fix(site/src/pages/AgentsPage): stabilize chat scroll on git watcher updates

The chat scroll position jumped every time the git watcher WebSocket received data because urlTransform was recreated on every AgentDetail render due to React Compiler hook interleaving, and isConnected state caused unnecessary re-renders on every WebSocket lifecycle event. Three changes fix this: 1. Extract buildUrlTransform as a module-level function and pass primitive fields (proxyHost, agentName, wsName, wsOwner) via urlTransformProps instead of a pre-built function. The compiler guards the props object on primitives (stable) and guards the buildUrlTransform call inside AgentDetailView (slot 5). The AgentDetailTimeline guard (slot 59) now hits when git data changes, keeping the scroll container content cached. 2. Convert isConnected from useState to useRef in useGitWatcher. No component renders this value; it was causing two wasted full-tree re-renders per WebSocket open/close cycle. 3. Split the gitWatcher prop into gitRepositories and gitRefresh, and use repositoriesRef for imperative access in handleOpenInEditor. This removes the opaque gitWatcher object from the AgentDetailView JSX guard, preventing unnecessary element re-creation when only git data changes.
feat(site/src/pages/AgentsPage): add ArrowUp shortcut to edit last user message (#23705 )
2026-03-27 12:45:54 +00:00 · 2026-03-27 21:43:31 +11:00 · 2026-03-27 18:47:39 +11:00 · 2026-03-27 17:55:19 +11:00 · 2026-03-27 05:51:51 +00:00 · 2026-03-27 01:47:19 +01:00
2133 changed files with 200120 additions and 51715 deletions
@@ -0,0 +1,343 @@
+---
+name: deep-review
+description: "Multi-reviewer code review. Spawns domain-specific reviewers in parallel, cross-checks findings, posts a single structured GitHub review."
+---
+
+# Deep Review
+
+Multi-reviewer code review. Spawns domain-specific reviewers in parallel, cross-checks their findings for contradictions and convergence, then posts a single structured GitHub review with inline comments.
+
+## When to use this skill
+
+- PRs touching 3+ subsystems, >500 lines, or requiring domain-specific expertise (security, concurrency, database).
+- When you want independent perspectives cross-checked against each other, not just a single-pass review.
+
+Use `.claude/skills/code-review/` for focused single-domain changes or quick single-pass reviews.
+
+**Prerequisite:** This skill requires the ability to spawn parallel subagents. If your agent runtime cannot spawn subagents, use code-review instead.
+
+**Severity scales:** Deep-review uses P0–P4 (consequence-based). Code-review uses 🔴🟡🔵. Both are valid; they serve different review depths. Approximate mapping: P0–P1 ≈ 🔴, P2 ≈ 🟡, P3–P4 ≈ 🔵.
+
+## When NOT to use this skill
+
+- Docs-only or config-only PRs (no code to structurally review). Use `.claude/skills/doc-check/` instead.
+- Single-file changes under ~50 lines.
+- The PR author asked for a quick review.
+
+## 0. Proportionality check
+
+Estimate scope before committing to a deep review. If the PR has fewer than 3 files and fewer than 100 lines changed, suggest code-review instead. If the PR is docs-only, suggest doc-check. Proceed only if the change warrants multi-reviewer analysis.
+
+## 1. Scope the change
+
+**Author independence.** Review with the same rigor regardless of who authored the PR. Don't soften findings because the author is the person who invoked this review, a maintainer, or a senior contributor. Don't harden findings because the author is a new contributor. The review's value comes from honest, consistent assessment.
+
+Create the review output directory before anything else:
+
+```sh
+export REVIEW_DIR="/tmp/deep-review/$(date +%s)"
+mkdir -p "$REVIEW_DIR"
+```
+
+**Re-review detection.** Check if you or a previous agent session already reviewed this PR:
+
+```sh
+gh pr view {number} --json reviews --jq '.reviews[] | select(.body | test("P[0-4]|\\*\\*Obs\\*\\*|\\*\\*Nit\\*\\*")) | .submittedAt' | head -1
+```
+
+If a prior agent review exists, you must produce a prior-findings classification table before proceeding. This is not optional — the table is an input to step 3 (reviewer prompts). Without it, reviewers will re-discover resolved findings.
+
+1. Read every author response since the last review (inline replies, PR comments, commit messages).
+2. Diff the branch to see what changed since the last review.
+3. Engage with any author questions before re-raising findings.
+4. Write `$REVIEW_DIR/prior-findings.md` with this format:
+
+```markdown
+# Prior findings from round {N}
+
+| Finding | Author response | Status |
+|---------|----------------|--------|
+| P1 `file.go:42` wire-format break | Acknowledged, pushed fix in abc123 | Resolved |
+| P2 `handler.go:15` missing auth check | "Middleware handles this" — see comment | Contested |
+| P3 `db.go:88` naming | Agreed, will fix | Acknowledged |
+```
+
+Classify each finding as:
+
+- **Resolved**: author pushed a code fix. Verify the fix addresses the finding's specific concern — not just that code changed in the relevant area. Check that the fix doesn't introduce new issues.
+- **Acknowledged**: author agreed but deferred.
+- **Contested**: author disagreed or raised a constraint. Write their argument in the table.
+- **No response**: author didn't address it.
+
+Only **Contested** and **No response** findings carry forward to the new review. Resolved and Acknowledged findings must not be re-raised.
+
+**Scope the diff.** Get the file list from the diff, PR, or user. Skim for intent and note which layers are touched (frontend, backend, database, auth, concurrency, tests, docs).
+
+For each changed file, briefly check the surrounding context:
+
+- Config files (package.json, tsconfig, vite.config, etc.): scan the existing entries for naming conventions and structural patterns.
+- New files: check if an existing file could have been extended instead.
+- Comments in the diff: do they explain why, or just restate what the code does?
+
+## 2. Pick reviewers
+
+Match reviewer roles to layers touched. The Test Auditor, Edge Case Analyst, and Contract Auditor always run. Conditional reviewers activate when their domain is touched.
+
+### Tier 1 — Structural reviewers
+
+| Role                 | Focus                                                       | When                                                        |
+| -------------------- | ----------------------------------------------------------- | ----------------------------------------------------------- |
+| Test Auditor         | Test authenticity, missing cases, readability               | Always                                                      |
+| Edge Case Analyst    | Chaos testing, edge cases, hidden connections               | Always                                                      |
+| Contract Auditor     | Contract fidelity, lifecycle completeness, semantic honesty | Always                                                      |
+| Structural Analyst   | Implicit assumptions, class-of-bug elimination              | API design, type design, test structure, resource lifecycle |
+| Performance Analyst  | Hot paths, resource exhaustion, allocation patterns         | Hot paths, loops, caches, resource lifecycle                |
+| Database Reviewer    | PostgreSQL, data modeling, Go↔SQL boundary                  | Migrations, queries, schema, indexes                        |
+| Security Reviewer    | Auth, attack surfaces, input handling                       | Auth, new endpoints, input handling, tokens, secrets        |
+| Product Reviewer     | Over-engineering, feature justification                     | New features, new config surfaces                           |
+| Frontend Reviewer    | UI state, render lifecycles, component design               | Frontend changes, UI components, API response shape changes |
+| Duplication Checker  | Existing utilities, code reuse                              | New files, new helpers/utilities, new types or components   |
+| Go Architect         | Package boundaries, API lifecycle, middleware               | Go code, API design, middleware, package boundaries         |
+| Concurrency Reviewer | Goroutines, channels, locks, shutdown                       | Goroutines, channels, locks, context cancellation, shutdown |
+
+### Tier 2 — Nit reviewers
+
+| Role                   | Focus                                        | File filter                         |
+| ---------------------- | -------------------------------------------- | ----------------------------------- |
+| Modernization Reviewer | Language-level improvements, stdlib patterns | Per-language (see below)            |
+| Style Reviewer         | Naming, comments, consistency                | `*.go` `*.ts` `*.tsx` `*.py` `*.sh` |
+
+Tier 2 file filters:
+
+- **Modernization Reviewer**: one instance per language present in the diff. Filter by extension:
+  - Go: `*.go` — reference `.claude/docs/GO.md` before reviewing.
+  - TypeScript: `*.ts` `*.tsx`
+  - React: `*.tsx` `*.jsx`
+
+  `.tsx` files match both TypeScript and React filters. Spawn both instances when the diff contains `.tsx` changes — TS covers language-level patterns; React covers component and hooks patterns. Before spawning, verify each instance's filter produces a non-empty diff. Skip instances whose filtered diff is empty.
+
+- **Style Reviewer**: `*.go` `*.ts` `*.tsx` `*.py` `*.sh`
+
+## 3. Spawn reviewers
+
+Each reviewer writes findings to `$REVIEW_DIR/{role-name}.md` where `{role-name}` is the kebab-cased role name (e.g. `test-auditor`, `go-architect`). For Modernization Reviewer instances, qualify with the language: `modernization-reviewer-go.md`, `modernization-reviewer-ts.md`, `modernization-reviewer-react.md`. The orchestrator does not read reviewer findings from the subagent return text — it reads the files in step 4.
+
+Spawn all Tier 1 and Tier 2 reviewers in parallel. Give each reviewer a reference (PR number, branch name), not the diff content. The reviewer fetches the diff itself. Reviewers are read-only — no worktrees needed.
+
+**Tier 1 prompt:**
+
+```text
+Read `AGENTS.md` in this repository before starting.
+
+You are the {Role Name} reviewer. Read your methodology in
+`.agents/skills/deep-review/roles/{role-name}.md`.
+
+Follow the review instructions in
+`.agents/skills/deep-review/structural-reviewer-prompt.md`.
+
+Review: {PR number / branch / commit range}.
+Output file: {REVIEW_DIR}/{role-name}.md
+```
+
+**Tier 2 prompt:**
+
+```text
+Read `AGENTS.md` in this repository before starting.
+
+You are the {Role Name} reviewer. Read your methodology in
+`.agents/skills/deep-review/roles/{role-name}.md`.
+
+Follow the review instructions in
+`.agents/skills/deep-review/nit-reviewer-prompt.md`.
+
+Review: {PR number / branch / commit range}.
+File scope: {filter from step 2}.
+Output file: {REVIEW_DIR}/{role-name}.md
+```
+
+For the Modernization Reviewer (Go), add after the methodology line:
+
+> Read `.claude/docs/GO.md` as your Go language reference before reviewing.
+
+For re-reviews, append to both Tier 1 and Tier 2 prompts:
+
+> Prior findings and author responses are in {REVIEW_DIR}/prior-findings.md. Read it before reviewing. Do not re-raise Resolved or Acknowledged findings.
+
+## 4. Cross-check findings
+
+### 4a. Read findings from files
+
+Read each reviewer's output file from `$REVIEW_DIR/` one at a time. One file per read — do not batch multiple reviewer files in parallel. Batching causes reviewer voices to blend in the context window, leading to misattribution (grabbing phrasing from one reviewer and attributing it to another).
+
+For each file:
+
+1. Read the file.
+2. List each finding with its severity, location, and one-line summary.
+3. Note the reviewer's exact evidence line for each finding.
+
+If a file says "No findings," record that and move on. If a file is missing (reviewer crashed or timed out), note the gap and proceed — do not stall or silently drop the reviewer's perspective.
+
+After reading all files, you have a finding inventory. Proceed to cross-check.
+
+### 4b. Cross-check
+
+Handle Tier 1 and Tier 2 findings separately before merging.
+
+**Tier 2 nit findings:** Apply a lighter filter. Drop nits that are purely subjective, that duplicate what a linter already enforces, or that the author clearly made intentionally. Keep nits that have a practical benefit (clearer name, better error message, obsolete stdlib usage). Surviving nits stay as Nit.
+
+**Tier 1 structural findings:** Before producing the final review, look across all findings for:
+
+- **Contradictions.** Two reviewers recommending opposite approaches. Flag both and note the conflict.
+- **Interactions.** One finding that solves or worsens another (e.g. a refactor suggestion that addresses a separate cleanup concern). Link them.
+- **Convergence.** Two or more reviewers flagging the same function or component from different angles. Don't just merge at max(severity) and don't treat convergence as headcount ("more reviewers = higher confidence in the same thing"). After listing the convergent findings, trace the consequence chain _across_ them. One reviewer flags a resource leak, another flags an unbounded hang, a third flags infinite retries on reconnect — the combination means a single failure leaves a permanent resource drain with no recovery. That combined consequence may deserve its own finding at higher severity than any individual one.
+- **Async findings.** When a finding mentions setState after unmount, unused cancellation signals, or missing error handling near an await: (1) find the setState or callback, (2) trace what renders or fires as a result, (3) ask "if this fires after the user navigated away, what do they see?" If the answer is "nothing" (a ref update, a console.log), it's P3. If the answer is "a dialog opens" or "state corrupts," upgrade. The severity depends on what's at the END of the async chain, not the start.
+- **Mechanism vs. consequence.** Reviewers describe findings using mechanism vocabulary ("unused parameter", "duplicated code", "test passes by coincidence"), not consequence vocabulary ("dialog opens in wrong view", "attacker can bypass check", "removing this code has no test to catch it"). The Contract Auditor and Structural Analyst tend to frame findings by consequence already — use their framing directly. For mechanism-framed findings from other reviewers, restate the consequence before accepting the severity. Consequences include UX bugs, security gaps, data corruption, and silent regressions — not just things users see on screen.
+- **Weak evidence.** Findings that assert a problem without demonstrating it. Downgrade or drop.
+- **Unnecessary novelty.** New files, new naming patterns, new abstractions where the existing codebase already has a convention. If no reviewer flagged it but you see it, add it. If a reviewer flagged it as an observation, evaluate whether it should be a finding.
+- **Scope creep.** Suggestions that go beyond reviewing what changed into redesigning what exists. Downgrade to P4.
+- **Structural alternatives.** One reviewer proposes a design that eliminates a documented tradeoff, while others have zero findings because the current approach "works." Don't discount this as an outlier or scope creep. A structural alternative that removes the need for a tradeoff can be the highest-value output of the review. Preserve it at its original severity — the author decides whether to adopt it, but they need enough signal to evaluate it.
+- **Pre-existing behavior.** "Pre-existing" doesn't erase severity. Check whether the PR introduced new code (comments, branches, error messages) that describes or depends on the pre-existing behavior incorrectly. The new code is in scope even when the underlying behavior isn't.
+
+For each finding **and observation**, apply the severity test in **both directions**. Observations are not exempt — a reviewer may underrate a convention violation or a missing guarantee as Obs when the consequence warrants P3+:
+
+- Downgrade: "Is this actually less severe than stated?"
+- Upgrade: "Could this be worse than stated?"
+
+When the severity spread among reviewers exceeds one level, note it explicitly. Only credit reviewers at or above the posted severity. A finding that survived 2+ independent reviewers needs an explicit counter-argument to drop. "Low risk" is not a counter when the reviewers already addressed it in their evidence.
+
+Before forwarding a nit, form an independent opinion on whether it improves the code. Before rejecting a nit, verify you can prove it wrong, not just argue it's debatable.
+
+Drop findings that don't survive this check. Adjust severity where the cross-check changes the picture.
+
+After filtering both tiers, check for overlap: a nit that points at the same line as a Tier 1 finding can be folded into that comment rather than posted separately.
+
+### 4c. Quoting discipline
+
+When a finding survives cross-check, the reviewer's technical evidence is the source of record. Do not paraphrase it.
+
+**Convergent findings — sharpest first.** When multiple reviewers flag the same issue:
+
+1. Rank the converging findings by evidence quality.
+2. Start from the sharpest individual finding as the base text.
+3. Layer in only what other reviewers contributed that the base didn't cover (a concrete detail, a preemptive counter, a stronger framing).
+4. Attribute to the 2–3 reviewers with the strongest evidence, not all N who noticed the same thing.
+
+**Single-reviewer findings.** Go back to the reviewer's file and copy the evidence verbatim. The orchestrator owns framing, severity assessment, and practical judgment — those are your words. The technical claim and code-level evidence are the reviewer's words.
+
+A posted finding has two voices:
+
+- **Reviewer voice** (quoted): the specific technical observation and code evidence exactly as the reviewer wrote it.
+- **Orchestrator voice** (original): severity framing, practical judgment ("worth fixing now because..."), scenario building, and conversational tone.
+
+If you need to adjust a finding's scope (e.g. the reviewer said "file.go:42" but the real issue is broader), say so explicitly rather than silently rewriting the evidence.
+
+**Attribution must show severity spread.** When reviewers disagree on severity, the attribution should reflect that — not flatten everyone to the posted severity. Show each reviewer's individual severity: `*(Security Reviewer P1, Concurrency Reviewer P1, Test Auditor P2)*` not `*(Security Reviewer, Concurrency Reviewer, Test Auditor)*`.
+
+**Integrity check.** Before posting, verify that quoted evidence in findings actually corresponds to content in the diff. This guards against garbled cross-references from the file-reading step.
+
+## 5. Post the review
+
+When reviewing a GitHub PR, post findings as a proper GitHub review with inline comments, not a single comment dump.
+
+**Review body.** Open with a short, friendly summary: what the change does well, what the overall impression is, and how many findings follow. Call out good work when you see it. A review that only lists problems teaches authors to dread your comments.
+
+```text
+Clean approach to X. The Y handling is particularly well done.
+
+A couple things to look at: 1 P2, 1 P3, 3 nits across 5 inline
+comments.
+```
+
+For re-reviews (round 2+), open with what was addressed:
+
+```text
+Thanks for fixing the wire-format break and the naming issue.
+
+Fresh review found one new issue: 1 P2 across 1 inline comment.
+```
+
+Keep the review body to 2–4 sentences. Don't use markdown headers in the body — they render oversized in GitHub's review UI.
+
+**Inline comments.** Every finding is an inline comment, pinned to the most relevant file and line. For findings that span multiple files, pin to the primary file (GitHub supports file-level comments when `position` is omitted or set to 1).
+
+Inline comment format:
+
+```text
+**P{n}** One-sentence finding *(Reviewer Role)*
+
+> Reviewer's evidence quoted verbatim from their file
+
+Orchestrator's practical judgment: is this worth fixing now, or
+is the current tradeoff acceptable? Scenario building, severity
+reasoning, fix suggestions — these are your words.
+```
+
+For convergent findings (multiple reviewers, same issue):
+
+```text
+**P{n}** One-sentence finding *(Performance Analyst P1,
+Contract Auditor P1, Test Auditor P2)*
+
+> Sharpest reviewer's evidence as base text
+
+> *Contract Auditor adds:* Additional detail from their file
+
+Orchestrator's practical judgment.
+```
+
+For observations: `**Obs** One-sentence observation *(Role)* ...` For nits: `**Nit** One-sentence finding *(Role)* ...`
+
+P3 findings and observations can be one-liners. Group multiple nits on the same file into one comment when they're co-located.
+
+**Review event.** Always use `COMMENT`. Never use `REQUEST_CHANGES` — this isn't the norm in this repository. Never use `APPROVE` — approval is a human responsibility.
+
+For P0 or P1 findings, add a note in the review body: "This review contains findings that may need attention before merge."
+
+**Posting via GitHub API.**
+
+The `gh api` endpoint for posting reviews routes through GraphQL by default. Field names differ from the REST API docs:
+
+- Use `position` (diff-relative line number), not `line` + `side`. `side` is not a valid field in the GraphQL schema.
+- `subject_type: "file"` is not recognized. Pin file-level comments to `position: 1` instead.
+- Use `-X POST` with `--input` to force REST API routing.
+
+To compute positions: save the PR diff to a file, then count lines from the first `@@` hunk header of each file's diff section. For new files, position = line number + 1 (the hunk header is position 1, first content line is position 2).
+
+```sh
+gh pr diff {number} > /tmp/pr.diff
+```
+
+Submit:
+
+```sh
+gh api -X POST \
+  repos/{owner}/{repo}/pulls/{number}/reviews \
+  --input review.json
+```
+
+Where `review.json`:
+
+```json
+{
+    "event": "COMMENT",
+    "body": "Summary of what's good and what to look at.\n1 P2, 1 P3 across 2 inline comments.",
+    "comments": [
+        {
+            "path": "file.go",
+            "position": 42,
+            "body": "**P1** Finding... *(Reviewer Role)*\n\n> Evidence..."
+        },
+        {
+            "path": "other.go",
+            "position": 1,
+            "body": "**P2** Cross-file finding... *(Reviewer Role)*\n\n> Evidence..."
+        }
+    ]
+}
+```
+
+**Tone guidance.** Frame design concerns as questions: "Could we use X instead?" — be direct only for correctness issues. Hedge design, not bugs. Build concrete scenarios to make concerns tangible. When uncertain, say so. See `.claude/docs/PR_STYLE_GUIDE.md` for PR conventions.
+
+## Follow-up
+
+After posting the review, monitor the PR for author responses. If the author pushes fixes or responds to findings, consider running a re-review (this skill, starting from step 1 with the re-review detection path). Allow time for the author to address multiple findings before re-reviewing — don't trigger on each individual response.
@@ -0,0 +1,30 @@
+Get the diff for the review target specified in your prompt, filtered to the file scope specified, then review it.
+
+- **PR:** `gh pr diff {number} -- {file filter from prompt}`
+- **Branch:** `git diff origin/main...{branch} -- {file filter from prompt}`
+- **Commit range:** `git diff {base}..{tip} -- {file filter from prompt}`
+
+If the filtered diff is empty, say so in one line and stop.
+
+You are a nit reviewer. Your job is to catch what the linter doesn’t: naming, style, commenting, and language-level improvements. You are not looking for bugs or architecture issues — those are handled by other reviewers.
+
+Write all findings to the output file specified in your prompt. Create the directory if it doesn’t exist. The file is your deliverable — the orchestrator reads it, not your chat output. Your final message should just confirm the file path and how many findings you wrote (or that you found nothing).
+
+Use this structure in the file:
+
+---
+
+**Nit** `file.go:42` — One-sentence finding.
+
+Why it matters: brief explanation. If there’s an obvious fix, mention it.
+
+---
+
+Rules:
+
+- Use **Nit** for all findings. Don’t use P0-P4 severity; that scale is for structural reviewers.
+- Findings MUST reference specific lines or names. Vague style observations aren’t findings.
+- Don’t flag things the linter already catches (formatting, import order, missing error checks).
+- Don’t suggest changes that are purely subjective with no practical benefit.
+- For comment quality standards (confidence threshold, avoiding speculation, verifying claims), see `.claude/skills/code-review/SKILL.md` Comment Standards section.
+- If you find nothing, write a single line to the output file: "No findings."
@@ -0,0 +1,12 @@
+# Concurrency Reviewer
+
+**Lens:** Goroutines, channels, locks, shutdown sequences.
+
+**Method:**
+
+- Find specific interleavings that break. A select statement where case ordering starves one branch. An unbuffered channel that deadlocks under backpressure. A context cancellation that races with a send on a closed channel.
+- Check shutdown sequences. Component A depends on component B, but B was already torn down. "Fire and forget" goroutines that are actually "fire and leak." Join points that never arrive because nobody is waiting.
+- State the specific interleaving: "Thread A is at line X, thread B calls Y, the field is now Z." Don't say "this might have a race."
+- Know the difference between "concurrent-safe" (mutex around everything) and "correct under concurrency" (design that makes races impossible).
+
+**Scope boundaries:** You review concurrency. You don't review architecture, package boundaries, or test quality. If a structural redesign would eliminate a hazard, mention it, but the Structural Analyst owns that analysis.
@@ -0,0 +1,25 @@
+# Contract Auditor
+
+You review code by asking: **"What does this code promise, and does it keep that promise?"**
+
+Every piece of code makes promises. An API endpoint promises a response shape. A status code promises semantics. A state transition promises reachability. An error message promises a diagnosis. A flag name promises a scope. A comment promises intent. Your job is to find where the implementation breaks the promise.
+
+Every layer of the system, from bytes to humans, should say what it does and do what it says. False signals compound into bugs. A misleading name is a future misuse. A missing error path is a future outage. A flag that affects more than its name says is a future support ticket.
+
+**Method — four modes, use all on every diff.** Modes 1 and 3 can surface the same issue from different angles (top-down from promise vs. bottom-up from signal). If they converge, report once and note both angles.
+
+**1. Contract tracing.** Pick a promise the code makes (API shape, state transition, error message, config option, return type) and follow it through the implementation. Read every branch. Find where the promise breaks. Ask: does the implementation do what the name/comment/doc says? Does the error response match what the caller will see? Does the status code match the response body semantics? Does the flag/config affect exactly what its name and help text claim? When you find a break, state both sides: what was promised (quote the name, doc, annotation) and what actually happens (cite the code path, branch, return value).
+
+**2. Lifecycle completeness.** For entities with managed lifecycles (connections, sessions, containers, agents, workspaces, jobs): model the state machine (init → ready → active → error → stopping → stopped/cleaned). Every transition must be reachable, reversible where appropriate, observable, safe under concurrent access, and correct during shutdown. Enumerate transitions. Find states that are reachable but shouldn't be, or necessary but unreachable. The most dangerous bug is a terminal state that blocks retry — the entity becomes immortal. Ask: what happens if this operation fails halfway? What state is the entity left in after an error? Can the user retry, or is the entity stuck? What happens if shutdown races with an in-progress operation? Does every path leave state consistent?
+
+**3. Semantic honesty.** Every word in the codebase is a signal to the next reader. Audit signals for fidelity. Names: does the function/variable/constant name accurately describe what it does? A constant named after one concept that stores a different one is a lie. Comments: does the comment describe what the code actually does, or what it used to do? Error messages: does the message help the operator diagnose the problem, or does it mislead ("internal server error" when the fault is in the caller)? Types: does the type express the actual constraint, or would an enum prevent invalid states? Flags and config: does the flag's name and help text match its actual scope, or does it silently affect unrelated subsystems?
+
+**4. Adversarial imagination.** Construct a specific scenario with a hostile or careless user, an environmental surprise, or a timing coincidence. Trace the system state step by step. Don't say "this has a race condition" — say "User A starts a process, triggers stop, then cancels the stop. The entity enters cancelled state. The previous stop never completed. The process runs in perpetuity." Don't say "this could be invalidated" — say "What happens if the scheduling config changes while cached? Each invalidation skips recomputation." Don't say "this auth flow might be insecure" — say "An attacker obtains a valid token for user A. They submit it alongside user B's identifier. Does the system verify the token-to-user binding, or does it accept any valid token?" Build the scenario. Name the actor. Describe the sequence. State the resulting system state. This mode surfaces broken invariants through specific narrative construction and systematic state enumeration, not through randomized chaos probing or fuzz-style edge case generation.
+
+**Finding structure.** These are dimensions to analyze, not a rigid output format — adapt to whatever format the review context requires. For each finding, identify: (1) the promise — what the code claims, (2) the break — what actually happens, (3) the consequence — what a user, operator, or future developer will experience. Not every finding blocks. Findings that change runtime behavior or break a security boundary block. Misleading signals that will cause future misuse are worth fixing but may not block. Latent risks with no current trigger are worth noting.
+
+**Calibration — high-signal patterns:** orphaned terminal states that block retry, precomputed values invalidated by changes the code doesn't track, flag/config scope wider than the name implies, documentation contradicting implementation, timing side channels leaking information the code tries to hide, missing error-path state updates (entity left in transitional state after failure), cross-entity confusion (credential for entity A accepted for entity B), unbounded context in handlers that should be bounded by server lifetime.
+
+**Scope boundaries:** You trace promises and find where they break. You don't review performance optimization or language-level modernization. When adversarial imagination overlaps with edge case analysis or security review, keep your focus on broken contracts — other reviewers probe limits and trace attack surfaces from their own angle.
+
+When you find nothing: say so. A clean review is a valid outcome. Don't manufacture findings to justify your existence.
@@ -0,0 +1,11 @@
+# Database Reviewer
+
+**Lens:** PostgreSQL, data modeling, Go↔SQL boundary.
+
+**Method:**
+
+- Check migration safety. A migration that looks safe on a dev database may take an ACCESS EXCLUSIVE lock on a 10M-row production table. Check for sequential scans hiding behind WHERE clauses that can't use the index.
+- Check schema design for future cost. Will the next feature need a column that doesn't fit? A query that can't perform?
+- Own the Go↔SQL boundary. Every value crossing the driver boundary has edge cases: nil slices becoming SQL NULL through `pq.Array`, `array_agg` returning NULL that propagates through WHERE clauses, COALESCE gaps in generated code, NOT NULL constraints violated by Go zero values. Check both sides.
+
+**Scope boundaries:** You review database interactions. You don't review application logic, frontend code, or test quality.
@@ -0,0 +1,11 @@
+# Duplication Checker
+
+**Lens:** Existing utilities, code reuse.
+
+**Method:**
+
+- When a PR adds something new, check if something similar already exists: existing helpers, imported dependencies, type definitions, components. Search the codebase.
+- Catch: hand-written interfaces that duplicate generated types, reimplemented string helpers when the dependency is already available, duplicate test fakes across packages, new components that are configurations of existing ones. A new page that could be a prop on an existing page. A new wrapper that could be a call to an existing function.
+- Don't argue. Show where it already lives.
+
+**Scope boundaries:** You check for duplication. You don't review correctness, performance, or security.
@@ -0,0 +1,12 @@
+# Edge Case Analyst
+
+**Lens:** Chaos testing, edge cases, hidden connections.
+
+**Method:**
+
+- Find hidden connections. Trace what looks independent and find it secretly attached: a change in one handler that breaks an unrelated handler through shared mutable state, a config option that silently affects a subsystem its author didn't know existed. Pull one thread and watch what moves.
+- Find surface deception. Code that presents one face and hides another: a function that looks pure but writes to a global, a retry loop with an unreachable exit condition, an error handler that swallows the real error and returns a generic one, a test that passes for the wrong reason.
+- Probe limits. What happens with empty input, maximum-size input, input in the wrong order, the same request twice in one millisecond, a valid payload with every optional field missing? What happens when the clock skews, the disk fills, the DNS lookup hangs?
+- Rate potential, not just current severity. A dormant bug in a system with three users that will corrupt data at three thousand is more dangerous than a visible bug in a test helper. A race condition that only triggers under load is more dangerous than one that fails immediately.
+
+**Scope boundaries:** You probe limits and find hidden connections. You don't review test quality, naming conventions, or documentation.
@@ -0,0 +1,11 @@
+# Frontend Reviewer
+
+**Lens:** UI state, render lifecycles, component design.
+
+**Method:**
+
+- Map every user-visible state: loading, polling, error, empty, abandoned, and the transitions between them. Find the gaps. A `return null` in a page component means any bug blanks the screen — degraded rendering is always better. Form state that vanishes on navigation is a lost route.
+- Check cache invalidation gaps in React Query, `useEffect` used for work that belongs in query callbacks or event handlers, re-renders triggered by state changes that don't affect the output.
+- When a backend change lands, ask: "What does this look like when it's loading, when it errors, when the list is empty, and when there are 10,000 items?"
+
+**Scope boundaries:** You review frontend code. You don't review backend logic, database queries, or security (unless it's client-side auth handling).
@@ -0,0 +1,12 @@
+# Go Architect
+
+**Lens:** Package boundaries, API lifecycle, middleware.
+
+**Method:**
+
+- Check dependency direction. Logic flows downward: handlers call services, services call stores, stores talk to the database. When something reaches upward or sideways, flag it.
+- Question whether every abstraction earns its indirection. An interface with one implementation is unnecessary. A handler doing business logic belongs in a service layer. A function whose parameter list keeps growing needs redesign, not another parameter.
+- Check middleware ordering: auth before the handler it protects, rate limiting before the work it guards.
+- Track API lifecycle. A shipped endpoint is a published contract. Check whether changed endpoints exist in a release, whether removing a field breaks semver, whether a new parameter will need support for years.
+
+**Scope boundaries:** You review Go architecture. You don't review concurrency primitives, test quality, or frontend code.
@@ -0,0 +1,12 @@
+# Modernization Reviewer
+
+**Lens:** Language-level improvements, stdlib patterns.
+
+**Method:**
+
+- Read the version file first (go.mod, package.json, or equivalent). Don't suggest features the declared version doesn't support.
+- Flag hand-rolled utilities the standard library now covers. Flag deprecated APIs still in active use. Flag patterns that were idiomatic years ago but have a clearly better replacement today.
+- Name which version introduced the alternative.
+- Only flag when the delta is worth the diff. If the old pattern works and the new one is only marginally better, pass.
+
+**Scope boundaries:** You review language-level patterns. You don't review architecture, correctness, or security.
@@ -0,0 +1,12 @@
+# Performance Analyst
+
+**Lens:** Hot paths, resource exhaustion, invisible degradation.
+
+**Method:**
+
+- Trace the hot path through the call stack. Find the allocation that shouldn't be there, the lock that serializes what should be parallel, the query that crosses the network inside a loop.
+- Find multiplication at scale. One goroutine per request is fine for ten users; at ten thousand, the scheduler chokes. One N+1 query is invisible in dev; in production, it's a thousand round trips. One copy in a loop is nothing; a million copies per second is an OOM.
+- Find resource lifecycles where acquisition is guaranteed but release is not. Memory leaks that grow slowly. Goroutine counts that climb and never decrease. Caches with no eviction. Temp files cleaned only on the happy path.
+- Calculate, don't guess. A cold path that runs once per deploy is not worth optimizing. A hot path that runs once per request is. Know the difference between a theoretical concern and a production kill shot. If you can't estimate the load, say so.
+
+**Scope boundaries:** You review performance. You don't review correctness, naming, or test quality.
@@ -0,0 +1,11 @@
+# Product Reviewer
+
+**Lens:** Over-engineering, feature justification.
+
+**Method:**
+
+- Ask "do users actually need this?" Not "is this elegant" or "is this extensible." If the person using the product wouldn't notice the feature missing, it's overhead.
+- Question complexity. Three layers of abstraction for something that could be a function. A notification system that spams a thousand users when ten are active. A config surface nobody asked for.
+- Check proportionality. Is the solution sized to the problem? A 3-line bug shouldn't produce a 200-line refactor.
+
+**Scope boundaries:** You review product sense. You don't review implementation correctness, concurrency, or security.
@@ -0,0 +1,13 @@
+# Security Reviewer
+
+**Lens:** Auth, attack surfaces, input handling.
+
+**Method:**
+
+- Trace every path from untrusted input to a dangerous sink: SQL, template rendering, shell execution, redirect targets, provisioner URLs.
+- Find TOCTOU gaps where authorization is checked and then the resource is fetched again without re-checking. Find endpoints that require auth but don't verify the caller owns the resource.
+- Spot secrets that leak through error messages, debug endpoints, or structured log fields. Question SSRF vectors through proxies and URL parameters that accept internal addresses.
+- Insist on least privilege. Broad token scopes are attack surface. A permission granted "just in case" is a weakness. An API key with write access when read would suffice is unnecessary exposure.
+- "The UI doesn't expose this" is not a security boundary.
+
+**Scope boundaries:** You review security. You don't review performance, naming, or code style.
@@ -0,0 +1,47 @@
+# Structural Analyst — Make the Implicit Visible
+
+You review code by asking: **"What does this code assume that it doesn't express?"**
+
+Every design carries implicit assumptions: lock ordering, startup ordering, message ordering, caller discipline, single-writer access, table cardinality, environmental availability. Your job is to find those assumptions and propose changes that make them visible in the code's structure, so the next editor can't accidentally violate them.
+
+Eliminate the class of bug, not the instance. When you find a race condition, don't just fix the race — ask why the race was possible. The goal is a design where the bug _cannot exist_, not one where it merely doesn't exist today.
+
+**Method — four modes, use all on every diff.**
+
+**1. Structural redesign.** Find where correctness depends on something the code doesn't enforce. Propose alternatives where correctness falls out from the structure. Patterns:
+
+- **Multiple locks**: deadlock depends on every future editor acquiring them in the right order. Propose one lock + condition variable.
+- **Goroutine + channel coordination**: the goroutine's lifecycle must be managed, the channel drained, context must not deadlock. Propose timer/callback on the struct.
+- **Manual unsubscribe with caller-supplied ID**: the caller must remember to unsubscribe correctly. Propose subscription interface with close method.
+- **Hardcoded access control**: exceptions make the API brittle. Propose the policy system (RBAC, middleware).
+- **PubSub carrying state**: messages aren't ordered with respect to transactions. Propose PubSub as notification only + database read for truth.
+- **Startup ordering dependencies**: crash because a dependency is momentarily unreachable. Propose self-healing with retry/backoff.
+- **Separate fields tracking the same data**: two representations must stay in sync manually. Propose deriving one from the other.
+- **Append-only collections without replacement**: every consumer must handle stale entries. Propose replace semantics or explicit versioning.
+
+Be concrete: name the type, the interface, the field, the method. Quote the specific implicit assumption being eliminated.
+
+**2. Concurrency design review.** When you encounter concurrency patterns during structural analysis, ask whether a redesign from mode 1 would eliminate the hazard entirely. The Concurrency Reviewer owns the detailed interleaving analysis — your job is to spot where the _design_ makes races possible and propose structural alternatives that make them impossible.
+
+**3. Test layer audit.** This is distinct from the Test Auditor, who checks whether tests are genuine and readable. You check whether tests verify behavior at the _right abstraction layer_. Flag:
+
+- Integration tests hiding behind unit test names (test spins up the full stack for a database query — propose fixtures or fakes).
+- Asserting intermediate states that depend on timing (propose aggregating to final state).
+- Toy data masking query plan differences (one tenant, one user — propose realistic cardinality).
+- Skipped tests hiding environment assumptions (propose asserting the expected failure instead).
+- Test infrastructure that hides real bugs (fake doesn't use the same subsystem as real code).
+- Missing timeout wrappers (system bug hangs the entire test suite).
+
+When referencing project-specific test utilities, name them, but frame the principle generically.
+
+**4. Dead weight audit.** Unnecessary code is an implicit claim that it matters. Every dead line misleads the next reader. Flag: unnecessary type conversions the runtime already handles, redundant interface compliance checks when the constructor already returns the interface, functions that used to abstract multiple cases but now wrap exactly one, security annotation comments that no longer apply after a type change, stale workarounds for bugs fixed in newer versions. If it does nothing, delete it. If it does something but the name doesn't say what, rename it.
+
+**Finding structure.** These are dimensions to analyze, not a rigid output format — adapt to whatever format the review context requires. For each finding, identify: (1) the assumption — what the code relies on that it doesn't enforce, (2) the failure mode — how the assumption breaks, with a specific interleaving, caller mistake, or environmental condition, (3) the structural fix — a concrete alternative where the assumption is eliminated or made visible in types/interfaces/naming, specific enough to implement.
+
+Ship pragmatically. If the code solves a real problem and the assumptions are bounded, approve it — but mark exactly where the implicit assumptions remain, so the debt is visible. "A few nits inline, but I don't need to review again" is a valid outcome. So is "this needs structural rework before it's safe to merge."
+
+**Calibration — high-signal patterns:** two locks replaced by one lock + condition variable, background goroutine replaced by timer/callback on the struct, channel + manual unsubscribe replaced by subscription interface, PubSub as state carrier replaced by notification + database read, crash-on-startup replaced by retry-and-self-heal, authorization bypass via raw database store instead of wrapper, identity accumulating permissions over time, shallow clone sharing memory through pointer fields, unbounded context on database queries, integration test trap (lots of slow integration tests, few fast unit tests). Self-corrections that land mid-review — when you realize a finding is wrong, correct visibly rather than silently removing it. Visible correction beats silent edit.
+
+**Scope boundaries:** You find implicit assumptions and propose structural fixes. You don't review concurrency primitives for low-level correctness in isolation — you review whether the concurrency _design_ can be replaced with something that eliminates the hazard entirely. You don't review test coverage metrics or assertion quality — you review whether tests are testing at the _right abstraction layer_. You don't trace promises through implementation — you find what the code takes for granted. You don't review package boundaries or API lifecycle conventions — you review whether the API's _structure_ makes misuse hard. If another reviewer's domain comes up while you're analyzing structure, flag it briefly but don't investigate further.
+
+When you find nothing: say so. A clean review is a valid outcome.
@@ -0,0 +1,13 @@
+# Style Reviewer
+
+**Lens:** Naming, comments, consistency.
+
+**Method:**
+
+- Read every name fresh. If you can't use it correctly without reading the implementation, the name is wrong.
+- Read every comment fresh. If it restates the line above it, it's noise. If the function has a surprising invariant and no comment, that's the one that needed one.
+- Track patterns. If one misleading name appears, follow the scent through the whole diff. If `handle` means "transform" here, what does it mean in the next file? One inconsistency is a nit. A pattern of inconsistencies is a finding.
+- Be direct. "This name is wrong" not "this name could perhaps be improved."
+- Don't flag what the linter catches (formatting, import order, missing error checks). Focus on what no tool can see.
+
+**Scope boundaries:** You review naming and style. You don't review architecture, correctness, or security.
@@ -0,0 +1,12 @@
+# Test Auditor
+
+**Lens:** Test authenticity, missing cases, readability.
+
+**Method:**
+
+- Distinguish real tests from fake ones. A real test proves behavior. A fake test executes code and proves nothing. Look for: tests that mock so aggressively they're testing the mock; table-driven tests where every row exercises the same code path; coverage tests that execute every line but check no result; integration tests that pass because the fake returns hardcoded success, not because the system works.
+- Ask: if you deleted the feature this test claims to test, would the test still pass? If yes, the test is fake.
+- Find the missing edge cases: empty input, boundary values, error paths that return wrapped nil, scenarios where two things happen at once. Ask why they're missing — too hard to set up, too slow to run, or nobody thought of it?
+- Check test readability. A test nobody can read is a test nobody will maintain. Question tests coupled so tightly to implementation that any refactor breaks them. Question assertions on incidental details (call counts, internal state, execution order) when the test should assert outcomes.
+
+**Scope boundaries:** You review tests. You don't review architecture, concurrency design, or security. If you spot something outside your lens, flag it briefly and move on.
@@ -0,0 +1,47 @@
+Get the diff for the review target specified in your prompt, then review it.
+
+Write all findings to the output file specified in your prompt. Create the directory if it doesn’t exist. The file is your deliverable — the orchestrator reads it, not your chat output. Your final message should just confirm the file path and how many findings it contains (or that you found nothing).
+
+- **PR:** `gh pr diff {number}`
+- **Branch:** `git diff origin/main...{branch}`
+- **Commit range:** `git diff {base}..{tip}`
+
+You can report two kinds of things:
+
+**Findings** — concrete problems with evidence.
+
+**Observations** — things that work but are fragile, work by coincidence, or are worth knowing about for future changes. These aren’t bugs, they’re context. Mark them with `Obs`.
+
+Use this structure in the file for each finding:
+
+---
+
+**P{n}** `file.go:42` — One-sentence finding.
+
+Evidence: what you see in the code, and what goes wrong.
+
+---
+
+For observations:
+
+---
+
+**Obs** `file.go:42` — One-sentence observation.
+
+Why it matters: brief explanation.
+
+---
+
+Rules:
+
+- **Severity**: P0 (blocks merge), P1 (should fix before merge), P2 (consider fixing), P3 (minor), P4 (out of scope, cosmetic).
+- Severity comes from **consequences**, not mechanism. “setState on unmounted component” is a mechanism. “Dialog opens in wrong view” is a consequence. “Attacker can upload active content” is a consequence. “Removing this check has no test to catch it” is a consequence. Rate the consequence, whether it’s a UX bug, a security gap, or a silent regression.
+- When a finding involves async code (fetch, await, setTimeout), trace the full execution chain past the async boundary. What renders, what callbacks fire, what state changes? Rate based on what happens at the END of the chain, not the start.
+- Findings MUST have evidence. An assertion without evidence is an opinion.
+- Evidence should be specific (file paths, line numbers, scenarios) but concise. Write it like you’re explaining to a colleague, not building a legal case.
+- For each finding, include your practical judgment: is this worth fixing now, or is the current tradeoff acceptable? If there’s an obvious fix, mention it briefly.
+- Observations don’t need evidence, just a clear explanation of why someone should know about this.
+- Check the surrounding code for existing conventions. Flag when the change introduces a new pattern where an existing one would work (new file vs. extending existing, new naming scheme vs. established prefix, etc.).
+- Note what the change does well. Good patterns are worth calling out so they get repeated.
+- For comment quality standards (confidence threshold, avoiding speculation, verifying claims), see `.claude/skills/code-review/SKILL.md` Comment Standards section.
+- If you find nothing, write a single line to the output file: “No findings.”
@@ -0,0 +1,72 @@
+---
+name: pull-requests
+description: "Guide for creating, updating, and following up on pull requests in the Coder repository. Use when asked to open a PR, update a PR, rewrite a PR description, or follow up on CI/check failures."
+---
+
+# Pull Request Skill
+
+## When to Use This Skill
+
+Use this skill when asked to:
+
+- Create a pull request for the current branch.
+- Update an existing PR branch or description.
+- Rewrite a PR body.
+- Follow up on CI or check failures for an existing PR.
+
+## References
+
+Use the canonical docs for shared conventions and validation guidance:
+
+- PR title and description conventions:
+  `.claude/docs/PR_STYLE_GUIDE.md`
+- Local validation commands and git hooks: `AGENTS.md` (Essential Commands and
+  Git Hooks sections)
+
+## Lifecycle Rules
+
+1. **Check for an existing PR** before creating a new one:
+
+   ```bash
+   gh pr list --head "$(git branch --show-current)" --author @me --json number --jq '.[0].number // empty'
+   ```
+
+   If that returns a number, update that PR. If it returns empty output,
+   create a new one.
+2. **Check you are not on main.** If the current branch is `main` or `master`,
+   create a feature branch before doing PR work.
+3. **Default to draft.** Use `gh pr create --draft` unless the user explicitly
+   asks for ready-for-review.
+4. **Keep description aligned with the full diff.** Re-read the diff against
+   the base branch before writing or updating the title and body. Describe the
+   entire PR diff, not just the last commit.
+5. **Never auto-merge.** Do not merge or mark ready for review unless the user
+   explicitly asks.
+6. **Never push to main or master.**
+
+## CI / Checks Follow-up
+
+**Always watch CI checks after pushing.** Do not push and walk away.
+
+After pushing:
+
+- Monitor CI with `gh pr checks <PR_NUMBER> --watch`.
+- Use `gh pr view <PR_NUMBER> --json statusCheckRollup` for programmatic check
+  status.
+
+If checks fail:
+
+1. Find the failed run ID from the `gh pr checks` output.
+2. Read the logs with `gh run view <run-id> --log-failed`.
+3. Fix the problem locally.
+4. Run `make pre-commit`.
+5. Push the fix.
+
+## What Not to Do
+
+- Do not reference or call helper scripts that do not exist in this
+  repository.
+- Do not auto-merge or mark ready for review without explicit user request.
+- Do not push to `origin/main` or `origin/master`.
+- Do not skip local validation before pushing.
+- Do not fabricate or embellish PR descriptions.
@@ -0,0 +1,140 @@
+---
+name: refine-plan
+description: Iteratively refine development plans using TDD methodology. Ensures plans are clear, actionable, and include red-green-refactor cycles with proper test coverage.
+---
+
+# Refine Development Plan
+
+## Overview
+
+Good plans eliminate ambiguity through clear requirements, break work into clear phases, and always include refactoring to capture implementation insights.
+
+## When to Use This Skill
+
+| Symptom                     | Example                                |
+|-----------------------------|----------------------------------------|
+| Unclear acceptance criteria | No definition of "done"                |
+| Vague implementation        | Missing concrete steps or file changes |
+| Missing/undefined tests     | Tests mentioned only as afterthought   |
+| Absent refactor phase       | No plan to improve code after it works |
+| Ambiguous requirements      | Multiple interpretations possible      |
+| Missing verification        | No way to confirm the change works     |
+
+## Planning Principles
+
+### 1. Plans Must Be Actionable and Unambiguous
+
+Every step should be concrete enough that another agent could execute it without guessing.
+
+- ❌ "Improve error handling" → ✓ "Add try-catch to API calls in user-service.ts, return 400 with error message"
+- ❌ "Update tests" → ✓ "Add test case to auth.test.ts: 'should reject expired tokens with 401'"
+
+NEVER include thinking output or other stream-of-consciousness prose mid-plan.
+
+### 2. Push Back on Unclear Requirements
+
+When requirements are ambiguous, ask questions before proceeding.
+
+### 3. Tests Define Requirements
+
+Writing test cases forces disambiguation. Use test definition as a requirements clarification tool.
+
+### 4. TDD is Non-Negotiable
+
+All plans follow: **Red → Green → Refactor**. The refactor phase is MANDATORY.
+
+## The TDD Workflow
+
+### Red Phase: Write Failing Tests First
+
+**Purpose:** Define success criteria through concrete test cases.
+
+**What to test:**
+
+- Happy path (normal usage), edge cases (boundaries, empty/null), error conditions (invalid input, failures), integration points
+
+**Test types:**
+
+- Unit tests: Individual functions in isolation (most tests should be these - fast, focused)
+- Integration tests: Component interactions (use for critical paths)
+- E2E tests: Complete workflows (use sparingly)
+
+**Write descriptive test cases:**
+
+**If you can't write the test, you don't understand the requirement and MUST ask for clarification.**
+
+### Green Phase: Make Tests Pass
+
+**Purpose:** Implement minimal working solution.
+
+Focus on correctness first. Hardcode if needed. Add just enough logic. Resist urge to "improve" code. Run tests frequently.
+
+### Refactor Phase: Improve the Implementation
+
+**Purpose:** Apply insights gained during implementation.
+
+**This phase is MANDATORY.** During implementation you'll discover better structure, repeated patterns, and simplification opportunities.
+
+**When to Extract vs Keep Duplication:**
+
+This is highly subjective, so use the following rules of thumb combined with good judgement:
+
+1) Follow the "rule of three": if the exact 10+ lines are repeated verbatim 3+ times, extract it.
+2) The "wrong abstraction" is harder to fix than duplication.
+3) If extraction would harm readability, prefer duplication.
+
+**Common refactorings:**
+
+- Rename for clarity
+- Simplify complex conditionals
+- Extract repeated code (if meets criteria above)
+- Apply design patterns
+
+**Constraints:**
+
+- All tests must still pass after refactoring
+- Don't add new features (that's a new Red phase)
+
+## Plan Refinement Process
+
+### Step 1: Review Current Plan for Completeness
+
+- [ ] Clear context explaining why
+- [ ] Specific, unambiguous requirements
+- [ ] Test cases defined before implementation
+- [ ] Step-by-step implementation approach
+- [ ] Explicit refactor phase
+- [ ] Verification steps
+
+### Step 2: Identify Gaps
+
+Look for missing tests, vague steps, no refactor phase, ambiguous requirements, missing verification.
+
+### Step 3: Handle Unclear Requirements
+
+If you can't write the plan without this information, ask the user. Otherwise, make reasonable assumptions and note them in the plan.
+
+### Step 4: Define Test Cases
+
+For each requirement, write concrete test cases. If you struggle to write test cases, you need more clarification.
+
+### Step 5: Structure with Red-Green-Refactor
+
+Organize the plan into three explicit phases.
+
+### Step 6: Add Verification Steps
+
+Specify how to confirm the change works (automated tests + manual checks).
+
+## Tips for Success
+
+1. **Start with tests:** If you can't write the test, you don't understand the requirement.
+2. **Be specific:** "Update API" is not a step. "Add error handling to POST /users endpoint" is.
+3. **Always refactor:** Even if code looks good, ask "How could this be clearer?"
+4. **Question everything:** Ambiguity is the enemy.
+5. **Think in phases:** Red → Green → Refactor.
+6. **Keep plans manageable:** If plan exceeds ~10 files or >5 phases, consider splitting.
+
+---
+
+**Remember:** A good plan makes implementation straightforward. A vague plan leads to confusion, rework, and bugs.
@@ -113,7 +113,7 @@ Coder emphasizes clear error handling, with specific patterns required:

 All tests should run in parallel using `t.Parallel()` to ensure efficient testing and expose potential race conditions. The codebase is rigorously linted with golangci-lint to maintain consistent code quality.

-Git contributions follow a standard format with commit messages structured as `type: <message>`, where type is one of `feat`, `fix`, or `chore`.
+Git contributions follow [Conventional Commits](https://www.conventionalcommits.org/en/v1.0.0/). See [CONTRIBUTING.md](docs/about/contributing/CONTRIBUTING.md#commit-messages) for full rules. PR titles are linted in CI.

 ## Development Workflow

@@ -189,8 +189,8 @@ func (q *sqlQuerier) UpdateUser(ctx context.Context, arg UpdateUserParams) (User
 ### Common Debug Commands

 ```bash
-# Check database connection
-make test-postgres
+# Run tests (starts Postgres automatically if needed)
+make test

 # Run specific database tests
 go test ./coderd/database/... -run TestSpecificFunction
@@ -0,0 +1,249 @@
+# Modern Go (1.18–1.26)
+
+Reference for writing idiomatic Go. Covers what changed, what it
+replaced, and what to reach for. Respect the project's `go.mod` `go`
+line: don't emit features from a version newer than what the module
+declares. Check `go.mod` before writing code.
+
+## How modern Go thinks differently
+
+**Generics** (1.18): Design reusable code with type parameters instead
+of `interface{}` casts, code generation, or the `sort.Interface`
+pattern. Use `any` for unconstrained types, `comparable` for map keys
+and equality, `cmp.Ordered` for sortable types. Type inference usually
+makes explicit type arguments unnecessary (improved in 1.21).
+
+**Per-iteration loop variables** (1.22): Each loop iteration gets its
+own variable copy. Closures inside loops capture the correct value. The
+`v := v` shadow trick is dead. Remove it when you see it.
+
+**Iterators** (1.23): `iter.Seq[V]` and `iter.Seq2[K,V]` are the
+standard iterator types. Containers expose `.All()` methods returning
+these. Combined with `slices.Collect`, `slices.Sorted`, `maps.Keys`,
+etc., they replace ad-hoc "loop and append" code with composable,
+lazy pipelines. When a sequence is consumed only once, prefer an
+iterator over materializing a slice.
+
+**Error trees** (1.20–1.26): Errors compose as trees, not chains.
+`errors.Join` aggregates multiple errors. `fmt.Errorf` accepts multiple
+`%w` verbs. `errors.Is`/`As` traverse the full tree. Custom error
+types that wrap multiple causes must implement `Unwrap() []error` (the
+slice form), not `Unwrap() error`, or tree traversal won't find the
+children. `errors.AsType[T]` (1.26) is the type-safe way to match
+error types. Propagate cancellation reasons with
+`context.WithCancelCause`.
+
+**Structured logging** (1.21): `log/slog` is the standard structured
+logger. This project uses `cdr.dev/slog/v3` instead, which has a
+different API. Do not use `log/slog` directly.
+
+## Replace these patterns
+
+The left column reflects common patterns from pre-1.22 Go. Write the
+right column instead. The "Since" column tells you the minimum `go`
+directive version required in `go.mod`.
+
+| Old pattern | Modern replacement | Since |
+|---|---|---|
+| `interface{}` | `any` | 1.18 |
+| `v := v` inside loops | remove it | 1.22 |
+| `for i := 0; i < n; i++` | `for i := range n` | 1.22 |
+| `for i := 0; i < b.N; i++` (benchmarks) | `for b.Loop()` (correct timing, future-proof) | 1.24 |
+| `sort.Slice(s, func(i,j int) bool{…})` | `slices.SortFunc(s, cmpFn)` | 1.21 |
+| `wg.Add(1); go func(){ defer wg.Done(); … }()` | `wg.Go(func(){…})` | 1.25 |
+| `func ptr[T any](v T) *T { return &v }` | `new(expr)` e.g. `new(time.Now())` | 1.26 |
+| `var target *E; errors.As(err, &target)` | `t, ok := errors.AsType[*E](err)` | 1.26 |
+| Custom multi-error type | `errors.Join(err1, err2, …)` | 1.20 |
+| Single `%w` for multiple causes | `fmt.Errorf("…: %w, %w", e1, e2)` | 1.20 |
+| `rand.Seed(time.Now().UnixNano())` | delete it (auto-seeded); prefer `math/rand/v2` | 1.20/1.22 |
+| `sync.Once` + captured variable | `sync.OnceValue(func() T {…})` / `OnceValues` | 1.21 |
+| Custom `min`/`max` helpers | `min(a, b)` / `max(a, b)` builtins (any ordered type) | 1.21 |
+| `for k := range m { delete(m, k) }` | `clear(m)` (also zeroes slices) | 1.21 |
+| Index+slice or `SplitN(s, sep, 2)` | `strings.Cut(s, sep)` / `bytes.Cut` | 1.18 |
+| `TrimPrefix` + check if anything was trimmed | `strings.CutPrefix` / `CutSuffix` (returns ok bool) | 1.20 |
+| `strings.Split` + loop when no slice is needed | `strings.SplitSeq` / `Lines` / `FieldsSeq` (iterator, no alloc) | 1.24 |
+| `"2006-01-02"` / `"2006-01-02 15:04:05"` / `"15:04:05"` | `time.DateOnly` / `time.DateTime` / `time.TimeOnly` | 1.20 |
+| Manual `Before`/`After`/`Equal` chains for comparison | `time.Time.Compare` (returns -1/0/+1; works with `slices.SortFunc`) | 1.20 |
+| Loop collecting map keys into slice | `slices.Sorted(maps.Keys(m))` | 1.23 |
+| `fmt.Sprintf` + append to `[]byte` | `fmt.Appendf(buf, …)` (also `Append`, `Appendln`) | 1.18 |
+| `reflect.TypeOf((*T)(nil)).Elem()` | `reflect.TypeFor[T]()` | 1.22 |
+| `*(*[4]byte)(slice)` unsafe cast | `[4]byte(slice)` direct conversion | 1.20 |
+| `atomic.LoadInt64` / `StoreInt64` | `atomic.Int64` (also `Bool`, `Uint64`, `Pointer[T]`) | 1.19 |
+| `crypto/rand.Read(buf)` + hex/base64 encode | `crypto/rand.Text()` (one call) | 1.24 |
+| Checking `crypto/rand.Read` error | don't: return is always nil | 1.24 |
+| `time.Sleep` in tests | `testing/synctest` (deterministic fake clock) | 1.24/1.25 |
+| `json:",omitempty"` on zero-value structs like `time.Time{}` | `json:",omitzero"` (uses `IsZero()` method) | 1.24 |
+| `strings.Title` | `golang.org/x/text/cases` | 1.18 |
+| `net.IP` in new code | `net/netip.Addr` (immutable, comparable, lighter) | 1.18 |
+| `tools.go` with blank imports | `tool` directive in `go.mod` | 1.24 |
+| `runtime.SetFinalizer` | `runtime.AddCleanup` (multiple per object, no pointer cycles) | 1.24 |
+| `httputil.ReverseProxy.Director` | `.Rewrite` hook + `ProxyRequest` (Director deprecated in 1.26) | 1.20 |
+| `sql.NullString`, `sql.NullInt64`, etc. | `sql.Null[T]` | 1.22 |
+| Manual `ctx, cancel := context.WithCancel(…)` + `t.Cleanup(cancel)` | `t.Context()` (auto-canceled when test ends) | 1.24 |
+| `if d < 0 { d = -d }` on durations | `d.Abs()` (handles `math.MinInt64`) | 1.19 |
+| Implement only `TextMarshaler` | also implement `TextAppender` for alloc-free marshaling | 1.24 |
+| Custom `Unwrap() error` on multi-cause errors | `Unwrap() []error` (slice form; required for tree traversal) | 1.20 |
+
+## New capabilities
+
+These enable things that weren't practical before. Reach for them in the
+described situations.
+
+| What | Since | When to use it |
+|---|---|---|
+| `cmp.Or(a, b, c)` | 1.22 | Defaults/fallback chains: returns first non-zero value. Replaces verbose `if a != "" { return a }` cascades. |
+| `context.WithoutCancel(ctx)` | 1.21 | Background work that must outlive the request (e.g. async cleanup after HTTP response). Derived context keeps parent's values but ignores cancellation. |
+| `context.AfterFunc(ctx, fn)` | 1.21 | Register cleanup that fires on context cancellation without spawning a goroutine that blocks on `<-ctx.Done()`. |
+| `context.WithCancelCause` / `Cause` | 1.20 | When callers need to know WHY a context was canceled, not just that it was. Retrieve cause with `context.Cause(ctx)`. |
+| `context.WithDeadlineCause` / `WithTimeoutCause` | 1.21 | Attach a domain-specific error to deadline/timeout expiry (e.g. distinguish "DB query timed out" from "HTTP request timed out"). |
+| `errors.ErrUnsupported` | 1.21 | Standard sentinel for "not supported." Use instead of per-package custom sentinels. Check with `errors.Is`. |
+| `http.ResponseController` | 1.20 | Per-request flush, hijack, and deadline control without type-asserting `ResponseWriter` to `http.Flusher` or `http.Hijacker`. |
+| Enhanced `ServeMux` routing | 1.22 | `"GET /items/{id}"` patterns in `http.ServeMux`. Access with `r.PathValue("id")`. Wildcards: `{name}`, catch-all: `{path...}`, exact: `{$}`. Eliminates many third-party router dependencies. |
+| `os.Root` / `OpenRoot` | 1.24 | Confined directory access that prevents symlink escape. 1.25 adds `MkdirAll`, `ReadFile`, `WriteFile` for real use. |
+| `os.CopyFS` | 1.23 | Copy an entire `fs.FS` to local filesystem in one call. |
+| `os/signal.NotifyContext` with cause | 1.26 | Cancellation cause identifies which signal (SIGTERM vs SIGINT) triggered shutdown. |
+| `io/fs.SkipAll` / `filepath.SkipAll` | 1.20 | Return from `WalkDir` callback to stop walking entirely. Cleaner than a sentinel error. |
+| `GOMEMLIMIT` env / `debug.SetMemoryLimit` | 1.19 | Soft memory limit for GC. Use alongside or instead of `GOGC` in memory-constrained containers. |
+| `net/url.JoinPath` | 1.19 | Join URL path segments correctly. Replaces error-prone string concatenation. |
+| `go test -skip` | 1.20 | Skip tests matching a pattern. Useful when running a subset of a large test suite. |
+
+## Key packages
+
+### `slices` (1.21, iterators added 1.23)
+
+Replaces `sort.Slice`, manual search loops, and manual contains checks.
+
+Search: `Contains`, `ContainsFunc`, `Index`, `IndexFunc`,
+`BinarySearch`, `BinarySearchFunc`.
+
+Sort: `Sort`, `SortFunc`, `SortStableFunc`, `IsSorted`, `IsSortedFunc`,
+`Min`, `MinFunc`, `Max`, `MaxFunc`.
+
+Transform: `Clone`, `Compact`, `CompactFunc`, `Grow`, `Clip`,
+`Concat` (1.22), `Repeat` (1.23), `Reverse`, `Insert`, `Delete`,
+`Replace`.
+
+Compare: `Equal`, `EqualFunc`, `Compare`.
+
+Iterators (1.23): `All`, `Values`, `Backward`, `Collect`, `AppendSeq`,
+`Sorted`, `SortedFunc`, `SortedStableFunc`, `Chunk`.
+
+### `maps` (1.21, iterators added 1.23)
+
+Core: `Clone`, `Copy`, `Equal`, `EqualFunc`, `DeleteFunc`.
+
+Iterators (1.23): `All`, `Keys`, `Values`, `Insert`, `Collect`.
+
+### `cmp` (1.21, `Or` added 1.22)
+
+`Ordered` constraint for any ordered type. `Compare(a, b)` returns
+-1/0/+1. `Less(a, b)` returns bool. `Or(vals...)` returns first
+non-zero value.
+
+### `iter` (1.23)
+
+`Seq[V]` is `func(yield func(V) bool)`. `Seq2[K,V]` is
+`func(yield func(K, V) bool)`. Return these from your container's
+`.All()` methods. Consume with `for v := range seq` or pass to
+`slices.Collect`, `slices.Sorted`, `maps.Collect`, etc.
+
+### `math/rand/v2` (1.22)
+
+Replaces `math/rand`. `IntN` not `Intn`. Generic `N[T]()` for any
+integer type. Default source is `ChaCha8` (crypto-quality). No global
+`Seed`. Use `rand.New(source)` for reproducible sequences.
+
+### `log/slog` (1.21)
+
+`slog.Info`, `slog.Warn`, `slog.Error`, `slog.Debug` with key-value
+pairs. `slog.With(attrs...)` for logger with preset fields.
+`slog.GroupAttrs` (1.25) for clean group creation. Implement
+`slog.Handler` for custom backends.
+
+**Note:** This project uses `cdr.dev/slog/v3`, not `log/slog`. The
+API is different. Read existing code for usage patterns.
+
+## Pitfalls
+
+Things that are easy to get wrong, even when you know the modern API
+exists. Check your output against these.
+
+**Version misuse.** The replacement table has a "Since" column. If the
+project's `go.mod` says `go 1.22`, you cannot use `wg.Go` (1.25),
+`errors.AsType` (1.26), `new(expr)` (1.26), `b.Loop()` (1.24), or
+`testing/synctest` (1.24). Fall back to the older pattern. Always
+check before reaching for a replacement.
+
+**`slices.Sort` vs `slices.SortFunc`.** `slices.Sort` requires
+`cmp.Ordered` types (int, string, float64, etc.). For structs, custom
+types, or multi-field sorting, use `slices.SortFunc` with a comparator
+function. Using `slices.Sort` on a non-ordered type is a compile error.
+
+**`for range n` still binds the index.** `for range n` discards the
+index. If you need it, write `for i := range n`. Writing
+`for range n` and then trying to use `i` inside the loop is a compile
+error.
+
+**Don't hand-roll iterators when the stdlib returns one.** Functions
+like `maps.Keys`, `slices.Values`, `strings.SplitSeq`, and
+`strings.Lines` already return `iter.Seq` or `iter.Seq2`. Don't
+reimplement them. Compose with `slices.Collect`, `slices.Sorted`, etc.
+
+**Don't mix `math/rand` and `math/rand/v2`.** They have different
+function names (`Intn` vs `IntN`) and different default sources. Pick
+one per package. Prefer v2 for new code. The v1 global source is
+auto-seeded since 1.20, so delete `rand.Seed` calls either way.
+
+**Iterator protocol.** When implementing `iter.Seq`, you must respect
+the `yield` return value. If `yield` returns `false`, stop iteration
+immediately and return. Ignoring it violates the contract and causes
+panics when consumers break out of `for range` loops early.
+
+**`errors.Join` with nil.** `errors.Join` skips nil arguments. This is
+intentional and useful for aggregating optional errors, but don't
+assume the result is always non-nil. `errors.Join(nil, nil)` returns
+nil.
+
+**`cmp.Or` evaluates all arguments.** Unlike a chain of `if`
+statements, `cmp.Or(a(), b(), c())` calls all three functions. If any
+have side effects or are expensive, use `if`/`else` instead.
+
+**Timer channel semantics changed in 1.23.** Code that checks
+`len(timer.C)` to see if a value is pending no longer works (channel
+capacity is 0). Use a non-blocking `select` receive instead:
+`select { case <-timer.C: default: }`.
+
+**`context.WithoutCancel` still propagates values.** The derived
+context inherits all values from the parent. If any middleware stores
+request-scoped state (deadlines, trace IDs) via `context.WithValue`,
+the background work sees it. This is usually desired but can be
+surprising if the values hold references that should not outlive the
+request.
+
+## Behavioral changes that affect code
+
+- **Timers** (1.23): unstopped `Timer`/`Ticker` are GC'd immediately.
+  Channels are unbuffered: no stale values after `Reset`/`Stop`. You no
+  longer need `defer t.Stop()` to prevent leaks.
+- **Error tree traversal** (1.20): `errors.Is`/`As` follow
+  `Unwrap() []error`, not just `Unwrap() error`. Multi-error types must
+  expose the slice form for child errors to be found.
+- **`math/rand` auto-seeded** (1.20): the global RNG is auto-seeded.
+  `rand.Seed` is a no-op in 1.24+. Don't call it.
+- **GODEBUG compat** (1.21): behavioral changes are gated by `go.mod`'s
+  `go` line. Upgrading the version opts into new defaults.
+- **Build tags** (1.18): `//go:build` is the only syntax. `// +build`
+  is gone.
+- **Tool install** (1.18): `go get` no longer builds. Use
+  `go install pkg@version`.
+- **Doc comments** (1.19): support `[links]`, lists, and headings.
+- **`go test -skip`** (1.20): skip tests by name pattern from the
+  command line.
+- **`go fix ./...` modernizers** (1.26): auto-rewrites code to use
+  newer idioms. Run after Go version upgrades.
+
+## Transparent improvements (no code changes)
+
+Swiss Tables maps, Green Tea GC, PGO, faster `io.ReadAll`,
+stack-allocated slices, reduced cgo overhead, container-aware
+GOMAXPROCS. Free on upgrade.
@@ -4,22 +4,13 @@ This guide documents the PR description style used in the Coder repository, base

 ## PR Title Format

-Follow [Conventional Commits 1.0.0](https://www.conventionalcommits.org/en/v1.0.0/) format:
+Format: `type(scope): description`. See [CONTRIBUTING.md](docs/about/contributing/CONTRIBUTING.md#commit-messages) for full rules. PR titles are linted in CI.

-```text
-type(scope): brief description
-```
+- Types: `feat`, `fix`, `docs`, `style`, `refactor`, `perf`, `test`, `build`, `ci`, `chore`, `revert`
+- Scopes must be a real path (directory or file stem) containing all changed files
+- Omit scope if changes span multiple top-level directories

-**Common types:**
-
- `feat`: New features
- `fix`: Bug fixes
- `refactor`: Code refactoring without behavior change
- `perf`: Performance improvements
- `docs`: Documentation changes
- `chore`: Dependency updates, tooling changes
-
-**Examples:**
+Examples:

 - `feat: add tracing to aibridge`
 - `fix: move contexts to appropriate locations`
@@ -186,16 +177,6 @@ Dependabot PRs are auto-generated - don't try to match their verbose style for m
 Changes from https://github.com/upstream/repo/pull/XXX/
 ```

-## Attribution Footer
-
-For AI-generated PRs, end with:
-
-```markdown
-🤖 Generated with [Claude Code](https://claude.com/claude-code)
-
-Co-Authored-By: Claude Sonnet 4.5 <noreply@anthropic.com>
-```
-
 ## Creating PRs as Draft

 **IMPORTANT**: Unless explicitly told otherwise, always create PRs as drafts using the `--draft` flag:
@@ -206,11 +187,12 @@ gh pr create --draft --title "..." --body "..."

 After creating the PR, encourage the user to review it before marking as ready:

-```
+```text
 I've created draft PR #XXXX. Please review the changes and mark it as ready for review when you're satisfied.
 ```

 This allows the user to:
+
 - Review the code changes before requesting reviews from maintainers
 - Make additional adjustments if needed
 - Ensure CI passes before notifying reviewers
@@ -67,7 +67,6 @@ coderd/
 | `make test` | Run all Go tests |
 | `make test RUN=TestFunctionName` | Run specific test |
 | `go test -v ./path/to/package -run TestFunctionName` | Run test with verbose output |
-| `make test-postgres` | Run tests with Postgres database |
 | `make test-race` | Run tests with Go race detector |
 | `make test-e2e` | Run end-to-end tests |

@@ -109,7 +109,6 @@

 - Run full test suite: `make test`
 - Run specific test: `make test RUN=TestFunctionName`
- Run with Postgres: `make test-postgres`
 - Run with race detector: `make test-race`
 - Run end-to-end tests: `make test-e2e`

@@ -137,9 +136,11 @@ Then make your changes and push normally. Don't use `git push --force` unless th

 ## Commit Style

- Follow [Conventional Commits 1.0.0](https://www.conventionalcommits.org/en/v1.0.0/)
- Format: `type(scope): message`
- Types: `feat`, `fix`, `docs`, `style`, `refactor`, `test`, `chore`
+Format: `type(scope): message`. See [CONTRIBUTING.md](docs/about/contributing/CONTRIBUTING.md#commit-messages) for full rules. PR titles are linted in CI.
+
+- Types: `feat`, `fix`, `docs`, `style`, `refactor`, `perf`, `test`, `build`, `ci`, `chore`, `revert`
+- Scopes must be a real path (directory or file stem) containing all changed files
+- Omit scope if changes span multiple top-level directories
 - Keep message titles concise (~70 characters)
 - Use imperative, present tense in commit titles

@@ -1,7 +1,6 @@
 name: "🐞 Bug"
 description: "File a bug report."
 title: "bug: "
-labels: ["needs-triage"]
 type: "Bug"
 body:
  - type: checkboxes
@@ -0,0 +1,9 @@
+paths:
+  # The triage workflow uses a quoted heredoc (<<'EOF') with ${VAR}
+  # placeholders that envsubst expands later. Shellcheck's SC2016
+  # warns about unexpanded variables in single-quoted strings, but
+  # the non-expansion is intentional here. Actionlint doesn't honor
+  # inline shellcheck disable directives inside heredocs.
+  .github/workflows/triage-via-chat-api.yaml:
+    ignore:
+      - 'SC2016'
@@ -64,17 +64,14 @@ runs:
        TEST_PACKAGES: ${{ inputs.test-packages }}
        RACE_DETECTION: ${{ inputs.race-detection }}
        TS_DEBUG_DISCO: "true"
+        TS_DEBUG_DERP: "true"
        LC_CTYPE: "en_US.UTF-8"
        LC_ALL: "en_US.UTF-8"
      run: |
        set -euo pipefail

        if [[ ${RACE_DETECTION} == true ]]; then
-          gotestsum --junitfile="gotests.xml" --packages="${TEST_PACKAGES}" -- \
-            -tags=testsmallbatch \
-            -race \
-            -parallel "${TEST_NUM_PARALLEL_TESTS}" \
-            -p "${TEST_NUM_PARALLEL_PACKAGES}"
+          make test-race
        else
          make test
        fi
@@ -35,7 +35,7 @@ jobs:
      tailnet-integration: ${{ steps.filter.outputs.tailnet-integration }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -45,7 +45,7 @@ jobs:
          fetch-depth: 1
          persist-credentials: false
      - name: check changed files
-        uses: dorny/paths-filter@de90cc6fb38fc0963ad72b210f1f284cd68cea36 # v3.0.2
+        uses: dorny/paths-filter@fbd0ab8f3e69293af611ebaee6363fc25e6d187d # v4.0.1
        id: filter
        with:
          filters: |
@@ -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@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -191,7 +191,7 @@ jobs:

      # Check for any typos
      - name: Check for typos
-        uses: crate-ci/typos@2d0ce569feab1f8752f1dde43cc2f2aa53236e06 # v1.40.0
+        uses: crate-ci/typos@631208b7aac2daa8b707f55e7331f9112b0e062d # v1.44.0
        with:
          config: .github/workflows/typos.toml

@@ -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@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -272,7 +272,7 @@ jobs:
    if: ${{ !cancelled() }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -315,9 +315,7 @@ jobs:
          # Notifications require DB, we could start a DB instance here but
          # let's just restore for now.
          git checkout -- coderd/notifications/testdata/rendered-templates
-          # no `-j` flag as `make` fails with:
-          # coderd/rbac/object_gen.go:1:1: syntax error: package statement must be first
-          make --output-sync -B gen
+          make -j --output-sync -B gen

      - name: Check for unstaged files
        run: ./scripts/check_unstaged.sh
@@ -329,7 +327,7 @@ jobs:
    timeout-minutes: 20
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -368,9 +366,9 @@ jobs:
    needs: changes
    if: needs.changes.outputs.go == 'true' || needs.changes.outputs.ci == 'true' || github.ref == 'refs/heads/main'
    # This timeout must be greater than the timeout set by `go test` in
-    # `make test-postgres` to ensure we receive a trace of running
-    # goroutines. Setting this to the timeout +5m should work quite well
-    # even if some of the preceding steps are slow.
+    # `make test` to ensure we receive a trace of running goroutines.
+    # Setting this to the timeout +5m should work quite well even if
+    # some of the preceding steps are slow.
    timeout-minutes: 25
    strategy:
      fail-fast: false
@@ -381,7 +379,7 @@ jobs:
          - windows-2022
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -477,11 +475,6 @@ jobs:
          mkdir -p /tmp/tmpfs
          sudo mount_tmpfs -o noowners -s 8g /tmp/tmpfs

-          # Install google-chrome for scaletests.
-          # As another concern, should we really have this kind of external dependency
-          # requirement on standard CI?
-          brew install google-chrome
-
          # macOS will output "The default interactive shell is now zsh" intermittently in CI.
          touch ~/.bash_profile && echo "export BASH_SILENCE_DEPRECATION_WARNING=1" >> ~/.bash_profile

@@ -544,7 +537,7 @@ jobs:
          embedded-pg-cache: ${{ steps.embedded-pg-cache.outputs.embedded-pg-cache }}

      - name: Upload failed test db dumps
-        uses: actions/upload-artifact@b7c566a772e6b6bfb58ed0dc250532a479d7789f # v6.0.0
+        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
        with:
          name: failed-test-db-dump-${{matrix.os}}
          path: "**/*.test.sql"
@@ -576,13 +569,13 @@ jobs:
      - changes
    if: needs.changes.outputs.go == 'true' || needs.changes.outputs.ci == 'true' || github.ref == 'refs/heads/main'
    # This timeout must be greater than the timeout set by `go test` in
-    # `make test-postgres` to ensure we receive a trace of running
-    # goroutines. Setting this to the timeout +5m should work quite well
-    # even if some of the preceding steps are slow.
+    # `make test` to ensure we receive a trace of running goroutines.
+    # Setting this to the timeout +5m should work quite well even if
+    # some of the preceding steps are slow.
    timeout-minutes: 25
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -644,7 +637,7 @@ jobs:
    timeout-minutes: 25
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -716,7 +709,7 @@ jobs:
    timeout-minutes: 20
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -743,7 +736,7 @@ jobs:
    timeout-minutes: 20
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -776,7 +769,7 @@ jobs:
    name: ${{ matrix.variant.name }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -825,7 +818,7 @@ jobs:

      - name: Upload Playwright Failed Tests
        if: always() && github.actor != 'dependabot[bot]' && runner.os == 'Linux' && !github.event.pull_request.head.repo.fork
-        uses: actions/upload-artifact@b7c566a772e6b6bfb58ed0dc250532a479d7789f # v6.0.0
+        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
        with:
          name: failed-test-videos${{ matrix.variant.premium && '-premium' || '' }}
          path: ./site/test-results/**/*.webm
@@ -833,7 +826,7 @@ jobs:

      - name: Upload debug log
        if: always() && github.actor != 'dependabot[bot]' && runner.os == 'Linux' && !github.event.pull_request.head.repo.fork
-        uses: actions/upload-artifact@b7c566a772e6b6bfb58ed0dc250532a479d7789f # v6.0.0
+        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
        with:
          name: coderd-debug-logs${{ matrix.variant.premium && '-premium' || ''  }}
          path: ./site/e2e/test-results/debug.log
@@ -841,7 +834,7 @@ jobs:

      - name: Upload pprof dumps
        if: always() && github.actor != 'dependabot[bot]' && runner.os == 'Linux' && !github.event.pull_request.head.repo.fork
-        uses: actions/upload-artifact@b7c566a772e6b6bfb58ed0dc250532a479d7789f # v6.0.0
+        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
        with:
          name: debug-pprof-dumps${{ matrix.variant.premium && '-premium' || ''  }}
          path: ./site/test-results/**/debug-pprof-*.txt
@@ -856,7 +849,7 @@ jobs:
    if: needs.changes.outputs.site == 'true' || needs.changes.outputs.ci == 'true'
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -937,7 +930,7 @@ jobs:

    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -988,6 +981,9 @@ jobs:
        run: |
          make build/coder_docs_"$(./scripts/version.sh)".tgz

+      - name: Check for unstaged files
+        run: ./scripts/check_unstaged.sh
+
  required:
    runs-on: ubuntu-latest
    needs:
@@ -1009,7 +1005,7 @@ jobs:
    if: always()
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -1038,83 +1034,6 @@ jobs:

          echo "Required checks have passed"

-  # Builds the dylibs and upload it as an artifact so it can be embedded in the main build
-  build-dylib:
-    needs: changes
-    # We always build the dylibs on Go changes to verify we're not merging unbuildable code,
-    # but they need only be signed and uploaded on coder/coder main.
-    if: needs.changes.outputs.go == 'true' || needs.changes.outputs.ci == 'true' || github.ref == 'refs/heads/main' || startsWith(github.ref, 'refs/heads/release/')
-    runs-on: ${{ github.repository_owner == 'coder' && 'depot-macos-latest' || 'macos-latest' }}
-    steps:
-      # Harden Runner doesn't work on macOS
-      - name: Checkout
-        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
-        with:
-          fetch-depth: 0
-          persist-credentials: false
-
-      - name: Setup GNU tools (macOS)
-        uses: ./.github/actions/setup-gnu-tools
-
-      - name: Switch XCode Version
-        uses: maxim-lobanov/setup-xcode@60606e260d2fc5762a71e64e74b2174e8ea3c8bd # v1.6.0
-        with:
-          xcode-version: "16.1.0"
-
-      - name: Setup Go
-        uses: ./.github/actions/setup-go
-
-      - name: Install rcodesign
-        if: ${{ github.repository_owner == 'coder' && (github.ref == 'refs/heads/main' || startsWith(github.ref, 'refs/heads/release/')) }}
-        run: |
-          set -euo pipefail
-          wget -O /tmp/rcodesign.tar.gz https://github.com/indygreg/apple-platform-rs/releases/download/apple-codesign%2F0.22.0/apple-codesign-0.22.0-macos-universal.tar.gz
-          sudo tar -xzf /tmp/rcodesign.tar.gz \
-            -C /usr/local/bin \
-            --strip-components=1 \
-            apple-codesign-0.22.0-macos-universal/rcodesign
-          rm /tmp/rcodesign.tar.gz
-
-      - name: Setup Apple Developer certificate and API key
-        if: ${{ github.repository_owner == 'coder' && (github.ref == 'refs/heads/main' || startsWith(github.ref, 'refs/heads/release/')) }}
-        run: |
-          set -euo pipefail
-          touch /tmp/{apple_cert.p12,apple_cert_password.txt,apple_apikey.p8}
-          chmod 600 /tmp/{apple_cert.p12,apple_cert_password.txt,apple_apikey.p8}
-          echo "$AC_CERTIFICATE_P12_BASE64" | base64 -d > /tmp/apple_cert.p12
-          echo "$AC_CERTIFICATE_PASSWORD" > /tmp/apple_cert_password.txt
-          echo "$AC_APIKEY_P8_BASE64" | base64 -d > /tmp/apple_apikey.p8
-        env:
-          AC_CERTIFICATE_P12_BASE64: ${{ secrets.AC_CERTIFICATE_P12_BASE64 }}
-          AC_CERTIFICATE_PASSWORD: ${{ secrets.AC_CERTIFICATE_PASSWORD }}
-          AC_APIKEY_P8_BASE64: ${{ secrets.AC_APIKEY_P8_BASE64 }}
-
-      - name: Build dylibs
-        run: |
-          set -euxo pipefail
-          ./.github/scripts/retry.sh -- go mod download
-
-          make gen/mark-fresh
-          make build/coder-dylib
-        env:
-          CODER_SIGN_DARWIN: ${{ (github.ref == 'refs/heads/main' || startsWith(github.ref, 'refs/heads/release/')) && '1' || '0' }}
-          AC_CERTIFICATE_FILE: /tmp/apple_cert.p12
-          AC_CERTIFICATE_PASSWORD_FILE: /tmp/apple_cert_password.txt
-
-      - name: Upload build artifacts
-        if: ${{ github.repository_owner == 'coder' && (github.ref == 'refs/heads/main' || startsWith(github.ref, 'refs/heads/release/')) }}
-        uses: actions/upload-artifact@b7c566a772e6b6bfb58ed0dc250532a479d7789f # v6.0.0
-        with:
-          name: dylibs
-          path: |
-            ./build/*.h
-            ./build/*.dylib
-          retention-days: 7
-
-      - name: Delete Apple Developer certificate and API key
-        if: ${{ github.repository_owner == 'coder' && (github.ref == 'refs/heads/main' || startsWith(github.ref, 'refs/heads/release/')) }}
-        run: rm -f /tmp/{apple_cert.p12,apple_cert_password.txt,apple_apikey.p8}
-
  check-build:
    # This job runs make build to verify compilation on PRs.
    # The build doesn't get signed, and is not suitable for usage, unlike the
@@ -1124,7 +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@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -1161,7 +1080,6 @@ jobs:
    # to main branch.
    needs:
      - changes
-      - build-dylib
    if: (github.ref == 'refs/heads/main' || startsWith(github.ref, 'refs/heads/release/')) && needs.changes.outputs.docs-only == 'false' && !github.event.pull_request.head.repo.fork
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-22.04' }}
    permissions:
@@ -1179,7 +1097,7 @@ jobs:
      IMAGE: ghcr.io/coder/coder-preview:${{ steps.build-docker.outputs.tag }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -1190,7 +1108,7 @@ jobs:
          persist-credentials: false

      - name: GHCR Login
-        uses: docker/login-action@c94ce9fb468520275223c153574b00df6fe4bcc9 # v3.7.0
+        uses: docker/login-action@b45d80f862d83dbcd57f89517bcf500b2ab88fb2 # v4.0.0
        with:
          registry: ghcr.io
          username: ${{ github.actor }}
@@ -1201,6 +1119,8 @@ jobs:

      - name: Setup Go
        uses: ./.github/actions/setup-go
+        with:
+          use-cache: false

      - name: Install rcodesign
        run: |
@@ -1267,18 +1187,6 @@ jobs:
      - name: Setup GCloud SDK
        uses: google-github-actions/setup-gcloud@aa5489c8933f4cc7a4f7d45035b3b1440c9c10db # v3.0.1

-      - name: Download dylibs
-        uses: actions/download-artifact@37930b1c2abaa49bbe596cd826c3c89aef350131 # v7.0.0
-        with:
-          name: dylibs
-          path: ./build
-
-      - name: Insert dylibs
-        run: |
-          mv ./build/*amd64.dylib ./site/out/bin/coder-vpn-darwin-amd64.dylib
-          mv ./build/*arm64.dylib ./site/out/bin/coder-vpn-darwin-arm64.dylib
-          mv ./build/*arm64.h     ./site/out/bin/coder-vpn-darwin-dylib.h
-
      - name: Build
        run: |
          set -euxo pipefail
@@ -1292,11 +1200,10 @@ jobs:
          make -j \
            build/coder_linux_{amd64,arm64,armv7} \
            build/coder_"$version"_windows_amd64.zip \
-            build/coder_"$version"_linux_amd64.{tar.gz,deb}
+            build/coder_"$version"_linux_{amd64,arm64,armv7}.{tar.gz,deb}
        env:
-          # The Windows slim binary must be signed for Coder Desktop to accept
-          # it. The darwin executables don't need to be signed, but the dylibs
-          # do (see above).
+          # The Windows and Darwin slim binaries must be signed for Coder
+          # Desktop to accept them.
          CODER_SIGN_WINDOWS: "1"
          CODER_WINDOWS_RESOURCES: "1"
          CODER_SIGN_GPG: "1"
@@ -1310,12 +1217,35 @@ jobs:
          EV_CERTIFICATE_PATH: /tmp/ev_cert.pem
          GCLOUD_ACCESS_TOKEN: ${{ steps.gcloud_auth.outputs.access_token }}
          JSIGN_PATH: /tmp/jsign-6.0.jar
+          # Enable React profiling build and discoverable source maps
+          # for the dogfood deployment (dev.coder.com). This also
+          # applies to release/* branch builds, but those still
+          # produce coder-preview images, not release images.
+          # Release images are built by release.yaml (no profiling).
+          CODER_REACT_PROFILING: "true"
+
+      # Free up disk space before building Docker images. The preceding
+      # Build step produces ~2 GB of binaries and packages, the Go build
+      # cache is ~1.3 GB, and node_modules is ~500 MB. Docker image
+      # builds, pushes, and SBOM generation need headroom that isn't
+      # available without reclaiming some of that space.
+      - name: Clean up build cache
+        run: |
+          set -euxo pipefail
+          # Go caches are no longer needed — binaries are already compiled.
+          go clean -cache -modcache
+          # Remove .apk and .rpm packages that are not uploaded as
+          # artifacts and were only built as make prerequisites.
+          rm -f ./build/*.apk ./build/*.rpm

      - name: Build Linux Docker images
        id: build-docker
        env:
          CODER_IMAGE_BASE: ghcr.io/coder/coder-preview
          DOCKER_CLI_EXPERIMENTAL: "enabled"
+          # Skip building .deb/.rpm/.apk/.tar.gz as prerequisites for
+          # the Docker image targets — they were already built above.
+          DOCKER_IMAGE_NO_PREREQUISITES: "true"
        run: |
          set -euxo pipefail

@@ -1397,7 +1327,7 @@ jobs:
        id: attest_main
        if: github.ref == 'refs/heads/main'
        continue-on-error: true
-        uses: actions/attest@e59cbc1ad1ac2d59339667419eb8cdde6eb61e3d # v3.2.0
+        uses: actions/attest@59d89421af93a897026c735860bf21b6eb4f7b26 # v4.1.0
        with:
          subject-name: "ghcr.io/coder/coder-preview:main"
          predicate-type: "https://slsa.dev/provenance/v1"
@@ -1434,7 +1364,7 @@ jobs:
        id: attest_latest
        if: github.ref == 'refs/heads/main'
        continue-on-error: true
-        uses: actions/attest@e59cbc1ad1ac2d59339667419eb8cdde6eb61e3d # v3.2.0
+        uses: actions/attest@59d89421af93a897026c735860bf21b6eb4f7b26 # v4.1.0
        with:
          subject-name: "ghcr.io/coder/coder-preview:latest"
          predicate-type: "https://slsa.dev/provenance/v1"
@@ -1471,7 +1401,7 @@ jobs:
        id: attest_version
        if: github.ref == 'refs/heads/main'
        continue-on-error: true
-        uses: actions/attest@e59cbc1ad1ac2d59339667419eb8cdde6eb61e3d # v3.2.0
+        uses: actions/attest@59d89421af93a897026c735860bf21b6eb4f7b26 # v4.1.0
        with:
          subject-name: "ghcr.io/coder/coder-preview:${{ steps.build-docker.outputs.tag }}"
          predicate-type: "https://slsa.dev/provenance/v1"
@@ -1533,15 +1463,60 @@ jobs:
            ^v
          prune-untagged: true

-      - name: Upload build artifacts
+      - name: Upload build artifact (coder-linux-amd64.tar.gz)
        if: github.ref == 'refs/heads/main'
-        uses: actions/upload-artifact@b7c566a772e6b6bfb58ed0dc250532a479d7789f # v6.0.0
+        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
        with:
-          name: coder
-          path: |
-            ./build/*.zip
-            ./build/*.tar.gz
-            ./build/*.deb
+          name: coder-linux-amd64.tar.gz
+          path: ./build/*_linux_amd64.tar.gz
+          retention-days: 7
+
+      - name: Upload build artifact (coder-linux-amd64.deb)
+        if: github.ref == 'refs/heads/main'
+        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
+        with:
+          name: coder-linux-amd64.deb
+          path: ./build/*_linux_amd64.deb
+          retention-days: 7
+
+      - name: Upload build artifact (coder-linux-arm64.tar.gz)
+        if: github.ref == 'refs/heads/main'
+        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
+        with:
+          name: coder-linux-arm64.tar.gz
+          path: ./build/*_linux_arm64.tar.gz
+          retention-days: 7
+
+      - name: Upload build artifact (coder-linux-arm64.deb)
+        if: github.ref == 'refs/heads/main'
+        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
+        with:
+          name: coder-linux-arm64.deb
+          path: ./build/*_linux_arm64.deb
+          retention-days: 7
+
+      - name: Upload build artifact (coder-linux-armv7.tar.gz)
+        if: github.ref == 'refs/heads/main'
+        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
+        with:
+          name: coder-linux-armv7.tar.gz
+          path: ./build/*_linux_armv7.tar.gz
+          retention-days: 7
+
+      - name: Upload build artifact (coder-linux-armv7.deb)
+        if: github.ref == 'refs/heads/main'
+        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
+        with:
+          name: coder-linux-armv7.deb
+          path: ./build/*_linux_armv7.deb
+          retention-days: 7
+
+      - name: Upload build artifact (coder-windows-amd64.zip)
+        if: github.ref == 'refs/heads/main'
+        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
+        with:
+          name: coder-windows-amd64.zip
+          path: ./build/*_windows_amd64.zip
          retention-days: 7

  # Deploy is handled in deploy.yaml so we can apply concurrency limits.
@@ -1576,7 +1551,7 @@ 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@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -19,6 +19,9 @@ on:
        default: ""
        type: string

+permissions:
+  contents: read
+
 jobs:
  classify-severity:
    name: AI Severity Classification
@@ -32,7 +35,6 @@ jobs:
    permissions:
      contents: read
      issues: write
-      actions: write

    steps:
      - name: Determine Issue Context
@@ -31,6 +31,9 @@ on:
        default: ""
        type: string

+permissions:
+  contents: read
+
 jobs:
  code-review:
    name: AI Code Review
@@ -51,7 +54,6 @@ jobs:
    permissions:
      contents: read
      pull-requests: write
-      actions: write

    steps:
      - name: Check if secrets are available
@@ -23,6 +23,44 @@ permissions:
 concurrency: pr-${{ github.ref }}

 jobs:
+  community-label:
+    runs-on: ubuntu-latest
+    permissions:
+      pull-requests: write
+    if: >-
+      ${{
+        github.event_name == 'pull_request_target' &&
+        github.event.action == 'opened' &&
+        github.event.pull_request.author_association != 'MEMBER' &&
+        github.event.pull_request.author_association != 'COLLABORATOR' &&
+        github.event.pull_request.author_association != 'OWNER'
+      }}
+    steps:
+      - name: Add community label
+        uses: actions/github-script@ed597411d8f924073f98dfc5c65a23a2325f34cd # v8.0.0
+        with:
+          script: |
+            const params = {
+              issue_number: context.issue.number,
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+            }
+
+            const labels = context.payload.pull_request.labels.map((label) => label.name)
+            if (labels.includes("community")) {
+              console.log('PR already has "community" label.')
+              return
+            }
+
+            console.log(
+              'Adding "community" label for author association "%s".',
+              context.payload.pull_request.author_association,
+            )
+            await github.rest.issues.addLabels({
+              ...params,
+              labels: ["community"],
+            })
+
  cla:
    runs-on: ubuntu-latest
    permissions:
@@ -45,6 +83,109 @@ jobs:
          # Some users have signed a corporate CLA with Coder so are exempt from signing our community one.
          allowlist: "coryb,aaronlehmann,dependabot*,blink-so*,blinkagent*"

+  title:
+    runs-on: ubuntu-latest
+    if: ${{ github.event_name == 'pull_request_target' }}
+    steps:
+      - name: Validate PR title
+        uses: actions/github-script@ed597411d8f924073f98dfc5c65a23a2325f34cd # v8.0.0
+        with:
+          script: |
+            const { pull_request } = context.payload;
+            const title = pull_request.title;
+            const repo = { owner: context.repo.owner, repo: context.repo.repo };
+
+            const allowedTypes = [
+              "feat", "fix", "docs", "style", "refactor",
+              "perf", "test", "build", "ci", "chore", "revert",
+            ];
+            const expectedFormat = `"type(scope): description" or "type: description"`;
+            const guidelinesLink = `See: https://github.com/coder/coder/blob/main/docs/about/contributing/CONTRIBUTING.md#commit-messages`;
+            const scopeHint = (type) =>
+              `Use a broader scope or no scope (e.g., "${type}: ...") for cross-cutting changes.\n` +
+              guidelinesLink;
+
+            console.log("Title: %s", title);
+
+            // Parse conventional commit format: type(scope)!: description
+            const match = title.match(/^(\w+)(\(([^)]*)\))?(!)?\s*:\s*.+/);
+            if (!match) {
+              core.setFailed(
+                `PR title does not match conventional commit format.\n` +
+                `Expected: ${expectedFormat}\n` +
+                `Allowed types: ${allowedTypes.join(", ")}\n` +
+                guidelinesLink
+              );
+              return;
+            }
+
+            const type = match[1];
+            const scope = match[3]; // undefined if no parentheses
+
+            // Validate type.
+            if (!allowedTypes.includes(type)) {
+              core.setFailed(
+                `PR title has invalid type "${type}".\n` +
+                `Expected: ${expectedFormat}\n` +
+                `Allowed types: ${allowedTypes.join(", ")}\n` +
+                guidelinesLink
+              );
+              return;
+            }
+
+            // If no scope, we're done.
+            if (!scope) {
+              console.log("No scope provided, title is valid.");
+              return;
+            }
+
+            console.log("Scope: %s", scope);
+
+            // Fetch changed files.
+            const files = await github.paginate(github.rest.pulls.listFiles, {
+              ...repo,
+              pull_number: pull_request.number,
+              per_page: 100,
+            });
+            const changedPaths = files.map(f => f.filename);
+            console.log("Changed files: %d", changedPaths.length);
+
+            // Derive scope type from the changed files. The diff is the
+            // source of truth: if files exist under the scope, the path
+            // exists on the PR branch. No need for Contents API calls.
+            const isDir = changedPaths.some(f => f.startsWith(scope + "/"));
+            const isFile = changedPaths.some(f => f === scope);
+            const isStem = changedPaths.some(f => f.startsWith(scope + "."));
+
+            if (!isDir && !isFile && !isStem) {
+              core.setFailed(
+                `PR title scope "${scope}" does not match any files changed in this PR.\n` +
+                `Scopes must reference a path (directory or file stem) that contains changed files.\n` +
+                scopeHint(type)
+              );
+              return;
+            }
+
+            // Verify all changed files fall under the scope.
+            const outsideFiles = changedPaths.filter(f => {
+              if (isDir && f.startsWith(scope + "/")) return false;
+              if (f === scope) return false;
+              if (isStem && f.startsWith(scope + ".")) return false;
+              return true;
+            });
+
+            if (outsideFiles.length > 0) {
+              const listed = outsideFiles.map(f => "  - " + f).join("\n");
+              core.setFailed(
+                `PR title scope "${scope}" does not contain all changed files.\n` +
+                `Files outside scope:\n${listed}\n\n` +
+                scopeHint(type)
+              );
+              return;
+            }
+
+            console.log("PR title is valid.");
+
  release-labels:
    runs-on: ubuntu-latest
    permissions:
@@ -0,0 +1,23 @@
+# This workflow triggers a Vercel deploy hook which builds+deploys coder.com
+# (a Next.js app), to keep coder.com/docs URLs in sync with docs/manifest.json
+#
+# https://vercel.com/docs/deploy-hooks#triggering-a-deploy-hook
+
+name: Update coder.com/docs
+
+on:
+  push:
+    branches:
+      - main
+    paths:
+      - "docs/manifest.json"
+
+permissions: {}
+
+jobs:
+  deploy-docs:
+    runs-on: ubuntu-latest
+    steps:
+      - name: Deploy docs site
+        run: |
+          curl -X POST "${{ secrets.DEPLOY_DOCS_VERCEL_WEBHOOK }}"
@@ -36,7 +36,7 @@ jobs:
      verdict: ${{ steps.check.outputs.verdict }} # DEPLOY or NOOP
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -61,11 +61,11 @@ jobs:
    if: needs.should-deploy.outputs.verdict == 'DEPLOY'
    permissions:
      contents: read
-      id-token: write
+      id-token: write # to authenticate to EKS cluster
      packages: write # to retag image as dogfood
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -76,33 +76,29 @@ jobs:
          persist-credentials: false

      - name: GHCR Login
-        uses: docker/login-action@c94ce9fb468520275223c153574b00df6fe4bcc9 # v3.7.0
+        uses: docker/login-action@b45d80f862d83dbcd57f89517bcf500b2ab88fb2 # v4.0.0
        with:
          registry: ghcr.io
          username: ${{ github.actor }}
          password: ${{ secrets.GITHUB_TOKEN }}

-      - name: Authenticate to Google Cloud
-        uses: google-github-actions/auth@7c6bc770dae815cd3e89ee6cdf493a5fab2cc093 # v3.0.0
+      - name: Configure AWS Credentials
+        uses: aws-actions/configure-aws-credentials@8df5847569e6427dd6c4fb1cf565c83acfa8afa7 # v6.0.0
        with:
-          workload_identity_provider: ${{ vars.GCP_WORKLOAD_ID_PROVIDER }}
-          service_account: ${{ vars.GCP_SERVICE_ACCOUNT }}
+          role-to-assume: ${{ vars.AWS_DOGFOOD_DEPLOY_ROLE }}
+          aws-region: ${{ vars.AWS_DOGFOOD_DEPLOY_REGION }}

-      - name: Set up Google Cloud SDK
-        uses: google-github-actions/setup-gcloud@aa5489c8933f4cc7a4f7d45035b3b1440c9c10db # v3.0.1
+      - name: Get Cluster Credentials
+        run: aws eks update-kubeconfig --name "$AWS_DOGFOOD_CLUSTER_NAME" --region "$AWS_DOGFOOD_DEPLOY_REGION"
+        env:
+          AWS_DOGFOOD_CLUSTER_NAME: ${{ vars.AWS_DOGFOOD_CLUSTER_NAME }}
+          AWS_DOGFOOD_DEPLOY_REGION: ${{ vars.AWS_DOGFOOD_DEPLOY_REGION }}

      - name: Set up Flux CLI
        uses: fluxcd/flux2/action@8454b02a32e48d775b9f563cb51fdcb1787b5b93 # v2.7.5
        with:
          # Keep this and the github action up to date with the version of flux installed in dogfood cluster
-          version: "2.7.0"
-
-      - name: Get Cluster Credentials
-        uses: google-github-actions/get-gke-credentials@3da1e46a907576cefaa90c484278bb5b259dd395 # v3.0.0
-        with:
-          cluster_name: dogfood-v2
-          location: us-central1-a
-          project_id: coder-dogfood-v2
+          version: "2.8.2"

      # Retag image as dogfood while maintaining the multi-arch manifest
      - name: Tag image as dogfood
@@ -146,7 +142,7 @@ jobs:
    needs: deploy
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -34,6 +34,9 @@ on:
        default: ""
        type: string

+permissions:
+  contents: read
+
 jobs:
  doc-check:
    name: Analyze PR for Documentation Updates Needed
@@ -56,7 +59,6 @@ jobs:
    permissions:
      contents: read
      pull-requests: write
-      actions: write

    steps:
      - name: Check if secrets are available
@@ -38,7 +38,7 @@ jobs:
    if: github.repository_owner == 'coder'
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -48,7 +48,7 @@ jobs:
          persist-credentials: false

      - name: Docker login
-        uses: docker/login-action@c94ce9fb468520275223c153574b00df6fe4bcc9 # v3.7.0
+        uses: docker/login-action@b45d80f862d83dbcd57f89517bcf500b2ab88fb2 # v4.0.0
        with:
          registry: ghcr.io
          username: ${{ github.actor }}
@@ -30,7 +30,7 @@ jobs:
      - name: Setup Node
        uses: ./.github/actions/setup-node

-      - uses: tj-actions/changed-files@e0021407031f5be11a464abee9a0776171c79891 # v45.0.7
+      - uses: tj-actions/changed-files@22103cc46bda19c2b464ffe86db46df6922fd323 # v45.0.7
        id: changed-files
        with:
          files: |
@@ -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@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -78,11 +78,11 @@ jobs:
        uses: depot/setup-action@15c09a5f77a0840ad4bce955686522a257853461 # v1.7.1

      - name: Set up Docker Buildx
-        uses: docker/setup-buildx-action@8d2750c68a42422c14e847fe6c8ac0403b4cbd6f # v3.12.0
+        uses: docker/setup-buildx-action@4d04d5d9486b7bd6fa91e7baf45bbb4f8b9deedd # v4.0.0

      - name: Login to DockerHub
        if: github.ref == 'refs/heads/main'
-        uses: docker/login-action@c94ce9fb468520275223c153574b00df6fe4bcc9 # v3.7.0
+        uses: docker/login-action@b45d80f862d83dbcd57f89517bcf500b2ab88fb2 # v4.0.0
        with:
          username: ${{ secrets.DOCKERHUB_USERNAME }}
          password: ${{ secrets.DOCKERHUB_PASSWORD }}
@@ -125,7 +125,7 @@ jobs:
      id-token: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -0,0 +1,65 @@
+name: Linear Release
+
+on:
+  push:
+    branches:
+      - main
+  # This event reads the workflow from the default branch (main), not the
+  # release branch. No cherry-pick needed.
+  # https://docs.github.com/en/actions/using-workflows/events-that-trigger-workflows#release
+  release:
+    types: [published]
+
+permissions:
+  contents: read
+
+concurrency:
+  group: ${{ github.workflow }}-${{ github.ref }}
+  cancel-in-progress: true
+
+jobs:
+  sync:
+    name: Sync issues to Linear release
+    if: github.event_name == 'push'
+    runs-on: ubuntu-latest
+    steps:
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+        with:
+          fetch-depth: 0
+          persist-credentials: false
+
+      - name: Sync issues
+        id: sync
+        uses: linear/linear-release-action@5cbaabc187ceb63eee9d446e62e68e5c29a03ae8 # v0.5.0
+        with:
+          access_key: ${{ secrets.LINEAR_ACCESS_KEY }}
+          command: sync
+
+      - name: Print release URL
+        if: steps.sync.outputs.release-url
+        run: echo "Synced to $RELEASE_URL"
+        env:
+          RELEASE_URL: ${{ steps.sync.outputs.release-url }}
+
+  complete:
+    name: Complete Linear release
+    if: github.event_name == 'release'
+    runs-on: ubuntu-latest
+    steps:
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+        with:
+          persist-credentials: false
+
+      - name: Complete release
+        id: complete
+        uses: linear/linear-release-action@5cbaabc187ceb63eee9d446e62e68e5c29a03ae8 # v0
+        with:
+          access_key: ${{ secrets.LINEAR_ACCESS_KEY }}
+          command: complete
+          version: ${{ github.event.release.tag_name }}
+
+      - name: Print release URL
+        if: steps.complete.outputs.release-url
+        run: echo "Completed $RELEASE_URL"
+        env:
+          RELEASE_URL: ${{ steps.complete.outputs.release-url }}
@@ -16,9 +16,9 @@ jobs:
    # when changing runner sizes
    runs-on: ${{ matrix.os == 'macos-latest' && github.repository_owner == 'coder' && 'depot-macos-latest' || matrix.os == 'windows-2022' && github.repository_owner == 'coder' && 'depot-windows-2022-16' || matrix.os }}
    # This timeout must be greater than the timeout set by `go test` in
-    # `make test-postgres` to ensure we receive a trace of running
-    # goroutines. Setting this to the timeout +5m should work quite well
-    # even if some of the preceding steps are slow.
+    # `make test` to ensure we receive a trace of running goroutines.
+    # Setting this to the timeout +5m should work quite well even if
+    # some of the preceding steps are slow.
    timeout-minutes: 25
    strategy:
      fail-fast: false
@@ -28,7 +28,7 @@ jobs:
          - windows-2022
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -15,7 +15,7 @@ jobs:
    runs-on: ubuntu-latest
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -19,7 +19,7 @@ jobs:
      packages: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -39,7 +39,7 @@ jobs:
      PR_OPEN: ${{ steps.check_pr.outputs.pr_open }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -76,7 +76,7 @@ jobs:
    runs-on: "ubuntu-latest"
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -135,7 +135,7 @@ jobs:
          PR_NUMBER: ${{ steps.pr_info.outputs.PR_NUMBER }}

      - name: Check changed files
-        uses: dorny/paths-filter@de90cc6fb38fc0963ad72b210f1f284cd68cea36 # v3.0.2
+        uses: dorny/paths-filter@fbd0ab8f3e69293af611ebaee6363fc25e6d187d # v4.0.1
        id: filter
        with:
          base: ${{ github.ref }}
@@ -184,7 +184,7 @@ jobs:
      pull-requests: write # needed for commenting on PRs
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        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@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -248,7 +248,7 @@ jobs:
        uses: ./.github/actions/setup-sqlc

      - name: GHCR Login
-        uses: docker/login-action@c94ce9fb468520275223c153574b00df6fe4bcc9 # v3.7.0
+        uses: docker/login-action@b45d80f862d83dbcd57f89517bcf500b2ab88fb2 # v4.0.0
        with:
          registry: ghcr.io
          username: ${{ github.actor }}
@@ -288,7 +288,7 @@ jobs:
      PR_HOSTNAME: "pr${{ needs.get_info.outputs.PR_NUMBER }}.${{ secrets.PR_DEPLOYMENTS_DOMAIN }}"
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -14,12 +14,12 @@ jobs:

    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

      - name: Run Schmoder CI
-        uses: benc-uk/workflow-dispatch@e2e5e9a103e331dad343f381a29e654aea3cf8fc # v1.2.4
+        uses: benc-uk/workflow-dispatch@7a027648b88c2413826b6ddd6c76114894dc5ec4 # v1.3.1
        with:
          workflow: ci.yaml
          repo: coder/schmoder
@@ -58,87 +58,9 @@ jobs:

            if (!allowed) core.setFailed('Denied: requires maintain or admin');

-  # build-dylib is a separate job to build the dylib on macOS.
-  build-dylib:
-    runs-on: ${{ github.repository_owner == 'coder' && 'depot-macos-latest' || 'macos-latest' }}
-    needs: check-perms
-    steps:
-      # Harden Runner doesn't work on macOS.
-      - name: Checkout
-        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
-        with:
-          fetch-depth: 0
-          persist-credentials: false
-
-      # If the event that triggered the build was an annotated tag (which our
-      # tags are supposed to be), actions/checkout has a bug where the tag in
-      # question is only a lightweight tag and not a full annotated tag. This
-      # command seems to fix it.
-      # https://github.com/actions/checkout/issues/290
-      - name: Fetch git tags
-        run: git fetch --tags --force
-
-      - name: Setup GNU tools (macOS)
-        uses: ./.github/actions/setup-gnu-tools
-
-      - name: Switch XCode Version
-        uses: maxim-lobanov/setup-xcode@60606e260d2fc5762a71e64e74b2174e8ea3c8bd # v1.6.0
-        with:
-          xcode-version: "16.1.0"
-
-      - name: Setup Go
-        uses: ./.github/actions/setup-go
-
-      - name: Install rcodesign
-        run: |
-          set -euo pipefail
-          wget -O /tmp/rcodesign.tar.gz https://github.com/indygreg/apple-platform-rs/releases/download/apple-codesign%2F0.22.0/apple-codesign-0.22.0-macos-universal.tar.gz
-          sudo tar -xzf /tmp/rcodesign.tar.gz \
-            -C /usr/local/bin \
-            --strip-components=1 \
-            apple-codesign-0.22.0-macos-universal/rcodesign
-          rm /tmp/rcodesign.tar.gz
-
-      - name: Setup Apple Developer certificate and API key
-        run: |
-          set -euo pipefail
-          touch /tmp/{apple_cert.p12,apple_cert_password.txt,apple_apikey.p8}
-          chmod 600 /tmp/{apple_cert.p12,apple_cert_password.txt,apple_apikey.p8}
-          echo "$AC_CERTIFICATE_P12_BASE64" | base64 -d > /tmp/apple_cert.p12
-          echo "$AC_CERTIFICATE_PASSWORD" > /tmp/apple_cert_password.txt
-          echo "$AC_APIKEY_P8_BASE64" | base64 -d > /tmp/apple_apikey.p8
-        env:
-          AC_CERTIFICATE_P12_BASE64: ${{ secrets.AC_CERTIFICATE_P12_BASE64 }}
-          AC_CERTIFICATE_PASSWORD: ${{ secrets.AC_CERTIFICATE_PASSWORD }}
-          AC_APIKEY_P8_BASE64: ${{ secrets.AC_APIKEY_P8_BASE64 }}
-
-      - name: Build dylibs
-        run: |
-          set -euxo pipefail
-          ./.github/scripts/retry.sh -- go mod download
-
-          make gen/mark-fresh
-          make build/coder-dylib
-        env:
-          CODER_SIGN_DARWIN: 1
-          AC_CERTIFICATE_FILE: /tmp/apple_cert.p12
-          AC_CERTIFICATE_PASSWORD_FILE: /tmp/apple_cert_password.txt
-
-      - name: Upload build artifacts
-        uses: actions/upload-artifact@b7c566a772e6b6bfb58ed0dc250532a479d7789f # v6.0.0
-        with:
-          name: dylibs
-          path: |
-            ./build/*.h
-            ./build/*.dylib
-          retention-days: 7
-
-      - name: Delete Apple Developer certificate and API key
-        run: rm -f /tmp/{apple_cert.p12,apple_cert_password.txt,apple_apikey.p8}
-
  release:
    name: Build and publish
-    needs: [build-dylib, check-perms]
+    needs: [check-perms]
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
    permissions:
      # Required to publish a release
@@ -158,7 +80,7 @@ jobs:
      version: ${{ steps.version.outputs.version }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -233,7 +155,7 @@ jobs:
          cat "$CODER_RELEASE_NOTES_FILE"

      - name: Docker Login
-        uses: docker/login-action@c94ce9fb468520275223c153574b00df6fe4bcc9 # v3.7.0
+        uses: docker/login-action@b45d80f862d83dbcd57f89517bcf500b2ab88fb2 # v4.0.0
        with:
          registry: ghcr.io
          username: ${{ github.actor }}
@@ -241,6 +163,8 @@ jobs:

      - name: Setup Go
        uses: ./.github/actions/setup-go
+        with:
+          use-cache: false

      - name: Setup Node
        uses: ./.github/actions/setup-node
@@ -320,18 +244,6 @@ jobs:
      - name: Setup GCloud SDK
        uses: google-github-actions/setup-gcloud@aa5489c8933f4cc7a4f7d45035b3b1440c9c10db # v3.0.1

-      - name: Download dylibs
-        uses: actions/download-artifact@37930b1c2abaa49bbe596cd826c3c89aef350131 # v7.0.0
-        with:
-          name: dylibs
-          path: ./build
-
-      - name: Insert dylibs
-        run: |
-          mv ./build/*amd64.dylib ./site/out/bin/coder-vpn-darwin-amd64.dylib
-          mv ./build/*arm64.dylib ./site/out/bin/coder-vpn-darwin-arm64.dylib
-          mv ./build/*arm64.h     ./site/out/bin/coder-vpn-darwin-dylib.h
-
      - name: Build binaries
        run: |
          set -euo pipefail
@@ -448,7 +360,7 @@ jobs:
        id: attest_base
        if: ${{ !inputs.dry_run && steps.image-base-tag.outputs.tag != '' }}
        continue-on-error: true
-        uses: actions/attest@e59cbc1ad1ac2d59339667419eb8cdde6eb61e3d # v3.2.0
+        uses: actions/attest@59d89421af93a897026c735860bf21b6eb4f7b26 # v4.1.0
        with:
          subject-name: ${{ steps.image-base-tag.outputs.tag }}
          predicate-type: "https://slsa.dev/provenance/v1"
@@ -564,7 +476,7 @@ jobs:
        id: attest_main
        if: ${{ !inputs.dry_run }}
        continue-on-error: true
-        uses: actions/attest@e59cbc1ad1ac2d59339667419eb8cdde6eb61e3d # v3.2.0
+        uses: actions/attest@59d89421af93a897026c735860bf21b6eb4f7b26 # v4.1.0
        with:
          subject-name: ${{ steps.build_docker.outputs.multiarch_image }}
          predicate-type: "https://slsa.dev/provenance/v1"
@@ -608,7 +520,7 @@ jobs:
        id: attest_latest
        if: ${{ !inputs.dry_run && steps.build_docker.outputs.created_latest_tag == 'true' }}
        continue-on-error: true
-        uses: actions/attest@e59cbc1ad1ac2d59339667419eb8cdde6eb61e3d # v3.2.0
+        uses: actions/attest@59d89421af93a897026c735860bf21b6eb4f7b26 # v4.1.0
        with:
          subject-name: ${{ steps.latest_tag.outputs.tag }}
          predicate-type: "https://slsa.dev/provenance/v1"
@@ -755,7 +667,7 @@ jobs:

      - name: Upload artifacts to actions (if dry-run)
        if: ${{ inputs.dry_run }}
-        uses: actions/upload-artifact@b7c566a772e6b6bfb58ed0dc250532a479d7789f # v6.0.0
+        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
        with:
          name: release-artifacts
          path: |
@@ -771,7 +683,7 @@ jobs:

      - name: Upload latest sbom artifact to actions (if dry-run)
        if: inputs.dry_run && steps.build_docker.outputs.created_latest_tag == 'true'
-        uses: actions/upload-artifact@b7c566a772e6b6bfb58ed0dc250532a479d7789f # v6.0.0
+        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
        with:
          name: latest-sbom-artifact
          path: ./coder_latest_sbom.spdx.json
@@ -790,13 +702,11 @@ jobs:
    name: Publish to Homebrew tap
    runs-on: ubuntu-latest
    needs: release
-    if: ${{ !inputs.dry_run }}
+    if: ${{ !inputs.dry_run && inputs.release_channel == 'mainline' }}

    steps:
-      # TODO: skip this if it's not a new release (i.e. a backport). This is
-      #       fine right now because it just makes a PR that we can close.
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -872,7 +782,7 @@ jobs:

    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -955,35 +865,3 @@ jobs:
          # different repo.
          GH_TOKEN: ${{ secrets.CDRCI_GITHUB_TOKEN }}
          VERSION: ${{ needs.release.outputs.version }}
-
-  # publish-sqlc pushes the latest schema to sqlc cloud.
-  # At present these pushes cannot be tagged, so the last push is always the latest.
-  publish-sqlc:
-    name: "Publish to schema sqlc cloud"
-    runs-on: "ubuntu-latest"
-    needs: release
-    if: ${{ !inputs.dry_run }}
-    steps:
-      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
-        with:
-          egress-policy: audit
-
-      - name: Checkout
-        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
-        with:
-          fetch-depth: 1
-          persist-credentials: false
-
-      # We need golang to run the migration main.go
-      - name: Setup Go
-        uses: ./.github/actions/setup-go
-
-      - name: Setup sqlc
-        uses: ./.github/actions/setup-sqlc
-
-      - name: Push schema to sqlc cloud
-        # Don't block a release on this
-        continue-on-error: true
-        run: |
-          make sqlc-push
@@ -20,7 +20,7 @@ jobs:

    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -39,7 +39,7 @@ jobs:

      # Upload the results as artifacts.
      - name: "Upload artifact"
-        uses: actions/upload-artifact@b7c566a772e6b6bfb58ed0dc250532a479d7789f # v6.0.0
+        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
        with:
          name: SARIF file
          path: results.sarif
@@ -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@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -63,116 +63,3 @@ jobs:
            --data "{\"content\": \"$msg\"}" \
            "${{ secrets.SLACK_SECURITY_FAILURE_WEBHOOK_URL }}"

-  trivy:
-    permissions:
-      security-events: write
-    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
-    steps:
-      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
-        with:
-          egress-policy: audit
-
-      - name: Checkout
-        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
-        with:
-          fetch-depth: 0
-          persist-credentials: false
-
-      - name: Setup Go
-        uses: ./.github/actions/setup-go
-
-      - name: Setup Node
-        uses: ./.github/actions/setup-node
-
-      - name: Setup sqlc
-        uses: ./.github/actions/setup-sqlc
-
-      - name: Install cosign
-        uses: ./.github/actions/install-cosign
-
-      - name: Install syft
-        uses: ./.github/actions/install-syft
-
-      - name: Install yq
-        run: go run github.com/mikefarah/yq/v4@v4.44.3
-      - name: Install mockgen
-        run: ./.github/scripts/retry.sh -- go install go.uber.org/mock/mockgen@v0.6.0
-      - name: Install protoc-gen-go
-        run: ./.github/scripts/retry.sh -- go install google.golang.org/protobuf/cmd/protoc-gen-go@v1.30
-      - name: Install protoc-gen-go-drpc
-        run: ./.github/scripts/retry.sh -- go install storj.io/drpc/cmd/protoc-gen-go-drpc@v0.0.34
-      - name: Install Protoc
-        run: |
-          # protoc must be in lockstep with our dogfood Dockerfile or the
-          # version in the comments will differ. This is also defined in
-          # ci.yaml.
-          set -euxo pipefail
-          cd dogfood/coder
-          mkdir -p /usr/local/bin
-          mkdir -p /usr/local/include
-
-          DOCKER_BUILDKIT=1 docker build . --target proto -t protoc
-          protoc_path=/usr/local/bin/protoc
-          docker run --rm --entrypoint cat protoc /tmp/bin/protoc > $protoc_path
-          chmod +x $protoc_path
-          protoc --version
-          # Copy the generated files to the include directory.
-          docker run --rm -v /usr/local/include:/target protoc cp -r /tmp/include/google /target/
-          ls -la /usr/local/include/google/protobuf/
-          stat /usr/local/include/google/protobuf/timestamp.proto
-
-      - name: Build Coder linux amd64 Docker image
-        id: build
-        run: |
-          set -euo pipefail
-
-          version="$(./scripts/version.sh)"
-          image_job="build/coder_${version}_linux_amd64.tag"
-
-          # This environment variable force make to not build packages and
-          # archives (which the Docker image depends on due to technical reasons
-          # related to concurrent FS writes).
-          export DOCKER_IMAGE_NO_PREREQUISITES=true
-          # This environment variables forces scripts/build_docker.sh to build
-          # the base image tag locally instead of using the cached version from
-          # the registry.
-          CODER_IMAGE_BUILD_BASE_TAG="$(CODER_IMAGE_BASE=coder-base ./scripts/image_tag.sh --version "$version")"
-          export CODER_IMAGE_BUILD_BASE_TAG
-
-          # We would like to use make -j here, but it doesn't work with the some recent additions
-          # to our code generation.
-          make "$image_job"
-          echo "image=$(cat "$image_job")" >> "$GITHUB_OUTPUT"
-
-      - name: Run Trivy vulnerability scanner
-        uses: aquasecurity/trivy-action@c1824fd6edce30d7ab345a9989de00bbd46ef284 # v0.34.0
-        with:
-          image-ref: ${{ steps.build.outputs.image }}
-          format: sarif
-          output: trivy-results.sarif
-          severity: "CRITICAL,HIGH"
-
-      - name: Upload Trivy scan results to GitHub Security tab
-        uses: github/codeql-action/upload-sarif@5d4e8d1aca955e8d8589aabd499c5cae939e33c7 # v3.29.5
-        with:
-          sarif_file: trivy-results.sarif
-          category: "Trivy"
-
-      - name: Upload Trivy scan results as an artifact
-        uses: actions/upload-artifact@b7c566a772e6b6bfb58ed0dc250532a479d7789f # v6.0.0
-        with:
-          name: trivy
-          path: trivy-results.sarif
-          retention-days: 7
-
-      - name: Send Slack notification on failure
-        if: ${{ failure() }}
-        run: |
-          msg="❌ Trivy Failed\n\nhttps://github.com/${{ github.repository }}/actions/runs/${{ github.run_id }}"
-          curl \
-            -qfsSL \
-            -X POST \
-            -H "Content-Type: application/json" \
-            --data "{\"content\": \"$msg\"}" \
-            "${{ secrets.SLACK_SECURITY_FAILURE_WEBHOOK_URL }}"
@@ -18,7 +18,7 @@ jobs:
      pull-requests: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -96,7 +96,7 @@ jobs:
      contents: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -120,7 +120,7 @@ jobs:
      actions: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -26,6 +26,9 @@ on:
        default: "traiage"
        type: string

+permissions:
+  contents: read
+
 jobs:
  traiage:
    name: Triage GitHub Issue with Claude Code
@@ -38,7 +41,6 @@ jobs:
    permissions:
      contents: read
      issues: write
-      actions: write

    steps:
      # This is only required for testing locally using nektos/act, so leaving commented out.
@@ -0,0 +1,295 @@
+# This workflow reimplements the AI Triage Automation using the Coder Chat API
+# instead of the Tasks API. The Chat API (/api/experimental/chats) is a simpler
+# interface that does not require a dedicated GitHub Action or workspace
+# provisioning — we just create a chat, poll for completion, and link the
+# result on the issue. All API calls use curl + jq directly.
+#
+# Key differences from the Tasks API workflow (traiage.yaml):
+#   - No checkout of coder/create-task-action; everything is inline curl/jq.
+#   - No template_name / template_preset / prefix inputs — the Chat API handles
+#     resource allocation internally.
+#   - Uses POST /api/experimental/chats to create a chat session.
+#   - Polls GET /api/experimental/chats/<id> until the agent finishes.
+#   - Chat URL format: ${CODER_URL}/agents?chat=${CHAT_ID}
+
+name: AI Triage via Chat API
+
+on:
+  issues:
+    types:
+      - labeled
+  workflow_dispatch:
+    inputs:
+      issue_url:
+        description: "GitHub Issue URL to process"
+        required: true
+        type: string
+
+permissions:
+  contents: read
+
+jobs:
+  triage-chat:
+    name: Triage GitHub Issue via Chat API
+    runs-on: ubuntu-latest
+    if: github.event.label.name == 'chat-triage' || github.event_name == 'workflow_dispatch'
+    timeout-minutes: 30
+    env:
+      CODER_URL: ${{ secrets.TRAIAGE_CODER_URL }}
+      CODER_SESSION_TOKEN: ${{ secrets.TRAIAGE_CODER_SESSION_TOKEN }}
+    permissions:
+      contents: read
+      issues: write
+
+    steps:
+      # ------------------------------------------------------------------
+      # Step 1: Determine the GitHub user and issue URL.
+      # Identical to the Tasks API workflow — resolve the actor for
+      # workflow_dispatch or the issue sender for label events.
+      # ------------------------------------------------------------------
+      - name: Determine Inputs
+        id: determine-inputs
+        if: always()
+        env:
+          GITHUB_ACTOR: ${{ github.actor }}
+          GITHUB_EVENT_ISSUE_HTML_URL: ${{ github.event.issue.html_url }}
+          GITHUB_EVENT_NAME: ${{ github.event_name }}
+          GITHUB_EVENT_USER_ID: ${{ github.event.sender.id }}
+          GITHUB_EVENT_USER_LOGIN: ${{ github.event.sender.login }}
+          INPUTS_ISSUE_URL: ${{ inputs.issue_url }}
+          GH_TOKEN: ${{ github.token }}
+        run: |
+          set -euo pipefail
+
+          # For workflow_dispatch, use the actor who triggered it.
+          # For issues events, use the issue sender.
+          if [[ "${GITHUB_EVENT_NAME}" == "workflow_dispatch" ]]; then
+            if ! GITHUB_USER_ID=$(gh api "users/${GITHUB_ACTOR}" --jq '.id'); then
+              echo "::error::Failed to get GitHub user ID for actor ${GITHUB_ACTOR}"
+              exit 1
+            fi
+            echo "Using workflow_dispatch actor: ${GITHUB_ACTOR} (ID: ${GITHUB_USER_ID})"
+            echo "github_user_id=${GITHUB_USER_ID}" >> "${GITHUB_OUTPUT}"
+            echo "github_username=${GITHUB_ACTOR}" >> "${GITHUB_OUTPUT}"
+
+            echo "Using issue URL: ${INPUTS_ISSUE_URL}"
+            echo "issue_url=${INPUTS_ISSUE_URL}" >> "${GITHUB_OUTPUT}"
+
+            exit 0
+          elif [[ "${GITHUB_EVENT_NAME}" == "issues" ]]; then
+            GITHUB_USER_ID=${GITHUB_EVENT_USER_ID}
+            echo "Using issue author: ${GITHUB_EVENT_USER_LOGIN} (ID: ${GITHUB_USER_ID})"
+            echo "github_user_id=${GITHUB_USER_ID}" >> "${GITHUB_OUTPUT}"
+            echo "github_username=${GITHUB_EVENT_USER_LOGIN}" >> "${GITHUB_OUTPUT}"
+
+            echo "Using issue URL: ${GITHUB_EVENT_ISSUE_HTML_URL}"
+            echo "issue_url=${GITHUB_EVENT_ISSUE_HTML_URL}" >> "${GITHUB_OUTPUT}"
+
+            exit 0
+          else
+            echo "::error::Unsupported event type: ${GITHUB_EVENT_NAME}"
+            exit 1
+          fi
+
+      # ------------------------------------------------------------------
+      # Step 2: Verify the triggering user has push access.
+      # Unchanged from the Tasks API workflow.
+      # ------------------------------------------------------------------
+      - name: Verify push access
+        env:
+          GITHUB_REPOSITORY: ${{ github.repository }}
+          GH_TOKEN: ${{ github.token }}
+          GITHUB_USERNAME: ${{ steps.determine-inputs.outputs.github_username }}
+          GITHUB_USER_ID: ${{ steps.determine-inputs.outputs.github_user_id }}
+        run: |
+          set -euo pipefail
+
+          can_push="$(gh api "/repos/${GITHUB_REPOSITORY}/collaborators/${GITHUB_USERNAME}/permission" --jq '.user.permissions.push')"
+          if [[ "${can_push}" != "true" ]]; then
+            echo "::error title=Access Denied::${GITHUB_USERNAME} does not have push access to ${GITHUB_REPOSITORY}"
+            exit 1
+          fi
+
+      # ------------------------------------------------------------------
+      # Step 3: Create a chat via the Coder Chat API.
+      # Unlike the Tasks API which provisions a full workspace, the Chat
+      # API creates a lightweight chat session. We POST to
+      # /api/experimental/chats with the triage prompt as the initial
+      # message and receive a chat ID back.
+      # ------------------------------------------------------------------
+      - name: Create chat via Coder Chat API
+        id: create-chat
+        env:
+          ISSUE_URL: ${{ steps.determine-inputs.outputs.issue_url }}
+          GH_TOKEN: ${{ github.token }}
+        run: |
+          set -euo pipefail
+
+          # Build the same triage prompt used by the Tasks API workflow.
+          TASK_PROMPT=$(cat <<'EOF'
+          Fix ${ISSUE_URL}
+
+            1. Use the gh CLI to read the issue description and comments.
+            2. Think carefully and try to understand the root cause. If the issue is unclear or not well defined, ask me to clarify and provide more information.
+            3. Write a proposed implementation plan to PLAN.md for me to review before starting implementation. Your plan should use TDD and only make the minimal changes necessary to fix the root cause.
+            4. When I approve your plan, start working on it. If you encounter issues with the plan, ask me for clarification and update the plan as required.
+            5. When you have finished implementation according to the plan, commit and push your changes, and create a PR using the gh CLI for me to review.
+          EOF
+          )
+          # Perform variable substitution on the prompt — scoped to $ISSUE_URL only.
+          # Using envsubst without arguments would expand every env var in scope
+          # (including CODER_SESSION_TOKEN), so we name the variable explicitly.
+          TASK_PROMPT=$(echo "${TASK_PROMPT}" | envsubst '$ISSUE_URL')
+
+          echo "Creating chat with prompt:"
+          echo "${TASK_PROMPT}"
+
+          # POST to the Chat API to create a new chat session.
+          RESPONSE=$(curl --silent --fail-with-body \
+            -X POST \
+            -H "Coder-Session-Token: ${CODER_SESSION_TOKEN}" \
+            -H "Content-Type: application/json" \
+            -d "$(jq -n --arg prompt "${TASK_PROMPT}" \
+              '{content: [{type: "text", text: $prompt}]}')" \
+            "${CODER_URL}/api/experimental/chats")
+
+          echo "Chat API response:"
+          echo "${RESPONSE}" | jq .
+
+          CHAT_ID=$(echo "${RESPONSE}" | jq -r '.id')
+          CHAT_STATUS=$(echo "${RESPONSE}" | jq -r '.status')
+
+          if [[ -z "${CHAT_ID}" || "${CHAT_ID}" == "null" ]]; then
+            echo "::error::Failed to create chat — no ID returned"
+            echo "Response: ${RESPONSE}"
+            exit 1
+          fi
+
+          # Validate that CHAT_ID is a UUID before using it in URL paths.
+          # This guards against unexpected API responses being interpolated
+          # into subsequent curl calls.
+          if [[ ! "${CHAT_ID}" =~ ^[0-9a-f]{8}-[0-9a-f]{4}-[0-9a-f]{4}-[0-9a-f]{4}-[0-9a-f]{12}$ ]]; then
+            echo "::error::CHAT_ID is not a valid UUID: ${CHAT_ID}"
+            exit 1
+          fi
+
+          CHAT_URL="${CODER_URL}/agents?chat=${CHAT_ID}"
+
+          echo "Chat created: ${CHAT_ID} (status: ${CHAT_STATUS})"
+          echo "Chat URL: ${CHAT_URL}"
+
+          echo "chat_id=${CHAT_ID}" >> "${GITHUB_OUTPUT}"
+          echo "chat_url=${CHAT_URL}" >> "${GITHUB_OUTPUT}"
+
+      # ------------------------------------------------------------------
+      # Step 4: Poll the chat status until the agent finishes.
+      # The Chat API is asynchronous — after creation the agent begins
+      # working in the background. We poll GET /api/experimental/chats/<id>
+      # every 5 seconds until the status is "waiting" (agent needs input),
+      # "completed" (agent finished), or "error". Timeout after 10 minutes.
+      # ------------------------------------------------------------------
+      - name: Poll chat status
+        id: poll-status
+        env:
+          CHAT_ID: ${{ steps.create-chat.outputs.chat_id }}
+        run: |
+          set -euo pipefail
+
+          POLL_INTERVAL=5
+          # 10 minutes = 600 seconds.
+          TIMEOUT=600
+          ELAPSED=0
+
+          echo "Polling chat ${CHAT_ID} every ${POLL_INTERVAL}s (timeout: ${TIMEOUT}s)..."
+
+          while true; do
+            RESPONSE=$(curl --silent --fail-with-body \
+              -H "Coder-Session-Token: ${CODER_SESSION_TOKEN}" \
+              "${CODER_URL}/api/experimental/chats/${CHAT_ID}")
+
+            STATUS=$(echo "${RESPONSE}" | jq -r '.status')
+
+            echo "[${ELAPSED}s] Chat status: ${STATUS}"
+
+            case "${STATUS}" in
+              waiting|completed)
+                echo "Chat reached terminal status: ${STATUS}"
+                echo "final_status=${STATUS}" >> "${GITHUB_OUTPUT}"
+                exit 0
+                ;;
+              error)
+                echo "::error::Chat entered error state"
+                echo "${RESPONSE}" | jq .
+                echo "final_status=error" >> "${GITHUB_OUTPUT}"
+                exit 1
+                ;;
+              pending|running)
+                # Still working — keep polling.
+                ;;
+              *)
+                echo "::warning::Unknown chat status: ${STATUS}"
+                ;;
+            esac
+
+            if [[ ${ELAPSED} -ge ${TIMEOUT} ]]; then
+              echo "::error::Timed out after ${TIMEOUT}s waiting for chat to finish"
+              echo "final_status=timeout" >> "${GITHUB_OUTPUT}"
+              exit 1
+            fi
+
+            sleep "${POLL_INTERVAL}"
+            ELAPSED=$((ELAPSED + POLL_INTERVAL))
+          done
+
+      # ------------------------------------------------------------------
+      # Step 5: Comment on the GitHub issue with a link to the chat.
+      # Only comment if the issue belongs to this repository (same guard
+      # as the Tasks API workflow).
+      # ------------------------------------------------------------------
+      - name: Comment on issue
+        if: startsWith(steps.determine-inputs.outputs.issue_url, format('{0}/{1}', github.server_url, github.repository))
+        env:
+          ISSUE_URL: ${{ steps.determine-inputs.outputs.issue_url }}
+          CHAT_URL: ${{ steps.create-chat.outputs.chat_url }}
+          CHAT_ID: ${{ steps.create-chat.outputs.chat_id }}
+          FINAL_STATUS: ${{ steps.poll-status.outputs.final_status }}
+          GH_TOKEN: ${{ github.token }}
+        run: |
+          set -euo pipefail
+
+          COMMENT_BODY=$(cat <<EOF
+          🤖 **AI Triage Chat Created**
+
+          A Coder chat session has been created to investigate this issue.
+
+          **Chat URL:** ${CHAT_URL}
+          **Chat ID:** \`${CHAT_ID}\`
+          **Status:** ${FINAL_STATUS}
+
+          The agent is working on a triage plan. Visit the chat to follow progress or provide guidance.
+          EOF
+          )
+
+          gh issue comment "${ISSUE_URL}" --body "${COMMENT_BODY}"
+          echo "Comment posted on ${ISSUE_URL}"
+
+      # ------------------------------------------------------------------
+      # Step 6: Write a summary to the GitHub Actions step summary.
+      # ------------------------------------------------------------------
+      - name: Write summary
+        env:
+          CHAT_ID: ${{ steps.create-chat.outputs.chat_id }}
+          CHAT_URL: ${{ steps.create-chat.outputs.chat_url }}
+          FINAL_STATUS: ${{ steps.poll-status.outputs.final_status }}
+          ISSUE_URL: ${{ steps.determine-inputs.outputs.issue_url }}
+        run: |
+          set -euo pipefail
+
+          {
+            echo "## AI Triage via Chat API"
+            echo ""
+            echo "**Issue:**      ${ISSUE_URL}"
+            echo "**Chat ID:**    \`${CHAT_ID}\`"
+            echo "**Chat URL:**   ${CHAT_URL}"
+            echo "**Status:**     ${FINAL_STATUS}"
+          } >> "${GITHUB_STEP_SUMMARY}"
@@ -29,7 +29,12 @@ EDE = "EDE"
 HELO = "HELO"
 LKE = "LKE"
 byt = "byt"
+cpy = "cpy"
+Cpy = "Cpy"
 typ = "typ"
+# file extensions used in seti icon theme
+styl = "styl"
+edn = "edn"
 Inferrable = "Inferrable"

 [files]
@@ -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@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
        with:
          egress-policy: audit

@@ -30,6 +30,22 @@ jobs:
        with:
          persist-credentials: false

+      - name: Rewrite same-repo links for PR branch
+        if: github.event_name == 'pull_request'
+        env:
+          HEAD_SHA: ${{ github.event.pull_request.head.sha }}
+        run: |
+          # Rewrite same-repo blob/tree main links to the PR head SHA
+          # so that files or directories introduced in the PR are
+          # reachable during link checking.
+          {
+            echo 'replacementPatterns:'
+            echo "  - pattern: \"https://github.com/coder/coder/blob/main/\""
+            echo "    replacement: \"https://github.com/coder/coder/blob/${HEAD_SHA}/\""
+            echo "  - pattern: \"https://github.com/coder/coder/tree/main/\""
+            echo "    replacement: \"https://github.com/coder/coder/tree/${HEAD_SHA}/\""
+          } >> .github/.linkspector.yml
+
      - name: Check Markdown links
        uses: umbrelladocs/action-linkspector@652f85bc57bb1e7d4327260decc10aa68f7694c3 # v1.4.0
        id: markdown-link-check
@@ -38,6 +38,7 @@ site/.swc

 # Make target for updating generated/golden files (any dir).
 .gen
+/_gen/
 .gen-golden

 # Build
@@ -37,19 +37,20 @@ Only pause to ask for confirmation when:

 ## Essential Commands

-| Task              | Command                  | Notes                            |
-|-------------------|--------------------------|----------------------------------|
-| **Development**   | `./scripts/develop.sh`   | ⚠️ Don't use manual build        |
-| **Build**         | `make build`             | Fat binaries (includes server)   |
-| **Build Slim**    | `make build-slim`        | Slim binaries                    |
-| **Test**          | `make test`              | Full test suite                  |
-| **Test Single**   | `make test RUN=TestName` | Faster than full suite           |
-| **Test Postgres** | `make test-postgres`     | Run tests with Postgres database |
-| **Test Race**     | `make test-race`         | Run tests with Go race detector  |
-| **Lint**          | `make lint`              | Always run after changes         |
-| **Generate**      | `make gen`               | After database changes           |
-| **Format**        | `make fmt`               | Auto-format code                 |
-| **Clean**         | `make clean`             | Clean build artifacts            |
+| Task            | Command                  | Notes                               |
+|-----------------|--------------------------|-------------------------------------|
+| **Development** | `./scripts/develop.sh`   | ⚠️ Don't use manual build           |
+| **Build**       | `make build`             | Fat binaries (includes server)      |
+| **Build Slim**  | `make build-slim`        | Slim binaries                       |
+| **Test**        | `make test`              | Full test suite                     |
+| **Test Single** | `make test RUN=TestName` | Faster than full suite              |
+| **Test Race**   | `make test-race`         | Run tests with Go race detector     |
+| **Lint**        | `make lint`              | Always run after changes            |
+| **Generate**    | `make gen`               | After database changes              |
+| **Format**      | `make fmt`               | Auto-format code                    |
+| **Clean**       | `make clean`             | Clean build artifacts               |
+| **Pre-commit**  | `make pre-commit`        | Fast CI checks (gen/fmt/lint/build) |
+| **Pre-push**    | `make pre-push`          | Heavier CI checks (allowlisted)     |

 ### Documentation Commands

@@ -99,10 +100,75 @@ app, err := api.Database.GetOAuth2ProviderAppByClientID(dbauthz.AsSystemRestrict
 app, err := api.Database.GetOAuth2ProviderAppByClientID(ctx, clientID)
 ```

+### API Design
+
+- Add swagger annotations when introducing new HTTP endpoints. Do this in
+  the same change as the handler so the docs do not get missed before
+  release.
+- For user-scoped or resource-scoped routes, prefer path parameters over
+  query parameters when that matches existing route patterns.
+- For experimental or unstable API paths, skip public doc generation with
+  `// @x-apidocgen {"skip": true}` after the `@Router` annotation. This
+  keeps them out of the published API reference until they stabilize.
+
+### Database Query Naming
+
+- Use `ByX` when `X` is the lookup or filter column.
+- Use `PerX` or `GroupedByX` when `X` is the aggregation or grouping
+  dimension.
+- Avoid `ByX` names for grouped queries.
+
+### Database-to-SDK Conversions
+
+- Extract explicit db-to-SDK conversion helpers instead of inlining large
+  conversion blocks inside handlers.
+- Keep nullable-field handling, type coercion, and response shaping in the
+  converter so handlers stay focused on request flow and authorization.
+
 ## Quick Reference

 ### Full workflows available in imported WORKFLOWS.md

+### Git Hooks (MANDATORY - DO NOT SKIP)
+
+**You MUST install and use the git hooks. NEVER bypass them with
+`--no-verify`. Skipping hooks wastes CI cycles and is unacceptable.**
+
+The first run will be slow as caches warm up. Consecutive runs are
+**significantly faster** (often 10x) thanks to Go build cache,
+generated file timestamps, and warm node_modules. This is NOT a
+reason to skip them. Wait for hooks to complete before proceeding,
+no matter how long they take.
+
+```sh
+git config core.hooksPath scripts/githooks
+```
+
+Two hooks run automatically:
+
+- **pre-commit**: Classifies staged files by type and runs either
+  the full `make pre-commit` or the lightweight `make pre-commit-light`
+  depending on whether Go, TypeScript, SQL, proto, or Makefile
+  changes are present. Falls back to the full target when
+  `CODER_HOOK_RUN_ALL=1` is set. A markdown-only commit takes
+  seconds; a Go change takes several minutes.
+- **pre-push**: Classifies changed files (vs remote branch or
+  merge-base) and runs `make pre-push` when Go, TypeScript, SQL,
+  proto, or Makefile changes are detected. Skips tests entirely
+  for lightweight changes. Allowlisted in
+  `scripts/githooks/pre-push`. Runs only for developers who opt
+  in. Falls back to `make pre-push` when the diff range can't
+  be determined or `CODER_HOOK_RUN_ALL=1` is set. Allow at least
+  15 minutes for a full run.
+
+`git commit` and `git push` will appear to hang while hooks run.
+This is normal. Do not interrupt, retry, or reduce the timeout.
+
+NEVER run `git config core.hooksPath` to change or disable hooks.
+
+If a hook fails, fix the issue and retry. Do not work around the
+failure by skipping the hook.
+
 ### Git Workflow

 When working on existing PRs, check out the branch first:
@@ -151,6 +217,26 @@ seems like it should use `time.Sleep`, read through https://github.com/coder/qua

 - Follow [Uber Go Style Guide](https://github.com/uber-go/guide/blob/master/style.md)
 - Commit format: `type(scope): message`
+- PR titles follow the same `type(scope): message` format.
+- When you use a scope, it must be a real filesystem path containing every
+  changed file.
+- Use a broader path scope, or omit the scope, for cross-cutting changes.
+- Example: `fix(coderd/chatd): ...` for changes only in `coderd/chatd/`.
+
+### Frontend Patterns
+
+- Prefer existing shared UI components and utilities over custom
+  implementations. Reuse common primitives such as loading, table, and error
+  handling components when they fit the use case.
+- Use Storybook stories for all component and page testing, including
+  visual presentation, user interactions, keyboard navigation, focus
+  management, and accessibility behavior. Do not create standalone
+  vitest/RTL test files for components or pages. Stories double as living
+  documentation, visual regression coverage, and interaction test suites
+  via `play` functions. Reserve plain vitest files for pure logic only:
+  utility functions, data transformations, hooks tested via
+  `renderHook()` that do not require DOM assertions, and query/cache
+  operations with no rendered output.

 ### Writing Comments

@@ -198,13 +284,12 @@ reviewer time and clutters the diff.
 **Don't delete existing comments** that explain non-obvious behavior. These
 comments preserve important context about why code works a certain way.

-**When adding tests for new behavior**, add new test cases instead of modifying
-existing ones. This preserves coverage for the original behavior and makes it
-clear what the new test covers.
+**When adding tests for new behavior**, read existing tests first to understand what's covered. Add new cases for uncovered behavior. Edit existing tests as needed, but don't change what they verify.

 ## Detailed Development Guides

@.claude/docs/ARCHITECTURE.md
+@.claude/docs/GO.md
@.claude/docs/OAUTH2.md
@.claude/docs/TESTING.md
@.claude/docs/TROUBLESHOOTING.md
@@ -212,6 +297,27 @@ clear what the new test covers.
@.claude/docs/PR_STYLE_GUIDE.md
@.claude/docs/DOCS_STYLE_GUIDE.md

+If your agent tool does not auto-load `@`-referenced files, read these
+manually before starting work:
+
+**Always read:**
+
+- `.claude/docs/WORKFLOWS.md` — dev server, git workflow, hooks
+
+**Read when relevant to your task:**
+
+- `.claude/docs/GO.md` — Go patterns and modern Go usage (any Go changes)
+- `.claude/docs/TESTING.md` — testing patterns, race conditions (any test changes)
+- `.claude/docs/DATABASE.md` — migrations, SQLC, audit table (any DB changes)
+- `.claude/docs/ARCHITECTURE.md` — system overview (orientation or architecture work)
+- `.claude/docs/PR_STYLE_GUIDE.md` — PR description format (when writing PRs)
+- `.claude/docs/OAUTH2.md` — OAuth2 and RFC compliance (when touching auth)
+- `.claude/docs/TROUBLESHOOTING.md` — common failures and fixes (when stuck)
+- `.claude/docs/DOCS_STYLE_GUIDE.md` — docs conventions (when writing `docs/`)
+
+**For frontend work**, also read `site/AGENTS.md` before making any changes
+in `site/`.
+
 ## Local Configuration

 These files may be gitignored, read manually if not auto-loaded.
@@ -19,10 +19,84 @@ SHELL := bash
 .SHELLFLAGS := -ceu
 .ONESHELL:

+# When MAKE_TIMED=1, replace SHELL with a wrapper that prints
+# elapsed wall-clock time for each recipe. pre-commit and pre-push
+# set this on their sub-makes so every parallel job reports its
+# duration. Ad-hoc usage: make MAKE_TIMED=1 test
+ifdef MAKE_TIMED
+SHELL := $(CURDIR)/scripts/lib/timed-shell.sh
+.SHELLFLAGS = $@ -ceu
+export MAKE_TIMED
+export MAKE_LOGDIR
+endif
+
 # This doesn't work on directories.
 # See https://stackoverflow.com/questions/25752543/make-delete-on-error-for-directory-targets
 .DELETE_ON_ERROR:

+# Protect git-tracked generated files from deletion on interrupt.
+# .DELETE_ON_ERROR is desirable for most targets but for files that
+# are committed to git and serve as inputs to other rules, deletion
+# is worse than a stale file — `git restore` is the recovery path.
+.PRECIOUS: \
+	coderd/database/dump.sql \
+	coderd/database/querier.go \
+	coderd/database/unique_constraint.go \
+	coderd/database/dbmetrics/querymetrics.go \
+	coderd/database/dbauthz/dbauthz.go \
+	coderd/database/dbmock/dbmock.go \
+	coderd/database/pubsub/psmock/psmock.go \
+	agent/agentcontainers/acmock/acmock.go \
+	coderd/httpmw/loggermw/loggermock/loggermock.go \
+	codersdk/workspacesdk/agentconnmock/agentconnmock.go \
+	tailnet/tailnettest/coordinatormock.go \
+	tailnet/tailnettest/coordinateemock.go \
+	tailnet/tailnettest/workspaceupdatesprovidermock.go \
+	tailnet/tailnettest/subscriptionmock.go \
+	enterprise/aibridged/aibridgedmock/clientmock.go \
+	enterprise/aibridged/aibridgedmock/poolmock.go \
+	tailnet/proto/tailnet.pb.go \
+	agent/proto/agent.pb.go \
+	agent/agentsocket/proto/agentsocket.pb.go \
+	agent/boundarylogproxy/codec/boundary.pb.go \
+	provisionersdk/proto/provisioner.pb.go \
+	provisionerd/proto/provisionerd.pb.go \
+	vpn/vpn.pb.go \
+	enterprise/aibridged/proto/aibridged.pb.go \
+	site/src/api/typesGenerated.ts \
+	site/e2e/provisionerGenerated.ts \
+	site/src/api/chatModelOptionsGenerated.json \
+	site/src/api/rbacresourcesGenerated.ts \
+	site/src/api/countriesGenerated.ts \
+	site/src/theme/icons.json \
+	examples/examples.gen.json \
+	docs/manifest.json \
+	docs/admin/integrations/prometheus.md \
+	docs/admin/security/audit-logs.md \
+	docs/reference/cli/index.md \
+	coderd/apidoc/swagger.json \
+	coderd/rbac/object_gen.go \
+	coderd/rbac/scopes_constants_gen.go \
+	codersdk/rbacresources_gen.go \
+	codersdk/apikey_scopes_gen.go
+
+# atomic_write runs a command, captures stdout into a temp file, and
+# atomically replaces $@. An optional second argument is a formatting
+# command that receives the temp file path as its argument.
+# Usage: $(call atomic_write,GENERATE_CMD[,FORMAT_CMD])
+define atomic_write
+	tmpdir=$$(mktemp -d -p _gen) && tmpfile=$$(realpath "$$tmpdir")/$(notdir $@) && \
+		$(1) > "$$tmpfile" && \
+		$(if $(2),$(2) "$$tmpfile" &&) \
+		mv "$$tmpfile" "$@" && rm -rf "$$tmpdir"
+endef
+
+# 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
+_gen:
+	mkdir -p _gen
+
 # Don't print the commands in the file unless you specify VERBOSE. This is
 # essentially the same as putting "@" at the start of each line.
 ifndef VERBOSE
@@ -40,11 +114,19 @@ VERSION      := $(shell ./scripts/version.sh)
 POSTGRES_VERSION ?= 17
 POSTGRES_IMAGE   ?= us-docker.pkg.dev/coder-v2-images-public/public/postgres:$(POSTGRES_VERSION)

-# Use the highest ZSTD compression level in CI.
-ifdef CI
+# Limit parallel Make jobs in pre-commit/pre-push. Defaults to
+# nproc/4 (min 2) since test, lint, and build targets have internal
+# parallelism. Override: make pre-push PARALLEL_JOBS=8
+PARALLEL_JOBS ?= $(shell n=$$(nproc 2>/dev/null || sysctl -n hw.ncpu 2>/dev/null || echo 8); echo $$(( n / 4 > 2 ? n / 4 : 2 )))
+
+# Use the highest ZSTD compression level in release builds to
+# minimize artifact size. For non-release CI builds (e.g. main
+# branch preview), use multithreaded level 6 which is ~99% faster
+# at the cost of ~30% larger archives.
+ifeq ($(CODER_RELEASE),true)
 ZSTDFLAGS := -22 --ultra
 else
-ZSTDFLAGS := -6
+ZSTDFLAGS := -6 -T0
 endif

 # Common paths to exclude from find commands, this rule is written so
@@ -53,19 +135,11 @@ endif
 # Note, all find statements should be written with `.` or `./path` as
 # the search path so that these exclusions match.
 FIND_EXCLUSIONS= \
-	-not \( \( -path '*/.git/*' -o -path './build/*' -o -path './vendor/*' -o -path './.coderv2/*' -o -path '*/node_modules/*' -o -path '*/out/*' -o -path './coderd/apidoc/*' -o -path '*/.next/*' -o -path '*/.terraform/*' \) -prune \)
+	-not \( \( -path '*/.git/*' -o -path './build/*' -o -path './vendor/*' -o -path './.coderv2/*' -o -path '*/node_modules/*' -o -path '*/out/*' -o -path './coderd/apidoc/*' -o -path '*/.next/*' -o -path '*/.terraform/*' -o -path './_gen/*' \) -prune \)
+
 # Source files used for make targets, evaluated on use.
 GO_SRC_FILES := $(shell find . $(FIND_EXCLUSIONS) -type f -name '*.go' -not -name '*_test.go')
-# Same as GO_SRC_FILES but excluding certain files that have problematic
-# Makefile dependencies (e.g. pnpm).
-MOST_GO_SRC_FILES := $(shell \
-	find . \
-		$(FIND_EXCLUSIONS) \
-		-type f \
-		-name '*.go' \
-		-not -name '*_test.go' \
-		-not -wholename './agent/agentcontainers/dcspec/dcspec_gen.go' \
-)
+
 # All the shell files in the repo, excluding ignored files.
 SHELL_SRC_FILES := $(shell find . $(FIND_EXCLUSIONS) -type f -name '*.sh')

@@ -94,12 +168,8 @@ PACKAGE_OS_ARCHES := linux_amd64 linux_armv7 linux_arm64
 # All architectures we build Docker images for (Linux only).
 DOCKER_ARCHES := amd64 arm64 armv7

-# All ${OS}_${ARCH} combos we build the desktop dylib for.
-DYLIB_ARCHES := darwin_amd64 darwin_arm64
-
 # Computed variables based on the above.
 CODER_SLIM_BINARIES      := $(addprefix build/coder-slim_$(VERSION)_,$(OS_ARCHES))
-CODER_DYLIBS             := $(foreach os_arch, $(DYLIB_ARCHES), build/coder-vpn_$(VERSION)_$(os_arch).dylib)
 CODER_FAT_BINARIES       := $(addprefix build/coder_$(VERSION)_,$(OS_ARCHES))
 CODER_ALL_BINARIES       := $(CODER_SLIM_BINARIES) $(CODER_FAT_BINARIES)
 CODER_TAR_GZ_ARCHIVES    := $(foreach os_arch, $(ARCHIVE_TAR_GZ), build/coder_$(VERSION)_$(os_arch).tar.gz)
@@ -261,26 +331,6 @@ $(CODER_ALL_BINARIES): go.mod go.sum \
 		fi
 	fi

-# This task builds Coder Desktop dylibs
-$(CODER_DYLIBS): go.mod go.sum $(MOST_GO_SRC_FILES)
-	@if [ "$(shell uname)" = "Darwin" ]; then
-		$(get-mode-os-arch-ext)
-		./scripts/build_go.sh \
-			--os "$$os" \
-			--arch "$$arch" \
-			--version "$(VERSION)" \
-			--output "$@" \
-			--dylib
-
-	else
-		echo "ERROR: Can't build dylib on non-Darwin OS" 1>&2
-		exit 1
-	fi
-
-# This task builds both dylibs
-build/coder-dylib: $(CODER_DYLIBS)
-.PHONY: build/coder-dylib
-
 # This task builds all archives. It parses the target name to get the metadata
 # for the build, so it must be specified in this format:
 #     build/coder_${version}_${os}_${arch}.${format}
@@ -427,6 +477,7 @@ SITE_GEN_FILES := \
 	site/src/api/typesGenerated.ts \
 	site/src/api/rbacresourcesGenerated.ts \
 	site/src/api/countriesGenerated.ts \
+	site/src/api/chatModelOptionsGenerated.json \
 	site/src/theme/icons.json

 site/out/index.html: \
@@ -455,13 +506,26 @@ install: build/coder_$(VERSION)_$(GOOS)_$(GOARCH)$(GOOS_BIN_EXT)
 	cp "$<" "$$output_file"
 .PHONY: install

+# Only wildcard the go files in the develop directory to avoid rebuilds
+# when project files are changd. Technically changes to some imports may
+# not be detected, but it's unlikely to cause any issues.
+build/.bin/develop: go.mod go.sum $(wildcard scripts/develop/*.go)
+	CGO_ENABLED=0 go build -o $@ ./scripts/develop
+
 BOLD := $(shell tput bold 2>/dev/null)
 GREEN := $(shell tput setaf 2 2>/dev/null)
+RED := $(shell tput setaf 1 2>/dev/null)
+YELLOW := $(shell tput setaf 3 2>/dev/null)
+DIM := $(shell tput dim 2>/dev/null || tput setaf 8 2>/dev/null)
 RESET := $(shell tput sgr0 2>/dev/null)

 fmt: fmt/ts fmt/go fmt/terraform fmt/shfmt fmt/biome fmt/markdown
 .PHONY: fmt

+# Subset of fmt that does not require Go or Node toolchains.
+fmt-light: fmt/shfmt fmt/terraform fmt/markdown
+.PHONY: fmt-light
+
 fmt/go:
 ifdef FILE
 	# Format single file
@@ -566,9 +630,13 @@ endif
 # GitHub Actions linters are run in a separate CI job (lint-actions) that only
 # triggers when workflow files change, so we skip them here when CI=true.
 LINT_ACTIONS_TARGETS := $(if $(CI),,lint/actions/actionlint)
-lint: lint/shellcheck lint/go lint/ts lint/examples lint/helm lint/site-icons lint/markdown lint/check-scopes lint/migrations $(LINT_ACTIONS_TARGETS)
+lint: lint/shellcheck lint/go lint/ts lint/examples lint/helm lint/site-icons lint/markdown lint/check-scopes lint/migrations lint/bootstrap $(LINT_ACTIONS_TARGETS)
 .PHONY: lint

+# Subset of lint that does not require Go or Node toolchains.
+lint-light: lint/shellcheck lint/markdown lint/helm lint/bootstrap lint/migrations lint/actions/actionlint lint/typos
+.PHONY: lint-light
+
 lint/site-icons:
 	./scripts/check_site_icons.sh
 .PHONY: lint/site-icons
@@ -581,7 +649,7 @@ lint/ts: site/node_modules/.installed
 lint/go:
 	./scripts/check_enterprise_imports.sh
 	./scripts/check_codersdk_imports.sh
-	linter_ver=$(shell egrep -o 'GOLANGCI_LINT_VERSION=\S+' dogfood/coder/Dockerfile | cut -d '=' -f 2)
+	linter_ver=$$(grep -oE 'GOLANGCI_LINT_VERSION=\S+' dogfood/coder/Dockerfile | cut -d '=' -f 2)
 	go run github.com/golangci/golangci-lint/cmd/golangci-lint@v$$linter_ver run
 	go tool github.com/coder/paralleltestctx/cmd/paralleltestctx -custom-funcs="testutil.Context" ./...
 .PHONY: lint/go
@@ -596,6 +664,11 @@ lint/shellcheck: $(SHELL_SRC_FILES)
 	shellcheck --external-sources $(SHELL_SRC_FILES)
 .PHONY: lint/shellcheck

+lint/bootstrap:
+	bash scripts/check_bootstrap_quotes.sh
+.PHONY: lint/bootstrap
+
+
 lint/helm:
 	cd helm/
 	make lint
@@ -630,13 +703,129 @@ lint/migrations:
 	./scripts/check_pg_schema.sh "Fixtures" $(FIXTURE_FILES)
 .PHONY: lint/migrations

+TYPOS_VERSION := $(shell grep -oP 'crate-ci/typos@\S+\s+\#\s+v\K[0-9.]+' .github/workflows/ci.yaml)
+
+# Map uname values to typos release asset names.
+TYPOS_ARCH := $(shell uname -m)
+ifeq ($(shell uname -s),Darwin)
+TYPOS_OS := apple-darwin
+else
+TYPOS_OS := unknown-linux-musl
+endif
+
+build/typos-$(TYPOS_VERSION):
+	mkdir -p build/
+	curl -sSfL "https://github.com/crate-ci/typos/releases/download/v$(TYPOS_VERSION)/typos-v$(TYPOS_VERSION)-$(TYPOS_ARCH)-$(TYPOS_OS).tar.gz" \
+		| tar -xzf - -C build/ ./typos
+	mv build/typos "$@"
+
+lint/typos: build/typos-$(TYPOS_VERSION)
+	build/typos-$(TYPOS_VERSION) --config .github/workflows/typos.toml
+.PHONY: lint/typos
+
+# pre-commit and pre-push mirror CI checks locally.
+#
+# pre-commit runs checks that don't need external services (Docker,
+# Playwright). This is the git pre-commit hook default since Docker
+# and browser issues in the local environment would otherwise block
+# all commits.
+#
+# pre-push adds heavier checks: Go tests, JS tests, and site build.
+# 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
+# parallel via -j. It fails if any tracked files have unstaged
+# changes afterward.
+
+define check-unstaged
+	unstaged="$$(git diff --name-only)"
+	if [[ -n $$unstaged ]]; then
+		echo "$(RED)✗ check unstaged changes$(RESET)"
+		echo "$$unstaged" | sed 's/^/  - /'
+		echo ""
+		echo "$(DIM)  Verify generated changes are correct before staging:$(RESET)"
+		echo "$(DIM)    git diff$(RESET)"
+		echo "$(DIM)    git add -u && git commit$(RESET)"
+		exit 1
+	fi
+endef
+define check-untracked
+	untracked=$$(git ls-files --other --exclude-standard)
+	if [[ -n $$untracked ]]; then
+		echo "$(YELLOW)? check untracked files$(RESET)"
+		echo "$$untracked" | sed 's/^/  - /'
+		echo ""
+		echo "$(DIM)  Review if these should be committed or added to .gitignore.$(RESET)"
+	fi
+endef
+
+pre-commit:
+	start=$$(date +%s)
+	logdir=$$(mktemp -d "$${TMPDIR:-/tmp}/coder-pre-commit.XXXXXX")
+	echo "$(BOLD)pre-commit$(RESET) ($$logdir)"
+	echo "gen + fmt:"
+	$(MAKE) --no-print-directory -j$(PARALLEL_JOBS) MAKE_TIMED=1 MAKE_LOGDIR=$$logdir gen fmt
+	$(check-unstaged)
+	echo "lint + build:"
+	$(MAKE) --no-print-directory -j$(PARALLEL_JOBS) MAKE_TIMED=1 MAKE_LOGDIR=$$logdir \
+		lint \
+		lint/typos \
+		build/coder-slim_$(GOOS)_$(GOARCH)$(GOOS_BIN_EXT)
+	$(check-unstaged)
+	$(check-untracked)
+	rm -rf $$logdir
+	echo "$(GREEN)✓ pre-commit passed$(RESET) ($$(( $$(date +%s) - $$start ))s)"
+.PHONY: pre-commit
+
+# Lightweight pre-commit for changes that don't touch Go or
+# TypeScript. Skips gen, lint/go, lint/ts, fmt/go, fmt/ts, and
+# the binary build. Used by the pre-commit hook when only docs,
+# shell, terraform, helm, or other fast-to-check files changed.
+pre-commit-light:
+	start=$$(date +%s)
+	logdir=$$(mktemp -d "$${TMPDIR:-/tmp}/coder-pre-commit-light.XXXXXX")
+	echo "$(BOLD)pre-commit-light$(RESET) ($$logdir)"
+	echo "fmt:"
+	$(MAKE) --no-print-directory -j$(PARALLEL_JOBS) MAKE_TIMED=1 MAKE_LOGDIR=$$logdir fmt-light
+	$(check-unstaged)
+	echo "lint:"
+	$(MAKE) --no-print-directory -j$(PARALLEL_JOBS) MAKE_TIMED=1 MAKE_LOGDIR=$$logdir lint-light
+	$(check-unstaged)
+	$(check-untracked)
+	rm -rf $$logdir
+	echo "$(GREEN)✓ pre-commit-light passed$(RESET) ($$(( $$(date +%s) - $$start ))s)"
+.PHONY: pre-commit-light
+
+pre-push:
+	start=$$(date +%s)
+	logdir=$$(mktemp -d "$${TMPDIR:-/tmp}/coder-pre-push.XXXXXX")
+	echo "$(BOLD)pre-push$(RESET) ($$logdir)"
+	echo "test + build site:"
+	$(MAKE) --no-print-directory -j$(PARALLEL_JOBS) MAKE_TIMED=1 MAKE_LOGDIR=$$logdir \
+		test \
+		test-js \
+		test-storybook \
+		site/out/index.html
+	rm -rf $$logdir
+	echo "$(GREEN)✓ pre-push passed$(RESET) ($$(( $$(date +%s) - $$start ))s)"
+.PHONY: pre-push
+
+offlinedocs/check: offlinedocs/node_modules/.installed
+	cd offlinedocs/
+	pnpm format:check
+	pnpm lint
+	pnpm export
+.PHONY: offlinedocs/check
+
 # All files generated by the database should be added here, and this can be used
 # as a target for jobs that need to run after the database is generated.
 DB_GEN_FILES := \
 	coderd/database/dump.sql \
 	coderd/database/querier.go \
 	coderd/database/unique_constraint.go \
-	coderd/database/dbmetrics/dbmetrics.go \
+	coderd/database/dbmetrics/querymetrics.go \
 	coderd/database/dbauthz/dbauthz.go \
 	coderd/database/dbmock/dbmock.go

@@ -654,6 +843,7 @@ GEN_FILES := \
 	tailnet/proto/tailnet.pb.go \
 	agent/proto/agent.pb.go \
 	agent/agentsocket/proto/agentsocket.pb.go \
+	agent/boundarylogproxy/codec/boundary.pb.go \
 	provisionersdk/proto/provisioner.pb.go \
 	provisionerd/proto/provisionerd.pb.go \
 	vpn/vpn.pb.go \
@@ -670,6 +860,7 @@ GEN_FILES := \
 	coderd/apidoc/swagger.json \
 	docs/manifest.json \
 	provisioner/terraform/testdata/version \
+	scripts/metricsdocgen/generated_metrics \
 	site/e2e/provisionerGenerated.ts \
 	examples/examples.gen.json \
 	$(TAILNETTEST_MOCKS) \
@@ -709,16 +900,24 @@ gen/mark-fresh:
 		provisionersdk/proto/provisioner.pb.go \
 		provisionerd/proto/provisionerd.pb.go \
 		agent/agentsocket/proto/agentsocket.pb.go \
+		agent/boundarylogproxy/codec/boundary.pb.go \
 		vpn/vpn.pb.go \
 		enterprise/aibridged/proto/aibridged.pb.go \
 		coderd/database/dump.sql \
-		$(DB_GEN_FILES) \
+		coderd/database/querier.go \
+		coderd/database/unique_constraint.go \
+		coderd/database/dbmetrics/querymetrics.go \
+		coderd/database/dbauthz/dbauthz.go \
+		coderd/database/dbmock/dbmock.go \
+		coderd/database/pubsub/psmock/psmock.go \
 		site/src/api/typesGenerated.ts \
 		coderd/rbac/object_gen.go \
 		codersdk/rbacresources_gen.go \
 		coderd/rbac/scopes_constants_gen.go \
+		codersdk/apikey_scopes_gen.go \
 		site/src/api/rbacresourcesGenerated.ts \
 		site/src/api/countriesGenerated.ts \
+		site/src/api/chatModelOptionsGenerated.json \
 		docs/admin/integrations/prometheus.md \
 		docs/reference/cli/index.md \
 		docs/admin/security/audit-logs.md \
@@ -727,8 +926,8 @@ gen/mark-fresh:
 		site/e2e/provisionerGenerated.ts \
 		site/src/theme/icons.json \
 		examples/examples.gen.json \
+		scripts/metricsdocgen/generated_metrics \
 		$(TAILNETTEST_MOCKS) \
-		coderd/database/pubsub/psmock/psmock.go \
 		agent/agentcontainers/acmock/acmock.go \
 		agent/agentcontainers/dcspec/dcspec_gen.go \
 		coderd/httpmw/loggermw/loggermock/loggermock.go \
@@ -757,9 +956,19 @@ coderd/database/dump.sql: coderd/database/gen/dump/main.go $(wildcard coderd/dat
 # Generates Go code for querying the database.
 # coderd/database/queries.sql.go
 # coderd/database/models.go
-coderd/database/querier.go: coderd/database/sqlc.yaml coderd/database/dump.sql $(wildcard coderd/database/queries/*.sql)
-	./coderd/database/generate.sh
-	touch "$@"
+#
+# NOTE: grouped target (&:) ensures generate.sh runs only once even
+# with -j and all outputs are considered produced together. These
+# files are all written by generate.sh (via sqlc and scripts/dbgen).
+coderd/database/querier.go \
+coderd/database/unique_constraint.go \
+coderd/database/dbmetrics/querymetrics.go \
+coderd/database/dbauthz/dbauthz.go &: \
+	coderd/database/sqlc.yaml \
+	coderd/database/dump.sql \
+	$(wildcard coderd/database/queries/*.sql)
+	SKIP_DUMP_SQL=1 ./coderd/database/generate.sh
+	touch coderd/database/querier.go coderd/database/unique_constraint.go coderd/database/dbmetrics/querymetrics.go coderd/database/dbauthz/dbauthz.go

 coderd/database/dbmock/dbmock.go: coderd/database/db.go coderd/database/querier.go
 	go generate ./coderd/database/dbmock/
@@ -798,7 +1007,7 @@ $(TAILNETTEST_MOCKS): tailnet/coordinator.go tailnet/service.go
 	touch "$@"

 tailnet/proto/tailnet.pb.go: tailnet/proto/tailnet.proto
-	protoc \
+	./scripts/atomic_protoc.sh \
 		--go_out=. \
 		--go_opt=paths=source_relative \
 		--go-drpc_out=. \
@@ -806,15 +1015,15 @@ tailnet/proto/tailnet.pb.go: tailnet/proto/tailnet.proto
 		./tailnet/proto/tailnet.proto

 agent/proto/agent.pb.go: agent/proto/agent.proto
-	protoc \
+	./scripts/atomic_protoc.sh \
 		--go_out=. \
 		--go_opt=paths=source_relative \
 		--go-drpc_out=. \
 		--go-drpc_opt=paths=source_relative \
 		./agent/proto/agent.proto

-agent/agentsocket/proto/agentsocket.pb.go: agent/agentsocket/proto/agentsocket.proto
-	protoc \
+agent/agentsocket/proto/agentsocket.pb.go: agent/agentsocket/proto/agentsocket.proto agent/proto/agent.proto
+	./scripts/atomic_protoc.sh \
 		--go_out=. \
 		--go_opt=paths=source_relative \
 		--go-drpc_out=. \
@@ -822,7 +1031,7 @@ agent/agentsocket/proto/agentsocket.pb.go: agent/agentsocket/proto/agentsocket.p
 		./agent/agentsocket/proto/agentsocket.proto

 provisionersdk/proto/provisioner.pb.go: provisionersdk/proto/provisioner.proto
-	protoc \
+	./scripts/atomic_protoc.sh \
 		--go_out=. \
 		--go_opt=paths=source_relative \
 		--go-drpc_out=. \
@@ -830,7 +1039,7 @@ provisionersdk/proto/provisioner.pb.go: provisionersdk/proto/provisioner.proto
 		./provisionersdk/proto/provisioner.proto

 provisionerd/proto/provisionerd.pb.go: provisionerd/proto/provisionerd.proto
-	protoc \
+	./scripts/atomic_protoc.sh \
 		--go_out=. \
 		--go_opt=paths=source_relative \
 		--go-drpc_out=. \
@@ -838,97 +1047,110 @@ provisionerd/proto/provisionerd.pb.go: provisionerd/proto/provisionerd.proto
 		./provisionerd/proto/provisionerd.proto

 vpn/vpn.pb.go: vpn/vpn.proto
-	protoc \
+	./scripts/atomic_protoc.sh \
 		--go_out=. \
 		--go_opt=paths=source_relative \
 		./vpn/vpn.proto

+agent/boundarylogproxy/codec/boundary.pb.go: agent/boundarylogproxy/codec/boundary.proto agent/proto/agent.proto
+	./scripts/atomic_protoc.sh \
+		--go_out=. \
+		--go_opt=paths=source_relative \
+		./agent/boundarylogproxy/codec/boundary.proto
+
 enterprise/aibridged/proto/aibridged.pb.go: enterprise/aibridged/proto/aibridged.proto
-	protoc \
+	./scripts/atomic_protoc.sh \
 		--go_out=. \
 		--go_opt=paths=source_relative \
 		--go-drpc_out=. \
 		--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')
-	# -C sets the directory for the go run command
-	go run -C ./scripts/apitypings main.go > $@
-	./scripts/biome_format.sh src/api/typesGenerated.ts
-	touch "$@"
+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/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/*) $(wildcard site/static/icon/*)
-	go run ./scripts/gensite/ -icons "$@"
-	./scripts/biome_format.sh src/theme/icons.json
+site/src/theme/icons.json: site/node_modules/.installed $(wildcard scripts/gensite/*) $(wildcard site/static/icon/*) | _gen
+	tmpdir=$$(mktemp -d -p _gen) && tmpfile=$$(realpath "$$tmpdir")/$(notdir $@) && \
+		go run ./scripts/gensite/ -icons "$$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)
+
+coderd/rbac/object_gen.go: scripts/typegen/rbacobject.gotmpl scripts/typegen/main.go coderd/rbac/object.go coderd/rbac/policy/policy.go | _gen
+	$(call atomic_write,go run ./scripts/typegen/main.go rbac object)
 	touch "$@"

-examples/examples.gen.json: scripts/examplegen/main.go examples/examples.go $(shell find ./examples/templates)
-	go run ./scripts/examplegen/main.go > examples/examples.gen.json
+# NOTE: depends on object_gen.go because `go run` 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
+	# Write to a temp file first to avoid truncating the package
+	# during build since the generator imports the rbac package.
+	$(call atomic_write,go run ./scripts/typegen/main.go rbac scopenames)
 	touch "$@"

-coderd/rbac/object_gen.go: scripts/typegen/rbacobject.gotmpl scripts/typegen/main.go coderd/rbac/object.go coderd/rbac/policy/policy.go
-	tempdir=$(shell mktemp -d /tmp/typegen_rbac_object.XXXXXX)
-	go run ./scripts/typegen/main.go rbac object > "$$tempdir/object_gen.go"
-	mv -v "$$tempdir/object_gen.go" coderd/rbac/object_gen.go
-	rmdir -v "$$tempdir"
+# NOTE: depends on object_gen.go and scopes_constants_gen.go because
+# `go run` 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
+	# Write to a temp file to avoid truncating the target, which
+	# would break the codersdk package and any parallel build targets.
+	$(call atomic_write,go run scripts/typegen/main.go rbac codersdk)
 	touch "$@"

-coderd/rbac/scopes_constants_gen.go: scripts/typegen/scopenames.gotmpl scripts/typegen/main.go coderd/rbac/policy/policy.go
-	# Generate typed low-level ScopeName constants from RBACPermissions
-	# Write to a temp file first to avoid truncating the package during build
-	# since the generator imports the rbac package.
-	tempfile=$(shell mktemp /tmp/scopes_constants_gen.XXXXXX)
-	go run ./scripts/typegen/main.go rbac scopenames > "$$tempfile"
-	mv -v "$$tempfile" coderd/rbac/scopes_constants_gen.go
-	touch "$@"
-
-codersdk/rbacresources_gen.go: scripts/typegen/codersdk.gotmpl scripts/typegen/main.go coderd/rbac/object.go coderd/rbac/policy/policy.go
-	# Do no overwrite codersdk/rbacresources_gen.go directly, as it would make the file empty, breaking
- 	# the `codersdk` package and any parallel build targets.
-	go run scripts/typegen/main.go rbac codersdk > /tmp/rbacresources_gen.go
-	mv /tmp/rbacresources_gen.go codersdk/rbacresources_gen.go
-	touch "$@"
-
-codersdk/apikey_scopes_gen.go: scripts/apikeyscopesgen/main.go coderd/rbac/scopes_catalog.go coderd/rbac/scopes.go
+# NOTE: depends on object_gen.go and scopes_constants_gen.go because
+# `go run` 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
 	# Generate SDK constants for external API key scopes.
-	go run ./scripts/apikeyscopesgen > /tmp/apikey_scopes_gen.go
-	mv /tmp/apikey_scopes_gen.go codersdk/apikey_scopes_gen.go
+	$(call atomic_write,go run ./scripts/apikeyscopesgen)
 	touch "$@"

-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
-	go run scripts/typegen/main.go rbac typescript > "$@"
-	./scripts/biome_format.sh src/api/rbacresourcesGenerated.ts
-	touch "$@"
+# NOTE: depends on object_gen.go and scopes_constants_gen.go because
+# `go run` 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)

-site/src/api/countriesGenerated.ts: site/node_modules/.installed scripts/typegen/countries.tstmpl scripts/typegen/main.go codersdk/countries.go
-	go run scripts/typegen/main.go countries > "$@"
-	./scripts/biome_format.sh src/api/countriesGenerated.ts
-	touch "$@"
+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)

-scripts/metricsdocgen/generated_metrics: $(GO_SRC_FILES)
-	go run ./scripts/metricsdocgen/scanner > $@
+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)

-docs/admin/integrations/prometheus.md: node_modules/.installed scripts/metricsdocgen/main.go scripts/metricsdocgen/metrics scripts/metricsdocgen/generated_metrics
-	go run scripts/metricsdocgen/main.go
-	pnpm exec markdownlint-cli2 --fix ./docs/admin/integrations/prometheus.md
-	pnpm exec markdown-table-formatter ./docs/admin/integrations/prometheus.md
-	touch "$@"
+scripts/metricsdocgen/generated_metrics: $(GO_SRC_FILES) | _gen
+	$(call atomic_write,go run ./scripts/metricsdocgen/scanner)

-docs/reference/cli/index.md: node_modules/.installed scripts/clidocgen/main.go examples/examples.gen.json $(GO_SRC_FILES)
-	CI=true BASE_PATH="." go run ./scripts/clidocgen
-	pnpm exec markdownlint-cli2 --fix ./docs/reference/cli/*.md
-	pnpm exec markdown-table-formatter ./docs/reference/cli/*.md
-	touch "$@"
+docs/admin/integrations/prometheus.md: node_modules/.installed scripts/metricsdocgen/main.go scripts/metricsdocgen/metrics scripts/metricsdocgen/generated_metrics | _gen
+	tmpdir=$$(mktemp -d -p _gen) && tmpfile=$$(realpath "$$tmpdir")/$(notdir $@) && cp "$@" "$$tmpfile" && \
+		go run scripts/metricsdocgen/main.go --prometheus-doc-file="$$tmpfile" && \
+		pnpm exec markdownlint-cli2 --fix "$$tmpfile" && \
+		pnpm exec markdown-table-formatter "$$tmpfile" && \
+		mv "$$tmpfile" "$@" && 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
-	go run scripts/auditdocgen/main.go
-	pnpm exec markdownlint-cli2 --fix ./docs/admin/security/audit-logs.md
-	pnpm exec markdown-table-formatter ./docs/admin/security/audit-logs.md
-	touch "$@"
+docs/reference/cli/index.md: node_modules/.installed scripts/clidocgen/main.go examples/examples.gen.json $(GO_SRC_FILES) | _gen
+	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 && \
+		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 "$$tmpdir"
+
+docs/admin/security/audit-logs.md: node_modules/.installed coderd/database/querier.go scripts/auditdocgen/main.go enterprise/audit/table.go coderd/rbac/object_gen.go | _gen
+	tmpdir=$$(mktemp -d -p _gen) && tmpfile=$$(realpath "$$tmpdir")/$(notdir $@) && cp "$@" "$$tmpfile" && \
+		go run scripts/auditdocgen/main.go --audit-doc-file="$$tmpfile" && \
+		pnpm exec markdownlint-cli2 --fix "$$tmpfile" && \
+		pnpm exec markdown-table-formatter "$$tmpfile" && \
+		mv "$$tmpfile" "$@" && rm -rf "$$tmpdir"

 coderd/apidoc/.gen: \
 	node_modules/.installed \
@@ -943,18 +1165,29 @@ coderd/apidoc/.gen: \
 	scripts/apidocgen/generate.sh \
 	scripts/apidocgen/swaginit/main.go \
 	$(wildcard scripts/apidocgen/postprocess/*) \
-	$(wildcard scripts/apidocgen/markdown-template/*)
-	./scripts/apidocgen/generate.sh
-	pnpm exec markdownlint-cli2 --fix ./docs/reference/api/*.md
-	pnpm exec markdown-table-formatter ./docs/reference/api/*.md
+	$(wildcard scripts/apidocgen/markdown-template/*) | _gen
+	tmpdir=$$(mktemp -d -p _gen) && swagtmp=$$(mktemp -d -p _gen) && \
+		tmpdir=$$(realpath "$$tmpdir") && swagtmp=$$(realpath "$$swagtmp") && \
+		mkdir -p "$$tmpdir/reference/api" && \
+		cp docs/manifest.json "$$tmpdir/manifest.json" && \
+		SWAG_OUTPUT_DIR="$$swagtmp" APIDOCGEN_DOCS_DIR="$$tmpdir" ./scripts/apidocgen/generate.sh && \
+		pnpm exec markdownlint-cli2 --fix "$$tmpdir/reference/api/*.md" && \
+		pnpm exec markdown-table-formatter "$$tmpdir/reference/api/*.md" && \
+		./scripts/biome_format.sh "$$swagtmp/swagger.json" && \
+		for f in "$$tmpdir/reference/api/"*.md; do mv "$$f" "docs/reference/api/$$(basename "$$f")"; done && \
+		mv "$$tmpdir/manifest.json" _gen/manifest-staging.json && \
+		mv "$$swagtmp/docs.go" coderd/apidoc/docs.go && \
+		mv "$$swagtmp/swagger.json" coderd/apidoc/swagger.json && \
+		rm -rf "$$tmpdir" "$$swagtmp"
 	touch "$@"

-docs/manifest.json: site/node_modules/.installed coderd/apidoc/.gen docs/reference/cli/index.md
-	./scripts/biome_format.sh ../docs/manifest.json
-	touch "$@"
+docs/manifest.json: site/node_modules/.installed coderd/apidoc/.gen docs/reference/cli/index.md | _gen
+	tmpdir=$$(mktemp -d -p _gen) && tmpfile=$$(realpath "$$tmpdir")/$(notdir $@) && \
+		cp _gen/manifest-staging.json "$$tmpfile" && \
+		./scripts/biome_format.sh "$$tmpfile" && \
+		mv "$$tmpfile" "$@" && rm -rf "$$tmpdir"

 coderd/apidoc/swagger.json: site/node_modules/.installed coderd/apidoc/.gen
-	./scripts/biome_format.sh ../coderd/apidoc/swagger.json
 	touch "$@"

 update-golden-files:
@@ -1022,7 +1255,7 @@ coderd/notifications/.gen-golden: $(wildcard coderd/notifications/testdata/*/*.g
 	TZ=UTC go test ./coderd/notifications -run="Test.*Golden$$" -update
 	touch "$@"

-provisioner/terraform/testdata/.gen-golden: $(wildcard provisioner/terraform/testdata/*/*.golden) $(GO_SRC_FILES) $(wildcard provisioner/terraform/*_test.go)
+provisioner/terraform/testdata/.gen-golden: $(wildcard provisioner/terraform/testdata/*/*.golden) $(wildcard provisioner/terraform/testdata/*/*/*.golden) $(GO_SRC_FILES) $(wildcard provisioner/terraform/*_test.go)
 	TZ=UTC go test ./provisioner/terraform -run="Test.*Golden$$" -update
 	touch "$@"

@@ -1039,10 +1272,22 @@ else
 GOTESTSUM_RETRY_FLAGS :=
 endif

-# default to 8x8 parallelism to avoid overwhelming our workspaces. Hopefully we can remove these defaults
-# when we get our test suite's resource utilization under control.
-# Use testsmallbatch tag to reduce wireguard memory allocation in tests (from ~18GB to negligible).
-GOTEST_FLAGS := -tags=testsmallbatch -v -p $(or $(TEST_NUM_PARALLEL_PACKAGES),"8") -parallel=$(or $(TEST_NUM_PARALLEL_TESTS),"8")
+# Default to 8x8 parallelism to avoid overwhelming our workspaces.
+# Race detection defaults to 4x4 because the detector adds significant
+# CPU overhead. Override via TEST_NUM_PARALLEL_PACKAGES /
+# TEST_NUM_PARALLEL_TESTS.
+TEST_PARALLEL_PACKAGES := $(or $(TEST_NUM_PARALLEL_PACKAGES),8)
+TEST_PARALLEL_TESTS := $(or $(TEST_NUM_PARALLEL_TESTS),8)
+RACE_PARALLEL_PACKAGES := $(or $(TEST_NUM_PARALLEL_PACKAGES),4)
+RACE_PARALLEL_TESTS := $(or $(TEST_NUM_PARALLEL_TESTS),4)
+
+# Use testsmallbatch tag to reduce wireguard memory allocation in tests
+# (from ~18GB to negligible). Recursively expanded so target-specific
+# overrides of TEST_PARALLEL_* take effect (e.g. test-race lowers
+# parallelism). CI job timeout is 25m (see test-go-pg in ci.yaml),
+# keep the Go timeout 5m shorter so tests produce goroutine dumps
+# instead of the CI runner killing the process with no output.
+GOTEST_FLAGS = -tags=testsmallbatch -v -timeout 20m -p $(TEST_PARALLEL_PACKAGES) -parallel=$(TEST_PARALLEL_TESTS)

 # The most common use is to set TEST_COUNT=1 to avoid Go's test cache.
 ifdef TEST_COUNT
@@ -1068,13 +1313,40 @@ endif
 TEST_PACKAGES ?= ./...

 test:
-	$(GIT_FLAGS) gotestsum --format standard-quiet $(GOTESTSUM_RETRY_FLAGS) --packages="$(TEST_PACKAGES)" -- $(GOTEST_FLAGS)
+	$(GIT_FLAGS) gotestsum --format standard-quiet \
+		$(GOTESTSUM_RETRY_FLAGS) \
+		--packages="$(TEST_PACKAGES)" \
+		-- \
+		$(GOTEST_FLAGS)
 .PHONY: test

+test-race: TEST_PARALLEL_PACKAGES := $(RACE_PARALLEL_PACKAGES)
+test-race: TEST_PARALLEL_TESTS := $(RACE_PARALLEL_TESTS)
+test-race:
+	$(GIT_FLAGS) gotestsum --format standard-quiet \
+		--junitfile="gotests.xml" \
+		$(GOTESTSUM_RETRY_FLAGS) \
+		--packages="$(TEST_PACKAGES)" \
+		-- \
+		-race \
+		$(GOTEST_FLAGS)
+.PHONY: test-race
+
 test-cli:
 	$(MAKE) test TEST_PACKAGES="./cli..."
 .PHONY: test-cli

+test-js: site/node_modules/.installed
+	cd site/
+	pnpm test:ci
+.PHONY: test-js
+
+test-storybook: site/node_modules/.installed
+	cd site/
+	pnpm playwright:install
+	pnpm exec vitest run --project=storybook
+.PHONY: test-storybook
+
 # sqlc-cloud-is-setup will fail if no SQLc auth token is set. Use this as a
 # dependency for any sqlc-cloud related targets.
 sqlc-cloud-is-setup:
@@ -1086,37 +1358,22 @@ sqlc-cloud-is-setup:

 sqlc-push: sqlc-cloud-is-setup test-postgres-docker
 	echo "--- sqlc push"
-	SQLC_DATABASE_URL="postgresql://postgres:postgres@localhost:5432/$(shell go run scripts/migrate-ci/main.go)" \
+	SQLC_DATABASE_URL="postgresql://postgres:postgres@localhost:5432/$$(go run scripts/migrate-ci/main.go)" \
 	sqlc push -f coderd/database/sqlc.yaml && echo "Passed sqlc push"
 .PHONY: sqlc-push

 sqlc-verify: sqlc-cloud-is-setup test-postgres-docker
 	echo "--- sqlc verify"
-	SQLC_DATABASE_URL="postgresql://postgres:postgres@localhost:5432/$(shell go run scripts/migrate-ci/main.go)" \
+	SQLC_DATABASE_URL="postgresql://postgres:postgres@localhost:5432/$$(go run scripts/migrate-ci/main.go)" \
 	sqlc verify -f coderd/database/sqlc.yaml && echo "Passed sqlc verify"
 .PHONY: sqlc-verify

 sqlc-vet: test-postgres-docker
 	echo "--- sqlc vet"
-	SQLC_DATABASE_URL="postgresql://postgres:postgres@localhost:5432/$(shell go run scripts/migrate-ci/main.go)" \
+	SQLC_DATABASE_URL="postgresql://postgres:postgres@localhost:5432/$$(go run scripts/migrate-ci/main.go)" \
 	sqlc vet -f coderd/database/sqlc.yaml && echo "Passed sqlc vet"
 .PHONY: sqlc-vet

-# When updating -timeout for this test, keep in sync with
-# test-go-postgres (.github/workflows/coder.yaml).
-# Do add coverage flags so that test caching works.
-test-postgres: test-postgres-docker
-	# The postgres test is prone to failure, so we limit parallelism for
-	# more consistent execution.
-	$(GIT_FLAGS)  gotestsum \
-		--junitfile="gotests.xml" \
-		--jsonfile="gotests.json" \
-		$(GOTESTSUM_RETRY_FLAGS) \
-		--packages="./..." -- \
-		-tags=testsmallbatch \
-		-timeout=20m \
-		-count=1
-.PHONY: test-postgres

 test-migrations: test-postgres-docker
 	echo "--- test migrations"
@@ -1132,13 +1389,24 @@ test-migrations: test-postgres-docker

 # NOTE: we set --memory to the same size as a GitHub runner.
 test-postgres-docker:
+	# If our container is already running, nothing to do.
+	if docker ps --filter "name=test-postgres-docker-${POSTGRES_VERSION}" --format '{{.Names}}' | grep -q .; then \
+		echo "test-postgres-docker-${POSTGRES_VERSION} is already running."; \
+		exit 0; \
+	fi
+	# If something else is on 5432, warn but don't fail.
+	if pg_isready -h 127.0.0.1 -q 2>/dev/null; then \
+		echo "WARNING: PostgreSQL is already running on 127.0.0.1:5432 (not our container)."; \
+		echo "Tests will use this instance. To use the Makefile's container, stop it first."; \
+		exit 0; \
+	fi
 	docker rm -f test-postgres-docker-${POSTGRES_VERSION} || true

 	# Try pulling up to three times to avoid CI flakes.
 	docker pull ${POSTGRES_IMAGE} || {
 		retries=2
-		for try in $(seq 1 ${retries}); do
-			echo "Failed to pull image, retrying (${try}/${retries})..."
+		for try in $$(seq 1 $${retries}); do
+			echo "Failed to pull image, retrying ($${try}/$${retries})..."
 			sleep 1
 			if docker pull ${POSTGRES_IMAGE}; then
 				break
@@ -1179,16 +1447,11 @@ test-postgres-docker:
 		-c log_statement=all
 	while ! pg_isready -h 127.0.0.1
 	do
-		echo "$(date) - waiting for database to start"
+		echo "$$(date) - waiting for database to start"
 		sleep 0.5
 	done
 .PHONY: test-postgres-docker

-# Make sure to keep this in sync with test-go-race from .github/workflows/ci.yaml.
-test-race:
-	$(GIT_FLAGS) gotestsum --junitfile="gotests.xml" -- -tags=testsmallbatch -race -count=1 -parallel 4 -p 4 ./...
-.PHONY: test-race
-
 test-tailnet-integration:
 	env \
 		CODER_TAILNET_TESTS=true \
@@ -1217,6 +1480,7 @@ site/e2e/bin/coder: go.mod go.sum $(GO_SRC_FILES)

 test-e2e: site/e2e/bin/coder site/node_modules/.installed site/out/index.html
 	cd site/
+	pnpm playwright:install
 ifdef CI
 	DEBUG=pw:api pnpm playwright:test --forbid-only --workers 1
 else
@@ -1231,3 +1495,5 @@ dogfood/coder/nix.hash: flake.nix flake.lock
 count-test-databases:
 	PGPASSWORD=postgres psql -h localhost -U postgres -d coder_testing -P pager=off -c 'SELECT test_package, count(*) as count from test_databases GROUP BY test_package ORDER BY count DESC'
 .PHONY: count-test-databases
+
+.PHONY: count-test-databases
@@ -16,7 +16,6 @@ import (
 	"os/user"
 	"path/filepath"
 	"slices"
-	"sort"
 	"strconv"
 	"strings"
 	"sync"
@@ -41,6 +40,7 @@ import (
 	"github.com/coder/coder/v2/agent/agentcontainers"
 	"github.com/coder/coder/v2/agent/agentexec"
 	"github.com/coder/coder/v2/agent/agentfiles"
+	"github.com/coder/coder/v2/agent/agentgit"
 	"github.com/coder/coder/v2/agent/agentproc"
 	"github.com/coder/coder/v2/agent/agentscripts"
 	"github.com/coder/coder/v2/agent/agentsocket"
@@ -49,6 +49,8 @@ import (
 	"github.com/coder/coder/v2/agent/proto"
 	"github.com/coder/coder/v2/agent/proto/resourcesmonitor"
 	"github.com/coder/coder/v2/agent/reconnectingpty"
+	"github.com/coder/coder/v2/agent/x/agentdesktop"
+	"github.com/coder/coder/v2/agent/x/agentmcp"
 	"github.com/coder/coder/v2/buildinfo"
 	"github.com/coder/coder/v2/cli/gitauth"
 	"github.com/coder/coder/v2/coderd/database/dbtime"
@@ -102,6 +104,7 @@ type Options struct {
 	Execer                       agentexec.Execer
 	Devcontainers                bool
 	DevcontainerAPIOptions       []agentcontainers.Option // Enable Devcontainers for these to be effective.
+	GitAPIOptions                []agentgit.Option
 	Clock                        quartz.Clock
 	SocketServerEnabled          bool
 	SocketPath                   string // Path for the agent socket server socket
@@ -217,6 +220,7 @@ func New(options Options) Agent {

 		devcontainers:              options.Devcontainers,
 		containerAPIOptions:        options.DevcontainerAPIOptions,
+		gitAPIOptions:              options.GitAPIOptions,
 		socketPath:                 options.SocketPath,
 		socketServerEnabled:        options.SocketServerEnabled,
 		boundaryLogProxySocketPath: options.BoundaryLogProxySocketPath,
@@ -302,9 +306,14 @@ type agent struct {
 	devcontainers       bool
 	containerAPIOptions []agentcontainers.Option
 	containerAPI        *agentcontainers.API
+	gitAPIOptions       []agentgit.Option

 	filesAPI   *agentfiles.API
+	gitAPI     *agentgit.API
 	processAPI *agentproc.API
+	desktopAPI *agentdesktop.API
+	mcpManager *agentmcp.Manager
+	mcpAPI     *agentmcp.API

 	socketServerEnabled bool
 	socketPath          string
@@ -376,9 +385,22 @@ func (a *agent) init() {

 	a.containerAPI = agentcontainers.NewAPI(a.logger.Named("containers"), containerAPIOpts...)

-	a.filesAPI = agentfiles.NewAPI(a.logger.Named("files"), a.filesystem)
-	a.processAPI = agentproc.NewAPI(a.logger.Named("processes"), a.execer, a.updateCommandEnv)
-
+	pathStore := agentgit.NewPathStore()
+	a.filesAPI = agentfiles.NewAPI(a.logger.Named("files"), a.filesystem, pathStore)
+	a.processAPI = agentproc.NewAPI(a.logger.Named("processes"), a.execer, a.updateCommandEnv, pathStore, func() string {
+		if m := a.manifest.Load(); m != nil {
+			return m.Directory
+		}
+		return ""
+	})
+	gitOpts := append([]agentgit.Option{agentgit.WithClock(a.clock)}, a.gitAPIOptions...)
+	a.gitAPI = agentgit.NewAPI(a.logger.Named("git"), pathStore, gitOpts...)
+	desktop := agentdesktop.NewPortableDesktop(
+		a.logger.Named("desktop"), a.execer, a.scriptRunner.ScriptBinDir(),
+	)
+	a.desktopAPI = agentdesktop.NewAPI(a.logger.Named("desktop"), desktop, a.clock)
+	a.mcpManager = agentmcp.NewManager(a.logger.Named("mcp"))
+	a.mcpAPI = agentmcp.NewAPI(a.logger.Named("mcp"), a.mcpManager)
 	a.reconnectingPTYServer = reconnectingpty.NewServer(
 		a.logger.Named("reconnecting-pty"),
 		a.sshServer,
@@ -410,7 +432,7 @@ func (a *agent) initSocketServer() {
 		agentsocket.WithPath(a.socketPath),
 	)
 	if err != nil {
-		a.logger.Warn(a.hardCtx, "failed to create socket server", slog.Error(err), slog.F("path", a.socketPath))
+		a.logger.Error(a.hardCtx, "failed to create socket server", slog.Error(err), slog.F("path", a.socketPath))
 		return
 	}

@@ -420,7 +442,12 @@ func (a *agent) initSocketServer() {

 // startBoundaryLogProxyServer starts the boundary log proxy socket server.
 func (a *agent) startBoundaryLogProxyServer() {
-	proxy := boundarylogproxy.NewServer(a.logger, a.boundaryLogProxySocketPath)
+	if a.boundaryLogProxySocketPath == "" {
+		a.logger.Warn(a.hardCtx, "boundary log proxy socket path not defined; not starting proxy")
+		return
+	}
+
+	proxy := boundarylogproxy.NewServer(a.logger, a.boundaryLogProxySocketPath, a.prometheusRegistry)
 	if err := proxy.Start(); err != nil {
 		a.logger.Warn(a.hardCtx, "failed to start boundary log proxy", slog.Error(err))
 		return
@@ -1020,6 +1047,13 @@ func (a *agent) run() (retErr error) {
 		}
 	}()

+	// The socket server accepts requests from processes running inside the workspace and forwards
+	// some of the requests to Coderd over the DRPC connection.
+	if a.socketServer != nil {
+		a.socketServer.SetAgentAPI(aAPI)
+		defer a.socketServer.ClearAgentAPI()
+	}
+
 	// A lot of routines need the agent API / tailnet API connection.  We run them in their own
 	// goroutines in parallel, but errors in any routine will cause them all to exit so we can
 	// redial the coder server and retry.
@@ -1319,6 +1353,14 @@ func (a *agent) handleManifest(manifestOK *checkpoint) func(ctx context.Context,
 				}
 				a.metrics.startupScriptSeconds.WithLabelValues(label).Set(dur)
 				a.scriptRunner.StartCron()
+
+				// Connect to workspace MCP servers after the
+				// lifecycle transition to avoid delaying Ready.
+				// This runs inside the tracked goroutine so it
+				// is properly awaited on shutdown.
+				if mcpErr := a.mcpManager.Connect(a.gracefulCtx, manifest.Directory); mcpErr != nil {
+					a.logger.Warn(ctx, "failed to connect to workspace MCP servers", slog.Error(mcpErr))
+				}
 			})
 			if err != nil {
 				return xerrors.Errorf("track conn goroutine: %w", err)
@@ -1847,7 +1889,7 @@ func (a *agent) Collect(ctx context.Context, networkStats map[netlogtype.Connect
 		}()
 	}
 	wg.Wait()
-	sort.Float64s(durations)
+	slices.Sort(durations)
 	durationsLength := len(durations)
 	switch {
 	case durationsLength == 0:
@@ -2037,6 +2079,14 @@ func (a *agent) Close() error {
 		a.logger.Error(a.hardCtx, "process API close", slog.Error(err))
 	}

+	if err := a.desktopAPI.Close(); err != nil {
+		a.logger.Error(a.hardCtx, "desktop API close", slog.Error(err))
+	}
+
+	if err := a.mcpManager.Close(); err != nil {
+		a.logger.Error(a.hardCtx, "mcp manager close", slog.Error(err))
+	}
+
 	if a.boundaryLogProxy != nil {
 		err = a.boundaryLogProxy.Close()
 		if err != nil {
@@ -713,15 +713,15 @@ func TestAgent_Session_TTY_MOTD_Update(t *testing.T) {
 		},
 	}

-	ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
-	defer cancel()
-
 	setSBInterval := func(_ *agenttest.Client, opts *agent.Options) {
-		opts.ServiceBannerRefreshInterval = 5 * time.Millisecond
+		opts.ServiceBannerRefreshInterval = testutil.IntervalFast
 	}
 	//nolint:dogsled // Allow the blank identifiers.
 	conn, client, _, _, _ := setupAgent(t, agentsdk.Manifest{}, 0, setSBInterval)

+	ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
+	defer cancel()
+
 	//nolint:paralleltest // These tests need to swap the banner func.
 	for _, port := range sshPorts {
 		sshClient, err := conn.SSHClientOnPort(ctx, port)
@@ -733,7 +733,10 @@ func TestAgent_Session_TTY_MOTD_Update(t *testing.T) {
 		for i, test := range tests {
 			t.Run(fmt.Sprintf("(:%d)/%d", port, i), func(t *testing.T) {
 				// Set new banner func and wait for the agent to call it to update the
-				// banner.
+				// banner. We wait for two calls to ensure the value has been stored:
+				// the second call can only begin after the first iteration of
+				// fetchServiceBannerLoop completes (call + store), so after
+				// receiving two signals at least one store has happened.
 				ready := make(chan struct{}, 2)
 				client.SetAnnouncementBannersFunc(func() ([]codersdk.BannerConfig, error) {
 					select {
@@ -742,8 +745,8 @@ func TestAgent_Session_TTY_MOTD_Update(t *testing.T) {
 					}
 					return []codersdk.BannerConfig{test.banner}, nil
 				})
-				<-ready
-				<-ready // Wait for two updates to ensure the value has propagated.
+				testutil.TryReceive(ctx, t, ready)
+				testutil.TryReceive(ctx, t, ready)

 				session, err := sshClient.NewSession()
 				require.NoError(t, err)
@@ -3040,6 +3043,62 @@ func TestAgent_Reconnect(t *testing.T) {
 	closer.Close()
 }

+func TestAgent_ReconnectNoLifecycleReemit(t *testing.T) {
+	t.Parallel()
+	ctx := testutil.Context(t, testutil.WaitLong)
+	logger := testutil.Logger(t)
+
+	fCoordinator := tailnettest.NewFakeCoordinator()
+	agentID := uuid.New()
+	statsCh := make(chan *proto.Stats, 50)
+	derpMap, _ := tailnettest.RunDERPAndSTUN(t)
+
+	client := agenttest.NewClient(t,
+		logger,
+		agentID,
+		agentsdk.Manifest{
+			DERPMap: derpMap,
+			Scripts: []codersdk.WorkspaceAgentScript{{
+				Script:     "echo hello",
+				Timeout:    30 * time.Second,
+				RunOnStart: true,
+			}},
+		},
+		statsCh,
+		fCoordinator,
+	)
+	defer client.Close()
+
+	closer := agent.New(agent.Options{
+		Client: client,
+		Logger: logger.Named("agent"),
+	})
+	defer closer.Close()
+
+	// Wait for the agent to reach Ready state.
+	require.Eventually(t, func() bool {
+		return slices.Contains(client.GetLifecycleStates(), codersdk.WorkspaceAgentLifecycleReady)
+	}, testutil.WaitShort, testutil.IntervalFast)
+
+	statesBefore := slices.Clone(client.GetLifecycleStates())
+
+	// Disconnect by closing the coordinator response channel.
+	call1 := testutil.RequireReceive(ctx, t, fCoordinator.CoordinateCalls)
+	close(call1.Resps)
+
+	// Wait for reconnect.
+	testutil.RequireReceive(ctx, t, fCoordinator.CoordinateCalls)
+
+	// Wait for a stats report as a deterministic steady-state proof.
+	testutil.RequireReceive(ctx, t, statsCh)
+
+	statesAfter := client.GetLifecycleStates()
+	require.Equal(t, statesBefore, statesAfter,
+		"lifecycle states should not be re-reported after reconnect")
+
+	closer.Close()
+}
+
 func TestAgent_WriteVSCodeConfigs(t *testing.T) {
 	t.Parallel()
 	logger := testutil.Logger(t)
@@ -3494,8 +3553,17 @@ func testSessionOutput(t *testing.T, session *ssh.Session, expected, unexpected
 	require.NoError(t, err)

 	ptty.WriteLine("exit 0")
-	err = session.Wait()
-	require.NoError(t, err)
+
+	waitErr := make(chan error, 1)
+	go func() {
+		waitErr <- session.Wait()
+	}()
+	select {
+	case err = <-waitErr:
+		require.NoError(t, err)
+	case <-time.After(testutil.WaitLong):
+		require.Fail(t, "timed out waiting for session to exit")
+	}

 	for _, unexpected := range unexpected {
 		require.NotContains(t, stdout.String(), unexpected, "should not show output")
@@ -57,18 +57,26 @@ type fakeContainerCLI struct {
 }

 func (f *fakeContainerCLI) List(_ context.Context) (codersdk.WorkspaceAgentListContainersResponse, error) {
+	f.mu.Lock()
+	defer f.mu.Unlock()
 	return f.containers, f.listErr
 }

 func (f *fakeContainerCLI) DetectArchitecture(_ context.Context, _ string) (string, error) {
+	f.mu.Lock()
+	defer f.mu.Unlock()
 	return f.arch, f.archErr
 }

 func (f *fakeContainerCLI) Copy(ctx context.Context, name, src, dst string) error {
+	f.mu.Lock()
+	defer f.mu.Unlock()
 	return f.copyErr
 }

 func (f *fakeContainerCLI) ExecAs(ctx context.Context, name, user string, args ...string) ([]byte, error) {
+	f.mu.Lock()
+	defer f.mu.Unlock()
 	return nil, f.execErr
 }

@@ -2689,7 +2697,9 @@ func TestAPI(t *testing.T) {

 		// When: The container is recreated (new container ID) with config changes.
 		terraformContainer.ID = "new-container-id"
+		fCCLI.mu.Lock()
 		fCCLI.containers.Containers = []codersdk.WorkspaceAgentContainer{terraformContainer}
+		fCCLI.mu.Unlock()
 		fDCCLI.upID = terraformContainer.ID
 		fDCCLI.readConfig.MergedConfiguration.Customizations.Coder = []agentcontainers.CoderCustomization{{
 			Apps: []agentcontainers.SubAgentApp{{Slug: "app2"}}, // Changed app triggers recreation logic.
@@ -2821,7 +2831,9 @@ func TestAPI(t *testing.T) {
 		// Simulate container rebuild: new container ID, changed display apps.
 		newContainerID := "new-container-id"
 		terraformContainer.ID = newContainerID
+		fCCLI.mu.Lock()
 		fCCLI.containers.Containers = []codersdk.WorkspaceAgentContainer{terraformContainer}
+		fCCLI.mu.Unlock()
 		fDCCLI.upID = newContainerID
 		fDCCLI.readConfig.MergedConfiguration.Customizations.Coder = []agentcontainers.CoderCustomization{{
 			DisplayApps: map[codersdk.DisplayApp]bool{
@@ -4926,9 +4938,11 @@ func TestDevcontainerPrebuildSupport(t *testing.T) {
 	)
 	api.Start()

+	fCCLI.mu.Lock()
 	fCCLI.containers = codersdk.WorkspaceAgentListContainersResponse{
 		Containers: []codersdk.WorkspaceAgentContainer{testContainer},
 	}
+	fCCLI.mu.Unlock()

 	// Given: We allow the dev container to be created.
 	fDCCLI.upID = testContainer.ID
@@ -433,7 +433,7 @@ func convertDockerInspect(raw []byte) ([]codersdk.WorkspaceAgentContainer, []str
 		}
 		portKeys := maps.Keys(in.NetworkSettings.Ports)
 		// Sort the ports for deterministic output.
-		sort.Strings(portKeys)
+		slices.Sort(portKeys)
 		// If we see the same port bound to both ipv4 and ipv6 loopback or unspecified
 		// interfaces to the same container port, there is no point in adding it multiple times.
 		loopbackHostPortContainerPorts := make(map[int]uint16, 0)
@@ -159,7 +159,6 @@ func TestConvertDockerVolume(t *testing.T) {
 func TestConvertDockerInspect(t *testing.T) {
 	t.Parallel()

-	//nolint:paralleltest // variable recapture no longer required
 	for _, tt := range []struct {
 		name        string
 		expect      []codersdk.WorkspaceAgentContainer
@@ -388,7 +387,6 @@ func TestConvertDockerInspect(t *testing.T) {
 			},
 		},
 	} {
-		// nolint:paralleltest // variable recapture no longer required
 		t.Run(tt.name, func(t *testing.T) {
 			t.Parallel()
 			bs, err := os.ReadFile(filepath.Join("testdata", tt.name, "docker_inspect.json"))
@@ -166,7 +166,6 @@ func TestDockerEnvInfoer(t *testing.T) {

 	pool, err := dockertest.NewPool("")
 	require.NoError(t, err, "Could not connect to docker")
-	// nolint:paralleltest // variable recapture no longer required
 	for idx, tt := range []struct {
 		image             string
 		labels            map[string]string
@@ -223,7 +222,6 @@ func TestDockerEnvInfoer(t *testing.T) {
 			expectedUserShell: "/bin/bash",
 		},
 	} {
-		//nolint:paralleltest // variable recapture no longer required
 		t.Run(fmt.Sprintf("#%d", idx), func(t *testing.T) {
 			// Start a container with the given image
 			// and environment variables
@@ -7,18 +7,21 @@ import (
 	"github.com/spf13/afero"

 	"cdr.dev/slog/v3"
+	"github.com/coder/coder/v2/agent/agentgit"
 )

 // API exposes file-related operations performed through the agent.
 type API struct {
 	logger     slog.Logger
 	filesystem afero.Fs
+	pathStore  *agentgit.PathStore
 }

-func NewAPI(logger slog.Logger, filesystem afero.Fs) *API {
+func NewAPI(logger slog.Logger, filesystem afero.Fs, pathStore *agentgit.PathStore) *API {
 	api := &API{
 		logger:     logger,
 		filesystem: filesystem,
+		pathStore:  pathStore,
 	}
 	return api
 }
@@ -13,10 +13,12 @@ import (
 	"strings"
 	"syscall"

+	"github.com/google/uuid"
 	"github.com/spf13/afero"
 	"golang.org/x/xerrors"

 	"cdr.dev/slog/v3"
+	"github.com/coder/coder/v2/agent/agentgit"
 	"github.com/coder/coder/v2/coderd/httpapi"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/codersdk/workspacesdk"
@@ -40,6 +42,14 @@ type ReadFileLinesResponse struct {

 type HTTPResponseCode = int

+// pendingEdit holds the computed result of a file edit, ready to
+// be written to disk.
+type pendingEdit struct {
+	path    string
+	content string
+	mode    os.FileMode
+}
+
 func (api *API) HandleReadFile(rw http.ResponseWriter, r *http.Request) {
 	ctx := r.Context()

@@ -301,6 +311,13 @@ func (api *API) HandleWriteFile(rw http.ResponseWriter, r *http.Request) {
 		return
 	}

+	// Track edited path for git watch.
+	if api.pathStore != nil {
+		if chatID, ancestorIDs, ok := agentgit.ExtractChatContext(r); ok {
+			api.pathStore.AddPaths(append([]uuid.UUID{chatID}, ancestorIDs...), []string{path})
+		}
+	}
+
 	httpapi.Write(ctx, rw, http.StatusOK, codersdk.Response{
 		Message: fmt.Sprintf("Successfully wrote to %q", path),
 	})
@@ -311,8 +328,14 @@ func (api *API) writeFile(ctx context.Context, r *http.Request, path string) (HT
 		return http.StatusBadRequest, xerrors.Errorf("file path must be absolute: %q", path)
 	}

+	resolved, err := api.resolveSymlink(path)
+	if err != nil {
+		return http.StatusInternalServerError, xerrors.Errorf("resolve symlink %q: %w", path, err)
+	}
+	path = resolved
+
 	dir := filepath.Dir(path)
-	err := api.filesystem.MkdirAll(dir, 0o755)
+	err = api.filesystem.MkdirAll(dir, 0o755)
 	if err != nil {
 		status := http.StatusInternalServerError
 		switch {
@@ -324,25 +347,18 @@ func (api *API) writeFile(ctx context.Context, r *http.Request, path string) (HT
 		return status, err
 	}

-	f, err := api.filesystem.Create(path)
-	if err != nil {
-		status := http.StatusInternalServerError
-		switch {
-		case errors.Is(err, os.ErrPermission):
-			status = http.StatusForbidden
-		case errors.Is(err, syscall.EISDIR):
-			status = http.StatusBadRequest
+	// Check if the target already exists so we can preserve its
+	// permissions on the temp file before rename.
+	var mode *os.FileMode
+	if stat, serr := api.filesystem.Stat(path); serr == nil {
+		if stat.IsDir() {
+			return http.StatusBadRequest, xerrors.Errorf("open %s: is a directory", path)
 		}
-		return status, err
-	}
-	defer f.Close()
-
-	_, err = io.Copy(f, r.Body)
-	if err != nil && !errors.Is(err, io.EOF) && ctx.Err() == nil {
-		api.logger.Error(ctx, "workspace agent write file", slog.Error(err))
+		m := stat.Mode()
+		mode = &m
 	}

-	return 0, nil
+	return api.atomicWrite(ctx, path, mode, r.Body)
 }

 func (api *API) HandleEditFiles(rw http.ResponseWriter, r *http.Request) {
@@ -360,17 +376,23 @@ func (api *API) HandleEditFiles(rw http.ResponseWriter, r *http.Request) {
 		return
 	}

+	// Phase 1: compute all edits in memory. If any file fails
+	// (bad path, search miss, permission error), bail before
+	// writing anything.
+	var pending []pendingEdit
 	var combinedErr error
 	status := http.StatusOK
 	for _, edit := range req.Files {
-		s, err := api.editFile(r.Context(), edit.Path, edit.Edits)
-		// Keep the highest response status, so 500 will be preferred over 400, etc.
+		s, p, err := api.prepareFileEdit(edit.Path, edit.Edits)
 		if s > status {
 			status = s
 		}
 		if err != nil {
 			combinedErr = errors.Join(combinedErr, err)
 		}
+		if p != nil {
+			pending = append(pending, *p)
+		}
 	}

 	if combinedErr != nil {
@@ -380,24 +402,57 @@ func (api *API) HandleEditFiles(rw http.ResponseWriter, r *http.Request) {
 		return
 	}

+	// Phase 2: write all files via atomicWrite. A failure here
+	// (e.g. disk full) can leave earlier files committed. True
+	// cross-file atomicity would require filesystem transactions.
+	for _, p := range pending {
+		mode := p.mode
+		s, err := api.atomicWrite(ctx, p.path, &mode, strings.NewReader(p.content))
+		if err != nil {
+			httpapi.Write(ctx, rw, s, codersdk.Response{
+				Message: err.Error(),
+			})
+			return
+		}
+	}
+
+	// Track edited paths for git watch.
+	if api.pathStore != nil {
+		if chatID, ancestorIDs, ok := agentgit.ExtractChatContext(r); ok {
+			filePaths := make([]string, 0, len(req.Files))
+			for _, f := range req.Files {
+				filePaths = append(filePaths, f.Path)
+			}
+			api.pathStore.AddPaths(append([]uuid.UUID{chatID}, ancestorIDs...), filePaths)
+		}
+	}
+
 	httpapi.Write(ctx, rw, http.StatusOK, codersdk.Response{
 		Message: "Successfully edited file(s)",
 	})
 }

-func (api *API) editFile(ctx context.Context, path string, edits []workspacesdk.FileEdit) (int, error) {
+// prepareFileEdit validates, reads, and computes edits for a single
+// file without writing anything to disk.
+func (api *API) prepareFileEdit(path string, edits []workspacesdk.FileEdit) (int, *pendingEdit, error) {
 	if path == "" {
-		return http.StatusBadRequest, xerrors.New("\"path\" is required")
+		return http.StatusBadRequest, nil, xerrors.New("\"path\" is required")
 	}

 	if !filepath.IsAbs(path) {
-		return http.StatusBadRequest, xerrors.Errorf("file path must be absolute: %q", path)
+		return http.StatusBadRequest, nil, xerrors.Errorf("file path must be absolute: %q", path)
 	}

 	if len(edits) == 0 {
-		return http.StatusBadRequest, xerrors.New("must specify at least one edit")
+		return http.StatusBadRequest, nil, xerrors.New("must specify at least one edit")
 	}

+	resolved, err := api.resolveSymlink(path)
+	if err != nil {
+		return http.StatusInternalServerError, nil, xerrors.Errorf("resolve symlink %q: %w", path, err)
+	}
+	path = resolved
+
 	f, err := api.filesystem.Open(path)
 	if err != nil {
 		status := http.StatusInternalServerError
@@ -407,104 +462,217 @@ func (api *API) editFile(ctx context.Context, path string, edits []workspacesdk.
 		case errors.Is(err, os.ErrPermission):
 			status = http.StatusForbidden
 		}
-		return status, err
+		return status, nil, err
 	}
 	defer f.Close()

 	stat, err := f.Stat()
 	if err != nil {
-		return http.StatusInternalServerError, err
+		return http.StatusInternalServerError, nil, err
 	}

 	if stat.IsDir() {
-		return http.StatusBadRequest, xerrors.Errorf("open %s: not a file", path)
+		return http.StatusBadRequest, nil, xerrors.Errorf("open %s: not a file", path)
 	}

 	data, err := io.ReadAll(f)
 	if err != nil {
-		return http.StatusInternalServerError, xerrors.Errorf("read %s: %w", path, err)
+		return http.StatusInternalServerError, nil, xerrors.Errorf("read %s: %w", path, err)
 	}
 	content := string(data)

 	for _, edit := range edits {
-		var ok bool
-		content, ok = fuzzyReplace(content, edit.Search, edit.Replace)
-		if !ok {
-			api.logger.Warn(ctx, "edit search string not found, skipping",
+		var err error
+		content, err = fuzzyReplace(content, edit)
+		if err != nil {
+			return http.StatusBadRequest, nil, xerrors.Errorf("edit %s: %w", path, err)
+		}
+	}
+
+	return 0, &pendingEdit{
+		path:    path,
+		content: content,
+		mode:    stat.Mode(),
+	}, nil
+}
+
+// atomicWrite writes content from r to path via a temp file in the
+// same directory. If the target exists, its permissions are preserved.
+// On failure the temp file is cleaned up and the original is
+// untouched.
+func (api *API) atomicWrite(ctx context.Context, path string, mode *os.FileMode, r io.Reader) (int, error) {
+	dir := filepath.Dir(path)
+	tmpName := filepath.Join(dir, fmt.Sprintf(".%s.tmp.%s", filepath.Base(path), uuid.New().String()[:8]))
+
+	tmpfile, err := api.filesystem.OpenFile(tmpName, os.O_WRONLY|os.O_CREATE|os.O_EXCL, 0o666)
+	if err != nil {
+		status := http.StatusInternalServerError
+		if errors.Is(err, os.ErrPermission) {
+			status = http.StatusForbidden
+		}
+		return status, err
+	}
+
+	cleanup := func() {
+		if err := api.filesystem.Remove(tmpName); err != nil {
+			api.logger.Warn(ctx, "unable to clean up temp file", slog.Error(err))
+		}
+	}
+
+	_, err = io.Copy(tmpfile, r)
+	if err != nil {
+		_ = tmpfile.Close()
+		cleanup()
+		return http.StatusInternalServerError, xerrors.Errorf("write %s: %w", path, err)
+	}
+
+	// Close before rename to flush buffered data and catch write
+	// errors (e.g. delayed allocation failures).
+	if err := tmpfile.Close(); err != nil {
+		cleanup()
+		return http.StatusInternalServerError, xerrors.Errorf("write %s: %w", path, err)
+	}
+
+	// Set permissions on the temp file before rename so there is
+	// no window where the target has wrong permissions.
+	if mode != nil {
+		if err := api.filesystem.Chmod(tmpName, *mode); err != nil {
+			api.logger.Warn(ctx, "unable to set file permissions",
 				slog.F("path", path),
-				slog.F("search_preview", truncate(edit.Search, 64)),
+				slog.Error(err),
 			)
 		}
 	}

-	// Create an adjacent file to ensure it will be on the same device and can be
-	// moved atomically.
-	tmpfile, err := afero.TempFile(api.filesystem, filepath.Dir(path), filepath.Base(path))
-	if err != nil {
-		return http.StatusInternalServerError, err
-	}
-	defer tmpfile.Close()
-
-	if _, err := tmpfile.Write([]byte(content)); err != nil {
-		if rerr := api.filesystem.Remove(tmpfile.Name()); rerr != nil {
-			api.logger.Warn(ctx, "unable to clean up temp file", slog.Error(rerr))
+	if err := api.filesystem.Rename(tmpName, path); err != nil {
+		cleanup()
+		status := http.StatusInternalServerError
+		if errors.Is(err, os.ErrPermission) {
+			status = http.StatusForbidden
 		}
-		return http.StatusInternalServerError, xerrors.Errorf("edit %s: %w", path, err)
-	}
-
-	err = api.filesystem.Rename(tmpfile.Name(), path)
-	if err != nil {
-		return http.StatusInternalServerError, err
+		return status, xerrors.Errorf("write %s: %w", path, err)
 	}

 	return 0, nil
 }

-// fuzzyReplace attempts to find `search` inside `content` and replace its first
-// occurrence with `replace`. It uses a cascading match strategy inspired by
+// resolveSymlink resolves a path through any symlinks so that
+// subsequent operations (such as atomic rename) target the real
+// file instead of replacing the symlink itself.
+//
+// The filesystem must implement afero.Lstater and afero.LinkReader
+// for resolution to occur; if it does not (e.g. MemMapFs), the
+// path is returned unchanged.
+func (api *API) resolveSymlink(path string) (string, error) {
+	const maxDepth = 10
+
+	lstater, hasLstat := api.filesystem.(afero.Lstater)
+	if !hasLstat {
+		return path, nil
+	}
+	reader, hasReadlink := api.filesystem.(afero.LinkReader)
+	if !hasReadlink {
+		return path, nil
+	}
+
+	for range maxDepth {
+		info, _, err := lstater.LstatIfPossible(path)
+		if err != nil {
+			// If the file does not exist yet (new file write),
+			// there is nothing to resolve.
+			if errors.Is(err, os.ErrNotExist) {
+				return path, nil
+			}
+			return "", err
+		}
+		if info.Mode()&os.ModeSymlink == 0 {
+			return path, nil
+		}
+
+		target, err := reader.ReadlinkIfPossible(path)
+		if err != nil {
+			return "", err
+		}
+		if !filepath.IsAbs(target) {
+			target = filepath.Join(filepath.Dir(path), target)
+		}
+		path = target
+	}
+
+	return "", xerrors.Errorf("too many levels of symlinks resolving %q", path)
+}
+
+// fuzzyReplace attempts to find `search` inside `content` and replace it
+// with `replace`. It uses a cascading match strategy inspired by
 // openai/codex's apply_patch:
 //
 //  1. Exact substring match (byte-for-byte).
 //  2. Line-by-line match ignoring trailing whitespace on each line.
-//  3. Line-by-line match ignoring all leading/trailing whitespace (indentation-tolerant).
+//  3. Line-by-line match ignoring all leading/trailing whitespace
+//     (indentation-tolerant).
 //
-// When a fuzzy match is found (passes 2 or 3), the replacement is still applied
-// at the byte offsets of the original content so that surrounding text (including
-// indentation of untouched lines) is preserved.
+// When edit.ReplaceAll is false (the default), the search string must
+// match exactly one location. If multiple matches are found, an error
+// is returned asking the caller to include more context or set
+// replace_all.
 //
-// Returns the (possibly modified) content and a bool indicating whether a match
-// was found.
-func fuzzyReplace(content, search, replace string) (string, bool) {
-	// Pass 1 – exact substring (replace all occurrences).
+// When a fuzzy match is found (passes 2 or 3), the replacement is still
+// applied at the byte offsets of the original content so that surrounding
+// text (including indentation of untouched lines) is preserved.
+func fuzzyReplace(content string, edit workspacesdk.FileEdit) (string, error) {
+	search := edit.Search
+	replace := edit.Replace
+
+	// Pass 1 – exact substring match.
 	if strings.Contains(content, search) {
-		return strings.ReplaceAll(content, search, replace), true
+		if edit.ReplaceAll {
+			return strings.ReplaceAll(content, search, replace), nil
+		}
+		count := strings.Count(content, search)
+		if count > 1 {
+			return "", xerrors.Errorf("search string matches %d occurrences "+
+				"(expected exactly 1). Include more surrounding "+
+				"context to make the match unique, or set "+
+				"replace_all to true", count)
+		}
+		// Exactly one match.
+		return strings.Replace(content, search, replace, 1), nil
 	}

-	// For line-level fuzzy matching we split both content and search into lines.
+	// For line-level fuzzy matching we split both content and search
+	// into lines.
 	contentLines := strings.SplitAfter(content, "\n")
 	searchLines := strings.SplitAfter(search, "\n")

-	// A trailing newline in the search produces an empty final element from
-	// SplitAfter.  Drop it so it doesn't interfere with line matching.
+	// A trailing newline in the search produces an empty final element
+	// from SplitAfter. Drop it so it doesn't interfere with line
+	// matching.
 	if len(searchLines) > 0 && searchLines[len(searchLines)-1] == "" {
 		searchLines = searchLines[:len(searchLines)-1]
 	}

-	// Pass 2 – trim trailing whitespace on each line.
-	if start, end, ok := seekLines(contentLines, searchLines, func(a, b string) bool {
+	trimRight := func(a, b string) bool {
 		return strings.TrimRight(a, " \t\r\n") == strings.TrimRight(b, " \t\r\n")
-	}); ok {
-		return spliceLines(contentLines, start, end, replace), true
 	}
-
-	// Pass 3 – trim all leading and trailing whitespace (indentation-tolerant).
-	if start, end, ok := seekLines(contentLines, searchLines, func(a, b string) bool {
+	trimAll := func(a, b string) bool {
 		return strings.TrimSpace(a) == strings.TrimSpace(b)
-	}); ok {
-		return spliceLines(contentLines, start, end, replace), true
 	}

-	return content, false
+	// Pass 2 – trim trailing whitespace on each line.
+	if result, matched, err := fuzzyReplaceLines(contentLines, searchLines, replace, trimRight, edit.ReplaceAll); matched {
+		return result, err
+	}
+
+	// Pass 3 – trim all leading and trailing whitespace
+	// (indentation-tolerant). The replacement is inserted verbatim;
+	// callers must provide correctly indented replacement text.
+	if result, matched, err := fuzzyReplaceLines(contentLines, searchLines, replace, trimAll, edit.ReplaceAll); matched {
+		return result, err
+	}
+
+	return "", xerrors.New("search string not found in file. Verify the search " +
+		"string matches the file content exactly, including whitespace " +
+		"and indentation")
 }

 // seekLines scans contentLines looking for a contiguous subsequence that matches
@@ -529,6 +697,26 @@ outer:
 	return 0, 0, false
 }

+// countLineMatches counts how many non-overlapping contiguous
+// subsequences of contentLines match searchLines according to eq.
+func countLineMatches(contentLines, searchLines []string, eq func(a, b string) bool) int {
+	count := 0
+	if len(searchLines) == 0 || len(searchLines) > len(contentLines) {
+		return count
+	}
+outer:
+	for i := 0; i <= len(contentLines)-len(searchLines); i++ {
+		for j, sLine := range searchLines {
+			if !eq(contentLines[i+j], sLine) {
+				continue outer
+			}
+		}
+		count++
+		i += len(searchLines) - 1 // skip past this match
+	}
+	return count
+}
+
 // spliceLines replaces contentLines[start:end] with replacement text, returning
 // the full content as a single string.
 func spliceLines(contentLines []string, start, end int, replacement string) string {
@@ -543,9 +731,71 @@ func spliceLines(contentLines []string, start, end int, replacement string) stri
 	return b.String()
 }

-func truncate(s string, n int) string {
-	if len(s) <= n {
-		return s
+// fuzzyReplaceLines handles fuzzy matching passes (2 and 3) for
+// fuzzyReplace. When replaceAll is false and there are multiple
+// matches, an error is returned. When replaceAll is true, all
+// non-overlapping matches are replaced.
+//
+// Returns (result, true, nil) on success, ("", false, nil) when
+// searchLines don't match at all, or ("", true, err) when the match
+// is ambiguous.
+//
+//nolint:revive // replaceAll is a direct pass-through of the user's flag, not a control coupling.
+func fuzzyReplaceLines(
+	contentLines, searchLines []string,
+	replace string,
+	eq func(a, b string) bool,
+	replaceAll bool,
+) (string, bool, error) {
+	start, end, ok := seekLines(contentLines, searchLines, eq)
+	if !ok {
+		return "", false, nil
 	}
-	return s[:n] + "..."
+
+	if !replaceAll {
+		if count := countLineMatches(contentLines, searchLines, eq); count > 1 {
+			return "", true, xerrors.Errorf("search string matches %d occurrences "+
+				"(expected exactly 1). Include more surrounding "+
+				"context to make the match unique, or set "+
+				"replace_all to true", count)
+		}
+		return spliceLines(contentLines, start, end, replace), true, nil
+	}
+
+	// Replace all: collect all match positions, then apply from last
+	// to first to preserve indices.
+	type lineMatch struct{ start, end int }
+	var matches []lineMatch
+	for i := 0; i <= len(contentLines)-len(searchLines); {
+		found := true
+		for j, sLine := range searchLines {
+			if !eq(contentLines[i+j], sLine) {
+				found = false
+				break
+			}
+		}
+		if found {
+			matches = append(matches, lineMatch{i, i + len(searchLines)})
+			i += len(searchLines) // skip past this match
+		} else {
+			i++
+		}
+	}
+
+	// Apply replacements from last to first.
+	repLines := strings.SplitAfter(replace, "\n")
+	for i := len(matches) - 1; i >= 0; i-- {
+		m := matches[i]
+		newLines := make([]string, 0, m.start+len(repLines)+(len(contentLines)-m.end))
+		newLines = append(newLines, contentLines[:m.start]...)
+		newLines = append(newLines, repLines...)
+		newLines = append(newLines, contentLines[m.end:]...)
+		contentLines = newLines
+	}
+
+	var b strings.Builder
+	for _, l := range contentLines {
+		_, _ = b.WriteString(l)
+	}
+	return b.String(), true, nil
 }
@@ -11,9 +11,13 @@ import (
 	"os"
 	"path/filepath"
 	"runtime"
+	"strings"
 	"syscall"
 	"testing"
+	"testing/iotest"

+	"github.com/go-chi/chi/v5"
+	"github.com/google/uuid"
 	"github.com/spf13/afero"
 	"github.com/stretchr/testify/require"
 	"golang.org/x/xerrors"
@@ -21,6 +25,7 @@ import (
 	"cdr.dev/slog/v3"
 	"cdr.dev/slog/v3/sloggers/slogtest"
 	"github.com/coder/coder/v2/agent/agentfiles"
+	"github.com/coder/coder/v2/agent/agentgit"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/codersdk/workspacesdk"
 	"github.com/coder/coder/v2/testutil"
@@ -116,7 +121,7 @@ func TestReadFile(t *testing.T) {
 		}
 		return nil
 	})
-	api := agentfiles.NewAPI(logger, fs)
+	api := agentfiles.NewAPI(logger, fs, nil)

 	dirPath := filepath.Join(tmpdir, "a-directory")
 	err := fs.MkdirAll(dirPath, 0o755)
@@ -296,7 +301,7 @@ func TestWriteFile(t *testing.T) {
 		}
 		return nil
 	})
-	api := agentfiles.NewAPI(logger, fs)
+	api := agentfiles.NewAPI(logger, fs, nil)

 	dirPath := filepath.Join(tmpdir, "directory")
 	err := fs.MkdirAll(dirPath, 0o755)
@@ -395,6 +400,83 @@ func TestWriteFile(t *testing.T) {
 	}
 }

+func TestWriteFile_ReportsIOError(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true}).Leveled(slog.LevelDebug)
+	fs := afero.NewMemMapFs()
+	api := agentfiles.NewAPI(logger, fs, nil)
+
+	tmpdir := os.TempDir()
+	path := filepath.Join(tmpdir, "write-io-error")
+	err := afero.WriteFile(fs, path, []byte("original"), 0o644)
+	require.NoError(t, err)
+
+	ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
+	defer cancel()
+
+	// A reader that always errors simulates a failed body read
+	// (e.g. network interruption). The atomic write should leave
+	// the original file intact.
+	body := iotest.ErrReader(xerrors.New("simulated I/O error"))
+	w := httptest.NewRecorder()
+	r := httptest.NewRequestWithContext(ctx, http.MethodPost,
+		fmt.Sprintf("/write-file?path=%s", path), body)
+	api.Routes().ServeHTTP(w, r)
+
+	require.Equal(t, http.StatusInternalServerError, w.Code)
+	got := &codersdk.Error{}
+	err = json.NewDecoder(w.Body).Decode(got)
+	require.NoError(t, err)
+	require.ErrorContains(t, got, "simulated I/O error")
+
+	// The original file must survive the failed write.
+	data, err := afero.ReadFile(fs, path)
+	require.NoError(t, err)
+	require.Equal(t, "original", string(data))
+}
+
+func TestWriteFile_PreservesPermissions(t *testing.T) {
+	t.Parallel()
+
+	if runtime.GOOS == "windows" {
+		t.Skip("file permissions are not reliably supported on Windows")
+	}
+
+	dir := t.TempDir()
+	logger := slogtest.Make(t, nil).Leveled(slog.LevelDebug)
+	osFs := afero.NewOsFs()
+	api := agentfiles.NewAPI(logger, osFs, nil)
+
+	path := filepath.Join(dir, "script.sh")
+	err := afero.WriteFile(osFs, path, []byte("#!/bin/sh\necho hello\n"), 0o755)
+	require.NoError(t, err)
+
+	info, err := osFs.Stat(path)
+	require.NoError(t, err)
+	require.Equal(t, os.FileMode(0o755), info.Mode().Perm())
+
+	ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
+	defer cancel()
+
+	// Overwrite the file with new content.
+	w := httptest.NewRecorder()
+	r := httptest.NewRequestWithContext(ctx, http.MethodPost,
+		fmt.Sprintf("/write-file?path=%s", path),
+		bytes.NewReader([]byte("#!/bin/sh\necho world\n")))
+	api.Routes().ServeHTTP(w, r)
+	require.Equal(t, http.StatusOK, w.Code)
+
+	data, err := afero.ReadFile(osFs, path)
+	require.NoError(t, err)
+	require.Equal(t, "#!/bin/sh\necho world\n", string(data))
+
+	info, err = osFs.Stat(path)
+	require.NoError(t, err)
+	require.Equal(t, os.FileMode(0o755), info.Mode().Perm(),
+		"write_file should preserve the original file's permissions")
+}
+
 func TestEditFiles(t *testing.T) {
 	t.Parallel()

@@ -414,7 +496,7 @@ func TestEditFiles(t *testing.T) {
 		}
 		return nil
 	})
-	api := agentfiles.NewAPI(logger, fs)
+	api := agentfiles.NewAPI(logger, fs, nil)

 	dirPath := filepath.Join(tmpdir, "directory")
 	err := fs.MkdirAll(dirPath, 0o755)
@@ -554,6 +636,8 @@ func TestEditFiles(t *testing.T) {
 			},
 			errCode: http.StatusInternalServerError,
 			errors:  []string{"rename failed"},
+			// Original file must survive the failed rename.
+			expected: map[string]string{failRenameFilePath: "foo bar"},
 		},
 		{
 			name:     "Edit1",
@@ -572,7 +656,9 @@ func TestEditFiles(t *testing.T) {
 			expected: map[string]string{filepath.Join(tmpdir, "edit1"): "bar bar"},
 		},
 		{
-			name:     "EditEdit", // Edits affect previous edits.
+			// When the second edit creates ambiguity (two "bar"
+			// occurrences), it should fail.
+			name:     "EditEditAmbiguous",
 			contents: map[string]string{filepath.Join(tmpdir, "edit-edit"): "foo bar"},
 			edits: []workspacesdk.FileEdits{
 				{
@@ -589,7 +675,33 @@ func TestEditFiles(t *testing.T) {
 					},
 				},
 			},
-			expected: map[string]string{filepath.Join(tmpdir, "edit-edit"): "qux qux"},
+			errCode: http.StatusBadRequest,
+			errors:  []string{"matches 2 occurrences"},
+			// File should not be modified on error.
+			expected: map[string]string{filepath.Join(tmpdir, "edit-edit"): "foo bar"},
+		},
+		{
+			// With replace_all the cascading edit replaces
+			// both occurrences.
+			name:     "EditEditReplaceAll",
+			contents: map[string]string{filepath.Join(tmpdir, "edit-edit-ra"): "foo bar"},
+			edits: []workspacesdk.FileEdits{
+				{
+					Path: filepath.Join(tmpdir, "edit-edit-ra"),
+					Edits: []workspacesdk.FileEdit{
+						{
+							Search:  "foo",
+							Replace: "bar",
+						},
+						{
+							Search:     "bar",
+							Replace:    "qux",
+							ReplaceAll: true,
+						},
+					},
+				},
+			},
+			expected: map[string]string{filepath.Join(tmpdir, "edit-edit-ra"): "qux qux"},
 		},
 		{
 			name:     "Multiline",
@@ -716,7 +828,7 @@ func TestEditFiles(t *testing.T) {
 			expected: map[string]string{filepath.Join(tmpdir, "exact-preferred"): "goodbye world"},
 		},
 		{
-			name:     "NoMatchStillSucceeds",
+			name:     "NoMatchErrors",
 			contents: map[string]string{filepath.Join(tmpdir, "no-match"): "original content"},
 			edits: []workspacesdk.FileEdits{
 				{
@@ -729,9 +841,83 @@ func TestEditFiles(t *testing.T) {
 					},
 				},
 			},
+			errCode: http.StatusBadRequest,
+			errors:  []string{"search string not found in file"},
 			// File should remain unchanged.
 			expected: map[string]string{filepath.Join(tmpdir, "no-match"): "original content"},
 		},
+		{
+			name:     "AmbiguousExactMatch",
+			contents: map[string]string{filepath.Join(tmpdir, "ambig-exact"): "foo bar foo baz foo"},
+			edits: []workspacesdk.FileEdits{
+				{
+					Path: filepath.Join(tmpdir, "ambig-exact"),
+					Edits: []workspacesdk.FileEdit{
+						{
+							Search:  "foo",
+							Replace: "qux",
+						},
+					},
+				},
+			},
+			errCode:  http.StatusBadRequest,
+			errors:   []string{"matches 3 occurrences"},
+			expected: map[string]string{filepath.Join(tmpdir, "ambig-exact"): "foo bar foo baz foo"},
+		},
+		{
+			name:     "ReplaceAllExact",
+			contents: map[string]string{filepath.Join(tmpdir, "ra-exact"): "foo bar foo baz foo"},
+			edits: []workspacesdk.FileEdits{
+				{
+					Path: filepath.Join(tmpdir, "ra-exact"),
+					Edits: []workspacesdk.FileEdit{
+						{
+							Search:     "foo",
+							Replace:    "qux",
+							ReplaceAll: true,
+						},
+					},
+				},
+			},
+			expected: map[string]string{filepath.Join(tmpdir, "ra-exact"): "qux bar qux baz qux"},
+		},
+		{
+			// replace_all with fuzzy trailing-whitespace match.
+			name:     "ReplaceAllFuzzyTrailing",
+			contents: map[string]string{filepath.Join(tmpdir, "ra-fuzzy-trail"): "hello   \nworld\nhello   \nagain"},
+			edits: []workspacesdk.FileEdits{
+				{
+					Path: filepath.Join(tmpdir, "ra-fuzzy-trail"),
+					Edits: []workspacesdk.FileEdit{
+						{
+							Search:     "hello\n",
+							Replace:    "bye\n",
+							ReplaceAll: true,
+						},
+					},
+				},
+			},
+			expected: map[string]string{filepath.Join(tmpdir, "ra-fuzzy-trail"): "bye\nworld\nbye\nagain"},
+		},
+		{
+			// replace_all with fuzzy indent match (pass 3).
+			name:     "ReplaceAllFuzzyIndent",
+			contents: map[string]string{filepath.Join(tmpdir, "ra-fuzzy-indent"): "\t\talpha\n\t\tbeta\n\t\talpha\n\t\tgamma"},
+			edits: []workspacesdk.FileEdits{
+				{
+					Path: filepath.Join(tmpdir, "ra-fuzzy-indent"),
+					Edits: []workspacesdk.FileEdit{
+						{
+							// Search uses different indentation (spaces instead of tabs).
+							Search:     "    alpha\n",
+							Replace:    "\t\tREPLACED\n",
+							ReplaceAll: true,
+						},
+					},
+				},
+			},
+			expected: map[string]string{filepath.Join(tmpdir, "ra-fuzzy-indent"): "\t\tREPLACED\n\t\tbeta\n\t\tREPLACED\n\t\tgamma"},
+		},
 		{
 			name:     "MixedWhitespaceMultiline",
 			contents: map[string]string{filepath.Join(tmpdir, "mixed-ws"): "func main() {\n\tresult := compute()\n\tfmt.Println(result)\n}"},
@@ -783,8 +969,10 @@ func TestEditFiles(t *testing.T) {
 					},
 				},
 			},
+			// No files should be modified when any edit fails
+			// (atomic multi-file semantics).
 			expected: map[string]string{
-				filepath.Join(tmpdir, "file8"): "edited8 8",
+				filepath.Join(tmpdir, "file8"): "file 8",
 			},
 			// Higher status codes will override lower ones, so in this case the 404
 			// takes priority over the 403.
@@ -794,8 +982,44 @@ func TestEditFiles(t *testing.T) {
 				"file9: file does not exist",
 			},
 		},
+		{
+			// Valid edits on files A and C, but file B has a
+			// search miss. None should be written.
+			name: "AtomicMultiFile_OneFailsNoneWritten",
+			contents: map[string]string{
+				filepath.Join(tmpdir, "atomic-a"): "aaa",
+				filepath.Join(tmpdir, "atomic-b"): "bbb",
+				filepath.Join(tmpdir, "atomic-c"): "ccc",
+			},
+			edits: []workspacesdk.FileEdits{
+				{
+					Path: filepath.Join(tmpdir, "atomic-a"),
+					Edits: []workspacesdk.FileEdit{
+						{Search: "aaa", Replace: "AAA"},
+					},
+				},
+				{
+					Path: filepath.Join(tmpdir, "atomic-b"),
+					Edits: []workspacesdk.FileEdit{
+						{Search: "NOTFOUND", Replace: "XXX"},
+					},
+				},
+				{
+					Path: filepath.Join(tmpdir, "atomic-c"),
+					Edits: []workspacesdk.FileEdit{
+						{Search: "ccc", Replace: "CCC"},
+					},
+				},
+			},
+			errCode: http.StatusBadRequest,
+			errors:  []string{"search string not found"},
+			expected: map[string]string{
+				filepath.Join(tmpdir, "atomic-a"): "aaa",
+				filepath.Join(tmpdir, "atomic-b"): "bbb",
+				filepath.Join(tmpdir, "atomic-c"): "ccc",
+			},
+		},
 	}
-
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {
 			t.Parallel()
@@ -838,6 +1062,230 @@ func TestEditFiles(t *testing.T) {
 	}
 }

+func TestEditFiles_PreservesPermissions(t *testing.T) {
+	t.Parallel()
+
+	if runtime.GOOS == "windows" {
+		t.Skip("file permissions are not reliably supported on Windows")
+	}
+
+	dir := t.TempDir()
+	logger := slogtest.Make(t, nil).Leveled(slog.LevelDebug)
+	osFs := afero.NewOsFs()
+	api := agentfiles.NewAPI(logger, osFs, nil)
+
+	path := filepath.Join(dir, "script.sh")
+	err := afero.WriteFile(osFs, path, []byte("#!/bin/sh\necho hello\n"), 0o755)
+	require.NoError(t, err)
+
+	// Sanity-check the initial mode.
+	info, err := osFs.Stat(path)
+	require.NoError(t, err)
+	require.Equal(t, os.FileMode(0o755), info.Mode().Perm())
+
+	ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
+	defer cancel()
+
+	body := workspacesdk.FileEditRequest{
+		Files: []workspacesdk.FileEdits{
+			{
+				Path: path,
+				Edits: []workspacesdk.FileEdit{
+					{
+						Search:  "hello",
+						Replace: "world",
+					},
+				},
+			},
+		},
+	}
+	buf := bytes.NewBuffer(nil)
+	enc := json.NewEncoder(buf)
+	enc.SetEscapeHTML(false)
+	err = enc.Encode(body)
+	require.NoError(t, err)
+
+	w := httptest.NewRecorder()
+	r := httptest.NewRequestWithContext(ctx, http.MethodPost, "/edit-files", buf)
+	api.Routes().ServeHTTP(w, r)
+	require.Equal(t, http.StatusOK, w.Code)
+
+	// Verify content was updated.
+	data, err := afero.ReadFile(osFs, path)
+	require.NoError(t, err)
+	require.Equal(t, "#!/bin/sh\necho world\n", string(data))
+
+	// Verify permissions are preserved after the
+	// temp-file-and-rename cycle.
+	info, err = osFs.Stat(path)
+	require.NoError(t, err)
+	require.Equal(t, os.FileMode(0o755), info.Mode().Perm(),
+		"edit_files should preserve the original file's permissions")
+}
+
+func TestHandleWriteFile_ChatHeaders_UpdatesPathStore(t *testing.T) {
+	t.Parallel()
+
+	pathStore := agentgit.NewPathStore()
+	logger := slogtest.Make(t, nil)
+	fs := afero.NewMemMapFs()
+	api := agentfiles.NewAPI(logger, fs, pathStore)
+
+	testPath := filepath.Join(os.TempDir(), "test.txt")
+
+	chatID := uuid.New()
+	ancestorID := uuid.New()
+	ancestorJSON, _ := json.Marshal([]string{ancestorID.String()})
+
+	body := strings.NewReader("hello world")
+	req := httptest.NewRequest(http.MethodPost, "/write-file?path="+testPath, body)
+	req.Header.Set(workspacesdk.CoderChatIDHeader, chatID.String())
+	req.Header.Set(workspacesdk.CoderAncestorChatIDsHeader, string(ancestorJSON))
+
+	rr := httptest.NewRecorder()
+	r := chi.NewRouter()
+	r.Post("/write-file", api.HandleWriteFile)
+	r.ServeHTTP(rr, req)
+
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Verify PathStore was updated for both chat and ancestor.
+	paths := pathStore.GetPaths(chatID)
+	require.Equal(t, []string{testPath}, paths)
+
+	ancestorPaths := pathStore.GetPaths(ancestorID)
+	require.Equal(t, []string{testPath}, ancestorPaths)
+}
+
+func TestHandleWriteFile_NoChatHeaders_NoPathStoreUpdate(t *testing.T) {
+	t.Parallel()
+
+	pathStore := agentgit.NewPathStore()
+	logger := slogtest.Make(t, nil)
+	fs := afero.NewMemMapFs()
+	api := agentfiles.NewAPI(logger, fs, pathStore)
+
+	testPath := filepath.Join(os.TempDir(), "test.txt")
+
+	body := strings.NewReader("hello world")
+	req := httptest.NewRequest(http.MethodPost, "/write-file?path="+testPath, body)
+
+	rr := httptest.NewRecorder()
+	r := chi.NewRouter()
+	r.Post("/write-file", api.HandleWriteFile)
+	r.ServeHTTP(rr, req)
+
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// PathStore should be globally empty since no chat headers were set.
+	require.Equal(t, 0, pathStore.Len())
+}
+
+func TestHandleWriteFile_Failure_NoPathStoreUpdate(t *testing.T) {
+	t.Parallel()
+
+	pathStore := agentgit.NewPathStore()
+	logger := slogtest.Make(t, nil)
+	fs := afero.NewMemMapFs()
+	api := agentfiles.NewAPI(logger, fs, pathStore)
+
+	chatID := uuid.New()
+
+	// Write to a relative path (should fail with 400).
+	body := strings.NewReader("hello world")
+	req := httptest.NewRequest(http.MethodPost, "/write-file?path=relative/path.txt", body)
+	req.Header.Set(workspacesdk.CoderChatIDHeader, chatID.String())
+
+	rr := httptest.NewRecorder()
+	r := chi.NewRouter()
+	r.Post("/write-file", api.HandleWriteFile)
+	r.ServeHTTP(rr, req)
+
+	require.Equal(t, http.StatusBadRequest, rr.Code)
+
+	// PathStore should NOT be updated on failure.
+	paths := pathStore.GetPaths(chatID)
+	require.Empty(t, paths)
+}
+
+func TestHandleEditFiles_ChatHeaders_UpdatesPathStore(t *testing.T) {
+	t.Parallel()
+
+	pathStore := agentgit.NewPathStore()
+	logger := slogtest.Make(t, nil)
+	fs := afero.NewMemMapFs()
+	api := agentfiles.NewAPI(logger, fs, pathStore)
+
+	testPath := filepath.Join(os.TempDir(), "test.txt")
+
+	// Create the file first.
+	require.NoError(t, afero.WriteFile(fs, testPath, []byte("hello"), 0o644))
+
+	chatID := uuid.New()
+	editReq := workspacesdk.FileEditRequest{
+		Files: []workspacesdk.FileEdits{
+			{
+				Path: testPath,
+				Edits: []workspacesdk.FileEdit{
+					{Search: "hello", Replace: "world"},
+				},
+			},
+		},
+	}
+	body, _ := json.Marshal(editReq)
+	req := httptest.NewRequest(http.MethodPost, "/edit-files", bytes.NewReader(body))
+	req.Header.Set("Content-Type", "application/json")
+	req.Header.Set(workspacesdk.CoderChatIDHeader, chatID.String())
+
+	rr := httptest.NewRecorder()
+	r := chi.NewRouter()
+	r.Post("/edit-files", api.HandleEditFiles)
+	r.ServeHTTP(rr, req)
+
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	paths := pathStore.GetPaths(chatID)
+	require.Equal(t, []string{testPath}, paths)
+}
+
+func TestHandleEditFiles_Failure_NoPathStoreUpdate(t *testing.T) {
+	t.Parallel()
+
+	pathStore := agentgit.NewPathStore()
+	logger := slogtest.Make(t, nil)
+	fs := afero.NewMemMapFs()
+	api := agentfiles.NewAPI(logger, fs, pathStore)
+
+	chatID := uuid.New()
+
+	// Edit a non-existent file (should fail with 404).
+	editReq := workspacesdk.FileEditRequest{
+		Files: []workspacesdk.FileEdits{
+			{
+				Path: "/nonexistent/file.txt",
+				Edits: []workspacesdk.FileEdit{
+					{Search: "hello", Replace: "world"},
+				},
+			},
+		},
+	}
+	body, _ := json.Marshal(editReq)
+	req := httptest.NewRequest(http.MethodPost, "/edit-files", bytes.NewReader(body))
+	req.Header.Set("Content-Type", "application/json")
+	req.Header.Set(workspacesdk.CoderChatIDHeader, chatID.String())
+
+	rr := httptest.NewRecorder()
+	r := chi.NewRouter()
+	r.Post("/edit-files", api.HandleEditFiles)
+	r.ServeHTTP(rr, req)
+
+	require.NotEqual(t, http.StatusOK, rr.Code)
+
+	// PathStore should NOT be updated on failure.
+	paths := pathStore.GetPaths(chatID)
+	require.Empty(t, paths)
+}
+
 func TestReadFileLines(t *testing.T) {
 	t.Parallel()

@@ -851,7 +1299,7 @@ func TestReadFileLines(t *testing.T) {
 		}
 		return nil
 	})
-	api := agentfiles.NewAPI(logger, fs)
+	api := agentfiles.NewAPI(logger, fs, nil)

 	dirPath := filepath.Join(tmpdir, "a-directory-lines")
 	err := fs.MkdirAll(dirPath, 0o755)
@@ -1022,3 +1470,105 @@ func TestReadFileLines(t *testing.T) {
 		})
 	}
 }
+
+func TestWriteFile_FollowsSymlinks(t *testing.T) {
+	t.Parallel()
+
+	if runtime.GOOS == "windows" {
+		t.Skip("symlinks are not reliably supported on Windows")
+	}
+
+	dir := t.TempDir()
+	logger := slogtest.Make(t, nil).Leveled(slog.LevelDebug)
+	osFs := afero.NewOsFs()
+	api := agentfiles.NewAPI(logger, osFs, nil)
+
+	// Create a real file and a symlink pointing to it.
+	realPath := filepath.Join(dir, "real.txt")
+	err := afero.WriteFile(osFs, realPath, []byte("original"), 0o644)
+	require.NoError(t, err)
+
+	linkPath := filepath.Join(dir, "link.txt")
+	err = os.Symlink(realPath, linkPath)
+	require.NoError(t, err)
+
+	ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
+	defer cancel()
+
+	// Write through the symlink.
+	w := httptest.NewRecorder()
+	r := httptest.NewRequestWithContext(ctx, http.MethodPost,
+		fmt.Sprintf("/write-file?path=%s", linkPath),
+		bytes.NewReader([]byte("updated")))
+	api.Routes().ServeHTTP(w, r)
+	require.Equal(t, http.StatusOK, w.Code)
+
+	// The symlink must still be a symlink.
+	fi, err := os.Lstat(linkPath)
+	require.NoError(t, err)
+	require.NotZero(t, fi.Mode()&os.ModeSymlink, "symlink was replaced")
+
+	// The real file must have the new content.
+	data, err := os.ReadFile(realPath)
+	require.NoError(t, err)
+	require.Equal(t, "updated", string(data))
+}
+
+func TestEditFiles_FollowsSymlinks(t *testing.T) {
+	t.Parallel()
+
+	if runtime.GOOS == "windows" {
+		t.Skip("symlinks are not reliably supported on Windows")
+	}
+
+	dir := t.TempDir()
+	logger := slogtest.Make(t, nil).Leveled(slog.LevelDebug)
+	osFs := afero.NewOsFs()
+	api := agentfiles.NewAPI(logger, osFs, nil)
+
+	// Create a real file and a symlink pointing to it.
+	realPath := filepath.Join(dir, "real.txt")
+	err := afero.WriteFile(osFs, realPath, []byte("hello world"), 0o644)
+	require.NoError(t, err)
+
+	linkPath := filepath.Join(dir, "link.txt")
+	err = os.Symlink(realPath, linkPath)
+	require.NoError(t, err)
+
+	ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
+	defer cancel()
+
+	body := workspacesdk.FileEditRequest{
+		Files: []workspacesdk.FileEdits{
+			{
+				Path: linkPath,
+				Edits: []workspacesdk.FileEdit{
+					{
+						Search:  "hello",
+						Replace: "goodbye",
+					},
+				},
+			},
+		},
+	}
+	buf := bytes.NewBuffer(nil)
+	enc := json.NewEncoder(buf)
+	enc.SetEscapeHTML(false)
+	err = enc.Encode(body)
+	require.NoError(t, err)
+
+	w := httptest.NewRecorder()
+	r := httptest.NewRequestWithContext(ctx, http.MethodPost, "/edit-files", buf)
+	api.Routes().ServeHTTP(w, r)
+	require.Equal(t, http.StatusOK, w.Code)
+
+	// The symlink must still be a symlink.
+	fi, err := os.Lstat(linkPath)
+	require.NoError(t, err)
+	require.NotZero(t, fi.Mode()&os.ModeSymlink, "symlink was replaced")
+
+	// The real file must have the edited content.
+	data, err := os.ReadFile(realPath)
+	require.NoError(t, err)
+	require.Equal(t, "goodbye world", string(data))
+}
@@ -0,0 +1,441 @@
+// Package agentgit provides a WebSocket-based service for watching git
+// repository changes on the agent. It is mounted at /api/v0/git/watch
+// and allows clients to subscribe to file paths, triggering scans of
+// the corresponding git repositories.
+package agentgit
+
+import (
+	"bytes"
+	"context"
+	"os"
+	"os/exec"
+	"path/filepath"
+	"strings"
+	"sync"
+	"time"
+
+	"github.com/dustin/go-humanize"
+	"golang.org/x/xerrors"
+
+	"cdr.dev/slog/v3"
+	"github.com/coder/coder/v2/codersdk"
+	"github.com/coder/quartz"
+)
+
+// Option configures the git watch service.
+type Option func(*Handler)
+
+// WithClock sets a controllable clock for testing. Defaults to
+// quartz.NewReal().
+func WithClock(c quartz.Clock) Option {
+	return func(h *Handler) {
+		h.clock = c
+	}
+}
+
+// WithGitBinary overrides the git binary path (for testing).
+func WithGitBinary(path string) Option {
+	return func(h *Handler) {
+		h.gitBin = path
+	}
+}
+
+const (
+	// scanCooldown is the minimum interval between successive scans.
+	scanCooldown = 1 * time.Second
+	// fallbackPollInterval is the safety-net poll period used when no
+	// filesystem events arrive.
+	fallbackPollInterval = 30 * time.Second
+	// maxTotalDiffSize is the maximum size of the combined
+	// unified diff for an entire repository sent over the wire.
+	// This must stay under the WebSocket message size limit.
+	maxTotalDiffSize = 3 * 1024 * 1024 // 3 MiB
+)
+
+// Handler manages per-connection git watch state.
+type Handler struct {
+	logger slog.Logger
+	clock  quartz.Clock
+	gitBin string // path to git binary; empty means "git" (from PATH)
+
+	mu            sync.Mutex
+	repoRoots     map[string]struct{}     // watched repo roots
+	lastSnapshots map[string]repoSnapshot // last emitted snapshot per repo
+	lastScanAt    time.Time               // when the last scan completed
+	scanTrigger   chan struct{}           // buffered(1), poked by triggers
+}
+
+// repoSnapshot captures the last emitted state for delta comparison.
+type repoSnapshot struct {
+	branch       string
+	remoteOrigin string
+	unifiedDiff  string
+}
+
+// NewHandler creates a new git watch handler.
+func NewHandler(logger slog.Logger, opts ...Option) *Handler {
+	h := &Handler{
+		logger:        logger,
+		clock:         quartz.NewReal(),
+		gitBin:        "git",
+		repoRoots:     make(map[string]struct{}),
+		lastSnapshots: make(map[string]repoSnapshot),
+		scanTrigger:   make(chan struct{}, 1),
+	}
+	for _, opt := range opts {
+		opt(h)
+	}
+
+	// Check if git is available.
+	if _, err := exec.LookPath(h.gitBin); err != nil {
+		h.logger.Warn(context.Background(), "git binary not found, git scanning disabled")
+	}
+
+	return h
+}
+
+// gitAvailable returns true if the configured git binary can be found
+// in PATH.
+func (h *Handler) gitAvailable() bool {
+	_, err := exec.LookPath(h.gitBin)
+	return err == nil
+}
+
+// Subscribe processes a subscribe message, resolving paths to git repo
+// roots and adding new repos to the watch set. Returns true if any new
+// repo roots were added.
+func (h *Handler) Subscribe(paths []string) bool {
+	if !h.gitAvailable() {
+		return false
+	}
+
+	h.mu.Lock()
+	defer h.mu.Unlock()
+
+	added := false
+	for _, p := range paths {
+		if !filepath.IsAbs(p) {
+			continue
+		}
+		p = filepath.Clean(p)
+
+		root, err := findRepoRoot(h.gitBin, p)
+		if err != nil {
+			// Not a git path — silently ignore.
+			continue
+		}
+		if _, ok := h.repoRoots[root]; ok {
+			continue
+		}
+		h.repoRoots[root] = struct{}{}
+		added = true
+	}
+	return added
+}
+
+// RequestScan pokes the scan trigger so the run loop performs a scan.
+func (h *Handler) RequestScan() {
+	select {
+	case h.scanTrigger <- struct{}{}:
+	default:
+		// Already pending.
+	}
+}
+
+// Scan performs a scan of all subscribed repos and computes deltas
+// against the previously emitted snapshots.
+func (h *Handler) Scan(ctx context.Context) *codersdk.WorkspaceAgentGitServerMessage {
+	if !h.gitAvailable() {
+		return nil
+	}
+
+	h.mu.Lock()
+	roots := make([]string, 0, len(h.repoRoots))
+	for r := range h.repoRoots {
+		roots = append(roots, r)
+	}
+	h.mu.Unlock()
+
+	if len(roots) == 0 {
+		return nil
+	}
+
+	now := h.clock.Now().UTC()
+	var repos []codersdk.WorkspaceAgentRepoChanges
+
+	// Perform all I/O outside the lock to avoid blocking
+	// AddPaths/GetPaths/Subscribe callers during disk-heavy scans.
+	type scanResult struct {
+		root    string
+		changes codersdk.WorkspaceAgentRepoChanges
+		err     error
+	}
+	results := make([]scanResult, 0, len(roots))
+	for _, root := range roots {
+		changes, err := getRepoChanges(ctx, h.logger, h.gitBin, root)
+		results = append(results, scanResult{root: root, changes: changes, err: err})
+	}
+
+	// Re-acquire the lock only to commit snapshot updates.
+	h.mu.Lock()
+	defer h.mu.Unlock()
+
+	for _, res := range results {
+		if res.err != nil {
+			if isRepoDeleted(h.gitBin, res.root) {
+				// Repo root or .git directory was removed.
+				// Emit a removal entry, then evict from watch set.
+				removal := codersdk.WorkspaceAgentRepoChanges{
+					RepoRoot: res.root,
+					Removed:  true,
+				}
+				delete(h.repoRoots, res.root)
+				delete(h.lastSnapshots, res.root)
+				repos = append(repos, removal)
+			} else {
+				// Transient error — log and skip without
+				// removing the repo from the watch set.
+				h.logger.Warn(ctx, "scan repo failed",
+					slog.F("root", res.root),
+					slog.Error(res.err),
+				)
+			}
+			continue
+		}
+
+		prev, hasPrev := h.lastSnapshots[res.root]
+		if hasPrev &&
+			prev.branch == res.changes.Branch &&
+			prev.remoteOrigin == res.changes.RemoteOrigin &&
+			prev.unifiedDiff == res.changes.UnifiedDiff {
+			// No change in this repo since last emit.
+			continue
+		}
+
+		// Update snapshot.
+		h.lastSnapshots[res.root] = repoSnapshot{
+			branch:       res.changes.Branch,
+			remoteOrigin: res.changes.RemoteOrigin,
+			unifiedDiff:  res.changes.UnifiedDiff,
+		}
+
+		repos = append(repos, res.changes)
+	}
+
+	h.lastScanAt = now
+
+	if len(repos) == 0 {
+		return nil
+	}
+
+	return &codersdk.WorkspaceAgentGitServerMessage{
+		Type:         codersdk.WorkspaceAgentGitServerMessageTypeChanges,
+		ScannedAt:    &now,
+		Repositories: repos,
+	}
+}
+
+// RunLoop runs the main event loop that listens for refresh requests
+// and fallback poll ticks. It calls scanFn whenever a scan should
+// happen (rate-limited to scanCooldown). It blocks until ctx is
+// canceled.
+func (h *Handler) RunLoop(ctx context.Context, scanFn func()) {
+	fallbackTicker := h.clock.NewTicker(fallbackPollInterval)
+	defer fallbackTicker.Stop()
+
+	for {
+		select {
+		case <-ctx.Done():
+			return
+
+		case <-h.scanTrigger:
+			h.rateLimitedScan(ctx, scanFn)
+
+		case <-fallbackTicker.C:
+			h.rateLimitedScan(ctx, scanFn)
+		}
+	}
+}
+
+func (h *Handler) rateLimitedScan(ctx context.Context, scanFn func()) {
+	h.mu.Lock()
+	elapsed := h.clock.Since(h.lastScanAt)
+	if elapsed < scanCooldown {
+		h.mu.Unlock()
+
+		// Wait for cooldown then scan.
+		remaining := scanCooldown - elapsed
+		timer := h.clock.NewTimer(remaining)
+		defer timer.Stop()
+		select {
+		case <-ctx.Done():
+			return
+		case <-timer.C:
+		}
+
+		scanFn()
+		return
+	}
+	h.mu.Unlock()
+	scanFn()
+}
+
+// isRepoDeleted returns true when the repo root directory or its .git
+// entry no longer represents a valid git repository. This
+// distinguishes a genuine repo deletion from a transient scan error
+// (e.g. lock contention).
+//
+// It handles three deletion cases:
+//  1. The repo root directory itself was removed.
+//  2. The .git entry (directory or file) was removed.
+//  3. The .git entry is a file (worktree/submodule) whose target
+//     gitdir was removed. In this case .git exists on disk but
+//     `git rev-parse --git-dir` fails because the referenced
+//     directory is gone.
+func isRepoDeleted(gitBin string, repoRoot string) bool {
+	if _, err := os.Stat(repoRoot); os.IsNotExist(err) {
+		return true
+	}
+	gitPath := filepath.Join(repoRoot, ".git")
+	fi, err := os.Stat(gitPath)
+	if os.IsNotExist(err) {
+		return true
+	}
+	// If .git is a regular file (worktree or submodule), the actual
+	// git object store lives elsewhere. Validate that the target is
+	// still reachable by running git rev-parse.
+	if err == nil && !fi.IsDir() {
+		cmd := exec.CommandContext(context.Background(), gitBin, "-C", repoRoot, "rev-parse", "--git-dir")
+		if err := cmd.Run(); err != nil {
+			return true
+		}
+	}
+	return false
+}
+
+// findRepoRoot uses `git rev-parse --show-toplevel` to find the
+// repository root for the given path.
+func findRepoRoot(gitBin string, p string) (string, error) {
+	// If p is a file, start from its parent directory.
+	dir := p
+	if info, err := os.Stat(dir); err != nil || !info.IsDir() {
+		dir = filepath.Dir(dir)
+	}
+	cmd := exec.CommandContext(context.Background(), gitBin, "rev-parse", "--show-toplevel")
+	cmd.Dir = dir
+	out, err := cmd.Output()
+	if err != nil {
+		return "", xerrors.Errorf("no git repo found for %s", p)
+	}
+	root := filepath.FromSlash(strings.TrimSpace(string(out)))
+	// Resolve symlinks and short (8.3) names on Windows so the
+	// returned root matches paths produced by Go's filepath APIs.
+	if resolved, evalErr := filepath.EvalSymlinks(root); evalErr == nil {
+		root = resolved
+	}
+	return root, nil
+}
+
+// getRepoChanges reads the current state of a git repository using
+// the git CLI. It returns branch, remote origin, and a unified diff.
+func getRepoChanges(ctx context.Context, logger slog.Logger, gitBin string, repoRoot string) (codersdk.WorkspaceAgentRepoChanges, error) {
+	result := codersdk.WorkspaceAgentRepoChanges{
+		RepoRoot: repoRoot,
+	}
+
+	// Verify this is still a valid git repository before doing
+	// anything else. This catches deleted repos early.
+	verifyCmd := exec.CommandContext(ctx, gitBin, "-C", repoRoot, "rev-parse", "--git-dir")
+	if err := verifyCmd.Run(); err != nil {
+		return result, xerrors.Errorf("not a git repository: %w", err)
+	}
+
+	// Read branch name.
+	branchCmd := exec.CommandContext(ctx, gitBin, "-C", repoRoot, "symbolic-ref", "--short", "HEAD")
+	if out, err := branchCmd.Output(); err == nil {
+		result.Branch = strings.TrimSpace(string(out))
+	} else {
+		logger.Debug(ctx, "failed to read HEAD", slog.F("root", repoRoot), slog.Error(err))
+	}
+
+	// Read remote origin URL.
+	remoteCmd := exec.CommandContext(ctx, gitBin, "-C", repoRoot, "config", "--get", "remote.origin.url")
+	if out, err := remoteCmd.Output(); err == nil {
+		result.RemoteOrigin = strings.TrimSpace(string(out))
+	}
+
+	// Compute unified diff.
+	// `git diff HEAD` shows both staged and unstaged changes vs HEAD.
+	// For repos with no commits yet, fall back to showing untracked
+	// files only.
+	diff, err := computeGitDiff(ctx, logger, gitBin, repoRoot)
+	if err != nil {
+		return result, xerrors.Errorf("compute diff: %w", err)
+	}
+
+	result.UnifiedDiff = diff
+	if len(result.UnifiedDiff) > maxTotalDiffSize {
+		result.UnifiedDiff = "Total diff too large to show. Size: " + humanize.IBytes(uint64(len(result.UnifiedDiff))) + ". Showing branch and remote only."
+	}
+
+	return result, nil
+}
+
+// computeGitDiff produces a unified diff string for the repository by
+// combining `git diff HEAD` (staged + unstaged changes) with diffs
+// for untracked files.
+func computeGitDiff(ctx context.Context, logger slog.Logger, gitBin string, repoRoot string) (string, error) {
+	var diffParts []string
+
+	// Check if the repo has any commits.
+	hasCommits := true
+	checkCmd := exec.CommandContext(ctx, gitBin, "-C", repoRoot, "rev-parse", "HEAD")
+	if err := checkCmd.Run(); err != nil {
+		hasCommits = false
+	}
+
+	if hasCommits {
+		// `git diff HEAD` captures both staged and unstaged changes
+		// relative to HEAD in a single unified diff.
+		cmd := exec.CommandContext(ctx, gitBin, "-C", repoRoot, "diff", "HEAD")
+		out, err := cmd.Output()
+		if err != nil {
+			return "", xerrors.Errorf("git diff HEAD: %w", err)
+		}
+		if len(out) > 0 {
+			diffParts = append(diffParts, string(out))
+		}
+	}
+
+	// Show untracked files as diffs too.
+	// `git ls-files --others --exclude-standard` lists untracked,
+	// non-ignored files.
+	lsCmd := exec.CommandContext(ctx, gitBin, "-C", repoRoot, "ls-files", "--others", "--exclude-standard")
+	lsOut, err := lsCmd.Output()
+	if err != nil {
+		logger.Debug(ctx, "failed to list untracked files", slog.F("root", repoRoot), slog.Error(err))
+		return strings.Join(diffParts, ""), nil
+	}
+
+	untrackedFiles := strings.Split(strings.TrimSpace(string(lsOut)), "\n")
+	for _, f := range untrackedFiles {
+		f = strings.TrimSpace(f)
+		if f == "" {
+			continue
+		}
+		// Use `git diff --no-index /dev/null <file>` to generate
+		// a unified diff for untracked files.
+		var stdout bytes.Buffer
+		untrackedCmd := exec.CommandContext(ctx, gitBin, "-C", repoRoot, "diff", "--no-index", "--", "/dev/null", f)
+		untrackedCmd.Stdout = &stdout
+		// git diff --no-index exits with 1 when files differ,
+		// which is expected. We ignore the error and check for
+		// output instead.
+		_ = untrackedCmd.Run()
+		if stdout.Len() > 0 {
+			diffParts = append(diffParts, stdout.String())
+		}
+	}
+
+	return strings.Join(diffParts, ""), nil
+}
@@ -0,0 +1,147 @@
+package agentgit
+
+import (
+	"context"
+	"net/http"
+
+	"github.com/go-chi/chi/v5"
+	"github.com/google/uuid"
+
+	"cdr.dev/slog/v3"
+	"github.com/coder/coder/v2/coderd/httpapi"
+	"github.com/coder/coder/v2/codersdk"
+	"github.com/coder/coder/v2/codersdk/wsjson"
+	"github.com/coder/websocket"
+)
+
+// API exposes the git watch HTTP routes for the agent.
+type API struct {
+	logger    slog.Logger
+	opts      []Option
+	pathStore *PathStore
+}
+
+// NewAPI creates a new git watch API.
+func NewAPI(logger slog.Logger, pathStore *PathStore, opts ...Option) *API {
+	return &API{
+		logger:    logger,
+		pathStore: pathStore,
+		opts:      opts,
+	}
+}
+
+// Routes returns the chi router for mounting at /api/v0/git.
+func (a *API) Routes() http.Handler {
+	r := chi.NewRouter()
+	r.Get("/watch", a.handleWatch)
+	return r
+}
+
+func (a *API) handleWatch(rw http.ResponseWriter, r *http.Request) {
+	ctx := r.Context()
+
+	conn, err := websocket.Accept(rw, r, &websocket.AcceptOptions{
+		CompressionMode: websocket.CompressionNoContextTakeover,
+	})
+	if err != nil {
+		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
+			Message: "Failed to accept WebSocket.",
+			Detail:  err.Error(),
+		})
+		return
+	}
+
+	// 4 MiB read limit — subscribe messages with many paths can exceed the
+	// default 32 KB limit. Matches the SDK/proxy side.
+	conn.SetReadLimit(1 << 22)
+
+	stream := wsjson.NewStream[
+		codersdk.WorkspaceAgentGitClientMessage,
+		codersdk.WorkspaceAgentGitServerMessage,
+	](conn, websocket.MessageText, websocket.MessageText, a.logger)
+
+	ctx, cancel := context.WithCancel(ctx)
+	defer cancel()
+
+	go httpapi.HeartbeatClose(ctx, a.logger, cancel, conn)
+
+	handler := NewHandler(a.logger, a.opts...)
+
+	// scanAndSend performs a scan and sends results if there are
+	// changes.
+	scanAndSend := func() {
+		msg := handler.Scan(ctx)
+		if msg != nil {
+			if err := stream.Send(*msg); err != nil {
+				a.logger.Debug(ctx, "failed to send changes", slog.Error(err))
+				cancel()
+			}
+		}
+	}
+
+	// If a chat_id query parameter is provided and the PathStore is
+	// available, subscribe to path updates for this chat.
+	chatIDStr := r.URL.Query().Get("chat_id")
+	if chatIDStr != "" && a.pathStore != nil {
+		chatID, parseErr := uuid.Parse(chatIDStr)
+		if parseErr == nil {
+			// Subscribe to future path updates BEFORE reading
+			// existing paths. This ordering guarantees no
+			// notification from AddPaths is lost: any call that
+			// lands before Subscribe is picked up by GetPaths
+			// below, and any call after Subscribe delivers a
+			// notification on the channel.
+			notifyCh, unsubscribe := a.pathStore.Subscribe(chatID)
+			defer unsubscribe()
+
+			// Load any paths that are already tracked for this chat.
+			existingPaths := a.pathStore.GetPaths(chatID)
+			if len(existingPaths) > 0 {
+				handler.Subscribe(existingPaths)
+				handler.RequestScan()
+			}
+
+			go func() {
+				for {
+					select {
+					case <-ctx.Done():
+						return
+					case <-notifyCh:
+						paths := a.pathStore.GetPaths(chatID)
+						handler.Subscribe(paths)
+						handler.RequestScan()
+					}
+				}
+			}()
+		}
+	}
+
+	// Start the main run loop in a goroutine.
+	go handler.RunLoop(ctx, scanAndSend)
+
+	// Read client messages.
+	updates := stream.Chan()
+	for {
+		select {
+		case <-ctx.Done():
+			_ = stream.Close(websocket.StatusGoingAway)
+			return
+		case msg, ok := <-updates:
+			if !ok {
+				return
+			}
+
+			switch msg.Type {
+			case codersdk.WorkspaceAgentGitClientMessageTypeRefresh:
+				handler.RequestScan()
+			default:
+				if err := stream.Send(codersdk.WorkspaceAgentGitServerMessage{
+					Type:    codersdk.WorkspaceAgentGitServerMessageTypeError,
+					Message: "unknown message type",
+				}); err != nil {
+					return
+				}
+			}
+		}
+	}
+}
@@ -0,0 +1,35 @@
+package agentgit
+
+import (
+	"encoding/json"
+	"net/http"
+
+	"github.com/google/uuid"
+
+	"github.com/coder/coder/v2/codersdk/workspacesdk"
+)
+
+// ExtractChatContext reads chat identity headers from the request.
+// Returns zero values if headers are absent (non-chat request).
+func ExtractChatContext(r *http.Request) (chatID uuid.UUID, ancestorIDs []uuid.UUID, ok bool) {
+	raw := r.Header.Get(workspacesdk.CoderChatIDHeader)
+	if raw == "" {
+		return uuid.Nil, nil, false
+	}
+	chatID, err := uuid.Parse(raw)
+	if err != nil {
+		return uuid.Nil, nil, false
+	}
+	rawAncestors := r.Header.Get(workspacesdk.CoderAncestorChatIDsHeader)
+	if rawAncestors != "" {
+		var ids []string
+		if err := json.Unmarshal([]byte(rawAncestors), &ids); err == nil {
+			for _, s := range ids {
+				if id, err := uuid.Parse(s); err == nil {
+					ancestorIDs = append(ancestorIDs, id)
+				}
+			}
+		}
+	}
+	return chatID, ancestorIDs, true
+}
@@ -0,0 +1,148 @@
+package agentgit_test
+
+import (
+	"encoding/json"
+	"net/http/httptest"
+	"testing"
+
+	"github.com/google/uuid"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/agent/agentgit"
+	"github.com/coder/coder/v2/codersdk/workspacesdk"
+)
+
+func TestExtractChatContext(t *testing.T) {
+	t.Parallel()
+
+	validID := uuid.MustParse("aaaaaaaa-bbbb-cccc-dddd-eeeeeeeeeeee")
+	ancestor1 := uuid.MustParse("11111111-2222-3333-4444-555555555555")
+	ancestor2 := uuid.MustParse("66666666-7777-8888-9999-aaaaaaaaaaaa")
+
+	tests := []struct {
+		name            string
+		chatID          string // empty means header not set
+		setChatID       bool   // whether to set the chat ID header at all
+		ancestors       string // empty means header not set
+		setAncestors    bool   // whether to set the ancestor header at all
+		wantChatID      uuid.UUID
+		wantAncestorIDs []uuid.UUID
+		wantOK          bool
+	}{
+		{
+			name:            "NoHeadersPresent",
+			setChatID:       false,
+			setAncestors:    false,
+			wantChatID:      uuid.Nil,
+			wantAncestorIDs: nil,
+			wantOK:          false,
+		},
+		{
+			name:            "ValidChatID_NoAncestors",
+			chatID:          validID.String(),
+			setChatID:       true,
+			setAncestors:    false,
+			wantChatID:      validID,
+			wantAncestorIDs: nil,
+			wantOK:          true,
+		},
+		{
+			name:      "ValidChatID_ValidAncestors",
+			chatID:    validID.String(),
+			setChatID: true,
+			ancestors: mustMarshalJSON(t, []string{
+				ancestor1.String(),
+				ancestor2.String(),
+			}),
+			setAncestors:    true,
+			wantChatID:      validID,
+			wantAncestorIDs: []uuid.UUID{ancestor1, ancestor2},
+			wantOK:          true,
+		},
+		{
+			name:            "MalformedChatID",
+			chatID:          "not-a-uuid",
+			setChatID:       true,
+			setAncestors:    false,
+			wantChatID:      uuid.Nil,
+			wantAncestorIDs: nil,
+			wantOK:          false,
+		},
+		{
+			name:            "ValidChatID_MalformedAncestorJSON",
+			chatID:          validID.String(),
+			setChatID:       true,
+			ancestors:       `{this is not json}`,
+			setAncestors:    true,
+			wantChatID:      validID,
+			wantAncestorIDs: nil,
+			wantOK:          true,
+		},
+		{
+			// Only valid UUIDs in the array are returned; invalid
+			// entries are silently skipped.
+			name:      "ValidChatID_PartialValidAncestorUUIDs",
+			chatID:    validID.String(),
+			setChatID: true,
+			ancestors: mustMarshalJSON(t, []string{
+				ancestor1.String(),
+				"bad-uuid",
+				ancestor2.String(),
+			}),
+			setAncestors:    true,
+			wantChatID:      validID,
+			wantAncestorIDs: []uuid.UUID{ancestor1, ancestor2},
+			wantOK:          true,
+		},
+		{
+			// Header is explicitly set to an empty string, which
+			// Header.Get returns as "".
+			name:            "EmptyChatIDHeader",
+			chatID:          "",
+			setChatID:       true,
+			setAncestors:    false,
+			wantChatID:      uuid.Nil,
+			wantAncestorIDs: nil,
+			wantOK:          false,
+		},
+		{
+			name:            "ValidChatID_EmptyAncestorHeader",
+			chatID:          validID.String(),
+			setChatID:       true,
+			ancestors:       "",
+			setAncestors:    true,
+			wantChatID:      validID,
+			wantAncestorIDs: nil,
+			wantOK:          true,
+		},
+	}
+
+	for _, tt := range tests {
+		tt := tt
+		t.Run(tt.name, func(t *testing.T) {
+			t.Parallel()
+
+			r := httptest.NewRequest("GET", "/", nil)
+			if tt.setChatID {
+				r.Header.Set(workspacesdk.CoderChatIDHeader, tt.chatID)
+			}
+			if tt.setAncestors {
+				r.Header.Set(workspacesdk.CoderAncestorChatIDsHeader, tt.ancestors)
+			}
+
+			chatID, ancestorIDs, ok := agentgit.ExtractChatContext(r)
+
+			require.Equal(t, tt.wantOK, ok, "ok mismatch")
+			require.Equal(t, tt.wantChatID, chatID, "chatID mismatch")
+			require.Equal(t, tt.wantAncestorIDs, ancestorIDs, "ancestorIDs mismatch")
+		})
+	}
+}
+
+// mustMarshalJSON marshals v to a JSON string, failing the test on error.
+func mustMarshalJSON(t *testing.T, v any) string {
+	t.Helper()
+	b, err := json.Marshal(v)
+	require.NoError(t, err)
+	return string(b)
+}
@@ -0,0 +1,136 @@
+package agentgit
+
+import (
+	"slices"
+	"sync"
+
+	"github.com/google/uuid"
+)
+
+// PathStore tracks which file paths each chat has touched.
+// It is safe for concurrent use.
+type PathStore struct {
+	mu          sync.RWMutex
+	chatPaths   map[uuid.UUID]map[string]struct{}
+	subscribers map[uuid.UUID][]chan<- struct{}
+}
+
+// NewPathStore creates a new PathStore.
+func NewPathStore() *PathStore {
+	return &PathStore{
+		chatPaths:   make(map[uuid.UUID]map[string]struct{}),
+		subscribers: make(map[uuid.UUID][]chan<- struct{}),
+	}
+}
+
+// AddPaths adds paths to every chat in chatIDs and notifies
+// their subscribers. Zero-value UUIDs are silently skipped.
+func (ps *PathStore) AddPaths(chatIDs []uuid.UUID, paths []string) {
+	affected := make([]uuid.UUID, 0, len(chatIDs))
+	for _, id := range chatIDs {
+		if id != uuid.Nil {
+			affected = append(affected, id)
+		}
+	}
+	if len(affected) == 0 {
+		return
+	}
+
+	ps.mu.Lock()
+	for _, id := range affected {
+		m, ok := ps.chatPaths[id]
+		if !ok {
+			m = make(map[string]struct{})
+			ps.chatPaths[id] = m
+		}
+		for _, p := range paths {
+			m[p] = struct{}{}
+		}
+	}
+	ps.mu.Unlock()
+
+	ps.notifySubscribers(affected)
+}
+
+// Notify sends a signal to all subscribers of the given chat IDs
+// without adding any paths. Zero-value UUIDs are silently skipped.
+func (ps *PathStore) Notify(chatIDs []uuid.UUID) {
+	affected := make([]uuid.UUID, 0, len(chatIDs))
+	for _, id := range chatIDs {
+		if id != uuid.Nil {
+			affected = append(affected, id)
+		}
+	}
+	if len(affected) == 0 {
+		return
+	}
+	ps.notifySubscribers(affected)
+}
+
+// notifySubscribers sends a non-blocking signal to all subscriber
+// channels for the given chat IDs.
+func (ps *PathStore) notifySubscribers(chatIDs []uuid.UUID) {
+	ps.mu.RLock()
+	toNotify := make([]chan<- struct{}, 0)
+	for _, id := range chatIDs {
+		toNotify = append(toNotify, ps.subscribers[id]...)
+	}
+	ps.mu.RUnlock()
+
+	for _, ch := range toNotify {
+		select {
+		case ch <- struct{}{}:
+		default:
+		}
+	}
+}
+
+// GetPaths returns all paths tracked for a chat, deduplicated
+// and sorted lexicographically.
+func (ps *PathStore) GetPaths(chatID uuid.UUID) []string {
+	ps.mu.RLock()
+	defer ps.mu.RUnlock()
+
+	m := ps.chatPaths[chatID]
+	if len(m) == 0 {
+		return nil
+	}
+	out := make([]string, 0, len(m))
+	for p := range m {
+		out = append(out, p)
+	}
+	slices.Sort(out)
+	return out
+}
+
+// Len returns the number of chat IDs that have tracked paths.
+func (ps *PathStore) Len() int {
+	ps.mu.RLock()
+	defer ps.mu.RUnlock()
+	return len(ps.chatPaths)
+}
+
+// Subscribe returns a channel that receives a signal whenever
+// paths change for chatID, along with an unsubscribe function
+// that removes the channel.
+func (ps *PathStore) Subscribe(chatID uuid.UUID) (<-chan struct{}, func()) {
+	ch := make(chan struct{}, 1)
+
+	ps.mu.Lock()
+	ps.subscribers[chatID] = append(ps.subscribers[chatID], ch)
+	ps.mu.Unlock()
+
+	unsub := func() {
+		ps.mu.Lock()
+		defer ps.mu.Unlock()
+		subs := ps.subscribers[chatID]
+		for i, s := range subs {
+			if s == ch {
+				ps.subscribers[chatID] = append(subs[:i], subs[i+1:]...)
+				break
+			}
+		}
+	}
+
+	return ch, unsub
+}
@@ -0,0 +1,268 @@
+package agentgit_test
+
+import (
+	"sync"
+	"testing"
+	"time"
+
+	"github.com/google/uuid"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/agent/agentgit"
+	"github.com/coder/coder/v2/testutil"
+)
+
+func TestPathStore_AddPaths_StoresForChatAndAncestors(t *testing.T) {
+	t.Parallel()
+
+	ps := agentgit.NewPathStore()
+	chatID := uuid.New()
+	ancestor1 := uuid.New()
+	ancestor2 := uuid.New()
+
+	ps.AddPaths([]uuid.UUID{chatID, ancestor1, ancestor2}, []string{"/a", "/b"})
+
+	// All three IDs should see the paths.
+	require.Equal(t, []string{"/a", "/b"}, ps.GetPaths(chatID))
+	require.Equal(t, []string{"/a", "/b"}, ps.GetPaths(ancestor1))
+	require.Equal(t, []string{"/a", "/b"}, ps.GetPaths(ancestor2))
+
+	// An unrelated chat should see nothing.
+	require.Nil(t, ps.GetPaths(uuid.New()))
+}
+
+func TestPathStore_AddPaths_SkipsNilUUIDs(t *testing.T) {
+	t.Parallel()
+
+	ps := agentgit.NewPathStore()
+
+	// A nil chatID should be a no-op.
+	ps.AddPaths([]uuid.UUID{uuid.Nil}, []string{"/x"})
+	require.Nil(t, ps.GetPaths(uuid.Nil))
+
+	// A nil ancestor should be silently skipped.
+	chatID := uuid.New()
+	ps.AddPaths([]uuid.UUID{chatID, uuid.Nil}, []string{"/y"})
+	require.Equal(t, []string{"/y"}, ps.GetPaths(chatID))
+	require.Nil(t, ps.GetPaths(uuid.Nil))
+}
+
+func TestPathStore_GetPaths_DeduplicatedSorted(t *testing.T) {
+	t.Parallel()
+
+	ps := agentgit.NewPathStore()
+	chatID := uuid.New()
+
+	ps.AddPaths([]uuid.UUID{chatID}, []string{"/z", "/a", "/m", "/a", "/z"})
+	ps.AddPaths([]uuid.UUID{chatID}, []string{"/a", "/b"})
+
+	got := ps.GetPaths(chatID)
+	require.Equal(t, []string{"/a", "/b", "/m", "/z"}, got)
+}
+
+func TestPathStore_Subscribe_ReceivesNotification(t *testing.T) {
+	t.Parallel()
+
+	ps := agentgit.NewPathStore()
+	chatID := uuid.New()
+
+	ch, unsub := ps.Subscribe(chatID)
+	defer unsub()
+
+	ps.AddPaths([]uuid.UUID{chatID}, []string{"/file"})
+
+	ctx := testutil.Context(t, testutil.WaitShort)
+	select {
+	case <-ch:
+		// Success.
+	case <-ctx.Done():
+		t.Fatal("timed out waiting for notification")
+	}
+}
+
+func TestPathStore_Subscribe_MultipleSubscribers(t *testing.T) {
+	t.Parallel()
+
+	ps := agentgit.NewPathStore()
+	chatID := uuid.New()
+
+	ch1, unsub1 := ps.Subscribe(chatID)
+	defer unsub1()
+	ch2, unsub2 := ps.Subscribe(chatID)
+	defer unsub2()
+
+	ps.AddPaths([]uuid.UUID{chatID}, []string{"/file"})
+
+	ctx := testutil.Context(t, testutil.WaitShort)
+	for i, ch := range []<-chan struct{}{ch1, ch2} {
+		select {
+		case <-ch:
+			// OK
+		case <-ctx.Done():
+			t.Fatalf("subscriber %d did not receive notification", i)
+		}
+	}
+}
+
+func TestPathStore_Unsubscribe_StopsNotifications(t *testing.T) {
+	t.Parallel()
+
+	ps := agentgit.NewPathStore()
+	chatID := uuid.New()
+
+	ch, unsub := ps.Subscribe(chatID)
+	unsub()
+
+	ps.AddPaths([]uuid.UUID{chatID}, []string{"/file"})
+
+	// AddPaths sends synchronously via a non-blocking send to the
+	// buffered channel, so if a notification were going to arrive
+	// it would already be in the channel by now.
+	select {
+	case <-ch:
+		t.Fatal("received notification after unsubscribe")
+	default:
+		// Expected: no notification.
+	}
+}
+
+func TestPathStore_Subscribe_AncestorNotification(t *testing.T) {
+	t.Parallel()
+
+	ps := agentgit.NewPathStore()
+	chatID := uuid.New()
+	ancestor := uuid.New()
+
+	// Subscribe to the ancestor, then add paths via the child.
+	ch, unsub := ps.Subscribe(ancestor)
+	defer unsub()
+
+	ps.AddPaths([]uuid.UUID{chatID, ancestor}, []string{"/file"})
+
+	ctx := testutil.Context(t, testutil.WaitShort)
+	select {
+	case <-ch:
+		// Success.
+	case <-ctx.Done():
+		t.Fatal("ancestor subscriber did not receive notification")
+	}
+}
+
+func TestPathStore_Notify_NotifiesWithoutAddingPaths(t *testing.T) {
+	t.Parallel()
+
+	ps := agentgit.NewPathStore()
+	chatID := uuid.New()
+
+	ch, unsub := ps.Subscribe(chatID)
+	defer unsub()
+
+	ps.Notify([]uuid.UUID{chatID})
+
+	ctx := testutil.Context(t, testutil.WaitShort)
+	select {
+	case <-ch:
+		// Success.
+	case <-ctx.Done():
+		t.Fatal("timed out waiting for notification")
+	}
+
+	require.Nil(t, ps.GetPaths(chatID))
+}
+
+func TestPathStore_Notify_SkipsNilUUIDs(t *testing.T) {
+	t.Parallel()
+
+	ps := agentgit.NewPathStore()
+	chatID := uuid.New()
+
+	ch, unsub := ps.Subscribe(chatID)
+	defer unsub()
+
+	ps.Notify([]uuid.UUID{uuid.Nil})
+
+	// Notify sends synchronously via a non-blocking send to the
+	// buffered channel, so if a notification were going to arrive
+	// it would already be in the channel by now.
+	select {
+	case <-ch:
+		t.Fatal("received notification for nil UUID")
+	default:
+		// Expected: no notification.
+	}
+
+	require.Nil(t, ps.GetPaths(chatID))
+}
+
+func TestPathStore_Notify_AncestorNotification(t *testing.T) {
+	t.Parallel()
+
+	ps := agentgit.NewPathStore()
+	chatID := uuid.New()
+	ancestorID := uuid.New()
+
+	// Subscribe to the ancestor, then notify via the child.
+	ch, unsub := ps.Subscribe(ancestorID)
+	defer unsub()
+
+	ps.Notify([]uuid.UUID{chatID, ancestorID})
+
+	ctx := testutil.Context(t, testutil.WaitShort)
+	select {
+	case <-ch:
+		// Success.
+	case <-ctx.Done():
+		t.Fatal("ancestor subscriber did not receive notification")
+	}
+
+	require.Nil(t, ps.GetPaths(ancestorID))
+}
+
+func TestPathStore_ConcurrentSafety(t *testing.T) {
+	t.Parallel()
+
+	ps := agentgit.NewPathStore()
+	const goroutines = 20
+	const iterations = 50
+
+	chatIDs := make([]uuid.UUID, goroutines)
+	for i := range chatIDs {
+		chatIDs[i] = uuid.New()
+	}
+
+	var wg sync.WaitGroup
+	wg.Add(goroutines * 2) // writers + readers
+
+	// Writers.
+	for i := range goroutines {
+		go func(idx int) {
+			defer wg.Done()
+			for j := range iterations {
+				ancestors := []uuid.UUID{chatIDs[(idx+1)%goroutines]}
+				path := []string{
+					"/file-" + chatIDs[idx].String() + "-" + time.Now().Format(time.RFC3339Nano),
+					"/iter-" + string(rune('0'+j%10)),
+				}
+				ps.AddPaths(append([]uuid.UUID{chatIDs[idx]}, ancestors...), path)
+			}
+		}(i)
+	}
+
+	// Readers.
+	for i := range goroutines {
+		go func(idx int) {
+			defer wg.Done()
+			for range iterations {
+				_ = ps.GetPaths(chatIDs[idx])
+			}
+		}(i)
+	}
+
+	wg.Wait()
+
+	// Verify every chat has at least the paths it wrote.
+	for _, id := range chatIDs {
+		paths := ps.GetPaths(id)
+		require.NotEmpty(t, paths, "chat %s should have paths", id)
+	}
+}
@@ -1,31 +1,45 @@
 package agentproc

 import (
+	"context"
 	"encoding/json"
 	"errors"
 	"fmt"
 	"net/http"
+	"sort"
+	"time"

 	"github.com/go-chi/chi/v5"
+	"github.com/google/uuid"

 	"cdr.dev/slog/v3"
 	"github.com/coder/coder/v2/agent/agentexec"
+	"github.com/coder/coder/v2/agent/agentgit"
 	"github.com/coder/coder/v2/coderd/httpapi"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/codersdk/workspacesdk"
 )

+const (
+	// maxWaitDuration is the maximum time a blocking
+	// process output request can wait, regardless of
+	// what the client requests.
+	maxWaitDuration = 5 * time.Minute
+)
+
 // API exposes process-related operations through the agent.
 type API struct {
-	logger  slog.Logger
-	manager *manager
+	logger    slog.Logger
+	manager   *manager
+	pathStore *agentgit.PathStore
 }

 // NewAPI creates a new process API handler.
-func NewAPI(logger slog.Logger, execer agentexec.Execer, updateEnv func(current []string) (updated []string, err error)) *API {
+func NewAPI(logger slog.Logger, execer agentexec.Execer, updateEnv func(current []string) (updated []string, err error), pathStore *agentgit.PathStore, workingDir func() string) *API {
 	return &API{
-		logger:  logger,
-		manager: newManager(logger, execer, updateEnv),
+		logger:    logger,
+		manager:   newManager(logger, execer, updateEnv, workingDir),
+		pathStore: pathStore,
 	}
 }

@@ -65,7 +79,12 @@ func (api *API) handleStartProcess(rw http.ResponseWriter, r *http.Request) {
 		return
 	}

-	proc, err := api.manager.start(req)
+	var chatID string
+	if id, _, ok := agentgit.ExtractChatContext(r); ok {
+		chatID = id.String()
+	}
+
+	proc, err := api.manager.start(req, chatID)
 	if err != nil {
 		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
 			Message: "Failed to start process.",
@@ -74,6 +93,23 @@ func (api *API) handleStartProcess(rw http.ResponseWriter, r *http.Request) {
 		return
 	}

+	// Notify git watchers after the process finishes so that
+	// file changes made by the command are visible in the scan.
+	// If a workdir is provided, track it as a path as well.
+	if api.pathStore != nil {
+		if chatID, ancestorIDs, ok := agentgit.ExtractChatContext(r); ok {
+			allIDs := append([]uuid.UUID{chatID}, ancestorIDs...)
+			go func() {
+				<-proc.done
+				if req.WorkDir != "" {
+					api.pathStore.AddPaths(allIDs, []string{req.WorkDir})
+				} else {
+					api.pathStore.Notify(allIDs)
+				}
+			}()
+		}
+	}
+
 	httpapi.Write(ctx, rw, http.StatusOK, workspacesdk.StartProcessResponse{
 		ID:      proc.id,
 		Started: true,
@@ -84,7 +120,28 @@ func (api *API) handleStartProcess(rw http.ResponseWriter, r *http.Request) {
 func (api *API) handleListProcesses(rw http.ResponseWriter, r *http.Request) {
 	ctx := r.Context()

-	infos := api.manager.list()
+	var chatID string
+	if id, _, ok := agentgit.ExtractChatContext(r); ok {
+		chatID = id.String()
+	}
+
+	infos := api.manager.list(chatID)
+
+	// Sort by running state (running first), then by started_at
+	// descending so the most recent processes appear first.
+	sort.Slice(infos, func(i, j int) bool {
+		if infos[i].Running != infos[j].Running {
+			return infos[i].Running
+		}
+		return infos[i].StartedAt > infos[j].StartedAt
+	})
+
+	// Cap the response to avoid bloating LLM context.
+	const maxListProcesses = 10
+	if len(infos) > maxListProcesses {
+		infos = infos[:maxListProcesses]
+	}
+
 	httpapi.Write(ctx, rw, http.StatusOK, workspacesdk.ListProcessesResponse{
 		Processes: infos,
 	})
@@ -103,6 +160,44 @@ func (api *API) handleProcessOutput(rw http.ResponseWriter, r *http.Request) {
 		return
 	}

+	// Enforce chat ID isolation. If the request carries
+	// a chat context, only allow access to processes
+	// belonging to that chat.
+	if chatID, _, ok := agentgit.ExtractChatContext(r); ok {
+		if proc.chatID != "" && proc.chatID != chatID.String() {
+			httpapi.Write(ctx, rw, http.StatusNotFound, codersdk.Response{
+				Message: fmt.Sprintf("Process %q not found.", id),
+			})
+			return
+		}
+	}
+
+	// Check for blocking mode via query params.
+	waitStr := r.URL.Query().Get("wait")
+	wantWait := waitStr == "true"
+
+	if wantWait {
+		// Extend the write deadline so the HTTP server's
+		// WriteTimeout does not kill the connection while
+		// we block.
+		rc := http.NewResponseController(rw)
+		// Add headroom beyond the wait timeout so there's time to
+		// write the response after the blocking wait completes.
+		if err := rc.SetWriteDeadline(time.Now().Add(maxWaitDuration + 30*time.Second)); err != nil {
+			api.logger.Error(ctx, "extend write deadline for blocking process output",
+				slog.Error(err),
+			)
+		}
+
+		// Cap the wait at maxWaitDuration regardless of
+		// client-supplied timeout.
+		waitCtx, waitCancel := context.WithTimeout(ctx, maxWaitDuration)
+		defer waitCancel()
+
+		_ = proc.waitForOutput(waitCtx)
+		// Fall through to read snapshot below.
+	}
+
 	output, truncated := proc.output()
 	info := proc.info()

@@ -120,6 +215,17 @@ func (api *API) handleSignalProcess(rw http.ResponseWriter, r *http.Request) {

 	id := chi.URLParam(r, "id")

+	// Enforce chat ID isolation.
+	if chatID, _, ok := agentgit.ExtractChatContext(r); ok {
+		proc, procOK := api.manager.get(id)
+		if procOK && proc.chatID != "" && proc.chatID != chatID.String() {
+			httpapi.Write(ctx, rw, http.StatusNotFound, codersdk.Response{
+				Message: fmt.Sprintf("Process %q not found.", id),
+			})
+			return
+		}
+	}
+
 	var req workspacesdk.SignalProcessRequest
 	if err := json.NewDecoder(r.Body).Decode(&req); err != nil {
 		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
@@ -7,17 +7,21 @@ import (
 	"fmt"
 	"net/http"
 	"net/http/httptest"
+	"os"
 	"runtime"
 	"strings"
+	"sync"
 	"testing"
 	"time"

+	"github.com/google/uuid"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"

 	"cdr.dev/slog/v3"
 	"cdr.dev/slog/v3/sloggers/slogtest"
 	"github.com/coder/coder/v2/agent/agentexec"
+	"github.com/coder/coder/v2/agent/agentgit"
 	"github.com/coder/coder/v2/agent/agentproc"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/codersdk/workspacesdk"
@@ -25,7 +29,7 @@ import (
 )

 // postStart sends a POST /start request and returns the recorder.
-func postStart(t *testing.T, handler http.Handler, req workspacesdk.StartProcessRequest) *httptest.ResponseRecorder {
+func postStart(t *testing.T, handler http.Handler, req workspacesdk.StartProcessRequest, headers ...http.Header) *httptest.ResponseRecorder {
 	t.Helper()

 	ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
@@ -36,6 +40,13 @@ func postStart(t *testing.T, handler http.Handler, req workspacesdk.StartProcess

 	w := httptest.NewRecorder()
 	r := httptest.NewRequestWithContext(ctx, http.MethodPost, "/start", bytes.NewReader(body))
+	for _, h := range headers {
+		for k, vals := range h {
+			for _, v := range vals {
+				r.Header.Add(k, v)
+			}
+		}
+	}
 	handler.ServeHTTP(w, r)
 	return w
 }
@@ -67,6 +78,22 @@ func getOutput(t *testing.T, handler http.Handler, id string) *httptest.Response
 	return w
 }

+// getOutputWithHeaders sends a GET /{id}/output request with
+// custom headers and returns the recorder.
+func getOutputWithHeaders(t *testing.T, handler http.Handler, id string, headers http.Header) *httptest.ResponseRecorder {
+	t.Helper()
+	ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
+	defer cancel()
+	path := fmt.Sprintf("/%s/output", id)
+	req := httptest.NewRequestWithContext(ctx, http.MethodGet, path, nil)
+	for k, v := range headers {
+		req.Header[k] = v
+	}
+	w := httptest.NewRecorder()
+	handler.ServeHTTP(w, req)
+	return w
+}
+
 // postSignal sends a POST /{id}/signal request and returns
 // the recorder.
 func postSignal(t *testing.T, handler http.Handler, id string, req workspacesdk.SignalProcessRequest) *httptest.ResponseRecorder {
@@ -88,18 +115,25 @@ func postSignal(t *testing.T, handler http.Handler, id string, req workspacesdk.
 // execer, returning the handler and API.
 func newTestAPI(t *testing.T) http.Handler {
 	t.Helper()
-	return newTestAPIWithUpdateEnv(t, nil)
+	return newTestAPIWithOptions(t, nil, nil)
 }

 // newTestAPIWithUpdateEnv creates a new API with an optional
 // updateEnv hook for testing environment injection.
 func newTestAPIWithUpdateEnv(t *testing.T, updateEnv func([]string) ([]string, error)) http.Handler {
 	t.Helper()
+	return newTestAPIWithOptions(t, updateEnv, nil)
+}
+
+// newTestAPIWithOptions creates a new API with optional
+// updateEnv and workingDir hooks.
+func newTestAPIWithOptions(t *testing.T, updateEnv func([]string) ([]string, error), workingDir func() string) http.Handler {
+	t.Helper()

 	logger := slogtest.Make(t, &slogtest.Options{
 		IgnoreErrors: true,
 	}).Leveled(slog.LevelDebug)
-	api := agentproc.NewAPI(logger, agentexec.DefaultExecer, updateEnv)
+	api := agentproc.NewAPI(logger, agentexec.DefaultExecer, updateEnv, nil, workingDir)
 	t.Cleanup(func() {
 		_ = api.Close()
 	})
@@ -138,10 +172,10 @@ func waitForExit(t *testing.T, handler http.Handler, id string) workspacesdk.Pro

 // startAndGetID is a helper that starts a process and returns
 // the process ID.
-func startAndGetID(t *testing.T, handler http.Handler, req workspacesdk.StartProcessRequest) string {
+func startAndGetID(t *testing.T, handler http.Handler, req workspacesdk.StartProcessRequest, headers ...http.Header) string {
 	t.Helper()

-	w := postStart(t, handler, req)
+	w := postStart(t, handler, req, headers...)
 	require.Equal(t, http.StatusOK, w.Code)

 	var resp workspacesdk.StartProcessResponse
@@ -244,6 +278,100 @@ func TestStartProcess(t *testing.T) {
 		require.Contains(t, resp.Output, "marker.txt")
 	})

+	t.Run("DefaultWorkDirIsHome", func(t *testing.T) {
+		t.Parallel()
+
+		// No working directory closure, so the process
+		// should fall back to $HOME. We verify through
+		// the process list API which reports the resolved
+		// working directory using native OS paths,
+		// avoiding shell path format mismatches on
+		// Windows (Git Bash returns POSIX paths).
+		handler := newTestAPI(t)
+
+		homeDir, err := os.UserHomeDir()
+		require.NoError(t, err)
+
+		id := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command: "echo ok",
+		})
+
+		resp := waitForExit(t, handler, id)
+		require.NotNil(t, resp.ExitCode)
+		require.Equal(t, 0, *resp.ExitCode)
+
+		w := getList(t, handler)
+		require.Equal(t, http.StatusOK, w.Code)
+		var listResp workspacesdk.ListProcessesResponse
+		require.NoError(t, json.NewDecoder(w.Body).Decode(&listResp))
+		var proc *workspacesdk.ProcessInfo
+		for i := range listResp.Processes {
+			if listResp.Processes[i].ID == id {
+				proc = &listResp.Processes[i]
+				break
+			}
+		}
+		require.NotNil(t, proc, "process not found in list")
+		require.Equal(t, homeDir, proc.WorkDir)
+	})
+
+	t.Run("DefaultWorkDirFromClosure", func(t *testing.T) {
+		t.Parallel()
+
+		// The closure provides a valid directory, so the
+		// process should start there. Use the marker file
+		// pattern to avoid path format mismatches on
+		// Windows.
+		tmpDir := t.TempDir()
+		handler := newTestAPIWithOptions(t, nil, func() string {
+			return tmpDir
+		})
+
+		id := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command: "touch marker.txt && ls marker.txt",
+		})
+
+		resp := waitForExit(t, handler, id)
+		require.NotNil(t, resp.ExitCode)
+		require.Equal(t, 0, *resp.ExitCode)
+		require.Contains(t, resp.Output, "marker.txt")
+	})
+
+	t.Run("DefaultWorkDirClosureNonExistentFallsBackToHome", func(t *testing.T) {
+		t.Parallel()
+
+		// The closure returns a path that doesn't exist,
+		// so the process should fall back to $HOME.
+		handler := newTestAPIWithOptions(t, nil, func() string {
+			return "/tmp/nonexistent-dir-" + fmt.Sprintf("%d", time.Now().UnixNano())
+		})
+
+		homeDir, err := os.UserHomeDir()
+		require.NoError(t, err)
+
+		id := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command: "echo ok",
+		})
+
+		resp := waitForExit(t, handler, id)
+		require.NotNil(t, resp.ExitCode)
+		require.Equal(t, 0, *resp.ExitCode)
+
+		w := getList(t, handler)
+		require.Equal(t, http.StatusOK, w.Code)
+		var listResp workspacesdk.ListProcessesResponse
+		require.NoError(t, json.NewDecoder(w.Body).Decode(&listResp))
+		var proc *workspacesdk.ProcessInfo
+		for i := range listResp.Processes {
+			if listResp.Processes[i].ID == id {
+				proc = &listResp.Processes[i]
+				break
+			}
+		}
+		require.NotNil(t, proc, "process not found in list")
+		require.Equal(t, homeDir, proc.WorkDir)
+	})
+
 	t.Run("CustomEnv", func(t *testing.T) {
 		t.Parallel()

@@ -331,6 +459,180 @@ func TestListProcesses(t *testing.T) {
 		require.Empty(t, resp.Processes)
 	})

+	t.Run("FilterByChatID", func(t *testing.T) {
+		t.Parallel()
+
+		handler := newTestAPI(t)
+
+		chatA := uuid.New().String()
+		chatB := uuid.New().String()
+		headersA := http.Header{workspacesdk.CoderChatIDHeader: {chatA}}
+		headersB := http.Header{workspacesdk.CoderChatIDHeader: {chatB}}
+
+		// Start processes with different chat IDs.
+		id1 := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command: "echo chat-a",
+		}, headersA)
+		waitForExit(t, handler, id1)
+
+		id2 := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command: "echo chat-b",
+		}, headersB)
+		waitForExit(t, handler, id2)
+
+		id3 := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command: "echo chat-a-2",
+		}, headersA)
+		waitForExit(t, handler, id3)
+
+		// List with chat A header should return 2 processes.
+		w := getListWithChatHeader(t, handler, chatA)
+		require.Equal(t, http.StatusOK, w.Code)
+
+		var resp workspacesdk.ListProcessesResponse
+		err := json.NewDecoder(w.Body).Decode(&resp)
+		require.NoError(t, err)
+		require.Len(t, resp.Processes, 2)
+
+		ids := make(map[string]bool)
+		for _, p := range resp.Processes {
+			ids[p.ID] = true
+		}
+		require.True(t, ids[id1])
+		require.True(t, ids[id3])
+
+		// List with chat B header should return 1 process.
+		w2 := getListWithChatHeader(t, handler, chatB)
+		require.Equal(t, http.StatusOK, w2.Code)
+
+		var resp2 workspacesdk.ListProcessesResponse
+		err = json.NewDecoder(w2.Body).Decode(&resp2)
+		require.NoError(t, err)
+		require.Len(t, resp2.Processes, 1)
+		require.Equal(t, id2, resp2.Processes[0].ID)
+
+		// List without chat header should return all 3.
+		w3 := getList(t, handler)
+		require.Equal(t, http.StatusOK, w3.Code)
+
+		var resp3 workspacesdk.ListProcessesResponse
+		err = json.NewDecoder(w3.Body).Decode(&resp3)
+		require.NoError(t, err)
+		require.Len(t, resp3.Processes, 3)
+	})
+
+	t.Run("ChatIDFiltering", func(t *testing.T) {
+		t.Parallel()
+
+		handler := newTestAPI(t)
+		chatID := uuid.New().String()
+		headers := http.Header{workspacesdk.CoderChatIDHeader: {chatID}}
+
+		id := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command: "echo with-chat",
+		}, headers)
+		waitForExit(t, handler, id)
+
+		// Listing with the same chat header should return
+		// the process.
+		w := getListWithChatHeader(t, handler, chatID)
+		require.Equal(t, http.StatusOK, w.Code)
+
+		var resp workspacesdk.ListProcessesResponse
+		err := json.NewDecoder(w.Body).Decode(&resp)
+		require.NoError(t, err)
+		require.Len(t, resp.Processes, 1)
+		require.Equal(t, id, resp.Processes[0].ID)
+
+		// Listing with a different chat header should not
+		// return the process.
+		w2 := getListWithChatHeader(t, handler, uuid.New().String())
+		require.Equal(t, http.StatusOK, w2.Code)
+
+		var resp2 workspacesdk.ListProcessesResponse
+		err = json.NewDecoder(w2.Body).Decode(&resp2)
+		require.NoError(t, err)
+		require.Empty(t, resp2.Processes)
+
+		// Listing without a chat header should return the
+		// process (no filtering).
+		w3 := getList(t, handler)
+		require.Equal(t, http.StatusOK, w3.Code)
+
+		var resp3 workspacesdk.ListProcessesResponse
+		err = json.NewDecoder(w3.Body).Decode(&resp3)
+		require.NoError(t, err)
+		require.Len(t, resp3.Processes, 1)
+	})
+
+	t.Run("SortAndLimit", func(t *testing.T) {
+		t.Parallel()
+
+		handler := newTestAPI(t)
+
+		// Start 12 short-lived processes so we exceed the
+		// limit of 10.
+		for i := 0; i < 12; i++ {
+			id := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+				Command: fmt.Sprintf("echo proc-%d", i),
+			})
+			waitForExit(t, handler, id)
+		}
+
+		w := getList(t, handler)
+		require.Equal(t, http.StatusOK, w.Code)
+
+		var resp workspacesdk.ListProcessesResponse
+		err := json.NewDecoder(w.Body).Decode(&resp)
+		require.NoError(t, err)
+		require.Len(t, resp.Processes, 10, "should be capped at 10")
+
+		// All returned processes are exited, so they should
+		// be sorted by StartedAt descending (newest first).
+		for i := 1; i < len(resp.Processes); i++ {
+			require.GreaterOrEqual(t, resp.Processes[i-1].StartedAt, resp.Processes[i].StartedAt,
+				"processes should be sorted by started_at descending")
+		}
+	})
+
+	t.Run("RunningProcessesSortedFirst", func(t *testing.T) {
+		t.Parallel()
+
+		handler := newTestAPI(t)
+
+		// Start an exited process first.
+		exitedID := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command: "echo done",
+		})
+		waitForExit(t, handler, exitedID)
+
+		// Start a running process after.
+		runningID := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command:    "sleep 300",
+			Background: true,
+		})
+
+		w := getList(t, handler)
+		require.Equal(t, http.StatusOK, w.Code)
+
+		var resp workspacesdk.ListProcessesResponse
+		err := json.NewDecoder(w.Body).Decode(&resp)
+		require.NoError(t, err)
+		require.Len(t, resp.Processes, 2)
+
+		// Running process should come first regardless of
+		// start order.
+		require.Equal(t, runningID, resp.Processes[0].ID)
+		require.True(t, resp.Processes[0].Running)
+		require.Equal(t, exitedID, resp.Processes[1].ID)
+		require.False(t, resp.Processes[1].Running)
+
+		// Clean up.
+		postSignal(t, handler, runningID, workspacesdk.SignalProcessRequest{
+			Signal: "kill",
+		})
+	})
+
 	t.Run("MixedRunningAndExited", func(t *testing.T) {
 		t.Parallel()

@@ -379,6 +681,23 @@ func TestListProcesses(t *testing.T) {
 	})
 }

+// getListWithChatHeader sends a GET /list request with the
+// Coder-Chat-Id header set and returns the recorder.
+func getListWithChatHeader(t *testing.T, handler http.Handler, chatID string) *httptest.ResponseRecorder {
+	t.Helper()
+
+	ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
+	defer cancel()
+
+	w := httptest.NewRecorder()
+	r := httptest.NewRequestWithContext(ctx, http.MethodGet, "/list", nil)
+	if chatID != "" {
+		r.Header.Set(workspacesdk.CoderChatIDHeader, chatID)
+	}
+	handler.ServeHTTP(w, r)
+	return w
+}
+
 func TestProcessOutput(t *testing.T) {
 	t.Parallel()

@@ -437,6 +756,161 @@ func TestProcessOutput(t *testing.T) {
 		require.NoError(t, err)
 		require.Contains(t, resp.Message, "not found")
 	})
+
+	t.Run("ChatIDEnforcement", func(t *testing.T) {
+		t.Parallel()
+
+		handler := newTestAPI(t)
+
+		// Start a process with chat-a.
+		chatA := uuid.New()
+		id := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command:    "echo secret",
+			Background: true,
+		}, http.Header{
+			workspacesdk.CoderChatIDHeader: {chatA.String()},
+		})
+		waitForExit(t, handler, id)
+
+		// Chat-b should NOT see this process.
+		chatB := uuid.New()
+		w1 := getOutputWithHeaders(t, handler, id, http.Header{
+			workspacesdk.CoderChatIDHeader: {chatB.String()},
+		})
+		require.Equal(t, http.StatusNotFound, w1.Code)
+
+		// Without any chat ID header, should return 200
+		// (backwards compatible).
+		w2 := getOutput(t, handler, id)
+		require.Equal(t, http.StatusOK, w2.Code)
+	})
+
+	t.Run("WaitForExit", func(t *testing.T) {
+		t.Parallel()
+
+		handler := newTestAPI(t)
+
+		id := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command: "echo hello-wait && sleep 0.1",
+		})
+
+		w := getOutputWithWait(t, handler, id)
+		require.Equal(t, http.StatusOK, w.Code)
+
+		var resp workspacesdk.ProcessOutputResponse
+		err := json.NewDecoder(w.Body).Decode(&resp)
+		require.NoError(t, err)
+		require.False(t, resp.Running)
+		require.NotNil(t, resp.ExitCode)
+		require.Equal(t, 0, *resp.ExitCode)
+		require.Contains(t, resp.Output, "hello-wait")
+	})
+
+	t.Run("WaitAlreadyExited", func(t *testing.T) {
+		t.Parallel()
+
+		handler := newTestAPI(t)
+
+		id := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command: "echo done",
+		})
+
+		waitForExit(t, handler, id)
+
+		w := getOutputWithWait(t, handler, id)
+		require.Equal(t, http.StatusOK, w.Code)
+
+		var resp workspacesdk.ProcessOutputResponse
+		err := json.NewDecoder(w.Body).Decode(&resp)
+		require.NoError(t, err)
+		require.False(t, resp.Running)
+		require.Contains(t, resp.Output, "done")
+	})
+
+	t.Run("WaitTimeout", func(t *testing.T) {
+		t.Parallel()
+
+		handler := newTestAPI(t)
+
+		id := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command:    "sleep 300",
+			Background: true,
+		})
+
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.IntervalMedium)
+		defer cancel()
+
+		w := getOutputWithWaitCtx(ctx, t, handler, id)
+		require.Equal(t, http.StatusOK, w.Code)
+
+		var resp workspacesdk.ProcessOutputResponse
+		err := json.NewDecoder(w.Body).Decode(&resp)
+		require.NoError(t, err)
+		require.True(t, resp.Running)
+
+		// Kill and wait for the process so cleanup does
+		// not hang.
+		postSignal(
+			t, handler, id,
+			workspacesdk.SignalProcessRequest{Signal: "kill"},
+		)
+		waitForExit(t, handler, id)
+	})
+
+	t.Run("ConcurrentWaiters", func(t *testing.T) {
+		t.Parallel()
+
+		handler := newTestAPI(t)
+
+		id := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command:    "sleep 300",
+			Background: true,
+		})
+
+		var (
+			wg    sync.WaitGroup
+			resps [2]workspacesdk.ProcessOutputResponse
+			codes [2]int
+		)
+		for i := range 2 {
+			wg.Add(1)
+			go func() {
+				defer wg.Done()
+				w := getOutputWithWait(t, handler, id)
+				codes[i] = w.Code
+				_ = json.NewDecoder(w.Body).Decode(&resps[i])
+			}()
+		}
+
+		// Signal the process to exit so both waiters unblock.
+		postSignal(
+			t, handler, id,
+			workspacesdk.SignalProcessRequest{Signal: "kill"},
+		)
+
+		wg.Wait()
+
+		for i := range 2 {
+			require.Equal(t, http.StatusOK, codes[i], "waiter %d", i)
+			require.False(t, resps[i].Running, "waiter %d", i)
+		}
+	})
+}
+
+func getOutputWithWait(t *testing.T, handler http.Handler, id string) *httptest.ResponseRecorder {
+	t.Helper()
+	ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
+	defer cancel()
+	return getOutputWithWaitCtx(ctx, t, handler, id)
+}
+
+func getOutputWithWaitCtx(ctx context.Context, t *testing.T, handler http.Handler, id string) *httptest.ResponseRecorder {
+	t.Helper()
+	path := fmt.Sprintf("/%s/output?wait=true", id)
+	req := httptest.NewRequestWithContext(ctx, http.MethodGet, path, nil)
+	w := httptest.NewRecorder()
+	handler.ServeHTTP(w, req)
+	return w
 }

 func TestSignalProcess(t *testing.T) {
@@ -570,6 +1044,46 @@ func TestSignalProcess(t *testing.T) {
 	})
 }

+func TestHandleStartProcess_ChatHeaders_EmptyWorkDir_StillNotifies(t *testing.T) {
+	t.Parallel()
+
+	pathStore := agentgit.NewPathStore()
+	chatID := uuid.New()
+	ch, unsub := pathStore.Subscribe(chatID)
+	defer unsub()
+
+	logger := slogtest.Make(t, nil).Leveled(slog.LevelDebug)
+	api := agentproc.NewAPI(logger, agentexec.DefaultExecer, func(current []string) ([]string, error) {
+		return current, nil
+	}, pathStore, nil)
+	defer api.Close()
+
+	routes := api.Routes()
+
+	body, err := json.Marshal(workspacesdk.StartProcessRequest{
+		Command: "echo hello",
+	})
+	require.NoError(t, err)
+
+	req := httptest.NewRequest(http.MethodPost, "/start", bytes.NewReader(body))
+	req.Header.Set(workspacesdk.CoderChatIDHeader, chatID.String())
+	rw := httptest.NewRecorder()
+	routes.ServeHTTP(rw, req)
+
+	require.Equal(t, http.StatusOK, rw.Code)
+
+	// The subscriber should be notified even though no paths
+	// were added.
+	select {
+	case <-ch:
+	case <-time.After(testutil.WaitShort):
+		t.Fatal("timed out waiting for path store notification")
+	}
+
+	// No paths should have been stored for this chat.
+	require.Nil(t, pathStore.GetPaths(chatID))
+}
+
 func TestProcessLifecycle(t *testing.T) {
 	t.Parallel()

@@ -39,11 +39,13 @@ const (
 // how much output is written.
 type HeadTailBuffer struct {
 	mu         sync.Mutex
+	cond       *sync.Cond
 	head       []byte
 	tail       []byte
 	tailPos    int
 	tailFull   bool
 	headFull   bool
+	closed     bool
 	totalBytes int
 	maxHead    int
 	maxTail    int
@@ -52,20 +54,24 @@ type HeadTailBuffer struct {
 // NewHeadTailBuffer creates a new HeadTailBuffer with the
 // default head and tail sizes.
 func NewHeadTailBuffer() *HeadTailBuffer {
-	return &HeadTailBuffer{
+	b := &HeadTailBuffer{
 		maxHead: MaxHeadBytes,
 		maxTail: MaxTailBytes,
 	}
+	b.cond = sync.NewCond(&b.mu)
+	return b
 }

 // NewHeadTailBufferSized creates a HeadTailBuffer with custom
 // head and tail sizes. This is useful for testing truncation
 // logic with smaller buffers.
 func NewHeadTailBufferSized(maxHead, maxTail int) *HeadTailBuffer {
-	return &HeadTailBuffer{
+	b := &HeadTailBuffer{
 		maxHead: maxHead,
 		maxTail: maxTail,
 	}
+	b.cond = sync.NewCond(&b.mu)
+	return b
 }

 // Write implements io.Writer. It is safe for concurrent use.
@@ -296,6 +302,15 @@ func truncateLines(s string) string {
 	return b.String()
 }

+// Close marks the buffer as closed and wakes any waiters.
+// This is called when the process exits.
+func (b *HeadTailBuffer) Close() {
+	b.mu.Lock()
+	defer b.mu.Unlock()
+	b.closed = true
+	b.cond.Broadcast()
+}
+
 // Reset clears the buffer, discarding all data.
 func (b *HeadTailBuffer) Reset() {
 	b.mu.Lock()
@@ -305,5 +320,7 @@ func (b *HeadTailBuffer) Reset() {
 	b.tailPos = 0
 	b.tailFull = false
 	b.headFull = false
+	b.closed = false
 	b.totalBytes = 0
+	b.cond.Broadcast()
 }
@@ -0,0 +1,26 @@
+//go:build !windows
+
+package agentproc
+
+import (
+	"os"
+	"syscall"
+)
+
+// procSysProcAttr returns the SysProcAttr to use when spawning
+// processes. On Unix, Setpgid creates a new process group so
+// that signals can be delivered to the entire group (the shell
+// and all its children).
+func procSysProcAttr() *syscall.SysProcAttr {
+	return &syscall.SysProcAttr{
+		Setpgid: true,
+	}
+}
+
+// signalProcess sends a signal to the process group rooted at p.
+// Using the negative PID sends the signal to every process in the
+// group, ensuring child processes (e.g. from shell pipelines) are
+// also signaled.
+func signalProcess(p *os.Process, sig syscall.Signal) error {
+	return syscall.Kill(-p.Pid, sig)
+}
@@ -0,0 +1,20 @@
+package agentproc
+
+import (
+	"os"
+	"syscall"
+)
+
+// procSysProcAttr returns the SysProcAttr to use when spawning
+// processes. On Windows, process groups are not supported in the
+// same way as Unix, so this returns an empty struct.
+func procSysProcAttr() *syscall.SysProcAttr {
+	return &syscall.SysProcAttr{}
+}
+
+// signalProcess sends a signal directly to the process. Windows
+// does not support process group signaling, so we fall back to
+// sending the signal to the process itself.
+func signalProcess(p *os.Process, _ syscall.Signal) error {
+	return p.Kill()
+}
@@ -21,6 +21,10 @@ import (
 var (
 	errProcessNotFound   = xerrors.New("process not found")
 	errProcessNotRunning = xerrors.New("process is not running")
+
+	// exitedProcessReapAge is how long an exited process is
+	// kept before being automatically removed from the map.
+	exitedProcessReapAge = 5 * time.Minute
 )

 // process represents a running or completed process.
@@ -30,6 +34,7 @@ type process struct {
 	command    string
 	workDir    string
 	background bool
+	chatID     string
 	cmd        *exec.Cmd
 	cancel     context.CancelFunc
 	buf        *HeadTailBuffer
@@ -65,23 +70,25 @@ func (p *process) output() (string, *workspacesdk.ProcessTruncation) {

 // manager tracks processes spawned by the agent.
 type manager struct {
-	mu        sync.Mutex
-	logger    slog.Logger
-	execer    agentexec.Execer
-	clock     quartz.Clock
-	procs     map[string]*process
-	closed    bool
-	updateEnv func(current []string) (updated []string, err error)
+	mu         sync.Mutex
+	logger     slog.Logger
+	execer     agentexec.Execer
+	clock      quartz.Clock
+	procs      map[string]*process
+	closed     bool
+	updateEnv  func(current []string) (updated []string, err error)
+	workingDir func() string
 }

 // newManager creates a new process manager.
-func newManager(logger slog.Logger, execer agentexec.Execer, updateEnv func(current []string) (updated []string, err error)) *manager {
+func newManager(logger slog.Logger, execer agentexec.Execer, updateEnv func(current []string) (updated []string, err error), workingDir func() string) *manager {
 	return &manager{
-		logger:    logger,
-		execer:    execer,
-		clock:     quartz.NewReal(),
-		procs:     make(map[string]*process),
-		updateEnv: updateEnv,
+		logger:     logger,
+		execer:     execer,
+		clock:      quartz.NewReal(),
+		procs:      make(map[string]*process),
+		updateEnv:  updateEnv,
+		workingDir: workingDir,
 	}
 }

@@ -89,7 +96,7 @@ func newManager(logger slog.Logger, execer agentexec.Execer, updateEnv func(curr
 // processes use a long-lived context so the process survives
 // the HTTP request lifecycle. The background flag only affects
 // client-side polling behavior.
-func (m *manager) start(req workspacesdk.StartProcessRequest) (*process, error) {
+func (m *manager) start(req workspacesdk.StartProcessRequest, chatID string) (*process, error) {
 	m.mu.Lock()
 	if m.closed {
 		m.mu.Unlock()
@@ -104,10 +111,9 @@ func (m *manager) start(req workspacesdk.StartProcessRequest) (*process, error)
 	// the process is not tied to any HTTP request.
 	ctx, cancel := context.WithCancel(context.Background())
 	cmd := m.execer.CommandContext(ctx, "sh", "-c", req.Command)
-	if req.WorkDir != "" {
-		cmd.Dir = req.WorkDir
-	}
+	cmd.Dir = m.resolveWorkDir(req.WorkDir)
 	cmd.Stdin = nil
+	cmd.SysProcAttr = procSysProcAttr()

 	// WaitDelay ensures cmd.Wait returns promptly after
 	// the process is killed, even if child processes are
@@ -152,8 +158,9 @@ func (m *manager) start(req workspacesdk.StartProcessRequest) (*process, error)
 	proc := &process{
 		id:         id,
 		command:    req.Command,
-		workDir:    req.WorkDir,
+		workDir:    cmd.Dir,
 		background: req.Background,
+		chatID:     chatID,
 		cmd:        cmd,
 		cancel:     cancel,
 		buf:        buf,
@@ -201,6 +208,9 @@ func (m *manager) start(req workspacesdk.StartProcessRequest) (*process, error)
 		proc.exitCode = &code
 		proc.mu.Unlock()

+		// Wake any waiters blocked on new output or
+		// process exit before closing the done channel.
+		proc.buf.Close()
 		close(proc.done)
 	}()

@@ -215,14 +225,32 @@ func (m *manager) get(id string) (*process, bool) {
 	return proc, ok
 }

-// list returns info about all tracked processes.
-func (m *manager) list() []workspacesdk.ProcessInfo {
+// list returns info about all tracked processes. Exited
+// processes older than exitedProcessReapAge are removed.
+// If chatID is non-empty, only processes belonging to that
+// chat are returned.
+func (m *manager) list(chatID string) []workspacesdk.ProcessInfo {
 	m.mu.Lock()
 	defer m.mu.Unlock()

+	now := m.clock.Now()
 	infos := make([]workspacesdk.ProcessInfo, 0, len(m.procs))
-	for _, proc := range m.procs {
-		infos = append(infos, proc.info())
+	for id, proc := range m.procs {
+		info := proc.info()
+		// Reap processes that exited more than 5 minutes ago
+		// to prevent unbounded map growth.
+		if !info.Running && info.ExitedAt != nil {
+			exitedAt := time.Unix(*info.ExitedAt, 0)
+			if now.Sub(exitedAt) > exitedProcessReapAge {
+				delete(m.procs, id)
+				continue
+			}
+		}
+		// Filter by chatID if provided.
+		if chatID != "" && proc.chatID != chatID {
+			continue
+		}
+		infos = append(infos, info)
 	}
 	return infos
 }
@@ -248,13 +276,15 @@ func (m *manager) signal(id string, sig string) error {

 	switch sig {
 	case "kill":
-		if err := proc.cmd.Process.Kill(); err != nil {
+		// Use process group kill to ensure child processes
+		// (e.g. from shell pipelines) are also killed.
+		if err := signalProcess(proc.cmd.Process, syscall.SIGKILL); err != nil {
 			return xerrors.Errorf("kill process: %w", err)
 		}
 	case "terminate":
-		//nolint:revive // syscall.SIGTERM is portable enough
-		// for our supported platforms.
-		if err := proc.cmd.Process.Signal(syscall.SIGTERM); err != nil {
+		// Use process group signal to ensure child processes
+		// are also terminated.
+		if err := signalProcess(proc.cmd.Process, syscall.SIGTERM); err != nil {
 			return xerrors.Errorf("terminate process: %w", err)
 		}
 	default:
@@ -292,3 +322,54 @@ func (m *manager) Close() error {

 	return nil
 }
+
+// waitForOutput blocks until the buffer is closed (process
+// exited) or the context is canceled. Returns nil when the
+// buffer closed, ctx.Err() when the context expired.
+func (p *process) waitForOutput(ctx context.Context) error {
+	p.buf.cond.L.Lock()
+	defer p.buf.cond.L.Unlock()
+
+	nevermind := make(chan struct{})
+	defer close(nevermind)
+	go func() {
+		select {
+		case <-ctx.Done():
+			// Acquire the lock before broadcasting to
+			// guarantee the waiter has entered cond.Wait()
+			// (which atomically releases the lock).
+			// Without this, a Broadcast between the loop
+			// predicate check and cond.Wait() is lost.
+			p.buf.cond.L.Lock()
+			defer p.buf.cond.L.Unlock()
+			p.buf.cond.Broadcast()
+		case <-nevermind:
+		}
+	}()
+
+	for ctx.Err() == nil && !p.buf.closed {
+		p.buf.cond.Wait()
+	}
+	return ctx.Err()
+}
+
+// resolveWorkDir returns the directory a process should start in.
+// Priority: explicit request dir > agent configured dir > $HOME.
+// Falls through when a candidate is empty or does not exist on
+// disk, matching the behavior of SSH sessions.
+func (m *manager) resolveWorkDir(requested string) string {
+	if requested != "" {
+		return requested
+	}
+	if m.workingDir != nil {
+		if dir := m.workingDir(); dir != "" {
+			if info, err := os.Stat(dir); err == nil && info.IsDir() {
+				return dir
+			}
+		}
+	}
+	if home, err := os.UserHomeDir(); err == nil {
+		return home
+	}
+	return ""
+}
@@ -398,11 +398,11 @@ func (r *Runner) run(ctx context.Context, script codersdk.WorkspaceAgentScript,
 				},
 			})
 			if err != nil {
-				logger.Error(ctx, fmt.Sprintf("reporting script completed: %s", err.Error()))
+				logger.Warn(ctx, "reporting script completed", slog.Error(err))
 			}
 		})
 		if err != nil {
-			logger.Error(ctx, fmt.Sprintf("reporting script completed: track command goroutine: %s", err.Error()))
+			logger.Warn(ctx, "reporting script completed: track command goroutine", slog.Error(err))
 		}
 	}()

@@ -8,6 +8,7 @@ import (
 	"storj.io/drpc/drpcconn"

 	"github.com/coder/coder/v2/agent/agentsocket/proto"
+	agentproto "github.com/coder/coder/v2/agent/proto"
 	"github.com/coder/coder/v2/agent/unit"
 )

@@ -132,6 +133,11 @@ func (c *Client) SyncStatus(ctx context.Context, unitName unit.ID) (SyncStatusRe
 	}, nil
 }

+// UpdateAppStatus forwards an app status update to coderd via the agent.
+func (c *Client) UpdateAppStatus(ctx context.Context, req *agentproto.UpdateAppStatusRequest) (*agentproto.UpdateAppStatusResponse, error) {
+	return c.client.UpdateAppStatus(ctx, req)
+}
+
 // SyncStatusResponse contains the status information for a unit.
 type SyncStatusResponse struct {
 	UnitName     unit.ID          `table:"unit,default_sort" json:"unit_name"`
@@ -7,6 +7,7 @@
 package proto

 import (
+	proto "github.com/coder/coder/v2/agent/proto"
 	protoreflect "google.golang.org/protobuf/reflect/protoreflect"
 	protoimpl "google.golang.org/protobuf/runtime/protoimpl"
 	reflect "reflect"
@@ -649,90 +650,98 @@ var file_agent_agentsocket_proto_agentsocket_proto_rawDesc = []byte{
 	0x6b, 0x65, 0x74, 0x2f, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x2f, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73,
 	0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x12, 0x14, 0x63, 0x6f, 0x64,
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-	0x63, 0x6f, 0x64, 0x65, 0x72, 0x2f, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2f, 0x76, 0x32, 0x2f, 0x61,
-	0x67, 0x65, 0x6e, 0x74, 0x2f, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74,
-	0x2f, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x62, 0x06, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x33,
+	0x79, 0x6e, 0x63, 0x53, 0x74, 0x61, 0x74, 0x75, 0x73, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74,
+	0x1a, 0x28, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f,
+	0x63, 0x6b, 0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x53, 0x79, 0x6e, 0x63, 0x53, 0x74, 0x61, 0x74,
+	0x75, 0x73, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x12, 0x62, 0x0a, 0x0f, 0x55, 0x70,
+	0x64, 0x61, 0x74, 0x65, 0x41, 0x70, 0x70, 0x53, 0x74, 0x61, 0x74, 0x75, 0x73, 0x12, 0x26, 0x2e,
+	0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x2e, 0x76, 0x32, 0x2e, 0x55,
+	0x70, 0x64, 0x61, 0x74, 0x65, 0x41, 0x70, 0x70, 0x53, 0x74, 0x61, 0x74, 0x75, 0x73, 0x52, 0x65,
+	0x71, 0x75, 0x65, 0x73, 0x74, 0x1a, 0x27, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61, 0x67,
+	0x65, 0x6e, 0x74, 0x2e, 0x76, 0x32, 0x2e, 0x55, 0x70, 0x64, 0x61, 0x74, 0x65, 0x41, 0x70, 0x70,
+	0x53, 0x74, 0x61, 0x74, 0x75, 0x73, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x42, 0x33,
+	0x5a, 0x31, 0x67, 0x69, 0x74, 0x68, 0x75, 0x62, 0x2e, 0x63, 0x6f, 0x6d, 0x2f, 0x63, 0x6f, 0x64,
+	0x65, 0x72, 0x2f, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2f, 0x76, 0x32, 0x2f, 0x61, 0x67, 0x65, 0x6e,
+	0x74, 0x2f, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2f, 0x70, 0x72,
+	0x6f, 0x74, 0x6f, 0x62, 0x06, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x33,
 }

 var (
@@ -749,19 +758,21 @@ func file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP() []byte {

 var file_agent_agentsocket_proto_agentsocket_proto_msgTypes = make([]protoimpl.MessageInfo, 13)
 var file_agent_agentsocket_proto_agentsocket_proto_goTypes = []interface{}{
-	(*PingRequest)(nil),          // 0: coder.agentsocket.v1.PingRequest
-	(*PingResponse)(nil),         // 1: coder.agentsocket.v1.PingResponse
-	(*SyncStartRequest)(nil),     // 2: coder.agentsocket.v1.SyncStartRequest
-	(*SyncStartResponse)(nil),    // 3: coder.agentsocket.v1.SyncStartResponse
-	(*SyncWantRequest)(nil),      // 4: coder.agentsocket.v1.SyncWantRequest
-	(*SyncWantResponse)(nil),     // 5: coder.agentsocket.v1.SyncWantResponse
-	(*SyncCompleteRequest)(nil),  // 6: coder.agentsocket.v1.SyncCompleteRequest
-	(*SyncCompleteResponse)(nil), // 7: coder.agentsocket.v1.SyncCompleteResponse
-	(*SyncReadyRequest)(nil),     // 8: coder.agentsocket.v1.SyncReadyRequest
-	(*SyncReadyResponse)(nil),    // 9: coder.agentsocket.v1.SyncReadyResponse
-	(*SyncStatusRequest)(nil),    // 10: coder.agentsocket.v1.SyncStatusRequest
-	(*DependencyInfo)(nil),       // 11: coder.agentsocket.v1.DependencyInfo
-	(*SyncStatusResponse)(nil),   // 12: coder.agentsocket.v1.SyncStatusResponse
+	(*PingRequest)(nil),                   // 0: coder.agentsocket.v1.PingRequest
+	(*PingResponse)(nil),                  // 1: coder.agentsocket.v1.PingResponse
+	(*SyncStartRequest)(nil),              // 2: coder.agentsocket.v1.SyncStartRequest
+	(*SyncStartResponse)(nil),             // 3: coder.agentsocket.v1.SyncStartResponse
+	(*SyncWantRequest)(nil),               // 4: coder.agentsocket.v1.SyncWantRequest
+	(*SyncWantResponse)(nil),              // 5: coder.agentsocket.v1.SyncWantResponse
+	(*SyncCompleteRequest)(nil),           // 6: coder.agentsocket.v1.SyncCompleteRequest
+	(*SyncCompleteResponse)(nil),          // 7: coder.agentsocket.v1.SyncCompleteResponse
+	(*SyncReadyRequest)(nil),              // 8: coder.agentsocket.v1.SyncReadyRequest
+	(*SyncReadyResponse)(nil),             // 9: coder.agentsocket.v1.SyncReadyResponse
+	(*SyncStatusRequest)(nil),             // 10: coder.agentsocket.v1.SyncStatusRequest
+	(*DependencyInfo)(nil),                // 11: coder.agentsocket.v1.DependencyInfo
+	(*SyncStatusResponse)(nil),            // 12: coder.agentsocket.v1.SyncStatusResponse
+	(*proto.UpdateAppStatusRequest)(nil),  // 13: coder.agent.v2.UpdateAppStatusRequest
+	(*proto.UpdateAppStatusResponse)(nil), // 14: coder.agent.v2.UpdateAppStatusResponse
 }
 var file_agent_agentsocket_proto_agentsocket_proto_depIdxs = []int32{
 	11, // 0: coder.agentsocket.v1.SyncStatusResponse.dependencies:type_name -> coder.agentsocket.v1.DependencyInfo
@@ -771,14 +782,16 @@ var file_agent_agentsocket_proto_agentsocket_proto_depIdxs = []int32{
 	6,  // 4: coder.agentsocket.v1.AgentSocket.SyncComplete:input_type -> coder.agentsocket.v1.SyncCompleteRequest
 	8,  // 5: coder.agentsocket.v1.AgentSocket.SyncReady:input_type -> coder.agentsocket.v1.SyncReadyRequest
 	10, // 6: coder.agentsocket.v1.AgentSocket.SyncStatus:input_type -> coder.agentsocket.v1.SyncStatusRequest
-	1,  // 7: coder.agentsocket.v1.AgentSocket.Ping:output_type -> coder.agentsocket.v1.PingResponse
-	3,  // 8: coder.agentsocket.v1.AgentSocket.SyncStart:output_type -> coder.agentsocket.v1.SyncStartResponse
-	5,  // 9: coder.agentsocket.v1.AgentSocket.SyncWant:output_type -> coder.agentsocket.v1.SyncWantResponse
-	7,  // 10: coder.agentsocket.v1.AgentSocket.SyncComplete:output_type -> coder.agentsocket.v1.SyncCompleteResponse
-	9,  // 11: coder.agentsocket.v1.AgentSocket.SyncReady:output_type -> coder.agentsocket.v1.SyncReadyResponse
-	12, // 12: coder.agentsocket.v1.AgentSocket.SyncStatus:output_type -> coder.agentsocket.v1.SyncStatusResponse
-	7,  // [7:13] is the sub-list for method output_type
-	1,  // [1:7] is the sub-list for method input_type
+	13, // 7: coder.agentsocket.v1.AgentSocket.UpdateAppStatus:input_type -> coder.agent.v2.UpdateAppStatusRequest
+	1,  // 8: coder.agentsocket.v1.AgentSocket.Ping:output_type -> coder.agentsocket.v1.PingResponse
+	3,  // 9: coder.agentsocket.v1.AgentSocket.SyncStart:output_type -> coder.agentsocket.v1.SyncStartResponse
+	5,  // 10: coder.agentsocket.v1.AgentSocket.SyncWant:output_type -> coder.agentsocket.v1.SyncWantResponse
+	7,  // 11: coder.agentsocket.v1.AgentSocket.SyncComplete:output_type -> coder.agentsocket.v1.SyncCompleteResponse
+	9,  // 12: coder.agentsocket.v1.AgentSocket.SyncReady:output_type -> coder.agentsocket.v1.SyncReadyResponse
+	12, // 13: coder.agentsocket.v1.AgentSocket.SyncStatus:output_type -> coder.agentsocket.v1.SyncStatusResponse
+	14, // 14: coder.agentsocket.v1.AgentSocket.UpdateAppStatus:output_type -> coder.agent.v2.UpdateAppStatusResponse
+	8,  // [8:15] is the sub-list for method output_type
+	1,  // [1:8] is the sub-list for method input_type
 	1,  // [1:1] is the sub-list for extension type_name
 	1,  // [1:1] is the sub-list for extension extendee
 	0,  // [0:1] is the sub-list for field type_name
@@ -3,6 +3,8 @@ option go_package = "github.com/coder/coder/v2/agent/agentsocket/proto";

 package coder.agentsocket.v1;

+import "agent/proto/agent.proto";
+
 message PingRequest {}

 message PingResponse {}
@@ -66,4 +68,6 @@ service AgentSocket {
  rpc SyncReady(SyncReadyRequest) returns (SyncReadyResponse);
  // Get the status of a unit and list its dependencies.
  rpc SyncStatus(SyncStatusRequest) returns (SyncStatusResponse);
+  // Update app status, forwarded to coderd.
+  rpc UpdateAppStatus(coder.agent.v2.UpdateAppStatusRequest) returns (coder.agent.v2.UpdateAppStatusResponse);
 }
@@ -7,6 +7,7 @@ package proto
 import (
 	context "context"
 	errors "errors"
+	proto1 "github.com/coder/coder/v2/agent/proto"
 	protojson "google.golang.org/protobuf/encoding/protojson"
 	proto "google.golang.org/protobuf/proto"
 	drpc "storj.io/drpc"
@@ -44,6 +45,7 @@ type DRPCAgentSocketClient interface {
 	SyncComplete(ctx context.Context, in *SyncCompleteRequest) (*SyncCompleteResponse, error)
 	SyncReady(ctx context.Context, in *SyncReadyRequest) (*SyncReadyResponse, error)
 	SyncStatus(ctx context.Context, in *SyncStatusRequest) (*SyncStatusResponse, error)
+	UpdateAppStatus(ctx context.Context, in *proto1.UpdateAppStatusRequest) (*proto1.UpdateAppStatusResponse, error)
 }

 type drpcAgentSocketClient struct {
@@ -110,6 +112,15 @@ func (c *drpcAgentSocketClient) SyncStatus(ctx context.Context, in *SyncStatusRe
 	return out, nil
 }

+func (c *drpcAgentSocketClient) UpdateAppStatus(ctx context.Context, in *proto1.UpdateAppStatusRequest) (*proto1.UpdateAppStatusResponse, error) {
+	out := new(proto1.UpdateAppStatusResponse)
+	err := c.cc.Invoke(ctx, "/coder.agentsocket.v1.AgentSocket/UpdateAppStatus", drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{}, in, out)
+	if err != nil {
+		return nil, err
+	}
+	return out, nil
+}
+
 type DRPCAgentSocketServer interface {
 	Ping(context.Context, *PingRequest) (*PingResponse, error)
 	SyncStart(context.Context, *SyncStartRequest) (*SyncStartResponse, error)
@@ -117,6 +128,7 @@ type DRPCAgentSocketServer interface {
 	SyncComplete(context.Context, *SyncCompleteRequest) (*SyncCompleteResponse, error)
 	SyncReady(context.Context, *SyncReadyRequest) (*SyncReadyResponse, error)
 	SyncStatus(context.Context, *SyncStatusRequest) (*SyncStatusResponse, error)
+	UpdateAppStatus(context.Context, *proto1.UpdateAppStatusRequest) (*proto1.UpdateAppStatusResponse, error)
 }

 type DRPCAgentSocketUnimplementedServer struct{}
@@ -145,9 +157,13 @@ func (s *DRPCAgentSocketUnimplementedServer) SyncStatus(context.Context, *SyncSt
 	return nil, drpcerr.WithCode(errors.New("Unimplemented"), drpcerr.Unimplemented)
 }

+func (s *DRPCAgentSocketUnimplementedServer) UpdateAppStatus(context.Context, *proto1.UpdateAppStatusRequest) (*proto1.UpdateAppStatusResponse, error) {
+	return nil, drpcerr.WithCode(errors.New("Unimplemented"), drpcerr.Unimplemented)
+}
+
 type DRPCAgentSocketDescription struct{}

-func (DRPCAgentSocketDescription) NumMethods() int { return 6 }
+func (DRPCAgentSocketDescription) NumMethods() int { return 7 }

 func (DRPCAgentSocketDescription) Method(n int) (string, drpc.Encoding, drpc.Receiver, interface{}, bool) {
 	switch n {
@@ -205,6 +221,15 @@ func (DRPCAgentSocketDescription) Method(n int) (string, drpc.Encoding, drpc.Rec
 						in1.(*SyncStatusRequest),
 					)
 			}, DRPCAgentSocketServer.SyncStatus, true
+	case 6:
+		return "/coder.agentsocket.v1.AgentSocket/UpdateAppStatus", drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{},
+			func(srv interface{}, ctx context.Context, in1, in2 interface{}) (drpc.Message, error) {
+				return srv.(DRPCAgentSocketServer).
+					UpdateAppStatus(
+						ctx,
+						in1.(*proto1.UpdateAppStatusRequest),
+					)
+			}, DRPCAgentSocketServer.UpdateAppStatus, true
 	default:
 		return "", nil, nil, nil, false
 	}
@@ -309,3 +334,19 @@ func (x *drpcAgentSocket_SyncStatusStream) SendAndClose(m *SyncStatusResponse) e
 	}
 	return x.CloseSend()
 }
+
+type DRPCAgentSocket_UpdateAppStatusStream interface {
+	drpc.Stream
+	SendAndClose(*proto1.UpdateAppStatusResponse) error
+}
+
+type drpcAgentSocket_UpdateAppStatusStream struct {
+	drpc.Stream
+}
+
+func (x *drpcAgentSocket_UpdateAppStatusStream) SendAndClose(m *proto1.UpdateAppStatusResponse) error {
+	if err := x.MsgSend(m, drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{}); err != nil {
+		return err
+	}
+	return x.CloseSend()
+}
@@ -8,10 +8,13 @@ import "github.com/coder/coder/v2/apiversion"
 //   - Initial release
 //   - Ping
 //   - Sync operations: SyncStart, SyncWant, SyncComplete, SyncWait, SyncStatus
+//
+// API v1.1:
+//   - UpdateAppStatus RPC (forwarded to coderd)

 const (
 	CurrentMajor = 1
-	CurrentMinor = 0
+	CurrentMinor = 1
 )

 var CurrentVersion = apiversion.New(CurrentMajor, CurrentMinor)
@@ -12,6 +12,7 @@ import (

 	"cdr.dev/slog/v3"
 	"github.com/coder/coder/v2/agent/agentsocket/proto"
+	agentproto "github.com/coder/coder/v2/agent/proto"
 	"github.com/coder/coder/v2/agent/unit"
 	"github.com/coder/coder/v2/codersdk/drpcsdk"
 )
@@ -120,6 +121,17 @@ func (s *Server) Close() error {
 	return nil
 }

+// SetAgentAPI sets the agent API client used to forward requests
+// to coderd.
+func (s *Server) SetAgentAPI(api agentproto.DRPCAgentClient28) {
+	s.service.SetAgentAPI(api)
+}
+
+// ClearAgentAPI clears the agent API client.
+func (s *Server) ClearAgentAPI() {
+	s.service.ClearAgentAPI()
+}
+
 func (s *Server) acceptConnections() {
 	// In an edge case, Close() might race with acceptConnections() and set s.listener to nil.
 	// Therefore, we grab a copy of the listener under a lock. We might still get a nil listener,
@@ -3,22 +3,46 @@ package agentsocket
 import (
 	"context"
 	"errors"
+	"sync"

 	"golang.org/x/xerrors"

 	"cdr.dev/slog/v3"
 	"github.com/coder/coder/v2/agent/agentsocket/proto"
+	agentproto "github.com/coder/coder/v2/agent/proto"
 	"github.com/coder/coder/v2/agent/unit"
 )

 var _ proto.DRPCAgentSocketServer = (*DRPCAgentSocketService)(nil)

-var ErrUnitManagerNotAvailable = xerrors.New("unit manager not available")
+var (
+	ErrUnitManagerNotAvailable = xerrors.New("unit manager not available")
+	ErrAgentAPINotConnected    = xerrors.New("agent not connected to coderd")
+)

 // DRPCAgentSocketService implements the DRPC agent socket service.
 type DRPCAgentSocketService struct {
 	unitManager *unit.Manager
 	logger      slog.Logger
+
+	mu       sync.Mutex
+	agentAPI agentproto.DRPCAgentClient28
+}
+
+// SetAgentAPI sets the agent API client used to forward requests
+// to coderd. This is called when the agent connects to coderd.
+func (s *DRPCAgentSocketService) SetAgentAPI(api agentproto.DRPCAgentClient28) {
+	s.mu.Lock()
+	defer s.mu.Unlock()
+	s.agentAPI = api
+}
+
+// ClearAgentAPI clears the agent API client. This is called when
+// the agent disconnects from coderd.
+func (s *DRPCAgentSocketService) ClearAgentAPI() {
+	s.mu.Lock()
+	defer s.mu.Unlock()
+	s.agentAPI = nil
 }

 // Ping responds to a ping request to check if the service is alive.
@@ -150,3 +174,16 @@ func (s *DRPCAgentSocketService) SyncStatus(_ context.Context, req *proto.SyncSt
 		Dependencies: depInfos,
 	}, nil
 }
+
+// UpdateAppStatus forwards an app status update to coderd via the
+// agent API. Returns an error if the agent is not connected.
+func (s *DRPCAgentSocketService) UpdateAppStatus(ctx context.Context, req *agentproto.UpdateAppStatusRequest) (*agentproto.UpdateAppStatusResponse, error) {
+	s.mu.Lock()
+	api := s.agentAPI
+	s.mu.Unlock()
+
+	if api == nil {
+		return nil, ErrAgentAPINotConnected
+	}
+	return api.UpdateAppStatus(ctx, req)
+}
@@ -5,13 +5,26 @@ import (
 	"testing"

 	"github.com/stretchr/testify/require"
+	"golang.org/x/xerrors"

 	"cdr.dev/slog/v3"
 	"github.com/coder/coder/v2/agent/agentsocket"
+	agentproto "github.com/coder/coder/v2/agent/proto"
 	"github.com/coder/coder/v2/agent/unit"
 	"github.com/coder/coder/v2/testutil"
 )

+// fakeAgentAPI implements just the UpdateAppStatus method of
+// DRPCAgentClient28 for testing. Calling any other method will panic.
+type fakeAgentAPI struct {
+	agentproto.DRPCAgentClient28
+	updateAppStatus func(context.Context, *agentproto.UpdateAppStatusRequest) (*agentproto.UpdateAppStatusResponse, error)
+}
+
+func (m *fakeAgentAPI) UpdateAppStatus(ctx context.Context, req *agentproto.UpdateAppStatusRequest) (*agentproto.UpdateAppStatusResponse, error) {
+	return m.updateAppStatus(ctx, req)
+}
+
 // newSocketClient creates a DRPC client connected to the Unix socket at the given path.
 func newSocketClient(ctx context.Context, t *testing.T, socketPath string) *agentsocket.Client {
 	t.Helper()
@@ -351,4 +364,128 @@ func TestDRPCAgentSocketService(t *testing.T) {
 			require.True(t, ready)
 		})
 	})
+
+	t.Run("UpdateAppStatus", func(t *testing.T) {
+		t.Parallel()
+
+		t.Run("NotConnected", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := testutil.AgentSocketPath(t)
+			ctx := testutil.Context(t, testutil.WaitShort)
+			server, err := agentsocket.NewServer(
+				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(ctx, t, socketPath)
+
+			_, err = client.UpdateAppStatus(ctx, &agentproto.UpdateAppStatusRequest{
+				Slug:    "test-app",
+				State:   agentproto.UpdateAppStatusRequest_WORKING,
+				Message: "doing stuff",
+			})
+			require.ErrorContains(t, err, "not connected")
+		})
+
+		t.Run("ForwardsToAgentAPI", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := testutil.AgentSocketPath(t)
+			ctx := testutil.Context(t, testutil.WaitShort)
+			server, err := agentsocket.NewServer(
+				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			var gotReq *agentproto.UpdateAppStatusRequest
+			mock := &fakeAgentAPI{
+				updateAppStatus: func(_ context.Context, req *agentproto.UpdateAppStatusRequest) (*agentproto.UpdateAppStatusResponse, error) {
+					gotReq = req
+					return &agentproto.UpdateAppStatusResponse{}, nil
+				},
+			}
+			server.SetAgentAPI(mock)
+
+			client := newSocketClient(ctx, t, socketPath)
+
+			resp, err := client.UpdateAppStatus(ctx, &agentproto.UpdateAppStatusRequest{
+				Slug:    "test-app",
+				State:   agentproto.UpdateAppStatusRequest_IDLE,
+				Message: "all done",
+				Uri:     "https://example.com",
+			})
+			require.NoError(t, err)
+			require.NotNil(t, resp)
+
+			require.NotNil(t, gotReq)
+			require.Equal(t, "test-app", gotReq.Slug)
+			require.Equal(t, agentproto.UpdateAppStatusRequest_IDLE, gotReq.State)
+			require.Equal(t, "all done", gotReq.Message)
+			require.Equal(t, "https://example.com", gotReq.Uri)
+		})
+
+		t.Run("ForwardsError", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := testutil.AgentSocketPath(t)
+			ctx := testutil.Context(t, testutil.WaitShort)
+			server, err := agentsocket.NewServer(
+				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			mock := &fakeAgentAPI{
+				updateAppStatus: func(context.Context, *agentproto.UpdateAppStatusRequest) (*agentproto.UpdateAppStatusResponse, error) {
+					return nil, xerrors.New("app not found")
+				},
+			}
+			server.SetAgentAPI(mock)
+
+			client := newSocketClient(ctx, t, socketPath)
+
+			_, err = client.UpdateAppStatus(ctx, &agentproto.UpdateAppStatusRequest{
+				Slug:    "nonexistent",
+				State:   agentproto.UpdateAppStatusRequest_WORKING,
+				Message: "testing",
+			})
+			require.ErrorContains(t, err, "app not found")
+		})
+
+		t.Run("ClearAgentAPI", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := testutil.AgentSocketPath(t)
+			ctx := testutil.Context(t, testutil.WaitShort)
+			server, err := agentsocket.NewServer(
+				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			mock := &fakeAgentAPI{
+				updateAppStatus: func(context.Context, *agentproto.UpdateAppStatusRequest) (*agentproto.UpdateAppStatusResponse, error) {
+					return &agentproto.UpdateAppStatusResponse{}, nil
+				},
+			}
+			server.SetAgentAPI(mock)
+			server.ClearAgentAPI()
+
+			client := newSocketClient(ctx, t, socketPath)
+
+			_, err = client.UpdateAppStatus(ctx, &agentproto.UpdateAppStatusRequest{
+				Slug:    "test-app",
+				State:   agentproto.UpdateAppStatusRequest_WORKING,
+				Message: "should fail",
+			})
+			require.ErrorContains(t, err, "not connected")
+		})
+	})
 }
@@ -110,6 +110,11 @@ type Config struct {
 	// X11DisplayOffset is the offset to add to the X11 display number.
 	// Default is 10.
 	X11DisplayOffset *int
+	// X11MaxPort overrides the highest port used for X11 forwarding
+	// listeners. Defaults to X11MaxPort (6200). Useful in tests
+	// to shrink the port range and reduce the number of sessions
+	// required.
+	X11MaxPort *int
 	// BlockFileTransfer restricts use of file transfer applications.
 	BlockFileTransfer bool
 	// ReportConnection.
@@ -158,6 +163,10 @@ func NewServer(ctx context.Context, logger slog.Logger, prometheusRegistry *prom
 		offset := X11DefaultDisplayOffset
 		config.X11DisplayOffset = &offset
 	}
+	if config.X11MaxPort == nil {
+		maxPort := X11MaxPort
+		config.X11MaxPort = &maxPort
+	}
 	if config.UpdateEnv == nil {
 		config.UpdateEnv = func(current []string) ([]string, error) { return current, nil }
 	}
@@ -201,6 +210,7 @@ func NewServer(ctx context.Context, logger slog.Logger, prometheusRegistry *prom
 			x11HandlerErrors: metrics.x11HandlerErrors,
 			fs:               fs,
 			displayOffset:    *config.X11DisplayOffset,
+			maxPort:          *config.X11MaxPort,
 			sessions:         make(map[*x11Session]struct{}),
 			connections:      make(map[net.Conn]struct{}),
 			network: func() X11Network {
@@ -57,6 +57,7 @@ type x11Forwarder struct {
 	x11HandlerErrors *prometheus.CounterVec
 	fs               afero.Fs
 	displayOffset    int
+	maxPort          int

 	// network creates X11 listener sockets. Defaults to osNet{}.
 	network X11Network
@@ -314,7 +315,7 @@ func (x *x11Forwarder) evictLeastRecentlyUsedSession() {
 // the next available port starting from X11StartPort and displayOffset.
 func (x *x11Forwarder) createX11Listener(ctx context.Context) (ln net.Listener, display int, err error) {
 	// Look for an open port to listen on.
-	for port := X11StartPort + x.displayOffset; port <= X11MaxPort; port++ {
+	for port := X11StartPort + x.displayOffset; port <= x.maxPort; port++ {
 		if ctx.Err() != nil {
 			return nil, -1, ctx.Err()
 		}
@@ -142,8 +142,13 @@ func TestServer_X11_EvictionLRU(t *testing.T) {
 	// Use in-process networking for X11 forwarding.
 	inproc := testutil.NewInProcNet()

+	// Limit port range so we only need a handful of sessions to fill it
+	// (the default 190 ports may easily timeout or conflict with other
+	// ports on the system).
+	maxPort := agentssh.X11StartPort + agentssh.X11DefaultDisplayOffset + 5
 	cfg := &agentssh.Config{
-		X11Net: inproc,
+		X11Net:     inproc,
+		X11MaxPort: &maxPort,
 	}

 	s, err := agentssh.NewServer(ctx, logger, prometheus.NewRegistry(), fs, agentexec.DefaultExecer, cfg)
@@ -172,7 +177,7 @@ func TestServer_X11_EvictionLRU(t *testing.T) {
 	// configured port range.

 	startPort := agentssh.X11StartPort + agentssh.X11DefaultDisplayOffset
-	maxSessions := agentssh.X11MaxPort - startPort + 1 - 1 // -1 for the blocked port
+	maxSessions := maxPort - startPort + 1 - 1 // -1 for the blocked port
 	require.Greater(t, maxSessions, 0, "expected a positive maxSessions value")

 	// shellSession holds references to the session and its standard streams so
@@ -24,6 +24,7 @@ func New(t testing.TB, coderURL *url.URL, agentToken string, opts ...func(*agent
 	var o agent.Options
 	log := testutil.Logger(t).Named("agent")
 	o.Logger = log
+	o.SocketPath = testutil.AgentSocketPath(t)

 	for _, opt := range opts {
 		opt(&o)
@@ -28,7 +28,10 @@ func (a *agent) apiHandler() http.Handler {
 	})

 	r.Mount("/api/v0", a.filesAPI.Routes())
+	r.Mount("/api/v0/git", a.gitAPI.Routes())
 	r.Mount("/api/v0/processes", a.processAPI.Routes())
+	r.Mount("/api/v0/desktop", a.desktopAPI.Routes())
+	r.Mount("/api/v0/mcp", a.mcpAPI.Routes())

 	if a.devcontainers {
 		r.Mount("/api/v0/containers", a.containerAPI.Routes())
@@ -6,10 +6,10 @@ import (
 	"context"
 	"net"
 	"path/filepath"
-	"sync"
 	"testing"

 	"github.com/google/uuid"
+	"github.com/prometheus/client_golang/prometheus"
 	"github.com/stretchr/testify/require"
 	"google.golang.org/protobuf/proto"
 	"google.golang.org/protobuf/types/known/timestamppb"
@@ -22,26 +22,6 @@ import (
 	"github.com/coder/coder/v2/testutil"
 )

-// logSink captures structured log entries for testing.
-type logSink struct {
-	mu      sync.Mutex
-	entries []slog.SinkEntry
-}
-
-func (s *logSink) LogEntry(_ context.Context, e slog.SinkEntry) {
-	s.mu.Lock()
-	defer s.mu.Unlock()
-	s.entries = append(s.entries, e)
-}
-
-func (*logSink) Sync() {}
-
-func (s *logSink) getEntries() []slog.SinkEntry {
-	s.mu.Lock()
-	defer s.mu.Unlock()
-	return append([]slog.SinkEntry{}, s.entries...)
-}
-
 // getField returns the value of a field by name from a slog.Map.
 func getField(fields slog.Map, name string) interface{} {
 	for _, f := range fields {
@@ -69,14 +49,14 @@ func TestBoundaryLogs_EndToEnd(t *testing.T) {
 	t.Parallel()

 	socketPath := filepath.Join(testutil.TempDirUnixSocket(t), "boundary.sock")
-	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath)
+	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath, prometheus.NewRegistry())

 	err := srv.Start()
 	require.NoError(t, err)
 	t.Cleanup(func() { require.NoError(t, srv.Close()) })

-	sink := &logSink{}
-	logger := slog.Make(sink)
+	sink := testutil.NewFakeSink(t)
+	logger := sink.Logger(slog.LevelInfo)
 	workspaceID := uuid.New()
 	templateID := uuid.New()
 	templateVersionID := uuid.New()
@@ -117,10 +97,10 @@ func TestBoundaryLogs_EndToEnd(t *testing.T) {
 	sendBoundaryLogsRequest(t, conn, req)

 	require.Eventually(t, func() bool {
-		return len(sink.getEntries()) >= 1
+		return len(sink.Entries()) >= 1
 	}, testutil.WaitShort, testutil.IntervalFast)

-	entries := sink.getEntries()
+	entries := sink.Entries()
 	require.Len(t, entries, 1)
 	entry := entries[0]
 	require.Equal(t, slog.LevelInfo, entry.Level)
@@ -151,10 +131,10 @@ func TestBoundaryLogs_EndToEnd(t *testing.T) {
 	sendBoundaryLogsRequest(t, conn, req2)

 	require.Eventually(t, func() bool {
-		return len(sink.getEntries()) >= 2
+		return len(sink.Entries()) >= 2
 	}, testutil.WaitShort, testutil.IntervalFast)

-	entries = sink.getEntries()
+	entries = sink.Entries()
 	entry = entries[1]
 	require.Len(t, entries, 2)
 	require.Equal(t, slog.LevelInfo, entry.Level)
@@ -0,0 +1,286 @@
+// Code generated by protoc-gen-go. DO NOT EDIT.
+// versions:
+// 	protoc-gen-go v1.30.0
+// 	protoc        v4.23.4
+// source: agent/boundarylogproxy/codec/boundary.proto
+
+package codec
+
+import (
+	proto "github.com/coder/coder/v2/agent/proto"
+	protoreflect "google.golang.org/protobuf/reflect/protoreflect"
+	protoimpl "google.golang.org/protobuf/runtime/protoimpl"
+	reflect "reflect"
+	sync "sync"
+)
+
+const (
+	// Verify that this generated code is sufficiently up-to-date.
+	_ = protoimpl.EnforceVersion(20 - protoimpl.MinVersion)
+	// Verify that runtime/protoimpl is sufficiently up-to-date.
+	_ = protoimpl.EnforceVersion(protoimpl.MaxVersion - 20)
+)
+
+// BoundaryMessage is the envelope for all TagV2 messages sent over the
+// boundary <-> agent unix socket. TagV1 carries a bare
+// ReportBoundaryLogsRequest for backwards compatibility; TagV2 wraps
+// everything in this envelope so the protocol can be extended with new
+// message types without adding more tags.
+type BoundaryMessage struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+
+	// Types that are assignable to Msg:
+	//
+	//	*BoundaryMessage_Logs
+	//	*BoundaryMessage_Status
+	Msg isBoundaryMessage_Msg `protobuf_oneof:"msg"`
+}
+
+func (x *BoundaryMessage) Reset() {
+	*x = BoundaryMessage{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_agent_boundarylogproxy_codec_boundary_proto_msgTypes[0]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *BoundaryMessage) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*BoundaryMessage) ProtoMessage() {}
+
+func (x *BoundaryMessage) ProtoReflect() protoreflect.Message {
+	mi := &file_agent_boundarylogproxy_codec_boundary_proto_msgTypes[0]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use BoundaryMessage.ProtoReflect.Descriptor instead.
+func (*BoundaryMessage) Descriptor() ([]byte, []int) {
+	return file_agent_boundarylogproxy_codec_boundary_proto_rawDescGZIP(), []int{0}
+}
+
+func (m *BoundaryMessage) GetMsg() isBoundaryMessage_Msg {
+	if m != nil {
+		return m.Msg
+	}
+	return nil
+}
+
+func (x *BoundaryMessage) GetLogs() *proto.ReportBoundaryLogsRequest {
+	if x, ok := x.GetMsg().(*BoundaryMessage_Logs); ok {
+		return x.Logs
+	}
+	return nil
+}
+
+func (x *BoundaryMessage) GetStatus() *BoundaryStatus {
+	if x, ok := x.GetMsg().(*BoundaryMessage_Status); ok {
+		return x.Status
+	}
+	return nil
+}
+
+type isBoundaryMessage_Msg interface {
+	isBoundaryMessage_Msg()
+}
+
+type BoundaryMessage_Logs struct {
+	Logs *proto.ReportBoundaryLogsRequest `protobuf:"bytes,1,opt,name=logs,proto3,oneof"`
+}
+
+type BoundaryMessage_Status struct {
+	Status *BoundaryStatus `protobuf:"bytes,2,opt,name=status,proto3,oneof"`
+}
+
+func (*BoundaryMessage_Logs) isBoundaryMessage_Msg() {}
+
+func (*BoundaryMessage_Status) isBoundaryMessage_Msg() {}
+
+// BoundaryStatus carries operational metadata from boundary to the agent.
+// The agent records these values as Prometheus metrics. This message is
+// never forwarded to coderd.
+type BoundaryStatus struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+
+	// Logs dropped because boundary's internal channel buffer was full.
+	DroppedChannelFull int64 `protobuf:"varint,1,opt,name=dropped_channel_full,json=droppedChannelFull,proto3" json:"dropped_channel_full,omitempty"`
+	// Logs dropped because boundary's batch buffer was full after a
+	// failed flush attempt.
+	DroppedBatchFull int64 `protobuf:"varint,2,opt,name=dropped_batch_full,json=droppedBatchFull,proto3" json:"dropped_batch_full,omitempty"`
+}
+
+func (x *BoundaryStatus) Reset() {
+	*x = BoundaryStatus{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_agent_boundarylogproxy_codec_boundary_proto_msgTypes[1]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *BoundaryStatus) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*BoundaryStatus) ProtoMessage() {}
+
+func (x *BoundaryStatus) ProtoReflect() protoreflect.Message {
+	mi := &file_agent_boundarylogproxy_codec_boundary_proto_msgTypes[1]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use BoundaryStatus.ProtoReflect.Descriptor instead.
+func (*BoundaryStatus) Descriptor() ([]byte, []int) {
+	return file_agent_boundarylogproxy_codec_boundary_proto_rawDescGZIP(), []int{1}
+}
+
+func (x *BoundaryStatus) GetDroppedChannelFull() int64 {
+	if x != nil {
+		return x.DroppedChannelFull
+	}
+	return 0
+}
+
+func (x *BoundaryStatus) GetDroppedBatchFull() int64 {
+	if x != nil {
+		return x.DroppedBatchFull
+	}
+	return 0
+}
+
+var File_agent_boundarylogproxy_codec_boundary_proto protoreflect.FileDescriptor
+
+var file_agent_boundarylogproxy_codec_boundary_proto_rawDesc = []byte{
+	0x0a, 0x2b, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x2f, 0x62, 0x6f, 0x75, 0x6e, 0x64, 0x61, 0x72, 0x79,
+	0x6c, 0x6f, 0x67, 0x70, 0x72, 0x6f, 0x78, 0x79, 0x2f, 0x63, 0x6f, 0x64, 0x65, 0x63, 0x2f, 0x62,
+	0x6f, 0x75, 0x6e, 0x64, 0x61, 0x72, 0x79, 0x2e, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x12, 0x1f, 0x63,
+	0x6f, 0x64, 0x65, 0x72, 0x2e, 0x62, 0x6f, 0x75, 0x6e, 0x64, 0x61, 0x72, 0x79, 0x6c, 0x6f, 0x67,
+	0x70, 0x72, 0x6f, 0x78, 0x79, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x63, 0x2e, 0x76, 0x31, 0x1a, 0x17,
+	0x61, 0x67, 0x65, 0x6e, 0x74, 0x2f, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x2f, 0x61, 0x67, 0x65, 0x6e,
+	0x74, 0x2e, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x22, 0xa4, 0x01, 0x0a, 0x0f, 0x42, 0x6f, 0x75, 0x6e,
+	0x64, 0x61, 0x72, 0x79, 0x4d, 0x65, 0x73, 0x73, 0x61, 0x67, 0x65, 0x12, 0x3f, 0x0a, 0x04, 0x6c,
+	0x6f, 0x67, 0x73, 0x18, 0x01, 0x20, 0x01, 0x28, 0x0b, 0x32, 0x29, 0x2e, 0x63, 0x6f, 0x64, 0x65,
+	0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x2e, 0x76, 0x32, 0x2e, 0x52, 0x65, 0x70, 0x6f, 0x72,
+	0x74, 0x42, 0x6f, 0x75, 0x6e, 0x64, 0x61, 0x72, 0x79, 0x4c, 0x6f, 0x67, 0x73, 0x52, 0x65, 0x71,
+	0x75, 0x65, 0x73, 0x74, 0x48, 0x00, 0x52, 0x04, 0x6c, 0x6f, 0x67, 0x73, 0x12, 0x49, 0x0a, 0x06,
+	0x73, 0x74, 0x61, 0x74, 0x75, 0x73, 0x18, 0x02, 0x20, 0x01, 0x28, 0x0b, 0x32, 0x2f, 0x2e, 0x63,
+	0x6f, 0x64, 0x65, 0x72, 0x2e, 0x62, 0x6f, 0x75, 0x6e, 0x64, 0x61, 0x72, 0x79, 0x6c, 0x6f, 0x67,
+	0x70, 0x72, 0x6f, 0x78, 0x79, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x63, 0x2e, 0x76, 0x31, 0x2e, 0x42,
+	0x6f, 0x75, 0x6e, 0x64, 0x61, 0x72, 0x79, 0x53, 0x74, 0x61, 0x74, 0x75, 0x73, 0x48, 0x00, 0x52,
+	0x06, 0x73, 0x74, 0x61, 0x74, 0x75, 0x73, 0x42, 0x05, 0x0a, 0x03, 0x6d, 0x73, 0x67, 0x22, 0x70,
+	0x0a, 0x0e, 0x42, 0x6f, 0x75, 0x6e, 0x64, 0x61, 0x72, 0x79, 0x53, 0x74, 0x61, 0x74, 0x75, 0x73,
+	0x12, 0x30, 0x0a, 0x14, 0x64, 0x72, 0x6f, 0x70, 0x70, 0x65, 0x64, 0x5f, 0x63, 0x68, 0x61, 0x6e,
+	0x6e, 0x65, 0x6c, 0x5f, 0x66, 0x75, 0x6c, 0x6c, 0x18, 0x01, 0x20, 0x01, 0x28, 0x03, 0x52, 0x12,
+	0x64, 0x72, 0x6f, 0x70, 0x70, 0x65, 0x64, 0x43, 0x68, 0x61, 0x6e, 0x6e, 0x65, 0x6c, 0x46, 0x75,
+	0x6c, 0x6c, 0x12, 0x2c, 0x0a, 0x12, 0x64, 0x72, 0x6f, 0x70, 0x70, 0x65, 0x64, 0x5f, 0x62, 0x61,
+	0x74, 0x63, 0x68, 0x5f, 0x66, 0x75, 0x6c, 0x6c, 0x18, 0x02, 0x20, 0x01, 0x28, 0x03, 0x52, 0x10,
+	0x64, 0x72, 0x6f, 0x70, 0x70, 0x65, 0x64, 0x42, 0x61, 0x74, 0x63, 0x68, 0x46, 0x75, 0x6c, 0x6c,
+	0x42, 0x38, 0x5a, 0x36, 0x67, 0x69, 0x74, 0x68, 0x75, 0x62, 0x2e, 0x63, 0x6f, 0x6d, 0x2f, 0x63,
+	0x6f, 0x64, 0x65, 0x72, 0x2f, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2f, 0x76, 0x32, 0x2f, 0x61, 0x67,
+	0x65, 0x6e, 0x74, 0x2f, 0x62, 0x6f, 0x75, 0x6e, 0x64, 0x61, 0x72, 0x79, 0x6c, 0x6f, 0x67, 0x70,
+	0x72, 0x6f, 0x78, 0x79, 0x2f, 0x63, 0x6f, 0x64, 0x65, 0x63, 0x62, 0x06, 0x70, 0x72, 0x6f, 0x74,
+	0x6f, 0x33,
+}
+
+var (
+	file_agent_boundarylogproxy_codec_boundary_proto_rawDescOnce sync.Once
+	file_agent_boundarylogproxy_codec_boundary_proto_rawDescData = file_agent_boundarylogproxy_codec_boundary_proto_rawDesc
+)
+
+func file_agent_boundarylogproxy_codec_boundary_proto_rawDescGZIP() []byte {
+	file_agent_boundarylogproxy_codec_boundary_proto_rawDescOnce.Do(func() {
+		file_agent_boundarylogproxy_codec_boundary_proto_rawDescData = protoimpl.X.CompressGZIP(file_agent_boundarylogproxy_codec_boundary_proto_rawDescData)
+	})
+	return file_agent_boundarylogproxy_codec_boundary_proto_rawDescData
+}
+
+var file_agent_boundarylogproxy_codec_boundary_proto_msgTypes = make([]protoimpl.MessageInfo, 2)
+var file_agent_boundarylogproxy_codec_boundary_proto_goTypes = []interface{}{
+	(*BoundaryMessage)(nil),                 // 0: coder.boundarylogproxy.codec.v1.BoundaryMessage
+	(*BoundaryStatus)(nil),                  // 1: coder.boundarylogproxy.codec.v1.BoundaryStatus
+	(*proto.ReportBoundaryLogsRequest)(nil), // 2: coder.agent.v2.ReportBoundaryLogsRequest
+}
+var file_agent_boundarylogproxy_codec_boundary_proto_depIdxs = []int32{
+	2, // 0: coder.boundarylogproxy.codec.v1.BoundaryMessage.logs:type_name -> coder.agent.v2.ReportBoundaryLogsRequest
+	1, // 1: coder.boundarylogproxy.codec.v1.BoundaryMessage.status:type_name -> coder.boundarylogproxy.codec.v1.BoundaryStatus
+	2, // [2:2] is the sub-list for method output_type
+	2, // [2:2] is the sub-list for method input_type
+	2, // [2:2] is the sub-list for extension type_name
+	2, // [2:2] is the sub-list for extension extendee
+	0, // [0:2] is the sub-list for field type_name
+}
+
+func init() { file_agent_boundarylogproxy_codec_boundary_proto_init() }
+func file_agent_boundarylogproxy_codec_boundary_proto_init() {
+	if File_agent_boundarylogproxy_codec_boundary_proto != nil {
+		return
+	}
+	if !protoimpl.UnsafeEnabled {
+		file_agent_boundarylogproxy_codec_boundary_proto_msgTypes[0].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*BoundaryMessage); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+		file_agent_boundarylogproxy_codec_boundary_proto_msgTypes[1].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*BoundaryStatus); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+	}
+	file_agent_boundarylogproxy_codec_boundary_proto_msgTypes[0].OneofWrappers = []interface{}{
+		(*BoundaryMessage_Logs)(nil),
+		(*BoundaryMessage_Status)(nil),
+	}
+	type x struct{}
+	out := protoimpl.TypeBuilder{
+		File: protoimpl.DescBuilder{
+			GoPackagePath: reflect.TypeOf(x{}).PkgPath(),
+			RawDescriptor: file_agent_boundarylogproxy_codec_boundary_proto_rawDesc,
+			NumEnums:      0,
+			NumMessages:   2,
+			NumExtensions: 0,
+			NumServices:   0,
+		},
+		GoTypes:           file_agent_boundarylogproxy_codec_boundary_proto_goTypes,
+		DependencyIndexes: file_agent_boundarylogproxy_codec_boundary_proto_depIdxs,
+		MessageInfos:      file_agent_boundarylogproxy_codec_boundary_proto_msgTypes,
+	}.Build()
+	File_agent_boundarylogproxy_codec_boundary_proto = out.File
+	file_agent_boundarylogproxy_codec_boundary_proto_rawDesc = nil
+	file_agent_boundarylogproxy_codec_boundary_proto_goTypes = nil
+	file_agent_boundarylogproxy_codec_boundary_proto_depIdxs = nil
+}
@@ -0,0 +1,29 @@
+syntax = "proto3";
+option go_package = "github.com/coder/coder/v2/agent/boundarylogproxy/codec";
+
+package coder.boundarylogproxy.codec.v1;
+
+import "agent/proto/agent.proto";
+
+// BoundaryMessage is the envelope for all TagV2 messages sent over the
+// boundary <-> agent unix socket. TagV1 carries a bare
+// ReportBoundaryLogsRequest for backwards compatibility; TagV2 wraps
+// everything in this envelope so the protocol can be extended with new
+// message types without adding more tags.
+message BoundaryMessage {
+	oneof msg {
+		coder.agent.v2.ReportBoundaryLogsRequest logs = 1;
+		BoundaryStatus status = 2;
+	}
+}
+
+// BoundaryStatus carries operational metadata from boundary to the agent.
+// The agent records these values as Prometheus metrics. This message is
+// never forwarded to coderd.
+message BoundaryStatus {
+	// Logs dropped because boundary's internal channel buffer was full.
+	int64 dropped_channel_full = 1;
+	// Logs dropped because boundary's batch buffer was full after a
+	// failed flush attempt.
+	int64 dropped_batch_full = 2;
+}
@@ -14,14 +14,23 @@ import (
 	"io"

 	"golang.org/x/xerrors"
+	"google.golang.org/protobuf/proto"
+
+	agentproto "github.com/coder/coder/v2/agent/proto"
 )

 type Tag uint8

 const (
-	// TagV1 identifies the first revision of the protocol. This version has a maximum
-	// data length of MaxMessageSizeV1.
+	// TagV1 identifies the first revision of the protocol. The payload is a
+	// bare ReportBoundaryLogsRequest. This version has a maximum data length
+	// of MaxMessageSizeV1.
 	TagV1 Tag = 1
+
+	// TagV2 identifies the second revision of the protocol. The payload is
+	// a BoundaryMessage envelope. This version has a maximum data length of
+	// MaxMessageSizeV2.
+	TagV2 Tag = 2
 )

 const (
@@ -35,6 +44,9 @@ const (
 	// over the wire for the TagV1 tag. While the wire format allows 24 bits for
 	// length, TagV1 only uses 15 bits.
 	MaxMessageSizeV1 uint32 = 1 << 15
+
+	// MaxMessageSizeV2 is the maximum data length for TagV2.
+	MaxMessageSizeV2 = MaxMessageSizeV1
 )

 var (
@@ -48,12 +60,9 @@ var (
 // WriteFrame writes a framed message with the given tag and data. The data
 // must not exceed 2^DataLength in length.
 func WriteFrame(w io.Writer, tag Tag, data []byte) error {
-	var maxSize uint32
-	switch tag {
-	case TagV1:
-		maxSize = MaxMessageSizeV1
-	default:
-		return xerrors.Errorf("%w: %d", ErrUnsupportedTag, tag)
+	maxSize, err := maxSizeForTag(tag)
+	if err != nil {
+		return err
 	}

 	if len(data) > int(maxSize) {
@@ -101,12 +110,9 @@ func ReadFrame(r io.Reader, buf []byte) (Tag, []byte, error) {
 	}
 	tag := Tag(shifted)

-	var maxSize uint32
-	switch tag {
-	case TagV1:
-		maxSize = MaxMessageSizeV1
-	default:
-		return 0, nil, xerrors.Errorf("%w: %d", ErrUnsupportedTag, tag)
+	maxSize, err := maxSizeForTag(tag)
+	if err != nil {
+		return 0, nil, err
 	}

 	if length > maxSize {
@@ -125,3 +131,56 @@ func ReadFrame(r io.Reader, buf []byte) (Tag, []byte, error) {

 	return tag, buf[:length], nil
 }
+
+// maxSizeForTag returns the maximum payload size for the given tag.
+func maxSizeForTag(tag Tag) (uint32, error) {
+	switch tag {
+	case TagV1:
+		return MaxMessageSizeV1, nil
+	case TagV2:
+		return MaxMessageSizeV2, nil
+	default:
+		return 0, xerrors.Errorf("%w: %d", ErrUnsupportedTag, tag)
+	}
+}
+
+// ReadMessage reads a framed message and unmarshals it based on tag. The
+// returned buf should be passed back on the next call for buffer reuse.
+func ReadMessage(r io.Reader, buf []byte) (proto.Message, []byte, error) {
+	tag, data, err := ReadFrame(r, buf)
+	if err != nil {
+		return nil, data, err
+	}
+
+	var msg proto.Message
+	switch tag {
+	case TagV1:
+		var req agentproto.ReportBoundaryLogsRequest
+		if err := proto.Unmarshal(data, &req); err != nil {
+			return nil, data, xerrors.Errorf("unmarshal TagV1: %w", err)
+		}
+		msg = &req
+	case TagV2:
+		var envelope BoundaryMessage
+		if err := proto.Unmarshal(data, &envelope); err != nil {
+			return nil, data, xerrors.Errorf("unmarshal TagV2: %w", err)
+		}
+		msg = &envelope
+	default:
+		// maxSizeForTag already rejects unknown tags during ReadFrame,
+		// but handle it here for safety.
+		return nil, data, xerrors.Errorf("%w: %d", ErrUnsupportedTag, tag)
+	}
+
+	return msg, data, nil
+}
+
+// WriteMessage marshals a proto message and writes it as a framed message
+// with the given tag.
+func WriteMessage(w io.Writer, tag Tag, msg proto.Message) error {
+	data, err := proto.Marshal(msg)
+	if err != nil {
+		return xerrors.Errorf("marshal: %w", err)
+	}
+	return WriteFrame(w, tag, data)
+}
@@ -89,7 +89,7 @@ func TestReadFrameInvalidTag(t *testing.T) {
 	// reading the invalid tag.
 	const (
 		dataLength uint32 = 10
-		bogusTag   uint32 = 2
+		bogusTag   uint32 = 222
 	)
 	header := bogusTag<<codec.DataLength | dataLength
 	data := make([]byte, 4)
@@ -139,7 +139,7 @@ func TestWriteFrameInvalidTag(t *testing.T) {

 	var buf bytes.Buffer
 	data := make([]byte, 1)
-	const bogusTag = 2
+	const bogusTag = 222
 	err := codec.WriteFrame(&buf, codec.Tag(bogusTag), data)
 	require.ErrorIs(t, err, codec.ErrUnsupportedTag)
 }
@@ -0,0 +1,77 @@
+package boundarylogproxy
+
+import "github.com/prometheus/client_golang/prometheus"
+
+// Metrics tracks observability for the boundary -> agent -> coderd audit log
+// pipeline.
+//
+// Audit logs from boundary workspaces pass through several async buffers
+// before reaching coderd, and any stage can silently drop data. These
+// metrics make that loss visible so operators/devs can:
+//
+//   - Bubble up data loss: a non-zero drop rate means audit logs are being
+//     lost, which may have auditing implications.
+//   - Identify the bottleneck: the reason label pinpoints where drops
+//     occur: boundary's internal buffers, the agent's channel, or the
+//     RPC to coderd.
+//   - Tune buffer sizes: sustained "buffer_full" drops indicate the
+//     agent's channel (or boundary's batch buffer) is too small for the
+//     workload. Combined with batches_forwarded_total you can compute a
+//     drop rate: drops / (drops + forwards).
+//   - Detect batch forwarding issues: "forward_failed" drops increase when
+//     the agent cannot reach coderd.
+//
+// Drops are captured at two stages:
+//   - Agent-side: the agent's channel buffer overflows (reason
+//     "buffer_full") or the RPC forward to coderd fails (reason
+//     "forward_failed").
+//   - Boundary-reported: boundary self-reports drops via BoundaryStatus
+//     messages (reasons "boundary_channel_full", "boundary_batch_full").
+//     These arrive on the next successful flush from boundary.
+//
+// There are circumstances where metrics could be lost e.g., agent restarts,
+// boundary crashes, or the agent shuts down when the DRPC connection is down.
+type Metrics struct {
+	batchesDropped   *prometheus.CounterVec
+	logsDropped      *prometheus.CounterVec
+	batchesForwarded prometheus.Counter
+}
+
+func newMetrics(registerer prometheus.Registerer) *Metrics {
+	batchesDropped := prometheus.NewCounterVec(prometheus.CounterOpts{
+		Namespace: "agent",
+		Subsystem: "boundary_log_proxy",
+		Name:      "batches_dropped_total",
+		Help: "Total number of boundary log batches dropped before reaching coderd. " +
+			"Reason: buffer_full = the agent's internal buffer is full, meaning boundary is producing logs faster than the agent can forward them to coderd; " +
+			"forward_failed = the agent failed to send the batch to coderd, potentially because coderd is unreachable or the connection was interrupted.",
+	}, []string{"reason"})
+	registerer.MustRegister(batchesDropped)
+
+	logsDropped := prometheus.NewCounterVec(prometheus.CounterOpts{
+		Namespace: "agent",
+		Subsystem: "boundary_log_proxy",
+		Name:      "logs_dropped_total",
+		Help: "Total number of individual boundary log entries dropped before reaching coderd. " +
+			"Reason: buffer_full = the agent's internal buffer is full; " +
+			"forward_failed = the agent failed to send the batch to coderd; " +
+			"boundary_channel_full = boundary's internal send channel overflowed, meaning boundary is generating logs faster than it can batch and send them; " +
+			"boundary_batch_full = boundary's outgoing batch buffer overflowed after a failed flush, meaning boundary could not write to the agent's socket.",
+	}, []string{"reason"})
+	registerer.MustRegister(logsDropped)
+
+	batchesForwarded := prometheus.NewCounter(prometheus.CounterOpts{
+		Namespace: "agent",
+		Subsystem: "boundary_log_proxy",
+		Name:      "batches_forwarded_total",
+		Help: "Total number of boundary log batches successfully forwarded to coderd. " +
+			"Compare with batches_dropped_total to compute a drop rate.",
+	})
+	registerer.MustRegister(batchesForwarded)
+
+	return &Metrics{
+		batchesDropped:   batchesDropped,
+		logsDropped:      logsDropped,
+		batchesForwarded: batchesForwarded,
+	}
+}
@@ -11,6 +11,7 @@ import (
 	"path/filepath"
 	"sync"

+	"github.com/prometheus/client_golang/prometheus"
 	"golang.org/x/xerrors"
 	"google.golang.org/protobuf/proto"

@@ -26,6 +27,13 @@ const (
 	logBufferSize = 100
 )

+const (
+	droppedReasonBoundaryChannelFull = "boundary_channel_full"
+	droppedReasonBoundaryBatchFull   = "boundary_batch_full"
+	droppedReasonBufferFull          = "buffer_full"
+	droppedReasonForwardFailed       = "forward_failed"
+)
+
 // DefaultSocketPath returns the default path for the boundary audit log socket.
 func DefaultSocketPath() string {
 	return filepath.Join(os.TempDir(), "boundary-audit.sock")
@@ -43,6 +51,7 @@ type Reporter interface {
 type Server struct {
 	logger     slog.Logger
 	socketPath string
+	metrics    *Metrics

 	listener net.Listener
 	cancel   context.CancelFunc
@@ -53,10 +62,11 @@ type Server struct {
 }

 // NewServer creates a new boundary log proxy server.
-func NewServer(logger slog.Logger, socketPath string) *Server {
+func NewServer(logger slog.Logger, socketPath string, registerer prometheus.Registerer) *Server {
 	return &Server{
 		logger:     logger.Named("boundary-log-proxy"),
 		socketPath: socketPath,
+		metrics:    newMetrics(registerer),
 		logs:       make(chan *agentproto.ReportBoundaryLogsRequest, logBufferSize),
 	}
 }
@@ -100,9 +110,13 @@ func (s *Server) RunForwarder(ctx context.Context, sender Reporter) error {
 				s.logger.Warn(ctx, "failed to forward boundary logs",
 					slog.Error(err),
 					slog.F("log_count", len(req.Logs)))
+				s.metrics.batchesDropped.WithLabelValues(droppedReasonForwardFailed).Inc()
+				s.metrics.logsDropped.WithLabelValues(droppedReasonForwardFailed).Add(float64(len(req.Logs)))
 				// Continue forwarding other logs. The current batch is lost,
 				// but the socket stays alive.
+				continue
 			}
+			s.metrics.batchesForwarded.Inc()
 		}
 	}
 }
@@ -139,8 +153,8 @@ func (s *Server) handleConnection(ctx context.Context, conn net.Conn) {
 		_ = conn.Close()
 	}()

-	// This is intended to be a sane starting point for the read buffer size. It may be
-	// grown by codec.ReadFrame if necessary.
+	// This is intended to be a sane starting point for the read buffer size.
+	// It may be grown by codec.ReadMessage if necessary.
 	const initBufSize = 1 << 10
 	buf := make([]byte, initBufSize)

@@ -151,36 +165,59 @@ func (s *Server) handleConnection(ctx context.Context, conn net.Conn) {
 		default:
 		}

-		var (
-			tag codec.Tag
-			err error
-		)
-		tag, buf, err = codec.ReadFrame(conn, buf)
+		var err error
+		var msg proto.Message
+		msg, buf, err = codec.ReadMessage(conn, buf)
 		switch {
 		case errors.Is(err, io.EOF) || errors.Is(err, net.ErrClosed):
 			return
-		case err != nil:
+		case errors.Is(err, codec.ErrUnsupportedTag) || errors.Is(err, codec.ErrMessageTooLarge):
 			s.logger.Warn(ctx, "read frame error", slog.Error(err))
 			return
-		}
-
-		if tag != codec.TagV1 {
-			s.logger.Warn(ctx, "invalid tag value", slog.F("tag", tag))
-			return
-		}
-
-		var req agentproto.ReportBoundaryLogsRequest
-		if err := proto.Unmarshal(buf, &req); err != nil {
-			s.logger.Warn(ctx, "proto unmarshal error", slog.Error(err))
+		case err != nil:
+			s.logger.Warn(ctx, "read message error", slog.Error(err))
 			continue
 		}

-		select {
-		case s.logs <- &req:
+		s.handleMessage(ctx, msg)
+	}
+}
+
+func (s *Server) handleMessage(ctx context.Context, msg proto.Message) {
+	switch m := msg.(type) {
+	case *agentproto.ReportBoundaryLogsRequest:
+		s.bufferLogs(ctx, m)
+	case *codec.BoundaryMessage:
+		switch inner := m.Msg.(type) {
+		case *codec.BoundaryMessage_Logs:
+			s.bufferLogs(ctx, inner.Logs)
+		case *codec.BoundaryMessage_Status:
+			s.recordBoundaryStatus(inner.Status)
 		default:
-			s.logger.Warn(ctx, "dropping boundary logs, buffer full",
-				slog.F("log_count", len(req.Logs)))
+			s.logger.Warn(ctx, "unknown BoundaryMessage variant")
 		}
+	default:
+		s.logger.Warn(ctx, "unexpected message type")
+	}
+}
+
+func (s *Server) recordBoundaryStatus(status *codec.BoundaryStatus) {
+	if n := status.DroppedChannelFull; n > 0 {
+		s.metrics.logsDropped.WithLabelValues(droppedReasonBoundaryChannelFull).Add(float64(n))
+	}
+	if n := status.DroppedBatchFull; n > 0 {
+		s.metrics.logsDropped.WithLabelValues(droppedReasonBoundaryBatchFull).Add(float64(n))
+	}
+}
+
+func (s *Server) bufferLogs(ctx context.Context, req *agentproto.ReportBoundaryLogsRequest) {
+	select {
+	case s.logs <- req:
+	default:
+		s.logger.Warn(ctx, "dropping boundary logs, buffer full",
+			slog.F("log_count", len(req.Logs)))
+		s.metrics.batchesDropped.WithLabelValues(droppedReasonBufferFull).Inc()
+		s.metrics.logsDropped.WithLabelValues(droppedReasonBufferFull).Add(float64(len(req.Logs)))
 	}
 }

@@ -11,8 +11,8 @@ import (
 	"testing"
 	"time"

+	"github.com/prometheus/client_golang/prometheus"
 	"github.com/stretchr/testify/require"
-	"google.golang.org/protobuf/proto"
 	"google.golang.org/protobuf/types/known/timestamppb"

 	"github.com/coder/coder/v2/agent/boundarylogproxy"
@@ -21,20 +21,42 @@ import (
 	"github.com/coder/coder/v2/testutil"
 )

-// sendMessage writes a framed protobuf message to the connection.
-func sendMessage(t *testing.T, conn net.Conn, req *agentproto.ReportBoundaryLogsRequest) {
+// sendLogsV1 writes a bare ReportBoundaryLogsRequest using TagV1, the
+// legacy framing that existing boundary deployments use.
+func sendLogsV1(t *testing.T, conn net.Conn, req *agentproto.ReportBoundaryLogsRequest) {
 	t.Helper()

-	data, err := proto.Marshal(req)
+	err := codec.WriteMessage(conn, codec.TagV1, req)
 	if err != nil {
-		//nolint:gocritic // In tests we're not worried about conn being nil.
-		t.Errorf("%s marshal req: %s", conn.LocalAddr().String(), err)
+		t.Errorf("write v1 logs: %s", err)
 	}
+}

-	err = codec.WriteFrame(conn, codec.TagV1, data)
+// sendLogs writes a BoundaryMessage envelope containing logs to the
+// connection using TagV2.
+func sendLogs(t *testing.T, conn net.Conn, req *agentproto.ReportBoundaryLogsRequest) {
+	t.Helper()
+
+	msg := &codec.BoundaryMessage{
+		Msg: &codec.BoundaryMessage_Logs{Logs: req},
+	}
+	err := codec.WriteMessage(conn, codec.TagV2, msg)
 	if err != nil {
-		//nolint:gocritic // In tests we're not worried about conn being nil.
-		t.Errorf("%s write frame: %s", conn.LocalAddr().String(), err)
+		t.Errorf("write logs: %s", err)
+	}
+}
+
+// sendStatus writes a BoundaryMessage envelope containing a BoundaryStatus
+// to the connection using TagV2.
+func sendStatus(t *testing.T, conn net.Conn, status *codec.BoundaryStatus) {
+	t.Helper()
+
+	msg := &codec.BoundaryMessage{
+		Msg: &codec.BoundaryMessage_Status{Status: status},
+	}
+	err := codec.WriteMessage(conn, codec.TagV2, msg)
+	if err != nil {
+		t.Errorf("write status: %s", err)
 	}
 }

@@ -80,7 +102,7 @@ func TestServer_StartAndClose(t *testing.T) {
 	t.Parallel()

 	socketPath := filepath.Join(testutil.TempDirUnixSocket(t), "boundary.sock")
-	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath)
+	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath, prometheus.NewRegistry())

 	err := srv.Start()
 	require.NoError(t, err)
@@ -99,7 +121,7 @@ func TestServer_ReceiveAndForwardLogs(t *testing.T) {
 	t.Parallel()

 	socketPath := filepath.Join(testutil.TempDirUnixSocket(t), "boundary.sock")
-	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath)
+	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath, prometheus.NewRegistry())

 	ctx, cancel := context.WithCancel(context.Background())
 	defer cancel()
@@ -136,7 +158,7 @@ func TestServer_ReceiveAndForwardLogs(t *testing.T) {
 		},
 	}

-	sendMessage(t, conn, req)
+	sendLogs(t, conn, req)

 	// Wait for the reporter to receive the log.
 	require.Eventually(t, func() bool {
@@ -159,7 +181,7 @@ func TestServer_MultipleMessages(t *testing.T) {
 	t.Parallel()

 	socketPath := filepath.Join(testutil.TempDirUnixSocket(t), "boundary.sock")
-	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath)
+	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath, prometheus.NewRegistry())

 	ctx, cancel := context.WithCancel(context.Background())
 	defer cancel()
@@ -195,7 +217,7 @@ func TestServer_MultipleMessages(t *testing.T) {
 				},
 			},
 		}
-		sendMessage(t, conn, req)
+		sendLogs(t, conn, req)
 	}

 	require.Eventually(t, func() bool {
@@ -211,7 +233,7 @@ func TestServer_MultipleConnections(t *testing.T) {
 	t.Parallel()

 	socketPath := filepath.Join(testutil.TempDirUnixSocket(t), "boundary.sock")
-	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath)
+	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath, prometheus.NewRegistry())

 	ctx, cancel := context.WithCancel(context.Background())
 	defer cancel()
@@ -254,7 +276,7 @@ func TestServer_MultipleConnections(t *testing.T) {
 					},
 				},
 			}
-			sendMessage(t, conn, req)
+			sendLogs(t, conn, req)
 		}(i)
 	}
 	wg.Wait()
@@ -272,7 +294,7 @@ func TestServer_MessageTooLarge(t *testing.T) {
 	t.Parallel()

 	socketPath := filepath.Join(testutil.TempDirUnixSocket(t), "boundary.sock")
-	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath)
+	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath, prometheus.NewRegistry())

 	err := srv.Start()
 	require.NoError(t, err)
@@ -300,7 +322,7 @@ func TestServer_ForwarderContinuesAfterError(t *testing.T) {
 	t.Parallel()

 	socketPath := filepath.Join(testutil.TempDirUnixSocket(t), "boundary.sock")
-	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath)
+	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath, prometheus.NewRegistry())

 	err := srv.Start()
 	require.NoError(t, err)
@@ -342,7 +364,7 @@ func TestServer_ForwarderContinuesAfterError(t *testing.T) {
 			},
 		},
 	}
-	sendMessage(t, conn, req1)
+	sendLogs(t, conn, req1)

 	select {
 	case <-reportNotify:
@@ -365,7 +387,7 @@ func TestServer_ForwarderContinuesAfterError(t *testing.T) {
 			},
 		},
 	}
-	sendMessage(t, conn, req2)
+	sendLogs(t, conn, req2)

 	// Only the second message should be recorded.
 	require.Eventually(t, func() bool {
@@ -385,7 +407,7 @@ func TestServer_CloseStopsForwarder(t *testing.T) {
 	t.Parallel()

 	socketPath := filepath.Join(testutil.TempDirUnixSocket(t), "boundary.sock")
-	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath)
+	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath, prometheus.NewRegistry())

 	err := srv.Start()
 	require.NoError(t, err)
@@ -414,7 +436,7 @@ func TestServer_InvalidProtobuf(t *testing.T) {
 	t.Parallel()

 	socketPath := filepath.Join(testutil.TempDirUnixSocket(t), "boundary.sock")
-	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath)
+	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath, prometheus.NewRegistry())

 	err := srv.Start()
 	require.NoError(t, err)
@@ -458,7 +480,7 @@ func TestServer_InvalidProtobuf(t *testing.T) {
 			},
 		},
 	}
-	sendMessage(t, conn, req)
+	sendLogs(t, conn, req)

 	require.Eventually(t, func() bool {
 		logs := reporter.getLogs()
@@ -473,7 +495,7 @@ func TestServer_InvalidHeader(t *testing.T) {
 	t.Parallel()

 	socketPath := filepath.Join(testutil.TempDirUnixSocket(t), "boundary.sock")
-	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath)
+	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath, prometheus.NewRegistry())

 	err := srv.Start()
 	require.NoError(t, err)
@@ -523,7 +545,7 @@ func TestServer_AllowRequest(t *testing.T) {
 	t.Parallel()

 	socketPath := filepath.Join(testutil.TempDirUnixSocket(t), "boundary.sock")
-	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath)
+	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath, prometheus.NewRegistry())

 	err := srv.Start()
 	require.NoError(t, err)
@@ -559,7 +581,7 @@ func TestServer_AllowRequest(t *testing.T) {
 			},
 		},
 	}
-	sendMessage(t, conn, req)
+	sendLogs(t, conn, req)

 	require.Eventually(t, func() bool {
 		logs := reporter.getLogs()
@@ -576,3 +598,258 @@ func TestServer_AllowRequest(t *testing.T) {
 	cancel()
 	<-forwarderDone
 }
+
+func TestServer_TagV1BackwardsCompatibility(t *testing.T) {
+	t.Parallel()
+
+	socketPath := filepath.Join(testutil.TempDirUnixSocket(t), "boundary.sock")
+	srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath, prometheus.NewRegistry())
+
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
+	err := srv.Start()
+	require.NoError(t, err)
+	t.Cleanup(func() { require.NoError(t, srv.Close()) })
+
+	reporter := &fakeReporter{}
+
+	forwarderDone := make(chan error, 1)
+	go func() {
+		forwarderDone <- srv.RunForwarder(ctx, reporter)
+	}()
+
+	conn, err := net.Dial("unix", socketPath)
+	require.NoError(t, err)
+	defer conn.Close()
+
+	// Send a TagV1 message (bare ReportBoundaryLogsRequest) to verify
+	// the server still handles the legacy framing used by existing
+	// boundary deployments.
+	v1Req := &agentproto.ReportBoundaryLogsRequest{
+		Logs: []*agentproto.BoundaryLog{
+			{
+				Allowed: true,
+				Time:    timestamppb.Now(),
+				Resource: &agentproto.BoundaryLog_HttpRequest_{
+					HttpRequest: &agentproto.BoundaryLog_HttpRequest{
+						Method: "GET",
+						Url:    "https://example.com/v1",
+					},
+				},
+			},
+		},
+	}
+	sendLogsV1(t, conn, v1Req)
+
+	require.Eventually(t, func() bool {
+		return len(reporter.getLogs()) == 1
+	}, testutil.WaitShort, testutil.IntervalFast)
+
+	// Now send a TagV2 message on the same connection to verify both
+	// tag versions work interleaved.
+	v2Req := &agentproto.ReportBoundaryLogsRequest{
+		Logs: []*agentproto.BoundaryLog{
+			{
+				Allowed: false,
+				Time:    timestamppb.Now(),
+				Resource: &agentproto.BoundaryLog_HttpRequest_{
+					HttpRequest: &agentproto.BoundaryLog_HttpRequest{
+						Method: "POST",
+						Url:    "https://example.com/v2",
+					},
+				},
+			},
+		},
+	}
+	sendLogs(t, conn, v2Req)
+
+	require.Eventually(t, func() bool {
+		return len(reporter.getLogs()) == 2
+	}, testutil.WaitShort, testutil.IntervalFast)
+
+	logs := reporter.getLogs()
+	require.Equal(t, "https://example.com/v1", logs[0].Logs[0].GetHttpRequest().Url)
+	require.Equal(t, "https://example.com/v2", logs[1].Logs[0].GetHttpRequest().Url)
+
+	cancel()
+	<-forwarderDone
+}
+
+func TestServer_Metrics(t *testing.T) {
+	t.Parallel()
+
+	makeReq := func(n int) *agentproto.ReportBoundaryLogsRequest {
+		logs := make([]*agentproto.BoundaryLog, n)
+		for i := range n {
+			logs[i] = &agentproto.BoundaryLog{
+				Allowed: true,
+				Time:    timestamppb.Now(),
+				Resource: &agentproto.BoundaryLog_HttpRequest_{
+					HttpRequest: &agentproto.BoundaryLog_HttpRequest{
+						Method: "GET",
+						Url:    "https://example.com",
+					},
+				},
+			}
+		}
+		return &agentproto.ReportBoundaryLogsRequest{Logs: logs}
+	}
+
+	// BufferFull needs its own setup because it intentionally does not run
+	// a forwarder so the channel fills up.
+	t.Run("BufferFull", func(t *testing.T) {
+		t.Parallel()
+
+		reg := prometheus.NewRegistry()
+		socketPath := filepath.Join(testutil.TempDirUnixSocket(t), "boundary.sock")
+		srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath, reg)
+
+		err := srv.Start()
+		require.NoError(t, err)
+		t.Cleanup(func() { require.NoError(t, srv.Close()) })
+
+		conn, err := net.Dial("unix", socketPath)
+		require.NoError(t, err)
+		defer conn.Close()
+
+		// Fill the buffer (size 100) without running a forwarder so nothing
+		// drains. Then send one more to trigger the drop path.
+		for range 101 {
+			sendLogs(t, conn, makeReq(1))
+		}
+
+		require.Eventually(t, func() bool {
+			return getCounterVecValue(t, reg, "agent_boundary_log_proxy_batches_dropped_total", "buffer_full") >= 1
+		}, testutil.WaitShort, testutil.IntervalFast)
+		require.GreaterOrEqual(t,
+			getCounterVecValue(t, reg, "agent_boundary_log_proxy_logs_dropped_total", "buffer_full"),
+			float64(1))
+	})
+
+	// The remaining metrics share one server, forwarder, and connection. The
+	// phases run sequentially so metrics accumulate.
+	t.Run("Forwarding", func(t *testing.T) {
+		t.Parallel()
+
+		reg := prometheus.NewRegistry()
+		socketPath := filepath.Join(testutil.TempDirUnixSocket(t), "boundary.sock")
+		srv := boundarylogproxy.NewServer(testutil.Logger(t), socketPath, reg)
+
+		err := srv.Start()
+		require.NoError(t, err)
+		t.Cleanup(func() { require.NoError(t, srv.Close()) })
+
+		reportNotify := make(chan struct{}, 4)
+		reporter := &fakeReporter{
+			err:     context.DeadlineExceeded,
+			errOnce: true,
+			reportCb: func() {
+				select {
+				case reportNotify <- struct{}{}:
+				default:
+				}
+			},
+		}
+
+		ctx, cancel := context.WithCancel(context.Background())
+		defer cancel()
+		forwarderDone := make(chan error, 1)
+		go func() {
+			forwarderDone <- srv.RunForwarder(ctx, reporter)
+		}()
+
+		conn, err := net.Dial("unix", socketPath)
+		require.NoError(t, err)
+		defer conn.Close()
+
+		// Phase 1: the first forward errors
+		sendLogs(t, conn, makeReq(2))
+
+		select {
+		case <-reportNotify:
+		case <-time.After(testutil.WaitShort):
+			t.Fatal("timed out waiting for forward attempt")
+		}
+
+		// The metric is incremented after ReportBoundaryLogs returns, so we
+		// need to poll briefly.
+		require.Eventually(t, func() bool {
+			return getCounterVecValue(t, reg, "agent_boundary_log_proxy_batches_dropped_total", "forward_failed") >= 1
+		}, testutil.WaitShort, testutil.IntervalFast)
+		require.Equal(t, float64(2),
+			getCounterVecValue(t, reg, "agent_boundary_log_proxy_logs_dropped_total", "forward_failed"))
+
+		// Phase 2: forward succeeds.
+		sendLogs(t, conn, makeReq(1))
+
+		require.Eventually(t, func() bool {
+			return len(reporter.getLogs()) >= 1
+		}, testutil.WaitShort, testutil.IntervalFast)
+		require.Equal(t, float64(1),
+			getCounterValue(t, reg, "agent_boundary_log_proxy_batches_forwarded_total"))
+
+		// Phase 3: boundary-reported drop counts arrive as a separate BoundaryStatus
+		// message, not piggybacked on log batches.
+		sendStatus(t, conn, &codec.BoundaryStatus{
+			DroppedChannelFull: 5,
+			DroppedBatchFull:   3,
+		})
+
+		// Status is handled immediately by the reader goroutine, not by the
+		// forwarder, so poll metrics directly.
+		require.Eventually(t, func() bool {
+			return getCounterVecValue(t, reg, "agent_boundary_log_proxy_logs_dropped_total", "boundary_channel_full") >= 5
+		}, testutil.WaitShort, testutil.IntervalFast)
+		require.Equal(t, float64(5),
+			getCounterVecValue(t, reg, "agent_boundary_log_proxy_logs_dropped_total", "boundary_channel_full"))
+		require.Equal(t, float64(3),
+			getCounterVecValue(t, reg, "agent_boundary_log_proxy_logs_dropped_total", "boundary_batch_full"))
+
+		cancel()
+		<-forwarderDone
+	})
+}
+
+// getCounterVecValue returns the current value of a CounterVec metric filtered
+// by the given reason label.
+func getCounterVecValue(t *testing.T, reg *prometheus.Registry, name, reason string) float64 {
+	t.Helper()
+
+	metrics, err := reg.Gather()
+	require.NoError(t, err)
+
+	for _, mf := range metrics {
+		if mf.GetName() != name {
+			continue
+		}
+		for _, m := range mf.GetMetric() {
+			for _, lp := range m.GetLabel() {
+				if lp.GetName() == "reason" && lp.GetValue() == reason {
+					return m.GetCounter().GetValue()
+				}
+			}
+		}
+	}
+
+	return 0
+}
+
+// getCounterValue returns the current value of a Counter metric.
+func getCounterValue(t *testing.T, reg *prometheus.Registry, name string) float64 {
+	t.Helper()
+
+	metrics, err := reg.Gather()
+	require.NoError(t, err)
+
+	for _, mf := range metrics {
+		if mf.GetName() != name {
+			continue
+		}
+		for _, m := range mf.GetMetric() {
+			return m.GetCounter().GetValue()
+		}
+	}
+
+	return 0
+}
@@ -4,7 +4,7 @@ import (
 	"context"
 	"os"
 	"path/filepath"
-	"sort"
+	"slices"
 	"testing"

 	"github.com/stretchr/testify/require"
@@ -228,6 +228,6 @@ func resultPaths(results []filefinder.Result) []string {
 	for i, r := range results {
 		paths[i] = r.Path
 	}
-	sort.Strings(paths)
+	slices.Sort(paths)
 	return paths
 }
--- a/Show More
+++ b/Show More