChatDebugStep", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		arg := database.InsertChatDebugStepParams{RunID: uuid.New(), ChatID: chat.ID, StepNumber: 1, Operation: "stream", Status: "in_progress"}
+		step := database.ChatDebugStep{ID: uuid.New(), RunID: arg.RunID, ChatID: chat.ID}
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		dbm.EXPECT().InsertChatDebugStep(gomock.Any(), arg).Return(step, nil).AnyTimes()
+		check.Args(arg).Asserts(chat, policy.ActionUpdate).Returns(step)
+	}))
+	s.Run("UpdateChatDebugRun", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		arg := database.UpdateChatDebugRunParams{ID: uuid.New(), ChatID: chat.ID}
+		run := database.ChatDebugRun{ID: arg.ID, ChatID: chat.ID}
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		dbm.EXPECT().UpdateChatDebugRun(gomock.Any(), arg).Return(run, nil).AnyTimes()
+		check.Args(arg).Asserts(chat, policy.ActionUpdate).Returns(run)
+	}))
+	s.Run("UpdateChatDebugStep", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		arg := database.UpdateChatDebugStepParams{ID: uuid.New(), ChatID: chat.ID}
+		step := database.ChatDebugStep{ID: arg.ID, ChatID: chat.ID}
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		dbm.EXPECT().UpdateChatDebugStep(gomock.Any(), arg).Return(step, nil).AnyTimes()
+		check.Args(arg).Asserts(chat, policy.ActionUpdate).Returns(step)
+	}))
+	s.Run("UpsertChatDebugLoggingAllowUsers", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		dbm.EXPECT().UpsertChatDebugLoggingAllowUsers(gomock.Any(), true).Return(nil).AnyTimes()
+		check.Args(true).Asserts(rbac.ResourceDeploymentConfig, policy.ActionUpdate)
+	}))
 	s.Run("GetChatByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		chat := testutil.Fake(s.T(), faker, database.Chat{})
 		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
@@ -468,6 +561,24 @@ func (s *MethodTestSuite) TestChats() {
 		dbm.EXPECT().GetChatsByWorkspaceIDs(gomock.Any(), arg).Return([]database.Chat{chatA, chatB}, nil).AnyTimes()
 		check.Args(arg).Asserts(chatA, policy.ActionRead, chatB, policy.ActionRead).Returns([]database.Chat{chatA, chatB})
 	}))
+	s.Run("GetActiveChatsByAgentID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		agentID := uuid.New()
+		dbm.EXPECT().GetActiveChatsByAgentID(gomock.Any(), agentID).Return([]database.Chat{chat}, nil).AnyTimes()
+		check.Args(agentID).Asserts(chat, policy.ActionRead).Returns([]database.Chat{chat})
+	}))
+	s.Run("SoftDeleteContextFileMessages", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		dbm.EXPECT().SoftDeleteContextFileMessages(gomock.Any(), chat.ID).Return(nil).AnyTimes()
+		check.Args(chat.ID).Asserts(chat, policy.ActionUpdate).Returns()
+	}))
+	s.Run("ClearChatMessageProviderResponseIDsByChatID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		dbm.EXPECT().ClearChatMessageProviderResponseIDsByChatID(gomock.Any(), chat.ID).Return(nil).AnyTimes()
+		check.Args(chat.ID).Asserts(chat, policy.ActionUpdate).Returns()
+	}))
 	s.Run("GetChatCostPerChat", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
 		arg := database.GetChatCostPerChatParams{
 			OwnerID:   uuid.New(),
@@ -577,6 +688,35 @@ func (s *MethodTestSuite) TestChats() {
 		dbm.EXPECT().GetChatFilesByIDs(gomock.Any(), []uuid.UUID{file.ID}).Return([]database.ChatFile{file}, nil).AnyTimes()
 		check.Args([]uuid.UUID{file.ID}).Asserts(rbac.ResourceChat.WithOwner(file.OwnerID.String()).InOrg(file.OrganizationID).WithID(file.ID), policy.ActionRead).Returns([]database.ChatFile{file})
 	}))
+	s.Run("GetChatFileMetadataByChatID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		file := testutil.Fake(s.T(), faker, database.ChatFile{})
+		rows := []database.GetChatFileMetadataByChatIDRow{{
+			ID:             file.ID,
+			Name:           file.Name,
+			Mimetype:       file.Mimetype,
+			CreatedAt:      file.CreatedAt,
+			OwnerID:        file.OwnerID,
+			OrganizationID: file.OrganizationID,
+		}}
+		dbm.EXPECT().GetChatFileMetadataByChatID(gomock.Any(), file.ID).Return(rows, nil).AnyTimes()
+		check.Args(file.ID).Asserts(rbac.ResourceChat.WithOwner(file.OwnerID.String()).InOrg(file.OrganizationID).WithID(file.ID), policy.ActionRead).Returns(rows)
+	}))
+	s.Run("DeleteOldChatFiles", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		dbm.EXPECT().DeleteOldChatFiles(gomock.Any(), database.DeleteOldChatFilesParams{}).Return(int64(0), nil).AnyTimes()
+		check.Args(database.DeleteOldChatFilesParams{}).Asserts(rbac.ResourceSystem, policy.ActionDelete)
+	}))
+	s.Run("DeleteOldChats", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		dbm.EXPECT().DeleteOldChats(gomock.Any(), database.DeleteOldChatsParams{}).Return(int64(0), nil).AnyTimes()
+		check.Args(database.DeleteOldChatsParams{}).Asserts(rbac.ResourceSystem, policy.ActionDelete)
+	}))
+	s.Run("GetChatRetentionDays", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		dbm.EXPECT().GetChatRetentionDays(gomock.Any()).Return(int32(30), nil).AnyTimes()
+		check.Args().Asserts()
+	}))
+	s.Run("UpsertChatRetentionDays", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		dbm.EXPECT().UpsertChatRetentionDays(gomock.Any(), int32(30)).Return(nil).AnyTimes()
+		check.Args(int32(30)).Asserts(rbac.ResourceDeploymentConfig, policy.ActionUpdate)
+	}))
 	s.Run("GetChatMessageByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		chat := testutil.Fake(s.T(), faker, database.Chat{})
 		msg := testutil.Fake(s.T(), faker, database.ChatMessage{ChatID: chat.ID})
@@ -721,7 +861,9 @@ func (s *MethodTestSuite) TestChats() {
 		check.Args(threshold).Asserts(rbac.ResourceChat, policy.ActionRead).Returns(chats)
 	}))
 	s.Run("InsertChat", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		arg := testutil.Fake(s.T(), faker, database.InsertChatParams{})
+		arg := testutil.Fake(s.T(), faker, database.InsertChatParams{
+			Status: database.ChatStatusWaiting,
+		})
 		chat := testutil.Fake(s.T(), faker, database.Chat{OwnerID: arg.OwnerID})
 		dbm.EXPECT().InsertChat(gomock.Any(), arg).Return(chat, nil).AnyTimes()
 		check.Args(arg).Asserts(rbac.ResourceChat.WithOwner(arg.OwnerID.String()), policy.ActionCreate).Returns(chat)
@@ -817,15 +959,15 @@ func (s *MethodTestSuite) TestChats() {
 		dbm.EXPECT().UpdateChatStatusPreserveUpdatedAt(gomock.Any(), arg).Return(chat, nil).AnyTimes()
 		check.Args(arg).Asserts(chat, policy.ActionUpdate).Returns(chat)
 	}))
-	s.Run("UpdateChatHeartbeat", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		chat := testutil.Fake(s.T(), faker, database.Chat{})
-		arg := database.UpdateChatHeartbeatParams{
-			ID:       chat.ID,
+	s.Run("UpdateChatHeartbeats", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		resultID := uuid.New()
+		arg := database.UpdateChatHeartbeatsParams{
+			IDs:      []uuid.UUID{resultID},
 			WorkerID: uuid.New(),
+			Now:      time.Now(),
 		}
-		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
-		dbm.EXPECT().UpdateChatHeartbeat(gomock.Any(), arg).Return(int64(1), nil).AnyTimes()
-		check.Args(arg).Asserts(chat, policy.ActionUpdate).Returns(int64(1))
+		dbm.EXPECT().UpdateChatHeartbeats(gomock.Any(), arg).Return([]uuid.UUID{resultID}, nil).AnyTimes()
+		check.Args(arg).Asserts(rbac.ResourceChat, policy.ActionUpdate).Returns([]uuid.UUID{resultID})
 	}))
 	s.Run("UpdateChatMessageByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		chat := testutil.Fake(s.T(), faker, database.Chat{})
@@ -1121,10 +1263,6 @@ func (s *MethodTestSuite) TestChats() {
 		dbm.EXPECT().CleanupDeletedMCPServerIDsFromChats(gomock.Any()).Return(nil).AnyTimes()
 		check.Args().Asserts(rbac.ResourceChat, policy.ActionUpdate)
 	}))
-	s.Run("CleanupDeletedMCPServerIDsFromChatAutomations", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
-		dbm.EXPECT().CleanupDeletedMCPServerIDsFromChatAutomations(gomock.Any()).Return(nil).AnyTimes()
-		check.Args().Asserts(rbac.ResourceChatAutomation, policy.ActionUpdate)
-	}))
 	s.Run("DeleteMCPServerConfigByID", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
 		id := uuid.New()
 		dbm.EXPECT().DeleteMCPServerConfigByID(gomock.Any(), id).Return(nil).AnyTimes()
@@ -1254,226 +1392,6 @@ func (s *MethodTestSuite) TestChats() {
 	}))
 }
 
-func (s *MethodTestSuite) TestChatAutomations() {
-	s.Run("CountChatAutomationChatCreatesInWindow", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
-		arg := database.CountChatAutomationChatCreatesInWindowParams{
-			AutomationID: automation.ID,
-			WindowStart:  dbtime.Now().Add(-time.Hour),
-		}
-		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
-		dbm.EXPECT().CountChatAutomationChatCreatesInWindow(gomock.Any(), arg).Return(int64(3), nil).AnyTimes()
-		check.Args(arg).Asserts(automation, policy.ActionRead).Returns(int64(3))
-	}))
-	s.Run("CountChatAutomationMessagesInWindow", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
-		arg := database.CountChatAutomationMessagesInWindowParams{
-			AutomationID: automation.ID,
-			WindowStart:  dbtime.Now().Add(-time.Hour),
-		}
-		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
-		dbm.EXPECT().CountChatAutomationMessagesInWindow(gomock.Any(), arg).Return(int64(5), nil).AnyTimes()
-		check.Args(arg).Asserts(automation, policy.ActionRead).Returns(int64(5))
-	}))
-	s.Run("DeleteChatAutomationByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
-		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
-		dbm.EXPECT().DeleteChatAutomationByID(gomock.Any(), automation.ID).Return(nil).AnyTimes()
-		check.Args(automation.ID).Asserts(automation, policy.ActionDelete).Returns()
-	}))
-	s.Run("DeleteChatAutomationTriggerByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
-		trigger := testutil.Fake(s.T(), faker, database.ChatAutomationTrigger{
-			AutomationID: automation.ID,
-			Type:         database.ChatAutomationTriggerTypeWebhook,
-		})
-		dbm.EXPECT().GetChatAutomationTriggerByID(gomock.Any(), trigger.ID).Return(trigger, nil).AnyTimes()
-		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
-		dbm.EXPECT().DeleteChatAutomationTriggerByID(gomock.Any(), trigger.ID).Return(nil).AnyTimes()
-		check.Args(trigger.ID).Asserts(automation, policy.ActionUpdate).Returns()
-	}))
-	s.Run("GetActiveChatAutomationCronTriggers", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
-		rows := []database.GetActiveChatAutomationCronTriggersRow{}
-		dbm.EXPECT().GetActiveChatAutomationCronTriggers(gomock.Any()).Return(rows, nil).AnyTimes()
-		check.Args().Asserts(rbac.ResourceChatAutomation.All(), policy.ActionRead).Returns(rows)
-	}))
-	s.Run("GetChatAutomationByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
-		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
-		check.Args(automation.ID).Asserts(automation, policy.ActionRead).Returns(automation)
-	}))
-	s.Run("GetChatAutomationEventsByAutomationID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
-		arg := database.GetChatAutomationEventsByAutomationIDParams{
-			AutomationID: automation.ID,
-		}
-		events := []database.ChatAutomationEvent{}
-		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
-		dbm.EXPECT().GetChatAutomationEventsByAutomationID(gomock.Any(), arg).Return(events, nil).AnyTimes()
-		check.Args(arg).Asserts(automation, policy.ActionRead).Returns(events)
-	}))
-	s.Run("GetChatAutomationTriggerByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
-		trigger := testutil.Fake(s.T(), faker, database.ChatAutomationTrigger{
-			AutomationID: automation.ID,
-			Type:         database.ChatAutomationTriggerTypeWebhook,
-		})
-		dbm.EXPECT().GetChatAutomationTriggerByID(gomock.Any(), trigger.ID).Return(trigger, nil).AnyTimes()
-		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
-		check.Args(trigger.ID).Asserts(automation, policy.ActionRead).Returns(trigger)
-	}))
-	s.Run("GetChatAutomationTriggersByAutomationID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
-		triggers := []database.ChatAutomationTrigger{}
-		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
-		dbm.EXPECT().GetChatAutomationTriggersByAutomationID(gomock.Any(), automation.ID).Return(triggers, nil).AnyTimes()
-		check.Args(automation.ID).Asserts(automation, policy.ActionRead).Returns(triggers)
-	}))
-	s.Run("GetChatAutomations", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
-		params := database.GetChatAutomationsParams{}
-		dbm.EXPECT().GetChatAutomations(gomock.Any(), params).Return([]database.ChatAutomation{}, nil).AnyTimes()
-		dbm.EXPECT().GetAuthorizedChatAutomations(gomock.Any(), params, gomock.Any()).Return([]database.ChatAutomation{}, nil).AnyTimes()
-		check.Args(params).Asserts(rbac.ResourceChatAutomation.All(), policy.ActionRead).WithNotAuthorized("nil")
-	}))
-	s.Run("GetAuthorizedChatAutomations", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
-		params := database.GetChatAutomationsParams{}
-		dbm.EXPECT().GetAuthorizedChatAutomations(gomock.Any(), params, gomock.Any()).Return([]database.ChatAutomation{}, nil).AnyTimes()
-		dbm.EXPECT().GetChatAutomations(gomock.Any(), params).Return([]database.ChatAutomation{}, nil).AnyTimes()
-		check.Args(params, emptyPreparedAuthorized{}).Asserts(rbac.ResourceChatAutomation.All(), policy.ActionRead)
-	}))
-	s.Run("InsertChatAutomation", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		arg := database.InsertChatAutomationParams{
-			ID:             uuid.New(),
-			OwnerID:        uuid.New(),
-			OrganizationID: uuid.New(),
-			Name:           "test-automation",
-			Description:    "test description",
-			Instructions:   "test instructions",
-			Status:         database.ChatAutomationStatusActive,
-			CreatedAt:      dbtime.Now(),
-			UpdatedAt:      dbtime.Now(),
-		}
-		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{
-			ID:             arg.ID,
-			OwnerID:        arg.OwnerID,
-			OrganizationID: arg.OrganizationID,
-			Status:         arg.Status,
-		})
-		dbm.EXPECT().InsertChatAutomation(gomock.Any(), arg).Return(automation, nil).AnyTimes()
-		check.Args(arg).Asserts(rbac.ResourceChatAutomation.WithOwner(arg.OwnerID.String()).InOrg(arg.OrganizationID), policy.ActionCreate).Returns(automation)
-	}))
-	s.Run("InsertChatAutomationEvent", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
-		arg := database.InsertChatAutomationEventParams{
-			ID:           uuid.New(),
-			AutomationID: automation.ID,
-			ReceivedAt:   dbtime.Now(),
-			Payload:      json.RawMessage(`{}`),
-			Status:       database.ChatAutomationEventStatusFiltered,
-		}
-		event := testutil.Fake(s.T(), faker, database.ChatAutomationEvent{
-			ID:           arg.ID,
-			AutomationID: automation.ID,
-			Status:       arg.Status,
-		})
-		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
-		dbm.EXPECT().InsertChatAutomationEvent(gomock.Any(), arg).Return(event, nil).AnyTimes()
-		check.Args(arg).Asserts(automation, policy.ActionUpdate).Returns(event)
-	}))
-	s.Run("InsertChatAutomationTrigger", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
-		arg := database.InsertChatAutomationTriggerParams{
-			ID:           uuid.New(),
-			AutomationID: automation.ID,
-			Type:         database.ChatAutomationTriggerTypeWebhook,
-			CreatedAt:    dbtime.Now(),
-			UpdatedAt:    dbtime.Now(),
-		}
-		trigger := testutil.Fake(s.T(), faker, database.ChatAutomationTrigger{
-			ID:           arg.ID,
-			AutomationID: automation.ID,
-			Type:         arg.Type,
-		})
-		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
-		dbm.EXPECT().InsertChatAutomationTrigger(gomock.Any(), arg).Return(trigger, nil).AnyTimes()
-		check.Args(arg).Asserts(automation, policy.ActionUpdate).Returns(trigger)
-	}))
-	s.Run("PurgeOldChatAutomationEvents", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
-		arg := database.PurgeOldChatAutomationEventsParams{
-			Before:     dbtime.Now().Add(-7 * 24 * time.Hour),
-			LimitCount: 1000,
-		}
-		dbm.EXPECT().PurgeOldChatAutomationEvents(gomock.Any(), arg).Return(int64(5), nil).AnyTimes()
-		check.Args(arg).Asserts(rbac.ResourceChatAutomation.All(), policy.ActionDelete).Returns(int64(5))
-	}))
-	s.Run("UpdateChatAutomation", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
-		arg := database.UpdateChatAutomationParams{
-			ID:          automation.ID,
-			Name:        "updated-name",
-			Description: "updated description",
-			Status:      database.ChatAutomationStatusActive,
-			UpdatedAt:   dbtime.Now(),
-		}
-		updated := automation
-		updated.Name = arg.Name
-		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
-		dbm.EXPECT().UpdateChatAutomation(gomock.Any(), arg).Return(updated, nil).AnyTimes()
-		check.Args(arg).Asserts(automation, policy.ActionUpdate).Returns(updated)
-	}))
-	s.Run("UpdateChatAutomationTrigger", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
-		trigger := testutil.Fake(s.T(), faker, database.ChatAutomationTrigger{
-			AutomationID: automation.ID,
-			Type:         database.ChatAutomationTriggerTypeCron,
-		})
-		arg := database.UpdateChatAutomationTriggerParams{
-			ID:        trigger.ID,
-			UpdatedAt: dbtime.Now(),
-		}
-		updated := trigger
-		dbm.EXPECT().GetChatAutomationTriggerByID(gomock.Any(), trigger.ID).Return(trigger, nil).AnyTimes()
-		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
-		dbm.EXPECT().UpdateChatAutomationTrigger(gomock.Any(), arg).Return(updated, nil).AnyTimes()
-		check.Args(arg).Asserts(automation, policy.ActionUpdate).Returns(updated)
-	}))
-	s.Run("UpdateChatAutomationTriggerLastTriggeredAt", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
-		trigger := testutil.Fake(s.T(), faker, database.ChatAutomationTrigger{
-			AutomationID: automation.ID,
-			Type:         database.ChatAutomationTriggerTypeCron,
-		})
-		arg := database.UpdateChatAutomationTriggerLastTriggeredAtParams{
-			ID:              trigger.ID,
-			LastTriggeredAt: dbtime.Now(),
-		}
-		dbm.EXPECT().GetChatAutomationTriggerByID(gomock.Any(), trigger.ID).Return(trigger, nil).AnyTimes()
-		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
-		dbm.EXPECT().UpdateChatAutomationTriggerLastTriggeredAt(gomock.Any(), arg).Return(nil).AnyTimes()
-		check.Args(arg).Asserts(automation, policy.ActionUpdate).Returns()
-	}))
-	s.Run("UpdateChatAutomationTriggerWebhookSecret", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
-		trigger := testutil.Fake(s.T(), faker, database.ChatAutomationTrigger{
-			AutomationID: automation.ID,
-			Type:         database.ChatAutomationTriggerTypeWebhook,
-		})
-		arg := database.UpdateChatAutomationTriggerWebhookSecretParams{
-			ID:        trigger.ID,
-			UpdatedAt: dbtime.Now(),
-			WebhookSecret: sql.NullString{
-				String: "new-secret",
-				Valid:  true,
-			},
-		}
-		updated := trigger
-		dbm.EXPECT().GetChatAutomationTriggerByID(gomock.Any(), trigger.ID).Return(trigger, nil).AnyTimes()
-		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
-		dbm.EXPECT().UpdateChatAutomationTriggerWebhookSecret(gomock.Any(), arg).Return(updated, nil).AnyTimes()
-		check.Args(arg).Asserts(automation, policy.ActionUpdate).Returns(updated)
-	}))
-}
-
 func (s *MethodTestSuite) TestFile() {
 	s.Run("GetFileByHashAndCreator", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		f := testutil.Fake(s.T(), faker, database.File{})
@@ -2426,9 +2344,9 @@ func (s *MethodTestSuite) TestTemplate() {
 		dbm.EXPECT().GetPRInsightsPerModel(gomock.Any(), arg).Return([]database.GetPRInsightsPerModelRow{}, nil).AnyTimes()
 		check.Args(arg).Asserts(rbac.ResourceDeploymentConfig, policy.ActionRead)
 	}))
-	s.Run("GetPRInsightsRecentPRs", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
-		arg := database.GetPRInsightsRecentPRsParams{}
-		dbm.EXPECT().GetPRInsightsRecentPRs(gomock.Any(), arg).Return([]database.GetPRInsightsRecentPRsRow{}, nil).AnyTimes()
+	s.Run("GetPRInsightsPullRequests", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		arg := database.GetPRInsightsPullRequestsParams{}
+		dbm.EXPECT().GetPRInsightsPullRequests(gomock.Any(), arg).Return([]database.GetPRInsightsPullRequestsRow{}, nil).AnyTimes()
 		check.Args(arg).Asserts(rbac.ResourceDeploymentConfig, policy.ActionRead)
 	}))
 	s.Run("GetTelemetryTaskEvents", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
@@ -2629,6 +2547,49 @@ func (s *MethodTestSuite) TestUser() {
 		dbm.EXPECT().GetUserChatCustomPrompt(gomock.Any(), u.ID).Return("my custom prompt", nil).AnyTimes()
 		check.Args(u.ID).Asserts(u, policy.ActionReadPersonal).Returns("my custom prompt")
 	}))
+	s.Run("GetUserChatProviderKeys", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		u := testutil.Fake(s.T(), faker, database.User{})
+		key := testutil.Fake(s.T(), faker, database.UserChatProviderKey{UserID: u.ID})
+		dbm.EXPECT().GetUserByID(gomock.Any(), u.ID).Return(u, nil).AnyTimes()
+		dbm.EXPECT().GetUserChatProviderKeys(gomock.Any(), u.ID).Return([]database.UserChatProviderKey{key}, nil).AnyTimes()
+		check.Args(u.ID).Asserts(u, policy.ActionReadPersonal).Returns([]database.UserChatProviderKey{key})
+	}))
+	s.Run("DeleteUserChatProviderKey", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		u := testutil.Fake(s.T(), faker, database.User{})
+		arg := database.DeleteUserChatProviderKeyParams{UserID: u.ID, ChatProviderID: uuid.New()}
+		dbm.EXPECT().GetUserByID(gomock.Any(), u.ID).Return(u, nil).AnyTimes()
+		dbm.EXPECT().DeleteUserChatProviderKey(gomock.Any(), arg).Return(nil).AnyTimes()
+		check.Args(arg).Asserts(u, policy.ActionUpdatePersonal).Returns()
+	}))
+	s.Run("UpdateUserChatProviderKey", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		u := testutil.Fake(s.T(), faker, database.User{})
+		arg := database.UpdateUserChatProviderKeyParams{UserID: u.ID, ChatProviderID: uuid.New(), APIKey: "updated-api-key"}
+		key := testutil.Fake(s.T(), faker, database.UserChatProviderKey{UserID: u.ID, ChatProviderID: arg.ChatProviderID, APIKey: arg.APIKey})
+		dbm.EXPECT().GetUserByID(gomock.Any(), u.ID).Return(u, nil).AnyTimes()
+		dbm.EXPECT().UpdateUserChatProviderKey(gomock.Any(), arg).Return(key, nil).AnyTimes()
+		check.Args(arg).Asserts(u, policy.ActionUpdatePersonal).Returns(key)
+	}))
+	s.Run("UpsertUserChatProviderKey", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		u := testutil.Fake(s.T(), faker, database.User{})
+		arg := database.UpsertUserChatProviderKeyParams{UserID: u.ID, ChatProviderID: uuid.New(), APIKey: "upserted-api-key"}
+		key := testutil.Fake(s.T(), faker, database.UserChatProviderKey{UserID: u.ID, ChatProviderID: arg.ChatProviderID, APIKey: arg.APIKey})
+		dbm.EXPECT().GetUserByID(gomock.Any(), u.ID).Return(u, nil).AnyTimes()
+		dbm.EXPECT().UpsertUserChatProviderKey(gomock.Any(), arg).Return(key, nil).AnyTimes()
+		check.Args(arg).Asserts(u, policy.ActionUpdatePersonal).Returns(key)
+	}))
+	s.Run("GetUserChatDebugLoggingEnabled", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		u := testutil.Fake(s.T(), faker, database.User{})
+		dbm.EXPECT().GetUserByID(gomock.Any(), u.ID).Return(u, nil).AnyTimes()
+		dbm.EXPECT().GetUserChatDebugLoggingEnabled(gomock.Any(), u.ID).Return(true, nil).AnyTimes()
+		check.Args(u.ID).Asserts(u, policy.ActionReadPersonal).Returns(true)
+	}))
+	s.Run("UpsertUserChatDebugLoggingEnabled", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		u := testutil.Fake(s.T(), faker, database.User{})
+		arg := database.UpsertUserChatDebugLoggingEnabledParams{UserID: u.ID, DebugLoggingEnabled: true}
+		dbm.EXPECT().GetUserByID(gomock.Any(), u.ID).Return(u, nil).AnyTimes()
+		dbm.EXPECT().UpsertUserChatDebugLoggingEnabled(gomock.Any(), arg).Return(nil).AnyTimes()
+		check.Args(arg).Asserts(u, policy.ActionUpdatePersonal)
+	}))
 	s.Run("UpdateUserChatCustomPrompt", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		u := testutil.Fake(s.T(), faker, database.User{})
 		uc := database.UserConfig{UserID: u.ID, Key: "chat_custom_prompt", Value: "my custom prompt"}
@@ -3070,6 +3031,17 @@ func (s *MethodTestSuite) TestWorkspace() {
 		dbm.EXPECT().UpdateWorkspaceAgentStartupByID(gomock.Any(), arg).Return(nil).AnyTimes()
 		check.Args(arg).Asserts(w, policy.ActionUpdate).Returns()
 	}))
+	s.Run("UpdateWorkspaceAgentDirectoryByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		w := testutil.Fake(s.T(), faker, database.Workspace{})
+		agt := testutil.Fake(s.T(), faker, database.WorkspaceAgent{})
+		arg := database.UpdateWorkspaceAgentDirectoryByIDParams{
+			ID:        agt.ID,
+			Directory: "/workspaces/project",
+		}
+		dbm.EXPECT().GetWorkspaceByAgentID(gomock.Any(), agt.ID).Return(w, nil).AnyTimes()
+		dbm.EXPECT().UpdateWorkspaceAgentDirectoryByID(gomock.Any(), arg).Return(nil).AnyTimes()
+		check.Args(arg).Asserts(w, policy.ActionUpdateAgent).Returns()
+	}))
 	s.Run("UpdateWorkspaceAgentDisplayAppsByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		w := testutil.Fake(s.T(), faker, database.Workspace{})
 		agt := testutil.Fake(s.T(), faker, database.WorkspaceAgent{})
@@ -3942,13 +3914,11 @@ func (s *MethodTestSuite) TestTailnetFunctions() {
 		check.Args(uuid.New()).
 			Asserts(rbac.ResourceTailnetCoordinator, policy.ActionRead)
 	}))
-	s.Run("GetTailnetTunnelPeerBindings", s.Subtest(func(_ database.Store, check *expects) {
-		check.Args(uuid.New()).
-			Asserts(rbac.ResourceTailnetCoordinator, policy.ActionRead)
+	s.Run("GetTailnetTunnelPeerBindingsBatch", s.Subtest(func(_ database.Store, check *expects) {
+		check.Args([]uuid.UUID{uuid.New()}).Asserts(rbac.ResourceTailnetCoordinator, policy.ActionRead)
 	}))
-	s.Run("GetTailnetTunnelPeerIDs", s.Subtest(func(_ database.Store, check *expects) {
-		check.Args(uuid.New()).
-			Asserts(rbac.ResourceTailnetCoordinator, policy.ActionRead)
+	s.Run("GetTailnetTunnelPeerIDsBatch", s.Subtest(func(_ database.Store, check *expects) {
+		check.Args([]uuid.UUID{uuid.New()}).Asserts(rbac.ResourceTailnetCoordinator, policy.ActionRead)
 	}))
 	s.Run("GetAllTailnetCoordinators", s.Subtest(func(_ database.Store, check *expects) {
 		check.Args().
@@ -4167,6 +4137,20 @@ func (s *MethodTestSuite) TestSystemFunctions() {
 		dbm.EXPECT().GetWorkspaceAgentsCreatedAfter(gomock.Any(), ts).Return([]database.WorkspaceAgent{}, nil).AnyTimes()
 		check.Args(ts).Asserts(rbac.ResourceSystem, policy.ActionRead)
 	}))
+	s.Run("GetChatsUpdatedAfter", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		ts := dbtime.Now()
+		dbm.EXPECT().GetChatsUpdatedAfter(gomock.Any(), ts).Return([]database.GetChatsUpdatedAfterRow{}, nil).AnyTimes()
+		check.Args(ts).Asserts(rbac.ResourceSystem, policy.ActionRead)
+	}))
+	s.Run("GetChatMessageSummariesPerChat", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		ts := dbtime.Now()
+		dbm.EXPECT().GetChatMessageSummariesPerChat(gomock.Any(), ts).Return([]database.GetChatMessageSummariesPerChatRow{}, nil).AnyTimes()
+		check.Args(ts).Asserts(rbac.ResourceSystem, policy.ActionRead)
+	}))
+	s.Run("GetChatModelConfigsForTelemetry", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		dbm.EXPECT().GetChatModelConfigsForTelemetry(gomock.Any()).Return([]database.GetChatModelConfigsForTelemetryRow{}, nil).AnyTimes()
+		check.Args().Asserts(rbac.ResourceSystem, policy.ActionRead)
+	}))
 	s.Run("GetWorkspaceAppsCreatedAfter", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
 		ts := dbtime.Now()
 		dbm.EXPECT().GetWorkspaceAppsCreatedAfter(gomock.Any(), ts).Return([]database.WorkspaceApp{}, nil).AnyTimes()
@@ -5517,19 +5501,20 @@ func (s *MethodTestSuite) TestUserSecrets() {
 			Asserts(rbac.ResourceUserSecret.WithOwner(user.ID.String()), policy.ActionRead).
 			Returns(secret)
 	}))
-	s.Run("GetUserSecret", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		secret := testutil.Fake(s.T(), faker, database.UserSecret{})
-		dbm.EXPECT().GetUserSecret(gomock.Any(), secret.ID).Return(secret, nil).AnyTimes()
-		check.Args(secret.ID).
-			Asserts(secret, policy.ActionRead).
-			Returns(secret)
-	}))
 	s.Run("ListUserSecrets", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		user := testutil.Fake(s.T(), faker, database.User{})
-		secret := testutil.Fake(s.T(), faker, database.UserSecret{UserID: user.ID})
-		dbm.EXPECT().ListUserSecrets(gomock.Any(), user.ID).Return([]database.UserSecret{secret}, nil).AnyTimes()
+		row := testutil.Fake(s.T(), faker, database.ListUserSecretsRow{UserID: user.ID})
+		dbm.EXPECT().ListUserSecrets(gomock.Any(), user.ID).Return([]database.ListUserSecretsRow{row}, nil).AnyTimes()
 		check.Args(user.ID).
 			Asserts(rbac.ResourceUserSecret.WithOwner(user.ID.String()), policy.ActionRead).
+			Returns([]database.ListUserSecretsRow{row})
+	}))
+	s.Run("ListUserSecretsWithValues", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		user := testutil.Fake(s.T(), faker, database.User{})
+		secret := testutil.Fake(s.T(), faker, database.UserSecret{UserID: user.ID})
+		dbm.EXPECT().ListUserSecretsWithValues(gomock.Any(), user.ID).Return([]database.UserSecret{secret}, nil).AnyTimes()
+		check.Args(user.ID).
+			Asserts(rbac.ResourceSystem, policy.ActionRead).
 			Returns([]database.UserSecret{secret})
 	}))
 	s.Run("CreateUserSecret", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
@@ -5541,23 +5526,22 @@ func (s *MethodTestSuite) TestUserSecrets() {
 			Asserts(rbac.ResourceUserSecret.WithOwner(user.ID.String()), policy.ActionCreate).
 			Returns(ret)
 	}))
-	s.Run("UpdateUserSecret", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		secret := testutil.Fake(s.T(), faker, database.UserSecret{})
-		updated := testutil.Fake(s.T(), faker, database.UserSecret{ID: secret.ID})
-		arg := database.UpdateUserSecretParams{ID: secret.ID}
-		dbm.EXPECT().GetUserSecret(gomock.Any(), secret.ID).Return(secret, nil).AnyTimes()
-		dbm.EXPECT().UpdateUserSecret(gomock.Any(), arg).Return(updated, nil).AnyTimes()
+	s.Run("UpdateUserSecretByUserIDAndName", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		user := testutil.Fake(s.T(), faker, database.User{})
+		updated := testutil.Fake(s.T(), faker, database.UserSecret{UserID: user.ID})
+		arg := database.UpdateUserSecretByUserIDAndNameParams{UserID: user.ID, Name: "test"}
+		dbm.EXPECT().UpdateUserSecretByUserIDAndName(gomock.Any(), arg).Return(updated, nil).AnyTimes()
 		check.Args(arg).
-			Asserts(secret, policy.ActionUpdate).
+			Asserts(rbac.ResourceUserSecret.WithOwner(user.ID.String()), policy.ActionUpdate).
 			Returns(updated)
 	}))
-	s.Run("DeleteUserSecret", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		secret := testutil.Fake(s.T(), faker, database.UserSecret{})
-		dbm.EXPECT().GetUserSecret(gomock.Any(), secret.ID).Return(secret, nil).AnyTimes()
-		dbm.EXPECT().DeleteUserSecret(gomock.Any(), secret.ID).Return(nil).AnyTimes()
-		check.Args(secret.ID).
-			Asserts(secret, policy.ActionRead, secret, policy.ActionDelete).
-			Returns()
+	s.Run("DeleteUserSecretByUserIDAndName", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		user := testutil.Fake(s.T(), faker, database.User{})
+		arg := database.DeleteUserSecretByUserIDAndNameParams{UserID: user.ID, Name: "test"}
+		dbm.EXPECT().DeleteUserSecretByUserIDAndName(gomock.Any(), arg).Return(int64(1), nil).AnyTimes()
+		check.Args(arg).
+			Asserts(rbac.ResourceUserSecret.WithOwner(user.ID.String()), policy.ActionDelete).
+			Returns(int64(1))
 	}))
 }
 

coderd/database/dbgen/dbgen.go

@@ -76,7 +76,7 @@ func AuditLog(t testing.TB, db database.Store, seed database.AuditLog) database.
 }
 
 func ConnectionLog(t testing.TB, db database.Store, seed database.UpsertConnectionLogParams) database.ConnectionLog {
-	log, err := db.UpsertConnectionLog(genCtx, database.UpsertConnectionLogParams{
+	arg := database.UpsertConnectionLogParams{
 		ID:               takeFirst(seed.ID, uuid.New()),
 		Time:             takeFirst(seed.Time, dbtime.Now()),
 		OrganizationID:   takeFirst(seed.OrganizationID, uuid.New()),
@@ -89,7 +89,7 @@ func ConnectionLog(t testing.TB, db database.Store, seed database.UpsertConnecti
 			Int32: takeFirst(seed.Code.Int32, 0),
 			Valid: takeFirst(seed.Code.Valid, false),
 		},
-		Ip: pqtype.Inet{
+		IP: pqtype.Inet{
 			IPNet: net.IPNet{
 				IP:   net.IPv4(127, 0, 0, 1),
 				Mask: net.IPv4Mask(255, 255, 255, 255),
@@ -117,9 +117,53 @@ func ConnectionLog(t testing.TB, db database.Store, seed database.UpsertConnecti
 			Valid:  takeFirst(seed.DisconnectReason.Valid, false),
 		},
 		ConnectionStatus: takeFirst(seed.ConnectionStatus, database.ConnectionStatusConnected),
+	}
+
+	var disconnectTime sql.NullTime
+	if arg.ConnectionStatus == database.ConnectionStatusDisconnected {
+		disconnectTime = sql.NullTime{Time: arg.Time, Valid: true}
+	}
+
+	err := db.BatchUpsertConnectionLogs(genCtx, database.BatchUpsertConnectionLogsParams{
+		ID:               []uuid.UUID{arg.ID},
+		ConnectTime:      []time.Time{arg.Time},
+		OrganizationID:   []uuid.UUID{arg.OrganizationID},
+		WorkspaceOwnerID: []uuid.UUID{arg.WorkspaceOwnerID},
+		WorkspaceID:      []uuid.UUID{arg.WorkspaceID},
+		WorkspaceName:    []string{arg.WorkspaceName},
+		AgentName:        []string{arg.AgentName},
+		Type:             []database.ConnectionType{arg.Type},
+		Code:             []int32{arg.Code.Int32},
+		CodeValid:        []bool{arg.Code.Valid},
+		Ip:               []pqtype.Inet{arg.IP},
+		UserAgent:        []string{arg.UserAgent.String},
+		UserID:           []uuid.UUID{arg.UserID.UUID},
+		SlugOrPort:       []string{arg.SlugOrPort.String},
+		ConnectionID:     []uuid.UUID{arg.ConnectionID.UUID},
+		DisconnectReason: []string{arg.DisconnectReason.String},
+		DisconnectTime:   []time.Time{disconnectTime.Time},
 	})
 	require.NoError(t, err, "insert connection log")
-	return log
+
+	// Query back the actual row from the database. On upsert
+	// conflict the DB keeps the original row's ID, so we can't
+	// rely on arg.ID. Match on the conflict key for rows with a
+	// connection_id, or by primary key for NULL connection_id.
+	rows, err := db.GetConnectionLogsOffset(genCtx, database.GetConnectionLogsOffsetParams{})
+	require.NoError(t, err, "query connection logs")
+	for _, row := range rows {
+		if arg.ConnectionID.Valid {
+			if row.ConnectionLog.ConnectionID == arg.ConnectionID &&
+				row.ConnectionLog.WorkspaceID == arg.WorkspaceID &&
+				row.ConnectionLog.AgentName == arg.AgentName {
+				return row.ConnectionLog
+			}
+		} else if row.ConnectionLog.ID == arg.ID {
+			return row.ConnectionLog
+		}
+	}
+	require.Failf(t, "connection log not found", "id=%s", arg.ID)
+	return database.ConnectionLog{} // unreachable
 }
 
 func Template(t testing.TB, db database.Store, seed database.Template) database.Template {
@@ -1553,6 +1597,7 @@ func UserSecret(t testing.TB, db database.Store, seed database.UserSecret) datab
 		Name:        takeFirst(seed.Name, "secret-name"),
 		Description: takeFirst(seed.Description, "secret description"),
 		Value:       takeFirst(seed.Value, "secret value"),
+		ValueKeyID:  seed.ValueKeyID,
 		EnvName:     takeFirst(seed.EnvName, "SECRET_ENV_NAME"),
 		FilePath:    takeFirst(seed.FilePath, "~/secret/file/path"),
 	})
@@ -1591,6 +1636,7 @@ func AIBridgeInterception(t testing.TB, db database.Store, seed database.InsertA
 		APIKeyID:                   seed.APIKeyID,
 		InitiatorID:                takeFirst(seed.InitiatorID, uuid.New()),
 		Provider:                   takeFirst(seed.Provider, "provider"),
+		ProviderName:               takeFirst(seed.ProviderName, "provider-name"),
 		Model:                      takeFirst(seed.Model, "model"),
 		Metadata:                   takeFirstSlice(seed.Metadata, json.RawMessage("{}")),
 		StartedAt:                  takeFirst(seed.StartedAt, dbtime.Now()),
@@ -1598,6 +1644,8 @@ func AIBridgeInterception(t testing.TB, db database.Store, seed database.InsertA
 		ThreadParentInterceptionID: seed.ThreadParentInterceptionID,
 		ThreadRootInterceptionID:   seed.ThreadRootInterceptionID,
 		ClientSessionID:            seed.ClientSessionID,
+		CredentialKind:             takeFirst(seed.CredentialKind, database.CredentialKindCentralized),
+		CredentialHint:             takeFirst(seed.CredentialHint, ""),
 	})
 	if endedAt != nil {
 		interception, err = db.UpdateAIBridgeInterceptionEnded(genCtx, database.UpdateAIBridgeInterceptionEndedParams{
@@ -1612,13 +1660,15 @@ func AIBridgeInterception(t testing.TB, db database.Store, seed database.InsertA
 
 func AIBridgeTokenUsage(t testing.TB, db database.Store, seed database.InsertAIBridgeTokenUsageParams) database.AIBridgeTokenUsage {
 	usage, err := db.InsertAIBridgeTokenUsage(genCtx, database.InsertAIBridgeTokenUsageParams{
-		ID:                 takeFirst(seed.ID, uuid.New()),
-		InterceptionID:     takeFirst(seed.InterceptionID, uuid.New()),
-		ProviderResponseID: takeFirst(seed.ProviderResponseID, "provider_response_id"),
-		InputTokens:        takeFirst(seed.InputTokens, 100),
-		OutputTokens:       takeFirst(seed.OutputTokens, 100),
-		Metadata:           takeFirstSlice(seed.Metadata, json.RawMessage("{}")),
-		CreatedAt:          takeFirst(seed.CreatedAt, dbtime.Now()),
+		ID:                    takeFirst(seed.ID, uuid.New()),
+		InterceptionID:        takeFirst(seed.InterceptionID, uuid.New()),
+		ProviderResponseID:    takeFirst(seed.ProviderResponseID, "provider_response_id"),
+		InputTokens:           takeFirst(seed.InputTokens, 100),
+		OutputTokens:          takeFirst(seed.OutputTokens, 100),
+		CacheReadInputTokens:  seed.CacheReadInputTokens,
+		CacheWriteInputTokens: seed.CacheWriteInputTokens,
+		Metadata:              takeFirstSlice(seed.Metadata, json.RawMessage("{}")),
+		CreatedAt:             takeFirst(seed.CreatedAt, dbtime.Now()),
 	})
 	require.NoError(t, err, "insert aibridge token usage")
 	return usage

coderd/database/dbmetrics/querymetrics.go

@@ -208,6 +208,14 @@ func (m queryMetricsStore) BatchUpdateWorkspaceNextStartAt(ctx context.Context,
 	return r0
 }
 
+func (m queryMetricsStore) BatchUpsertConnectionLogs(ctx context.Context, arg database.BatchUpsertConnectionLogsParams) error {
+	start := time.Now()
+	r0 := m.s.BatchUpsertConnectionLogs(ctx, arg)
+	m.queryLatencies.WithLabelValues("BatchUpsertConnectionLogs").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "BatchUpsertConnectionLogs").Inc()
+	return r0
+}
+
 func (m queryMetricsStore) BulkMarkNotificationMessagesFailed(ctx context.Context, arg database.BulkMarkNotificationMessagesFailedParams) (int64, error) {
 	start := time.Now()
 	r0, r1 := m.s.BulkMarkNotificationMessagesFailed(ctx, arg)
@@ -264,14 +272,6 @@ func (m queryMetricsStore) CleanTailnetTunnels(ctx context.Context) error {
 	return r0
 }
 
-func (m queryMetricsStore) CleanupDeletedMCPServerIDsFromChatAutomations(ctx context.Context) error {
-	start := time.Now()
-	r0 := m.s.CleanupDeletedMCPServerIDsFromChatAutomations(ctx)
-	m.queryLatencies.WithLabelValues("CleanupDeletedMCPServerIDsFromChatAutomations").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "CleanupDeletedMCPServerIDsFromChatAutomations").Inc()
-	return r0
-}
-
 func (m queryMetricsStore) CleanupDeletedMCPServerIDsFromChats(ctx context.Context) error {
 	start := time.Now()
 	r0 := m.s.CleanupDeletedMCPServerIDsFromChats(ctx)
@@ -280,6 +280,14 @@ func (m queryMetricsStore) CleanupDeletedMCPServerIDsFromChats(ctx context.Conte
 	return r0
 }
 
+func (m queryMetricsStore) ClearChatMessageProviderResponseIDsByChatID(ctx context.Context, chatID uuid.UUID) error {
+	start := time.Now()
+	r0 := m.s.ClearChatMessageProviderResponseIDsByChatID(ctx, chatID)
+	m.queryLatencies.WithLabelValues("ClearChatMessageProviderResponseIDsByChatID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "ClearChatMessageProviderResponseIDsByChatID").Inc()
+	return r0
+}
+
 func (m queryMetricsStore) CountAIBridgeInterceptions(ctx context.Context, arg database.CountAIBridgeInterceptionsParams) (int64, error) {
 	start := time.Now()
 	r0, r1 := m.s.CountAIBridgeInterceptions(ctx, arg)
@@ -304,22 +312,6 @@ func (m queryMetricsStore) CountAuditLogs(ctx context.Context, arg database.Coun
 	return r0, r1
 }
 
-func (m queryMetricsStore) CountChatAutomationChatCreatesInWindow(ctx context.Context, arg database.CountChatAutomationChatCreatesInWindowParams) (int64, error) {
-	start := time.Now()
-	r0, r1 := m.s.CountChatAutomationChatCreatesInWindow(ctx, arg)
-	m.queryLatencies.WithLabelValues("CountChatAutomationChatCreatesInWindow").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "CountChatAutomationChatCreatesInWindow").Inc()
-	return r0, r1
-}
-
-func (m queryMetricsStore) CountChatAutomationMessagesInWindow(ctx context.Context, arg database.CountChatAutomationMessagesInWindowParams) (int64, error) {
-	start := time.Now()
-	r0, r1 := m.s.CountChatAutomationMessagesInWindow(ctx, arg)
-	m.queryLatencies.WithLabelValues("CountChatAutomationMessagesInWindow").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "CountChatAutomationMessagesInWindow").Inc()
-	return r0, r1
-}
-
 func (m queryMetricsStore) CountConnectionLogs(ctx context.Context, arg database.CountConnectionLogsParams) (int64, error) {
 	start := time.Now()
 	r0, r1 := m.s.CountConnectionLogs(ctx, arg)
@@ -424,20 +416,20 @@ func (m queryMetricsStore) DeleteApplicationConnectAPIKeysByUserID(ctx context.C
 	return r0
 }
 
-func (m queryMetricsStore) DeleteChatAutomationByID(ctx context.Context, id uuid.UUID) error {
+func (m queryMetricsStore) DeleteChatDebugDataAfterMessageID(ctx context.Context, arg database.DeleteChatDebugDataAfterMessageIDParams) (int64, error) {
 	start := time.Now()
-	r0 := m.s.DeleteChatAutomationByID(ctx, id)
-	m.queryLatencies.WithLabelValues("DeleteChatAutomationByID").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "DeleteChatAutomationByID").Inc()
-	return r0
+	r0, r1 := m.s.DeleteChatDebugDataAfterMessageID(ctx, arg)
+	m.queryLatencies.WithLabelValues("DeleteChatDebugDataAfterMessageID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "DeleteChatDebugDataAfterMessageID").Inc()
+	return r0, r1
 }
 
-func (m queryMetricsStore) DeleteChatAutomationTriggerByID(ctx context.Context, id uuid.UUID) error {
+func (m queryMetricsStore) DeleteChatDebugDataByChatID(ctx context.Context, chatID uuid.UUID) (int64, error) {
 	start := time.Now()
-	r0 := m.s.DeleteChatAutomationTriggerByID(ctx, id)
-	m.queryLatencies.WithLabelValues("DeleteChatAutomationTriggerByID").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "DeleteChatAutomationTriggerByID").Inc()
-	return r0
+	r0, r1 := m.s.DeleteChatDebugDataByChatID(ctx, chatID)
+	m.queryLatencies.WithLabelValues("DeleteChatDebugDataByChatID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "DeleteChatDebugDataByChatID").Inc()
+	return r0, r1
 }
 
 func (m queryMetricsStore) DeleteChatModelConfigByID(ctx context.Context, id uuid.UUID) error {
@@ -624,6 +616,22 @@ func (m queryMetricsStore) DeleteOldAuditLogs(ctx context.Context, arg database.
 	return r0, r1
 }
 
+func (m queryMetricsStore) DeleteOldChatFiles(ctx context.Context, arg database.DeleteOldChatFilesParams) (int64, error) {
+	start := time.Now()
+	r0, r1 := m.s.DeleteOldChatFiles(ctx, arg)
+	m.queryLatencies.WithLabelValues("DeleteOldChatFiles").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "DeleteOldChatFiles").Inc()
+	return r0, r1
+}
+
+func (m queryMetricsStore) DeleteOldChats(ctx context.Context, arg database.DeleteOldChatsParams) (int64, error) {
+	start := time.Now()
+	r0, r1 := m.s.DeleteOldChats(ctx, arg)
+	m.queryLatencies.WithLabelValues("DeleteOldChats").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "DeleteOldChats").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) DeleteOldConnectionLogs(ctx context.Context, arg database.DeleteOldConnectionLogsParams) (int64, error) {
 	start := time.Now()
 	r0, r1 := m.s.DeleteOldConnectionLogs(ctx, arg)
@@ -736,14 +744,22 @@ func (m queryMetricsStore) DeleteUserChatCompactionThreshold(ctx context.Context
 	return r0
 }
 
-func (m queryMetricsStore) DeleteUserSecret(ctx context.Context, id uuid.UUID) error {
+func (m queryMetricsStore) DeleteUserChatProviderKey(ctx context.Context, arg database.DeleteUserChatProviderKeyParams) error {
 	start := time.Now()
-	r0 := m.s.DeleteUserSecret(ctx, id)
-	m.queryLatencies.WithLabelValues("DeleteUserSecret").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "DeleteUserSecret").Inc()
+	r0 := m.s.DeleteUserChatProviderKey(ctx, arg)
+	m.queryLatencies.WithLabelValues("DeleteUserChatProviderKey").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "DeleteUserChatProviderKey").Inc()
 	return r0
 }
 
+func (m queryMetricsStore) DeleteUserSecretByUserIDAndName(ctx context.Context, arg database.DeleteUserSecretByUserIDAndNameParams) (int64, error) {
+	start := time.Now()
+	r0, r1 := m.s.DeleteUserSecretByUserIDAndName(ctx, arg)
+	m.queryLatencies.WithLabelValues("DeleteUserSecretByUserIDAndName").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "DeleteUserSecretByUserIDAndName").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) DeleteWebpushSubscriptionByUserIDAndEndpoint(ctx context.Context, arg database.DeleteWebpushSubscriptionByUserIDAndEndpointParams) error {
 	start := time.Now()
 	r0 := m.s.DeleteWebpushSubscriptionByUserIDAndEndpoint(ctx, arg)
@@ -872,6 +888,14 @@ func (m queryMetricsStore) FetchVolumesResourceMonitorsUpdatedAfter(ctx context.
 	return r0, r1
 }
 
+func (m queryMetricsStore) FinalizeStaleChatDebugRows(ctx context.Context, updatedBefore time.Time) (database.FinalizeStaleChatDebugRowsRow, error) {
+	start := time.Now()
+	r0, r1 := m.s.FinalizeStaleChatDebugRows(ctx, updatedBefore)
+	m.queryLatencies.WithLabelValues("FinalizeStaleChatDebugRows").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "FinalizeStaleChatDebugRows").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) FindMatchingPresetID(ctx context.Context, arg database.FindMatchingPresetIDParams) (uuid.UUID, error) {
 	start := time.Now()
 	r0, r1 := m.s.FindMatchingPresetID(ctx, arg)
@@ -976,11 +1000,11 @@ func (m queryMetricsStore) GetActiveAISeatCount(ctx context.Context) (int64, err
 	return r0, r1
 }
 
-func (m queryMetricsStore) GetActiveChatAutomationCronTriggers(ctx context.Context) ([]database.GetActiveChatAutomationCronTriggersRow, error) {
+func (m queryMetricsStore) GetActiveChatsByAgentID(ctx context.Context, agentID uuid.UUID) ([]database.Chat, error) {
 	start := time.Now()
-	r0, r1 := m.s.GetActiveChatAutomationCronTriggers(ctx)
-	m.queryLatencies.WithLabelValues("GetActiveChatAutomationCronTriggers").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetActiveChatAutomationCronTriggers").Inc()
+	r0, r1 := m.s.GetActiveChatsByAgentID(ctx, agentID)
+	m.queryLatencies.WithLabelValues("GetActiveChatsByAgentID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetActiveChatsByAgentID").Inc()
 	return r0, r1
 }
 
@@ -1080,46 +1104,6 @@ func (m queryMetricsStore) GetAuthorizationUserRoles(ctx context.Context, userID
 	return r0, r1
 }
 
-func (m queryMetricsStore) GetChatAutomationByID(ctx context.Context, id uuid.UUID) (database.ChatAutomation, error) {
-	start := time.Now()
-	r0, r1 := m.s.GetChatAutomationByID(ctx, id)
-	m.queryLatencies.WithLabelValues("GetChatAutomationByID").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatAutomationByID").Inc()
-	return r0, r1
-}
-
-func (m queryMetricsStore) GetChatAutomationEventsByAutomationID(ctx context.Context, arg database.GetChatAutomationEventsByAutomationIDParams) ([]database.ChatAutomationEvent, error) {
-	start := time.Now()
-	r0, r1 := m.s.GetChatAutomationEventsByAutomationID(ctx, arg)
-	m.queryLatencies.WithLabelValues("GetChatAutomationEventsByAutomationID").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatAutomationEventsByAutomationID").Inc()
-	return r0, r1
-}
-
-func (m queryMetricsStore) GetChatAutomationTriggerByID(ctx context.Context, id uuid.UUID) (database.ChatAutomationTrigger, error) {
-	start := time.Now()
-	r0, r1 := m.s.GetChatAutomationTriggerByID(ctx, id)
-	m.queryLatencies.WithLabelValues("GetChatAutomationTriggerByID").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatAutomationTriggerByID").Inc()
-	return r0, r1
-}
-
-func (m queryMetricsStore) GetChatAutomationTriggersByAutomationID(ctx context.Context, automationID uuid.UUID) ([]database.ChatAutomationTrigger, error) {
-	start := time.Now()
-	r0, r1 := m.s.GetChatAutomationTriggersByAutomationID(ctx, automationID)
-	m.queryLatencies.WithLabelValues("GetChatAutomationTriggersByAutomationID").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatAutomationTriggersByAutomationID").Inc()
-	return r0, r1
-}
-
-func (m queryMetricsStore) GetChatAutomations(ctx context.Context, arg database.GetChatAutomationsParams) ([]database.ChatAutomation, error) {
-	start := time.Now()
-	r0, r1 := m.s.GetChatAutomations(ctx, arg)
-	m.queryLatencies.WithLabelValues("GetChatAutomations").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatAutomations").Inc()
-	return r0, r1
-}
-
 func (m queryMetricsStore) GetChatByID(ctx context.Context, id uuid.UUID) (database.Chat, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetChatByID(ctx, id)
@@ -1168,6 +1152,38 @@ func (m queryMetricsStore) GetChatCostSummary(ctx context.Context, arg database.
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetChatDebugLoggingAllowUsers(ctx context.Context) (bool, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatDebugLoggingAllowUsers(ctx)
+	m.queryLatencies.WithLabelValues("GetChatDebugLoggingAllowUsers").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatDebugLoggingAllowUsers").Inc()
+	return r0, r1
+}
+
+func (m queryMetricsStore) GetChatDebugRunByID(ctx context.Context, id uuid.UUID) (database.ChatDebugRun, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatDebugRunByID(ctx, id)
+	m.queryLatencies.WithLabelValues("GetChatDebugRunByID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatDebugRunByID").Inc()
+	return r0, r1
+}
+
+func (m queryMetricsStore) GetChatDebugRunsByChatID(ctx context.Context, chatID database.GetChatDebugRunsByChatIDParams) ([]database.ChatDebugRun, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatDebugRunsByChatID(ctx, chatID)
+	m.queryLatencies.WithLabelValues("GetChatDebugRunsByChatID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatDebugRunsByChatID").Inc()
+	return r0, r1
+}
+
+func (m queryMetricsStore) GetChatDebugStepsByRunID(ctx context.Context, runID uuid.UUID) ([]database.ChatDebugStep, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatDebugStepsByRunID(ctx, runID)
+	m.queryLatencies.WithLabelValues("GetChatDebugStepsByRunID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatDebugStepsByRunID").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetChatDesktopEnabled(ctx context.Context) (bool, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetChatDesktopEnabled(ctx)
@@ -1200,6 +1216,14 @@ func (m queryMetricsStore) GetChatFileByID(ctx context.Context, id uuid.UUID) (d
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetChatFileMetadataByChatID(ctx context.Context, chatID uuid.UUID) ([]database.GetChatFileMetadataByChatIDRow, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatFileMetadataByChatID(ctx, chatID)
+	m.queryLatencies.WithLabelValues("GetChatFileMetadataByChatID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatFileMetadataByChatID").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetChatFilesByIDs(ctx context.Context, ids []uuid.UUID) ([]database.ChatFile, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetChatFilesByIDs(ctx, ids)
@@ -1224,6 +1248,14 @@ func (m queryMetricsStore) GetChatMessageByID(ctx context.Context, id int64) (da
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetChatMessageSummariesPerChat(ctx context.Context, createdAfter time.Time) ([]database.GetChatMessageSummariesPerChatRow, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatMessageSummariesPerChat(ctx, createdAfter)
+	m.queryLatencies.WithLabelValues("GetChatMessageSummariesPerChat").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatMessageSummariesPerChat").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetChatMessagesByChatID(ctx context.Context, chatID database.GetChatMessagesByChatIDParams) ([]database.ChatMessage, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetChatMessagesByChatID(ctx, chatID)
@@ -1272,6 +1304,14 @@ func (m queryMetricsStore) GetChatModelConfigs(ctx context.Context) ([]database.
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetChatModelConfigsForTelemetry(ctx context.Context) ([]database.GetChatModelConfigsForTelemetryRow, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatModelConfigsForTelemetry(ctx)
+	m.queryLatencies.WithLabelValues("GetChatModelConfigsForTelemetry").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatModelConfigsForTelemetry").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetChatProviderByID(ctx context.Context, id uuid.UUID) (database.ChatProvider, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetChatProviderByID(ctx, id)
@@ -1304,6 +1344,14 @@ func (m queryMetricsStore) GetChatQueuedMessages(ctx context.Context, chatID uui
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetChatRetentionDays(ctx context.Context) (int32, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatRetentionDays(ctx)
+	m.queryLatencies.WithLabelValues("GetChatRetentionDays").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatRetentionDays").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetChatSystemPrompt(ctx context.Context) (string, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetChatSystemPrompt(ctx)
@@ -1376,6 +1424,14 @@ func (m queryMetricsStore) GetChatsByWorkspaceIDs(ctx context.Context, ids []uui
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetChatsUpdatedAfter(ctx context.Context, updatedAfter time.Time) ([]database.GetChatsUpdatedAfterRow, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatsUpdatedAfter(ctx, updatedAfter)
+	m.queryLatencies.WithLabelValues("GetChatsUpdatedAfter").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatsUpdatedAfter").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetConnectionLogsOffset(ctx context.Context, arg database.GetConnectionLogsOffsetParams) ([]database.GetConnectionLogsOffsetRow, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetConnectionLogsOffset(ctx, arg)
@@ -1992,11 +2048,11 @@ func (m queryMetricsStore) GetPRInsightsPerModel(ctx context.Context, arg databa
 	return r0, r1
 }
 
-func (m queryMetricsStore) GetPRInsightsRecentPRs(ctx context.Context, arg database.GetPRInsightsRecentPRsParams) ([]database.GetPRInsightsRecentPRsRow, error) {
+func (m queryMetricsStore) GetPRInsightsPullRequests(ctx context.Context, arg database.GetPRInsightsPullRequestsParams) ([]database.GetPRInsightsPullRequestsRow, error) {
 	start := time.Now()
-	r0, r1 := m.s.GetPRInsightsRecentPRs(ctx, arg)
-	m.queryLatencies.WithLabelValues("GetPRInsightsRecentPRs").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetPRInsightsRecentPRs").Inc()
+	r0, r1 := m.s.GetPRInsightsPullRequests(ctx, arg)
+	m.queryLatencies.WithLabelValues("GetPRInsightsPullRequests").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetPRInsightsPullRequests").Inc()
 	return r0, r1
 }
 
@@ -2296,19 +2352,19 @@ func (m queryMetricsStore) GetTailnetPeers(ctx context.Context, id uuid.UUID) ([
 	return r0, r1
 }
 
-func (m queryMetricsStore) GetTailnetTunnelPeerBindings(ctx context.Context, srcID uuid.UUID) ([]database.GetTailnetTunnelPeerBindingsRow, error) {
+func (m queryMetricsStore) GetTailnetTunnelPeerBindingsBatch(ctx context.Context, ids []uuid.UUID) ([]database.GetTailnetTunnelPeerBindingsBatchRow, error) {
 	start := time.Now()
-	r0, r1 := m.s.GetTailnetTunnelPeerBindings(ctx, srcID)
-	m.queryLatencies.WithLabelValues("GetTailnetTunnelPeerBindings").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetTailnetTunnelPeerBindings").Inc()
+	r0, r1 := m.s.GetTailnetTunnelPeerBindingsBatch(ctx, ids)
+	m.queryLatencies.WithLabelValues("GetTailnetTunnelPeerBindingsBatch").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetTailnetTunnelPeerBindingsBatch").Inc()
 	return r0, r1
 }
 
-func (m queryMetricsStore) GetTailnetTunnelPeerIDs(ctx context.Context, srcID uuid.UUID) ([]database.GetTailnetTunnelPeerIDsRow, error) {
+func (m queryMetricsStore) GetTailnetTunnelPeerIDsBatch(ctx context.Context, ids []uuid.UUID) ([]database.GetTailnetTunnelPeerIDsBatchRow, error) {
 	start := time.Now()
-	r0, r1 := m.s.GetTailnetTunnelPeerIDs(ctx, srcID)
-	m.queryLatencies.WithLabelValues("GetTailnetTunnelPeerIDs").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetTailnetTunnelPeerIDs").Inc()
+	r0, r1 := m.s.GetTailnetTunnelPeerIDsBatch(ctx, ids)
+	m.queryLatencies.WithLabelValues("GetTailnetTunnelPeerIDsBatch").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetTailnetTunnelPeerIDsBatch").Inc()
 	return r0, r1
 }
 
@@ -2616,6 +2672,22 @@ func (m queryMetricsStore) GetUserChatCustomPrompt(ctx context.Context, userID u
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetUserChatDebugLoggingEnabled(ctx context.Context, userID uuid.UUID) (bool, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetUserChatDebugLoggingEnabled(ctx, userID)
+	m.queryLatencies.WithLabelValues("GetUserChatDebugLoggingEnabled").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetUserChatDebugLoggingEnabled").Inc()
+	return r0, r1
+}
+
+func (m queryMetricsStore) GetUserChatProviderKeys(ctx context.Context, userID uuid.UUID) ([]database.UserChatProviderKey, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetUserChatProviderKeys(ctx, userID)
+	m.queryLatencies.WithLabelValues("GetUserChatProviderKeys").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetUserChatProviderKeys").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetUserChatSpendInPeriod(ctx context.Context, arg database.GetUserChatSpendInPeriodParams) (int64, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetUserChatSpendInPeriod(ctx, arg)
@@ -2680,14 +2752,6 @@ func (m queryMetricsStore) GetUserNotificationPreferences(ctx context.Context, u
 	return r0, r1
 }
 
-func (m queryMetricsStore) GetUserSecret(ctx context.Context, id uuid.UUID) (database.UserSecret, error) {
-	start := time.Now()
-	r0, r1 := m.s.GetUserSecret(ctx, id)
-	m.queryLatencies.WithLabelValues("GetUserSecret").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetUserSecret").Inc()
-	return r0, r1
-}
-
 func (m queryMetricsStore) GetUserSecretByUserIDAndName(ctx context.Context, arg database.GetUserSecretByUserIDAndNameParams) (database.UserSecret, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetUserSecretByUserIDAndName(ctx, arg)
@@ -3312,27 +3376,19 @@ func (m queryMetricsStore) InsertChat(ctx context.Context, arg database.InsertCh
 	return r0, r1
 }
 
-func (m queryMetricsStore) InsertChatAutomation(ctx context.Context, arg database.InsertChatAutomationParams) (database.ChatAutomation, error) {
+func (m queryMetricsStore) InsertChatDebugRun(ctx context.Context, arg database.InsertChatDebugRunParams) (database.ChatDebugRun, error) {
 	start := time.Now()
-	r0, r1 := m.s.InsertChatAutomation(ctx, arg)
-	m.queryLatencies.WithLabelValues("InsertChatAutomation").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "InsertChatAutomation").Inc()
+	r0, r1 := m.s.InsertChatDebugRun(ctx, arg)
+	m.queryLatencies.WithLabelValues("InsertChatDebugRun").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "InsertChatDebugRun").Inc()
 	return r0, r1
 }
 
-func (m queryMetricsStore) InsertChatAutomationEvent(ctx context.Context, arg database.InsertChatAutomationEventParams) (database.ChatAutomationEvent, error) {
+func (m queryMetricsStore) InsertChatDebugStep(ctx context.Context, arg database.InsertChatDebugStepParams) (database.ChatDebugStep, error) {
 	start := time.Now()
-	r0, r1 := m.s.InsertChatAutomationEvent(ctx, arg)
-	m.queryLatencies.WithLabelValues("InsertChatAutomationEvent").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "InsertChatAutomationEvent").Inc()
-	return r0, r1
-}
-
-func (m queryMetricsStore) InsertChatAutomationTrigger(ctx context.Context, arg database.InsertChatAutomationTriggerParams) (database.ChatAutomationTrigger, error) {
-	start := time.Now()
-	r0, r1 := m.s.InsertChatAutomationTrigger(ctx, arg)
-	m.queryLatencies.WithLabelValues("InsertChatAutomationTrigger").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "InsertChatAutomationTrigger").Inc()
+	r0, r1 := m.s.InsertChatDebugStep(ctx, arg)
+	m.queryLatencies.WithLabelValues("InsertChatDebugStep").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "InsertChatDebugStep").Inc()
 	return r0, r1
 }
 
@@ -3864,6 +3920,14 @@ func (m queryMetricsStore) InsertWorkspaceResourceMetadata(ctx context.Context,
 	return r0, r1
 }
 
+func (m queryMetricsStore) LinkChatFiles(ctx context.Context, arg database.LinkChatFilesParams) (int32, error) {
+	start := time.Now()
+	r0, r1 := m.s.LinkChatFiles(ctx, arg)
+	m.queryLatencies.WithLabelValues("LinkChatFiles").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "LinkChatFiles").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) ListAIBridgeClients(ctx context.Context, arg database.ListAIBridgeClientsParams) ([]string, error) {
 	start := time.Now()
 	r0, r1 := m.s.ListAIBridgeClients(ctx, arg)
@@ -3992,7 +4056,7 @@ func (m queryMetricsStore) ListUserChatCompactionThresholds(ctx context.Context,
 	return r0, r1
 }
 
-func (m queryMetricsStore) ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]database.UserSecret, error) {
+func (m queryMetricsStore) ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]database.ListUserSecretsRow, error) {
 	start := time.Now()
 	r0, r1 := m.s.ListUserSecrets(ctx, userID)
 	m.queryLatencies.WithLabelValues("ListUserSecrets").Observe(time.Since(start).Seconds())
@@ -4000,6 +4064,14 @@ func (m queryMetricsStore) ListUserSecrets(ctx context.Context, userID uuid.UUID
 	return r0, r1
 }
 
+func (m queryMetricsStore) ListUserSecretsWithValues(ctx context.Context, userID uuid.UUID) ([]database.UserSecret, error) {
+	start := time.Now()
+	r0, r1 := m.s.ListUserSecretsWithValues(ctx, userID)
+	m.queryLatencies.WithLabelValues("ListUserSecretsWithValues").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "ListUserSecretsWithValues").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) ListWorkspaceAgentPortShares(ctx context.Context, workspaceID uuid.UUID) ([]database.WorkspaceAgentPortShare, error) {
 	start := time.Now()
 	r0, r1 := m.s.ListWorkspaceAgentPortShares(ctx, workspaceID)
@@ -4064,14 +4136,6 @@ func (m queryMetricsStore) PopNextQueuedMessage(ctx context.Context, chatID uuid
 	return r0, r1
 }
 
-func (m queryMetricsStore) PurgeOldChatAutomationEvents(ctx context.Context, arg database.PurgeOldChatAutomationEventsParams) (int64, error) {
-	start := time.Now()
-	r0, r1 := m.s.PurgeOldChatAutomationEvents(ctx, arg)
-	m.queryLatencies.WithLabelValues("PurgeOldChatAutomationEvents").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "PurgeOldChatAutomationEvents").Inc()
-	return r0, r1
-}
-
 func (m queryMetricsStore) ReduceWorkspaceAgentShareLevelToAuthenticatedByTemplate(ctx context.Context, templateID uuid.UUID) error {
 	start := time.Now()
 	r0 := m.s.ReduceWorkspaceAgentShareLevelToAuthenticatedByTemplate(ctx, templateID)
@@ -4136,6 +4200,14 @@ func (m queryMetricsStore) SoftDeleteChatMessagesAfterID(ctx context.Context, ar
 	return r0
 }
 
+func (m queryMetricsStore) SoftDeleteContextFileMessages(ctx context.Context, chatID uuid.UUID) error {
+	start := time.Now()
+	r0 := m.s.SoftDeleteContextFileMessages(ctx, chatID)
+	m.queryLatencies.WithLabelValues("SoftDeleteContextFileMessages").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "SoftDeleteContextFileMessages").Inc()
+	return r0
+}
+
 func (m queryMetricsStore) TryAcquireLock(ctx context.Context, pgTryAdvisoryXactLock int64) (bool, error) {
 	start := time.Now()
 	r0, r1 := m.s.TryAcquireLock(ctx, pgTryAdvisoryXactLock)
@@ -4200,38 +4272,6 @@ func (m queryMetricsStore) UpdateAPIKeyByID(ctx context.Context, arg database.Up
 	return r0
 }
 
-func (m queryMetricsStore) UpdateChatAutomation(ctx context.Context, arg database.UpdateChatAutomationParams) (database.ChatAutomation, error) {
-	start := time.Now()
-	r0, r1 := m.s.UpdateChatAutomation(ctx, arg)
-	m.queryLatencies.WithLabelValues("UpdateChatAutomation").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateChatAutomation").Inc()
-	return r0, r1
-}
-
-func (m queryMetricsStore) UpdateChatAutomationTrigger(ctx context.Context, arg database.UpdateChatAutomationTriggerParams) (database.ChatAutomationTrigger, error) {
-	start := time.Now()
-	r0, r1 := m.s.UpdateChatAutomationTrigger(ctx, arg)
-	m.queryLatencies.WithLabelValues("UpdateChatAutomationTrigger").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateChatAutomationTrigger").Inc()
-	return r0, r1
-}
-
-func (m queryMetricsStore) UpdateChatAutomationTriggerLastTriggeredAt(ctx context.Context, arg database.UpdateChatAutomationTriggerLastTriggeredAtParams) error {
-	start := time.Now()
-	r0 := m.s.UpdateChatAutomationTriggerLastTriggeredAt(ctx, arg)
-	m.queryLatencies.WithLabelValues("UpdateChatAutomationTriggerLastTriggeredAt").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateChatAutomationTriggerLastTriggeredAt").Inc()
-	return r0
-}
-
-func (m queryMetricsStore) UpdateChatAutomationTriggerWebhookSecret(ctx context.Context, arg database.UpdateChatAutomationTriggerWebhookSecretParams) (database.ChatAutomationTrigger, error) {
-	start := time.Now()
-	r0, r1 := m.s.UpdateChatAutomationTriggerWebhookSecret(ctx, arg)
-	m.queryLatencies.WithLabelValues("UpdateChatAutomationTriggerWebhookSecret").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateChatAutomationTriggerWebhookSecret").Inc()
-	return r0, r1
-}
-
 func (m queryMetricsStore) UpdateChatBuildAgentBinding(ctx context.Context, arg database.UpdateChatBuildAgentBindingParams) (database.Chat, error) {
 	start := time.Now()
 	r0, r1 := m.s.UpdateChatBuildAgentBinding(ctx, arg)
@@ -4248,11 +4288,27 @@ func (m queryMetricsStore) UpdateChatByID(ctx context.Context, arg database.Upda
 	return r0, r1
 }
 
-func (m queryMetricsStore) UpdateChatHeartbeat(ctx context.Context, arg database.UpdateChatHeartbeatParams) (int64, error) {
+func (m queryMetricsStore) UpdateChatDebugRun(ctx context.Context, arg database.UpdateChatDebugRunParams) (database.ChatDebugRun, error) {
 	start := time.Now()
-	r0, r1 := m.s.UpdateChatHeartbeat(ctx, arg)
-	m.queryLatencies.WithLabelValues("UpdateChatHeartbeat").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateChatHeartbeat").Inc()
+	r0, r1 := m.s.UpdateChatDebugRun(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpdateChatDebugRun").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateChatDebugRun").Inc()
+	return r0, r1
+}
+
+func (m queryMetricsStore) UpdateChatDebugStep(ctx context.Context, arg database.UpdateChatDebugStepParams) (database.ChatDebugStep, error) {
+	start := time.Now()
+	r0, r1 := m.s.UpdateChatDebugStep(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpdateChatDebugStep").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateChatDebugStep").Inc()
+	return r0, r1
+}
+
+func (m queryMetricsStore) UpdateChatHeartbeats(ctx context.Context, arg database.UpdateChatHeartbeatsParams) ([]uuid.UUID, error) {
+	start := time.Now()
+	r0, r1 := m.s.UpdateChatHeartbeats(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpdateChatHeartbeats").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateChatHeartbeats").Inc()
 	return r0, r1
 }
 
@@ -4712,6 +4768,14 @@ func (m queryMetricsStore) UpdateUserChatCustomPrompt(ctx context.Context, arg d
 	return r0, r1
 }
 
+func (m queryMetricsStore) UpdateUserChatProviderKey(ctx context.Context, arg database.UpdateUserChatProviderKeyParams) (database.UserChatProviderKey, error) {
+	start := time.Now()
+	r0, r1 := m.s.UpdateUserChatProviderKey(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpdateUserChatProviderKey").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateUserChatProviderKey").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) UpdateUserDeletedByID(ctx context.Context, id uuid.UUID) error {
 	start := time.Now()
 	r0 := m.s.UpdateUserDeletedByID(ctx, id)
@@ -4800,11 +4864,11 @@ func (m queryMetricsStore) UpdateUserRoles(ctx context.Context, arg database.Upd
 	return r0, r1
 }
 
-func (m queryMetricsStore) UpdateUserSecret(ctx context.Context, arg database.UpdateUserSecretParams) (database.UserSecret, error) {
+func (m queryMetricsStore) UpdateUserSecretByUserIDAndName(ctx context.Context, arg database.UpdateUserSecretByUserIDAndNameParams) (database.UserSecret, error) {
 	start := time.Now()
-	r0, r1 := m.s.UpdateUserSecret(ctx, arg)
-	m.queryLatencies.WithLabelValues("UpdateUserSecret").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateUserSecret").Inc()
+	r0, r1 := m.s.UpdateUserSecretByUserIDAndName(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpdateUserSecretByUserIDAndName").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateUserSecretByUserIDAndName").Inc()
 	return r0, r1
 }
 
@@ -4872,6 +4936,14 @@ func (m queryMetricsStore) UpdateWorkspaceAgentConnectionByID(ctx context.Contex
 	return r0
 }
 
+func (m queryMetricsStore) UpdateWorkspaceAgentDirectoryByID(ctx context.Context, arg database.UpdateWorkspaceAgentDirectoryByIDParams) error {
+	start := time.Now()
+	r0 := m.s.UpdateWorkspaceAgentDirectoryByID(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpdateWorkspaceAgentDirectoryByID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateWorkspaceAgentDirectoryByID").Inc()
+	return r0
+}
+
 func (m queryMetricsStore) UpdateWorkspaceAgentDisplayAppsByID(ctx context.Context, arg database.UpdateWorkspaceAgentDisplayAppsByIDParams) error {
 	start := time.Now()
 	r0 := m.s.UpdateWorkspaceAgentDisplayAppsByID(ctx, arg)
@@ -5072,6 +5144,14 @@ func (m queryMetricsStore) UpsertBoundaryUsageStats(ctx context.Context, arg dat
 	return r0, r1
 }
 
+func (m queryMetricsStore) UpsertChatDebugLoggingAllowUsers(ctx context.Context, allowUsers bool) error {
+	start := time.Now()
+	r0 := m.s.UpsertChatDebugLoggingAllowUsers(ctx, allowUsers)
+	m.queryLatencies.WithLabelValues("UpsertChatDebugLoggingAllowUsers").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpsertChatDebugLoggingAllowUsers").Inc()
+	return r0
+}
+
 func (m queryMetricsStore) UpsertChatDesktopEnabled(ctx context.Context, enableDesktop bool) error {
 	start := time.Now()
 	r0 := m.s.UpsertChatDesktopEnabled(ctx, enableDesktop)
@@ -5104,6 +5184,14 @@ func (m queryMetricsStore) UpsertChatIncludeDefaultSystemPrompt(ctx context.Cont
 	return r0
 }
 
+func (m queryMetricsStore) UpsertChatRetentionDays(ctx context.Context, retentionDays int32) error {
+	start := time.Now()
+	r0 := m.s.UpsertChatRetentionDays(ctx, retentionDays)
+	m.queryLatencies.WithLabelValues("UpsertChatRetentionDays").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpsertChatRetentionDays").Inc()
+	return r0
+}
+
 func (m queryMetricsStore) UpsertChatSystemPrompt(ctx context.Context, value string) error {
 	start := time.Now()
 	r0 := m.s.UpsertChatSystemPrompt(ctx, value)
@@ -5152,14 +5240,6 @@ func (m queryMetricsStore) UpsertChatWorkspaceTTL(ctx context.Context, workspace
 	return r0
 }
 
-func (m queryMetricsStore) UpsertConnectionLog(ctx context.Context, arg database.UpsertConnectionLogParams) (database.ConnectionLog, error) {
-	start := time.Now()
-	r0, r1 := m.s.UpsertConnectionLog(ctx, arg)
-	m.queryLatencies.WithLabelValues("UpsertConnectionLog").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpsertConnectionLog").Inc()
-	return r0, r1
-}
-
 func (m queryMetricsStore) UpsertDefaultProxy(ctx context.Context, arg database.UpsertDefaultProxyParams) error {
 	start := time.Now()
 	r0 := m.s.UpsertDefaultProxy(ctx, arg)
@@ -5304,6 +5384,22 @@ func (m queryMetricsStore) UpsertTemplateUsageStats(ctx context.Context) error {
 	return r0
 }
 
+func (m queryMetricsStore) UpsertUserChatDebugLoggingEnabled(ctx context.Context, arg database.UpsertUserChatDebugLoggingEnabledParams) error {
+	start := time.Now()
+	r0 := m.s.UpsertUserChatDebugLoggingEnabled(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpsertUserChatDebugLoggingEnabled").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpsertUserChatDebugLoggingEnabled").Inc()
+	return r0
+}
+
+func (m queryMetricsStore) UpsertUserChatProviderKey(ctx context.Context, arg database.UpsertUserChatProviderKeyParams) (database.UserChatProviderKey, error) {
+	start := time.Now()
+	r0, r1 := m.s.UpsertUserChatProviderKey(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpsertUserChatProviderKey").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpsertUserChatProviderKey").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) UpsertWebpushVAPIDKeys(ctx context.Context, arg database.UpsertWebpushVAPIDKeysParams) error {
 	start := time.Now()
 	r0 := m.s.UpsertWebpushVAPIDKeys(ctx, arg)
@@ -5503,11 +5599,3 @@ func (m queryMetricsStore) GetAuthorizedChats(ctx context.Context, arg database.
 	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetAuthorizedChats").Inc()
 	return r0, r1
 }
-
-func (m queryMetricsStore) GetAuthorizedChatAutomations(ctx context.Context, arg database.GetChatAutomationsParams, prepared rbac.PreparedAuthorized) ([]database.ChatAutomation, error) {
-	start := time.Now()
-	r0, r1 := m.s.GetAuthorizedChatAutomations(ctx, arg, prepared)
-	m.queryLatencies.WithLabelValues("GetAuthorizedChatAutomations").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetAuthorizedChatAutomations").Inc()
-	return r0, r1
-}

coderd/database/dbpurge/dbpurge.go

@@ -34,6 +34,11 @@ const (
 	// long enough to cover the maximum interval of a heartbeat event (currently
 	// 1 hour) plus some buffer.
 	maxTelemetryHeartbeatAge = 24 * time.Hour
+	// Batch sizes for chat purging. Both use 1000, which is smaller
+	// than audit/connection log batches (10000), because chat_files
+	// rows contain bytea blob data that make large batches heavier.
+	chatsBatchSize     = 1000
+	chatFilesBatchSize = 1000
 )
 
 // New creates a new periodically purging database instance.
@@ -109,6 +114,17 @@ func New(ctx context.Context, logger slog.Logger, db database.Store, vals *coder
 // purgeTick performs a single purge iteration. It returns an error if the
 // purge fails.
 func (i *instance) purgeTick(ctx context.Context, db database.Store, start time.Time) error {
+	// Read chat retention config outside the transaction to
+	// avoid poisoning the tx if the stored value is corrupt.
+	// A SQL-level cast error (e.g. non-numeric text) puts PG
+	// into error state, failing all subsequent queries in the
+	// same transaction.
+	chatRetentionDays, err := db.GetChatRetentionDays(ctx)
+	if err != nil {
+		i.logger.Warn(ctx, "failed to read chat retention config, skipping chat purge", slog.Error(err))
+		chatRetentionDays = 0
+	}
+
 	// Start a transaction to grab advisory lock, we don't want to run
 	// multiple purges at the same time (multiple replicas).
 	return db.InTx(func(tx database.Store) error {
@@ -213,12 +229,43 @@ func (i *instance) purgeTick(ctx context.Context, db database.Store, start time.
 			}
 		}
 
+		// Chat retention is configured via site_configs. When
+		// enabled, old archived chats are deleted first, then
+		// orphaned chat files. Deleting a chat cascades to
+		// chat_file_links (removing references) but not to
+		// chat_files directly, so files from deleted chats
+		// become orphaned and are caught by DeleteOldChatFiles
+		// in the same tick.
+		var purgedChats int64
+		var purgedChatFiles int64
+		if chatRetentionDays > 0 {
+			chatRetention := time.Duration(chatRetentionDays) * 24 * time.Hour
+			deleteChatsBefore := start.Add(-chatRetention)
+
+			purgedChats, err = tx.DeleteOldChats(ctx, database.DeleteOldChatsParams{
+				BeforeTime: deleteChatsBefore,
+				LimitCount: chatsBatchSize,
+			})
+			if err != nil {
+				return xerrors.Errorf("failed to delete old chats: %w", err)
+			}
+
+			purgedChatFiles, err = tx.DeleteOldChatFiles(ctx, database.DeleteOldChatFilesParams{
+				BeforeTime: deleteChatsBefore,
+				LimitCount: chatFilesBatchSize,
+			})
+			if err != nil {
+				return xerrors.Errorf("failed to delete old chat files: %w", err)
+			}
+		}
 		i.logger.Debug(ctx, "purged old database entries",
 			slog.F("workspace_agent_logs", purgedWorkspaceAgentLogs),
 			slog.F("expired_api_keys", expiredAPIKeys),
 			slog.F("aibridge_records", purgedAIBridgeRecords),
 			slog.F("connection_logs", purgedConnectionLogs),
 			slog.F("audit_logs", purgedAuditLogs),
+			slog.F("chats", purgedChats),
+			slog.F("chat_files", purgedChatFiles),
 			slog.F("duration", i.clk.Since(start)),
 		)
 
@@ -232,6 +279,8 @@ func (i *instance) purgeTick(ctx context.Context, db database.Store, start time.
 			i.recordsPurged.WithLabelValues("aibridge_records").Add(float64(purgedAIBridgeRecords))
 			i.recordsPurged.WithLabelValues("connection_logs").Add(float64(purgedConnectionLogs))
 			i.recordsPurged.WithLabelValues("audit_logs").Add(float64(purgedAuditLogs))
+			i.recordsPurged.WithLabelValues("chats").Add(float64(purgedChats))
+			i.recordsPurged.WithLabelValues("chat_files").Add(float64(purgedChatFiles))
 		}
 
 		return nil

coderd/database/dbpurge/dbpurge_test.go

@@ -12,6 +12,7 @@ import (
 	"time"
 
 	"github.com/google/uuid"
+	"github.com/lib/pq"
 	"github.com/prometheus/client_golang/prometheus"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
@@ -53,6 +54,7 @@ func TestPurge(t *testing.T) {
 	clk := quartz.NewMock(t)
 	done := awaitDoTick(ctx, t, clk)
 	mDB := dbmock.NewMockStore(gomock.NewController(t))
+	mDB.EXPECT().GetChatRetentionDays(gomock.Any()).Return(int32(0), nil).AnyTimes()
 	mDB.EXPECT().InTx(gomock.Any(), database.DefaultTXOptions().WithID("db_purge")).Return(nil).Times(2)
 	purger := dbpurge.New(context.Background(), testutil.Logger(t), mDB, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry())
 	<-done // wait for doTick() to run.
@@ -125,6 +127,16 @@ func TestMetrics(t *testing.T) {
 			"record_type": "audit_logs",
 		})
 		require.GreaterOrEqual(t, auditLogs, 0)
+
+		chats := promhelp.CounterValue(t, reg, "coderd_dbpurge_records_purged_total", prometheus.Labels{
+			"record_type": "chats",
+		})
+		require.GreaterOrEqual(t, chats, 0)
+
+		chatFiles := promhelp.CounterValue(t, reg, "coderd_dbpurge_records_purged_total", prometheus.Labels{
+			"record_type": "chat_files",
+		})
+		require.GreaterOrEqual(t, chatFiles, 0)
 	})
 
 	t.Run("FailedIteration", func(t *testing.T) {
@@ -138,6 +150,7 @@ func TestMetrics(t *testing.T) {
 
 		ctrl := gomock.NewController(t)
 		mDB := dbmock.NewMockStore(ctrl)
+		mDB.EXPECT().GetChatRetentionDays(gomock.Any()).Return(int32(0), nil).AnyTimes()
 		mDB.EXPECT().InTx(gomock.Any(), database.DefaultTXOptions().WithID("db_purge")).
 			Return(xerrors.New("simulated database error")).
 			MinTimes(1)
@@ -1634,3 +1647,488 @@ func TestDeleteExpiredAPIKeys(t *testing.T) {
 func ptr[T any](v T) *T {
 	return &v
 }
+
+//nolint:paralleltest // It uses LockIDDBPurge.
+func TestDeleteOldChatFiles(t *testing.T) {
+	now := time.Date(2025, 6, 15, 12, 0, 0, 0, time.UTC)
+
+	// createChatFile inserts a chat file and backdates created_at.
+	createChatFile := func(ctx context.Context, t *testing.T, db database.Store, rawDB *sql.DB, ownerID, orgID uuid.UUID, createdAt time.Time) uuid.UUID {
+		t.Helper()
+		row, err := db.InsertChatFile(ctx, database.InsertChatFileParams{
+			OwnerID:        ownerID,
+			OrganizationID: orgID,
+			Name:           "test.png",
+			Mimetype:       "image/png",
+			Data:           []byte("fake-image-data"),
+		})
+		require.NoError(t, err)
+		_, err = rawDB.ExecContext(ctx, "UPDATE chat_files SET created_at = $1 WHERE id = $2", createdAt, row.ID)
+		require.NoError(t, err)
+		return row.ID
+	}
+
+	// createChat inserts a chat and optionally archives it, then
+	// backdates updated_at to control the "archived since" window.
+	createChat := func(ctx context.Context, t *testing.T, db database.Store, rawDB *sql.DB, ownerID, modelConfigID uuid.UUID, archived bool, updatedAt time.Time) database.Chat {
+		t.Helper()
+		chat, err := db.InsertChat(ctx, database.InsertChatParams{
+			OwnerID:           ownerID,
+			LastModelConfigID: modelConfigID,
+			Title:             "test-chat",
+			Status:            database.ChatStatusWaiting,
+		})
+		require.NoError(t, err)
+		if archived {
+			_, err = db.ArchiveChatByID(ctx, chat.ID)
+			require.NoError(t, err)
+		}
+		_, err = rawDB.ExecContext(ctx, "UPDATE chats SET updated_at = $1 WHERE id = $2", updatedAt, chat.ID)
+		require.NoError(t, err)
+		return chat
+	}
+	// setupChatDeps creates the common dependencies needed for
+	// chat-related tests: user, org, org member, provider, model config.
+	type chatDeps struct {
+		user        database.User
+		org         database.Organization
+		modelConfig database.ChatModelConfig
+	}
+	setupChatDeps := func(ctx context.Context, t *testing.T, db database.Store) chatDeps {
+		t.Helper()
+		user := dbgen.User(t, db, database.User{})
+		org := dbgen.Organization(t, db, database.Organization{})
+		_ = dbgen.OrganizationMember(t, db, database.OrganizationMember{UserID: user.ID, OrganizationID: org.ID})
+		_, err := db.InsertChatProvider(ctx, database.InsertChatProviderParams{
+			Provider:             "openai",
+			DisplayName:          "OpenAI",
+			Enabled:              true,
+			CentralApiKeyEnabled: true,
+		})
+		require.NoError(t, err)
+		mc, err := db.InsertChatModelConfig(ctx, database.InsertChatModelConfigParams{
+			Provider:     "openai",
+			Model:        "test-model",
+			ContextLimit: 8192,
+			Options:      json.RawMessage("{}"),
+		})
+		require.NoError(t, err)
+		return chatDeps{user: user, org: org, modelConfig: mc}
+	}
+
+	tests := []struct {
+		name string
+		run  func(t *testing.T)
+	}{
+		{
+			name: "ChatRetentionDisabled",
+			run: func(t *testing.T) {
+				ctx := testutil.Context(t, testutil.WaitLong)
+				clk := quartz.NewMock(t)
+				clk.Set(now).MustWait(ctx)
+
+				db, _, rawDB := dbtestutil.NewDBWithSQLDB(t, dbtestutil.WithDumpOnFailure())
+				logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+				deps := setupChatDeps(ctx, t, db)
+
+				// Disable retention.
+				err := db.UpsertChatRetentionDays(ctx, int32(0))
+				require.NoError(t, err)
+
+				// Create an old archived chat and an orphaned old file.
+				oldChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, true, now.Add(-31*24*time.Hour))
+				oldFileID := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-31*24*time.Hour))
+
+				done := awaitDoTick(ctx, t, clk)
+				closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry())
+				defer closer.Close()
+				testutil.TryReceive(ctx, t, done)
+
+				// Both should still exist.
+				_, err = db.GetChatByID(ctx, oldChat.ID)
+				require.NoError(t, err, "chat should not be deleted when retention is disabled")
+				_, err = db.GetChatFileByID(ctx, oldFileID)
+				require.NoError(t, err, "chat file should not be deleted when retention is disabled")
+			},
+		},
+		{
+			name: "OldArchivedChatsDeleted",
+			run: func(t *testing.T) {
+				ctx := testutil.Context(t, testutil.WaitLong)
+				clk := quartz.NewMock(t)
+				clk.Set(now).MustWait(ctx)
+
+				db, _, rawDB := dbtestutil.NewDBWithSQLDB(t, dbtestutil.WithDumpOnFailure())
+				logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+				deps := setupChatDeps(ctx, t, db)
+
+				err := db.UpsertChatRetentionDays(ctx, int32(30))
+				require.NoError(t, err)
+
+				// Old archived chat (31 days) — should be deleted.
+				oldChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, true, now.Add(-31*24*time.Hour))
+				// Insert a message so we can verify CASCADE.
+				_, err = db.InsertChatMessages(ctx, database.InsertChatMessagesParams{
+					ChatID:              oldChat.ID,
+					CreatedBy:           []uuid.UUID{deps.user.ID},
+					ModelConfigID:       []uuid.UUID{deps.modelConfig.ID},
+					Role:                []database.ChatMessageRole{database.ChatMessageRoleUser},
+					Content:             []string{`[{"type":"text","text":"hello"}]`},
+					ContentVersion:      []int16{0},
+					Visibility:          []database.ChatMessageVisibility{database.ChatMessageVisibilityBoth},
+					InputTokens:         []int64{0},
+					OutputTokens:        []int64{0},
+					TotalTokens:         []int64{0},
+					ReasoningTokens:     []int64{0},
+					CacheCreationTokens: []int64{0},
+					CacheReadTokens:     []int64{0},
+					ContextLimit:        []int64{0},
+					Compressed:          []bool{false},
+					TotalCostMicros:     []int64{0},
+					RuntimeMs:           []int64{0},
+					ProviderResponseID:  []string{""},
+				})
+				require.NoError(t, err)
+
+				// Recently archived chat (10 days) — should be retained.
+				recentChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, true, now.Add(-10*24*time.Hour))
+
+				// Active chat — should be retained.
+				activeChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, false, now)
+
+				done := awaitDoTick(ctx, t, clk)
+				closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry())
+				defer closer.Close()
+				testutil.TryReceive(ctx, t, done)
+
+				// Old archived chat should be gone.
+				_, err = db.GetChatByID(ctx, oldChat.ID)
+				require.Error(t, err, "old archived chat should be deleted")
+
+				// Its messages should be gone too (CASCADE).
+				msgs, err := db.GetChatMessagesByChatID(ctx, database.GetChatMessagesByChatIDParams{
+					ChatID:  oldChat.ID,
+					AfterID: 0,
+				})
+				require.NoError(t, err)
+				require.Empty(t, msgs, "messages should be cascade-deleted")
+
+				// Recent archived and active chats should remain.
+				_, err = db.GetChatByID(ctx, recentChat.ID)
+				require.NoError(t, err, "recently archived chat should be retained")
+				_, err = db.GetChatByID(ctx, activeChat.ID)
+				require.NoError(t, err, "active chat should be retained")
+			},
+		},
+		{
+			name: "OrphanedOldFilesDeleted",
+			run: func(t *testing.T) {
+				ctx := testutil.Context(t, testutil.WaitLong)
+				clk := quartz.NewMock(t)
+				clk.Set(now).MustWait(ctx)
+
+				db, _, rawDB := dbtestutil.NewDBWithSQLDB(t, dbtestutil.WithDumpOnFailure())
+				logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+				deps := setupChatDeps(ctx, t, db)
+
+				err := db.UpsertChatRetentionDays(ctx, int32(30))
+				require.NoError(t, err)
+
+				// File A: 31 days old, NOT in any chat -> should be deleted.
+				fileA := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-31*24*time.Hour))
+
+				// File B: 31 days old, in an active chat -> should be retained.
+				fileB := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-31*24*time.Hour))
+				activeChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, false, now)
+				_, err = db.LinkChatFiles(ctx, database.LinkChatFilesParams{
+					ChatID:       activeChat.ID,
+					MaxFileLinks: 100,
+					FileIds:      []uuid.UUID{fileB},
+				})
+				require.NoError(t, err)
+
+				// File C: 10 days old, NOT in any chat -> should be retained (too young).
+				fileC := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-10*24*time.Hour))
+
+				// File near boundary: 29d23h old — close to threshold.
+				fileBoundary := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-30*24*time.Hour).Add(time.Hour))
+
+				done := awaitDoTick(ctx, t, clk)
+				closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry())
+				defer closer.Close()
+				testutil.TryReceive(ctx, t, done)
+
+				_, err = db.GetChatFileByID(ctx, fileA)
+				require.Error(t, err, "orphaned old file A should be deleted")
+
+				_, err = db.GetChatFileByID(ctx, fileB)
+				require.NoError(t, err, "file B in active chat should be retained")
+
+				_, err = db.GetChatFileByID(ctx, fileC)
+				require.NoError(t, err, "young file C should be retained")
+
+				_, err = db.GetChatFileByID(ctx, fileBoundary)
+				require.NoError(t, err, "file near 30d boundary should be retained")
+			},
+		},
+		{
+			name: "ArchivedChatFilesDeleted",
+			run: func(t *testing.T) {
+				ctx := testutil.Context(t, testutil.WaitLong)
+				clk := quartz.NewMock(t)
+				clk.Set(now).MustWait(ctx)
+
+				db, _, rawDB := dbtestutil.NewDBWithSQLDB(t, dbtestutil.WithDumpOnFailure())
+				logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+				deps := setupChatDeps(ctx, t, db)
+
+				err := db.UpsertChatRetentionDays(ctx, int32(30))
+				require.NoError(t, err)
+
+				// File D: 31 days old, in a chat archived 31 days ago -> should be deleted.
+				fileD := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-31*24*time.Hour))
+				oldArchivedChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, true, now.Add(-31*24*time.Hour))
+				_, err = db.LinkChatFiles(ctx, database.LinkChatFilesParams{
+					ChatID:       oldArchivedChat.ID,
+					MaxFileLinks: 100,
+					FileIds:      []uuid.UUID{fileD},
+				})
+				require.NoError(t, err)
+				// LinkChatFiles does not update chats.updated_at, so backdate.
+				_, err = rawDB.ExecContext(ctx, "UPDATE chats SET updated_at = $1 WHERE id = $2",
+					now.Add(-31*24*time.Hour), oldArchivedChat.ID)
+				require.NoError(t, err)
+
+				// File E: 31 days old, in a chat archived 10 days ago -> should be retained.
+				fileE := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-31*24*time.Hour))
+				recentArchivedChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, true, now.Add(-10*24*time.Hour))
+				_, err = db.LinkChatFiles(ctx, database.LinkChatFilesParams{
+					ChatID:       recentArchivedChat.ID,
+					MaxFileLinks: 100,
+					FileIds:      []uuid.UUID{fileE},
+				})
+				require.NoError(t, err)
+				_, err = rawDB.ExecContext(ctx, "UPDATE chats SET updated_at = $1 WHERE id = $2",
+					now.Add(-10*24*time.Hour), recentArchivedChat.ID)
+				require.NoError(t, err)
+
+				// File F: 31 days old, in BOTH an active chat AND an old archived chat -> should be retained.
+				fileF := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-31*24*time.Hour))
+				anotherOldArchivedChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, true, now.Add(-31*24*time.Hour))
+				_, err = db.LinkChatFiles(ctx, database.LinkChatFilesParams{
+					ChatID:       anotherOldArchivedChat.ID,
+					MaxFileLinks: 100,
+					FileIds:      []uuid.UUID{fileF},
+				})
+				require.NoError(t, err)
+				_, err = rawDB.ExecContext(ctx, "UPDATE chats SET updated_at = $1 WHERE id = $2",
+					now.Add(-31*24*time.Hour), anotherOldArchivedChat.ID)
+				require.NoError(t, err)
+
+				activeChatForF := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, false, now)
+				_, err = db.LinkChatFiles(ctx, database.LinkChatFilesParams{
+					ChatID:       activeChatForF.ID,
+					MaxFileLinks: 100,
+					FileIds:      []uuid.UUID{fileF},
+				})
+				require.NoError(t, err)
+
+				done := awaitDoTick(ctx, t, clk)
+				closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry())
+				defer closer.Close()
+				testutil.TryReceive(ctx, t, done)
+
+				_, err = db.GetChatFileByID(ctx, fileD)
+				require.Error(t, err, "file D in old archived chat should be deleted")
+
+				_, err = db.GetChatFileByID(ctx, fileE)
+				require.NoError(t, err, "file E in recently archived chat should be retained")
+
+				_, err = db.GetChatFileByID(ctx, fileF)
+				require.NoError(t, err, "file F in active + old archived chat should be retained")
+			},
+		},
+		{
+			name: "UnarchiveAfterFilePurge",
+			run: func(t *testing.T) {
+				// Validates that when dbpurge deletes chat_files rows,
+				// the FK cascade on chat_file_links automatically
+				// removes the stale links. Unarchiving a chat after
+				// file purge should show only surviving files.
+				ctx := testutil.Context(t, testutil.WaitLong)
+				db, _, rawDB := dbtestutil.NewDBWithSQLDB(t, dbtestutil.WithDumpOnFailure())
+				deps := setupChatDeps(ctx, t, db)
+
+				// Create a chat with three attached files.
+				fileA := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now)
+				fileB := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now)
+				fileC := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now)
+
+				chat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, false, now)
+				_, err := db.LinkChatFiles(ctx, database.LinkChatFilesParams{
+					ChatID:       chat.ID,
+					MaxFileLinks: 100,
+					FileIds:      []uuid.UUID{fileA, fileB, fileC},
+				})
+				require.NoError(t, err)
+
+				// Archive the chat.
+				_, err = db.ArchiveChatByID(ctx, chat.ID)
+				require.NoError(t, err)
+
+				// Simulate dbpurge deleting files A and B. The FK
+				// cascade on chat_file_links_file_id_fkey should
+				// automatically remove the corresponding link rows.
+				_, err = rawDB.ExecContext(ctx, "DELETE FROM chat_files WHERE id = ANY($1)", pq.Array([]uuid.UUID{fileA, fileB}))
+				require.NoError(t, err)
+
+				// Unarchive the chat.
+				_, err = db.UnarchiveChatByID(ctx, chat.ID)
+				require.NoError(t, err)
+
+				// Only file C should remain linked (FK cascade
+				// removed the links for deleted files A and B).
+				files, err := db.GetChatFileMetadataByChatID(ctx, chat.ID)
+				require.NoError(t, err)
+				require.Len(t, files, 1, "only surviving file should be linked")
+				require.Equal(t, fileC, files[0].ID)
+
+				// Edge case: delete the last file too. The chat
+				// should have zero linked files, not an error.
+				_, err = db.ArchiveChatByID(ctx, chat.ID)
+				require.NoError(t, err)
+				_, err = rawDB.ExecContext(ctx, "DELETE FROM chat_files WHERE id = $1", fileC)
+				require.NoError(t, err)
+				_, err = db.UnarchiveChatByID(ctx, chat.ID)
+				require.NoError(t, err)
+
+				files, err = db.GetChatFileMetadataByChatID(ctx, chat.ID)
+				require.NoError(t, err)
+				require.Empty(t, files, "all-files-deleted should yield empty result")
+
+				// Test parent+child cascade: deleting files should
+				// clean up links for both parent and child chats
+				// independently via FK cascade.
+				parentChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, false, now)
+				childChat, err := db.InsertChat(ctx, database.InsertChatParams{
+					OwnerID:           deps.user.ID,
+					LastModelConfigID: deps.modelConfig.ID,
+					Title:             "child-chat",
+					Status:            database.ChatStatusWaiting,
+				})
+				require.NoError(t, err)
+				// Set root_chat_id to link child to parent.
+				_, err = rawDB.ExecContext(ctx, "UPDATE chats SET root_chat_id = $1 WHERE id = $2", parentChat.ID, childChat.ID)
+				require.NoError(t, err)
+
+				// Attach different files to parent and child.
+				parentFileKeep := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now)
+				parentFileStale := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now)
+				childFileKeep := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now)
+				childFileStale := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now)
+
+				_, err = db.LinkChatFiles(ctx, database.LinkChatFilesParams{
+					ChatID:       parentChat.ID,
+					MaxFileLinks: 100,
+					FileIds:      []uuid.UUID{parentFileKeep, parentFileStale},
+				})
+				require.NoError(t, err)
+				_, err = db.LinkChatFiles(ctx, database.LinkChatFilesParams{
+					ChatID:       childChat.ID,
+					MaxFileLinks: 100,
+					FileIds:      []uuid.UUID{childFileKeep, childFileStale},
+				})
+				require.NoError(t, err)
+
+				// Archive via parent (cascades to child).
+				_, err = db.ArchiveChatByID(ctx, parentChat.ID)
+				require.NoError(t, err)
+
+				// Delete one file from each chat.
+				_, err = rawDB.ExecContext(ctx, "DELETE FROM chat_files WHERE id = ANY($1)",
+					pq.Array([]uuid.UUID{parentFileStale, childFileStale}))
+				require.NoError(t, err)
+
+				// Unarchive via parent.
+				_, err = db.UnarchiveChatByID(ctx, parentChat.ID)
+				require.NoError(t, err)
+
+				parentFiles, err := db.GetChatFileMetadataByChatID(ctx, parentChat.ID)
+				require.NoError(t, err)
+				require.Len(t, parentFiles, 1)
+				require.Equal(t, parentFileKeep, parentFiles[0].ID,
+					"parent should retain only non-stale file")
+
+				childFiles, err := db.GetChatFileMetadataByChatID(ctx, childChat.ID)
+				require.NoError(t, err)
+				require.Len(t, childFiles, 1)
+				require.Equal(t, childFileKeep, childFiles[0].ID,
+					"child should retain only non-stale file")
+			},
+		},
+		{
+			name: "BatchLimitFiles",
+			run: func(t *testing.T) {
+				ctx := testutil.Context(t, testutil.WaitLong)
+				db, _, rawDB := dbtestutil.NewDBWithSQLDB(t, dbtestutil.WithDumpOnFailure())
+				deps := setupChatDeps(ctx, t, db)
+
+				// Create 3 deletable orphaned files (all 31 days old).
+				for range 3 {
+					createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-31*24*time.Hour))
+				}
+
+				// Delete with limit 2 — should delete 2, leave 1.
+				deleted, err := db.DeleteOldChatFiles(ctx, database.DeleteOldChatFilesParams{
+					BeforeTime: now.Add(-30 * 24 * time.Hour),
+					LimitCount: 2,
+				})
+				require.NoError(t, err)
+				require.Equal(t, int64(2), deleted, "should delete exactly 2 files")
+
+				// Delete again — should delete the remaining 1.
+				deleted, err = db.DeleteOldChatFiles(ctx, database.DeleteOldChatFilesParams{
+					BeforeTime: now.Add(-30 * 24 * time.Hour),
+					LimitCount: 2,
+				})
+				require.NoError(t, err)
+				require.Equal(t, int64(1), deleted, "should delete remaining 1 file")
+			},
+		},
+		{
+			name: "BatchLimitChats",
+			run: func(t *testing.T) {
+				ctx := testutil.Context(t, testutil.WaitLong)
+				db, _, rawDB := dbtestutil.NewDBWithSQLDB(t, dbtestutil.WithDumpOnFailure())
+				deps := setupChatDeps(ctx, t, db)
+
+				// Create 3 deletable old archived chats.
+				for range 3 {
+					createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, true, now.Add(-31*24*time.Hour))
+				}
+
+				// Delete with limit 2 — should delete 2, leave 1.
+				deleted, err := db.DeleteOldChats(ctx, database.DeleteOldChatsParams{
+					BeforeTime: now.Add(-30 * 24 * time.Hour),
+					LimitCount: 2,
+				})
+				require.NoError(t, err)
+				require.Equal(t, int64(2), deleted, "should delete exactly 2 chats")
+
+				// Delete again — should delete the remaining 1.
+				deleted, err = db.DeleteOldChats(ctx, database.DeleteOldChatsParams{
+					BeforeTime: now.Add(-30 * 24 * time.Hour),
+					LimitCount: 2,
+				})
+				require.NoError(t, err)
+				require.Equal(t, int64(1), deleted, "should delete remaining 1 chat")
+			},
+		},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			tc.run(t)
+		})
+	}
+}

coderd/database/dump.sql

@@ -220,12 +220,7 @@ CREATE TYPE api_key_scope AS ENUM (
     'chat:read',
     'chat:update',
     'chat:delete',
-    'chat:*',
-    'chat_automation:create',
-    'chat_automation:read',
-    'chat_automation:update',
-    'chat_automation:delete',
-    'chat_automation:*'
+    'chat:*'
 );
 
 CREATE TYPE app_sharing_level AS ENUM (
@@ -275,32 +270,6 @@ CREATE TYPE build_reason AS ENUM (
     'task_resume'
 );
 
-CREATE TYPE chat_automation_event_status AS ENUM (
-    'filtered',
-    'preview',
-    'created',
-    'continued',
-    'rate_limited',
-    'error'
-);
-
-COMMENT ON TYPE chat_automation_event_status IS 'Outcome of a chat automation event: filtered, preview, created, continued, rate_limited, or error.';
-
-CREATE TYPE chat_automation_status AS ENUM (
-    'disabled',
-    'preview',
-    'active'
-);
-
-COMMENT ON TYPE chat_automation_status IS 'Lifecycle state of a chat automation: disabled, preview, or active.';
-
-CREATE TYPE chat_automation_trigger_type AS ENUM (
-    'webhook',
-    'cron'
-);
-
-COMMENT ON TYPE chat_automation_trigger_type IS 'Discriminator for chat automation triggers: webhook or cron.';
-
 CREATE TYPE chat_message_role AS ENUM (
     'system',
     'user',
@@ -324,7 +293,8 @@ CREATE TYPE chat_status AS ENUM (
     'running',
     'paused',
     'completed',
-    'error'
+    'error',
+    'requires_action'
 );
 
 CREATE TYPE connection_status AS ENUM (
@@ -346,6 +316,11 @@ CREATE TYPE cors_behavior AS ENUM (
     'passthru'
 );
 
+CREATE TYPE credential_kind AS ENUM (
+    'centralized',
+    'byok'
+);
+
 CREATE TYPE crypto_key_feature AS ENUM (
     'workspace_apps_token',
     'workspace_apps_api_key',
@@ -1131,7 +1106,10 @@ CREATE TABLE aibridge_interceptions (
     thread_parent_id uuid,
     thread_root_id uuid,
     client_session_id character varying(256),
-    session_id text GENERATED ALWAYS AS (COALESCE(client_session_id, ((thread_root_id)::text)::character varying, ((id)::text)::character varying)) STORED NOT NULL
+    session_id text GENERATED ALWAYS AS (COALESCE(client_session_id, ((thread_root_id)::text)::character varying, ((id)::text)::character varying)) STORED NOT NULL,
+    provider_name text DEFAULT ''::text NOT NULL,
+    credential_kind credential_kind DEFAULT 'centralized'::credential_kind NOT NULL,
+    credential_hint character varying(15) DEFAULT ''::character varying NOT NULL
 );
 
 COMMENT ON TABLE aibridge_interceptions IS 'Audit log of requests intercepted by AI Bridge';
@@ -1146,6 +1124,12 @@ COMMENT ON COLUMN aibridge_interceptions.client_session_id IS 'The session ID su
 
 COMMENT ON COLUMN aibridge_interceptions.session_id IS 'Groups related interceptions into a logical session. Determined by a priority chain: (1) client_session_id — an explicit session identifier supplied by the calling client (e.g. Claude Code); (2) thread_root_id — the root of an agentic thread detected by Bridge through tool-call correlation, used when the client does not supply its own session ID; (3) id — the interception''s own ID, used as a last resort so every interception belongs to exactly one session even if it is standalone. This is a generated column stored on disk so it can be indexed and joined without recomputing the COALESCE on every query.';
 
+COMMENT ON COLUMN aibridge_interceptions.provider_name IS 'The provider instance name which may differ from provider when multiple instances of the same provider type exist.';
+
+COMMENT ON COLUMN aibridge_interceptions.credential_kind IS 'How the request was authenticated: centralized or byok.';
+
+COMMENT ON COLUMN aibridge_interceptions.credential_hint IS 'Masked credential identifier for audit (e.g. sk-a***efgh).';
+
 CREATE TABLE aibridge_model_thoughts (
     interception_id uuid NOT NULL,
     content text NOT NULL,
@@ -1162,7 +1146,9 @@ CREATE TABLE aibridge_token_usages (
     input_tokens bigint NOT NULL,
     output_tokens bigint NOT NULL,
     metadata jsonb,
-    created_at timestamp with time zone NOT NULL
+    created_at timestamp with time zone NOT NULL,
+    cache_read_input_tokens bigint DEFAULT 0 NOT NULL,
+    cache_write_input_tokens bigint DEFAULT 0 NOT NULL
 );
 
 COMMENT ON TABLE aibridge_token_usages IS 'Audit log of tokens used by intercepted requests in AI Bridge';
@@ -1269,103 +1255,43 @@ COMMENT ON COLUMN boundary_usage_stats.window_start IS 'Start of the time window
 
 COMMENT ON COLUMN boundary_usage_stats.updated_at IS 'Timestamp of the last update to this row.';
 
-CREATE TABLE chat_automation_events (
-    id uuid NOT NULL,
-    automation_id uuid NOT NULL,
-    trigger_id uuid,
-    received_at timestamp with time zone NOT NULL,
-    payload jsonb NOT NULL,
-    filter_matched boolean NOT NULL,
-    resolved_labels jsonb,
-    matched_chat_id uuid,
-    created_chat_id uuid,
-    status chat_automation_event_status NOT NULL,
-    error text,
-    CONSTRAINT chat_automation_events_chat_exclusivity CHECK (((matched_chat_id IS NULL) OR (created_chat_id IS NULL)))
-);
-
-COMMENT ON TABLE chat_automation_events IS 'Every trigger invocation produces an event row regardless of outcome. This table is the audit trail and the data source for rate-limit window counts. Rows are append-only and expected to be purged by a background job after a retention period.';
-
-COMMENT ON COLUMN chat_automation_events.payload IS 'The raw payload that was evaluated. For webhooks this is the HTTP body; for cron triggers it is a synthetic JSON envelope with schedule metadata.';
-
-COMMENT ON COLUMN chat_automation_events.filter_matched IS 'Whether the trigger filter conditions matched. False means the event was dropped before any chat interaction.';
-
-COMMENT ON COLUMN chat_automation_events.resolved_labels IS 'Labels resolved from the payload via label_paths. Stored so the event log shows exactly which labels were computed.';
-
-COMMENT ON COLUMN chat_automation_events.matched_chat_id IS 'ID of an existing chat that was found via label matching and continued with a new message.';
-
-COMMENT ON COLUMN chat_automation_events.created_chat_id IS 'ID of a newly created chat (mutually exclusive with matched_chat_id in practice).';
-
-COMMENT ON COLUMN chat_automation_events.status IS 'Outcome of the event: filtered — filter did not match; preview — automation is in preview mode; created — new chat was created; continued — existing chat was continued; rate_limited — rate limit prevented chat action; error — something went wrong.';
-
-CREATE TABLE chat_automation_triggers (
-    id uuid NOT NULL,
-    automation_id uuid NOT NULL,
-    type chat_automation_trigger_type NOT NULL,
-    webhook_secret text,
-    webhook_secret_key_id text,
-    cron_schedule text,
-    last_triggered_at timestamp with time zone,
-    filter jsonb,
-    label_paths jsonb,
-    created_at timestamp with time zone NOT NULL,
-    updated_at timestamp with time zone NOT NULL,
-    CONSTRAINT chat_automation_triggers_cron_fields CHECK (((type <> 'cron'::chat_automation_trigger_type) OR ((cron_schedule IS NOT NULL) AND (webhook_secret IS NULL) AND (webhook_secret_key_id IS NULL)))),
-    CONSTRAINT chat_automation_triggers_webhook_fields CHECK (((type <> 'webhook'::chat_automation_trigger_type) OR ((webhook_secret IS NOT NULL) AND (cron_schedule IS NULL) AND (last_triggered_at IS NULL))))
-);
-
-COMMENT ON TABLE chat_automation_triggers IS 'Triggers define how an automation is invoked. Each automation can have multiple triggers (e.g. one webhook + one cron schedule). Webhook and cron triggers share the same row shape with type-specific nullable columns to keep the schema simple.';
-
-COMMENT ON COLUMN chat_automation_triggers.type IS 'Discriminator: webhook or cron. Determines which nullable columns are meaningful.';
-
-COMMENT ON COLUMN chat_automation_triggers.webhook_secret IS 'HMAC-SHA256 shared secret for webhook signature verification (X-Hub-Signature-256 header). NULL for cron triggers.';
-
-COMMENT ON COLUMN chat_automation_triggers.cron_schedule IS 'Standard 5-field cron expression (minute hour dom month dow), with optional CRON_TZ= prefix. NULL for webhook triggers.';
-
-COMMENT ON COLUMN chat_automation_triggers.last_triggered_at IS 'Timestamp of the last successful cron fire. The scheduler computes next = cron.Next(last_triggered_at) and fires when next <= now. NULL means the trigger has never fired. Not used for webhook triggers.';
-
-COMMENT ON COLUMN chat_automation_triggers.filter IS 'gjson path-to-value filter conditions evaluated against the incoming webhook payload. All conditions must match for the trigger to fire. NULL or empty means match everything.';
-
-COMMENT ON COLUMN chat_automation_triggers.label_paths IS 'Maps chat label keys to gjson paths. When a trigger fires, labels are resolved from the payload and used to find an existing chat to continue (by label match) or set on a newly created chat.';
-
-CREATE TABLE chat_automations (
-    id uuid NOT NULL,
-    owner_id uuid NOT NULL,
-    organization_id uuid NOT NULL,
-    name text NOT NULL,
-    description text DEFAULT ''::text NOT NULL,
-    instructions text DEFAULT ''::text NOT NULL,
+CREATE TABLE chat_debug_runs (
+    id uuid DEFAULT gen_random_uuid() NOT NULL,
+    chat_id uuid NOT NULL,
+    root_chat_id uuid,
+    parent_chat_id uuid,
     model_config_id uuid,
-    mcp_server_ids uuid[] DEFAULT '{}'::uuid[] NOT NULL,
-    allowed_tools text[] DEFAULT '{}'::text[] NOT NULL,
-    status chat_automation_status DEFAULT 'disabled'::chat_automation_status NOT NULL,
-    max_chat_creates_per_hour integer DEFAULT 10 NOT NULL,
-    max_messages_per_hour integer DEFAULT 60 NOT NULL,
-    created_at timestamp with time zone NOT NULL,
-    updated_at timestamp with time zone NOT NULL,
-    CONSTRAINT chat_automations_max_chat_creates_per_hour_check CHECK ((max_chat_creates_per_hour > 0)),
-    CONSTRAINT chat_automations_max_messages_per_hour_check CHECK ((max_messages_per_hour > 0))
+    trigger_message_id bigint,
+    history_tip_message_id bigint,
+    kind text NOT NULL,
+    status text NOT NULL,
+    provider text,
+    model text,
+    summary jsonb DEFAULT '{}'::jsonb NOT NULL,
+    started_at timestamp with time zone DEFAULT now() NOT NULL,
+    updated_at timestamp with time zone DEFAULT now() NOT NULL,
+    finished_at timestamp with time zone
 );
 
-COMMENT ON TABLE chat_automations IS 'Chat automations bridge external events (webhooks, cron schedules) to Coder chats. A chat automation defines what to say, which model and tools to use, and how fast it is allowed to create or continue chats.';
-
-COMMENT ON COLUMN chat_automations.owner_id IS 'The user on whose behalf chats are created. All RBAC checks and chat ownership are scoped to this user.';
-
-COMMENT ON COLUMN chat_automations.organization_id IS 'Organization scope for RBAC. Combined with owner_id and name to form a unique constraint so automations are namespaced per user per org.';
-
-COMMENT ON COLUMN chat_automations.instructions IS 'The user-role message injected into every chat this automation creates. This is the core prompt that tells the LLM what to do.';
-
-COMMENT ON COLUMN chat_automations.model_config_id IS 'Optional model configuration override. When NULL the deployment default is used. SET NULL on delete so automations survive config changes gracefully.';
-
-COMMENT ON COLUMN chat_automations.mcp_server_ids IS 'MCP servers to attach to chats created by this automation. Stored as an array of UUIDs rather than a join table because the set is small and always read/written atomically.';
-
-COMMENT ON COLUMN chat_automations.allowed_tools IS 'Tool allowlist. Empty means all tools available to the model config are permitted.';
-
-COMMENT ON COLUMN chat_automations.status IS 'Lifecycle state: disabled — trigger events are silently dropped; preview — events are logged but no chat is created (dry-run); active — events create or continue chats.';
-
-COMMENT ON COLUMN chat_automations.max_chat_creates_per_hour IS 'Maximum number of new chats this automation may create in a rolling one-hour window. Prevents runaway webhook storms from flooding the system.';
-
-COMMENT ON COLUMN chat_automations.max_messages_per_hour IS 'Maximum total messages (creates + continues) this automation may send in a rolling one-hour window. A second, broader throttle that catches high-frequency continuation patterns.';
+CREATE TABLE chat_debug_steps (
+    id uuid DEFAULT gen_random_uuid() NOT NULL,
+    run_id uuid NOT NULL,
+    chat_id uuid NOT NULL,
+    step_number integer NOT NULL,
+    operation text NOT NULL,
+    status text NOT NULL,
+    history_tip_message_id bigint,
+    assistant_message_id bigint,
+    normalized_request jsonb NOT NULL,
+    normalized_response jsonb,
+    usage jsonb,
+    attempts jsonb DEFAULT '[]'::jsonb NOT NULL,
+    error jsonb,
+    metadata jsonb DEFAULT '{}'::jsonb NOT NULL,
+    started_at timestamp with time zone DEFAULT now() NOT NULL,
+    updated_at timestamp with time zone DEFAULT now() NOT NULL,
+    finished_at timestamp with time zone
+);
 
 CREATE TABLE chat_diff_statuses (
     chat_id uuid NOT NULL,
@@ -1393,6 +1319,11 @@ CREATE TABLE chat_diff_statuses (
     head_branch text
 );
 
+CREATE TABLE chat_file_links (
+    chat_id uuid NOT NULL,
+    file_id uuid NOT NULL
+);
+
 CREATE TABLE chat_files (
     id uuid DEFAULT gen_random_uuid() NOT NULL,
     owner_id uuid NOT NULL,
@@ -1467,7 +1398,11 @@ CREATE TABLE chat_providers (
     created_at timestamp with time zone DEFAULT now() NOT NULL,
     updated_at timestamp with time zone DEFAULT now() NOT NULL,
     base_url text DEFAULT ''::text NOT NULL,
-    CONSTRAINT chat_providers_provider_check CHECK ((provider = ANY (ARRAY['anthropic'::text, 'azure'::text, 'bedrock'::text, 'google'::text, 'openai'::text, 'openai-compat'::text, 'openrouter'::text, 'vercel'::text])))
+    central_api_key_enabled boolean DEFAULT true NOT NULL,
+    allow_user_api_key boolean DEFAULT false NOT NULL,
+    allow_central_api_key_fallback boolean DEFAULT false NOT NULL,
+    CONSTRAINT chat_providers_provider_check CHECK ((provider = ANY (ARRAY['anthropic'::text, 'azure'::text, 'bedrock'::text, 'google'::text, 'openai'::text, 'openai-compat'::text, 'openrouter'::text, 'vercel'::text]))),
+    CONSTRAINT valid_credential_policy CHECK (((central_api_key_enabled OR allow_user_api_key) AND ((NOT allow_central_api_key_fallback) OR (central_api_key_enabled AND allow_user_api_key))))
 );
 
 COMMENT ON COLUMN chat_providers.api_key_key_id IS 'The ID of the key used to encrypt the provider API key. If this is NULL, the API key is not encrypted';
@@ -1534,7 +1469,7 @@ CREATE TABLE chats (
     pin_order integer DEFAULT 0 NOT NULL,
     last_read_message_id bigint,
     last_injected_context jsonb,
-    automation_id uuid
+    dynamic_tools jsonb
 );
 
 CREATE TABLE connection_logs (
@@ -2879,6 +2814,17 @@ COMMENT ON TABLE usage_events_daily IS 'usage_events_daily is a daily rollup of
 
 COMMENT ON COLUMN usage_events_daily.day IS 'The date of the summed usage events, always in UTC.';
 
+CREATE TABLE user_chat_provider_keys (
+    id uuid DEFAULT gen_random_uuid() NOT NULL,
+    user_id uuid NOT NULL,
+    chat_provider_id uuid NOT NULL,
+    api_key text NOT NULL,
+    api_key_key_id text,
+    created_at timestamp with time zone DEFAULT now() NOT NULL,
+    updated_at timestamp with time zone DEFAULT now() NOT NULL,
+    CONSTRAINT user_chat_provider_keys_api_key_check CHECK ((api_key <> ''::text))
+);
+
 CREATE TABLE user_configs (
     user_id uuid NOT NULL,
     key character varying(256) NOT NULL,
@@ -2920,7 +2866,8 @@ CREATE TABLE user_secrets (
     env_name text DEFAULT ''::text NOT NULL,
     file_path text DEFAULT ''::text NOT NULL,
     created_at timestamp with time zone DEFAULT CURRENT_TIMESTAMP NOT NULL,
-    updated_at timestamp with time zone DEFAULT CURRENT_TIMESTAMP NOT NULL
+    updated_at timestamp with time zone DEFAULT CURRENT_TIMESTAMP NOT NULL,
+    value_key_id text
 );
 
 CREATE TABLE user_status_changes (
@@ -3450,18 +3397,18 @@ ALTER TABLE ONLY audit_logs
 ALTER TABLE ONLY boundary_usage_stats
     ADD CONSTRAINT boundary_usage_stats_pkey PRIMARY KEY (replica_id);
 
-ALTER TABLE ONLY chat_automation_events
-    ADD CONSTRAINT chat_automation_events_pkey PRIMARY KEY (id);
+ALTER TABLE ONLY chat_debug_runs
+    ADD CONSTRAINT chat_debug_runs_pkey PRIMARY KEY (id);
 
-ALTER TABLE ONLY chat_automation_triggers
-    ADD CONSTRAINT chat_automation_triggers_pkey PRIMARY KEY (id);
-
-ALTER TABLE ONLY chat_automations
-    ADD CONSTRAINT chat_automations_pkey PRIMARY KEY (id);
+ALTER TABLE ONLY chat_debug_steps
+    ADD CONSTRAINT chat_debug_steps_pkey PRIMARY KEY (id);
 
 ALTER TABLE ONLY chat_diff_statuses
     ADD CONSTRAINT chat_diff_statuses_pkey PRIMARY KEY (chat_id);
 
+ALTER TABLE ONLY chat_file_links
+    ADD CONSTRAINT chat_file_links_chat_id_file_id_key UNIQUE (chat_id, file_id);
+
 ALTER TABLE ONLY chat_files
     ADD CONSTRAINT chat_files_pkey PRIMARY KEY (id);
 
@@ -3684,6 +3631,12 @@ ALTER TABLE ONLY usage_events_daily
 ALTER TABLE ONLY usage_events
     ADD CONSTRAINT usage_events_pkey PRIMARY KEY (id);
 
+ALTER TABLE ONLY user_chat_provider_keys
+    ADD CONSTRAINT user_chat_provider_keys_pkey PRIMARY KEY (id);
+
+ALTER TABLE ONLY user_chat_provider_keys
+    ADD CONSTRAINT user_chat_provider_keys_user_id_chat_provider_id_key UNIQUE (user_id, chat_provider_id);
+
 ALTER TABLE ONLY user_configs
     ADD CONSTRAINT user_configs_pkey PRIMARY KEY (user_id, key);
 
@@ -3844,22 +3797,24 @@ CREATE INDEX idx_audit_log_user_id ON audit_logs USING btree (user_id);
 
 CREATE INDEX idx_audit_logs_time_desc ON audit_logs USING btree ("time" DESC);
 
-CREATE INDEX idx_chat_automation_events_automation_id_received_at ON chat_automation_events USING btree (automation_id, received_at DESC);
+CREATE INDEX idx_chat_debug_runs_chat_started ON chat_debug_runs USING btree (chat_id, started_at DESC);
 
-CREATE INDEX idx_chat_automation_events_rate_limit ON chat_automation_events USING btree (automation_id, received_at) WHERE (status = ANY (ARRAY['created'::chat_automation_event_status, 'continued'::chat_automation_event_status]));
+CREATE UNIQUE INDEX idx_chat_debug_runs_id_chat ON chat_debug_runs USING btree (id, chat_id);
 
-CREATE INDEX idx_chat_automation_events_received_at ON chat_automation_events USING btree (received_at);
+CREATE INDEX idx_chat_debug_runs_stale ON chat_debug_runs USING btree (updated_at) WHERE (finished_at IS NULL);
 
-CREATE INDEX idx_chat_automation_triggers_automation_id ON chat_automation_triggers USING btree (automation_id);
+CREATE INDEX idx_chat_debug_steps_chat_assistant_msg ON chat_debug_steps USING btree (chat_id, assistant_message_id) WHERE (assistant_message_id IS NOT NULL);
 
-CREATE INDEX idx_chat_automations_organization_id ON chat_automations USING btree (organization_id);
+CREATE INDEX idx_chat_debug_steps_chat_tip ON chat_debug_steps USING btree (chat_id, history_tip_message_id);
 
-CREATE INDEX idx_chat_automations_owner_id ON chat_automations USING btree (owner_id);
+CREATE UNIQUE INDEX idx_chat_debug_steps_run_step ON chat_debug_steps USING btree (run_id, step_number);
 
-CREATE UNIQUE INDEX idx_chat_automations_owner_org_name ON chat_automations USING btree (owner_id, organization_id, name);
+CREATE INDEX idx_chat_debug_steps_stale ON chat_debug_steps USING btree (updated_at) WHERE (finished_at IS NULL);
 
 CREATE INDEX idx_chat_diff_statuses_stale_at ON chat_diff_statuses USING btree (stale_at);
 
+CREATE INDEX idx_chat_file_links_chat_id ON chat_file_links USING btree (chat_id);
+
 CREATE INDEX idx_chat_files_org ON chat_files USING btree (organization_id);
 
 CREATE INDEX idx_chat_files_owner ON chat_files USING btree (owner_id);
@@ -3886,7 +3841,7 @@ CREATE INDEX idx_chat_providers_enabled ON chat_providers USING btree (enabled);
 
 CREATE INDEX idx_chat_queued_messages_chat_id ON chat_queued_messages USING btree (chat_id);
 
-CREATE INDEX idx_chats_automation_id ON chats USING btree (automation_id);
+CREATE INDEX idx_chats_agent_id ON chats USING btree (agent_id) WHERE (agent_id IS NOT NULL);
 
 CREATE INDEX idx_chats_labels ON chats USING gin (labels);
 
@@ -3894,8 +3849,6 @@ CREATE INDEX idx_chats_last_model_config_id ON chats USING btree (last_model_con
 
 CREATE INDEX idx_chats_owner ON chats USING btree (owner_id);
 
-CREATE INDEX idx_chats_owner_updated_id ON chats USING btree (owner_id, updated_at DESC, id DESC);
-
 CREATE INDEX idx_chats_parent_chat_id ON chats USING btree (parent_chat_id);
 
 CREATE INDEX idx_chats_pending ON chats USING btree (status) WHERE (status = 'pending'::chat_status);
@@ -4161,36 +4114,21 @@ ALTER TABLE ONLY aibridge_interceptions
 ALTER TABLE ONLY api_keys
     ADD CONSTRAINT api_keys_user_id_uuid_fkey FOREIGN KEY (user_id) REFERENCES users(id) ON DELETE CASCADE;
 
-ALTER TABLE ONLY chat_automation_events
-    ADD CONSTRAINT chat_automation_events_automation_id_fkey FOREIGN KEY (automation_id) REFERENCES chat_automations(id) ON DELETE CASCADE;
+ALTER TABLE ONLY chat_debug_runs
+    ADD CONSTRAINT chat_debug_runs_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
 
-ALTER TABLE ONLY chat_automation_events
-    ADD CONSTRAINT chat_automation_events_created_chat_id_fkey FOREIGN KEY (created_chat_id) REFERENCES chats(id) ON DELETE SET NULL;
-
-ALTER TABLE ONLY chat_automation_events
-    ADD CONSTRAINT chat_automation_events_matched_chat_id_fkey FOREIGN KEY (matched_chat_id) REFERENCES chats(id) ON DELETE SET NULL;
-
-ALTER TABLE ONLY chat_automation_events
-    ADD CONSTRAINT chat_automation_events_trigger_id_fkey FOREIGN KEY (trigger_id) REFERENCES chat_automation_triggers(id) ON DELETE SET NULL;
-
-ALTER TABLE ONLY chat_automation_triggers
-    ADD CONSTRAINT chat_automation_triggers_automation_id_fkey FOREIGN KEY (automation_id) REFERENCES chat_automations(id) ON DELETE CASCADE;
-
-ALTER TABLE ONLY chat_automation_triggers
-    ADD CONSTRAINT chat_automation_triggers_webhook_secret_key_id_fkey FOREIGN KEY (webhook_secret_key_id) REFERENCES dbcrypt_keys(active_key_digest);
-
-ALTER TABLE ONLY chat_automations
-    ADD CONSTRAINT chat_automations_model_config_id_fkey FOREIGN KEY (model_config_id) REFERENCES chat_model_configs(id) ON DELETE SET NULL;
-
-ALTER TABLE ONLY chat_automations
-    ADD CONSTRAINT chat_automations_organization_id_fkey FOREIGN KEY (organization_id) REFERENCES organizations(id) ON DELETE CASCADE;
-
-ALTER TABLE ONLY chat_automations
-    ADD CONSTRAINT chat_automations_owner_id_fkey FOREIGN KEY (owner_id) REFERENCES users(id) ON DELETE CASCADE;
+ALTER TABLE ONLY chat_debug_steps
+    ADD CONSTRAINT chat_debug_steps_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
 
 ALTER TABLE ONLY chat_diff_statuses
     ADD CONSTRAINT chat_diff_statuses_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
 
+ALTER TABLE ONLY chat_file_links
+    ADD CONSTRAINT chat_file_links_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
+
+ALTER TABLE ONLY chat_file_links
+    ADD CONSTRAINT chat_file_links_file_id_fkey FOREIGN KEY (file_id) REFERENCES chat_files(id) ON DELETE CASCADE;
+
 ALTER TABLE ONLY chat_files
     ADD CONSTRAINT chat_files_organization_id_fkey FOREIGN KEY (organization_id) REFERENCES organizations(id) ON DELETE CASCADE;
 
@@ -4224,9 +4162,6 @@ ALTER TABLE ONLY chat_queued_messages
 ALTER TABLE ONLY chats
     ADD CONSTRAINT chats_agent_id_fkey FOREIGN KEY (agent_id) REFERENCES workspace_agents(id) ON DELETE SET NULL;
 
-ALTER TABLE ONLY chats
-    ADD CONSTRAINT chats_automation_id_fkey FOREIGN KEY (automation_id) REFERENCES chat_automations(id) ON DELETE SET NULL;
-
 ALTER TABLE ONLY chats
     ADD CONSTRAINT chats_build_id_fkey FOREIGN KEY (build_id) REFERENCES workspace_builds(id) ON DELETE SET NULL;
 
@@ -4257,6 +4192,9 @@ ALTER TABLE ONLY connection_logs
 ALTER TABLE ONLY crypto_keys
     ADD CONSTRAINT crypto_keys_secret_key_id_fkey FOREIGN KEY (secret_key_id) REFERENCES dbcrypt_keys(active_key_digest);
 
+ALTER TABLE ONLY chat_debug_steps
+    ADD CONSTRAINT fk_chat_debug_steps_run_chat FOREIGN KEY (run_id, chat_id) REFERENCES chat_debug_runs(id, chat_id) ON DELETE CASCADE;
+
 ALTER TABLE ONLY oauth2_provider_app_tokens
     ADD CONSTRAINT fk_oauth2_provider_app_tokens_user_id FOREIGN KEY (user_id) REFERENCES users(id) ON DELETE CASCADE;
 
@@ -4440,6 +4378,15 @@ ALTER TABLE ONLY templates
 ALTER TABLE ONLY templates
     ADD CONSTRAINT templates_organization_id_fkey FOREIGN KEY (organization_id) REFERENCES organizations(id) ON DELETE CASCADE;
 
+ALTER TABLE ONLY user_chat_provider_keys
+    ADD CONSTRAINT user_chat_provider_keys_api_key_key_id_fkey FOREIGN KEY (api_key_key_id) REFERENCES dbcrypt_keys(active_key_digest);
+
+ALTER TABLE ONLY user_chat_provider_keys
+    ADD CONSTRAINT user_chat_provider_keys_chat_provider_id_fkey FOREIGN KEY (chat_provider_id) REFERENCES chat_providers(id) ON DELETE CASCADE;
+
+ALTER TABLE ONLY user_chat_provider_keys
+    ADD CONSTRAINT user_chat_provider_keys_user_id_fkey FOREIGN KEY (user_id) REFERENCES users(id) ON DELETE CASCADE;
+
 ALTER TABLE ONLY user_configs
     ADD CONSTRAINT user_configs_user_id_fkey FOREIGN KEY (user_id) REFERENCES users(id) ON DELETE CASCADE;
 
@@ -4458,6 +4405,9 @@ ALTER TABLE ONLY user_links
 ALTER TABLE ONLY user_secrets
     ADD CONSTRAINT user_secrets_user_id_fkey FOREIGN KEY (user_id) REFERENCES users(id) ON DELETE CASCADE;
 
+ALTER TABLE ONLY user_secrets
+    ADD CONSTRAINT user_secrets_value_key_id_fkey FOREIGN KEY (value_key_id) REFERENCES dbcrypt_keys(active_key_digest);
+
 ALTER TABLE ONLY user_status_changes
     ADD CONSTRAINT user_status_changes_user_id_fkey FOREIGN KEY (user_id) REFERENCES users(id);