feat(site): add Debug panel components and settings

Change-Id: Ibeb0088ae26acd83e98d83d2eb00c0573962c357
Signed-off-by: Thomas Kosiewski <tk@coder.com>

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

@@ -18,35 +18,35 @@ The 5.x era resolves years of module system ambiguity and cleans house on legacy
 
 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                              |
+| 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
 

.github/cherry-pick-bot.yml

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

.github/dependabot.yaml

@@ -91,12 +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
 
@@ -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
 
@@ -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/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

@@ -81,7 +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
 
@@ -121,22 +121,22 @@ jobs:
           fi
 
           # Derive the release branch from the version tag.
-          # Standard: 2.10.2 -> release/2.10
-          # RC:       2.32.0-rc.0 -> release/2.32-rc.0
+          # Non-RC releases must be on a release/X.Y branch.
+          # RC tags are allowed on any branch (typically main).
           version="$(./scripts/version.sh)"
+          # Strip any pre-release suffix first (e.g. 2.32.0-rc.0 -> 2.32.0)
+          base_version="${version%%-*}"
+          # Then strip patch to get major.minor (e.g. 2.32.0 -> 2.32)
+          release_branch="release/${base_version%.*}"
+
           if [[ "$version" == *-rc.* ]]; then
-            # Extract major.minor and rc suffix from e.g. 2.32.0-rc.0
-            base_version="${version%%-rc.*}"   # 2.32.0
-            major_minor="${base_version%.*}"   # 2.32
-            rc_suffix="${version##*-rc.}"      # 0
-            release_branch="release/${major_minor}-rc.${rc_suffix}"
+            echo "RC release detected — skipping release branch check (RC tags are cut from main)."
           else
-            release_branch=release/${version%.*}
-          fi
-          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 ${release_branch} when creating a release, did you use scripts/release.sh?"
-            exit 1
+            branch_contains_tag=$(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
@@ -673,7 +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
 
@@ -749,7 +749,7 @@ 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/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
 

.gitignore

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

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.
@@ -1067,88 +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

@@ -102,6 +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.
@@ -214,6 +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),
@@ -280,6 +284,8 @@ type agent struct {
 	sshServer                          *agentssh.Server
 	sshMaxTimeout                      time.Duration
 	blockFileTransfer                  bool
+	blockReversePortForwarding         bool
+	blockLocalPortForwarding           bool
 
 	lifecycleUpdate            chan struct{}
 	lifecycleReported          chan codersdk.WorkspaceAgentLifecycle
@@ -331,12 +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 {

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" {

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

@@ -134,6 +134,33 @@ func Config(workingDir string) (workspacesdk.ContextConfigResponse, []string) {
 	}, 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 {

agent/agentcontextconfig/api_test.go

@@ -23,18 +23,144 @@ func filterParts(parts []codersdk.ChatMessagePart, t codersdk.ChatMessagePartTyp
 	return out
 }
 
-func TestConfig(t *testing.T) {
-	t.Run("Defaults", func(t *testing.T) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
+func writeSkillMetaFileInRoot(t *testing.T, skillsRoot, name, description string) string {
+	t.Helper()
 
-		// Clear all env vars so defaults are used.
-		t.Setenv(agentcontextconfig.EnvInstructionsDirs, "")
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
+	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)
@@ -46,20 +172,18 @@ func TestConfig(t *testing.T) {
 		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) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
-
 		optInstructions := t.TempDir()
 		optSkills := t.TempDir()
 		optMCP := platformAbsPath("opt", "mcp.json")
-
-		t.Setenv(agentcontextconfig.EnvInstructionsDirs, optInstructions)
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "CUSTOM.md")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, optSkills)
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "META.yaml")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, optMCP)
+		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.
@@ -85,15 +209,12 @@ func TestConfig(t *testing.T) {
 		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 := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
+		fakeHome := setupConfigTestEnv(t, map[string]string{
+			agentcontextconfig.EnvInstructionsFile: "  CLAUDE.md  ",
+		})
 		t.Setenv(agentcontextconfig.EnvInstructionsDirs, fakeHome)
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "  CLAUDE.md  ")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
 
 		workDir := t.TempDir()
 		// Create a file matching the trimmed name.
@@ -106,19 +227,13 @@ func TestConfig(t *testing.T) {
 		require.Equal(t, "hello", ctxFiles[0].ContextFileContent)
 	})
 
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
 	t.Run("CommaSeparatedDirs", func(t *testing.T) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
-
 		a := t.TempDir()
 		b := t.TempDir()
-
-		t.Setenv(agentcontextconfig.EnvInstructionsDirs, a+","+b)
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
+		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))
@@ -133,17 +248,10 @@ func TestConfig(t *testing.T) {
 		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) {
-		t.Setenv(agentcontextconfig.EnvInstructionsDirs, "")
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
-
 		workDir := t.TempDir()
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
+		fakeHome := setupConfigTestEnv(t, nil)
 
 		// Create ~/.coder/AGENTS.md
 		coderDir := filepath.Join(fakeHome, ".coder")
@@ -164,16 +272,9 @@ func TestConfig(t *testing.T) {
 		require.False(t, ctxFiles[0].ContextFileTruncated)
 	})
 
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
 	t.Run("ReadsWorkingDirInstructionFile", func(t *testing.T) {
-		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, "")
-
+		setupConfigTestEnv(t, nil)
 		workDir := t.TempDir()
 
 		// Create AGENTS.md in the working directory.
@@ -193,16 +294,9 @@ func TestConfig(t *testing.T) {
 		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) {
-		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, "")
-
+		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))
@@ -215,79 +309,47 @@ func TestConfig(t *testing.T) {
 		require.Len(t, ctxFiles[0].ContextFileContent, 64*1024)
 	})
 
-	t.Run("SanitizesHTMLComments", func(t *testing.T) {
-		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, "")
+	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,
+			))
 
-		workDir := t.TempDir()
-		require.NoError(t, os.WriteFile(
-			filepath.Join(workDir, "AGENTS.md"),
-			[]byte("visible\n<!-- hidden -->content"),
-			0o600,
-		))
+			cfg, _ := agentcontextconfig.Config(workDir)
 
-		cfg, _ := agentcontextconfig.Config(workDir)
-
-		ctxFiles := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeContextFile)
-		require.Len(t, ctxFiles, 1)
-		require.Equal(t, "visible\ncontent", ctxFiles[0].ContextFileContent)
-	})
-
-	t.Run("SanitizesInvisibleUnicode", func(t *testing.T) {
-		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, "")
-
-		workDir := t.TempDir()
-		// U+200B (zero-width space) should be stripped.
-		require.NoError(t, os.WriteFile(
-			filepath.Join(workDir, "AGENTS.md"),
-			[]byte("before\u200bafter"),
-			0o600,
-		))
-
-		cfg, _ := agentcontextconfig.Config(workDir)
-
-		ctxFiles := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeContextFile)
-		require.Len(t, ctxFiles, 1)
-		require.Equal(t, "beforeafter", ctxFiles[0].ContextFileContent)
-	})
-
-	t.Run("NormalizesCRLF", func(t *testing.T) {
-		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, "")
-
-		workDir := t.TempDir()
-		require.NoError(t, os.WriteFile(
-			filepath.Join(workDir, "AGENTS.md"),
-			[]byte("line1\r\nline2\rline3"),
-			0o600,
-		))
-
-		cfg, _ := agentcontextconfig.Config(workDir)
-
-		ctxFiles := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeContextFile)
-		require.Len(t, ctxFiles, 1)
-		require.Equal(t, "line1\nline2\nline3", ctxFiles[0].ContextFileContent)
-	})
+			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)
@@ -320,17 +382,13 @@ func TestConfig(t *testing.T) {
 		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) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
-
 		nonExistent := filepath.Join(t.TempDir(), "does-not-exist")
-		t.Setenv(agentcontextconfig.EnvInstructionsDirs, nonExistent)
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, nonExistent)
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
+		setupConfigTestEnv(t, map[string]string{
+			agentcontextconfig.EnvInstructionsDirs: nonExistent,
+			agentcontextconfig.EnvSkillsDirs:       nonExistent,
+		})
 
 		workDir := t.TempDir()
 		cfg, _ := agentcontextconfig.Config(workDir)
@@ -340,17 +398,13 @@ func TestConfig(t *testing.T) {
 		require.Empty(t, cfg.Parts)
 	})
 
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
 	t.Run("MCPConfigFilesResolvedSeparately", 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.EnvSkillsDirs, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-
 		optMCP := platformAbsPath("opt", "custom.json")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, optMCP)
+		fakeHome := setupConfigTestEnv(t, map[string]string{
+			agentcontextconfig.EnvMCPConfigFiles: optMCP,
+		})
+		t.Setenv(agentcontextconfig.EnvInstructionsDirs, fakeHome)
 
 		workDir := t.TempDir()
 		_, mcpFiles := agentcontextconfig.Config(workDir)
@@ -358,14 +412,10 @@ func TestConfig(t *testing.T) {
 		require.Equal(t, []string{optMCP}, mcpFiles)
 	})
 
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
 	t.Run("SkillNameMustMatchDir", func(t *testing.T) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
+		fakeHome := setupConfigTestEnv(t, nil)
 		t.Setenv(agentcontextconfig.EnvInstructionsDirs, fakeHome)
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
 
 		workDir := t.TempDir()
 		skillsDir := filepath.Join(workDir, "skills")
@@ -385,14 +435,10 @@ func TestConfig(t *testing.T) {
 		require.Empty(t, skillParts)
 	})
 
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
 	t.Run("DuplicateSkillsFirstWins", func(t *testing.T) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
+		fakeHome := setupConfigTestEnv(t, nil)
 		t.Setenv(agentcontextconfig.EnvInstructionsDirs, fakeHome)
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
 
 		workDir := t.TempDir()
 		skillsDir1 := filepath.Join(workDir, "skills1")

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/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

@@ -5,7 +5,9 @@ import (
 	"encoding/json"
 	"errors"
 	"io"
+	"mime/multipart"
 	"net/http"
+	"net/textproto"
 	"strconv"
 	"sync"
 	"time"
@@ -620,6 +622,11 @@ func (a *API) handleRecordingStop(rw http.ResponseWriter, r *http.Request) {
 		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",
@@ -633,10 +640,60 @@ func (a *API) handleRecordingStop(rw http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	rw.Header().Set("Content-Type", "video/mp4")
-	rw.Header().Set("Content-Length", strconv.FormatInt(artifact.Size, 10))
+	// 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)
-	_, _ = io.Copy(rw, artifact.Reader)
+
+	// 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,

agent/x/agentdesktop/api_test.go

@@ -4,12 +4,17 @@ import (
 	"bytes"
 	"context"
 	"encoding/json"
+	"errors"
 	"fmt"
+	"io"
+	"mime"
+	"mime/multipart"
 	"net"
 	"net/http"
 	"net/http/httptest"
 	"os"
 	"slices"
+	"strings"
 	"sync"
 	"testing"
 	"time"
@@ -59,6 +64,8 @@ type fakeDesktop struct {
 	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
@@ -187,10 +194,15 @@ func (f *fakeDesktop) StopRecording(_ context.Context, recordingID string) (*age
 		_ = file.Close()
 		return nil, err
 	}
-	return &agentdesktop.RecordingArtifact{
+	artifact := &agentdesktop.RecordingArtifact{
 		Reader: file,
 		Size:   info.Size(),
-	}, nil
+	}
+	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() {
@@ -785,8 +797,8 @@ func TestRecordingStartStop(t *testing.T) {
 	req = httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
 	handler.ServeHTTP(rr, req)
 	require.Equal(t, http.StatusOK, rr.Code)
-	assert.Equal(t, "video/mp4", rr.Header().Get("Content-Type"))
-	assert.Equal(t, []byte("fake-mp4-data-"+testRecIDDefault+"-1"), rr.Body.Bytes())
+	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) {
@@ -847,8 +859,8 @@ func TestRecordingStartIdempotent(t *testing.T) {
 	req := httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
 	handler.ServeHTTP(rr, req)
 	require.Equal(t, http.StatusOK, rr.Code)
-	assert.Equal(t, "video/mp4", rr.Header().Get("Content-Type"))
-	assert.Equal(t, []byte("fake-mp4-data-"+testRecIDStartIdempotent+"-1"), rr.Body.Bytes())
+	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) {
@@ -872,7 +884,7 @@ func TestRecordingStopIdempotent(t *testing.T) {
 	require.Equal(t, http.StatusOK, rr.Code)
 
 	// Stop twice - both should succeed with identical data.
-	var bodies [2][]byte
+	var videoParts [2][]byte
 	for i := range 2 {
 		body, err := json.Marshal(map[string]string{"recording_id": testRecIDStopIdempotent})
 		require.NoError(t, err)
@@ -880,10 +892,10 @@ func TestRecordingStopIdempotent(t *testing.T) {
 		request := httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(body))
 		handler.ServeHTTP(recorder, request)
 		require.Equal(t, http.StatusOK, recorder.Code)
-		assert.Equal(t, "video/mp4", recorder.Header().Get("Content-Type"))
-		bodies[i] = recorder.Body.Bytes()
+		parts := parseMultipartParts(t, recorder.Header().Get("Content-Type"), recorder.Body.Bytes())
+		videoParts[i] = parts["video/mp4"]
 	}
-	assert.Equal(t, bodies[0], bodies[1])
+	assert.Equal(t, videoParts[0], videoParts[1])
 }
 
 func TestRecordingStopInvalidIDFormat(t *testing.T) {
@@ -1004,8 +1016,8 @@ func TestRecordingMultipleSimultaneous(t *testing.T) {
 		req := httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(body))
 		handler.ServeHTTP(rr, req)
 		require.Equal(t, http.StatusOK, rr.Code)
-		assert.Equal(t, "video/mp4", rr.Header().Get("Content-Type"))
-		assert.Equal(t, expected[id], rr.Body.Bytes())
+		parts := parseMultipartParts(t, rr.Header().Get("Content-Type"), rr.Body.Bytes())
+		assert.Equal(t, expected[id], parts["video/mp4"])
 	}
 }
 
@@ -1112,8 +1124,8 @@ func TestRecordingStartAfterCompleted(t *testing.T) {
 	req = httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
 	handler.ServeHTTP(rr, req)
 	require.Equal(t, http.StatusOK, rr.Code)
-	assert.Equal(t, "video/mp4", rr.Header().Get("Content-Type"))
-	firstData := rr.Body.Bytes()
+	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
@@ -1128,8 +1140,8 @@ func TestRecordingStartAfterCompleted(t *testing.T) {
 	req = httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
 	handler.ServeHTTP(rr, req)
 	require.Equal(t, http.StatusOK, rr.Code)
-	assert.Equal(t, "video/mp4", rr.Header().Get("Content-Type"))
-	secondData := rr.Body.Bytes()
+	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
@@ -1235,3 +1247,166 @@ func TestRecordingStopCorrupted(t *testing.T) {
 	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

@@ -105,6 +105,11 @@ type RecordingArtifact struct {
 	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.

agent/x/agentdesktop/portabledesktop.go

@@ -56,6 +56,7 @@ type screenshotOutput struct {
 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
@@ -383,13 +384,20 @@ func (p *portableDesktop) StartRecording(ctx context.Context, recordingID string
 			}
 		}
 		// Completed recording - discard old file, start fresh.
-		if err := os.Remove(rec.filePath); err != nil && !os.IsNotExist(err) {
+		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)
 	}
 
@@ -406,6 +414,7 @@ func (p *portableDesktop) StartRecording(ctx context.Context, recordingID string
 	}
 
 	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.
@@ -419,6 +428,7 @@ func (p *portableDesktop) StartRecording(ctx context.Context, recordingID string
 		"--idle-speedup", "20",
 		"--idle-min-duration", "0.35",
 		"--idle-noise-tolerance", "-38dB",
+		"--thumbnail", thumbPath,
 		filePath)
 
 	if err := cmd.Start(); err != nil {
@@ -427,9 +437,10 @@ func (p *portableDesktop) StartRecording(ctx context.Context, recordingID string
 	}
 
 	rec := &recordingProcess{
-		cmd:      cmd,
-		filePath: filePath,
-		done:     make(chan struct{}),
+		cmd:       cmd,
+		filePath:  filePath,
+		thumbPath: thumbPath,
+		done:      make(chan struct{}),
 	}
 	go func() {
 		rec.waitErr = cmd.Wait()
@@ -499,10 +510,35 @@ func (p *portableDesktop) StopRecording(ctx context.Context, recordingID string)
 		_ = f.Close()
 		return nil, xerrors.Errorf("stat recording artifact: %w", err)
 	}
-	return &RecordingArtifact{
+	artifact := &RecordingArtifact{
 		Reader: f,
 		Size:   info.Size(),
-	}, nil
+	}
+	// 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.
@@ -571,18 +607,33 @@ func (p *portableDesktop) lockedCleanStaleRecordings(ctx context.Context) {
 		}
 		info, err := os.Stat(rec.filePath)
 		if err != nil {
-			// File already removed or inaccessible; drop entry.
+			// 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 && !os.IsNotExist(err) {
+			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)
 		}
 	}
@@ -603,13 +654,14 @@ func (p *portableDesktop) Close() error {
 	// Snapshot recording file paths and idle goroutine channels
 	// for cleanup, then clear the map.
 	type recEntry struct {
-		id       string
-		filePath string
-		idleDone chan 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, idleDone: rec.idleDone})
+		allRecs = append(allRecs, recEntry{id: id, filePath: rec.filePath, thumbPath: rec.thumbPath, idleDone: rec.idleDone})
 		delete(p.recordings, id)
 	}
 	session := p.session
@@ -630,13 +682,20 @@ func (p *portableDesktop) Close() error {
 	go func() {
 		defer close(cleanupDone)
 		for _, entry := range allRecs {
-			if err := os.Remove(entry.filePath); err != nil && !os.IsNotExist(err) {
+			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()

agent/x/agentdesktop/portabledesktop_internal_test.go

@@ -2,6 +2,7 @@ package agentdesktop
 
 import (
 	"context"
+	"io"
 	"os"
 	"os/exec"
 	"path/filepath"
@@ -584,6 +585,7 @@ func TestPortableDesktop_StartRecording(t *testing.T) {
 		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
 		}
 	}
@@ -666,6 +668,66 @@ func TestPortableDesktop_StopRecording_ReturnsArtifact(t *testing.T) {
 	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())
 }
 
@@ -750,12 +812,18 @@ func TestPortableDesktop_IdleTimeout_StopsRecordings(t *testing.T) {
 	stopTrap := clk.Trap().NewTimer("agentdesktop", "stop_timeout")
 
 	// Advance past idle timeout to trigger the stop-all.
-	clk.Advance(idleTimeout)
+	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()
@@ -877,11 +945,17 @@ func TestPortableDesktop_IdleTimeout_MultipleRecordings(t *testing.T) {
 	stopTrap := clk.Trap().NewTimer("agentdesktop", "stop_timeout")
 
 	// Advance past idle timeout.
-	clk.Advance(idleTimeout)
+	clk.Advance(idleTimeout).MustWait(ctx)
 
-	// Wait for both stop timers.
+	// 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.

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

@@ -53,6 +53,8 @@ func workspaceAgent() *serpent.Command {
 		slogJSONPath                   string
 		slogStackdriverPath            string
 		blockFileTransfer              bool
+		blockReversePortForwarding     bool
+		blockLocalPortForwarding       bool
 		agentHeaderCommand             string
 		agentHeader                    []string
 		devcontainers                  bool
@@ -319,10 +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),
@@ -493,6 +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/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/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/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_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/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": [
@@ -13177,6 +13445,12 @@ const docTemplate = `{
                         "$ref": "#/definitions/codersdk.AIBridgeAgenticAction"
                     }
                 },
+                "credential_hint": {
+                    "type": "string"
+                },
+                "credential_kind": {
+                    "type": "string"
+                },
                 "ended_at": {
                     "type": "string",
                     "format": "date-time"
@@ -14175,6 +14449,9 @@ const docTemplate = `{
                 },
                 "count": {
                     "type": "integer"
+                },
+                "count_cap": {
+                    "type": "integer"
                 }
             }
         },
@@ -14414,6 +14691,17 @@ const docTemplate = `{
             "properties": {
                 "acquire_batch_size": {
                     "type": "integer"
+                },
+                "debug_logging_enabled": {
+                    "type": "boolean"
+                }
+            }
+        },
+        "codersdk.ChatRetentionDaysResponse": {
+            "type": "object",
+            "properties": {
+                "retention_days": {
+                    "type": "integer"
                 }
             }
         },
@@ -14496,6 +14784,9 @@ const docTemplate = `{
                 },
                 "count": {
                     "type": "integer"
+                },
+                "count_cap": {
+                    "type": "integer"
                 }
             }
         },
@@ -15066,6 +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": [
@@ -18841,6 +19152,9 @@ const docTemplate = `{
                 "template_version_name": {
                     "type": "string"
                 },
+                "workspace_build_transition": {
+                    "$ref": "#/definitions/codersdk.WorkspaceTransition"
+                },
                 "workspace_id": {
                     "type": "string",
                     "format": "uuid"
@@ -20946,6 +21260,14 @@ const docTemplate = `{
                 }
             }
         },
+        "codersdk.UpdateChatRetentionDaysRequest": {
+            "type": "object",
+            "properties": {
+                "retention_days": {
+                    "type": "integer"
+                }
+            }
+        },
         "codersdk.UpdateCheckResponse": {
             "type": "object",
             "properties": {
@@ -21187,6 +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": {
@@ -21642,6 +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"],
@@ -11755,6 +11993,12 @@
 						"$ref": "#/definitions/codersdk.AIBridgeAgenticAction"
 					}
 				},
+				"credential_hint": {
+					"type": "string"
+				},
+				"credential_kind": {
+					"type": "string"
+				},
 				"ended_at": {
 					"type": "string",
 					"format": "date-time"
@@ -12739,6 +12983,9 @@
 				},
 				"count": {
 					"type": "integer"
+				},
+				"count_cap": {
+					"type": "integer"
 				}
 			}
 		},
@@ -12957,6 +13204,17 @@
 			"properties": {
 				"acquire_batch_size": {
 					"type": "integer"
+				},
+				"debug_logging_enabled": {
+					"type": "boolean"
+				}
+			}
+		},
+		"codersdk.ChatRetentionDaysResponse": {
+			"type": "object",
+			"properties": {
+				"retention_days": {
+					"type": "integer"
 				}
 			}
 		},
@@ -13039,6 +13297,9 @@
 				},
 				"count": {
 					"type": "integer"
+				},
+				"count_cap": {
+					"type": "integer"
 				}
 			}
 		},
@@ -13575,6 +13836,26 @@
 				}
 			}
 		},
+		"codersdk.CreateUserSecretRequest": {
+			"type": "object",
+			"properties": {
+				"description": {
+					"type": "string"
+				},
+				"env_name": {
+					"type": "string"
+				},
+				"file_path": {
+					"type": "string"
+				},
+				"name": {
+					"type": "string"
+				},
+				"value": {
+					"type": "string"
+				}
+			}
+		},
 		"codersdk.CreateWorkspaceBuildReason": {
 			"type": "string",
 			"enum": [
@@ -17231,6 +17512,9 @@
 				"template_version_name": {
 					"type": "string"
 				},
+				"workspace_build_transition": {
+					"$ref": "#/definitions/codersdk.WorkspaceTransition"
+				},
 				"workspace_id": {
 					"type": "string",
 					"format": "uuid"
@@ -19237,6 +19521,14 @@
 				}
 			}
 		},
+		"codersdk.UpdateChatRetentionDaysRequest": {
+			"type": "object",
+			"properties": {
+				"retention_days": {
+					"type": "integer"
+				}
+			}
+		},
 		"codersdk.UpdateCheckResponse": {
 			"type": "object",
 			"properties": {
@@ -19469,6 +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": {
@@ -19899,6 +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/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

@@ -784,6 +784,7 @@ func New(options *Options) *API {
 			SubscribeFn:                    options.ChatSubscribeFn,
 			MaxChatsPerAcquire:             int32(maxChatsPerAcquire), //nolint:gosec // maxChatsPerAcquire is clamped to int32 range above.
 			ProviderAPIKeys:                ChatProviderAPIKeysFromDeploymentValues(options.DeploymentValues),
+			AlwaysEnableDebugLogs:          options.DeploymentValues.AI.Chat.DebugLoggingEnabled.Value(),
 			AgentConn:                      api.agentProvider.AgentConn,
 			AgentInactiveDisconnectTimeout: api.AgentInactiveDisconnectTimeout,
 			InstructionLookupTimeout:       options.ChatdInstructionLookupTimeout,
@@ -1182,6 +1183,10 @@ func New(options *Options) *API {
 				r.Put("/system-prompt", api.putChatSystemPrompt)
 				r.Get("/desktop-enabled", api.getChatDesktopEnabled)
 				r.Put("/desktop-enabled", api.putChatDesktopEnabled)
+				r.Get("/debug-logging", api.getChatDebugLogging)
+				r.Put("/debug-logging", api.putChatDebugLogging)
+				r.Get("/user-debug-logging", api.getUserChatDebugLogging)
+				r.Put("/user-debug-logging", api.putUserChatDebugLogging)
 				r.Get("/user-prompt", api.getUserChatCustomPrompt)
 				r.Put("/user-prompt", api.putUserChatCustomPrompt)
 				r.Get("/user-compaction-thresholds", api.getUserChatCompactionThresholds)
@@ -1189,6 +1194,8 @@ 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)
 			})
@@ -1243,12 +1250,17 @@ 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) {
 					r.Delete("/", api.deleteChatQueuedMessage)
 					r.Post("/promote", api.promoteChatQueuedMessage)
 				})
+				r.Route("/debug", func(r chi.Router) {
+					r.Get("/runs", api.getChatDebugRuns)
+					r.Get("/runs/{debugRun}", api.getChatDebugRun)
+				})
 			})
 		})
 
@@ -1605,6 +1617,15 @@ 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)
@@ -1650,6 +1671,10 @@ 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/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/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:
@@ -1234,6 +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.
@@ -1517,6 +1525,14 @@ func chatMessageParts(m database.ChatMessage) ([]codersdk.ChatMessagePart, error
 	return parts, nil
 }
 
+func nullUUIDPtr(v uuid.NullUUID) *uuid.UUID {
+	if !v.Valid {
+		return nil
+	}
+	value := v.UUID
+	return &value
+}
+
 func nullInt64Ptr(v sql.NullInt64) *int64 {
 	if !v.Valid {
 		return nil
@@ -1525,10 +1541,29 @@ 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{}
@@ -1581,6 +1616,19 @@ 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
@@ -1595,6 +1643,115 @@ 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),
+	}
+}
+
+// ChatDebugRunDetail converts a database.ChatDebugRun and its steps
+// to a codersdk.ChatDebugRun.
+func ChatDebugRunDetail(r database.ChatDebugRun, steps []database.ChatDebugStep) codersdk.ChatDebugRun {
+	sdkSteps := make([]codersdk.ChatDebugStep, 0, len(steps))
+	for _, s := range steps {
+		sdkSteps = append(sdkSteps, ChatDebugStep(s))
+	}
+	return codersdk.ChatDebugRun{
+		ID:                  r.ID,
+		ChatID:              r.ChatID,
+		RootChatID:          nullUUIDPtr(r.RootChatID),
+		ParentChatID:        nullUUIDPtr(r.ParentChatID),
+		ModelConfigID:       nullUUIDPtr(r.ModelConfigID),
+		TriggerMessageID:    nullInt64Ptr(r.TriggerMessageID),
+		HistoryTipMessageID: nullInt64Ptr(r.HistoryTipMessageID),
+		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),
+		Steps:               sdkSteps,
+	}
+}
+
 // 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,
@@ -1604,9 +1761,9 @@ 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
@@ -1699,3 +1856,41 @@ 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()
 
@@ -552,6 +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
@@ -561,14 +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] {
@@ -581,6 +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

@@ -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 {
@@ -1849,6 +1860,28 @@ func (q *querier) DeleteApplicationConnectAPIKeysByUserID(ctx context.Context, u
 	return q.db.DeleteApplicationConnectAPIKeysByUserID(ctx, userID)
 }
 
+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)
+}
+
+func (q *querier) DeleteChatDebugDataByChatID(ctx context.Context, chatID uuid.UUID) (int64, error) {
+	chat, err := q.db.GetChatByID(ctx, chatID)
+	if err != nil {
+		return 0, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
+		return 0, err
+	}
+	return q.db.DeleteChatDebugDataByChatID(ctx, chatID)
+}
+
 func (q *querier) DeleteChatModelConfigByID(ctx context.Context, id uuid.UUID) error {
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceDeploymentConfig); err != nil {
 		return err
@@ -2031,6 +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
@@ -2155,17 +2202,12 @@ func (q *querier) DeleteUserChatProviderKey(ctx context.Context, arg database.De
 	return q.db.DeleteUserChatProviderKey(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)
-	if err != nil {
-		return err
+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
 	}
-
-	if err := q.authorizeContext(ctx, policy.ActionDelete, secret); err != nil {
-		return err
-	}
-	return q.db.DeleteUserSecret(ctx, id)
+	return q.db.DeleteUserSecretByUserIDAndName(ctx, arg)
 }
 
 func (q *querier) DeleteWebpushSubscriptionByUserIDAndEndpoint(ctx context.Context, arg database.DeleteWebpushSubscriptionByUserIDAndEndpointParams) error {
@@ -2327,6 +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 {
@@ -2404,6 +2454,10 @@ func (q *querier) GetActiveAISeatCount(ctx context.Context) (int64, error) {
 	return q.db.GetActiveAISeatCount(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) {
 	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceTemplate.All()); err != nil {
 		return nil, err
@@ -2531,6 +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
@@ -2583,6 +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 {
@@ -2623,6 +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)
@@ -2671,6 +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
@@ -2700,6 +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
@@ -2778,6 +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)
@@ -3340,11 +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) {
@@ -4042,6 +4186,17 @@ 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 {
@@ -4124,19 +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 {
@@ -4801,6 +4943,33 @@ 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) 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)
+}
+
+// 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.ChatDebugStep{}, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
+		return database.ChatDebugStep{}, err
+	}
+	return q.db.InsertChatDebugStep(ctx, arg)
+}
+
 func (q *querier) InsertChatFile(ctx context.Context, arg database.InsertChatFileParams) (database.InsertChatFileRow, error) {
 	// Authorize create on chat resource scoped to the owner and org.
 	return insert(q.log, q.auth, rbac.ResourceChat.WithOwner(arg.OwnerID.String()).InOrg(arg.OrganizationID), q.db.InsertChatFile)(ctx, arg)
@@ -5393,6 +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 {
@@ -5509,7 +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
@@ -5517,6 +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 {
@@ -5674,6 +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)
 }
@@ -5767,15 +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) {
@@ -6617,17 +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) {
@@ -6708,6 +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 {
@@ -6991,6 +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
@@ -7029,6 +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
@@ -7214,6 +7459,17 @@ 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 {

coderd/database/dbauthz/dbauthz_test.go

@@ -400,6 +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()
@@ -450,6 +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()
@@ -467,6 +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(),
@@ -576,6 +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})
@@ -818,15 +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{})
@@ -2203,9 +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) {
@@ -2436,6 +2577,19 @@ func (s *MethodTestSuite) TestUser() {
 		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"}
@@ -2877,6 +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{})
@@ -3972,6 +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()
@@ -5322,19 +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) {
@@ -5346,23 +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

@@ -1597,6 +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"),
 	})
@@ -1643,6 +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{

coderd/database/dbmetrics/querymetrics.go

@@ -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)
@@ -408,6 +416,22 @@ func (m queryMetricsStore) DeleteApplicationConnectAPIKeysByUserID(ctx context.C
 	return r0
 }
 
+func (m queryMetricsStore) DeleteChatDebugDataAfterMessageID(ctx context.Context, arg database.DeleteChatDebugDataAfterMessageIDParams) (int64, error) {
+	start := time.Now()
+	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) DeleteChatDebugDataByChatID(ctx context.Context, chatID uuid.UUID) (int64, error) {
+	start := time.Now()
+	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 {
 	start := time.Now()
 	r0 := m.s.DeleteChatModelConfigByID(ctx, id)
@@ -592,6 +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)
@@ -712,12 +752,12 @@ func (m queryMetricsStore) DeleteUserChatProviderKey(ctx context.Context, arg da
 	return r0
 }
 
-func (m queryMetricsStore) DeleteUserSecret(ctx context.Context, id uuid.UUID) error {
+func (m queryMetricsStore) DeleteUserSecretByUserIDAndName(ctx context.Context, arg database.DeleteUserSecretByUserIDAndNameParams) (int64, 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()
-	return r0
+	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 {
@@ -848,6 +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)
@@ -952,6 +1000,14 @@ func (m queryMetricsStore) GetActiveAISeatCount(ctx context.Context) (int64, err
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetActiveChatsByAgentID(ctx context.Context, agentID uuid.UUID) ([]database.Chat, error) {
+	start := time.Now()
+	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
+}
+
 func (m queryMetricsStore) GetActivePresetPrebuildSchedules(ctx context.Context) ([]database.TemplateVersionPresetPrebuildSchedule, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetActivePresetPrebuildSchedules(ctx)
@@ -1096,6 +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)
@@ -1128,6 +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)
@@ -1152,6 +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)
@@ -1200,6 +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)
@@ -1232,6 +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)
@@ -1304,6 +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)
@@ -1920,11 +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
 }
 
@@ -2544,6 +2672,14 @@ 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)
@@ -2616,14 +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)
@@ -3248,6 +3376,22 @@ func (m queryMetricsStore) InsertChat(ctx context.Context, arg database.InsertCh
 	return r0, r1
 }
 
+func (m queryMetricsStore) InsertChatDebugRun(ctx context.Context, arg database.InsertChatDebugRunParams) (database.ChatDebugRun, error) {
+	start := time.Now()
+	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) InsertChatDebugStep(ctx context.Context, arg database.InsertChatDebugStepParams) (database.ChatDebugStep, error) {
+	start := time.Now()
+	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
+}
+
 func (m queryMetricsStore) InsertChatFile(ctx context.Context, arg database.InsertChatFileParams) (database.InsertChatFileRow, error) {
 	start := time.Now()
 	r0, r1 := m.s.InsertChatFile(ctx, arg)
@@ -3776,6 +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)
@@ -3904,7 +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())
@@ -3912,6 +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)
@@ -4040,6 +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)
@@ -4120,11 +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
 }
 
@@ -4680,11 +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
 }
 
@@ -4752,6 +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)
@@ -4952,6 +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)
@@ -4984,6 +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)
@@ -5176,6 +5384,14 @@ 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)

coderd/database/dbmock/dbmock.go

@@ -363,6 +363,20 @@ func (mr *MockStoreMockRecorder) CleanupDeletedMCPServerIDsFromChats(ctx any) *g
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "CleanupDeletedMCPServerIDsFromChats", reflect.TypeOf((*MockStore)(nil).CleanupDeletedMCPServerIDsFromChats), ctx)
 }
 
+// ClearChatMessageProviderResponseIDsByChatID mocks base method.
+func (m *MockStore) ClearChatMessageProviderResponseIDsByChatID(ctx context.Context, chatID uuid.UUID) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "ClearChatMessageProviderResponseIDsByChatID", ctx, chatID)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// ClearChatMessageProviderResponseIDsByChatID indicates an expected call of ClearChatMessageProviderResponseIDsByChatID.
+func (mr *MockStoreMockRecorder) ClearChatMessageProviderResponseIDsByChatID(ctx, chatID any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "ClearChatMessageProviderResponseIDsByChatID", reflect.TypeOf((*MockStore)(nil).ClearChatMessageProviderResponseIDsByChatID), ctx, chatID)
+}
+
 // CountAIBridgeInterceptions mocks base method.
 func (m *MockStore) CountAIBridgeInterceptions(ctx context.Context, arg database.CountAIBridgeInterceptionsParams) (int64, error) {
 	m.ctrl.T.Helper()
@@ -657,6 +671,36 @@ func (mr *MockStoreMockRecorder) DeleteApplicationConnectAPIKeysByUserID(ctx, us
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteApplicationConnectAPIKeysByUserID", reflect.TypeOf((*MockStore)(nil).DeleteApplicationConnectAPIKeysByUserID), ctx, userID)
 }
 
+// DeleteChatDebugDataAfterMessageID mocks base method.
+func (m *MockStore) DeleteChatDebugDataAfterMessageID(ctx context.Context, arg database.DeleteChatDebugDataAfterMessageIDParams) (int64, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "DeleteChatDebugDataAfterMessageID", ctx, arg)
+	ret0, _ := ret[0].(int64)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// DeleteChatDebugDataAfterMessageID indicates an expected call of DeleteChatDebugDataAfterMessageID.
+func (mr *MockStoreMockRecorder) DeleteChatDebugDataAfterMessageID(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteChatDebugDataAfterMessageID", reflect.TypeOf((*MockStore)(nil).DeleteChatDebugDataAfterMessageID), ctx, arg)
+}
+
+// DeleteChatDebugDataByChatID mocks base method.
+func (m *MockStore) DeleteChatDebugDataByChatID(ctx context.Context, chatID uuid.UUID) (int64, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "DeleteChatDebugDataByChatID", ctx, chatID)
+	ret0, _ := ret[0].(int64)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// DeleteChatDebugDataByChatID indicates an expected call of DeleteChatDebugDataByChatID.
+func (mr *MockStoreMockRecorder) DeleteChatDebugDataByChatID(ctx, chatID any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteChatDebugDataByChatID", reflect.TypeOf((*MockStore)(nil).DeleteChatDebugDataByChatID), ctx, chatID)
+}
+
 // DeleteChatModelConfigByID mocks base method.
 func (m *MockStore) DeleteChatModelConfigByID(ctx context.Context, id uuid.UUID) error {
 	m.ctrl.T.Helper()
@@ -984,6 +1028,36 @@ func (mr *MockStoreMockRecorder) DeleteOldAuditLogs(ctx, arg any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteOldAuditLogs", reflect.TypeOf((*MockStore)(nil).DeleteOldAuditLogs), ctx, arg)
 }
 
+// DeleteOldChatFiles mocks base method.
+func (m *MockStore) DeleteOldChatFiles(ctx context.Context, arg database.DeleteOldChatFilesParams) (int64, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "DeleteOldChatFiles", ctx, arg)
+	ret0, _ := ret[0].(int64)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// DeleteOldChatFiles indicates an expected call of DeleteOldChatFiles.
+func (mr *MockStoreMockRecorder) DeleteOldChatFiles(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteOldChatFiles", reflect.TypeOf((*MockStore)(nil).DeleteOldChatFiles), ctx, arg)
+}
+
+// DeleteOldChats mocks base method.
+func (m *MockStore) DeleteOldChats(ctx context.Context, arg database.DeleteOldChatsParams) (int64, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "DeleteOldChats", ctx, arg)
+	ret0, _ := ret[0].(int64)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// DeleteOldChats indicates an expected call of DeleteOldChats.
+func (mr *MockStoreMockRecorder) DeleteOldChats(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteOldChats", reflect.TypeOf((*MockStore)(nil).DeleteOldChats), ctx, arg)
+}
+
 // DeleteOldConnectionLogs mocks base method.
 func (m *MockStore) DeleteOldConnectionLogs(ctx context.Context, arg database.DeleteOldConnectionLogsParams) (int64, error) {
 	m.ctrl.T.Helper()
@@ -1199,18 +1273,19 @@ func (mr *MockStoreMockRecorder) DeleteUserChatProviderKey(ctx, arg any) *gomock
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteUserChatProviderKey", reflect.TypeOf((*MockStore)(nil).DeleteUserChatProviderKey), ctx, arg)
 }
 
-// DeleteUserSecret mocks base method.
-func (m *MockStore) DeleteUserSecret(ctx context.Context, id uuid.UUID) error {
+// DeleteUserSecretByUserIDAndName mocks base method.
+func (m *MockStore) DeleteUserSecretByUserIDAndName(ctx context.Context, arg database.DeleteUserSecretByUserIDAndNameParams) (int64, error) {
 	m.ctrl.T.Helper()
-	ret := m.ctrl.Call(m, "DeleteUserSecret", ctx, id)
-	ret0, _ := ret[0].(error)
-	return ret0
+	ret := m.ctrl.Call(m, "DeleteUserSecretByUserIDAndName", ctx, arg)
+	ret0, _ := ret[0].(int64)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
 }
 
-// DeleteUserSecret indicates an expected call of DeleteUserSecret.
-func (mr *MockStoreMockRecorder) DeleteUserSecret(ctx, id any) *gomock.Call {
+// DeleteUserSecretByUserIDAndName indicates an expected call of DeleteUserSecretByUserIDAndName.
+func (mr *MockStoreMockRecorder) DeleteUserSecretByUserIDAndName(ctx, arg any) *gomock.Call {
 	mr.mock.ctrl.T.Helper()
-	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteUserSecret", reflect.TypeOf((*MockStore)(nil).DeleteUserSecret), ctx, id)
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteUserSecretByUserIDAndName", reflect.TypeOf((*MockStore)(nil).DeleteUserSecretByUserIDAndName), ctx, arg)
 }
 
 // DeleteWebpushSubscriptionByUserIDAndEndpoint mocks base method.
@@ -1442,6 +1517,21 @@ func (mr *MockStoreMockRecorder) FetchVolumesResourceMonitorsUpdatedAfter(ctx, u
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "FetchVolumesResourceMonitorsUpdatedAfter", reflect.TypeOf((*MockStore)(nil).FetchVolumesResourceMonitorsUpdatedAfter), ctx, updatedAt)
 }
 
+// FinalizeStaleChatDebugRows mocks base method.
+func (m *MockStore) FinalizeStaleChatDebugRows(ctx context.Context, updatedBefore time.Time) (database.FinalizeStaleChatDebugRowsRow, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "FinalizeStaleChatDebugRows", ctx, updatedBefore)
+	ret0, _ := ret[0].(database.FinalizeStaleChatDebugRowsRow)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// FinalizeStaleChatDebugRows indicates an expected call of FinalizeStaleChatDebugRows.
+func (mr *MockStoreMockRecorder) FinalizeStaleChatDebugRows(ctx, updatedBefore any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "FinalizeStaleChatDebugRows", reflect.TypeOf((*MockStore)(nil).FinalizeStaleChatDebugRows), ctx, updatedBefore)
+}
+
 // FindMatchingPresetID mocks base method.
 func (m *MockStore) FindMatchingPresetID(ctx context.Context, arg database.FindMatchingPresetIDParams) (uuid.UUID, error) {
 	m.ctrl.T.Helper()
@@ -1637,6 +1727,21 @@ func (mr *MockStoreMockRecorder) GetActiveAISeatCount(ctx any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetActiveAISeatCount", reflect.TypeOf((*MockStore)(nil).GetActiveAISeatCount), ctx)
 }
 
+// GetActiveChatsByAgentID mocks base method.
+func (m *MockStore) GetActiveChatsByAgentID(ctx context.Context, agentID uuid.UUID) ([]database.Chat, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetActiveChatsByAgentID", ctx, agentID)
+	ret0, _ := ret[0].([]database.Chat)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetActiveChatsByAgentID indicates an expected call of GetActiveChatsByAgentID.
+func (mr *MockStoreMockRecorder) GetActiveChatsByAgentID(ctx, agentID any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetActiveChatsByAgentID", reflect.TypeOf((*MockStore)(nil).GetActiveChatsByAgentID), ctx, agentID)
+}
+
 // GetActivePresetPrebuildSchedules mocks base method.
 func (m *MockStore) GetActivePresetPrebuildSchedules(ctx context.Context) ([]database.TemplateVersionPresetPrebuildSchedule, error) {
 	m.ctrl.T.Helper()
@@ -2012,6 +2117,66 @@ func (mr *MockStoreMockRecorder) GetChatCostSummary(ctx, arg any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatCostSummary", reflect.TypeOf((*MockStore)(nil).GetChatCostSummary), ctx, arg)
 }
 
+// GetChatDebugLoggingAllowUsers mocks base method.
+func (m *MockStore) GetChatDebugLoggingAllowUsers(ctx context.Context) (bool, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatDebugLoggingAllowUsers", ctx)
+	ret0, _ := ret[0].(bool)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatDebugLoggingAllowUsers indicates an expected call of GetChatDebugLoggingAllowUsers.
+func (mr *MockStoreMockRecorder) GetChatDebugLoggingAllowUsers(ctx any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatDebugLoggingAllowUsers", reflect.TypeOf((*MockStore)(nil).GetChatDebugLoggingAllowUsers), ctx)
+}
+
+// GetChatDebugRunByID mocks base method.
+func (m *MockStore) GetChatDebugRunByID(ctx context.Context, id uuid.UUID) (database.ChatDebugRun, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatDebugRunByID", ctx, id)
+	ret0, _ := ret[0].(database.ChatDebugRun)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatDebugRunByID indicates an expected call of GetChatDebugRunByID.
+func (mr *MockStoreMockRecorder) GetChatDebugRunByID(ctx, id any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatDebugRunByID", reflect.TypeOf((*MockStore)(nil).GetChatDebugRunByID), ctx, id)
+}
+
+// GetChatDebugRunsByChatID mocks base method.
+func (m *MockStore) GetChatDebugRunsByChatID(ctx context.Context, arg database.GetChatDebugRunsByChatIDParams) ([]database.ChatDebugRun, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatDebugRunsByChatID", ctx, arg)
+	ret0, _ := ret[0].([]database.ChatDebugRun)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatDebugRunsByChatID indicates an expected call of GetChatDebugRunsByChatID.
+func (mr *MockStoreMockRecorder) GetChatDebugRunsByChatID(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatDebugRunsByChatID", reflect.TypeOf((*MockStore)(nil).GetChatDebugRunsByChatID), ctx, arg)
+}
+
+// GetChatDebugStepsByRunID mocks base method.
+func (m *MockStore) GetChatDebugStepsByRunID(ctx context.Context, runID uuid.UUID) ([]database.ChatDebugStep, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatDebugStepsByRunID", ctx, runID)
+	ret0, _ := ret[0].([]database.ChatDebugStep)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatDebugStepsByRunID indicates an expected call of GetChatDebugStepsByRunID.
+func (mr *MockStoreMockRecorder) GetChatDebugStepsByRunID(ctx, runID any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatDebugStepsByRunID", reflect.TypeOf((*MockStore)(nil).GetChatDebugStepsByRunID), ctx, runID)
+}
+
 // GetChatDesktopEnabled mocks base method.
 func (m *MockStore) GetChatDesktopEnabled(ctx context.Context) (bool, error) {
 	m.ctrl.T.Helper()
@@ -2072,6 +2237,21 @@ func (mr *MockStoreMockRecorder) GetChatFileByID(ctx, id any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatFileByID", reflect.TypeOf((*MockStore)(nil).GetChatFileByID), ctx, id)
 }
 
+// GetChatFileMetadataByChatID mocks base method.
+func (m *MockStore) GetChatFileMetadataByChatID(ctx context.Context, chatID uuid.UUID) ([]database.GetChatFileMetadataByChatIDRow, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatFileMetadataByChatID", ctx, chatID)
+	ret0, _ := ret[0].([]database.GetChatFileMetadataByChatIDRow)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatFileMetadataByChatID indicates an expected call of GetChatFileMetadataByChatID.
+func (mr *MockStoreMockRecorder) GetChatFileMetadataByChatID(ctx, chatID any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatFileMetadataByChatID", reflect.TypeOf((*MockStore)(nil).GetChatFileMetadataByChatID), ctx, chatID)
+}
+
 // GetChatFilesByIDs mocks base method.
 func (m *MockStore) GetChatFilesByIDs(ctx context.Context, ids []uuid.UUID) ([]database.ChatFile, error) {
 	m.ctrl.T.Helper()
@@ -2117,6 +2297,21 @@ func (mr *MockStoreMockRecorder) GetChatMessageByID(ctx, id any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatMessageByID", reflect.TypeOf((*MockStore)(nil).GetChatMessageByID), ctx, id)
 }
 
+// GetChatMessageSummariesPerChat mocks base method.
+func (m *MockStore) GetChatMessageSummariesPerChat(ctx context.Context, createdAfter time.Time) ([]database.GetChatMessageSummariesPerChatRow, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatMessageSummariesPerChat", ctx, createdAfter)
+	ret0, _ := ret[0].([]database.GetChatMessageSummariesPerChatRow)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatMessageSummariesPerChat indicates an expected call of GetChatMessageSummariesPerChat.
+func (mr *MockStoreMockRecorder) GetChatMessageSummariesPerChat(ctx, createdAfter any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatMessageSummariesPerChat", reflect.TypeOf((*MockStore)(nil).GetChatMessageSummariesPerChat), ctx, createdAfter)
+}
+
 // GetChatMessagesByChatID mocks base method.
 func (m *MockStore) GetChatMessagesByChatID(ctx context.Context, arg database.GetChatMessagesByChatIDParams) ([]database.ChatMessage, error) {
 	m.ctrl.T.Helper()
@@ -2207,6 +2402,21 @@ func (mr *MockStoreMockRecorder) GetChatModelConfigs(ctx any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatModelConfigs", reflect.TypeOf((*MockStore)(nil).GetChatModelConfigs), ctx)
 }
 
+// GetChatModelConfigsForTelemetry mocks base method.
+func (m *MockStore) GetChatModelConfigsForTelemetry(ctx context.Context) ([]database.GetChatModelConfigsForTelemetryRow, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatModelConfigsForTelemetry", ctx)
+	ret0, _ := ret[0].([]database.GetChatModelConfigsForTelemetryRow)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatModelConfigsForTelemetry indicates an expected call of GetChatModelConfigsForTelemetry.
+func (mr *MockStoreMockRecorder) GetChatModelConfigsForTelemetry(ctx any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatModelConfigsForTelemetry", reflect.TypeOf((*MockStore)(nil).GetChatModelConfigsForTelemetry), ctx)
+}
+
 // GetChatProviderByID mocks base method.
 func (m *MockStore) GetChatProviderByID(ctx context.Context, id uuid.UUID) (database.ChatProvider, error) {
 	m.ctrl.T.Helper()
@@ -2267,6 +2477,21 @@ func (mr *MockStoreMockRecorder) GetChatQueuedMessages(ctx, chatID any) *gomock.
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatQueuedMessages", reflect.TypeOf((*MockStore)(nil).GetChatQueuedMessages), ctx, chatID)
 }
 
+// GetChatRetentionDays mocks base method.
+func (m *MockStore) GetChatRetentionDays(ctx context.Context) (int32, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatRetentionDays", ctx)
+	ret0, _ := ret[0].(int32)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatRetentionDays indicates an expected call of GetChatRetentionDays.
+func (mr *MockStoreMockRecorder) GetChatRetentionDays(ctx any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatRetentionDays", reflect.TypeOf((*MockStore)(nil).GetChatRetentionDays), ctx)
+}
+
 // GetChatSystemPrompt mocks base method.
 func (m *MockStore) GetChatSystemPrompt(ctx context.Context) (string, error) {
 	m.ctrl.T.Helper()
@@ -2402,6 +2627,21 @@ func (mr *MockStoreMockRecorder) GetChatsByWorkspaceIDs(ctx, ids any) *gomock.Ca
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatsByWorkspaceIDs", reflect.TypeOf((*MockStore)(nil).GetChatsByWorkspaceIDs), ctx, ids)
 }
 
+// GetChatsUpdatedAfter mocks base method.
+func (m *MockStore) GetChatsUpdatedAfter(ctx context.Context, updatedAfter time.Time) ([]database.GetChatsUpdatedAfterRow, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatsUpdatedAfter", ctx, updatedAfter)
+	ret0, _ := ret[0].([]database.GetChatsUpdatedAfterRow)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatsUpdatedAfter indicates an expected call of GetChatsUpdatedAfter.
+func (mr *MockStoreMockRecorder) GetChatsUpdatedAfter(ctx, updatedAfter any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatsUpdatedAfter", reflect.TypeOf((*MockStore)(nil).GetChatsUpdatedAfter), ctx, updatedAfter)
+}
+
 // GetConnectionLogsOffset mocks base method.
 func (m *MockStore) GetConnectionLogsOffset(ctx context.Context, arg database.GetConnectionLogsOffsetParams) ([]database.GetConnectionLogsOffsetRow, error) {
 	m.ctrl.T.Helper()
@@ -3557,19 +3797,19 @@ func (mr *MockStoreMockRecorder) GetPRInsightsPerModel(ctx, arg any) *gomock.Cal
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetPRInsightsPerModel", reflect.TypeOf((*MockStore)(nil).GetPRInsightsPerModel), ctx, arg)
 }
 
-// GetPRInsightsRecentPRs mocks base method.
-func (m *MockStore) GetPRInsightsRecentPRs(ctx context.Context, arg database.GetPRInsightsRecentPRsParams) ([]database.GetPRInsightsRecentPRsRow, error) {
+// GetPRInsightsPullRequests mocks base method.
+func (m *MockStore) GetPRInsightsPullRequests(ctx context.Context, arg database.GetPRInsightsPullRequestsParams) ([]database.GetPRInsightsPullRequestsRow, error) {
 	m.ctrl.T.Helper()
-	ret := m.ctrl.Call(m, "GetPRInsightsRecentPRs", ctx, arg)
-	ret0, _ := ret[0].([]database.GetPRInsightsRecentPRsRow)
+	ret := m.ctrl.Call(m, "GetPRInsightsPullRequests", ctx, arg)
+	ret0, _ := ret[0].([]database.GetPRInsightsPullRequestsRow)
 	ret1, _ := ret[1].(error)
 	return ret0, ret1
 }
 
-// GetPRInsightsRecentPRs indicates an expected call of GetPRInsightsRecentPRs.
-func (mr *MockStoreMockRecorder) GetPRInsightsRecentPRs(ctx, arg any) *gomock.Call {
+// GetPRInsightsPullRequests indicates an expected call of GetPRInsightsPullRequests.
+func (mr *MockStoreMockRecorder) GetPRInsightsPullRequests(ctx, arg any) *gomock.Call {
 	mr.mock.ctrl.T.Helper()
-	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetPRInsightsRecentPRs", reflect.TypeOf((*MockStore)(nil).GetPRInsightsRecentPRs), ctx, arg)
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetPRInsightsPullRequests", reflect.TypeOf((*MockStore)(nil).GetPRInsightsPullRequests), ctx, arg)
 }
 
 // GetPRInsightsSummary mocks base method.
@@ -4757,6 +4997,21 @@ func (mr *MockStoreMockRecorder) GetUserChatCustomPrompt(ctx, userID any) *gomoc
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetUserChatCustomPrompt", reflect.TypeOf((*MockStore)(nil).GetUserChatCustomPrompt), ctx, userID)
 }
 
+// GetUserChatDebugLoggingEnabled mocks base method.
+func (m *MockStore) GetUserChatDebugLoggingEnabled(ctx context.Context, userID uuid.UUID) (bool, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetUserChatDebugLoggingEnabled", ctx, userID)
+	ret0, _ := ret[0].(bool)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetUserChatDebugLoggingEnabled indicates an expected call of GetUserChatDebugLoggingEnabled.
+func (mr *MockStoreMockRecorder) GetUserChatDebugLoggingEnabled(ctx, userID any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetUserChatDebugLoggingEnabled", reflect.TypeOf((*MockStore)(nil).GetUserChatDebugLoggingEnabled), ctx, userID)
+}
+
 // GetUserChatProviderKeys mocks base method.
 func (m *MockStore) GetUserChatProviderKeys(ctx context.Context, userID uuid.UUID) ([]database.UserChatProviderKey, error) {
 	m.ctrl.T.Helper()
@@ -4892,21 +5147,6 @@ func (mr *MockStoreMockRecorder) GetUserNotificationPreferences(ctx, userID any)
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetUserNotificationPreferences", reflect.TypeOf((*MockStore)(nil).GetUserNotificationPreferences), ctx, userID)
 }
 
-// GetUserSecret mocks base method.
-func (m *MockStore) GetUserSecret(ctx context.Context, id uuid.UUID) (database.UserSecret, error) {
-	m.ctrl.T.Helper()
-	ret := m.ctrl.Call(m, "GetUserSecret", ctx, id)
-	ret0, _ := ret[0].(database.UserSecret)
-	ret1, _ := ret[1].(error)
-	return ret0, ret1
-}
-
-// GetUserSecret indicates an expected call of GetUserSecret.
-func (mr *MockStoreMockRecorder) GetUserSecret(ctx, id any) *gomock.Call {
-	mr.mock.ctrl.T.Helper()
-	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetUserSecret", reflect.TypeOf((*MockStore)(nil).GetUserSecret), ctx, id)
-}
-
 // GetUserSecretByUserIDAndName mocks base method.
 func (m *MockStore) GetUserSecretByUserIDAndName(ctx context.Context, arg database.GetUserSecretByUserIDAndNameParams) (database.UserSecret, error) {
 	m.ctrl.T.Helper()
@@ -6091,6 +6331,36 @@ func (mr *MockStoreMockRecorder) InsertChat(ctx, arg any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "InsertChat", reflect.TypeOf((*MockStore)(nil).InsertChat), ctx, arg)
 }
 
+// InsertChatDebugRun mocks base method.
+func (m *MockStore) InsertChatDebugRun(ctx context.Context, arg database.InsertChatDebugRunParams) (database.ChatDebugRun, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "InsertChatDebugRun", ctx, arg)
+	ret0, _ := ret[0].(database.ChatDebugRun)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// InsertChatDebugRun indicates an expected call of InsertChatDebugRun.
+func (mr *MockStoreMockRecorder) InsertChatDebugRun(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "InsertChatDebugRun", reflect.TypeOf((*MockStore)(nil).InsertChatDebugRun), ctx, arg)
+}
+
+// InsertChatDebugStep mocks base method.
+func (m *MockStore) InsertChatDebugStep(ctx context.Context, arg database.InsertChatDebugStepParams) (database.ChatDebugStep, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "InsertChatDebugStep", ctx, arg)
+	ret0, _ := ret[0].(database.ChatDebugStep)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// InsertChatDebugStep indicates an expected call of InsertChatDebugStep.
+func (mr *MockStoreMockRecorder) InsertChatDebugStep(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "InsertChatDebugStep", reflect.TypeOf((*MockStore)(nil).InsertChatDebugStep), ctx, arg)
+}
+
 // InsertChatFile mocks base method.
 func (m *MockStore) InsertChatFile(ctx context.Context, arg database.InsertChatFileParams) (database.InsertChatFileRow, error) {
 	m.ctrl.T.Helper()
@@ -7066,6 +7336,21 @@ func (mr *MockStoreMockRecorder) InsertWorkspaceResourceMetadata(ctx, arg any) *
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "InsertWorkspaceResourceMetadata", reflect.TypeOf((*MockStore)(nil).InsertWorkspaceResourceMetadata), ctx, arg)
 }
 
+// LinkChatFiles mocks base method.
+func (m *MockStore) LinkChatFiles(ctx context.Context, arg database.LinkChatFilesParams) (int32, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "LinkChatFiles", ctx, arg)
+	ret0, _ := ret[0].(int32)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// LinkChatFiles indicates an expected call of LinkChatFiles.
+func (mr *MockStoreMockRecorder) LinkChatFiles(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "LinkChatFiles", reflect.TypeOf((*MockStore)(nil).LinkChatFiles), ctx, arg)
+}
+
 // ListAIBridgeClients mocks base method.
 func (m *MockStore) ListAIBridgeClients(ctx context.Context, arg database.ListAIBridgeClientsParams) ([]string, error) {
 	m.ctrl.T.Helper()
@@ -7382,10 +7667,10 @@ func (mr *MockStoreMockRecorder) ListUserChatCompactionThresholds(ctx, userID an
 }
 
 // ListUserSecrets mocks base method.
-func (m *MockStore) ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]database.UserSecret, error) {
+func (m *MockStore) ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]database.ListUserSecretsRow, error) {
 	m.ctrl.T.Helper()
 	ret := m.ctrl.Call(m, "ListUserSecrets", ctx, userID)
-	ret0, _ := ret[0].([]database.UserSecret)
+	ret0, _ := ret[0].([]database.ListUserSecretsRow)
 	ret1, _ := ret[1].(error)
 	return ret0, ret1
 }
@@ -7396,6 +7681,21 @@ func (mr *MockStoreMockRecorder) ListUserSecrets(ctx, userID any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "ListUserSecrets", reflect.TypeOf((*MockStore)(nil).ListUserSecrets), ctx, userID)
 }
 
+// ListUserSecretsWithValues mocks base method.
+func (m *MockStore) ListUserSecretsWithValues(ctx context.Context, userID uuid.UUID) ([]database.UserSecret, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "ListUserSecretsWithValues", ctx, userID)
+	ret0, _ := ret[0].([]database.UserSecret)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// ListUserSecretsWithValues indicates an expected call of ListUserSecretsWithValues.
+func (mr *MockStoreMockRecorder) ListUserSecretsWithValues(ctx, userID any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "ListUserSecretsWithValues", reflect.TypeOf((*MockStore)(nil).ListUserSecretsWithValues), ctx, userID)
+}
+
 // ListWorkspaceAgentPortShares mocks base method.
 func (m *MockStore) ListWorkspaceAgentPortShares(ctx context.Context, workspaceID uuid.UUID) ([]database.WorkspaceAgentPortShare, error) {
 	m.ctrl.T.Helper()
@@ -7660,6 +7960,20 @@ func (mr *MockStoreMockRecorder) SoftDeleteChatMessagesAfterID(ctx, arg any) *go
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "SoftDeleteChatMessagesAfterID", reflect.TypeOf((*MockStore)(nil).SoftDeleteChatMessagesAfterID), ctx, arg)
 }
 
+// SoftDeleteContextFileMessages mocks base method.
+func (m *MockStore) SoftDeleteContextFileMessages(ctx context.Context, chatID uuid.UUID) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "SoftDeleteContextFileMessages", ctx, chatID)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// SoftDeleteContextFileMessages indicates an expected call of SoftDeleteContextFileMessages.
+func (mr *MockStoreMockRecorder) SoftDeleteContextFileMessages(ctx, chatID any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "SoftDeleteContextFileMessages", reflect.TypeOf((*MockStore)(nil).SoftDeleteContextFileMessages), ctx, chatID)
+}
+
 // TryAcquireLock mocks base method.
 func (m *MockStore) TryAcquireLock(ctx context.Context, pgTryAdvisoryXactLock int64) (bool, error) {
 	m.ctrl.T.Helper()
@@ -7805,19 +8119,49 @@ func (mr *MockStoreMockRecorder) UpdateChatByID(ctx, arg any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateChatByID", reflect.TypeOf((*MockStore)(nil).UpdateChatByID), ctx, arg)
 }
 
-// UpdateChatHeartbeat mocks base method.
-func (m *MockStore) UpdateChatHeartbeat(ctx context.Context, arg database.UpdateChatHeartbeatParams) (int64, error) {
+// UpdateChatDebugRun mocks base method.
+func (m *MockStore) UpdateChatDebugRun(ctx context.Context, arg database.UpdateChatDebugRunParams) (database.ChatDebugRun, error) {
 	m.ctrl.T.Helper()
-	ret := m.ctrl.Call(m, "UpdateChatHeartbeat", ctx, arg)
-	ret0, _ := ret[0].(int64)
+	ret := m.ctrl.Call(m, "UpdateChatDebugRun", ctx, arg)
+	ret0, _ := ret[0].(database.ChatDebugRun)
 	ret1, _ := ret[1].(error)
 	return ret0, ret1
 }
 
-// UpdateChatHeartbeat indicates an expected call of UpdateChatHeartbeat.
-func (mr *MockStoreMockRecorder) UpdateChatHeartbeat(ctx, arg any) *gomock.Call {
+// UpdateChatDebugRun indicates an expected call of UpdateChatDebugRun.
+func (mr *MockStoreMockRecorder) UpdateChatDebugRun(ctx, arg any) *gomock.Call {
 	mr.mock.ctrl.T.Helper()
-	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateChatHeartbeat", reflect.TypeOf((*MockStore)(nil).UpdateChatHeartbeat), ctx, arg)
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateChatDebugRun", reflect.TypeOf((*MockStore)(nil).UpdateChatDebugRun), ctx, arg)
+}
+
+// UpdateChatDebugStep mocks base method.
+func (m *MockStore) UpdateChatDebugStep(ctx context.Context, arg database.UpdateChatDebugStepParams) (database.ChatDebugStep, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "UpdateChatDebugStep", ctx, arg)
+	ret0, _ := ret[0].(database.ChatDebugStep)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// UpdateChatDebugStep indicates an expected call of UpdateChatDebugStep.
+func (mr *MockStoreMockRecorder) UpdateChatDebugStep(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateChatDebugStep", reflect.TypeOf((*MockStore)(nil).UpdateChatDebugStep), ctx, arg)
+}
+
+// UpdateChatHeartbeats mocks base method.
+func (m *MockStore) UpdateChatHeartbeats(ctx context.Context, arg database.UpdateChatHeartbeatsParams) ([]uuid.UUID, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "UpdateChatHeartbeats", ctx, arg)
+	ret0, _ := ret[0].([]uuid.UUID)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// UpdateChatHeartbeats indicates an expected call of UpdateChatHeartbeats.
+func (mr *MockStoreMockRecorder) UpdateChatHeartbeats(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateChatHeartbeats", reflect.TypeOf((*MockStore)(nil).UpdateChatHeartbeats), ctx, arg)
 }
 
 // UpdateChatLabelsByID mocks base method.
@@ -8824,19 +9168,19 @@ func (mr *MockStoreMockRecorder) UpdateUserRoles(ctx, arg any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateUserRoles", reflect.TypeOf((*MockStore)(nil).UpdateUserRoles), ctx, arg)
 }
 
-// UpdateUserSecret mocks base method.
-func (m *MockStore) UpdateUserSecret(ctx context.Context, arg database.UpdateUserSecretParams) (database.UserSecret, error) {
+// UpdateUserSecretByUserIDAndName mocks base method.
+func (m *MockStore) UpdateUserSecretByUserIDAndName(ctx context.Context, arg database.UpdateUserSecretByUserIDAndNameParams) (database.UserSecret, error) {
 	m.ctrl.T.Helper()
-	ret := m.ctrl.Call(m, "UpdateUserSecret", ctx, arg)
+	ret := m.ctrl.Call(m, "UpdateUserSecretByUserIDAndName", ctx, arg)
 	ret0, _ := ret[0].(database.UserSecret)
 	ret1, _ := ret[1].(error)
 	return ret0, ret1
 }
 
-// UpdateUserSecret indicates an expected call of UpdateUserSecret.
-func (mr *MockStoreMockRecorder) UpdateUserSecret(ctx, arg any) *gomock.Call {
+// UpdateUserSecretByUserIDAndName indicates an expected call of UpdateUserSecretByUserIDAndName.
+func (mr *MockStoreMockRecorder) UpdateUserSecretByUserIDAndName(ctx, arg any) *gomock.Call {
 	mr.mock.ctrl.T.Helper()
-	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateUserSecret", reflect.TypeOf((*MockStore)(nil).UpdateUserSecret), ctx, arg)
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateUserSecretByUserIDAndName", reflect.TypeOf((*MockStore)(nil).UpdateUserSecretByUserIDAndName), ctx, arg)
 }
 
 // UpdateUserStatus mocks base method.
@@ -8956,6 +9300,20 @@ func (mr *MockStoreMockRecorder) UpdateWorkspaceAgentConnectionByID(ctx, arg any
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateWorkspaceAgentConnectionByID", reflect.TypeOf((*MockStore)(nil).UpdateWorkspaceAgentConnectionByID), ctx, arg)
 }
 
+// UpdateWorkspaceAgentDirectoryByID mocks base method.
+func (m *MockStore) UpdateWorkspaceAgentDirectoryByID(ctx context.Context, arg database.UpdateWorkspaceAgentDirectoryByIDParams) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "UpdateWorkspaceAgentDirectoryByID", ctx, arg)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// UpdateWorkspaceAgentDirectoryByID indicates an expected call of UpdateWorkspaceAgentDirectoryByID.
+func (mr *MockStoreMockRecorder) UpdateWorkspaceAgentDirectoryByID(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateWorkspaceAgentDirectoryByID", reflect.TypeOf((*MockStore)(nil).UpdateWorkspaceAgentDirectoryByID), ctx, arg)
+}
+
 // UpdateWorkspaceAgentDisplayAppsByID mocks base method.
 func (m *MockStore) UpdateWorkspaceAgentDisplayAppsByID(ctx context.Context, arg database.UpdateWorkspaceAgentDisplayAppsByIDParams) error {
 	m.ctrl.T.Helper()
@@ -9311,6 +9669,20 @@ func (mr *MockStoreMockRecorder) UpsertBoundaryUsageStats(ctx, arg any) *gomock.
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpsertBoundaryUsageStats", reflect.TypeOf((*MockStore)(nil).UpsertBoundaryUsageStats), ctx, arg)
 }
 
+// UpsertChatDebugLoggingAllowUsers mocks base method.
+func (m *MockStore) UpsertChatDebugLoggingAllowUsers(ctx context.Context, allowUsers bool) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "UpsertChatDebugLoggingAllowUsers", ctx, allowUsers)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// UpsertChatDebugLoggingAllowUsers indicates an expected call of UpsertChatDebugLoggingAllowUsers.
+func (mr *MockStoreMockRecorder) UpsertChatDebugLoggingAllowUsers(ctx, allowUsers any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpsertChatDebugLoggingAllowUsers", reflect.TypeOf((*MockStore)(nil).UpsertChatDebugLoggingAllowUsers), ctx, allowUsers)
+}
+
 // UpsertChatDesktopEnabled mocks base method.
 func (m *MockStore) UpsertChatDesktopEnabled(ctx context.Context, enableDesktop bool) error {
 	m.ctrl.T.Helper()
@@ -9369,6 +9741,20 @@ func (mr *MockStoreMockRecorder) UpsertChatIncludeDefaultSystemPrompt(ctx, inclu
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpsertChatIncludeDefaultSystemPrompt", reflect.TypeOf((*MockStore)(nil).UpsertChatIncludeDefaultSystemPrompt), ctx, includeDefaultSystemPrompt)
 }
 
+// UpsertChatRetentionDays mocks base method.
+func (m *MockStore) UpsertChatRetentionDays(ctx context.Context, retentionDays int32) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "UpsertChatRetentionDays", ctx, retentionDays)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// UpsertChatRetentionDays indicates an expected call of UpsertChatRetentionDays.
+func (mr *MockStoreMockRecorder) UpsertChatRetentionDays(ctx, retentionDays any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpsertChatRetentionDays", reflect.TypeOf((*MockStore)(nil).UpsertChatRetentionDays), ctx, retentionDays)
+}
+
 // UpsertChatSystemPrompt mocks base method.
 func (m *MockStore) UpsertChatSystemPrompt(ctx context.Context, value string) error {
 	m.ctrl.T.Helper()
@@ -9714,6 +10100,20 @@ func (mr *MockStoreMockRecorder) UpsertTemplateUsageStats(ctx any) *gomock.Call
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpsertTemplateUsageStats", reflect.TypeOf((*MockStore)(nil).UpsertTemplateUsageStats), ctx)
 }
 
+// UpsertUserChatDebugLoggingEnabled mocks base method.
+func (m *MockStore) UpsertUserChatDebugLoggingEnabled(ctx context.Context, arg database.UpsertUserChatDebugLoggingEnabledParams) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "UpsertUserChatDebugLoggingEnabled", ctx, arg)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// UpsertUserChatDebugLoggingEnabled indicates an expected call of UpsertUserChatDebugLoggingEnabled.
+func (mr *MockStoreMockRecorder) UpsertUserChatDebugLoggingEnabled(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpsertUserChatDebugLoggingEnabled", reflect.TypeOf((*MockStore)(nil).UpsertUserChatDebugLoggingEnabled), ctx, arg)
+}
+
 // UpsertUserChatProviderKey mocks base method.
 func (m *MockStore) UpsertUserChatProviderKey(ctx context.Context, arg database.UpsertUserChatProviderKeyParams) (database.UserChatProviderKey, error) {
 	m.ctrl.T.Helper()

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

@@ -293,7 +293,8 @@ CREATE TYPE chat_status AS ENUM (
     'running',
     'paused',
     'completed',
-    'error'
+    'error',
+    'requires_action'
 );
 
 CREATE TYPE connection_status AS ENUM (
@@ -315,6 +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',
@@ -1101,7 +1107,9 @@ CREATE TABLE aibridge_interceptions (
     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,
-    provider_name text DEFAULT ''::text 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';
@@ -1118,6 +1126,10 @@ COMMENT ON COLUMN aibridge_interceptions.session_id IS 'Groups related intercept
 
 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,
@@ -1243,6 +1255,44 @@ 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_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,
+    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
+);
+
+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,
     url text,
@@ -1269,6 +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,
@@ -1413,7 +1468,8 @@ CREATE TABLE chats (
     agent_id uuid,
     pin_order integer DEFAULT 0 NOT NULL,
     last_read_message_id bigint,
-    last_injected_context jsonb
+    last_injected_context jsonb,
+    dynamic_tools jsonb
 );
 
 CREATE TABLE connection_logs (
@@ -3341,9 +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_debug_runs
+    ADD CONSTRAINT chat_debug_runs_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);
 
@@ -3732,8 +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_debug_runs_chat_started ON chat_debug_runs USING btree (chat_id, started_at DESC);
+
+CREATE UNIQUE INDEX idx_chat_debug_runs_id_chat ON chat_debug_runs USING btree (id, chat_id);
+
+CREATE INDEX idx_chat_debug_runs_stale ON chat_debug_runs USING btree (updated_at) WHERE (finished_at IS NULL);
+
+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_debug_steps_chat_tip ON chat_debug_steps USING btree (chat_id, history_tip_message_id);
+
+CREATE UNIQUE INDEX idx_chat_debug_steps_run_step ON chat_debug_steps USING btree (run_id, step_number);
+
+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);
@@ -3760,14 +3841,14 @@ 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_agent_id ON chats USING btree (agent_id) WHERE (agent_id IS NOT NULL);
+
 CREATE INDEX idx_chats_labels ON chats USING gin (labels);
 
 CREATE INDEX idx_chats_last_model_config_id ON chats USING btree (last_model_config_id);
 
 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);
@@ -4033,9 +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_debug_runs
+    ADD CONSTRAINT chat_debug_runs_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(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;
 
@@ -4099,6 +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;
 

coderd/database/foreign_key_constraint.go

@@ -9,7 +9,11 @@ const (
 	ForeignKeyAiSeatStateUserID                                   ForeignKeyConstraint = "ai_seat_state_user_id_fkey"                                      // ALTER TABLE ONLY ai_seat_state ADD CONSTRAINT ai_seat_state_user_id_fkey FOREIGN KEY (user_id) REFERENCES users(id) ON DELETE CASCADE;
 	ForeignKeyAibridgeInterceptionsInitiatorID                    ForeignKeyConstraint = "aibridge_interceptions_initiator_id_fkey"                        // ALTER TABLE ONLY aibridge_interceptions ADD CONSTRAINT aibridge_interceptions_initiator_id_fkey FOREIGN KEY (initiator_id) REFERENCES users(id);
 	ForeignKeyAPIKeysUserIDUUID                                   ForeignKeyConstraint = "api_keys_user_id_uuid_fkey"                                      // ALTER TABLE ONLY api_keys ADD CONSTRAINT api_keys_user_id_uuid_fkey FOREIGN KEY (user_id) REFERENCES users(id) ON DELETE CASCADE;
+	ForeignKeyChatDebugRunsChatID                                 ForeignKeyConstraint = "chat_debug_runs_chat_id_fkey"                                    // ALTER TABLE ONLY chat_debug_runs ADD CONSTRAINT chat_debug_runs_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
+	ForeignKeyChatDebugStepsChatID                                ForeignKeyConstraint = "chat_debug_steps_chat_id_fkey"                                   // ALTER TABLE ONLY chat_debug_steps ADD CONSTRAINT chat_debug_steps_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
 	ForeignKeyChatDiffStatusesChatID                              ForeignKeyConstraint = "chat_diff_statuses_chat_id_fkey"                                 // ALTER TABLE ONLY chat_diff_statuses ADD CONSTRAINT chat_diff_statuses_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
+	ForeignKeyChatFileLinksChatID                                 ForeignKeyConstraint = "chat_file_links_chat_id_fkey"                                    // ALTER TABLE ONLY chat_file_links ADD CONSTRAINT chat_file_links_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
+	ForeignKeyChatFileLinksFileID                                 ForeignKeyConstraint = "chat_file_links_file_id_fkey"                                    // 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;
 	ForeignKeyChatFilesOrganizationID                             ForeignKeyConstraint = "chat_files_organization_id_fkey"                                 // ALTER TABLE ONLY chat_files ADD CONSTRAINT chat_files_organization_id_fkey FOREIGN KEY (organization_id) REFERENCES organizations(id) ON DELETE CASCADE;
 	ForeignKeyChatFilesOwnerID                                    ForeignKeyConstraint = "chat_files_owner_id_fkey"                                        // ALTER TABLE ONLY chat_files ADD CONSTRAINT chat_files_owner_id_fkey FOREIGN KEY (owner_id) REFERENCES users(id) ON DELETE CASCADE;
 	ForeignKeyChatMessagesChatID                                  ForeignKeyConstraint = "chat_messages_chat_id_fkey"                                      // ALTER TABLE ONLY chat_messages ADD CONSTRAINT chat_messages_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
@@ -31,6 +35,7 @@ const (
 	ForeignKeyConnectionLogsWorkspaceID                           ForeignKeyConstraint = "connection_logs_workspace_id_fkey"                               // ALTER TABLE ONLY connection_logs ADD CONSTRAINT connection_logs_workspace_id_fkey FOREIGN KEY (workspace_id) REFERENCES workspaces(id) ON DELETE CASCADE;
 	ForeignKeyConnectionLogsWorkspaceOwnerID                      ForeignKeyConstraint = "connection_logs_workspace_owner_id_fkey"                         // ALTER TABLE ONLY connection_logs ADD CONSTRAINT connection_logs_workspace_owner_id_fkey FOREIGN KEY (workspace_owner_id) REFERENCES users(id) ON DELETE CASCADE;
 	ForeignKeyCryptoKeysSecretKeyID                               ForeignKeyConstraint = "crypto_keys_secret_key_id_fkey"                                  // ALTER TABLE ONLY crypto_keys ADD CONSTRAINT crypto_keys_secret_key_id_fkey FOREIGN KEY (secret_key_id) REFERENCES dbcrypt_keys(active_key_digest);
+	ForeignKeyFkChatDebugStepsRunChat                             ForeignKeyConstraint = "fk_chat_debug_steps_run_chat"                                    // 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;
 	ForeignKeyFkOauth2ProviderAppTokensUserID                     ForeignKeyConstraint = "fk_oauth2_provider_app_tokens_user_id"                           // 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;
 	ForeignKeyGitAuthLinksOauthAccessTokenKeyID                   ForeignKeyConstraint = "git_auth_links_oauth_access_token_key_id_fkey"                   // ALTER TABLE ONLY external_auth_links ADD CONSTRAINT git_auth_links_oauth_access_token_key_id_fkey FOREIGN KEY (oauth_access_token_key_id) REFERENCES dbcrypt_keys(active_key_digest);
 	ForeignKeyGitAuthLinksOauthRefreshTokenKeyID                  ForeignKeyConstraint = "git_auth_links_oauth_refresh_token_key_id_fkey"                  // ALTER TABLE ONLY external_auth_links ADD CONSTRAINT git_auth_links_oauth_refresh_token_key_id_fkey FOREIGN KEY (oauth_refresh_token_key_id) REFERENCES dbcrypt_keys(active_key_digest);

coderd/database/migrations/000462_chat_file_links.down.sql

@@ -0,0 +1,9 @@
+ALTER TABLE chats ADD COLUMN file_ids uuid[] DEFAULT '{}'::uuid[] NOT NULL;
+
+UPDATE chats SET file_ids = (
+    SELECT COALESCE(array_agg(cfl.file_id), '{}')
+    FROM chat_file_links cfl
+    WHERE cfl.chat_id = chats.id
+);
+
+DROP TABLE chat_file_links;

coderd/database/migrations/000462_chat_file_links.up.sql

@@ -0,0 +1,17 @@
+CREATE TABLE chat_file_links (
+    chat_id uuid NOT NULL,
+    file_id uuid NOT NULL,
+    UNIQUE (chat_id, file_id)
+);
+
+CREATE INDEX idx_chat_file_links_chat_id ON chat_file_links (chat_id);
+
+ALTER TABLE chat_file_links
+    ADD CONSTRAINT chat_file_links_chat_id_fkey
+    FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
+
+ALTER TABLE chat_file_links
+    ADD CONSTRAINT chat_file_links_file_id_fkey
+    FOREIGN KEY (file_id) REFERENCES chat_files(id) ON DELETE CASCADE;
+
+ALTER TABLE chats DROP COLUMN IF EXISTS file_ids;

coderd/database/migrations/000463_chat_dynamic_tools.down.sql

@@ -0,0 +1,31 @@
+-- First update any rows using the value we're about to remove.
+-- The column type is still the original chat_status at this point.
+UPDATE chats SET status = 'error' WHERE status = 'requires_action';
+
+-- Drop the column (this is independent of the enum).
+ALTER TABLE chats DROP COLUMN IF EXISTS dynamic_tools;
+
+-- Drop the partial index that references the chat_status enum type.
+-- It must be removed before the rename-create-cast-drop cycle
+-- because the index's WHERE clause (status = 'pending'::chat_status)
+-- would otherwise cause a cross-type comparison failure.
+DROP INDEX IF EXISTS idx_chats_pending;
+
+-- Now recreate the enum without requires_action.
+-- We must use the rename-create-cast-drop pattern.
+ALTER TYPE chat_status RENAME TO chat_status_old;
+CREATE TYPE chat_status AS ENUM (
+    'waiting',
+    'pending',
+    'running',
+    'paused',
+    'completed',
+    'error'
+);
+ALTER TABLE chats ALTER COLUMN status DROP DEFAULT;
+ALTER TABLE chats ALTER COLUMN status TYPE chat_status USING status::text::chat_status;
+ALTER TABLE chats ALTER COLUMN status SET DEFAULT 'waiting';
+DROP TYPE chat_status_old;
+
+-- Recreate the partial index.
+CREATE INDEX idx_chats_pending ON chats USING btree (status) WHERE (status = 'pending'::chat_status);

coderd/database/migrations/000463_chat_dynamic_tools.up.sql

@@ -0,0 +1,3 @@
+ALTER TYPE chat_status ADD VALUE IF NOT EXISTS 'requires_action';
+
+ALTER TABLE chats ADD COLUMN dynamic_tools JSONB DEFAULT NULL;

coderd/database/migrations/000464_aibridge_credential_kind.down.sql

@@ -0,0 +1,5 @@
+ALTER TABLE aibridge_interceptions
+    DROP COLUMN IF EXISTS credential_kind,
+    DROP COLUMN IF EXISTS credential_hint;
+
+DROP TYPE IF EXISTS credential_kind;

coderd/database/migrations/000464_aibridge_credential_kind.up.sql

@@ -0,0 +1,12 @@
+CREATE TYPE credential_kind AS ENUM ('centralized', 'byok');
+
+-- Records how each LLM request was authenticated and a masked credential
+-- identifier for audit purposes. Existing rows default to 'centralized'
+-- with an empty hint since we cannot retroactively determine their values.
+ALTER TABLE aibridge_interceptions
+    ADD COLUMN credential_kind credential_kind NOT NULL DEFAULT 'centralized',
+    -- Length capped as a safety measure to ensure only masked values are stored.
+    ADD COLUMN credential_hint CHARACTER VARYING(15) NOT NULL DEFAULT '';
+
+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).';

coderd/database/migrations/000465_chat_agent_id_index.down.sql

@@ -0,0 +1 @@
+DROP INDEX IF EXISTS idx_chats_agent_id;

coderd/database/migrations/000465_chat_agent_id_index.up.sql

@@ -0,0 +1 @@
+CREATE INDEX idx_chats_agent_id ON chats(agent_id) WHERE agent_id IS NOT NULL;

coderd/database/migrations/000466_drop_chat_pagination_index.down.sql

@@ -0,0 +1 @@
+CREATE INDEX idx_chats_owner_updated_id ON chats (owner_id, updated_at DESC, id DESC);

coderd/database/migrations/000466_drop_chat_pagination_index.up.sql

@@ -0,0 +1,5 @@
+-- The GetChats ORDER BY changed from (updated_at, id) DESC to a 4-column
+-- expression sort (pinned-first flag, negated pin_order, updated_at, id).
+-- This index was purpose-built for the old sort and no longer provides
+-- read benefit. The simpler idx_chats_owner covers the owner_id filter.
+DROP INDEX IF EXISTS idx_chats_owner_updated_id;

coderd/database/migrations/000467_chat_debug_runs_and_steps.down.sql

@@ -0,0 +1,2 @@
+DROP TABLE IF EXISTS chat_debug_steps;
+DROP TABLE IF EXISTS chat_debug_runs;

coderd/database/migrations/000467_chat_debug_runs_and_steps.up.sql

@@ -0,0 +1,59 @@
+CREATE TABLE chat_debug_runs (
+    id                     UUID        PRIMARY KEY DEFAULT gen_random_uuid(),
+    chat_id                UUID        NOT NULL REFERENCES chats(id) ON DELETE CASCADE,
+    -- root_chat_id and parent_chat_id are intentionally NOT
+    -- foreign-keyed to chats(id). They are snapshot values that
+    -- record the subchat hierarchy at run time. The referenced
+    -- chat may be archived or deleted independently, and we want
+    -- to preserve the historical lineage in debug rows rather
+    -- than cascade-delete them.
+    root_chat_id           UUID,
+    parent_chat_id         UUID,
+    model_config_id        UUID,
+    trigger_message_id     BIGINT,
+    history_tip_message_id BIGINT,
+    kind                   TEXT        NOT NULL,
+    status                 TEXT        NOT NULL,
+    provider               TEXT,
+    model                  TEXT,
+    summary                JSONB       NOT NULL DEFAULT '{}'::jsonb,
+    started_at             TIMESTAMPTZ NOT NULL DEFAULT NOW(),
+    updated_at             TIMESTAMPTZ NOT NULL DEFAULT NOW(),
+    finished_at            TIMESTAMPTZ
+);
+
+CREATE UNIQUE INDEX idx_chat_debug_runs_id_chat ON chat_debug_runs(id, chat_id);
+CREATE INDEX idx_chat_debug_runs_chat_started ON chat_debug_runs(chat_id, started_at DESC);
+
+CREATE TABLE chat_debug_steps (
+    id                     UUID        PRIMARY KEY DEFAULT gen_random_uuid(),
+    run_id                 UUID        NOT NULL,
+    chat_id                UUID        NOT NULL REFERENCES chats(id) ON DELETE CASCADE,
+    step_number            INT         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       NOT NULL DEFAULT '[]'::jsonb,
+    error                  JSONB,
+    metadata               JSONB       NOT NULL DEFAULT '{}'::jsonb,
+    started_at             TIMESTAMPTZ NOT NULL DEFAULT NOW(),
+    updated_at             TIMESTAMPTZ NOT NULL DEFAULT NOW(),
+    finished_at            TIMESTAMPTZ,
+    CONSTRAINT fk_chat_debug_steps_run_chat
+        FOREIGN KEY (run_id, chat_id)
+        REFERENCES chat_debug_runs(id, chat_id)
+        ON DELETE CASCADE
+);
+
+CREATE UNIQUE INDEX idx_chat_debug_steps_run_step ON chat_debug_steps(run_id, step_number);
+CREATE INDEX idx_chat_debug_steps_chat_tip ON chat_debug_steps(chat_id, history_tip_message_id);
+-- Supports DeleteChatDebugDataAfterMessageID assistant_message_id branch.
+CREATE INDEX idx_chat_debug_steps_chat_assistant_msg ON chat_debug_steps(chat_id, assistant_message_id) WHERE assistant_message_id IS NOT NULL;
+
+-- Supports FinalizeStaleChatDebugRows worker query.
+CREATE INDEX idx_chat_debug_runs_stale ON chat_debug_runs(updated_at) WHERE finished_at IS NULL;
+CREATE INDEX idx_chat_debug_steps_stale ON chat_debug_steps(updated_at) WHERE finished_at IS NULL;

coderd/database/migrations/testdata/fixtures/000462_chat_file_links.up.sql

@@ -0,0 +1,5 @@
+INSERT INTO chat_file_links (chat_id, file_id)
+VALUES (
+    '72c0438a-18eb-4688-ab80-e4c6a126ef96',
+    '00000000-0000-0000-0000-000000000099'
+);

coderd/database/migrations/testdata/fixtures/000467_chat_debug_runs_and_steps.up.sql

@@ -0,0 +1,65 @@
+INSERT INTO chat_debug_runs (
+    id,
+    chat_id,
+    model_config_id,
+    history_tip_message_id,
+    kind,
+    status,
+    provider,
+    model,
+    summary,
+    started_at,
+    updated_at,
+    finished_at
+) VALUES (
+    'c98518f8-9fb3-458b-a642-57552af1db63',
+    '72c0438a-18eb-4688-ab80-e4c6a126ef96',
+    '9af5f8d5-6a57-4505-8a69-3d6c787b95fd',
+    (SELECT MAX(id) FROM chat_messages WHERE chat_id = '72c0438a-18eb-4688-ab80-e4c6a126ef96'),
+    'chat_turn',
+    'completed',
+    'openai',
+    'gpt-5.2',
+    '{"step_count":1,"has_error":false}'::jsonb,
+    '2024-01-01 00:00:00+00',
+    '2024-01-01 00:00:01+00',
+    '2024-01-01 00:00:01+00'
+);
+
+INSERT INTO chat_debug_steps (
+    id,
+    run_id,
+    chat_id,
+    step_number,
+    operation,
+    status,
+    history_tip_message_id,
+    assistant_message_id,
+    normalized_request,
+    normalized_response,
+    usage,
+    attempts,
+    error,
+    metadata,
+    started_at,
+    updated_at,
+    finished_at
+) VALUES (
+    '59471c60-7851-4fa6-bf05-e21dd939721f',
+    'c98518f8-9fb3-458b-a642-57552af1db63',
+    '72c0438a-18eb-4688-ab80-e4c6a126ef96',
+    1,
+    'stream',
+    'completed',
+    (SELECT MAX(id) FROM chat_messages WHERE chat_id = '72c0438a-18eb-4688-ab80-e4c6a126ef96'),
+    (SELECT MAX(id) FROM chat_messages WHERE chat_id = '72c0438a-18eb-4688-ab80-e4c6a126ef96'),
+    '{"messages":[]}'::jsonb,
+    '{"finish_reason":"stop"}'::jsonb,
+    '{"input_tokens":1,"output_tokens":1}'::jsonb,
+    '[]'::jsonb,
+    NULL,
+    '{"provider":"openai"}'::jsonb,
+    '2024-01-01 00:00:00+00',
+    '2024-01-01 00:00:01+00',
+    '2024-01-01 00:00:01+00'
+);

coderd/database/modelmethods.go

@@ -187,6 +187,10 @@ func (c ChatFile) RBACObject() rbac.Object {
 	return rbac.ResourceChat.WithID(c.ID).WithOwner(c.OwnerID.String()).InOrg(c.OrganizationID)
 }
 
+func (c GetChatFileMetadataByChatIDRow) RBACObject() rbac.Object {
+	return rbac.ResourceChat.WithID(c.ID).WithOwner(c.OwnerID.String()).InOrg(c.OrganizationID)
+}
+
 func (s APIKeyScope) ToRBAC() rbac.ScopeName {
 	switch s {
 	case ApiKeyScopeCoderAll:

coderd/database/modelqueries.go

@@ -584,6 +584,7 @@ func (q *sqlQuerier) CountAuthorizedAuditLogs(ctx context.Context, arg CountAudi
 		arg.DateTo,
 		arg.BuildReason,
 		arg.RequestID,
+		arg.CountCap,
 	)
 	if err != nil {
 		return 0, err
@@ -720,6 +721,7 @@ func (q *sqlQuerier) CountAuthorizedConnectionLogs(ctx context.Context, arg Coun
 		arg.WorkspaceID,
 		arg.ConnectionID,
 		arg.Status,
+		arg.CountCap,
 	)
 	if err != nil {
 		return 0, err
@@ -796,6 +798,7 @@ func (q *sqlQuerier) GetAuthorizedChats(ctx context.Context, arg GetChatsParams,
 			&i.Chat.PinOrder,
 			&i.Chat.LastReadMessageID,
 			&i.Chat.LastInjectedContext,
+			&i.Chat.DynamicTools,
 			&i.HasUnread); err != nil {
 			return nil, err
 		}
@@ -866,6 +869,8 @@ func (q *sqlQuerier) ListAuthorizedAIBridgeInterceptions(ctx context.Context, ar
 			&i.AIBridgeInterception.ClientSessionID,
 			&i.AIBridgeInterception.SessionID,
 			&i.AIBridgeInterception.ProviderName,
+			&i.AIBridgeInterception.CredentialKind,
+			&i.AIBridgeInterception.CredentialHint,
 			&i.VisibleUser.ID,
 			&i.VisibleUser.Username,
 			&i.VisibleUser.Name,
@@ -1129,6 +1134,8 @@ func (q *sqlQuerier) ListAuthorizedAIBridgeSessionThreads(ctx context.Context, a
 			&i.AIBridgeInterception.ClientSessionID,
 			&i.AIBridgeInterception.SessionID,
 			&i.AIBridgeInterception.ProviderName,
+			&i.AIBridgeInterception.CredentialKind,
+			&i.AIBridgeInterception.CredentialHint,
 		); err != nil {
 			return nil, err
 		}

coderd/database/modelqueries_internal_test.go

@@ -145,5 +145,13 @@ func extractWhereClause(query string) string {
 	// Remove SQL comments
 	whereClause = regexp.MustCompile(`(?m)--.*$`).ReplaceAllString(whereClause, "")
 
+	// Normalize indentation so subquery wrapping doesn't cause
+	// mismatches.
+	lines := strings.Split(whereClause, "\n")
+	for i, line := range lines {
+		lines[i] = strings.TrimLeft(line, " \t")
+	}
+	whereClause = strings.Join(lines, "\n")
+
 	return strings.TrimSpace(whereClause)
 }

coderd/database/models.go

@@ -1290,12 +1290,13 @@ func AllChatModeValues() []ChatMode {
 type ChatStatus string
 
 const (
-	ChatStatusWaiting   ChatStatus = "waiting"
-	ChatStatusPending   ChatStatus = "pending"
-	ChatStatusRunning   ChatStatus = "running"
-	ChatStatusPaused    ChatStatus = "paused"
-	ChatStatusCompleted ChatStatus = "completed"
-	ChatStatusError     ChatStatus = "error"
+	ChatStatusWaiting        ChatStatus = "waiting"
+	ChatStatusPending        ChatStatus = "pending"
+	ChatStatusRunning        ChatStatus = "running"
+	ChatStatusPaused         ChatStatus = "paused"
+	ChatStatusCompleted      ChatStatus = "completed"
+	ChatStatusError          ChatStatus = "error"
+	ChatStatusRequiresAction ChatStatus = "requires_action"
 )
 
 func (e *ChatStatus) Scan(src interface{}) error {
@@ -1340,7 +1341,8 @@ func (e ChatStatus) Valid() bool {
 		ChatStatusRunning,
 		ChatStatusPaused,
 		ChatStatusCompleted,
-		ChatStatusError:
+		ChatStatusError,
+		ChatStatusRequiresAction:
 		return true
 	}
 	return false
@@ -1354,6 +1356,7 @@ func AllChatStatusValues() []ChatStatus {
 		ChatStatusPaused,
 		ChatStatusCompleted,
 		ChatStatusError,
+		ChatStatusRequiresAction,
 	}
 }
 
@@ -1543,6 +1546,64 @@ func AllCorsBehaviorValues() []CorsBehavior {
 	}
 }
 
+type CredentialKind string
+
+const (
+	CredentialKindCentralized CredentialKind = "centralized"
+	CredentialKindByok        CredentialKind = "byok"
+)
+
+func (e *CredentialKind) Scan(src interface{}) error {
+	switch s := src.(type) {
+	case []byte:
+		*e = CredentialKind(s)
+	case string:
+		*e = CredentialKind(s)
+	default:
+		return fmt.Errorf("unsupported scan type for CredentialKind: %T", src)
+	}
+	return nil
+}
+
+type NullCredentialKind struct {
+	CredentialKind CredentialKind `json:"credential_kind"`
+	Valid          bool           `json:"valid"` // Valid is true if CredentialKind is not NULL
+}
+
+// Scan implements the Scanner interface.
+func (ns *NullCredentialKind) Scan(value interface{}) error {
+	if value == nil {
+		ns.CredentialKind, ns.Valid = "", false
+		return nil
+	}
+	ns.Valid = true
+	return ns.CredentialKind.Scan(value)
+}
+
+// Value implements the driver Valuer interface.
+func (ns NullCredentialKind) Value() (driver.Value, error) {
+	if !ns.Valid {
+		return nil, nil
+	}
+	return string(ns.CredentialKind), nil
+}
+
+func (e CredentialKind) Valid() bool {
+	switch e {
+	case CredentialKindCentralized,
+		CredentialKindByok:
+		return true
+	}
+	return false
+}
+
+func AllCredentialKindValues() []CredentialKind {
+	return []CredentialKind{
+		CredentialKindCentralized,
+		CredentialKindByok,
+	}
+}
+
 type CryptoKeyFeature string
 
 const (
@@ -4040,6 +4101,10 @@ type AIBridgeInterception struct {
 	SessionID string `db:"session_id" json:"session_id"`
 	// The provider instance name which may differ from provider when multiple instances of the same provider type exist.
 	ProviderName string `db:"provider_name" json:"provider_name"`
+	// How the request was authenticated: centralized or byok.
+	CredentialKind CredentialKind `db:"credential_kind" json:"credential_kind"`
+	// Masked credential identifier for audit (e.g. sk-a***efgh).
+	CredentialHint string `db:"credential_hint" json:"credential_hint"`
 }
 
 // Audit log of model thinking in intercepted requests in AI Bridge
@@ -4180,6 +4245,45 @@ type Chat struct {
 	PinOrder            int32                 `db:"pin_order" json:"pin_order"`
 	LastReadMessageID   sql.NullInt64         `db:"last_read_message_id" json:"last_read_message_id"`
 	LastInjectedContext pqtype.NullRawMessage `db:"last_injected_context" json:"last_injected_context"`
+	DynamicTools        pqtype.NullRawMessage `db:"dynamic_tools" json:"dynamic_tools"`
+}
+
+type ChatDebugRun struct {
+	ID                  uuid.UUID       `db:"id" json:"id"`
+	ChatID              uuid.UUID       `db:"chat_id" json:"chat_id"`
+	RootChatID          uuid.NullUUID   `db:"root_chat_id" json:"root_chat_id"`
+	ParentChatID        uuid.NullUUID   `db:"parent_chat_id" json:"parent_chat_id"`
+	ModelConfigID       uuid.NullUUID   `db:"model_config_id" json:"model_config_id"`
+	TriggerMessageID    sql.NullInt64   `db:"trigger_message_id" json:"trigger_message_id"`
+	HistoryTipMessageID sql.NullInt64   `db:"history_tip_message_id" json:"history_tip_message_id"`
+	Kind                string          `db:"kind" json:"kind"`
+	Status              string          `db:"status" json:"status"`
+	Provider            sql.NullString  `db:"provider" json:"provider"`
+	Model               sql.NullString  `db:"model" json:"model"`
+	Summary             json.RawMessage `db:"summary" json:"summary"`
+	StartedAt           time.Time       `db:"started_at" json:"started_at"`
+	UpdatedAt           time.Time       `db:"updated_at" json:"updated_at"`
+	FinishedAt          sql.NullTime    `db:"finished_at" json:"finished_at"`
+}
+
+type ChatDebugStep struct {
+	ID                  uuid.UUID             `db:"id" json:"id"`
+	RunID               uuid.UUID             `db:"run_id" json:"run_id"`
+	ChatID              uuid.UUID             `db:"chat_id" json:"chat_id"`
+	StepNumber          int32                 `db:"step_number" json:"step_number"`
+	Operation           string                `db:"operation" json:"operation"`
+	Status              string                `db:"status" json:"status"`
+	HistoryTipMessageID sql.NullInt64         `db:"history_tip_message_id" json:"history_tip_message_id"`
+	AssistantMessageID  sql.NullInt64         `db:"assistant_message_id" json:"assistant_message_id"`
+	NormalizedRequest   json.RawMessage       `db:"normalized_request" json:"normalized_request"`
+	NormalizedResponse  pqtype.NullRawMessage `db:"normalized_response" json:"normalized_response"`
+	Usage               pqtype.NullRawMessage `db:"usage" json:"usage"`
+	Attempts            json.RawMessage       `db:"attempts" json:"attempts"`
+	Error               pqtype.NullRawMessage `db:"error" json:"error"`
+	Metadata            json.RawMessage       `db:"metadata" json:"metadata"`
+	StartedAt           time.Time             `db:"started_at" json:"started_at"`
+	UpdatedAt           time.Time             `db:"updated_at" json:"updated_at"`
+	FinishedAt          sql.NullTime          `db:"finished_at" json:"finished_at"`
 }
 
 type ChatDiffStatus struct {
@@ -4218,6 +4322,11 @@ type ChatFile struct {
 	Data           []byte    `db:"data" json:"data"`
 }
 
+type ChatFileLink struct {
+	ChatID uuid.UUID `db:"chat_id" json:"chat_id"`
+	FileID uuid.UUID `db:"file_id" json:"file_id"`
+}
+
 type ChatMessage struct {
 	ID                  int64                 `db:"id" json:"id"`
 	ChatID              uuid.UUID             `db:"chat_id" json:"chat_id"`

coderd/database/querier.go

@@ -76,6 +76,7 @@ type sqlcQuerier interface {
 	CleanTailnetLostPeers(ctx context.Context) error
 	CleanTailnetTunnels(ctx context.Context) error
 	CleanupDeletedMCPServerIDsFromChats(ctx context.Context) error
+	ClearChatMessageProviderResponseIDsByChatID(ctx context.Context, chatID uuid.UUID) error
 	CountAIBridgeInterceptions(ctx context.Context, arg CountAIBridgeInterceptionsParams) (int64, error)
 	CountAIBridgeSessions(ctx context.Context, arg CountAIBridgeSessionsParams) (int64, error)
 	CountAuditLogs(ctx context.Context, arg CountAuditLogsParams) (int64, error)
@@ -101,6 +102,8 @@ type sqlcQuerier interface {
 	// be recreated.
 	DeleteAllWebpushSubscriptions(ctx context.Context) error
 	DeleteApplicationConnectAPIKeysByUserID(ctx context.Context, userID uuid.UUID) error
+	DeleteChatDebugDataAfterMessageID(ctx context.Context, arg DeleteChatDebugDataAfterMessageIDParams) (int64, error)
+	DeleteChatDebugDataByChatID(ctx context.Context, chatID uuid.UUID) (int64, error)
 	DeleteChatModelConfigByID(ctx context.Context, id uuid.UUID) error
 	DeleteChatProviderByID(ctx context.Context, id uuid.UUID) error
 	DeleteChatQueuedMessage(ctx context.Context, arg DeleteChatQueuedMessageParams) error
@@ -128,6 +131,22 @@ type sqlcQuerier interface {
 	// connection events (connect, disconnect, open, close) which are handled
 	// separately by DeleteOldAuditLogConnectionEvents.
 	DeleteOldAuditLogs(ctx context.Context, arg DeleteOldAuditLogsParams) (int64, error)
+	// TODO(cian): Add indexes on chats(archived, updated_at) and
+	// chat_files(created_at) for purge query performance.
+	// See: https://github.com/coder/internal/issues/1438
+	// Deletes chat files that are older than the given threshold and are
+	// not referenced by any chat that is still active or was archived
+	// within the same threshold window. This covers two cases:
+	// 1. Orphaned files not linked to any chat.
+	// 2. Files whose every referencing chat has been archived for longer
+	//    than the retention period.
+	DeleteOldChatFiles(ctx context.Context, arg DeleteOldChatFilesParams) (int64, error)
+	// Deletes chats that have been archived for longer than the given
+	// threshold. Active (non-archived) chats are never deleted.
+	// Related chat_messages, chat_diff_statuses, and
+	// chat_queued_messages are removed via ON DELETE CASCADE.
+	// Parent/root references on child chats are SET NULL.
+	DeleteOldChats(ctx context.Context, arg DeleteOldChatsParams) (int64, error)
 	DeleteOldConnectionLogs(ctx context.Context, arg DeleteOldConnectionLogsParams) (int64, error)
 	// Delete all notification messages which have not been updated for over a week.
 	DeleteOldNotificationMessages(ctx context.Context) error
@@ -152,7 +171,7 @@ type sqlcQuerier interface {
 	DeleteTask(ctx context.Context, arg DeleteTaskParams) (uuid.UUID, error)
 	DeleteUserChatCompactionThreshold(ctx context.Context, arg DeleteUserChatCompactionThresholdParams) error
 	DeleteUserChatProviderKey(ctx context.Context, arg DeleteUserChatProviderKeyParams) error
-	DeleteUserSecret(ctx context.Context, id uuid.UUID) error
+	DeleteUserSecretByUserIDAndName(ctx context.Context, arg DeleteUserSecretByUserIDAndNameParams) (int64, error)
 	DeleteWebpushSubscriptionByUserIDAndEndpoint(ctx context.Context, arg DeleteWebpushSubscriptionByUserIDAndEndpointParams) error
 	DeleteWebpushSubscriptions(ctx context.Context, ids []uuid.UUID) error
 	DeleteWorkspaceACLByID(ctx context.Context, id uuid.UUID) error
@@ -177,6 +196,16 @@ type sqlcQuerier interface {
 	FetchNewMessageMetadata(ctx context.Context, arg FetchNewMessageMetadataParams) (FetchNewMessageMetadataRow, error)
 	FetchVolumesResourceMonitorsByAgentID(ctx context.Context, agentID uuid.UUID) ([]WorkspaceAgentVolumeResourceMonitor, error)
 	FetchVolumesResourceMonitorsUpdatedAfter(ctx context.Context, updatedAt time.Time) ([]WorkspaceAgentVolumeResourceMonitor, error)
+	// Marks orphaned in-progress rows as interrupted so they do not stay
+	// in a non-terminal state forever.  The NOT IN list must match the
+	// terminal statuses defined by ChatDebugStatus in codersdk/chats.go.
+	//
+	// The steps CTE also catches steps whose parent run was just finalized
+	// (via run_id IN), because PostgreSQL data-modifying CTEs share the
+	// same snapshot and cannot see each other's row updates.  Without this,
+	// a step with a recent updated_at would survive its run's finalization
+	// and remain in 'in_progress' state permanently.
+	FinalizeStaleChatDebugRows(ctx context.Context, updatedBefore time.Time) (FinalizeStaleChatDebugRowsRow, error)
 	// FindMatchingPresetID finds a preset ID that is the largest exact subset of the provided parameters.
 	// It returns the preset ID if a match is found, or NULL if no match is found.
 	// The query finds presets where all preset parameters are present in the provided parameters,
@@ -199,6 +228,7 @@ type sqlcQuerier interface {
 	GetAPIKeysByUserID(ctx context.Context, arg GetAPIKeysByUserIDParams) ([]APIKey, error)
 	GetAPIKeysLastUsedAfter(ctx context.Context, lastUsed time.Time) ([]APIKey, error)
 	GetActiveAISeatCount(ctx context.Context) (int64, error)
+	GetActiveChatsByAgentID(ctx context.Context, agentID uuid.UUID) ([]Chat, error)
 	GetActivePresetPrebuildSchedules(ctx context.Context) ([]TemplateVersionPresetPrebuildSchedule, error)
 	GetActiveUserCount(ctx context.Context, includeSystem bool) (int64, error)
 	GetActiveWorkspaceBuildsByTemplateID(ctx context.Context, templateID uuid.UUID) ([]WorkspaceBuild, error)
@@ -240,10 +270,23 @@ type sqlcQuerier interface {
 	// Aggregate cost summary for a single user within a date range.
 	// Only counts assistant-role messages.
 	GetChatCostSummary(ctx context.Context, arg GetChatCostSummaryParams) (GetChatCostSummaryRow, error)
+	// GetChatDebugLoggingAllowUsers returns the runtime admin setting that
+	// allows users to opt into chat debug logging when the deployment does
+	// not already force debug logging on globally.
+	GetChatDebugLoggingAllowUsers(ctx context.Context) (bool, error)
+	GetChatDebugRunByID(ctx context.Context, id uuid.UUID) (ChatDebugRun, error)
+	// Returns the most recent debug runs for a chat, ordered newest-first.
+	// Callers must supply an explicit limit to avoid unbounded result sets.
+	GetChatDebugRunsByChatID(ctx context.Context, arg GetChatDebugRunsByChatIDParams) ([]ChatDebugRun, error)
+	GetChatDebugStepsByRunID(ctx context.Context, runID uuid.UUID) ([]ChatDebugStep, error)
 	GetChatDesktopEnabled(ctx context.Context) (bool, error)
 	GetChatDiffStatusByChatID(ctx context.Context, chatID uuid.UUID) (ChatDiffStatus, error)
 	GetChatDiffStatusesByChatIDs(ctx context.Context, chatIds []uuid.UUID) ([]ChatDiffStatus, error)
 	GetChatFileByID(ctx context.Context, id uuid.UUID) (ChatFile, error)
+	// GetChatFileMetadataByChatID returns lightweight file metadata for
+	// all files linked to a chat. The data column is excluded to avoid
+	// loading file content.
+	GetChatFileMetadataByChatID(ctx context.Context, chatID uuid.UUID) ([]GetChatFileMetadataByChatIDRow, error)
 	GetChatFilesByIDs(ctx context.Context, ids []uuid.UUID) ([]ChatFile, error)
 	// GetChatIncludeDefaultSystemPrompt preserves the legacy default
 	// for deployments created before the explicit include-default toggle.
@@ -251,16 +294,27 @@ type sqlcQuerier interface {
 	// otherwise the setting defaults to true.
 	GetChatIncludeDefaultSystemPrompt(ctx context.Context) (bool, error)
 	GetChatMessageByID(ctx context.Context, id int64) (ChatMessage, error)
+	// Aggregates message-level metrics per chat for messages created
+	// after the given timestamp. Uses message created_at so that
+	// ongoing activity in long-running chats is captured each window.
+	GetChatMessageSummariesPerChat(ctx context.Context, createdAfter time.Time) ([]GetChatMessageSummariesPerChatRow, error)
 	GetChatMessagesByChatID(ctx context.Context, arg GetChatMessagesByChatIDParams) ([]ChatMessage, error)
 	GetChatMessagesByChatIDAscPaginated(ctx context.Context, arg GetChatMessagesByChatIDAscPaginatedParams) ([]ChatMessage, error)
 	GetChatMessagesByChatIDDescPaginated(ctx context.Context, arg GetChatMessagesByChatIDDescPaginatedParams) ([]ChatMessage, error)
 	GetChatMessagesForPromptByChatID(ctx context.Context, chatID uuid.UUID) ([]ChatMessage, error)
 	GetChatModelConfigByID(ctx context.Context, id uuid.UUID) (ChatModelConfig, error)
 	GetChatModelConfigs(ctx context.Context) ([]ChatModelConfig, error)
+	// Returns all model configurations for telemetry snapshot collection.
+	GetChatModelConfigsForTelemetry(ctx context.Context) ([]GetChatModelConfigsForTelemetryRow, error)
 	GetChatProviderByID(ctx context.Context, id uuid.UUID) (ChatProvider, error)
 	GetChatProviderByProvider(ctx context.Context, provider string) (ChatProvider, error)
 	GetChatProviders(ctx context.Context) ([]ChatProvider, error)
 	GetChatQueuedMessages(ctx context.Context, chatID uuid.UUID) ([]ChatQueuedMessage, error)
+	// Returns the chat retention period in days. Chats archived longer
+	// than this and orphaned chat files older than this are purged by
+	// dbpurge. Returns 30 (days) when no value has been configured.
+	// A value of 0 disables chat purging entirely.
+	GetChatRetentionDays(ctx context.Context) (int32, error)
 	GetChatSystemPrompt(ctx context.Context) (string, error)
 	// GetChatSystemPromptConfig returns both chat system prompt settings in a
 	// single read to avoid torn reads between separate site-config lookups.
@@ -279,6 +333,10 @@ type sqlcQuerier interface {
 	GetChatWorkspaceTTL(ctx context.Context) (string, error)
 	GetChats(ctx context.Context, arg GetChatsParams) ([]GetChatsRow, error)
 	GetChatsByWorkspaceIDs(ctx context.Context, ids []uuid.UUID) ([]Chat, error)
+	// Retrieves chats updated after the given timestamp for telemetry
+	// snapshot collection. Uses updated_at so that long-running chats
+	// still appear in each snapshot window while they are active.
+	GetChatsUpdatedAfter(ctx context.Context, updatedAfter time.Time) ([]GetChatsUpdatedAfterRow, error)
 	GetConnectionLogsOffset(ctx context.Context, arg GetConnectionLogsOffsetParams) ([]GetConnectionLogsOffsetRow, error)
 	GetCryptoKeyByFeatureAndSequence(ctx context.Context, arg GetCryptoKeyByFeatureAndSequenceParams) (CryptoKey, error)
 	GetCryptoKeys(ctx context.Context) ([]CryptoKey, error)
@@ -381,11 +439,12 @@ type sqlcQuerier interface {
 	// per PR for state/additions/deletions/model (model comes from the
 	// most recent chat).
 	GetPRInsightsPerModel(ctx context.Context, arg GetPRInsightsPerModelParams) ([]GetPRInsightsPerModelRow, error)
-	// Returns individual PR rows with cost for the recent PRs table.
+	// Returns all individual PR rows with cost for the selected time range.
 	// Uses two CTEs: pr_costs sums cost for the PR-linked chat and its
 	// direct children (that lack their own PR), and deduped picks one row
-	// per PR for metadata.
-	GetPRInsightsRecentPRs(ctx context.Context, arg GetPRInsightsRecentPRsParams) ([]GetPRInsightsRecentPRsRow, error)
+	// per PR for metadata. A safety-cap LIMIT guards against unexpectedly
+	// large result sets from direct API callers.
+	GetPRInsightsPullRequests(ctx context.Context, arg GetPRInsightsPullRequestsParams) ([]GetPRInsightsPullRequestsRow, error)
 	// PR Insights queries for the /agents analytics dashboard.
 	// These aggregate data from chat_diff_statuses (PR metadata) joined
 	// with chats and chat_messages (cost) to power the PR Insights view.
@@ -474,8 +533,10 @@ type sqlcQuerier interface {
 	GetReplicasUpdatedAfter(ctx context.Context, updatedAt time.Time) ([]Replica, error)
 	GetRunningPrebuiltWorkspaces(ctx context.Context) ([]GetRunningPrebuiltWorkspacesRow, error)
 	GetRuntimeConfig(ctx context.Context, key string) (string, error)
-	// Find chats that appear stuck (running but heartbeat has expired).
-	// Used for recovery after coderd crashes or long hangs.
+	// Find chats that appear stuck and need recovery. This covers:
+	//   1. Running chats whose heartbeat has expired (worker crash).
+	//   2. Chats awaiting client action (requires_action) past the
+	//      timeout threshold (client disappeared).
 	GetStaleChats(ctx context.Context, staleThreshold time.Time) ([]Chat, error)
 	GetTailnetPeers(ctx context.Context, id uuid.UUID) ([]TailnetPeer, error)
 	GetTailnetTunnelPeerBindingsBatch(ctx context.Context, ids []uuid.UUID) ([]GetTailnetTunnelPeerBindingsBatchRow, error)
@@ -579,6 +640,7 @@ type sqlcQuerier interface {
 	GetUserByID(ctx context.Context, id uuid.UUID) (User, error)
 	GetUserChatCompactionThreshold(ctx context.Context, arg GetUserChatCompactionThresholdParams) (string, error)
 	GetUserChatCustomPrompt(ctx context.Context, userID uuid.UUID) (string, error)
+	GetUserChatDebugLoggingEnabled(ctx context.Context, userID uuid.UUID) (bool, error)
 	GetUserChatProviderKeys(ctx context.Context, userID uuid.UUID) ([]UserChatProviderKey, error)
 	GetUserChatSpendInPeriod(ctx context.Context, arg GetUserChatSpendInPeriodParams) (int64, error)
 	GetUserCount(ctx context.Context, includeSystem bool) (int64, error)
@@ -594,7 +656,6 @@ type sqlcQuerier interface {
 	GetUserLinkByUserIDLoginType(ctx context.Context, arg GetUserLinkByUserIDLoginTypeParams) (UserLink, error)
 	GetUserLinksByUserID(ctx context.Context, userID uuid.UUID) ([]UserLink, error)
 	GetUserNotificationPreferences(ctx context.Context, userID uuid.UUID) ([]NotificationPreference, error)
-	GetUserSecret(ctx context.Context, id uuid.UUID) (UserSecret, error)
 	GetUserSecretByUserIDAndName(ctx context.Context, arg GetUserSecretByUserIDAndNameParams) (UserSecret, error)
 	// GetUserStatusCounts returns the count of users in each status over time.
 	// The time range is inclusively defined by the start_time and end_time parameters.
@@ -699,6 +760,8 @@ type sqlcQuerier interface {
 	InsertAllUsersGroup(ctx context.Context, organizationID uuid.UUID) (Group, error)
 	InsertAuditLog(ctx context.Context, arg InsertAuditLogParams) (AuditLog, error)
 	InsertChat(ctx context.Context, arg InsertChatParams) (Chat, error)
+	InsertChatDebugRun(ctx context.Context, arg InsertChatDebugRunParams) (ChatDebugRun, error)
+	InsertChatDebugStep(ctx context.Context, arg InsertChatDebugStepParams) (ChatDebugStep, error)
 	InsertChatFile(ctx context.Context, arg InsertChatFileParams) (InsertChatFileRow, error)
 	InsertChatMessages(ctx context.Context, arg InsertChatMessagesParams) ([]ChatMessage, error)
 	InsertChatModelConfig(ctx context.Context, arg InsertChatModelConfigParams) (ChatModelConfig, error)
@@ -778,6 +841,15 @@ type sqlcQuerier interface {
 	InsertWorkspaceProxy(ctx context.Context, arg InsertWorkspaceProxyParams) (WorkspaceProxy, error)
 	InsertWorkspaceResource(ctx context.Context, arg InsertWorkspaceResourceParams) (WorkspaceResource, error)
 	InsertWorkspaceResourceMetadata(ctx context.Context, arg InsertWorkspaceResourceMetadataParams) ([]WorkspaceResourceMetadatum, error)
+	// LinkChatFiles inserts file associations into the chat_file_links
+	// join table with deduplication (ON CONFLICT DO NOTHING). The INSERT
+	// is conditional: it only proceeds when the total number of links
+	// (existing + genuinely new) does not exceed max_file_links. Returns
+	// the number of genuinely new file IDs that were NOT inserted due to
+	// the cap. A return value of 0 means all files were linked (or were
+	// already linked). A positive value means the cap blocked that many
+	// new links.
+	LinkChatFiles(ctx context.Context, arg LinkChatFilesParams) (int32, error)
 	ListAIBridgeClients(ctx context.Context, arg ListAIBridgeClientsParams) ([]string, error)
 	ListAIBridgeInterceptions(ctx context.Context, arg ListAIBridgeInterceptionsParams) ([]ListAIBridgeInterceptionsRow, error)
 	// Finds all unique AI Bridge interception telemetry summaries combinations
@@ -805,7 +877,13 @@ type sqlcQuerier interface {
 	ListProvisionerKeysByOrganizationExcludeReserved(ctx context.Context, organizationID uuid.UUID) ([]ProvisionerKey, error)
 	ListTasks(ctx context.Context, arg ListTasksParams) ([]Task, error)
 	ListUserChatCompactionThresholds(ctx context.Context, userID uuid.UUID) ([]UserConfig, error)
-	ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]UserSecret, error)
+	// Returns metadata only (no value or value_key_id) for the
+	// REST API list and get endpoints.
+	ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]ListUserSecretsRow, error)
+	// Returns all columns including the secret value. Used by the
+	// provisioner (build-time injection) and the agent manifest
+	// (runtime injection).
+	ListUserSecretsWithValues(ctx context.Context, userID uuid.UUID) ([]UserSecret, error)
 	ListWorkspaceAgentPortShares(ctx context.Context, workspaceID uuid.UUID) ([]WorkspaceAgentPortShare, error)
 	MarkAllInboxNotificationsAsRead(ctx context.Context, arg MarkAllInboxNotificationsAsReadParams) error
 	OIDCClaimFieldValues(ctx context.Context, arg OIDCClaimFieldValuesParams) ([]string, error)
@@ -842,11 +920,16 @@ type sqlcQuerier interface {
 	SelectUsageEventsForPublishing(ctx context.Context, now time.Time) ([]UsageEvent, error)
 	SoftDeleteChatMessageByID(ctx context.Context, id int64) error
 	SoftDeleteChatMessagesAfterID(ctx context.Context, arg SoftDeleteChatMessagesAfterIDParams) error
+	SoftDeleteContextFileMessages(ctx context.Context, chatID uuid.UUID) error
 	// Non blocking lock. Returns true if the lock was acquired, false otherwise.
 	//
 	// This must be called from within a transaction. The lock will be automatically
 	// released when the transaction ends.
 	TryAcquireLock(ctx context.Context, pgTryAdvisoryXactLock int64) (bool, error)
+	// Unarchives a chat (and its children). Stale file references are
+	// handled automatically by FK cascades on chat_file_links: when
+	// dbpurge deletes a chat_files row, the corresponding
+	// chat_file_links rows are cascade-deleted by PostgreSQL.
 	UnarchiveChatByID(ctx context.Context, id uuid.UUID) ([]Chat, error)
 	// This will always work regardless of the current state of the template version.
 	UnarchiveTemplateVersion(ctx context.Context, arg UnarchiveTemplateVersionParams) error
@@ -857,9 +940,21 @@ type sqlcQuerier interface {
 	UpdateAPIKeyByID(ctx context.Context, arg UpdateAPIKeyByIDParams) error
 	UpdateChatBuildAgentBinding(ctx context.Context, arg UpdateChatBuildAgentBindingParams) (Chat, error)
 	UpdateChatByID(ctx context.Context, arg UpdateChatByIDParams) (Chat, error)
-	// Bumps the heartbeat timestamp for a running chat so that other
-	// replicas know the worker is still alive.
-	UpdateChatHeartbeat(ctx context.Context, arg UpdateChatHeartbeatParams) (int64, error)
+	// Uses COALESCE so that passing NULL from Go means "keep the
+	// existing value."  This is intentional: debug rows follow a
+	// write-once-finalize pattern where fields are set at creation
+	// or finalization and never cleared back to NULL.
+	UpdateChatDebugRun(ctx context.Context, arg UpdateChatDebugRunParams) (ChatDebugRun, error)
+	// Uses COALESCE so that passing NULL from Go means "keep the
+	// existing value."  This is intentional: debug rows follow a
+	// write-once-finalize pattern where fields are set at creation
+	// or finalization and never cleared back to NULL.
+	UpdateChatDebugStep(ctx context.Context, arg UpdateChatDebugStepParams) (ChatDebugStep, error)
+	// Bumps the heartbeat timestamp for the given set of chat IDs,
+	// provided they are still running and owned by the specified
+	// worker. Returns the IDs that were actually updated so the
+	// caller can detect stolen or completed chats via set-difference.
+	UpdateChatHeartbeats(ctx context.Context, arg UpdateChatHeartbeatsParams) ([]uuid.UUID, error)
 	UpdateChatLabelsByID(ctx context.Context, arg UpdateChatLabelsByIDParams) (Chat, error)
 	// Updates the cached injected context parts (AGENTS.md +
 	// skills) on the chat row. Called only when context changes
@@ -942,7 +1037,7 @@ type sqlcQuerier interface {
 	UpdateUserProfile(ctx context.Context, arg UpdateUserProfileParams) (User, error)
 	UpdateUserQuietHoursSchedule(ctx context.Context, arg UpdateUserQuietHoursScheduleParams) (User, error)
 	UpdateUserRoles(ctx context.Context, arg UpdateUserRolesParams) (User, error)
-	UpdateUserSecret(ctx context.Context, arg UpdateUserSecretParams) (UserSecret, error)
+	UpdateUserSecretByUserIDAndName(ctx context.Context, arg UpdateUserSecretByUserIDAndNameParams) (UserSecret, error)
 	UpdateUserStatus(ctx context.Context, arg UpdateUserStatusParams) (User, error)
 	UpdateUserTaskNotificationAlertDismissed(ctx context.Context, arg UpdateUserTaskNotificationAlertDismissedParams) (bool, error)
 	UpdateUserTerminalFont(ctx context.Context, arg UpdateUserTerminalFontParams) (UserConfig, error)
@@ -951,6 +1046,7 @@ type sqlcQuerier interface {
 	UpdateWorkspace(ctx context.Context, arg UpdateWorkspaceParams) (WorkspaceTable, error)
 	UpdateWorkspaceACLByID(ctx context.Context, arg UpdateWorkspaceACLByIDParams) error
 	UpdateWorkspaceAgentConnectionByID(ctx context.Context, arg UpdateWorkspaceAgentConnectionByIDParams) error
+	UpdateWorkspaceAgentDirectoryByID(ctx context.Context, arg UpdateWorkspaceAgentDirectoryByIDParams) error
 	UpdateWorkspaceAgentDisplayAppsByID(ctx context.Context, arg UpdateWorkspaceAgentDisplayAppsByIDParams) error
 	UpdateWorkspaceAgentLifecycleStateByID(ctx context.Context, arg UpdateWorkspaceAgentLifecycleStateByIDParams) error
 	UpdateWorkspaceAgentLogOverflowByID(ctx context.Context, arg UpdateWorkspaceAgentLogOverflowByIDParams) error
@@ -982,10 +1078,14 @@ type sqlcQuerier interface {
 	// cumulative values for unique counts (accurate period totals). Request counts
 	// are always deltas, accumulated in DB. Returns true if insert, false if update.
 	UpsertBoundaryUsageStats(ctx context.Context, arg UpsertBoundaryUsageStatsParams) (bool, error)
+	// UpsertChatDebugLoggingAllowUsers updates the runtime admin setting that
+	// allows users to opt into chat debug logging.
+	UpsertChatDebugLoggingAllowUsers(ctx context.Context, allowUsers bool) error
 	UpsertChatDesktopEnabled(ctx context.Context, enableDesktop bool) error
 	UpsertChatDiffStatus(ctx context.Context, arg UpsertChatDiffStatusParams) (ChatDiffStatus, error)
 	UpsertChatDiffStatusReference(ctx context.Context, arg UpsertChatDiffStatusReferenceParams) (ChatDiffStatus, error)
 	UpsertChatIncludeDefaultSystemPrompt(ctx context.Context, includeDefaultSystemPrompt bool) error
+	UpsertChatRetentionDays(ctx context.Context, retentionDays int32) error
 	UpsertChatSystemPrompt(ctx context.Context, value string) error
 	UpsertChatTemplateAllowlist(ctx context.Context, templateAllowlist string) error
 	UpsertChatUsageLimitConfig(ctx context.Context, arg UpsertChatUsageLimitConfigParams) (ChatUsageLimitConfig, error)
@@ -1018,6 +1118,7 @@ type sqlcQuerier interface {
 	// used to store the data, and the minutes are summed for each user and template
 	// combination. The result is stored in the template_usage_stats table.
 	UpsertTemplateUsageStats(ctx context.Context) error
+	UpsertUserChatDebugLoggingEnabled(ctx context.Context, arg UpsertUserChatDebugLoggingEnabledParams) error
 	UpsertUserChatProviderKey(ctx context.Context, arg UpsertUserChatProviderKeyParams) (UserChatProviderKey, error)
 	UpsertWebpushVAPIDKeys(ctx context.Context, arg UpsertWebpushVAPIDKeysParams) error
 	UpsertWorkspaceAgentPortShare(ctx context.Context, arg UpsertWorkspaceAgentPortShareParams) (WorkspaceAgentPortShare, error)

coderd/database/queries/aibridge.sql

@@ -1,8 +1,8 @@
 -- name: InsertAIBridgeInterception :one
 INSERT INTO aibridge_interceptions (
-	id, api_key_id, initiator_id, provider, provider_name, model, metadata, started_at, client, client_session_id, thread_parent_id, thread_root_id
+	id, api_key_id, initiator_id, provider, provider_name, model, metadata, started_at, client, client_session_id, thread_parent_id, thread_root_id, credential_kind, credential_hint
 ) VALUES (
-	@id, @api_key_id, @initiator_id, @provider, @provider_name, @model, COALESCE(@metadata::jsonb, '{}'::jsonb), @started_at, @client, sqlc.narg('client_session_id'), sqlc.narg('thread_parent_interception_id')::uuid, sqlc.narg('thread_root_interception_id')::uuid
+	@id, @api_key_id, @initiator_id, @provider, @provider_name, @model, COALESCE(@metadata::jsonb, '{}'::jsonb), @started_at, @client, sqlc.narg('client_session_id'), sqlc.narg('thread_parent_interception_id')::uuid, sqlc.narg('thread_root_interception_id')::uuid, @credential_kind, @credential_hint
 )
 RETURNING *;
 

coderd/database/queries/auditlogs.sql

@@ -149,94 +149,105 @@ VALUES (
 RETURNING *;
 
 -- name: CountAuditLogs :one
-SELECT COUNT(*)
-FROM audit_logs
-	LEFT JOIN users ON audit_logs.user_id = users.id
-	LEFT JOIN organizations ON audit_logs.organization_id = organizations.id
-	-- First join on workspaces to get the initial workspace create
-	-- to workspace build 1 id. This is because the first create is
-	-- is a different audit log than subsequent starts.
-	LEFT JOIN workspaces ON audit_logs.resource_type = 'workspace'
-	AND audit_logs.resource_id = workspaces.id
-	-- Get the reason from the build if the resource type
-	-- is a workspace_build
-	LEFT JOIN workspace_builds wb_build ON audit_logs.resource_type = 'workspace_build'
-	AND audit_logs.resource_id = wb_build.id
-	-- Get the reason from the build #1 if this is the first
-	-- workspace create.
-	LEFT JOIN workspace_builds wb_workspace ON audit_logs.resource_type = 'workspace'
-	AND audit_logs.action = 'create'
-	AND workspaces.id = wb_workspace.workspace_id
-	AND wb_workspace.build_number = 1
-WHERE
-	-- Filter resource_type
-	CASE
-		WHEN @resource_type::text != '' THEN resource_type = @resource_type::resource_type
-		ELSE true
-	END
-	-- Filter resource_id
-	AND CASE
-		WHEN @resource_id::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN resource_id = @resource_id
-		ELSE true
-	END
-	-- Filter organization_id
-	AND CASE
-		WHEN @organization_id::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN audit_logs.organization_id = @organization_id
-		ELSE true
-	END
-	-- Filter by resource_target
-	AND CASE
-		WHEN @resource_target::text != '' THEN resource_target = @resource_target
-		ELSE true
-	END
-	-- Filter action
-	AND CASE
-		WHEN @action::text != '' THEN action = @action::audit_action
-		ELSE true
-	END
-	-- Filter by user_id
-	AND CASE
-		WHEN @user_id::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN user_id = @user_id
-		ELSE true
-	END
-	-- Filter by username
-	AND CASE
-		WHEN @username::text != '' THEN user_id = (
-			SELECT id
-			FROM users
-			WHERE lower(username) = lower(@username)
-				AND deleted = false
-		)
-		ELSE true
-	END
-	-- Filter by user_email
-	AND CASE
-		WHEN @email::text != '' THEN users.email = @email
-		ELSE true
-	END
-	-- Filter by date_from
-	AND CASE
-		WHEN @date_from::timestamp with time zone != '0001-01-01 00:00:00Z' THEN "time" >= @date_from
-		ELSE true
-	END
-	-- Filter by date_to
-	AND CASE
-		WHEN @date_to::timestamp with time zone != '0001-01-01 00:00:00Z' THEN "time" <= @date_to
-		ELSE true
-	END
-	-- Filter by build_reason
-	AND CASE
-		WHEN @build_reason::text != '' THEN COALESCE(wb_build.reason::text, wb_workspace.reason::text) = @build_reason
-		ELSE true
-	END
-	-- Filter request_id
-	AND CASE
-		WHEN @request_id::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN audit_logs.request_id = @request_id
-		ELSE true
-	END
-	-- Authorize Filter clause will be injected below in CountAuthorizedAuditLogs
-	-- @authorize_filter
-;
+SELECT COUNT(*) FROM (
+	SELECT 1
+	FROM audit_logs
+		LEFT JOIN users ON audit_logs.user_id = users.id
+		LEFT JOIN organizations ON audit_logs.organization_id = organizations.id
+		-- First join on workspaces to get the initial workspace create
+		-- to workspace build 1 id. This is because the first create is
+		-- is a different audit log than subsequent starts.
+		LEFT JOIN workspaces ON audit_logs.resource_type = 'workspace'
+		AND audit_logs.resource_id = workspaces.id
+		-- Get the reason from the build if the resource type
+		-- is a workspace_build
+		LEFT JOIN workspace_builds wb_build ON audit_logs.resource_type = 'workspace_build'
+		AND audit_logs.resource_id = wb_build.id
+		-- Get the reason from the build #1 if this is the first
+		-- workspace create.
+		LEFT JOIN workspace_builds wb_workspace ON audit_logs.resource_type = 'workspace'
+		AND audit_logs.action = 'create'
+		AND workspaces.id = wb_workspace.workspace_id
+		AND wb_workspace.build_number = 1
+	WHERE
+		-- Filter resource_type
+		CASE
+			WHEN @resource_type::text != '' THEN resource_type = @resource_type::resource_type
+			ELSE true
+		END
+		-- Filter resource_id
+		AND CASE
+			WHEN @resource_id::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN resource_id = @resource_id
+			ELSE true
+		END
+		-- Filter organization_id
+		AND CASE
+			WHEN @organization_id::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN audit_logs.organization_id = @organization_id
+			ELSE true
+		END
+		-- Filter by resource_target
+		AND CASE
+			WHEN @resource_target::text != '' THEN resource_target = @resource_target
+			ELSE true
+		END
+		-- Filter action
+		AND CASE
+			WHEN @action::text != '' THEN action = @action::audit_action
+			ELSE true
+		END
+		-- Filter by user_id
+		AND CASE
+			WHEN @user_id::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN user_id = @user_id
+			ELSE true
+		END
+		-- Filter by username
+		AND CASE
+			WHEN @username::text != '' THEN user_id = (
+				SELECT id
+				FROM users
+				WHERE lower(username) = lower(@username)
+					AND deleted = false
+			)
+			ELSE true
+		END
+		-- Filter by user_email
+		AND CASE
+			WHEN @email::text != '' THEN users.email = @email
+			ELSE true
+		END
+		-- Filter by date_from
+		AND CASE
+			WHEN @date_from::timestamp with time zone != '0001-01-01 00:00:00Z' THEN "time" >= @date_from
+			ELSE true
+		END
+		-- Filter by date_to
+		AND CASE
+			WHEN @date_to::timestamp with time zone != '0001-01-01 00:00:00Z' THEN "time" <= @date_to
+			ELSE true
+		END
+		-- Filter by build_reason
+		AND CASE
+			WHEN @build_reason::text != '' THEN COALESCE(wb_build.reason::text, wb_workspace.reason::text) = @build_reason
+			ELSE true
+		END
+		-- Filter request_id
+		AND CASE
+			WHEN @request_id::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN audit_logs.request_id = @request_id
+			ELSE true
+		END
+		-- Authorize Filter clause will be injected below in CountAuthorizedAuditLogs
+		-- @authorize_filter
+	-- Avoid a slow scan on a large table with joins. The caller
+	-- passes the count cap and we add 1 so the frontend can detect
+	-- capping and show "... of N+". A cap of 0 means no limit (NULLIF
+	-- -> NULL + 1 = NULL).
+	-- NOTE: Parameterizing this so that we can easily change from,
+	-- e.g., 2000 to 5000. However, use literal NULL (or no LIMIT)
+	-- here if disabling the capping on a large table permanently.
+	-- This way the PG planner can plan parallel execution for
+	-- potential large wins.
+	LIMIT NULLIF(@count_cap::int, 0) + 1
+) AS limited_count;
 
 -- name: DeleteOldAuditLogConnectionEvents :exec
 DELETE FROM audit_logs

coderd/database/queries/chatdebug.sql

@@ -0,0 +1,205 @@
+-- name: InsertChatDebugRun :one
+INSERT INTO chat_debug_runs (
+    chat_id,
+    root_chat_id,
+    parent_chat_id,
+    model_config_id,
+    trigger_message_id,
+    history_tip_message_id,
+    kind,
+    status,
+    provider,
+    model,
+    summary,
+    started_at,
+    updated_at,
+    finished_at
+)
+VALUES (
+    @chat_id::uuid,
+    sqlc.narg('root_chat_id')::uuid,
+    sqlc.narg('parent_chat_id')::uuid,
+    sqlc.narg('model_config_id')::uuid,
+    sqlc.narg('trigger_message_id')::bigint,
+    sqlc.narg('history_tip_message_id')::bigint,
+    @kind::text,
+    @status::text,
+    sqlc.narg('provider')::text,
+    sqlc.narg('model')::text,
+    COALESCE(sqlc.narg('summary')::jsonb, '{}'::jsonb),
+    COALESCE(sqlc.narg('started_at')::timestamptz, NOW()),
+    COALESCE(sqlc.narg('updated_at')::timestamptz, NOW()),
+    sqlc.narg('finished_at')::timestamptz
+)
+RETURNING *;
+
+-- name: UpdateChatDebugRun :one
+-- Uses COALESCE so that passing NULL from Go means "keep the
+-- existing value."  This is intentional: debug rows follow a
+-- write-once-finalize pattern where fields are set at creation
+-- or finalization and never cleared back to NULL.
+UPDATE chat_debug_runs
+SET
+    root_chat_id = COALESCE(sqlc.narg('root_chat_id')::uuid, root_chat_id),
+    parent_chat_id = COALESCE(sqlc.narg('parent_chat_id')::uuid, parent_chat_id),
+    model_config_id = COALESCE(sqlc.narg('model_config_id')::uuid, model_config_id),
+    trigger_message_id = COALESCE(sqlc.narg('trigger_message_id')::bigint, trigger_message_id),
+    history_tip_message_id = COALESCE(sqlc.narg('history_tip_message_id')::bigint, history_tip_message_id),
+    status = COALESCE(sqlc.narg('status')::text, status),
+    provider = COALESCE(sqlc.narg('provider')::text, provider),
+    model = COALESCE(sqlc.narg('model')::text, model),
+    summary = COALESCE(sqlc.narg('summary')::jsonb, summary),
+    finished_at = COALESCE(sqlc.narg('finished_at')::timestamptz, finished_at),
+    updated_at = NOW()
+WHERE id = @id::uuid
+    AND chat_id = @chat_id::uuid
+RETURNING *;
+
+-- name: InsertChatDebugStep :one
+INSERT INTO chat_debug_steps (
+    run_id,
+    chat_id,
+    step_number,
+    operation,
+    status,
+    history_tip_message_id,
+    assistant_message_id,
+    normalized_request,
+    normalized_response,
+    usage,
+    attempts,
+    error,
+    metadata,
+    started_at,
+    updated_at,
+    finished_at
+)
+SELECT
+    @run_id::uuid,
+    run.chat_id,
+    @step_number::int,
+    @operation::text,
+    @status::text,
+    sqlc.narg('history_tip_message_id')::bigint,
+    sqlc.narg('assistant_message_id')::bigint,
+    COALESCE(sqlc.narg('normalized_request')::jsonb, '{}'::jsonb),
+    sqlc.narg('normalized_response')::jsonb,
+    sqlc.narg('usage')::jsonb,
+    COALESCE(sqlc.narg('attempts')::jsonb, '[]'::jsonb),
+    sqlc.narg('error')::jsonb,
+    COALESCE(sqlc.narg('metadata')::jsonb, '{}'::jsonb),
+    COALESCE(sqlc.narg('started_at')::timestamptz, NOW()),
+    COALESCE(sqlc.narg('updated_at')::timestamptz, NOW()),
+    sqlc.narg('finished_at')::timestamptz
+FROM chat_debug_runs run
+WHERE run.id = @run_id::uuid
+    AND run.chat_id = @chat_id::uuid
+RETURNING *;
+
+-- name: UpdateChatDebugStep :one
+-- Uses COALESCE so that passing NULL from Go means "keep the
+-- existing value."  This is intentional: debug rows follow a
+-- write-once-finalize pattern where fields are set at creation
+-- or finalization and never cleared back to NULL.
+UPDATE chat_debug_steps
+SET
+    status = COALESCE(sqlc.narg('status')::text, status),
+    history_tip_message_id = COALESCE(sqlc.narg('history_tip_message_id')::bigint, history_tip_message_id),
+    assistant_message_id = COALESCE(sqlc.narg('assistant_message_id')::bigint, assistant_message_id),
+    normalized_request = COALESCE(sqlc.narg('normalized_request')::jsonb, normalized_request),
+    normalized_response = COALESCE(sqlc.narg('normalized_response')::jsonb, normalized_response),
+    usage = COALESCE(sqlc.narg('usage')::jsonb, usage),
+    attempts = COALESCE(sqlc.narg('attempts')::jsonb, attempts),
+    error = COALESCE(sqlc.narg('error')::jsonb, error),
+    metadata = COALESCE(sqlc.narg('metadata')::jsonb, metadata),
+    finished_at = COALESCE(sqlc.narg('finished_at')::timestamptz, finished_at),
+    updated_at = NOW()
+WHERE id = @id::uuid
+    AND chat_id = @chat_id::uuid
+RETURNING *;
+
+-- name: GetChatDebugRunsByChatID :many
+-- Returns the most recent debug runs for a chat, ordered newest-first.
+-- Callers must supply an explicit limit to avoid unbounded result sets.
+SELECT *
+FROM chat_debug_runs
+WHERE chat_id = @chat_id::uuid
+ORDER BY started_at DESC, id DESC
+LIMIT @limit_val::int;
+
+-- name: GetChatDebugRunByID :one
+SELECT *
+FROM chat_debug_runs
+WHERE id = @id::uuid;
+
+-- name: GetChatDebugStepsByRunID :many
+SELECT *
+FROM chat_debug_steps
+WHERE run_id = @run_id::uuid
+ORDER BY step_number ASC, started_at ASC;
+
+-- name: DeleteChatDebugDataByChatID :execrows
+DELETE FROM chat_debug_runs
+WHERE chat_id = @chat_id::uuid;
+
+-- name: DeleteChatDebugDataAfterMessageID :execrows
+WITH affected_runs AS (
+    SELECT DISTINCT run.id
+    FROM chat_debug_runs run
+    WHERE run.chat_id = @chat_id::uuid
+        AND (
+            run.history_tip_message_id > @message_id::bigint
+            OR run.trigger_message_id > @message_id::bigint
+        )
+
+    UNION
+
+    SELECT DISTINCT step.run_id AS id
+    FROM chat_debug_steps step
+    WHERE step.chat_id = @chat_id::uuid
+        AND (
+            step.assistant_message_id > @message_id::bigint
+            OR step.history_tip_message_id > @message_id::bigint
+        )
+)
+DELETE FROM chat_debug_runs
+WHERE chat_id = @chat_id::uuid
+    AND id IN (SELECT id FROM affected_runs);
+
+-- name: FinalizeStaleChatDebugRows :one
+-- Marks orphaned in-progress rows as interrupted so they do not stay
+-- in a non-terminal state forever.  The NOT IN list must match the
+-- terminal statuses defined by ChatDebugStatus in codersdk/chats.go.
+--
+-- The steps CTE also catches steps whose parent run was just finalized
+-- (via run_id IN), because PostgreSQL data-modifying CTEs share the
+-- same snapshot and cannot see each other's row updates.  Without this,
+-- a step with a recent updated_at would survive its run's finalization
+-- and remain in 'in_progress' state permanently.
+WITH finalized_runs AS (
+    UPDATE chat_debug_runs
+    SET
+        status = 'interrupted',
+        updated_at = NOW(),
+        finished_at = NOW()
+    WHERE updated_at < @updated_before::timestamptz
+        AND finished_at IS NULL
+        AND status NOT IN ('completed', 'error', 'interrupted')
+    RETURNING id
+), finalized_steps AS (
+    UPDATE chat_debug_steps
+    SET
+        status = 'interrupted',
+        updated_at = NOW(),
+        finished_at = NOW()
+    WHERE (
+            updated_at < @updated_before::timestamptz
+            OR run_id IN (SELECT id FROM finalized_runs)
+        )
+        AND finished_at IS NULL
+        AND status NOT IN ('completed', 'error', 'interrupted')
+    RETURNING 1
+)
+SELECT
+    (SELECT COUNT(*) FROM finalized_runs)::bigint AS runs_finalized,
+    (SELECT COUNT(*) FROM finalized_steps)::bigint AS steps_finalized;

coderd/database/queries/chatfiles.sql

@@ -8,3 +8,47 @@ SELECT * FROM chat_files WHERE id = @id::uuid;
 
 -- name: GetChatFilesByIDs :many
 SELECT * FROM chat_files WHERE id = ANY(@ids::uuid[]);
+
+-- name: GetChatFileMetadataByChatID :many
+-- GetChatFileMetadataByChatID returns lightweight file metadata for
+-- all files linked to a chat. The data column is excluded to avoid
+-- loading file content.
+SELECT cf.id, cf.owner_id, cf.organization_id, cf.name, cf.mimetype, cf.created_at
+FROM chat_files cf
+JOIN chat_file_links cfl ON cfl.file_id = cf.id
+WHERE cfl.chat_id = @chat_id::uuid
+ORDER BY cf.created_at ASC;
+
+-- TODO(cian): Add indexes on chats(archived, updated_at) and
+-- chat_files(created_at) for purge query performance.
+-- See: https://github.com/coder/internal/issues/1438
+-- name: DeleteOldChatFiles :execrows
+-- Deletes chat files that are older than the given threshold and are
+-- not referenced by any chat that is still active or was archived
+-- within the same threshold window. This covers two cases:
+-- 1. Orphaned files not linked to any chat.
+-- 2. Files whose every referencing chat has been archived for longer
+--    than the retention period.
+WITH kept_file_ids AS (
+    -- NOTE: This uses updated_at as a proxy for archive time
+    -- because there is no archived_at column. Correctness
+    -- requires that updated_at is never backdated on archived
+    -- chats. See ArchiveChatByID.
+    SELECT DISTINCT cfl.file_id
+    FROM chat_file_links cfl
+    JOIN chats c ON c.id = cfl.chat_id
+    WHERE c.archived = false
+       OR c.updated_at >= @before_time::timestamptz
+),
+deletable AS (
+    SELECT cf.id
+    FROM chat_files cf
+    LEFT JOIN kept_file_ids k ON cf.id = k.file_id
+    WHERE cf.created_at < @before_time::timestamptz
+      AND k.file_id IS NULL
+    ORDER BY cf.created_at ASC
+    LIMIT @limit_count
+)
+DELETE FROM chat_files
+USING deletable
+WHERE chat_files.id = deletable.id;