chore: backport aibridge fixes (#22266 )

Backports https://github.com/coder/coder/pull/22264 Includes fixes https://github.com/coder/aibridge/pull/189 and https://github.com/coder/aibridge/pull/185 Signed-off-by: Danny Kopping <danny@coder.com>
feat: convert soft_limit to limit (cherry-pick/v2.30) (#22209 )
2026-02-23 17:18:32 -05:00 · 2026-02-23 17:18:14 -05:00 · 2026-02-23 17:17:40 -05:00 · 2026-02-23 17:17:16 -05:00 · 2026-02-20 13:19:18 +01:00 · 2026-02-20 12:49:48 +01:00
593 changed files with 27102 additions and 8307 deletions
@@ -0,0 +1,79 @@
+---
+name: doc-check
+description: Checks if code changes require documentation updates
+---
+
+# Documentation Check Skill
+
+Review code changes and determine if documentation updates or new documentation
+is needed.
+
+## Workflow
+
+1. **Get the code changes** - Use the method provided in the prompt, or if none
+   specified:
+   - For a PR: `gh pr diff <PR_NUMBER> --repo coder/coder`
+   - For local changes: `git diff main` or `git diff --staged`
+   - For a branch: `git diff main...<branch>`
+
+2. **Understand the scope** - Consider what changed:
+   - Is this user-facing or internal?
+   - Does it change behavior, APIs, CLI flags, or configuration?
+   - Even for "internal" or "chore" changes, always verify the actual diff
+
+3. **Search the docs** for related content in `docs/`
+
+4. **Decide what's needed**:
+   - Do existing docs need updates to match the code?
+   - Is new documentation needed for undocumented features?
+   - Or is everything already covered?
+
+5. **Report findings** - Use the method provided in the prompt, or if none
+   specified, summarize findings directly
+
+## What to Check
+
+- **Accuracy**: Does documentation match current code behavior?
+- **Completeness**: Are new features/options documented?
+- **Examples**: Do code examples still work?
+- **CLI/API changes**: Are new flags, endpoints, or options documented?
+- **Configuration**: Are new environment variables or settings documented?
+- **Breaking changes**: Are migration steps documented if needed?
+- **Premium features**: Should docs indicate `(Premium)` in the title?
+
+## Key Documentation Info
+
+- **`docs/manifest.json`** - Navigation structure; new pages MUST be added here
+- **`docs/reference/cli/*.md`** - Auto-generated from Go code, don't edit directly
+- **Premium features** - H1 title should include `(Premium)` suffix
+
+## Coder-Specific Patterns
+
+### Callouts
+
+Use GitHub-Flavored Markdown alerts:
+
+```markdown
+> [!NOTE]
+> Additional helpful information.
+
+> [!WARNING]
+> Important warning about potential issues.
+
+> [!TIP]
+> Helpful tip for users.
+```
+
+### CLI Documentation
+
+CLI docs in `docs/reference/cli/` are auto-generated. Don't suggest editing them
+directly. Instead, changes should be made in the Go code that defines the CLI
+commands (typically in `cli/` directory).
+
+### Code Examples
+
+Use `sh` for shell commands:
+
+```sh
+coder server --flag-name value
+```
@@ -1,4 +1,4 @@
 #!/bin/sh

 # Start Docker service if not already running.
-sudo service docker start
+sudo service docker status >/dev/null 2>&1 || sudo service docker start
@@ -4,7 +4,7 @@ description: |
 inputs:
  version:
    description: "The Go version to use."
-    default: "1.24.10"
+    default: "1.25.6"
  use-preinstalled-go:
    description: "Whether to use preinstalled Go."
    default: "false"
@@ -7,5 +7,5 @@ runs:
    - name: Install Terraform
      uses: hashicorp/setup-terraform@b9cd54a3c349d3f38e8881555d616ced269862dd # v3.1.2
      with:
-        terraform_version: 1.14.1
+        terraform_version: 1.14.5
        terraform_wrapper: false
@@ -35,12 +35,12 @@ jobs:
      tailnet-integration: ${{ steps.filter.outputs.tailnet-integration }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -124,7 +124,7 @@ jobs:
  #   runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
  #   steps:
  #     - name: Checkout
-  #       uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+  #       uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
  #       with:
  #         fetch-depth: 1
  #         # See: https://github.com/stefanzweifel/git-auto-commit-action?tab=readme-ov-file#commits-made-by-this-action-do-not-trigger-new-workflow-runs
@@ -157,12 +157,12 @@ jobs:
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -181,7 +181,7 @@ jobs:
          echo "LINT_CACHE_DIR=$dir" >> "$GITHUB_ENV"

      - name: golangci-lint cache
-        uses: actions/cache@9255dc7a253b0ccc959486e2bca901246202afeb # v5.0.1
+        uses: actions/cache@8b402f58fbc84540c8b491a91e594a4576fec3d7 # v5.0.2
        with:
          path: |
            ${{ env.LINT_CACHE_DIR }}
@@ -251,12 +251,12 @@ jobs:
    if: ${{ !cancelled() }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -308,12 +308,12 @@ jobs:
    timeout-minutes: 20
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -360,7 +360,7 @@ jobs:
          - windows-2022
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

@@ -386,7 +386,7 @@ jobs:
        uses: coder/setup-ramdisk-action@e1100847ab2d7bcd9d14bcda8f2d1b0f07b36f1b # v0.1.0

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -554,12 +554,12 @@ jobs:
    timeout-minutes: 25
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -616,12 +616,12 @@ jobs:
    timeout-minutes: 25
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -688,12 +688,12 @@ jobs:
    timeout-minutes: 20
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -715,12 +715,12 @@ jobs:
    timeout-minutes: 20
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -748,12 +748,12 @@ jobs:
    name: ${{ matrix.variant.name }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -828,12 +828,12 @@ jobs:
    if: needs.changes.outputs.site == 'true' || needs.changes.outputs.ci == 'true'
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          # 👇 Ensures Chromatic can read your full git history
          fetch-depth: 0
@@ -849,7 +849,7 @@ jobs:
      # the check to pass. This is desired in PRs, but not in mainline.
      - name: Publish to Chromatic (non-mainline)
        if: github.ref != 'refs/heads/main' && github.repository_owner == 'coder'
-        uses: chromaui/action@4c20b95e9d3209ecfdf9cd6aace6bbde71ba1694 # v13.3.4
+        uses: chromaui/action@07791f8243f4cb2698bf4d00426baf4b2d1cb7e0 # v13.3.5
        env:
          NODE_OPTIONS: "--max_old_space_size=4096"
          STORYBOOK: true
@@ -881,7 +881,7 @@ jobs:
      # infinitely "in progress" in mainline unless we re-review each build.
      - name: Publish to Chromatic (mainline)
        if: github.ref == 'refs/heads/main' && github.repository_owner == 'coder'
-        uses: chromaui/action@4c20b95e9d3209ecfdf9cd6aace6bbde71ba1694 # v13.3.4
+        uses: chromaui/action@07791f8243f4cb2698bf4d00426baf4b2d1cb7e0 # v13.3.5
        env:
          NODE_OPTIONS: "--max_old_space_size=4096"
          STORYBOOK: true
@@ -909,12 +909,12 @@ jobs:

    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          # 0 is required here for version.sh to work.
          fetch-depth: 0
@@ -980,7 +980,7 @@ jobs:
    if: always()
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

@@ -1018,7 +1018,7 @@ jobs:
    steps:
      # Harden Runner doesn't work on macOS
      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -1100,12 +1100,12 @@ jobs:
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -1155,12 +1155,12 @@ jobs:
      IMAGE: ghcr.io/coder/coder-preview:${{ steps.build-docker.outputs.tag }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -1552,12 +1552,12 @@ 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@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -215,7 +215,7 @@ jobs:
          } >> "${GITHUB_OUTPUT}"

      - name: Checkout create-task-action
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 1
          path: ./.github/actions/create-task-action
@@ -249,7 +249,7 @@ jobs:
          } >> "${GITHUB_OUTPUT}"

      - name: Checkout create-task-action
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 1
          path: ./.github/actions/create-task-action
@@ -36,12 +36,12 @@ jobs:
      verdict: ${{ steps.check.outputs.verdict }} # DEPLOY or NOOP
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -65,12 +65,12 @@ jobs:
      packages: write # to retag image as dogfood
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -146,12 +146,12 @@ jobs:
    needs: deploy
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -2,14 +2,26 @@
 # It creates a Coder Task that uses AI to analyze the PR changes,
 # search existing docs, and comment with recommendations.
 #
-# Triggered by: Adding the "doc-check" label to a PR, or manual dispatch.
+# Triggers:
+#   - New PR opened: Initial documentation review
+#   - PR updated (synchronize): Re-review after changes
+#   - Label "doc-check" added: Manual trigger for review
+#   - PR marked ready for review: Review when draft is promoted
+#   - Workflow dispatch: Manual run with PR URL
+#
+# Note: This workflow requires access to secrets and will be skipped for:
+#   - Any PR where secrets are not available
+# For these PRs, maintainers can manually trigger via workflow_dispatch.

 name: AI Documentation Check

 on:
  pull_request:
    types:
+      - opened
+      - synchronize
      - labeled
+      - ready_for_review
  workflow_dispatch:
    inputs:
      pr_url:
@@ -26,8 +38,16 @@ jobs:
  doc-check:
    name: Analyze PR for Documentation Updates Needed
    runs-on: ubuntu-latest
+    # Run on: opened, synchronize, labeled (with doc-check label), ready_for_review, or workflow_dispatch
+    # Skip draft PRs unless manually triggered
    if: |
-      (github.event.label.name == 'doc-check' || github.event_name == 'workflow_dispatch') &&
+      (
+        github.event.action == 'opened' ||
+        github.event.action == 'synchronize' ||
+        github.event.label.name == 'doc-check' ||
+        github.event.action == 'ready_for_review' ||
+        github.event_name == 'workflow_dispatch'
+      ) &&
      (github.event.pull_request.draft == false || github.event_name == 'workflow_dispatch')
    timeout-minutes: 30
    env:
@@ -39,120 +59,155 @@ jobs:
      actions: write

    steps:
+      - name: Check if secrets are available
+        id: check-secrets
+        env:
+          CODER_URL: ${{ secrets.DOC_CHECK_CODER_URL }}
+          CODER_TOKEN: ${{ secrets.DOC_CHECK_CODER_SESSION_TOKEN }}
+        run: |
+          if [[ -z "${CODER_URL}" || -z "${CODER_TOKEN}" ]]; then
+            echo "skip=true" >> "${GITHUB_OUTPUT}"
+            echo "Secrets not available - skipping doc-check."
+            echo "This is expected for PRs where secrets are not available."
+            echo "Maintainers can manually trigger via workflow_dispatch if needed."
+            {
+              echo "⚠️ Workflow skipped: Secrets not available"
+              echo ""
+              echo "This workflow requires secrets that are unavailable for this run."
+              echo "Maintainers can manually trigger via workflow_dispatch if needed."
+            } >> "${GITHUB_STEP_SUMMARY}"
+          else
+            echo "skip=false" >> "${GITHUB_OUTPUT}"
+          fi
+
+      - name: Setup Coder CLI
+        if: steps.check-secrets.outputs.skip != 'true'
+        uses: coder/setup-action@4a607a8113d4e676e2d7c34caa20a814bc88bfda # v1
+        with:
+          access_url: ${{ secrets.DOC_CHECK_CODER_URL }}
+          coder_session_token: ${{ secrets.DOC_CHECK_CODER_SESSION_TOKEN }}
+
      - name: Determine PR Context
+        if: steps.check-secrets.outputs.skip != 'true'
        id: determine-context
        env:
-          GITHUB_ACTOR: ${{ github.actor }}
          GITHUB_EVENT_NAME: ${{ github.event_name }}
+          GITHUB_EVENT_ACTION: ${{ github.event.action }}
          GITHUB_EVENT_PR_HTML_URL: ${{ github.event.pull_request.html_url }}
          GITHUB_EVENT_PR_NUMBER: ${{ github.event.pull_request.number }}
-          GITHUB_EVENT_SENDER_ID: ${{ github.event.sender.id }}
-          GITHUB_EVENT_SENDER_LOGIN: ${{ github.event.sender.login }}
          INPUTS_PR_URL: ${{ inputs.pr_url }}
          INPUTS_TEMPLATE_PRESET: ${{ inputs.template_preset || '' }}
-          GH_TOKEN: ${{ github.token }}
        run: |
          echo "Using template preset: ${INPUTS_TEMPLATE_PRESET}"
          echo "template_preset=${INPUTS_TEMPLATE_PRESET}" >> "${GITHUB_OUTPUT}"

-          # For workflow_dispatch, use the provided PR URL
+          # Determine trigger type for task context
          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 ${GITHUB_ACTOR}"
+            echo "trigger_type=manual" >> "${GITHUB_OUTPUT}"
+            echo "Using PR URL: ${INPUTS_PR_URL}"
+
+            # Validate PR URL format
+            if [[ ! "${INPUTS_PR_URL}" =~ ^https://github\.com/[^/]+/[^/]+/pull/[0-9]+$ ]]; then
+              echo "::error::Invalid PR URL format: ${INPUTS_PR_URL}"
+              echo "::error::Expected format: https://github.com/owner/repo/pull/NUMBER"
              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 PR URL: ${INPUTS_PR_URL}"
-            # Convert /pull/ to /issues/ for create-task-action compatibility
            ISSUE_URL="${INPUTS_PR_URL/\/pull\//\/issues\/}"
            echo "pr_url=${ISSUE_URL}" >> "${GITHUB_OUTPUT}"
-
-            # Extract PR number from URL for later use
            PR_NUMBER=$(echo "${INPUTS_PR_URL}" | grep -oP '(?<=pull/)\d+')
            echo "pr_number=${PR_NUMBER}" >> "${GITHUB_OUTPUT}"

          elif [[ "${GITHUB_EVENT_NAME}" == "pull_request" ]]; then
-            GITHUB_USER_ID=${GITHUB_EVENT_SENDER_ID}
-            echo "Using label adder: ${GITHUB_EVENT_SENDER_LOGIN} (ID: ${GITHUB_USER_ID})"
-            echo "github_user_id=${GITHUB_USER_ID}" >> "${GITHUB_OUTPUT}"
-            echo "github_username=${GITHUB_EVENT_SENDER_LOGIN}" >> "${GITHUB_OUTPUT}"
-
            echo "Using PR URL: ${GITHUB_EVENT_PR_HTML_URL}"
-            # Convert /pull/ to /issues/ for create-task-action compatibility
            ISSUE_URL="${GITHUB_EVENT_PR_HTML_URL/\/pull\//\/issues\/}"
            echo "pr_url=${ISSUE_URL}" >> "${GITHUB_OUTPUT}"
            echo "pr_number=${GITHUB_EVENT_PR_NUMBER}" >> "${GITHUB_OUTPUT}"

+            # Set trigger type based on action
+            case "${GITHUB_EVENT_ACTION}" in
+              opened)
+                echo "trigger_type=new_pr" >> "${GITHUB_OUTPUT}"
+                ;;
+              synchronize)
+                echo "trigger_type=pr_updated" >> "${GITHUB_OUTPUT}"
+                ;;
+              labeled)
+                echo "trigger_type=label_requested" >> "${GITHUB_OUTPUT}"
+                ;;
+              ready_for_review)
+                echo "trigger_type=ready_for_review" >> "${GITHUB_OUTPUT}"
+                ;;
+              *)
+                echo "trigger_type=unknown" >> "${GITHUB_OUTPUT}"
+                ;;
+            esac
+
          else
            echo "::error::Unsupported event type: ${GITHUB_EVENT_NAME}"
            exit 1
          fi

-      - name: Extract changed files and build prompt
+      - name: Build task prompt
+        if: steps.check-secrets.outputs.skip != 'true'
        id: extract-context
        env:
-          PR_URL: ${{ steps.determine-context.outputs.pr_url }}
          PR_NUMBER: ${{ steps.determine-context.outputs.pr_number }}
-          GH_TOKEN: ${{ github.token }}
+          TRIGGER_TYPE: ${{ steps.determine-context.outputs.trigger_type }}
        run: |
-          echo "Analyzing PR #${PR_NUMBER}"
+          echo "Analyzing PR #${PR_NUMBER} (trigger: ${TRIGGER_TYPE})"

-          # Build task prompt - using unquoted heredoc so variables expand
-          TASK_PROMPT=$(cat <<EOF
-          Review PR #${PR_NUMBER} and determine if documentation needs updating or creating.
+          # Build context based on trigger type
+          case "${TRIGGER_TYPE}" in
+            new_pr)
+              CONTEXT="This is a NEW PR. Perform a thorough documentation review."
+              ;;
+            pr_updated)
+              CONTEXT="This PR was UPDATED with new commits. Only comment if the changes affect documentation needs or address previous feedback."
+              ;;
+            label_requested)
+              CONTEXT="A documentation review was REQUESTED via label. Perform a thorough documentation review."
+              ;;
+            ready_for_review)
+              CONTEXT="This PR was marked READY FOR REVIEW (converted from draft). Perform a thorough documentation review."
+              ;;
+            manual)
+              CONTEXT="This is a MANUAL review request. Perform a thorough documentation review."
+              ;;
+            *)
+              CONTEXT="Perform a thorough documentation review."
+              ;;
+          esac

-          PR URL: ${PR_URL}
+          # Build task prompt with PR-specific context
+          TASK_PROMPT="Use the doc-check skill to review PR #${PR_NUMBER} in coder/coder.

-          WORKFLOW:
-            1. Setup (repo is pre-cloned at ~/coder)
-               cd ~/coder
-               git fetch origin pull/${PR_NUMBER}/head:pr-${PR_NUMBER}
-               git checkout pr-${PR_NUMBER}
+          ${CONTEXT}

-            2. Get PR info
-               Use GitHub MCP tools to get PR title, body, and diff
-               Or use: git diff main...pr-${PR_NUMBER}
+          Use \`gh\` to get PR details, diff, and all comments. Check for previous doc-check comments (from coder-doc-check) and only post a new comment if it adds value.

-            3. Understand Changes
-               Read the diff and identify what changed
-               Ask: Is this user-facing? Does it change behavior? Is it a new feature?
+          ## Comment format

-            4. Search for Related Docs
-               cat ~/coder/docs/manifest.json | jq '.routes[] | {title, path}' | head -50
-               grep -ri "relevant_term" ~/coder/docs/ --include="*.md"
+          Use this structure (only include relevant sections):

-            5. Decide
-               NEEDS DOCS if: New feature, API change, CLI change, behavior change, user-visible
-               NO DOCS if: Internal refactor, test-only, already documented, non-user-facing, dependency updates
-               FIRST check: Did this PR already update docs? If yes and complete, say "No Changes Needed"
+          \`\`\`
+          ## Documentation Check

-            6. Comment on the PR using this format
+          ### Previous Feedback
+          [For re-reviews only: Addressed | Partially addressed | Not yet addressed]

-          COMMENT FORMAT:
-          ## 📚 Documentation Check
+          ### Updates Needed
+          - [ ] \`docs/path/file.md\` - [what needs to change]

-          ### ✅ Updates Needed
-          - **[docs/path/file.md](github_link)** - Brief what needs changing
+          ### New Documentation Needed
+          - [ ] \`docs/suggested/path.md\` - [what should be documented]

-          ### 📝 New Docs Needed
-          - **docs/suggested/location.md** - What should be documented
-
-          ### ✨ No Changes Needed
-          [Reason: Documents already updated in PR | Internal changes only | Test-only | No user-facing impact]
+          ### No Changes Needed
+          [brief explanation - use this OR the above sections, not both]

          ---
-          *This comment was generated by an AI Agent through [Coder Tasks](https://coder.com/docs/ai-coder/tasks)*
-
-          DOCS STRUCTURE:
-            Read ~/coder/docs/manifest.json for the complete documentation structure.
-            Common areas include: reference/, admin/, user-guides/, ai-coder/, install/, tutorials/
-            But check manifest.json - it has everything.
-
-          EOF
-          )
+          *Automated review via [Coder Tasks](https://coder.com/docs/ai-coder/tasks)*
+          \`\`\`"

          # Output the prompt
          {
@@ -162,7 +217,8 @@ jobs:
          } >> "${GITHUB_OUTPUT}"

      - name: Checkout create-task-action
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        if: steps.check-secrets.outputs.skip != 'true'
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 1
          path: ./.github/actions/create-task-action
@@ -171,22 +227,24 @@ jobs:
          repository: coder/create-task-action

      - name: Create Coder Task for Documentation Check
+        if: steps.check-secrets.outputs.skip != 'true'
        id: create_task
        uses: ./.github/actions/create-task-action
        with:
          coder-url: ${{ secrets.DOC_CHECK_CODER_URL }}
          coder-token: ${{ secrets.DOC_CHECK_CODER_SESSION_TOKEN }}
          coder-organization: "default"
-          coder-template-name: coder
+          coder-template-name: coder-workflow-bot
          coder-template-preset: ${{ steps.determine-context.outputs.template_preset }}
          coder-task-name-prefix: doc-check
          coder-task-prompt: ${{ steps.extract-context.outputs.task_prompt }}
-          github-user-id: ${{ steps.determine-context.outputs.github_user_id }}
+          coder-username: doc-check-bot
          github-token: ${{ github.token }}
          github-issue-url: ${{ steps.determine-context.outputs.pr_url }}
-          comment-on-issue: true
+          comment-on-issue: false

-      - name: Write outputs
+      - name: Write Task Info
+        if: steps.check-secrets.outputs.skip != 'true'
        env:
          TASK_CREATED: ${{ steps.create_task.outputs.task-created }}
          TASK_NAME: ${{ steps.create_task.outputs.task-name }}
@@ -201,5 +259,140 @@ jobs:
            echo "**Task name:** ${TASK_NAME}"
            echo "**Task URL:** ${TASK_URL}"
            echo ""
-            echo "The Coder task is analyzing the PR changes and will comment with documentation recommendations."
+          } >> "${GITHUB_STEP_SUMMARY}"
+
+      - name: Wait for Task Completion
+        if: steps.check-secrets.outputs.skip != 'true'
+        id: wait_task
+        env:
+          TASK_NAME: ${{ steps.create_task.outputs.task-name }}
+        run: |
+          echo "Waiting for task to complete..."
+          echo "Task name: ${TASK_NAME}"
+
+          if [[ -z "${TASK_NAME}" ]]; then
+            echo "::error::TASK_NAME is empty"
+            exit 1
+          fi
+
+          MAX_WAIT=600  # 10 minutes
+          WAITED=0
+          POLL_INTERVAL=3
+          LAST_STATUS=""
+
+          is_workspace_message() {
+            local msg="$1"
+            [[ -z "$msg" ]] && return 0  # Empty = treat as workspace/startup
+            [[ "$msg" =~ ^Workspace ]] && return 0
+            [[ "$msg" =~ ^Agent ]] && return 0
+            return 1
+          }
+
+          while [[ $WAITED -lt $MAX_WAIT ]]; do
+            # Get task status (|| true prevents set -e from exiting on non-zero)
+            RAW_OUTPUT=$(coder task status "${TASK_NAME}" -o json 2>&1) || true
+            STATUS_JSON=$(echo "$RAW_OUTPUT" | grep -v "^version mismatch\|^download v" || true)
+
+            # Debug: show first poll's raw output
+            if [[ $WAITED -eq 0 ]]; then
+              echo "Raw status output: ${RAW_OUTPUT:0:500}"
+            fi
+
+            if [[ -z "$STATUS_JSON" ]] || ! echo "$STATUS_JSON" | jq -e . >/dev/null 2>&1; then
+              if [[ "$LAST_STATUS" != "waiting" ]]; then
+                echo "[${WAITED}s] Waiting for task status..."
+                LAST_STATUS="waiting"
+              fi
+              sleep $POLL_INTERVAL
+              WAITED=$((WAITED + POLL_INTERVAL))
+              continue
+            fi
+
+            TASK_STATE=$(echo "$STATUS_JSON" | jq -r '.current_state.state // "unknown"')
+            TASK_MESSAGE=$(echo "$STATUS_JSON" | jq -r '.current_state.message // ""')
+            WORKSPACE_STATUS=$(echo "$STATUS_JSON" | jq -r '.workspace_status // "unknown"')
+
+            # Build current status string for comparison
+            CURRENT_STATUS="${TASK_STATE}|${WORKSPACE_STATUS}|${TASK_MESSAGE}"
+
+            # Only log if status changed
+            if [[ "$CURRENT_STATUS" != "$LAST_STATUS" ]]; then
+              if [[ "$TASK_STATE" == "idle" ]] && is_workspace_message "$TASK_MESSAGE"; then
+                echo "[${WAITED}s] Workspace ready, waiting for Agent..."
+              else
+                echo "[${WAITED}s] State: ${TASK_STATE} | Workspace: ${WORKSPACE_STATUS} | ${TASK_MESSAGE}"
+              fi
+              LAST_STATUS="$CURRENT_STATUS"
+            fi
+
+            if [[ "$WORKSPACE_STATUS" == "failed" || "$WORKSPACE_STATUS" == "canceled" ]]; then
+              echo "::error::Workspace failed: ${WORKSPACE_STATUS}"
+              exit 1
+            fi
+
+            if [[ "$TASK_STATE" == "idle" ]]; then
+              if ! is_workspace_message "$TASK_MESSAGE"; then
+                # Real completion message from Claude!
+                echo ""
+                echo "Task completed: ${TASK_MESSAGE}"
+                RESULT_URI=$(echo "$STATUS_JSON" | jq -r '.current_state.uri // ""')
+                echo "result_uri=${RESULT_URI}" >> "${GITHUB_OUTPUT}"
+                echo "task_message=${TASK_MESSAGE}" >> "${GITHUB_OUTPUT}"
+                break
+              fi
+            fi
+
+            sleep $POLL_INTERVAL
+            WAITED=$((WAITED + POLL_INTERVAL))
+          done
+
+          if [[ $WAITED -ge $MAX_WAIT ]]; then
+            echo "::error::Task monitoring timed out after ${MAX_WAIT}s"
+            exit 1
+          fi
+
+      - name: Fetch Task Logs
+        if: always() && steps.check-secrets.outputs.skip != 'true'
+        env:
+          TASK_NAME: ${{ steps.create_task.outputs.task-name }}
+        run: |
+          echo "::group::Task Conversation Log"
+          if [[ -n "${TASK_NAME}" ]]; then
+            coder task logs "${TASK_NAME}" 2>&1 || echo "Failed to fetch logs"
+          else
+            echo "No task name, skipping log fetch"
+          fi
+          echo "::endgroup::"
+
+      - name: Cleanup Task
+        if: always() && steps.check-secrets.outputs.skip != 'true'
+        env:
+          TASK_NAME: ${{ steps.create_task.outputs.task-name }}
+        run: |
+          if [[ -n "${TASK_NAME}" ]]; then
+            echo "Deleting task: ${TASK_NAME}"
+            coder task delete "${TASK_NAME}" -y 2>&1 || echo "Task deletion failed or already deleted"
+          else
+            echo "No task name, skipping cleanup"
+          fi
+
+      - name: Write Final Summary
+        if: always() && steps.check-secrets.outputs.skip != 'true'
+        env:
+          TASK_NAME: ${{ steps.create_task.outputs.task-name }}
+          TASK_MESSAGE: ${{ steps.wait_task.outputs.task_message }}
+          RESULT_URI: ${{ steps.wait_task.outputs.result_uri }}
+          PR_NUMBER: ${{ steps.determine-context.outputs.pr_number }}
+        run: |
+          {
+            echo ""
+            echo "---"
+            echo "### Result"
+            echo ""
+            echo "**Status:** ${TASK_MESSAGE:-Task completed}"
+            if [[ -n "${RESULT_URI}" ]]; then
+              echo "**Comment:** ${RESULT_URI}"
+            fi
+            echo ""
+            echo "Task \`${TASK_NAME}\` has been cleaned up."
          } >> "${GITHUB_STEP_SUMMARY}"
@@ -38,12 +38,12 @@ jobs:
    if: github.repository_owner == 'coder'
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          persist-credentials: false

@@ -23,7 +23,7 @@ jobs:
    runs-on: ubuntu-latest
    steps:
      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          persist-credentials: false

@@ -26,12 +26,12 @@ jobs:
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-4' || 'ubuntu-latest' }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          persist-credentials: false

@@ -42,7 +42,7 @@ jobs:
          # on version 2.29 and above.
          nix_version: "2.28.5"

-      - uses: nix-community/cache-nix-action@b426b118b6dc86d6952988d396aa7c6b09776d08 # v7.0.0
+      - uses: nix-community/cache-nix-action@106bba72ed8e29c8357661199511ef07790175e9 # v7.0.1
        with:
          # restore and save a cache using this key
          primary-key: nix-${{ runner.os }}-${{ hashFiles('**/*.nix', '**/flake.lock') }}
@@ -125,12 +125,12 @@ jobs:
      id-token: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          persist-credentials: false

@@ -28,7 +28,7 @@ jobs:
          - windows-2022
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

@@ -54,7 +54,7 @@ jobs:
        uses: coder/setup-ramdisk-action@e1100847ab2d7bcd9d14bcda8f2d1b0f07b36f1b # v0.1.0

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -15,7 +15,7 @@ jobs:
    runs-on: ubuntu-latest
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

@@ -19,7 +19,7 @@ jobs:
      packages: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

@@ -39,12 +39,12 @@ jobs:
      PR_OPEN: ${{ steps.check_pr.outputs.pr_open }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          persist-credentials: false

@@ -76,12 +76,12 @@ jobs:
    runs-on: "ubuntu-latest"
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -184,7 +184,7 @@ jobs:
      pull-requests: write # needed for commenting on PRs
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

@@ -228,12 +228,12 @@ jobs:
      CODER_IMAGE_TAG: ${{ needs.get_info.outputs.CODER_IMAGE_TAG }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -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@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

@@ -337,7 +337,7 @@ jobs:
          kubectl create namespace "pr${PR_NUMBER}"

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          persist-credentials: false

@@ -14,7 +14,7 @@ jobs:

    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

@@ -65,7 +65,7 @@ jobs:
    steps:
      # Harden Runner doesn't work on macOS.
      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -164,12 +164,12 @@ jobs:
      version: ${{ steps.version.outputs.version }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -802,7 +802,7 @@ jobs:
      # 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@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

@@ -878,7 +878,7 @@ jobs:

    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

@@ -888,7 +888,7 @@ jobs:
          GH_TOKEN: ${{ secrets.CDRCI_GITHUB_TOKEN }}

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -971,12 +971,12 @@ jobs:
    if: ${{ !inputs.dry_run }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -20,12 +20,12 @@ jobs:

    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: "Checkout code"
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          persist-credentials: false

@@ -27,12 +27,12 @@ jobs:
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          persist-credentials: false

@@ -69,12 +69,12 @@ jobs:
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -146,7 +146,7 @@ jobs:
          echo "image=$(cat "$image_job")" >> "$GITHUB_OUTPUT"

      - name: Run Trivy vulnerability scanner
-        uses: aquasecurity/trivy-action@b6643a29fecd7f34b3597bc6acb0a98b03d33ff8
+        uses: aquasecurity/trivy-action@c1824fd6edce30d7ab345a9989de00bbd46ef284 # v0.34.0
        with:
          image-ref: ${{ steps.build.outputs.image }}
          format: sarif
@@ -18,7 +18,7 @@ jobs:
      pull-requests: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

@@ -96,12 +96,12 @@ jobs:
      contents: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout repository
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          persist-credentials: false
      - name: Run delete-old-branches-action
@@ -120,7 +120,7 @@ jobs:
      actions: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

@@ -153,7 +153,7 @@ jobs:
          } >> "${GITHUB_OUTPUT}"

      - name: Checkout repository
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 1
          path: ./.github/actions/create-task-action
@@ -21,12 +21,12 @@ jobs:
      pull-requests: write # required to post PR review comments by the action
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        uses: step-security/harden-runner@5ef0c079ce82195b2a36a210272d6b661572d83e # v2.14.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          persist-credentials: false

@@ -3,6 +3,7 @@
 .eslintcache
 .gitpod.yml
 .idea
+.run
 **/*.swp
 gotests.coverage
 gotests.xml
@@ -69,6 +69,9 @@ MOST_GO_SRC_FILES := $(shell \
 # All the shell files in the repo, excluding ignored files.
 SHELL_SRC_FILES := $(shell find . $(FIND_EXCLUSIONS) -type f -name '*.sh')

+MIGRATION_FILES := $(shell find ./coderd/database/migrations/ -maxdepth 1 $(FIND_EXCLUSIONS) -type f -name '*.sql')
+FIXTURE_FILES := $(shell find ./coderd/database/migrations/testdata/fixtures/ $(FIND_EXCLUSIONS) -type f -name '*.sql')
+
 # Ensure we don't use the user's git configs which might cause side-effects
 GIT_FLAGS = GIT_CONFIG_GLOBAL=/dev/null GIT_CONFIG_SYSTEM=/dev/null

@@ -561,7 +564,7 @@ endif

 # Note: we don't run zizmor in the lint target because it takes a while. CI
 #       runs it explicitly.
-lint: lint/shellcheck lint/go lint/ts lint/examples lint/helm lint/site-icons lint/markdown lint/actions/actionlint lint/check-scopes
+lint: lint/shellcheck lint/go lint/ts lint/examples lint/helm lint/site-icons lint/markdown lint/actions/actionlint lint/check-scopes lint/migrations
 .PHONY: lint

 lint/site-icons:
@@ -619,6 +622,12 @@ lint/check-scopes: coderd/database/dump.sql
 	go run ./scripts/check-scopes
 .PHONY: lint/check-scopes

+# Verify migrations do not hardcode the public schema.
+lint/migrations:
+	./scripts/check_pg_schema.sh "Migrations" $(MIGRATION_FILES)
+	./scripts/check_pg_schema.sh "Fixtures" $(FIXTURE_FILES)
+.PHONY: lint/migrations
+
 # 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 := \
@@ -40,6 +40,7 @@ import (
 	"github.com/coder/clistat"
 	"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/agentscripts"
 	"github.com/coder/coder/v2/agent/agentsocket"
 	"github.com/coder/coder/v2/agent/agentssh"
@@ -295,6 +296,8 @@ type agent struct {
 	containerAPIOptions []agentcontainers.Option
 	containerAPI        *agentcontainers.API

+	filesAPI *agentfiles.API
+
 	socketServerEnabled bool
 	socketPath          string
 	socketServer        *agentsocket.Server
@@ -365,6 +368,8 @@ func (a *agent) init() {

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

+	a.filesAPI = agentfiles.NewAPI(a.logger.Named("files"), a.filesystem)
+
 	a.reconnectingPTYServer = reconnectingpty.NewServer(
 		a.logger.Named("reconnecting-pty"),
 		a.sshServer,
@@ -877,12 +882,16 @@ const (
 )

 func (a *agent) reportConnection(id uuid.UUID, connectionType proto.Connection_Type, ip string) (disconnected func(code int, reason string)) {
-	// Remove the port from the IP because ports are not supported in coderd.
-	if host, _, err := net.SplitHostPort(ip); err != nil {
-		a.logger.Error(a.hardCtx, "split host and port for connection report failed", slog.F("ip", ip), slog.Error(err))
-	} else {
-		// Best effort.
-		ip = host
+	// A blank IP can unfortunately happen if the connection is broken in a data race before we get to introspect it. We
+	// still report it, and the recipient can handle a blank IP.
+	if ip != "" {
+		// Remove the port from the IP because ports are not supported in coderd.
+		if host, _, err := net.SplitHostPort(ip); err != nil {
+			a.logger.Error(a.hardCtx, "split host and port for connection report failed", slog.F("ip", ip), slog.Error(err))
+		} else {
+			// Best effort.
+			ip = host
+		}
 	}

 	// If the IP is "localhost" (which it can be in some cases), set it to
@@ -121,7 +121,8 @@ func TestAgent_ImmediateClose(t *testing.T) {
 	require.NoError(t, err)
 }

-// NOTE: These tests only work when your default shell is bash for some reason.
+// NOTE(Cian): I noticed that these tests would fail when my default shell was zsh.
+//             Writing "exit 0" to stdin before closing fixed the issue for me.

 func TestAgent_Stats_SSH(t *testing.T) {
 	t.Parallel()
@@ -148,16 +149,37 @@ func TestAgent_Stats_SSH(t *testing.T) {
 			require.NoError(t, err)

 			var s *proto.Stats
+			// We are looking for four different stats to be reported. They might not all
+			// arrive at the same time, so we loop until we've seen them all.
+			var connectionCountSeen, rxBytesSeen, txBytesSeen, sessionCountSSHSeen bool
 			require.Eventuallyf(t, func() bool {
 				var ok bool
 				s, ok = <-stats
-				return ok && s.ConnectionCount > 0 && s.RxBytes > 0 && s.TxBytes > 0 && s.SessionCountSsh == 1
+				if !ok {
+					return false
+				}
+				if s.ConnectionCount > 0 {
+					connectionCountSeen = true
+				}
+				if s.RxBytes > 0 {
+					rxBytesSeen = true
+				}
+				if s.TxBytes > 0 {
+					txBytesSeen = true
+				}
+				if s.SessionCountSsh == 1 {
+					sessionCountSSHSeen = true
+				}
+				return connectionCountSeen && rxBytesSeen && txBytesSeen && sessionCountSSHSeen
 			}, testutil.WaitLong, testutil.IntervalFast,
-				"never saw stats: %+v", s,
+				"never saw all stats: %+v, saw connectionCount: %t, rxBytes: %t, txBytes: %t, sessionCountSsh: %t",
+				s, connectionCountSeen, rxBytesSeen, txBytesSeen, sessionCountSSHSeen,
 			)
+			_, err = stdin.Write([]byte("exit 0\n"))
+			require.NoError(t, err, "writing exit to stdin")
 			_ = stdin.Close()
 			err = session.Wait()
-			require.NoError(t, err)
+			require.NoError(t, err, "waiting for session to exit")
 		})
 	}
 }
@@ -183,12 +205,31 @@ func TestAgent_Stats_ReconnectingPTY(t *testing.T) {
 	require.NoError(t, err)

 	var s *proto.Stats
+	// We are looking for four different stats to be reported. They might not all
+	// arrive at the same time, so we loop until we've seen them all.
+	var connectionCountSeen, rxBytesSeen, txBytesSeen, sessionCountReconnectingPTYSeen bool
 	require.Eventuallyf(t, func() bool {
 		var ok bool
 		s, ok = <-stats
-		return ok && s.ConnectionCount > 0 && s.RxBytes > 0 && s.TxBytes > 0 && s.SessionCountReconnectingPty == 1
+		if !ok {
+			return false
+		}
+		if s.ConnectionCount > 0 {
+			connectionCountSeen = true
+		}
+		if s.RxBytes > 0 {
+			rxBytesSeen = true
+		}
+		if s.TxBytes > 0 {
+			txBytesSeen = true
+		}
+		if s.SessionCountReconnectingPty == 1 {
+			sessionCountReconnectingPTYSeen = true
+		}
+		return connectionCountSeen && rxBytesSeen && txBytesSeen && sessionCountReconnectingPTYSeen
 	}, testutil.WaitLong, testutil.IntervalFast,
-		"never saw stats: %+v", s,
+		"never saw all stats: %+v, saw connectionCount: %t, rxBytes: %t, txBytes: %t, sessionCountReconnectingPTY: %t",
+		s, connectionCountSeen, rxBytesSeen, txBytesSeen, sessionCountReconnectingPTYSeen,
 	)
 }

@@ -218,9 +259,10 @@ func TestAgent_Stats_Magic(t *testing.T) {
 		require.NoError(t, err)
 		require.Equal(t, expected, strings.TrimSpace(string(output)))
 	})
+
 	t.Run("TracksVSCode", func(t *testing.T) {
 		t.Parallel()
-		if runtime.GOOS == "window" {
+		if runtime.GOOS == "windows" {
 			t.Skip("Sleeping for infinity doesn't work on Windows")
 		}
 		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
@@ -252,7 +294,9 @@ func TestAgent_Stats_Magic(t *testing.T) {
 		}, testutil.WaitLong, testutil.IntervalFast,
 			"never saw stats",
 		)
-		// The shell will automatically exit if there is no stdin!
+
+		_, err = stdin.Write([]byte("exit 0\n"))
+		require.NoError(t, err, "writing exit to stdin")
 		_ = stdin.Close()
 		err = session.Wait()
 		require.NoError(t, err)
@@ -3633,9 +3677,11 @@ func TestAgent_Metrics_SSH(t *testing.T) {
 		}
 	}

+	_, err = stdin.Write([]byte("exit 0\n"))
+	require.NoError(t, err, "writing exit to stdin")
 	_ = stdin.Close()
 	err = session.Wait()
-	require.NoError(t, err)
+	require.NoError(t, err, "waiting for session to exit")
 }

 // echoOnce accepts a single connection, reads 4 bytes and echos them back
@@ -779,10 +779,13 @@ func (api *API) watchContainers(rw http.ResponseWriter, r *http.Request) {
 	// close frames.
 	_ = conn.CloseRead(context.Background())

+	ctx, cancel := context.WithCancel(ctx)
+	defer cancel()
+
 	ctx, wsNetConn := codersdk.WebsocketNetConn(ctx, conn, websocket.MessageText)
 	defer wsNetConn.Close()

-	go httpapi.Heartbeat(ctx, conn)
+	go httpapi.HeartbeatClose(ctx, api.logger, cancel, conn)

 	updateCh := make(chan struct{}, 1)

@@ -0,0 +1,36 @@
+package agentfiles
+
+import (
+	"net/http"
+
+	"github.com/go-chi/chi/v5"
+	"github.com/spf13/afero"
+
+	"cdr.dev/slog/v3"
+)
+
+// API exposes file-related operations performed through the agent.
+type API struct {
+	logger     slog.Logger
+	filesystem afero.Fs
+}
+
+func NewAPI(logger slog.Logger, filesystem afero.Fs) *API {
+	api := &API{
+		logger:     logger,
+		filesystem: filesystem,
+	}
+	return api
+}
+
+// Routes returns the HTTP handler for file-related routes.
+func (api *API) Routes() http.Handler {
+	r := chi.NewRouter()
+
+	r.Post("/list-directory", api.HandleLS)
+	r.Get("/read-file", api.HandleReadFile)
+	r.Post("/write-file", api.HandleWriteFile)
+	r.Post("/edit-files", api.HandleEditFiles)
+
+	return r
+}
@@ -1,4 +1,4 @@
-package agent
+package agentfiles

 import (
 	"context"
@@ -25,7 +25,7 @@ import (

 type HTTPResponseCode = int

-func (a *agent) HandleReadFile(rw http.ResponseWriter, r *http.Request) {
+func (api *API) HandleReadFile(rw http.ResponseWriter, r *http.Request) {
 	ctx := r.Context()

 	query := r.URL.Query()
@@ -42,7 +42,7 @@ func (a *agent) HandleReadFile(rw http.ResponseWriter, r *http.Request) {
 		return
 	}

-	status, err := a.streamFile(ctx, rw, path, offset, limit)
+	status, err := api.streamFile(ctx, rw, path, offset, limit)
 	if err != nil {
 		httpapi.Write(ctx, rw, status, codersdk.Response{
 			Message: err.Error(),
@@ -51,12 +51,12 @@ func (a *agent) HandleReadFile(rw http.ResponseWriter, r *http.Request) {
 	}
 }

-func (a *agent) streamFile(ctx context.Context, rw http.ResponseWriter, path string, offset, limit int64) (HTTPResponseCode, error) {
+func (api *API) streamFile(ctx context.Context, rw http.ResponseWriter, path string, offset, limit int64) (HTTPResponseCode, error) {
 	if !filepath.IsAbs(path) {
 		return http.StatusBadRequest, xerrors.Errorf("file path must be absolute: %q", path)
 	}

-	f, err := a.filesystem.Open(path)
+	f, err := api.filesystem.Open(path)
 	if err != nil {
 		status := http.StatusInternalServerError
 		switch {
@@ -97,13 +97,13 @@ func (a *agent) streamFile(ctx context.Context, rw http.ResponseWriter, path str
 	reader := io.NewSectionReader(f, offset, bytesToRead)
 	_, err = io.Copy(rw, reader)
 	if err != nil && !errors.Is(err, io.EOF) && ctx.Err() == nil {
-		a.logger.Error(ctx, "workspace agent read file", slog.Error(err))
+		api.logger.Error(ctx, "workspace agent read file", slog.Error(err))
 	}

 	return 0, nil
 }

-func (a *agent) HandleWriteFile(rw http.ResponseWriter, r *http.Request) {
+func (api *API) HandleWriteFile(rw http.ResponseWriter, r *http.Request) {
 	ctx := r.Context()

 	query := r.URL.Query()
@@ -118,7 +118,7 @@ func (a *agent) HandleWriteFile(rw http.ResponseWriter, r *http.Request) {
 		return
 	}

-	status, err := a.writeFile(ctx, r, path)
+	status, err := api.writeFile(ctx, r, path)
 	if err != nil {
 		httpapi.Write(ctx, rw, status, codersdk.Response{
 			Message: err.Error(),
@@ -131,13 +131,13 @@ func (a *agent) HandleWriteFile(rw http.ResponseWriter, r *http.Request) {
 	})
 }

-func (a *agent) writeFile(ctx context.Context, r *http.Request, path string) (HTTPResponseCode, error) {
+func (api *API) writeFile(ctx context.Context, r *http.Request, path string) (HTTPResponseCode, error) {
 	if !filepath.IsAbs(path) {
 		return http.StatusBadRequest, xerrors.Errorf("file path must be absolute: %q", path)
 	}

 	dir := filepath.Dir(path)
-	err := a.filesystem.MkdirAll(dir, 0o755)
+	err := api.filesystem.MkdirAll(dir, 0o755)
 	if err != nil {
 		status := http.StatusInternalServerError
 		switch {
@@ -149,7 +149,7 @@ func (a *agent) writeFile(ctx context.Context, r *http.Request, path string) (HT
 		return status, err
 	}

-	f, err := a.filesystem.Create(path)
+	f, err := api.filesystem.Create(path)
 	if err != nil {
 		status := http.StatusInternalServerError
 		switch {
@@ -164,13 +164,13 @@ func (a *agent) writeFile(ctx context.Context, r *http.Request, path string) (HT

 	_, err = io.Copy(f, r.Body)
 	if err != nil && !errors.Is(err, io.EOF) && ctx.Err() == nil {
-		a.logger.Error(ctx, "workspace agent write file", slog.Error(err))
+		api.logger.Error(ctx, "workspace agent write file", slog.Error(err))
 	}

 	return 0, nil
 }

-func (a *agent) HandleEditFiles(rw http.ResponseWriter, r *http.Request) {
+func (api *API) HandleEditFiles(rw http.ResponseWriter, r *http.Request) {
 	ctx := r.Context()

 	var req workspacesdk.FileEditRequest
@@ -188,7 +188,7 @@ func (a *agent) HandleEditFiles(rw http.ResponseWriter, r *http.Request) {
 	var combinedErr error
 	status := http.StatusOK
 	for _, edit := range req.Files {
-		s, err := a.editFile(r.Context(), edit.Path, edit.Edits)
+		s, err := api.editFile(r.Context(), edit.Path, edit.Edits)
 		// Keep the highest response status, so 500 will be preferred over 400, etc.
 		if s > status {
 			status = s
@@ -210,7 +210,7 @@ func (a *agent) HandleEditFiles(rw http.ResponseWriter, r *http.Request) {
 	})
 }

-func (a *agent) editFile(ctx context.Context, path string, edits []workspacesdk.FileEdit) (int, error) {
+func (api *API) editFile(ctx context.Context, path string, edits []workspacesdk.FileEdit) (int, error) {
 	if path == "" {
 		return http.StatusBadRequest, xerrors.New("\"path\" is required")
 	}
@@ -223,7 +223,7 @@ func (a *agent) editFile(ctx context.Context, path string, edits []workspacesdk.
 		return http.StatusBadRequest, xerrors.New("must specify at least one edit")
 	}

-	f, err := a.filesystem.Open(path)
+	f, err := api.filesystem.Open(path)
 	if err != nil {
 		status := http.StatusInternalServerError
 		switch {
@@ -252,7 +252,7 @@ func (a *agent) editFile(ctx context.Context, path string, edits []workspacesdk.

 	// Create an adjacent file to ensure it will be on the same device and can be
 	// moved atomically.
-	tmpfile, err := afero.TempFile(a.filesystem, filepath.Dir(path), filepath.Base(path))
+	tmpfile, err := afero.TempFile(api.filesystem, filepath.Dir(path), filepath.Base(path))
 	if err != nil {
 		return http.StatusInternalServerError, err
 	}
@@ -260,13 +260,13 @@ func (a *agent) editFile(ctx context.Context, path string, edits []workspacesdk.

 	_, err = io.Copy(tmpfile, replace.Chain(f, transforms...))
 	if err != nil {
-		if rerr := a.filesystem.Remove(tmpfile.Name()); rerr != nil {
-			a.logger.Warn(ctx, "unable to clean up temp file", slog.Error(rerr))
+		if rerr := api.filesystem.Remove(tmpfile.Name()); rerr != nil {
+			api.logger.Warn(ctx, "unable to clean up temp file", slog.Error(rerr))
 		}
 		return http.StatusInternalServerError, xerrors.Errorf("edit %s: %w", path, err)
 	}

-	err = a.filesystem.Rename(tmpfile.Name(), path)
+	err = api.filesystem.Rename(tmpfile.Name(), path)
 	if err != nil {
 		return http.StatusInternalServerError, err
 	}
@@ -1,11 +1,13 @@
-package agent_test
+package agentfiles_test

 import (
 	"bytes"
 	"context"
+	"encoding/json"
 	"fmt"
 	"io"
 	"net/http"
+	"net/http/httptest"
 	"os"
 	"path/filepath"
 	"runtime"
@@ -16,10 +18,10 @@ import (
 	"github.com/stretchr/testify/require"
 	"golang.org/x/xerrors"

-	"github.com/coder/coder/v2/agent"
-	"github.com/coder/coder/v2/agent/agenttest"
-	"github.com/coder/coder/v2/coderd/coderdtest"
-	"github.com/coder/coder/v2/codersdk/agentsdk"
+	"cdr.dev/slog/v3"
+	"cdr.dev/slog/v3/sloggers/slogtest"
+	"github.com/coder/coder/v2/agent/agentfiles"
+	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/codersdk/workspacesdk"
 	"github.com/coder/coder/v2/testutil"
 )
@@ -106,15 +108,15 @@ func TestReadFile(t *testing.T) {

 	tmpdir := os.TempDir()
 	noPermsFilePath := filepath.Join(tmpdir, "no-perms")
-	//nolint:dogsled
-	conn, _, _, fs, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, opts *agent.Options) {
-		opts.Filesystem = newTestFs(opts.Filesystem, func(call, file string) error {
-			if file == noPermsFilePath {
-				return os.ErrPermission
-			}
-			return nil
-		})
+
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true}).Leveled(slog.LevelDebug)
+	fs := newTestFs(afero.NewMemMapFs(), func(call, file string) error {
+		if file == noPermsFilePath {
+			return os.ErrPermission
+		}
+		return nil
 	})
+	api := agentfiles.NewAPI(logger, fs)

 	dirPath := filepath.Join(tmpdir, "a-directory")
 	err := fs.MkdirAll(dirPath, 0o755)
@@ -260,19 +262,22 @@ func TestReadFile(t *testing.T) {
 			ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
 			defer cancel()

-			reader, mimeType, err := conn.ReadFile(ctx, tt.path, tt.offset, tt.limit)
+			w := httptest.NewRecorder()
+			r := httptest.NewRequestWithContext(ctx, http.MethodGet, fmt.Sprintf("/read-file?path=%s&offset=%d&limit=%d", tt.path, tt.offset, tt.limit), nil)
+			api.Routes().ServeHTTP(w, r)
+
 			if tt.errCode != 0 {
-				require.Error(t, err)
-				cerr := coderdtest.SDKError(t, err)
-				require.Contains(t, cerr.Error(), tt.error)
-				require.Equal(t, tt.errCode, cerr.StatusCode())
-			} else {
+				got := &codersdk.Error{}
+				err := json.NewDecoder(w.Body).Decode(got)
 				require.NoError(t, err)
-				defer reader.Close()
-				bytes, err := io.ReadAll(reader)
+				require.ErrorContains(t, got, tt.error)
+				require.Equal(t, tt.errCode, w.Code)
+			} else {
+				bytes, err := io.ReadAll(w.Body)
 				require.NoError(t, err)
 				require.Equal(t, tt.bytes, bytes)
-				require.Equal(t, tt.mimeType, mimeType)
+				require.Equal(t, tt.mimeType, w.Header().Get("Content-Type"))
+				require.Equal(t, http.StatusOK, w.Code)
 			}
 		})
 	}
@@ -284,15 +289,14 @@ func TestWriteFile(t *testing.T) {
 	tmpdir := os.TempDir()
 	noPermsFilePath := filepath.Join(tmpdir, "no-perms-file")
 	noPermsDirPath := filepath.Join(tmpdir, "no-perms-dir")
-	//nolint:dogsled
-	conn, _, _, fs, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, opts *agent.Options) {
-		opts.Filesystem = newTestFs(opts.Filesystem, func(call, file string) error {
-			if file == noPermsFilePath || file == noPermsDirPath {
-				return os.ErrPermission
-			}
-			return nil
-		})
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true}).Leveled(slog.LevelDebug)
+	fs := newTestFs(afero.NewMemMapFs(), func(call, file string) error {
+		if file == noPermsFilePath || file == noPermsDirPath {
+			return os.ErrPermission
+		}
+		return nil
 	})
+	api := agentfiles.NewAPI(logger, fs)

 	dirPath := filepath.Join(tmpdir, "directory")
 	err := fs.MkdirAll(dirPath, 0o755)
@@ -371,17 +375,21 @@ func TestWriteFile(t *testing.T) {
 			defer cancel()

 			reader := bytes.NewReader(tt.bytes)
-			err := conn.WriteFile(ctx, tt.path, reader)
+			w := httptest.NewRecorder()
+			r := httptest.NewRequestWithContext(ctx, http.MethodPost, fmt.Sprintf("/write-file?path=%s", tt.path), reader)
+			api.Routes().ServeHTTP(w, r)
+
 			if tt.errCode != 0 {
-				require.Error(t, err)
-				cerr := coderdtest.SDKError(t, err)
-				require.Contains(t, cerr.Error(), tt.error)
-				require.Equal(t, tt.errCode, cerr.StatusCode())
+				got := &codersdk.Error{}
+				err := json.NewDecoder(w.Body).Decode(got)
+				require.NoError(t, err)
+				require.ErrorContains(t, got, tt.error)
+				require.Equal(t, tt.errCode, w.Code)
 			} else {
+				bytes, err := afero.ReadFile(fs, tt.path)
 				require.NoError(t, err)
-				b, err := afero.ReadFile(fs, tt.path)
-				require.NoError(t, err)
-				require.Equal(t, tt.bytes, b)
+				require.Equal(t, tt.bytes, bytes)
+				require.Equal(t, http.StatusOK, w.Code)
 			}
 		})
 	}
@@ -393,21 +401,20 @@ func TestEditFiles(t *testing.T) {
 	tmpdir := os.TempDir()
 	noPermsFilePath := filepath.Join(tmpdir, "no-perms-file")
 	failRenameFilePath := filepath.Join(tmpdir, "fail-rename")
-	//nolint:dogsled
-	conn, _, _, fs, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, opts *agent.Options) {
-		opts.Filesystem = newTestFs(opts.Filesystem, func(call, file string) error {
-			if file == noPermsFilePath {
-				return &os.PathError{
-					Op:   call,
-					Path: file,
-					Err:  os.ErrPermission,
-				}
-			} else if file == failRenameFilePath && call == "rename" {
-				return xerrors.New("rename failed")
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true}).Leveled(slog.LevelDebug)
+	fs := newTestFs(afero.NewMemMapFs(), func(call, file string) error {
+		if file == noPermsFilePath {
+			return &os.PathError{
+				Op:   call,
+				Path: file,
+				Err:  os.ErrPermission,
 			}
-			return nil
-		})
+		} else if file == failRenameFilePath && call == "rename" {
+			return xerrors.New("rename failed")
+		}
+		return nil
 	})
+	api := agentfiles.NewAPI(logger, fs)

 	dirPath := filepath.Join(tmpdir, "directory")
 	err := fs.MkdirAll(dirPath, 0o755)
@@ -701,16 +708,26 @@ func TestEditFiles(t *testing.T) {
 				require.NoError(t, err)
 			}

-			err := conn.EditFiles(ctx, workspacesdk.FileEditRequest{Files: tt.edits})
+			buf := bytes.NewBuffer(nil)
+			enc := json.NewEncoder(buf)
+			enc.SetEscapeHTML(false)
+			err := enc.Encode(workspacesdk.FileEditRequest{Files: tt.edits})
+			require.NoError(t, err)
+
+			w := httptest.NewRecorder()
+			r := httptest.NewRequestWithContext(ctx, http.MethodPost, "/edit-files", buf)
+			api.Routes().ServeHTTP(w, r)
+
 			if tt.errCode != 0 {
-				require.Error(t, err)
-				cerr := coderdtest.SDKError(t, err)
-				for _, error := range tt.errors {
-					require.Contains(t, cerr.Error(), error)
-				}
-				require.Equal(t, tt.errCode, cerr.StatusCode())
-			} else {
+				got := &codersdk.Error{}
+				err := json.NewDecoder(w.Body).Decode(got)
 				require.NoError(t, err)
+				for _, error := range tt.errors {
+					require.ErrorContains(t, got, error)
+				}
+				require.Equal(t, tt.errCode, w.Code)
+			} else {
+				require.Equal(t, http.StatusOK, w.Code)
 			}
 			for path, expect := range tt.expected {
 				b, err := afero.ReadFile(fs, path)
@@ -1,4 +1,4 @@
-package agent
+package agentfiles

 import (
 	"errors"
@@ -21,7 +21,7 @@ import (

 var WindowsDriveRegex = regexp.MustCompile(`^[a-zA-Z]:\\$`)

-func (a *agent) HandleLS(rw http.ResponseWriter, r *http.Request) {
+func (api *API) HandleLS(rw http.ResponseWriter, r *http.Request) {
 	ctx := r.Context()

 	// An absolute path may be optionally provided, otherwise a path split into an
@@ -43,7 +43,7 @@ func (a *agent) HandleLS(rw http.ResponseWriter, r *http.Request) {
 		return
 	}

-	resp, err := listFiles(a.filesystem, path, req)
+	resp, err := listFiles(api.filesystem, path, req)
 	if err != nil {
 		status := http.StatusInternalServerError
 		switch {
@@ -1,4 +1,4 @@
-package agent
+package agentfiles

 import (
 	"os"
@@ -27,6 +27,8 @@ func (a *agent) apiHandler() http.Handler {
 		})
 	})

+	r.Mount("/api/v0", a.filesAPI.Routes())
+
 	if a.devcontainers {
 		r.Mount("/api/v0/containers", a.containerAPI.Routes())
 	} else if manifest := a.manifest.Load(); manifest != nil && manifest.ParentID != uuid.Nil {
@@ -49,10 +51,6 @@ func (a *agent) apiHandler() http.Handler {

 	r.Get("/api/v0/listening-ports", a.listeningPortsHandler.handler)
 	r.Get("/api/v0/netcheck", a.HandleNetcheck)
-	r.Post("/api/v0/list-directory", a.HandleLS)
-	r.Get("/api/v0/read-file", a.HandleReadFile)
-	r.Post("/api/v0/write-file", a.HandleWriteFile)
-	r.Post("/api/v0/edit-files", a.HandleEditFiles)
 	r.Get("/debug/logs", a.HandleHTTPDebugLogs)
 	r.Get("/debug/magicsock", a.HandleHTTPDebugMagicsock)
 	r.Get("/debug/magicsock/debug-logging/{state}", a.HandleHTTPMagicsockDebugLoggingState)
@@ -78,9 +78,13 @@ func TestBoundaryLogs_EndToEnd(t *testing.T) {
 	sink := &logSink{}
 	logger := slog.Make(sink)
 	workspaceID := uuid.New()
+	templateID := uuid.New()
+	templateVersionID := uuid.New()
 	reporter := &agentapi.BoundaryLogsAPI{
-		Log:         logger,
-		WorkspaceID: workspaceID,
+		Log:               logger,
+		WorkspaceID:       workspaceID,
+		TemplateID:        templateID,
+		TemplateVersionID: templateVersionID,
 	}

 	ctx, cancel := context.WithCancel(context.Background())
@@ -123,6 +127,8 @@ func TestBoundaryLogs_EndToEnd(t *testing.T) {
 	require.Equal(t, "boundary_request", entry.Message)
 	require.Equal(t, "allow", getField(entry.Fields, "decision"))
 	require.Equal(t, workspaceID.String(), getField(entry.Fields, "workspace_id"))
+	require.Equal(t, templateID.String(), getField(entry.Fields, "template_id"))
+	require.Equal(t, templateVersionID.String(), getField(entry.Fields, "template_version_id"))
 	require.Equal(t, "GET", getField(entry.Fields, "http_method"))
 	require.Equal(t, "https://example.com/allowed", getField(entry.Fields, "http_url"))
 	require.Equal(t, "*.example.com", getField(entry.Fields, "matched_rule"))
@@ -155,6 +161,8 @@ func TestBoundaryLogs_EndToEnd(t *testing.T) {
 	require.Equal(t, "boundary_request", entry.Message)
 	require.Equal(t, "deny", getField(entry.Fields, "decision"))
 	require.Equal(t, workspaceID.String(), getField(entry.Fields, "workspace_id"))
+	require.Equal(t, templateID.String(), getField(entry.Fields, "template_id"))
+	require.Equal(t, templateVersionID.String(), getField(entry.Fields, "template_version_id"))
 	require.Equal(t, "POST", getField(entry.Fields, "http_method"))
 	require.Equal(t, "https://blocked.com/denied", getField(entry.Fields, "http_url"))
 	require.Equal(t, nil, getField(entry.Fields, "matched_rule"))
@@ -81,6 +81,10 @@ type BackedPipe struct {
 	// Unified error handling with generation filtering
 	errChan chan ErrorEvent

+	// forceReconnectHook is a test hook invoked after ForceReconnect registers
+	// with the singleflight group.
+	forceReconnectHook func()
+
 	// singleflight group to dedupe concurrent ForceReconnect calls
 	sf singleflight.Group

@@ -324,6 +328,13 @@ func (bp *BackedPipe) handleConnectionError(errorEvt ErrorEvent) {
 	}
 }

+// SetForceReconnectHookForTests sets a hook invoked after ForceReconnect
+// registers with the singleflight group. It must be set before any
+// concurrent ForceReconnect calls.
+func (bp *BackedPipe) SetForceReconnectHookForTests(hook func()) {
+	bp.forceReconnectHook = hook
+}
+
 // ForceReconnect forces a reconnection attempt immediately.
 // This can be used to force a reconnection if a new connection is established.
 // It prevents duplicate reconnections when called concurrently.
@@ -331,7 +342,7 @@ func (bp *BackedPipe) ForceReconnect() error {
 	// Deduplicate concurrent ForceReconnect calls so only one reconnection
 	// attempt runs at a time from this API. Use the pipe's internal context
 	// to ensure Close() cancels any in-flight attempt.
-	_, err, _ := bp.sf.Do("force-reconnect", func() (interface{}, error) {
+	resultChan := bp.sf.DoChan("force-reconnect", func() (interface{}, error) {
 		bp.mu.Lock()
 		defer bp.mu.Unlock()

@@ -346,5 +357,11 @@ func (bp *BackedPipe) ForceReconnect() error {

 		return nil, bp.reconnectLocked()
 	})
-	return err
+
+	if hook := bp.forceReconnectHook; hook != nil {
+		hook()
+	}
+
+	result := <-resultChan
+	return result.Err
 }
@@ -742,12 +742,15 @@ func TestBackedPipe_DuplicateReconnectionPrevention(t *testing.T) {

 	const numConcurrent = 3
 	startSignals := make([]chan struct{}, numConcurrent)
-	startedSignals := make([]chan struct{}, numConcurrent)
 	for i := range startSignals {
 		startSignals[i] = make(chan struct{})
-		startedSignals[i] = make(chan struct{})
 	}

+	enteredSignals := make(chan struct{}, numConcurrent)
+	bp.SetForceReconnectHookForTests(func() {
+		enteredSignals <- struct{}{}
+	})
+
 	errors := make([]error, numConcurrent)
 	var wg sync.WaitGroup

@@ -758,15 +761,12 @@ func TestBackedPipe_DuplicateReconnectionPrevention(t *testing.T) {
 			defer wg.Done()
 			// Wait for the signal to start
 			<-startSignals[idx]
-			// Signal that we're about to call ForceReconnect
-			close(startedSignals[idx])
 			errors[idx] = bp.ForceReconnect()
 		}(i)
 	}

 	// Start the first ForceReconnect and wait for it to block
 	close(startSignals[0])
-	<-startedSignals[0]

 	// Wait for the first reconnect to actually start and block
 	testutil.RequireReceive(testCtx, t, blockedChan)
@@ -777,9 +777,9 @@ func TestBackedPipe_DuplicateReconnectionPrevention(t *testing.T) {
 		close(startSignals[i])
 	}

-	// Wait for all additional goroutines to have started their calls
-	for i := 1; i < numConcurrent; i++ {
-		<-startedSignals[i]
+	// Wait for all ForceReconnect calls to join the singleflight operation.
+	for i := 0; i < numConcurrent; i++ {
+		testutil.RequireReceive(testCtx, t, enteredSignals)
 	}

 	// At this point, one reconnect has started and is blocked,
@@ -7,6 +7,6 @@ func IsInitProcess() bool {
 	return false
 }

-func ForkReap(_ ...Option) error {
-	return nil
+func ForkReap(_ ...Option) (int, error) {
+	return 0, nil
 }
@@ -32,12 +32,13 @@ func TestReap(t *testing.T) {
 	}

 	pids := make(reap.PidCh, 1)
-	err := reaper.ForkReap(
+	exitCode, err := reaper.ForkReap(
 		reaper.WithPIDCallback(pids),
 		// Provide some argument that immediately exits.
 		reaper.WithExecArgs("/bin/sh", "-c", "exit 0"),
 	)
 	require.NoError(t, err)
+	require.Equal(t, 0, exitCode)

 	cmd := exec.Command("tail", "-f", "/dev/null")
 	err = cmd.Start()
@@ -65,6 +66,36 @@ func TestReap(t *testing.T) {
 	}
 }

+//nolint:paralleltest
+func TestForkReapExitCodes(t *testing.T) {
+	if testutil.InCI() {
+		t.Skip("Detected CI, skipping reaper tests")
+	}
+
+	tests := []struct {
+		name         string
+		command      string
+		expectedCode int
+	}{
+		{"exit 0", "exit 0", 0},
+		{"exit 1", "exit 1", 1},
+		{"exit 42", "exit 42", 42},
+		{"exit 255", "exit 255", 255},
+		{"SIGKILL", "kill -9 $$", 128 + 9},
+		{"SIGTERM", "kill -15 $$", 128 + 15},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			exitCode, err := reaper.ForkReap(
+				reaper.WithExecArgs("/bin/sh", "-c", tt.command),
+			)
+			require.NoError(t, err)
+			require.Equal(t, tt.expectedCode, exitCode, "exit code mismatch for %q", tt.command)
+		})
+	}
+}
+
 //nolint:paralleltest // Signal handling.
 func TestReapInterrupt(t *testing.T) {
 	// Don't run the reaper test in CI. It does weird
@@ -84,13 +115,17 @@ func TestReapInterrupt(t *testing.T) {
 	defer signal.Stop(usrSig)

 	go func() {
-		errC <- reaper.ForkReap(
+		exitCode, err := reaper.ForkReap(
 			reaper.WithPIDCallback(pids),
 			reaper.WithCatchSignals(os.Interrupt),
 			// Signal propagation does not extend to children of children, so
 			// we create a little bash script to ensure sleep is interrupted.
 			reaper.WithExecArgs("/bin/sh", "-c", fmt.Sprintf("pid=0; trap 'kill -USR2 %d; kill -TERM $pid' INT; sleep 10 &\npid=$!; kill -USR1 %d; wait", os.Getpid(), os.Getpid())),
 		)
+		// The child exits with 128 + SIGTERM (15) = 143, but the trap catches
+		// SIGINT and sends SIGTERM to the sleep process, so exit code varies.
+		_ = exitCode
+		errC <- err
 	}()

 	require.Equal(t, <-usrSig, syscall.SIGUSR1)
@@ -40,7 +40,10 @@ func catchSignals(pid int, sigs []os.Signal) {
 // the reaper and an exec.Command waiting for its process to complete.
 // The provided 'pids' channel may be nil if the caller does not care about the
 // reaped children PIDs.
-func ForkReap(opt ...Option) error {
+//
+// Returns the child's exit code (using 128+signal for signal termination)
+// and any error from Wait4.
+func ForkReap(opt ...Option) (int, error) {
 	opts := &options{
 		ExecArgs: os.Args,
 	}
@@ -53,7 +56,7 @@ func ForkReap(opt ...Option) error {

 	pwd, err := os.Getwd()
 	if err != nil {
-		return xerrors.Errorf("get wd: %w", err)
+		return 1, xerrors.Errorf("get wd: %w", err)
 	}

 	pattrs := &syscall.ProcAttr{
@@ -72,7 +75,7 @@ func ForkReap(opt ...Option) error {
 	//#nosec G204
 	pid, err := syscall.ForkExec(opts.ExecArgs[0], opts.ExecArgs, pattrs)
 	if err != nil {
-		return xerrors.Errorf("fork exec: %w", err)
+		return 1, xerrors.Errorf("fork exec: %w", err)
 	}

 	go catchSignals(pid, opts.CatchSignals)
@@ -82,5 +85,18 @@ func ForkReap(opt ...Option) error {
 	for xerrors.Is(err, syscall.EINTR) {
 		_, err = syscall.Wait4(pid, &wstatus, 0, nil)
 	}
-	return err
+
+	// Convert wait status to exit code using standard Unix conventions:
+	// - Normal exit: use the exit code
+	// - Signal termination: use 128 + signal number
+	var exitCode int
+	switch {
+	case wstatus.Exited():
+		exitCode = wstatus.ExitStatus()
+	case wstatus.Signaled():
+		exitCode = 128 + int(wstatus.Signal())
+	default:
+		exitCode = 1
+	}
+	return exitCode, err
 }
@@ -136,7 +136,7 @@ func workspaceAgent() *serpent.Command {
 				// to do this else we fork bomb ourselves.
 				//nolint:gocritic
 				args := append(os.Args, "--no-reap")
-				err := reaper.ForkReap(
+				exitCode, err := reaper.ForkReap(
 					reaper.WithExecArgs(args...),
 					reaper.WithCatchSignals(StopSignals...),
 				)
@@ -145,8 +145,8 @@ func workspaceAgent() *serpent.Command {
 					return xerrors.Errorf("fork reap: %w", err)
 				}

-				logger.Info(ctx, "reaper process exiting")
-				return nil
+				logger.Info(ctx, "reaper child process exited", slog.F("exit_code", exitCode))
+				return ExitError(exitCode, nil)
 			}

 			// Handle interrupt signals to allow for graceful shutdown,
@@ -10,12 +10,8 @@ import (
 	"github.com/coder/serpent"
 )

-func RichParameter(inv *serpent.Invocation, templateVersionParameter codersdk.TemplateVersionParameter, defaultOverrides map[string]string) (string, error) {
-	label := templateVersionParameter.Name
-	if templateVersionParameter.DisplayName != "" {
-		label = templateVersionParameter.DisplayName
-	}
-
+func RichParameter(inv *serpent.Invocation, templateVersionParameter codersdk.TemplateVersionParameter, name, defaultValue string) (string, error) {
+	label := name
 	if templateVersionParameter.Ephemeral {
 		label += pretty.Sprint(DefaultStyles.Warn, " (build option)")
 	}
@@ -26,11 +22,6 @@ func RichParameter(inv *serpent.Invocation, templateVersionParameter codersdk.Te
 		_, _ = fmt.Fprintln(inv.Stdout, "  "+strings.TrimSpace(strings.Join(strings.Split(templateVersionParameter.DescriptionPlaintext, "\n"), "\n  "))+"\n")
 	}

-	defaultValue := templateVersionParameter.DefaultValue
-	if v, ok := defaultOverrides[templateVersionParameter.Name]; ok {
-		defaultValue = v
-	}
-
 	var err error
 	var value string
 	switch {
@@ -32,12 +32,12 @@ type PromptOptions struct {
 const skipPromptFlag = "yes"

 // SkipPromptOption adds a "--yes/-y" flag to the cmd that can be used to skip
-// prompts.
+// confirmation prompts.
 func SkipPromptOption() serpent.Option {
 	return serpent.Option{
 		Flag:          skipPromptFlag,
 		FlagShorthand: "y",
-		Description:   "Bypass prompts.",
+		Description:   "Bypass confirmation prompts.",
 		// Discard
 		Value: serpent.BoolOf(new(bool)),
 	}
@@ -42,9 +42,10 @@ func (r *RootCmd) Create(opts CreateOptions) *serpent.Command {
 		stopAfter       time.Duration
 		workspaceName   string

-		parameterFlags     workspaceParameterFlags
-		autoUpdates        string
-		copyParametersFrom string
+		parameterFlags       workspaceParameterFlags
+		autoUpdates          string
+		copyParametersFrom   string
+		useParameterDefaults bool
 		// Organization context is only required if more than 1 template
 		// shares the same name across multiple organizations.
 		orgContext = NewOrganizationContext()
@@ -308,7 +309,7 @@ func (r *RootCmd) Create(opts CreateOptions) *serpent.Command {
 				displayAppliedPreset(inv, preset, presetParameters)
 			} else {
 				// Inform the user that no preset was applied
-				_, _ = fmt.Fprintf(inv.Stdout, "%s", cliui.Bold("No preset applied."))
+				_, _ = fmt.Fprintf(inv.Stdout, "%s\n", cliui.Bold("No preset applied."))
 			}

 			if opts.BeforeCreate != nil {
@@ -329,6 +330,8 @@ func (r *RootCmd) Create(opts CreateOptions) *serpent.Command {
 				RichParameterDefaults: cliBuildParameterDefaults,

 				SourceWorkspaceParameters: sourceWorkspaceParameters,
+
+				UseParameterDefaults: useParameterDefaults,
 			})
 			if err != nil {
 				return xerrors.Errorf("prepare build: %w", err)
@@ -435,6 +438,12 @@ func (r *RootCmd) Create(opts CreateOptions) *serpent.Command {
 			Description: "Specify the source workspace name to copy parameters from.",
 			Value:       serpent.StringOf(&copyParametersFrom),
 		},
+		serpent.Option{
+			Flag:        "use-parameter-defaults",
+			Env:         "CODER_WORKSPACE_USE_PARAMETER_DEFAULTS",
+			Description: "Automatically accept parameter defaults when no value is provided.",
+			Value:       serpent.BoolOf(&useParameterDefaults),
+		},
 		cliui.SkipPromptOption(),
 	)
 	cmd.Options = append(cmd.Options, parameterFlags.cliParameters()...)
@@ -459,6 +468,8 @@ type prepWorkspaceBuildArgs struct {
 	RichParameters        []codersdk.WorkspaceBuildParameter
 	RichParameterFile     string
 	RichParameterDefaults []codersdk.WorkspaceBuildParameter
+
+	UseParameterDefaults bool
 }

 // resolvePreset returns the preset matching the given presetName (if specified),
@@ -561,7 +572,8 @@ func prepWorkspaceBuild(inv *serpent.Invocation, client *codersdk.Client, args p
 		WithPromptRichParameters(args.PromptRichParameters).
 		WithRichParameters(args.RichParameters).
 		WithRichParametersFile(parameterFile).
-		WithRichParametersDefaults(args.RichParameterDefaults)
+		WithRichParametersDefaults(args.RichParameterDefaults).
+		WithUseParameterDefaults(args.UseParameterDefaults)
 	buildParameters, err := resolver.Resolve(inv, args.Action, templateVersionParameters)
 	if err != nil {
 		return nil, err
@@ -318,353 +318,437 @@ func prepareEchoResponses(parameters []*proto.RichParameter, presets ...*proto.P
 	}
 }

+type param struct {
+	name    string
+	ptype   string
+	value   string
+	mutable bool
+}
+
 func TestCreateWithRichParameters(t *testing.T) {
 	t.Parallel()

-	const (
-		firstParameterName        = "first_parameter"
-		firstParameterDescription = "This is first parameter"
-		firstParameterValue       = "1"
-
-		secondParameterName        = "second_parameter"
-		secondParameterDisplayName = "Second Parameter"
-		secondParameterDescription = "This is second parameter"
-		secondParameterValue       = "2"
-
-		immutableParameterName        = "third_parameter"
-		immutableParameterDescription = "This is not mutable parameter"
-		immutableParameterValue       = "4"
-	)
-
-	echoResponses := func() *echo.Responses {
-		return prepareEchoResponses([]*proto.RichParameter{
-			{Name: firstParameterName, Description: firstParameterDescription, Mutable: true},
-			{Name: secondParameterName, DisplayName: secondParameterDisplayName, Description: secondParameterDescription, Mutable: true},
-			{Name: immutableParameterName, Description: immutableParameterDescription, Mutable: false},
-		})
+	// Default parameters and their expected values.
+	params := []param{
+		{
+			name:    "number_param",
+			ptype:   "number",
+			value:   "777",
+			mutable: true,
+		},
+		{
+			name:    "string_param",
+			ptype:   "string",
+			value:   "qux",
+			mutable: true,
+		},
+		{
+			name: "bool_param",
+			// TODO: Setting the type breaks booleans.  It claims the default is false
+			// but when you then accept this default it errors saying that the value
+			// must be true or false.  For now, use a string.
+			ptype:   "string",
+			value:   "false",
+			mutable: true,
+		},
+		{
+			name:    "immutable_string_param",
+			ptype:   "string",
+			value:   "i am eternal",
+			mutable: false,
+		},
 	}

-	t.Run("InputParameters", func(t *testing.T) {
-		t.Parallel()
+	type testContext struct {
+		client        *codersdk.Client
+		member        *codersdk.Client
+		owner         codersdk.CreateFirstUserResponse
+		template      codersdk.Template
+		workspaceName string
+	}

-		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
-		owner := coderdtest.CreateFirstUser(t, client)
-		member, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
-		version := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, echoResponses())
-		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
+	tests := []struct {
+		name string
+		// setup runs before the command is started and return arguments that will
+		// be appended to the create command.
+		setup func() []string
+		// handlePty optionally runs after the command is started.  It should handle
+		// all expected prompts from the pty.
+		handlePty func(pty *ptytest.PTY)
+		// postRun runs after the command has finished but before the workspace is
+		// verified.  It must return the workspace name to check (used for the copy
+		// workspace tests).
+		postRun func(t *testing.T, args testContext) string
+		// errors contains expected errors.  The workspace will not be verified if
+		// errors are expected.
+		errors []string
+		// inputParameters overrides the default parameters.
+		inputParameters []param
+		// expectedParameters defaults to inputParameters.
+		expectedParameters []param
+		// withDefaults sets DefaultValue to each parameter's value.
+		withDefaults bool
+	}{
+		{
+			name: "ValuesFromPrompt",
+			handlePty: func(pty *ptytest.PTY) {
+				// Enter the value for each parameter as prompted.
+				for _, param := range params {
+					pty.ExpectMatch(param.name)
+					pty.WriteLine(param.value)
+				}
+				// Confirm the creation.
+				pty.ExpectMatch("Confirm create?")
+				pty.WriteLine("yes")
+			},
+		},
+		{
+			name: "ValuesFromDefaultFlags",
+			setup: func() []string {
+				// Provide the defaults on the command line.
+				args := []string{}
+				for _, param := range params {
+					args = append(args, "--parameter-default", fmt.Sprintf("%s=%s", param.name, param.value))
+				}
+				return args
+			},
+			handlePty: func(pty *ptytest.PTY) {
+				// Simply accept the defaults.
+				for _, param := range params {
+					pty.ExpectMatch(param.name)
+					pty.ExpectMatch(`Enter a value (default: "` + param.value + `")`)
+					pty.WriteLine("")
+				}
+				// Confirm the creation.
+				pty.ExpectMatch("Confirm create?")
+				pty.WriteLine("yes")
+			},
+		},
+		{
+			name: "ValuesFromFile",
+			setup: func() []string {
+				// Create a file with the values.
+				tempDir := t.TempDir()
+				removeTmpDirUntilSuccessAfterTest(t, tempDir)
+				parameterFile, _ := os.CreateTemp(tempDir, "testParameterFile*.yaml")
+				for _, param := range params {
+					_, err := parameterFile.WriteString(fmt.Sprintf("%s: %s\n", param.name, param.value))
+					require.NoError(t, err)
+				}

-		template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
+				return []string{"--rich-parameter-file", parameterFile.Name()}
+			},
+			handlePty: func(pty *ptytest.PTY) {
+				// No prompts, we only need to confirm.
+				pty.ExpectMatch("Confirm create?")
+				pty.WriteLine("yes")
+			},
+		},
+		{
+			name: "ValuesFromFlags",
+			setup: func() []string {
+				// Provide the values on the command line.
+				var args []string
+				for _, param := range params {
+					args = append(args, "--parameter", fmt.Sprintf("%s=%s", param.name, param.value))
+				}
+				return args
+			},
+			handlePty: func(pty *ptytest.PTY) {
+				// No prompts, we only need to confirm.
+				pty.ExpectMatch("Confirm create?")
+				pty.WriteLine("yes")
+			},
+		},
+		{
+			name: "MisspelledParameter",
+			setup: func() []string {
+				// Provide the values on the command line.
+				args := []string{}
+				for i, param := range params {
+					if i == 0 {
+						// Slightly misspell the first parameter with an extra character.
+						args = append(args, "--parameter", fmt.Sprintf("n%s=%s", param.name, param.value))
+					} else {
+						args = append(args, "--parameter", fmt.Sprintf("%s=%s", param.name, param.value))
+					}
+				}
+				return args
+			},
+			errors: []string{
+				"parameter \"n" + params[0].name + "\" is not present in the template",
+				"Did you mean: " + params[0].name,
+			},
+		},
+		{
+			name: "ValuesFromWorkspace",
+			setup: func() []string {
+				// Provide the values on the command line.
+				args := []string{"-y"}
+				for _, param := range params {
+					args = append(args, "--parameter", fmt.Sprintf("%s=%s", param.name, param.value))
+				}
+				return args
+			},
+			postRun: func(t *testing.T, tctx testContext) string {
+				inv, root := clitest.New(t, "create", "--copy-parameters-from", tctx.workspaceName, "other-workspace", "-y")
+				clitest.SetupConfig(t, tctx.member, root)
+				pty := ptytest.New(t).Attach(inv)
+				inv.Stdout = pty.Output()
+				inv.Stderr = pty.Output()
+				err := inv.Run()
+				require.NoError(t, err, "failed to create a workspace based on the source workspace")
+				return "other-workspace"
+			},
+		},
+		{
+			name: "ValuesFromOutdatedWorkspace",
+			setup: func() []string {
+				// Provide the values on the command line.
+				args := []string{"-y"}
+				for _, param := range params {
+					args = append(args, "--parameter", fmt.Sprintf("%s=%s", param.name, param.value))
+				}
+				return args
+			},
+			postRun: func(t *testing.T, tctx testContext) string {
+				// Update the template to a new version.
+				version2 := coderdtest.CreateTemplateVersion(t, tctx.client, tctx.owner.OrganizationID, prepareEchoResponses([]*proto.RichParameter{
+					{Name: "another_parameter", Type: "string", DefaultValue: "not-relevant"},
+				}), func(ctvr *codersdk.CreateTemplateVersionRequest) {
+					ctvr.TemplateID = tctx.template.ID
+				})
+				coderdtest.AwaitTemplateVersionJobCompleted(t, tctx.client, version2.ID)
+				coderdtest.UpdateActiveTemplateVersion(t, tctx.client, tctx.template.ID, version2.ID)

-		inv, root := clitest.New(t, "create", "my-workspace", "--template", template.Name)
-		clitest.SetupConfig(t, member, root)
-		doneChan := make(chan struct{})
-		pty := ptytest.New(t).Attach(inv)
-		go func() {
-			defer close(doneChan)
-			err := inv.Run()
-			assert.NoError(t, err)
-		}()
+				// Then create the copy.  It should use the old template version.
+				inv, root := clitest.New(t, "create", "--copy-parameters-from", tctx.workspaceName, "other-workspace", "-y")
+				clitest.SetupConfig(t, tctx.member, root)
+				pty := ptytest.New(t).Attach(inv)
+				inv.Stdout = pty.Output()
+				inv.Stderr = pty.Output()
+				err := inv.Run()
+				require.NoError(t, err, "failed to create a workspace based on the source workspace")
+				return "other-workspace"
+			},
+		},
+		{
+			name: "ValuesFromTemplateDefaults",
+			handlePty: func(pty *ptytest.PTY) {
+				// Simply accept the defaults.
+				for _, param := range params {
+					pty.ExpectMatch(param.name)
+					pty.ExpectMatch(`Enter a value (default: "` + param.value + `")`)
+					pty.WriteLine("")
+				}
+				// Confirm the creation.
+				pty.ExpectMatch("Confirm create?")
+				pty.WriteLine("yes")
+			},
+			withDefaults: true,
+		},
+		{
+			name: "ValuesFromTemplateDefaultsNoPrompt",
+			setup: func() []string {
+				return []string{"--use-parameter-defaults"}
+			},
+			handlePty: func(pty *ptytest.PTY) {
+				// Default values should get printed.
+				for _, param := range params {
+					pty.ExpectMatch(fmt.Sprintf("%s: '%s'", param.name, param.value))
+				}
+				// No prompts, we only need to confirm.
+				pty.ExpectMatch("Confirm create?")
+				pty.WriteLine("yes")
+			},
+			withDefaults: true,
+		},
+		{
+			name: "ValuesFromDefaultFlagsNoPrompt",
+			setup: func() []string {
+				// Provide the defaults on the command line.
+				args := []string{"--use-parameter-defaults"}
+				for _, param := range params {
+					args = append(args, "--parameter-default", fmt.Sprintf("%s=%s", param.name, param.value))
+				}
+				return args
+			},
+			handlePty: func(pty *ptytest.PTY) {
+				// Default values should get printed.
+				for _, param := range params {
+					pty.ExpectMatch(fmt.Sprintf("%s: '%s'", param.name, param.value))
+				}
+				// No prompts, we only need to confirm.
+				pty.ExpectMatch("Confirm create?")
+				pty.WriteLine("yes")
+			},
+		},
+		{
+			// File and flags should override template defaults.  Additionally, if a
+			// value has no default value we should still get a prompt for it.
+			name: "ValuesFromMultipleSources",
+			setup: func() []string {
+				tempDir := t.TempDir()
+				removeTmpDirUntilSuccessAfterTest(t, tempDir)
+				parameterFile, _ := os.CreateTemp(tempDir, "testParameterFile*.yaml")
+				_, err := parameterFile.WriteString(`
+file_param: from file
+cli_param: from file`)
+				require.NoError(t, err)
+				return []string{
+					"--use-parameter-defaults",
+					"--rich-parameter-file", parameterFile.Name(),
+					"--parameter-default", "file_param=from cli default",
+					"--parameter-default", "cli_param=from cli default",
+					"--parameter", "cli_param=from cli",
+				}
+			},
+			handlePty: func(pty *ptytest.PTY) {
+				// Should get prompted for the input param since it has no default.
+				pty.ExpectMatch("input_param")
+				pty.WriteLine("from input")

-		matches := []string{
-			firstParameterDescription, firstParameterValue,
-			secondParameterDisplayName, "",
-			secondParameterDescription, secondParameterValue,
-			immutableParameterDescription, immutableParameterValue,
-			"Confirm create?", "yes",
-		}
-		for i := 0; i < len(matches); i += 2 {
-			match := matches[i]
-			value := matches[i+1]
-			pty.ExpectMatch(match)
+				// Confirm the creation.
+				pty.ExpectMatch("Confirm create?")
+				pty.WriteLine("yes")
+			},
+			withDefaults: true,
+			inputParameters: []param{
+				{
+					name:  "template_param",
+					value: "from template default",
+				},
+				{
+					name:  "file_param",
+					value: "from template default",
+				},
+				{
+					name:  "cli_param",
+					value: "from template default",
+				},
+				{
+					name: "input_param",
+				},
+			},
+			expectedParameters: []param{
+				{
+					name:  "template_param",
+					value: "from template default",
+				},
+				{
+					name:  "file_param",
+					value: "from file",
+				},
+				{
+					name:  "cli_param",
+					value: "from cli",
+				},
+				{
+					name:  "input_param",
+					value: "from input",
+				},
+			},
+		},
+	}

-			if value != "" {
-				pty.WriteLine(value)
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			t.Parallel()
+
+			parameters := params
+			if len(tt.inputParameters) > 0 {
+				parameters = tt.inputParameters
 			}
-		}
-		<-doneChan
-	})

-	t.Run("ParametersDefaults", func(t *testing.T) {
-		t.Parallel()
+			// Convert parameters for the echo provisioner response.
+			var rparams []*proto.RichParameter
+			for i, param := range parameters {
+				defaultValue := ""
+				if tt.withDefaults {
+					defaultValue = param.value
+				}
+				rparams = append(rparams, &proto.RichParameter{
+					Name:         param.name,
+					Type:         param.ptype,
+					Mutable:      param.mutable,
+					DefaultValue: defaultValue,
+					Order:        int32(i), //nolint:gosec
+				})
+			}

-		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
-		owner := coderdtest.CreateFirstUser(t, client)
-		member, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
-		version := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, echoResponses())
-		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
+			// Set up the template.
+			client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
+			owner := coderdtest.CreateFirstUser(t, client)
+			member, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
+			version := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, prepareEchoResponses(rparams))

-		template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
+			coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
+			template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)

-		inv, root := clitest.New(t, "create", "my-workspace", "--template", template.Name,
-			"--parameter-default", fmt.Sprintf("%s=%s", firstParameterName, firstParameterValue),
-			"--parameter-default", fmt.Sprintf("%s=%s", secondParameterName, secondParameterValue),
-			"--parameter-default", fmt.Sprintf("%s=%s", immutableParameterName, immutableParameterValue))
-		clitest.SetupConfig(t, member, root)
-		doneChan := make(chan struct{})
-		pty := ptytest.New(t).Attach(inv)
-		go func() {
-			defer close(doneChan)
-			err := inv.Run()
-			assert.NoError(t, err)
-		}()
+			// Run the command, possibly setting up values.
+			workspaceName := "my-workspace"
+			args := []string{"create", workspaceName, "--template", template.Name}
+			if tt.setup != nil {
+				args = append(args, tt.setup()...)
+			}
+			inv, root := clitest.New(t, args...)
+			clitest.SetupConfig(t, member, root)
+			doneChan := make(chan error)
+			pty := ptytest.New(t).Attach(inv)
+			go func() {
+				doneChan <- inv.Run()
+			}()

-		matches := []string{
-			firstParameterDescription, firstParameterValue,
-			secondParameterDescription, secondParameterValue,
-			immutableParameterDescription, immutableParameterValue,
-		}
-		for i := 0; i < len(matches); i += 2 {
-			match := matches[i]
-			defaultValue := matches[i+1]
+			// The test may do something with the pty.
+			if tt.handlePty != nil {
+				tt.handlePty(pty)
+			}

-			pty.ExpectMatch(match)
-			pty.ExpectMatch(`Enter a value (default: "` + defaultValue + `")`)
-			pty.WriteLine("")
-		}
-		pty.ExpectMatch("Confirm create?")
-		pty.WriteLine("yes")
-		<-doneChan
+			// Wait for the command to exit.
+			err := <-doneChan

-		// Verify that the expected default values were used.
-		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
-		defer cancel()
+			// The test may want to run additional setup like copying the workspace.
+			if tt.postRun != nil {
+				workspaceName = tt.postRun(t, testContext{
+					client:        client,
+					member:        member,
+					owner:         owner,
+					template:      template,
+					workspaceName: workspaceName,
+				})
+			}

-		workspaces, err := client.Workspaces(ctx, codersdk.WorkspaceFilter{
-			Name: "my-workspace",
+			if len(tt.errors) > 0 {
+				require.Error(t, err)
+				for _, errstr := range tt.errors {
+					assert.ErrorContains(t, err, errstr)
+				}
+			} else {
+				require.NoError(t, err)
+
+				// Verify the workspace was created and has the right template and values.
+				ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
+				defer cancel()
+
+				workspaces, err := client.Workspaces(ctx, codersdk.WorkspaceFilter{Name: workspaceName})
+				require.NoError(t, err, "expected to find created workspace")
+				require.Len(t, workspaces.Workspaces, 1)
+
+				workspaceLatestBuild := workspaces.Workspaces[0].LatestBuild
+				require.Equal(t, version.ID, workspaceLatestBuild.TemplateVersionID)
+
+				buildParameters, err := client.WorkspaceBuildParameters(ctx, workspaceLatestBuild.ID)
+				require.NoError(t, err)
+				if len(tt.expectedParameters) > 0 {
+					parameters = tt.expectedParameters
+				}
+				require.Len(t, buildParameters, len(parameters))
+				for _, param := range parameters {
+					require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: param.name, Value: param.value})
+				}
+			}
 		})
-		require.NoError(t, err, "can't list available workspaces")
-		require.Len(t, workspaces.Workspaces, 1)
-
-		workspaceLatestBuild := workspaces.Workspaces[0].LatestBuild
-		require.Equal(t, version.ID, workspaceLatestBuild.TemplateVersionID)
-
-		buildParameters, err := client.WorkspaceBuildParameters(ctx, workspaceLatestBuild.ID)
-		require.NoError(t, err)
-		require.Len(t, buildParameters, 3)
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: firstParameterName, Value: firstParameterValue})
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: secondParameterName, Value: secondParameterValue})
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: immutableParameterName, Value: immutableParameterValue})
-	})
-
-	t.Run("RichParametersFile", func(t *testing.T) {
-		t.Parallel()
-
-		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
-		owner := coderdtest.CreateFirstUser(t, client)
-		member, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
-		version := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, echoResponses())
-		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
-
-		template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
-
-		tempDir := t.TempDir()
-		removeTmpDirUntilSuccessAfterTest(t, tempDir)
-		parameterFile, _ := os.CreateTemp(tempDir, "testParameterFile*.yaml")
-		_, _ = parameterFile.WriteString(
-			firstParameterName + ": " + firstParameterValue + "\n" +
-				secondParameterName + ": " + secondParameterValue + "\n" +
-				immutableParameterName + ": " + immutableParameterValue)
-		inv, root := clitest.New(t, "create", "my-workspace", "--template", template.Name, "--rich-parameter-file", parameterFile.Name())
-		clitest.SetupConfig(t, member, root)
-
-		doneChan := make(chan struct{})
-		pty := ptytest.New(t).Attach(inv)
-		go func() {
-			defer close(doneChan)
-			err := inv.Run()
-			assert.NoError(t, err)
-		}()
-
-		matches := []string{
-			"Confirm create?", "yes",
-		}
-		for i := 0; i < len(matches); i += 2 {
-			match := matches[i]
-			value := matches[i+1]
-			pty.ExpectMatch(match)
-			pty.WriteLine(value)
-		}
-		<-doneChan
-	})
-
-	t.Run("ParameterFlags", func(t *testing.T) {
-		t.Parallel()
-
-		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
-		owner := coderdtest.CreateFirstUser(t, client)
-		member, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
-		version := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, echoResponses())
-		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
-
-		template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
-
-		inv, root := clitest.New(t, "create", "my-workspace", "--template", template.Name,
-			"--parameter", fmt.Sprintf("%s=%s", firstParameterName, firstParameterValue),
-			"--parameter", fmt.Sprintf("%s=%s", secondParameterName, secondParameterValue),
-			"--parameter", fmt.Sprintf("%s=%s", immutableParameterName, immutableParameterValue))
-		clitest.SetupConfig(t, member, root)
-		doneChan := make(chan struct{})
-		pty := ptytest.New(t).Attach(inv)
-		go func() {
-			defer close(doneChan)
-			err := inv.Run()
-			assert.NoError(t, err)
-		}()
-
-		matches := []string{
-			"Confirm create?", "yes",
-		}
-		for i := 0; i < len(matches); i += 2 {
-			match := matches[i]
-			value := matches[i+1]
-			pty.ExpectMatch(match)
-			pty.WriteLine(value)
-		}
-		<-doneChan
-	})
-
-	t.Run("WrongParameterName/DidYouMean", func(t *testing.T) {
-		t.Parallel()
-
-		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
-		owner := coderdtest.CreateFirstUser(t, client)
-		member, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
-		version := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, echoResponses())
-		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
-
-		template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
-
-		wrongFirstParameterName := "frst-prameter"
-		inv, root := clitest.New(t, "create", "my-workspace", "--template", template.Name,
-			"--parameter", fmt.Sprintf("%s=%s", wrongFirstParameterName, firstParameterValue),
-			"--parameter", fmt.Sprintf("%s=%s", secondParameterName, secondParameterValue),
-			"--parameter", fmt.Sprintf("%s=%s", immutableParameterName, immutableParameterValue))
-		clitest.SetupConfig(t, member, root)
-		pty := ptytest.New(t).Attach(inv)
-		inv.Stdout = pty.Output()
-		inv.Stderr = pty.Output()
-		err := inv.Run()
-		assert.ErrorContains(t, err, "parameter \""+wrongFirstParameterName+"\" is not present in the template")
-		assert.ErrorContains(t, err, "Did you mean: "+firstParameterName)
-	})
-
-	t.Run("CopyParameters", func(t *testing.T) {
-		t.Parallel()
-
-		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
-		owner := coderdtest.CreateFirstUser(t, client)
-		member, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
-		version := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, echoResponses())
-		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
-
-		template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
-
-		// Firstly, create a regular workspace using template with parameters.
-		inv, root := clitest.New(t, "create", "my-workspace", "--template", template.Name, "-y",
-			"--parameter", fmt.Sprintf("%s=%s", firstParameterName, firstParameterValue),
-			"--parameter", fmt.Sprintf("%s=%s", secondParameterName, secondParameterValue),
-			"--parameter", fmt.Sprintf("%s=%s", immutableParameterName, immutableParameterValue))
-		clitest.SetupConfig(t, member, root)
-		pty := ptytest.New(t).Attach(inv)
-		inv.Stdout = pty.Output()
-		inv.Stderr = pty.Output()
-		err := inv.Run()
-		require.NoError(t, err, "can't create first workspace")
-
-		// Secondly, create a new workspace using parameters from the previous workspace.
-		const otherWorkspace = "other-workspace"
-
-		inv, root = clitest.New(t, "create", "--copy-parameters-from", "my-workspace", otherWorkspace, "-y")
-		clitest.SetupConfig(t, member, root)
-		pty = ptytest.New(t).Attach(inv)
-		inv.Stdout = pty.Output()
-		inv.Stderr = pty.Output()
-		err = inv.Run()
-		require.NoError(t, err, "can't create a workspace based on the source workspace")
-
-		// Verify if the new workspace uses expected parameters.
-		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
-		defer cancel()
-
-		workspaces, err := client.Workspaces(ctx, codersdk.WorkspaceFilter{
-			Name: otherWorkspace,
-		})
-		require.NoError(t, err, "can't list available workspaces")
-		require.Len(t, workspaces.Workspaces, 1)
-
-		otherWorkspaceLatestBuild := workspaces.Workspaces[0].LatestBuild
-
-		buildParameters, err := client.WorkspaceBuildParameters(ctx, otherWorkspaceLatestBuild.ID)
-		require.NoError(t, err)
-		require.Len(t, buildParameters, 3)
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: firstParameterName, Value: firstParameterValue})
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: secondParameterName, Value: secondParameterValue})
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: immutableParameterName, Value: immutableParameterValue})
-	})
-
-	t.Run("CopyParametersFromNotUpdatedWorkspace", func(t *testing.T) {
-		t.Parallel()
-
-		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
-		owner := coderdtest.CreateFirstUser(t, client)
-		member, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
-		version := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, echoResponses())
-		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
-
-		template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
-
-		// Firstly, create a regular workspace using template with parameters.
-		inv, root := clitest.New(t, "create", "my-workspace", "--template", template.Name, "-y",
-			"--parameter", fmt.Sprintf("%s=%s", firstParameterName, firstParameterValue),
-			"--parameter", fmt.Sprintf("%s=%s", secondParameterName, secondParameterValue),
-			"--parameter", fmt.Sprintf("%s=%s", immutableParameterName, immutableParameterValue))
-		clitest.SetupConfig(t, member, root)
-		pty := ptytest.New(t).Attach(inv)
-		inv.Stdout = pty.Output()
-		inv.Stderr = pty.Output()
-		err := inv.Run()
-		require.NoError(t, err, "can't create first workspace")
-
-		// Secondly, update the template to the newer version.
-		version2 := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, prepareEchoResponses([]*proto.RichParameter{
-			{Name: "third_parameter", Type: "string", DefaultValue: "not-relevant"},
-		}), func(ctvr *codersdk.CreateTemplateVersionRequest) {
-			ctvr.TemplateID = template.ID
-		})
-		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version2.ID)
-		coderdtest.UpdateActiveTemplateVersion(t, client, template.ID, version2.ID)
-
-		// Thirdly, create a new workspace using parameters from the previous workspace.
-		const otherWorkspace = "other-workspace"
-
-		inv, root = clitest.New(t, "create", "--copy-parameters-from", "my-workspace", otherWorkspace, "-y")
-		clitest.SetupConfig(t, member, root)
-		pty = ptytest.New(t).Attach(inv)
-		inv.Stdout = pty.Output()
-		inv.Stderr = pty.Output()
-		err = inv.Run()
-		require.NoError(t, err, "can't create a workspace based on the source workspace")
-
-		// Verify if the new workspace uses expected parameters.
-		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
-		defer cancel()
-
-		workspaces, err := client.Workspaces(ctx, codersdk.WorkspaceFilter{
-			Name: otherWorkspace,
-		})
-		require.NoError(t, err, "can't list available workspaces")
-		require.Len(t, workspaces.Workspaces, 1)
-
-		otherWorkspaceLatestBuild := workspaces.Workspaces[0].LatestBuild
-		require.Equal(t, version.ID, otherWorkspaceLatestBuild.TemplateVersionID)
-
-		buildParameters, err := client.WorkspaceBuildParameters(ctx, otherWorkspaceLatestBuild.ID)
-		require.NoError(t, err)
-		require.Len(t, buildParameters, 3)
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: firstParameterName, Value: firstParameterValue})
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: secondParameterName, Value: secondParameterValue})
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: immutableParameterName, Value: immutableParameterValue})
-	})
+	}
 }

 func TestCreateWithPreset(t *testing.T) {
@@ -1,12 +0,0 @@
-package cli
-
-import (
-	boundarycli "github.com/coder/boundary/cli"
-	"github.com/coder/serpent"
-)
-
-func (*RootCmd) boundary() *serpent.Command {
-	cmd := boundarycli.BaseCommand() // Package coder/boundary/cli exports a "base command" designed to be integrated as a subcommand.
-	cmd.Use += " [args...]"          // The base command looks like `boundary -- command`. Serpent adds the flags piece, but we need to add the args.
-	return cmd
-}
@@ -1,33 +0,0 @@
-package cli_test
-
-import (
-	"testing"
-
-	"github.com/stretchr/testify/assert"
-
-	boundarycli "github.com/coder/boundary/cli"
-	"github.com/coder/coder/v2/cli/clitest"
-	"github.com/coder/coder/v2/pty/ptytest"
-	"github.com/coder/coder/v2/testutil"
-)
-
-// Actually testing the functionality of coder/boundary takes place in the
-// coder/boundary repo, since it's a dependency of coder.
-// Here we want to test basically that integrating it as a subcommand doesn't break anything.
-func TestBoundarySubcommand(t *testing.T) {
-	t.Parallel()
-	ctx := testutil.Context(t, testutil.WaitShort)
-
-	inv, _ := clitest.New(t, "exp", "boundary", "--help")
-	pty := ptytest.New(t).Attach(inv)
-
-	go func() {
-		err := inv.WithContext(ctx).Run()
-		assert.NoError(t, err)
-	}()
-
-	// Expect the --help output to include the short description.
-	// We're simply confirming that `coder boundary --help` ran without a runtime error as
-	// a good chunk of serpents self validation logic happens at runtime.
-	pty.ExpectMatch(boundarycli.BaseCommand().Short)
-}
@@ -68,6 +68,8 @@ func (r *RootCmd) scaletestCmd() *serpent.Command {
 			r.scaletestTaskStatus(),
 			r.scaletestSMTP(),
 			r.scaletestPrebuilds(),
+			r.scaletestBridge(),
+			r.scaletestLLMMock(),
 		},
 	}

@@ -0,0 +1,281 @@
+//go:build !slim
+
+package cli
+
+import (
+	"fmt"
+	"net/http"
+	"os/signal"
+	"strconv"
+	"text/tabwriter"
+	"time"
+
+	"github.com/prometheus/client_golang/prometheus"
+	"github.com/prometheus/client_golang/prometheus/promhttp"
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/codersdk"
+	"github.com/coder/coder/v2/scaletest/bridge"
+	"github.com/coder/coder/v2/scaletest/createusers"
+	"github.com/coder/coder/v2/scaletest/harness"
+	"github.com/coder/serpent"
+)
+
+func (r *RootCmd) scaletestBridge() *serpent.Command {
+	var (
+		concurrentUsers    int64
+		noCleanup          bool
+		mode               string
+		upstreamURL        string
+		provider           string
+		requestsPerUser    int64
+		useStreamingAPI    bool
+		requestPayloadSize int64
+		numMessages        int64
+		httpTimeout        time.Duration
+
+		timeoutStrategy = &timeoutFlags{}
+		cleanupStrategy = newScaletestCleanupStrategy()
+		output          = &scaletestOutputFlags{}
+		prometheusFlags = &scaletestPrometheusFlags{}
+	)
+
+	cmd := &serpent.Command{
+		Use:   "bridge",
+		Short: "Generate load on the AI Bridge service.",
+		Long: `Generate load for AI Bridge testing. Supports two modes: 'bridge' mode routes requests through the Coder AI Bridge, 'direct' mode makes requests directly to an upstream URL (useful for baseline comparisons).
+
+Examples:
+  # Test OpenAI API through bridge
+  coder scaletest bridge --mode bridge --provider openai --concurrent-users 10 --request-count 5 --num-messages 10
+
+  # Test OpenAI Responses API through bridge
+  coder scaletest bridge --mode bridge --provider responses --concurrent-users 10 --request-count 5 --num-messages 10
+
+  # Test Anthropic API through bridge
+  coder scaletest bridge --mode bridge --provider anthropic --concurrent-users 10 --request-count 5 --num-messages 10
+
+  # Test directly against mock server
+  coder scaletest bridge --mode direct --provider openai --upstream-url http://localhost:8080/v1/chat/completions
+`,
+		Handler: func(inv *serpent.Invocation) error {
+			ctx := inv.Context()
+			client, err := r.InitClient(inv)
+			if err != nil {
+				return err
+			}
+			client.HTTPClient = &http.Client{
+				Transport: &codersdk.HeaderTransport{
+					Transport: http.DefaultTransport,
+					Header: map[string][]string{
+						codersdk.BypassRatelimitHeader: {"true"},
+					},
+				},
+			}
+			reg := prometheus.NewRegistry()
+			metrics := bridge.NewMetrics(reg)
+
+			logger := inv.Logger
+			prometheusSrvClose := ServeHandler(ctx, logger, promhttp.HandlerFor(reg, promhttp.HandlerOpts{}), prometheusFlags.Address, "prometheus")
+			defer prometheusSrvClose()
+
+			defer func() {
+				_, _ = fmt.Fprintf(inv.Stderr, "Waiting %s for prometheus metrics to be scraped\n", prometheusFlags.Wait)
+				<-time.After(prometheusFlags.Wait)
+			}()
+
+			notifyCtx, stop := signal.NotifyContext(ctx, StopSignals...)
+			defer stop()
+			ctx = notifyCtx
+
+			var userConfig createusers.Config
+			if bridge.RequestMode(mode) == bridge.RequestModeBridge {
+				me, err := requireAdmin(ctx, client)
+				if err != nil {
+					return err
+				}
+				if len(me.OrganizationIDs) == 0 {
+					return xerrors.Errorf("admin user must have at least one organization")
+				}
+				userConfig = createusers.Config{
+					OrganizationID: me.OrganizationIDs[0],
+				}
+				_, _ = fmt.Fprintln(inv.Stderr, "Bridge mode: creating users and making requests through AI Bridge...")
+			} else {
+				_, _ = fmt.Fprintf(inv.Stderr, "Direct mode: making requests directly to %s\n", upstreamURL)
+			}
+
+			outputs, err := output.parse()
+			if err != nil {
+				return xerrors.Errorf("parse output flags: %w", err)
+			}
+
+			config := bridge.Config{
+				Mode:               bridge.RequestMode(mode),
+				Metrics:            metrics,
+				Provider:           provider,
+				RequestCount:       int(requestsPerUser),
+				Stream:             useStreamingAPI,
+				RequestPayloadSize: int(requestPayloadSize),
+				NumMessages:        int(numMessages),
+				HTTPTimeout:        httpTimeout,
+				UpstreamURL:        upstreamURL,
+				User:               userConfig,
+			}
+			if err := config.Validate(); err != nil {
+				return xerrors.Errorf("validate config: %w", err)
+			}
+			if err := config.PrepareRequestBody(); err != nil {
+				return xerrors.Errorf("prepare request body: %w", err)
+			}
+
+			th := harness.NewTestHarness(timeoutStrategy.wrapStrategy(harness.ConcurrentExecutionStrategy{}), cleanupStrategy.toStrategy())
+
+			for i := range concurrentUsers {
+				id := strconv.Itoa(int(i))
+				name := fmt.Sprintf("bridge-%s", id)
+				var runner harness.Runnable = bridge.NewRunner(client, config)
+				th.AddRun(name, id, runner)
+			}
+
+			_, _ = fmt.Fprintln(inv.Stderr, "Bridge scaletest configuration:")
+			tw := tabwriter.NewWriter(inv.Stderr, 0, 0, 2, ' ', 0)
+			for _, opt := range inv.Command.Options {
+				if opt.Hidden || opt.ValueSource == serpent.ValueSourceNone {
+					continue
+				}
+				_, _ = fmt.Fprintf(tw, "  %s:\t%s", opt.Name, opt.Value.String())
+				if opt.ValueSource != serpent.ValueSourceDefault {
+					_, _ = fmt.Fprintf(tw, "\t(from %s)", opt.ValueSource)
+				}
+				_, _ = fmt.Fprintln(tw)
+			}
+			_ = tw.Flush()
+
+			_, _ = fmt.Fprintln(inv.Stderr, "\nRunning bridge scaletest...")
+			testCtx, testCancel := timeoutStrategy.toContext(ctx)
+			defer testCancel()
+			err = th.Run(testCtx)
+			if err != nil {
+				return xerrors.Errorf("run test harness (harness failure, not a test failure): %w", err)
+			}
+
+			// If the command was interrupted, skip stats.
+			if notifyCtx.Err() != nil {
+				return notifyCtx.Err()
+			}
+
+			res := th.Results()
+
+			for _, o := range outputs {
+				err = o.write(res, inv.Stdout)
+				if err != nil {
+					return xerrors.Errorf("write output %q to %q: %w", o.format, o.path, err)
+				}
+			}
+
+			if !noCleanup {
+				_, _ = fmt.Fprintln(inv.Stderr, "\nCleaning up...")
+				cleanupCtx, cleanupCancel := cleanupStrategy.toContext(ctx)
+				defer cleanupCancel()
+				err = th.Cleanup(cleanupCtx)
+				if err != nil {
+					return xerrors.Errorf("cleanup tests: %w", err)
+				}
+			}
+
+			if res.TotalFail > 0 {
+				return xerrors.New("load test failed, see above for more details")
+			}
+
+			return nil
+		},
+	}
+
+	cmd.Options = serpent.OptionSet{
+		{
+			Flag:          "concurrent-users",
+			FlagShorthand: "c",
+			Env:           "CODER_SCALETEST_BRIDGE_CONCURRENT_USERS",
+			Description:   "Required: Number of concurrent users.",
+			Value: serpent.Validate(serpent.Int64Of(&concurrentUsers), func(value *serpent.Int64) error {
+				if value == nil || value.Value() <= 0 {
+					return xerrors.Errorf("--concurrent-users must be greater than 0")
+				}
+				return nil
+			}),
+			Required: true,
+		},
+		{
+			Flag:        "mode",
+			Env:         "CODER_SCALETEST_BRIDGE_MODE",
+			Default:     "direct",
+			Description: "Request mode: 'bridge' (create users and use AI Bridge) or 'direct' (make requests directly to upstream-url).",
+			Value:       serpent.EnumOf(&mode, string(bridge.RequestModeBridge), string(bridge.RequestModeDirect)),
+		},
+		{
+			Flag:        "upstream-url",
+			Env:         "CODER_SCALETEST_BRIDGE_UPSTREAM_URL",
+			Description: "URL to make requests to directly (required in direct mode, e.g., http://localhost:8080/v1/chat/completions).",
+			Value:       serpent.StringOf(&upstreamURL),
+		},
+		{
+			Flag:        "provider",
+			Env:         "CODER_SCALETEST_BRIDGE_PROVIDER",
+			Required:    true,
+			Description: "API provider to use.",
+			Value:       serpent.EnumOf(&provider, "completions", "messages", "responses"),
+		},
+		{
+			Flag:        "request-count",
+			Env:         "CODER_SCALETEST_BRIDGE_REQUEST_COUNT",
+			Default:     "1",
+			Description: "Number of sequential requests to make per runner.",
+			Value: serpent.Validate(serpent.Int64Of(&requestsPerUser), func(value *serpent.Int64) error {
+				if value == nil || value.Value() <= 0 {
+					return xerrors.Errorf("--request-count must be greater than 0")
+				}
+				return nil
+			}),
+		},
+		{
+			Flag:        "stream",
+			Env:         "CODER_SCALETEST_BRIDGE_STREAM",
+			Description: "Enable streaming requests.",
+			Value:       serpent.BoolOf(&useStreamingAPI),
+		},
+		{
+			Flag:        "request-payload-size",
+			Env:         "CODER_SCALETEST_BRIDGE_REQUEST_PAYLOAD_SIZE",
+			Default:     "1024",
+			Description: "Size in bytes of the request payload (user message content). If 0, uses default message content.",
+			Value:       serpent.Int64Of(&requestPayloadSize),
+		},
+		{
+			Flag:        "num-messages",
+			Env:         "CODER_SCALETEST_BRIDGE_NUM_MESSAGES",
+			Default:     "1",
+			Description: "Number of messages to include in the conversation.",
+			Value:       serpent.Int64Of(&numMessages),
+		},
+		{
+			Flag:        "no-cleanup",
+			Env:         "CODER_SCALETEST_NO_CLEANUP",
+			Description: "Do not clean up resources after the test completes.",
+			Value:       serpent.BoolOf(&noCleanup),
+		},
+		{
+			Flag:        "http-timeout",
+			Env:         "CODER_SCALETEST_BRIDGE_HTTP_TIMEOUT",
+			Default:     "30s",
+			Description: "Timeout for individual HTTP requests to the upstream provider.",
+			Value:       serpent.DurationOf(&httpTimeout),
+		},
+	}
+
+	timeoutStrategy.attach(&cmd.Options)
+	cleanupStrategy.attach(&cmd.Options)
+	output.attach(&cmd.Options)
+	prometheusFlags.attach(&cmd.Options)
+	return cmd
+}
@@ -0,0 +1,119 @@
+//go:build !slim
+
+package cli
+
+import (
+	"fmt"
+	"os/signal"
+	"time"
+
+	"golang.org/x/xerrors"
+
+	"cdr.dev/slog/v3"
+	"cdr.dev/slog/v3/sloggers/sloghuman"
+	"github.com/coder/coder/v2/scaletest/llmmock"
+	"github.com/coder/serpent"
+)
+
+func (*RootCmd) scaletestLLMMock() *serpent.Command {
+	var (
+		address             string
+		artificialLatency   time.Duration
+		responsePayloadSize int64
+
+		pprofEnable  bool
+		pprofAddress string
+
+		traceEnable bool
+	)
+	cmd := &serpent.Command{
+		Use:   "llm-mock",
+		Short: "Start a mock LLM API server for testing",
+		Long:  `Start a mock LLM API server that simulates OpenAI and Anthropic APIs`,
+		Handler: func(inv *serpent.Invocation) error {
+			ctx, stop := signal.NotifyContext(inv.Context(), StopSignals...)
+			defer stop()
+
+			logger := slog.Make(sloghuman.Sink(inv.Stderr)).Leveled(slog.LevelInfo)
+
+			if pprofEnable {
+				closePprof := ServeHandler(ctx, logger, nil, pprofAddress, "pprof")
+				defer closePprof()
+				logger.Info(ctx, "pprof server started", slog.F("address", pprofAddress))
+			}
+
+			config := llmmock.Config{
+				Address:             address,
+				Logger:              logger,
+				ArtificialLatency:   artificialLatency,
+				ResponsePayloadSize: int(responsePayloadSize),
+				PprofEnable:         pprofEnable,
+				PprofAddress:        pprofAddress,
+				TraceEnable:         traceEnable,
+			}
+			srv := new(llmmock.Server)
+
+			if err := srv.Start(ctx, config); err != nil {
+				return xerrors.Errorf("start mock LLM server: %w", err)
+			}
+			defer func() {
+				_ = srv.Stop()
+			}()
+
+			_, _ = fmt.Fprintf(inv.Stdout, "Mock LLM API server started on %s\n", srv.APIAddress())
+			_, _ = fmt.Fprintf(inv.Stdout, "  OpenAI endpoint: %s/v1/chat/completions\n", srv.APIAddress())
+			_, _ = fmt.Fprintf(inv.Stdout, "  OpenAI responses endpoint: %s/v1/responses\n", srv.APIAddress())
+			_, _ = fmt.Fprintf(inv.Stdout, "  Anthropic endpoint: %s/v1/messages\n", srv.APIAddress())
+
+			<-ctx.Done()
+			return nil
+		},
+	}
+
+	cmd.Options = []serpent.Option{
+		{
+			Flag:        "address",
+			Env:         "CODER_SCALETEST_LLM_MOCK_ADDRESS",
+			Default:     "localhost",
+			Description: "Address to bind the mock LLM API server. Can include a port (e.g., 'localhost:8080' or ':8080'). Uses a random port if no port is specified.",
+			Value:       serpent.StringOf(&address),
+		},
+		{
+			Flag:        "artificial-latency",
+			Env:         "CODER_SCALETEST_LLM_MOCK_ARTIFICIAL_LATENCY",
+			Default:     "0s",
+			Description: "Artificial latency to add to each response (e.g., 100ms, 1s). Simulates slow upstream processing.",
+			Value:       serpent.DurationOf(&artificialLatency),
+		},
+		{
+			Flag:        "response-payload-size",
+			Env:         "CODER_SCALETEST_LLM_MOCK_RESPONSE_PAYLOAD_SIZE",
+			Default:     "0",
+			Description: "Size in bytes of the response payload. If 0, uses default context-aware responses.",
+			Value:       serpent.Int64Of(&responsePayloadSize),
+		},
+		{
+			Flag:        "pprof-enable",
+			Env:         "CODER_SCALETEST_LLM_MOCK_PPROF_ENABLE",
+			Default:     "false",
+			Description: "Serve pprof metrics on the address defined by pprof-address.",
+			Value:       serpent.BoolOf(&pprofEnable),
+		},
+		{
+			Flag:        "pprof-address",
+			Env:         "CODER_SCALETEST_LLM_MOCK_PPROF_ADDRESS",
+			Default:     "127.0.0.1:6060",
+			Description: "The bind address to serve pprof.",
+			Value:       serpent.StringOf(&pprofAddress),
+		},
+		{
+			Flag:        "trace-enable",
+			Env:         "CODER_SCALETEST_LLM_MOCK_TRACE_ENABLE",
+			Default:     "false",
+			Description: "Whether application tracing data is collected. It exports to a backend configured by environment variables. See: https://github.com/open-telemetry/opentelemetry-specification/blob/main/specification/protocol/exporter.md.",
+			Value:       serpent.BoolOf(&traceEnable),
+		},
+	}
+
+	return cmd
+}
@@ -65,6 +65,22 @@ func (r *RootCmd) organizationSettings(orgContext *OrganizationContext) *serpent
 				return cli.OrganizationIDPSyncSettings(ctx)
 			},
 		},
+		{
+			Name:    "workspace-sharing",
+			Aliases: []string{"workspacesharing"},
+			Short:   "Workspace sharing settings for the organization.",
+			Patch: func(ctx context.Context, cli *codersdk.Client, org uuid.UUID, input json.RawMessage) (any, error) {
+				var req codersdk.WorkspaceSharingSettings
+				err := json.Unmarshal(input, &req)
+				if err != nil {
+					return nil, xerrors.Errorf("unmarshalling workspace sharing settings: %w", err)
+				}
+				return cli.PatchWorkspaceSharingSettings(ctx, org.String(), req)
+			},
+			Fetch: func(ctx context.Context, cli *codersdk.Client, org uuid.UUID) (any, error) {
+				return cli.WorkspaceSharingSettings(ctx, org.String())
+			},
+		},
 	}
 	cmd := &serpent.Command{
 		Use:     "settings",
@@ -34,6 +34,7 @@ type ParameterResolver struct {

 	promptRichParameters      bool
 	promptEphemeralParameters bool
+	useParameterDefaults      bool
 }

 func (pr *ParameterResolver) WithLastBuildParameters(params []codersdk.WorkspaceBuildParameter) *ParameterResolver {
@@ -86,8 +87,21 @@ func (pr *ParameterResolver) WithPromptEphemeralParameters(promptEphemeralParame
 	return pr
 }

-// Resolve gathers workspace build parameters in a layered fashion, applying values from various sources
-// in order of precedence: parameter file < CLI/ENV < source build < last build < preset < user input.
+func (pr *ParameterResolver) WithUseParameterDefaults(useParameterDefaults bool) *ParameterResolver {
+	pr.useParameterDefaults = useParameterDefaults
+	return pr
+}
+
+// Resolve gathers workspace build parameters in a layered fashion, applying
+// values from various sources in order of precedence:
+// 1. template defaults (if auto-accepting defaults)
+// 2. cli parameter defaults (if auto-accepting defaults)
+// 3. parameter file
+// 4. CLI/ENV
+// 5. source build
+// 6. last build
+// 7. preset
+// 8. user input (unless auto-accepting defaults)
 func (pr *ParameterResolver) Resolve(inv *serpent.Invocation, action WorkspaceCLIAction, templateVersionParameters []codersdk.TemplateVersionParameter) ([]codersdk.WorkspaceBuildParameter, error) {
 	var staged []codersdk.WorkspaceBuildParameter
 	var err error
@@ -262,9 +276,25 @@ func (pr *ParameterResolver) resolveWithInput(resolved []codersdk.WorkspaceBuild
 			(action == WorkspaceUpdate && tvp.Mutable && tvp.Required) ||
 			(action == WorkspaceUpdate && !tvp.Mutable && firstTimeUse) ||
 			(tvp.Mutable && !tvp.Ephemeral && pr.promptRichParameters) {
-			parameterValue, err := cliui.RichParameter(inv, tvp, pr.richParametersDefaults)
-			if err != nil {
-				return nil, err
+			name := tvp.Name
+			if tvp.DisplayName != "" {
+				name = tvp.DisplayName
+			}
+
+			parameterValue := tvp.DefaultValue
+			if v, ok := pr.richParametersDefaults[tvp.Name]; ok {
+				parameterValue = v
+			}
+
+			// Auto-accept the default if there is one.
+			if pr.useParameterDefaults && parameterValue != "" {
+				_, _ = fmt.Fprintf(inv.Stdout, "Using default value for %s: '%s'\n", name, parameterValue)
+			} else {
+				var err error
+				parameterValue, err = cliui.RichParameter(inv, tvp, name, parameterValue)
+				if err != nil {
+					return nil, err
+				}
 			}

 			resolved = append(resolved, codersdk.WorkspaceBuildParameter{
@@ -24,6 +24,7 @@ import (
 	"text/tabwriter"
 	"time"

+	"github.com/google/uuid"
 	"github.com/mattn/go-isatty"
 	"github.com/mitchellh/go-wordwrap"
 	"golang.org/x/mod/semver"
@@ -150,7 +151,6 @@ func (r *RootCmd) AGPLExperimental() []*serpent.Command {
 		r.promptExample(),
 		r.rptyCommand(),
 		r.syncCommand(),
-		r.boundary(),
 	}
 }

@@ -332,6 +332,12 @@ func (r *RootCmd) Command(subcommands []*serpent.Command) (*serpent.Command, err
 					// support links.
 					return
 				}
+				if cmd.Name() == "boundary" {
+					// The boundary command is integrated from the boundary package
+					// and has YAML-only options (e.g., allowlist from config file)
+					// that don't have flags or env vars.
+					return
+				}
 				merr = errors.Join(
 					merr,
 					xerrors.Errorf("option %q in %q should have a flag or env", opt.Name, cmd.FullName()),
@@ -923,6 +929,9 @@ func splitNamedWorkspace(identifier string) (owner string, workspaceName string,
 // a bare name (for a workspace owned by the current user) or a "user/workspace" combination,
 // where user is either a username or UUID.
 func namedWorkspace(ctx context.Context, client *codersdk.Client, identifier string) (codersdk.Workspace, error) {
+	if uid, err := uuid.Parse(identifier); err == nil {
+		return client.Workspace(ctx, uid)
+	}
 	owner, name, err := splitNamedWorkspace(identifier)
 	if err != nil {
 		return codersdk.Workspace{}, err
@@ -197,7 +197,7 @@ func TestSharingStatus(t *testing.T) {
 			ctx                = testutil.Context(t, testutil.WaitMedium)
 		)

-		err := workspaceOwnerClient.UpdateWorkspaceACL(ctx, workspace.ID, codersdk.UpdateWorkspaceACL{
+		err := client.UpdateWorkspaceACL(ctx, workspace.ID, codersdk.UpdateWorkspaceACL{
 			UserRoles: map[string]codersdk.WorkspaceRole{
 				toShareWithUser.ID.String(): codersdk.WorkspaceRoleUse,
 			},
@@ -248,7 +248,7 @@ func TestSharingRemove(t *testing.T) {
 		ctx := testutil.Context(t, testutil.WaitMedium)

 		// Share the workspace with a user to later remove
-		err := workspaceOwnerClient.UpdateWorkspaceACL(ctx, workspace.ID, codersdk.UpdateWorkspaceACL{
+		err := client.UpdateWorkspaceACL(ctx, workspace.ID, codersdk.UpdateWorkspaceACL{
 			UserRoles: map[string]codersdk.WorkspaceRole{
 				toShareWithUser.ID.String(): codersdk.WorkspaceRoleUse,
 				toRemoveUser.ID.String():    codersdk.WorkspaceRoleUse,
@@ -309,7 +309,7 @@ func TestSharingRemove(t *testing.T) {
 		ctx := testutil.Context(t, testutil.WaitMedium)

 		// Share the workspace with a user to later remove
-		err := workspaceOwnerClient.UpdateWorkspaceACL(ctx, workspace.ID, codersdk.UpdateWorkspaceACL{
+		err := client.UpdateWorkspaceACL(ctx, workspace.ID, codersdk.UpdateWorkspaceACL{
 			UserRoles: map[string]codersdk.WorkspaceRole{
 				toRemoveUser2.ID.String(): codersdk.WorkspaceRoleUse,
 				toRemoveUser1.ID.String(): codersdk.WorkspaceRoleUse,
@@ -1,8 +1,10 @@
 package cli

 import (
+	"fmt"
 	"sort"
 	"sync"
+	"time"

 	"github.com/google/uuid"
 	"golang.org/x/xerrors"
@@ -43,11 +45,11 @@ func (r *RootCmd) show() *serpent.Command {
 			if err != nil {
 				return xerrors.Errorf("get workspace: %w", err)
 			}
-
 			options := cliui.WorkspaceResourcesOptions{
 				WorkspaceName: workspace.Name,
 				ServerVersion: buildInfo.Version,
 				ShowDetails:   details,
+				Title:         fmt.Sprintf("%s/%s (%s since %s) %s:%s", workspace.OwnerName, workspace.Name, workspace.LatestBuild.Status, time.Since(workspace.LatestBuild.CreatedAt).Round(time.Second).String(), workspace.TemplateName, workspace.LatestBuild.TemplateVersionName),
 			}
 			if workspace.LatestBuild.Status == codersdk.WorkspaceStatusRunning {
 				// Get listening ports for each agent.
@@ -55,7 +57,6 @@ func (r *RootCmd) show() *serpent.Command {
 				options.ListeningPorts = ports
 				options.Devcontainers = devcontainers
 			}
-
 			return cliui.WorkspaceResources(inv.Stdout, workspace.LatestBuild.Resources, options)
 		},
 	}
@@ -2,6 +2,7 @@ package cli_test

 import (
 	"bytes"
+	"fmt"
 	"testing"
 	"time"

@@ -15,6 +16,7 @@ import (
 	"github.com/coder/coder/v2/coderd/coderdtest"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/pty/ptytest"
+	"github.com/coder/coder/v2/testutil"
 )

 func TestShow(t *testing.T) {
@@ -28,7 +30,7 @@ func TestShow(t *testing.T) {
 		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
 		template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
 		workspace := coderdtest.CreateWorkspace(t, member, template.ID)
-		coderdtest.AwaitWorkspaceBuildJobCompleted(t, client, workspace.LatestBuild.ID)
+		build := coderdtest.AwaitWorkspaceBuildJobCompleted(t, client, workspace.LatestBuild.ID)

 		args := []string{
 			"show",
@@ -38,26 +40,30 @@ func TestShow(t *testing.T) {
 		clitest.SetupConfig(t, member, root)
 		doneChan := make(chan struct{})
 		pty := ptytest.New(t).Attach(inv)
+		ctx := testutil.Context(t, testutil.WaitShort)
 		go func() {
 			defer close(doneChan)
-			err := inv.Run()
+			err := inv.WithContext(ctx).Run()
 			assert.NoError(t, err)
 		}()
 		matches := []struct {
 			match string
 			write string
 		}{
+			{match: fmt.Sprintf("%s/%s", workspace.OwnerName, workspace.Name)},
+			{match: fmt.Sprintf("(%s since ", build.Status)},
+			{match: fmt.Sprintf("%s:%s", workspace.TemplateName, workspace.LatestBuild.TemplateVersionName)},
 			{match: "compute.main"},
 			{match: "smith (linux, i386)"},
 			{match: "coder ssh " + workspace.Name},
 		}
 		for _, m := range matches {
-			pty.ExpectMatch(m.match)
+			pty.ExpectMatchContext(ctx, m.match)
 			if len(m.write) > 0 {
 				pty.WriteLine(m.write)
 			}
 		}
-		<-doneChan
+		_ = testutil.TryReceive(ctx, t, doneChan)
 	})
 }

@@ -7,6 +7,7 @@ import (
 	"encoding/base64"
 	"encoding/json"
 	"fmt"
+	"net/http"
 	"net/url"
 	"os"
 	"path/filepath"
@@ -44,13 +45,18 @@ var supportBundleBlurb = cliui.Bold("This will collect the following information
 	`  - Coder deployment version
  - Coder deployment Configuration (sanitized), including enabled experiments
  - Coder deployment health snapshot
+  - Coder deployment stats (aggregated workspace/session metrics)
+  - Entitlements (if available)
+  - Health settings (dismissed healthchecks)
  - Coder deployment Network troubleshooting information
+  - Workspace list accessible to the user (sanitized)
  - Workspace configuration, parameters, and build logs
  - Template version and source code for the given workspace
  - Agent details (with environment variable sanitized)
  - Agent network diagnostics
  - Agent logs
  - License status
+  - pprof profiling data (if --pprof is enabled)
 ` + cliui.Bold("Note: ") +
 	cliui.Wrap("While we try to sanitize sensitive data from support bundles, we cannot guarantee that they do not contain information that you or your organization may consider sensitive.\n") +
 	cliui.Bold("Please confirm that you will:\n") +
@@ -61,6 +67,9 @@ var supportBundleBlurb = cliui.Bold("This will collect the following information
 func (r *RootCmd) supportBundle() *serpent.Command {
 	var outputPath string
 	var coderURLOverride string
+	var workspacesTotalCap64 int64 = 10
+	var templateName string
+	var pprof bool
 	cmd := &serpent.Command{
 		Use:   "bundle <workspace> [<agent>]",
 		Short: "Generate a support bundle to troubleshoot issues connecting to a workspace.",
@@ -121,8 +130,9 @@ func (r *RootCmd) supportBundle() *serpent.Command {
 			}

 			var (
-				wsID  uuid.UUID
-				agtID uuid.UUID
+				wsID       uuid.UUID
+				agtID      uuid.UUID
+				templateID uuid.UUID
 			)

 			if len(inv.Args) == 0 {
@@ -155,6 +165,16 @@ func (r *RootCmd) supportBundle() *serpent.Command {
 				}
 			}

+			// Resolve template by name if provided (captures active version)
+			// Fallback: if canonical name lookup fails, match DisplayName (case-insensitive).
+			if templateName != "" {
+				id, err := resolveTemplateID(inv.Context(), client, templateName)
+				if err != nil {
+					return err
+				}
+				templateID = id
+			}
+
 			if outputPath == "" {
 				cwd, err := filepath.Abs(".")
 				if err != nil {
@@ -176,12 +196,25 @@ func (r *RootCmd) supportBundle() *serpent.Command {
 			if r.verbose {
 				clientLog.AppendSinks(sloghuman.Sink(inv.Stderr))
 			}
+			if pprof {
+				_, _ = fmt.Fprintln(inv.Stderr, "pprof data collection will take approximately 30 seconds...")
+			}
+
+			// Bypass rate limiting for support bundle collection since it makes many API calls.
+			client.HTTPClient.Transport = &codersdk.HeaderTransport{
+				Transport: client.HTTPClient.Transport,
+				Header:    http.Header{codersdk.BypassRatelimitHeader: {"true"}},
+			}
+
 			deps := support.Deps{
 				Client: client,
 				// Support adds a sink so we don't need to supply one ourselves.
-				Log:         clientLog,
-				WorkspaceID: wsID,
-				AgentID:     agtID,
+				Log:                clientLog,
+				WorkspaceID:        wsID,
+				AgentID:            agtID,
+				WorkspacesTotalCap: int(workspacesTotalCap64),
+				TemplateID:         templateID,
+				CollectPprof:       pprof,
 			}

 			bun, err := support.Run(inv.Context(), &deps)
@@ -217,11 +250,102 @@ func (r *RootCmd) supportBundle() *serpent.Command {
 			Description: "Override the URL to your Coder deployment. This may be useful, for example, if you need to troubleshoot a specific Coder replica.",
 			Value:       serpent.StringOf(&coderURLOverride),
 		},
+		{
+			Flag:        "workspaces-total-cap",
+			Env:         "CODER_SUPPORT_BUNDLE_WORKSPACES_TOTAL_CAP",
+			Description: "Maximum number of workspaces to include in the support bundle. Set to 0 or negative value to disable the cap. Defaults to 10.",
+			Value:       serpent.Int64Of(&workspacesTotalCap64),
+		},
+		{
+			Flag:        "template",
+			Env:         "CODER_SUPPORT_BUNDLE_TEMPLATE",
+			Description: "Template name to include in the support bundle. Use org_name/template_name if template name is reused across multiple organizations.",
+			Value:       serpent.StringOf(&templateName),
+		},
+		{
+			Flag:        "pprof",
+			Env:         "CODER_SUPPORT_BUNDLE_PPROF",
+			Description: "Collect pprof profiling data from the Coder server and agent. Requires Coder server version 2.28.0 or newer.",
+			Value:       serpent.BoolOf(&pprof),
+		},
 	}

 	return cmd
 }

+// Resolve a template to its ID, supporting:
+// - org/name form
+// - slug or display name match (case-insensitive) across all memberships
+func resolveTemplateID(ctx context.Context, client *codersdk.Client, templateArg string) (uuid.UUID, error) {
+	orgPart := ""
+	namePart := templateArg
+	if slash := strings.IndexByte(templateArg, '/'); slash > 0 && slash < len(templateArg)-1 {
+		orgPart = templateArg[:slash]
+		namePart = templateArg[slash+1:]
+	}
+
+	resolveInOrg := func(orgID uuid.UUID) (codersdk.Template, bool, error) {
+		if t, err := client.TemplateByName(ctx, orgID, namePart); err == nil {
+			return t, true, nil
+		}
+		tpls, err := client.TemplatesByOrganization(ctx, orgID)
+		if err != nil {
+			return codersdk.Template{}, false, nil
+		}
+		for _, t := range tpls {
+			if strings.EqualFold(t.Name, namePart) || strings.EqualFold(t.DisplayName, namePart) {
+				return t, true, nil
+			}
+		}
+		return codersdk.Template{}, false, nil
+	}
+
+	if orgPart != "" {
+		org, err := client.OrganizationByName(ctx, orgPart)
+		if err != nil {
+			return uuid.Nil, xerrors.Errorf("get organization %q: %w", orgPart, err)
+		}
+		t, found, err := resolveInOrg(org.ID)
+		if err != nil {
+			return uuid.Nil, err
+		}
+		if !found {
+			return uuid.Nil, xerrors.Errorf("template %q not found in organization %q", namePart, orgPart)
+		}
+		return t.ID, nil
+	}
+
+	orgs, err := client.OrganizationsByUser(ctx, codersdk.Me)
+	if err != nil {
+		return uuid.Nil, xerrors.Errorf("get organizations: %w", err)
+	}
+	var (
+		foundTpl  codersdk.Template
+		foundOrgs []string
+	)
+	for _, org := range orgs {
+		if t, found, err := resolveInOrg(org.ID); err == nil && found {
+			if len(foundOrgs) == 0 {
+				foundTpl = t
+			}
+			foundOrgs = append(foundOrgs, org.Name)
+		}
+	}
+	switch len(foundOrgs) {
+	case 0:
+		return uuid.Nil, xerrors.Errorf("template %q not found in your organizations", namePart)
+	case 1:
+		return foundTpl.ID, nil
+	default:
+		return uuid.Nil, xerrors.Errorf(
+			"template %q found in multiple organizations (%s); use --template \"<org_name/%s>\" to target desired template.",
+			namePart,
+			strings.Join(foundOrgs, ", "),
+			namePart,
+		)
+	}
+}
+
 // summarizeBundle makes a best-effort attempt to write a short summary
 // of the support bundle to the user's terminal.
 func summarizeBundle(inv *serpent.Invocation, bun *support.Bundle) {
@@ -283,6 +407,10 @@ func writeBundle(src *support.Bundle, dest *zip.Writer) error {
 		"deployment/config.json":          src.Deployment.Config,
 		"deployment/experiments.json":     src.Deployment.Experiments,
 		"deployment/health.json":          src.Deployment.HealthReport,
+		"deployment/stats.json":           src.Deployment.Stats,
+		"deployment/entitlements.json":    src.Deployment.Entitlements,
+		"deployment/health_settings.json": src.Deployment.HealthSettings,
+		"deployment/workspaces.json":      src.Deployment.Workspaces,
 		"network/connection_info.json":    src.Network.ConnectionInfo,
 		"network/netcheck.json":           src.Network.Netcheck,
 		"network/interfaces.json":         src.Network.Interfaces,
@@ -302,6 +430,49 @@ func writeBundle(src *support.Bundle, dest *zip.Writer) error {
 		}
 	}

+	// Include named template artifacts (if requested)
+	if src.NamedTemplate.Template.ID != uuid.Nil {
+		name := src.NamedTemplate.Template.Name
+		// JSON files
+		for k, v := range map[string]any{
+			"templates/" + name + "/template.json":         src.NamedTemplate.Template,
+			"templates/" + name + "/template_version.json": src.NamedTemplate.TemplateVersion,
+		} {
+			f, err := dest.Create(k)
+			if err != nil {
+				return xerrors.Errorf("create file %q in archive: %w", k, err)
+			}
+			enc := json.NewEncoder(f)
+			enc.SetIndent("", "    ")
+			if err := enc.Encode(v); err != nil {
+				return xerrors.Errorf("write json to %q: %w", k, err)
+			}
+		}
+		// Binary template file (zip)
+		if namedZipBytes, err := base64.StdEncoding.DecodeString(src.NamedTemplate.TemplateFileBase64); err == nil {
+			k := "templates/" + name + "/template_file.zip"
+			f, err := dest.Create(k)
+			if err != nil {
+				return xerrors.Errorf("create file %q in archive: %w", k, err)
+			}
+			if _, err := f.Write(namedZipBytes); err != nil {
+				return xerrors.Errorf("write file %q in archive: %w", k, err)
+			}
+		}
+	}
+
+	var buildInfoRef string
+	if src.Deployment.BuildInfo != nil {
+		if raw, err := json.Marshal(src.Deployment.BuildInfo); err == nil {
+			buildInfoRef = base64.StdEncoding.EncodeToString(raw)
+		}
+	}
+
+	tailnetHTML := src.Network.TailnetDebug
+	if buildInfoRef != "" {
+		tailnetHTML += "\n<!-- trace " + buildInfoRef + " -->"
+	}
+
 	templateVersionBytes, err := base64.StdEncoding.DecodeString(src.Workspace.TemplateFileBase64)
 	if err != nil {
 		return xerrors.Errorf("decode template zip from base64")
@@ -319,10 +490,11 @@ func writeBundle(src *support.Bundle, dest *zip.Writer) error {
 		"agent/client_magicsock.html":    string(src.Agent.ClientMagicsockHTML),
 		"agent/startup_logs.txt":         humanizeAgentLogs(src.Agent.StartupLogs),
 		"agent/prometheus.txt":           string(src.Agent.Prometheus),
+		"deployment/prometheus.txt":      string(src.Deployment.Prometheus),
 		"cli_logs.txt":                   string(src.CLILogs),
 		"logs.txt":                       strings.Join(src.Logs, "\n"),
 		"network/coordinator_debug.html": src.Network.CoordinatorDebug,
-		"network/tailnet_debug.html":     src.Network.TailnetDebug,
+		"network/tailnet_debug.html":     tailnetHTML,
 		"workspace/build_logs.txt":       humanizeBuildLogs(src.Workspace.BuildLogs),
 		"workspace/template_file.zip":    string(templateVersionBytes),
 		"license-status.txt":             licenseStatus,
@@ -335,12 +507,89 @@ func writeBundle(src *support.Bundle, dest *zip.Writer) error {
 			return xerrors.Errorf("write file %q in archive: %w", k, err)
 		}
 	}
+
+	// Write pprof binary data
+	if err := writePprofData(src.Pprof, dest); err != nil {
+		return xerrors.Errorf("write pprof data: %w", err)
+	}
+
 	if err := dest.Close(); err != nil {
 		return xerrors.Errorf("close zip file: %w", err)
 	}
 	return nil
 }

+func writePprofData(pprof support.Pprof, dest *zip.Writer) error {
+	// Write server pprof data directly to pprof directory
+	if pprof.Server != nil {
+		if err := writePprofCollection("pprof", pprof.Server, dest); err != nil {
+			return xerrors.Errorf("write server pprof data: %w", err)
+		}
+	}
+
+	// Write agent pprof data
+	if pprof.Agent != nil {
+		if err := writePprofCollection("pprof/agent", pprof.Agent, dest); err != nil {
+			return xerrors.Errorf("write agent pprof data: %w", err)
+		}
+	}
+
+	return nil
+}
+
+func writePprofCollection(basePath string, collection *support.PprofCollection, dest *zip.Writer) error {
+	// Define the pprof files to write with their extensions
+	files := map[string][]byte{
+		"allocs.prof.gz":       collection.Allocs,
+		"heap.prof.gz":         collection.Heap,
+		"profile.prof.gz":      collection.Profile,
+		"block.prof.gz":        collection.Block,
+		"mutex.prof.gz":        collection.Mutex,
+		"goroutine.prof.gz":    collection.Goroutine,
+		"threadcreate.prof.gz": collection.Threadcreate,
+		"trace.gz":             collection.Trace,
+	}
+
+	// Write binary pprof files
+	for filename, data := range files {
+		if len(data) > 0 {
+			filePath := basePath + "/" + filename
+			f, err := dest.Create(filePath)
+			if err != nil {
+				return xerrors.Errorf("create pprof file %q: %w", filePath, err)
+			}
+			if _, err := f.Write(data); err != nil {
+				return xerrors.Errorf("write pprof file %q: %w", filePath, err)
+			}
+		}
+	}
+
+	// Write cmdline as text file
+	if collection.Cmdline != "" {
+		filePath := basePath + "/cmdline.txt"
+		f, err := dest.Create(filePath)
+		if err != nil {
+			return xerrors.Errorf("create cmdline file %q: %w", filePath, err)
+		}
+		if _, err := f.Write([]byte(collection.Cmdline)); err != nil {
+			return xerrors.Errorf("write cmdline file %q: %w", filePath, err)
+		}
+	}
+
+	if collection.Symbol != "" {
+		filePath := basePath + "/symbol.txt"
+		f, err := dest.Create(filePath)
+		if err != nil {
+			return xerrors.Errorf("create symbol file %q: %w", filePath, err)
+		}
+		if _, err := f.Write([]byte(collection.Symbol)); err != nil {
+			return xerrors.Errorf("write symbol file %q: %w", filePath, err)
+		}
+	}
+
+	return nil
+}
+
 func humanizeAgentLogs(ls []codersdk.WorkspaceAgentLog) string {
 	var buf bytes.Buffer
 	tw := tabwriter.NewWriter(&buf, 0, 2, 1, ' ', 0)
@@ -46,6 +46,8 @@ func TestSupportBundle(t *testing.T) {

 	// Support bundle tests can share a single coderdtest instance.
 	var dc codersdk.DeploymentConfig
+	dc.Values = coderdtest.DeploymentValues(t)
+	dc.Values.Prometheus.Enable = true
 	secretValue := uuid.NewString()
 	seedSecretDeploymentOptions(t, &dc, secretValue)
 	client, closer, api := coderdtest.NewWithAPI(t, &coderdtest.Options{
@@ -203,6 +205,10 @@ func assertBundleContents(t *testing.T, path string, wantWorkspace bool, wantAge
 			var v codersdk.DeploymentConfig
 			decodeJSONFromZip(t, f, &v)
 			require.NotEmpty(t, v, "deployment config should not be empty")
+		case "deployment/entitlements.json":
+			var v codersdk.Entitlements
+			decodeJSONFromZip(t, f, &v)
+			require.NotNil(t, v, "entitlements should not be nil")
 		case "deployment/experiments.json":
 			var v codersdk.Experiments
 			decodeJSONFromZip(t, f, &v)
@@ -211,6 +217,22 @@ func assertBundleContents(t *testing.T, path string, wantWorkspace bool, wantAge
 			var v healthsdk.HealthcheckReport
 			decodeJSONFromZip(t, f, &v)
 			require.NotEmpty(t, v, "health report should not be empty")
+		case "deployment/health_settings.json":
+			var v healthsdk.HealthSettings
+			decodeJSONFromZip(t, f, &v)
+			require.NotEmpty(t, v, "health settings should not be empty")
+		case "deployment/stats.json":
+			var v codersdk.DeploymentStats
+			decodeJSONFromZip(t, f, &v)
+			require.NotNil(t, v, "deployment stats should not be nil")
+		case "deployment/workspaces.json":
+			var v codersdk.Workspace
+			decodeJSONFromZip(t, f, &v)
+			require.NotNil(t, v, "deployment workspaces should not be nil")
+		case "deployment/prometheus.txt":
+			bs := readBytesFromZip(t, f)
+			require.NotEmpty(t, bs, "prometheus metrics should not be empty")
+			require.Contains(t, string(bs), "go_goroutines", "prometheus metrics should contain go runtime metrics")
 		case "network/connection_info.json":
 			var v workspacesdk.AgentConnectionInfo
 			decodeJSONFromZip(t, f, &v)
@@ -7,7 +7,7 @@ USAGE:

 OPTIONS:
  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -55,7 +55,7 @@ OPTIONS:
          configured in the workspace template is used.

  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -49,8 +49,11 @@ OPTIONS:
      --template-version string, $CODER_TEMPLATE_VERSION
          Specify a template version name.

+      --use-parameter-defaults bool, $CODER_WORKSPACE_USE_PARAMETER_DEFAULTS
+          Automatically accept parameter defaults when no value is provided.
+
  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -18,7 +18,7 @@ OPTIONS:
          resources.

  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -24,7 +24,7 @@ OPTIONS:
          empty, will use $HOME.

  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -7,7 +7,7 @@ USAGE:

 OPTIONS:
  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -7,7 +7,7 @@ USAGE:

 OPTIONS:
  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -18,7 +18,7 @@ OPTIONS:
          Reads stdin for the json role definition to upload.

  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -23,7 +23,7 @@ OPTIONS:
          Reads stdin for the json role definition to upload.

  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -15,6 +15,7 @@ SUBCOMMANDS:
                         memberships from an IdP.
    role-sync            Role sync settings to sync organization roles from an
                         IdP.
+    workspace-sharing    Workspace sharing settings for the organization.

 ———
 Run `coder --help` for a list of global options.
@@ -15,6 +15,7 @@ SUBCOMMANDS:
                         memberships from an IdP.
    role-sync            Role sync settings to sync organization roles from an
                         IdP.
+    workspace-sharing    Workspace sharing settings for the organization.

 ———
 Run `coder --help` for a list of global options.
@@ -15,6 +15,7 @@ SUBCOMMANDS:
                         memberships from an IdP.
    role-sync            Role sync settings to sync organization roles from an
                         IdP.
+    workspace-sharing    Workspace sharing settings for the organization.

 ———
 Run `coder --help` for a list of global options.
@@ -15,6 +15,7 @@ SUBCOMMANDS:
                         memberships from an IdP.
    role-sync            Role sync settings to sync organization roles from an
                         IdP.
+    workspace-sharing    Workspace sharing settings for the organization.

 ———
 Run `coder --help` for a list of global options.
@@ -13,7 +13,7 @@ OPTIONS:
          services it's registered with.

  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -7,7 +7,7 @@ USAGE:

 OPTIONS:
  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -39,7 +39,7 @@ OPTIONS:
          pairs for the parameters.

  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -15,9 +15,11 @@ SUBCOMMANDS:

 OPTIONS:
      --allow-workspace-renames bool, $CODER_ALLOW_WORKSPACE_RENAMES (default: false)
-          DEPRECATED: Allow users to rename their workspaces. Use only for
-          temporary compatibility reasons, this will be removed in a future
-          release.
+          Allow users to rename their workspaces. WARNING: Renaming a workspace
+          can cause Terraform resources that depend on the workspace name to be
+          destroyed and recreated, potentially causing data loss. Only enable
+          this if your templates do not use workspace names in resource
+          identifiers, or if you understand the risks.

      --cache-dir string, $CODER_CACHE_DIRECTORY (default: [cache dir])
          The directory to cache temporary files. If unspecified and
@@ -109,11 +111,18 @@ AI BRIDGE OPTIONS:
          The access key secret to use with the access key to authenticate
          against the AWS Bedrock API.

+      --aibridge-bedrock-base-url string, $CODER_AIBRIDGE_BEDROCK_BASE_URL
+          The base URL to use for the AWS Bedrock API. Use this setting to
+          specify an exact URL to use. Takes precedence over
+          CODER_AIBRIDGE_BEDROCK_REGION.
+
      --aibridge-bedrock-model string, $CODER_AIBRIDGE_BEDROCK_MODEL (default: global.anthropic.claude-sonnet-4-5-20250929-v1:0)
          The model to use when making requests to the AWS Bedrock API.

      --aibridge-bedrock-region string, $CODER_AIBRIDGE_BEDROCK_REGION
-          The AWS Bedrock API region.
+          The AWS Bedrock API region to use. Constructs a base URL to use for
+          the AWS Bedrock API in the form of
+          'https://bedrock-runtime.<region>.amazonaws.com'.

      --aibridge-bedrock-small-fastmodel string, $CODER_AIBRIDGE_BEDROCK_SMALL_FAST_MODEL (default: global.anthropic.claude-haiku-4-5-20251001-v1:0)
          The small fast model to use when making requests to the AWS Bedrock
@@ -121,6 +130,10 @@ AI BRIDGE OPTIONS:
          See
          https://docs.claude.com/en/docs/claude-code/settings#environment-variables.

+      --aibridge-circuit-breaker-enabled bool, $CODER_AIBRIDGE_CIRCUIT_BREAKER_ENABLED (default: false)
+          Enable the circuit breaker to protect against cascading failures from
+          upstream AI provider rate limits (429, 503, 529 overloaded).
+
      --aibridge-retention duration, $CODER_AIBRIDGE_RETENTION (default: 60d)
          Length of time to retain data such as interceptions and all related
          records (token, prompt, tool use).
@@ -147,6 +160,18 @@ AI BRIDGE OPTIONS:
          Maximum number of AI Bridge requests per second per replica. Set to 0
          to disable (unlimited).

+      --aibridge-send-actor-headers bool, $CODER_AIBRIDGE_SEND_ACTOR_HEADERS (default: false)
+          Once enabled, extra headers will be added to upstream requests to
+          identify the user (actor) making requests to AI Bridge. This is only
+          needed if you are using a proxy between AI Bridge and an upstream AI
+          provider. This will send X-Ai-Bridge-Actor-Id (the ID of the user
+          making the request) and X-Ai-Bridge-Actor-Metadata-Username (their
+          username).
+
+      --aibridge-structured-logging bool, $CODER_AIBRIDGE_STRUCTURED_LOGGING (default: false)
+          Emit structured logs for AI Bridge interception records. Use this for
+          exporting these records to external SIEM or observability systems.
+
 AI BRIDGE PROXY OPTIONS: 
      --aibridge-proxy-cert-file string, $CODER_AIBRIDGE_PROXY_CERT_FILE
          Path to the CA certificate file for AI Bridge Proxy.
@@ -161,6 +186,17 @@ AI BRIDGE PROXY OPTIONS:
      --aibridge-proxy-listen-addr string, $CODER_AIBRIDGE_PROXY_LISTEN_ADDR (default: :8888)
          The address the AI Bridge Proxy will listen on.

+      --aibridge-proxy-upstream string, $CODER_AIBRIDGE_PROXY_UPSTREAM
+          URL of an upstream HTTP proxy to chain tunneled (non-allowlisted)
+          requests through. Format: http://[user:pass@]host:port or
+          https://[user:pass@]host:port.
+
+      --aibridge-proxy-upstream-ca string, $CODER_AIBRIDGE_PROXY_UPSTREAM_CA
+          Path to a PEM-encoded CA certificate to trust for the upstream proxy's
+          TLS connection. Only needed for HTTPS upstream proxies with
+          certificates not trusted by the system. If not provided, the system
+          certificate pool is used.
+
 CLIENT OPTIONS: 
 These options change the behavior of how clients interact with the Coder.
 Clients include the Coder CLI, Coder Desktop, IDE extensions, and the web UI.
@@ -42,7 +42,7 @@ OPTIONS:
          pairs for the parameters.

  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -7,7 +7,7 @@ USAGE:

 OPTIONS:
  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -14,12 +14,25 @@ OPTIONS:
          File path for writing the generated support bundle. Defaults to
          coder-support-$(date +%s).zip.

+      --pprof bool, $CODER_SUPPORT_BUNDLE_PPROF
+          Collect pprof profiling data from the Coder server and agent. Requires
+          Coder server version 2.28.0 or newer.
+
+      --template string, $CODER_SUPPORT_BUNDLE_TEMPLATE
+          Template name to include in the support bundle. Use
+          org_name/template_name if template name is reused across multiple
+          organizations.
+
      --url-override string, $CODER_SUPPORT_BUNDLE_URL_OVERRIDE
          Override the URL to your Coder deployment. This may be useful, for
          example, if you need to troubleshoot a specific Coder replica.

+      --workspaces-total-cap int, $CODER_SUPPORT_BUNDLE_WORKSPACES_TOTAL_CAP
+          Maximum number of workspaces to include in the support bundle. Set to
+          0 or negative value to disable the cap. Defaults to 10.
+
  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -21,7 +21,7 @@ USAGE:

 OPTIONS:
  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -14,7 +14,7 @@ OPTIONS:
          versions are archived.

  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -68,7 +68,7 @@ OPTIONS:
          Specify a file path with values for Terraform-managed variables.

  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -12,7 +12,7 @@ OPTIONS:
          Select which organization (uuid or name) to use.

  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -91,7 +91,7 @@ OPTIONS:
          for more details.

  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -18,7 +18,7 @@ OPTIONS:
          the template version to pull.

  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

      --zip bool
          Output the template as a zip archive to stdout.
@@ -48,7 +48,7 @@ OPTIONS:
          Specify a file path with values for Terraform-managed variables.

  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -11,7 +11,7 @@ OPTIONS:
          Select which organization (uuid or name) to use.

  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -11,7 +11,7 @@ OPTIONS:
          Select which organization (uuid or name) to use.

  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -11,7 +11,7 @@ OPTIONS:
          the user may have.

  -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.

 ———
 Run `coder --help` for a list of global options.
@@ -575,8 +575,10 @@ userQuietHoursSchedule:
  # change their quiet hours schedule and the site default is always used.
  # (default: true, type: bool)
  allowCustomQuietHours: true
-# DEPRECATED: Allow users to rename their workspaces. Use only for temporary
-# compatibility reasons, this will be removed in a future release.
+# Allow users to rename their workspaces. WARNING: Renaming a workspace can cause
+# Terraform resources that depend on the workspace name to be destroyed and
+# recreated, potentially causing data loss. Only enable this if your templates do
+# not use workspace names in resource identifiers, or if you understand the risks.
 # (default: false, type: bool)
 allowWorkspaceRenames: false
 # Configure how emails are sent.
@@ -746,7 +748,12 @@ aibridge:
  # The base URL of the Anthropic API.
  # (default: https://api.anthropic.com/, type: string)
  anthropic_base_url: https://api.anthropic.com/
-  # The AWS Bedrock API region.
+  # The base URL to use for the AWS Bedrock API. Use this setting to specify an
+  # exact URL to use. Takes precedence over CODER_AIBRIDGE_BEDROCK_REGION.
+  # (default: <unset>, type: string)
+  bedrock_base_url: ""
+  # The AWS Bedrock API region to use. Constructs a base URL to use for the AWS
+  # Bedrock API in the form of 'https://bedrock-runtime.<region>.amazonaws.com'.
  # (default: <unset>, type: string)
  bedrock_region: ""
  # The model to use when making requests to the AWS Bedrock API.
@@ -768,11 +775,39 @@ aibridge:
  # Maximum number of concurrent AI Bridge requests per replica. Set to 0 to disable
  # (unlimited).
  # (default: 0, type: int)
-  maxConcurrency: 0
+  max_concurrency: 0
  # Maximum number of AI Bridge requests per second per replica. Set to 0 to disable
  # (unlimited).
  # (default: 0, type: int)
-  rateLimit: 0
+  rate_limit: 0
+  # Emit structured logs for AI Bridge interception records. Use this for exporting
+  # these records to external SIEM or observability systems.
+  # (default: false, type: bool)
+  structured_logging: false
+  # Once enabled, extra headers will be added to upstream requests to identify the
+  # user (actor) making requests to AI Bridge. This is only needed if you are using
+  # a proxy between AI Bridge and an upstream AI provider. This will send
+  # X-Ai-Bridge-Actor-Id (the ID of the user making the request) and
+  # X-Ai-Bridge-Actor-Metadata-Username (their username).
+  # (default: false, type: bool)
+  send_actor_headers: false
+  # Enable the circuit breaker to protect against cascading failures from upstream
+  # AI provider rate limits (429, 503, 529 overloaded).
+  # (default: false, type: bool)
+  circuit_breaker_enabled: false
+  # Number of consecutive failures that triggers the circuit breaker to open.
+  # (default: 5, type: int)
+  circuit_breaker_failure_threshold: 5
+  # Cyclic period of the closed state for clearing internal failure counts.
+  # (default: 10s, type: duration)
+  circuit_breaker_interval: 10s
+  # How long the circuit breaker stays open before transitioning to half-open state.
+  # (default: 30s, type: duration)
+  circuit_breaker_timeout: 30s
+  # Maximum number of requests allowed in half-open state before deciding to close
+  # or re-open the circuit.
+  # (default: 3, type: int)
+  circuit_breaker_max_requests: 3
 aibridgeproxy:
  # Enable the AI Bridge MITM Proxy for intercepting and decrypting AI provider
  # requests.
@@ -787,13 +822,25 @@ aibridgeproxy:
  # Path to the CA private key file for AI Bridge Proxy.
  # (default: <unset>, type: string)
  key_file: ""
-  # Comma-separated list of domains for which HTTPS traffic will be decrypted and
-  # routed through AI Bridge. Requests to other domains will be tunneled directly
-  # without decryption.
-  # (default: api.anthropic.com,api.openai.com, type: string-array)
+  # Comma-separated list of AI provider domains for which HTTPS traffic will be
+  # decrypted and routed through AI Bridge. Requests to other domains will be
+  # tunneled directly without decryption. Supported domains: api.anthropic.com,
+  # api.openai.com, api.individual.githubcopilot.com.
+  # (default: api.anthropic.com,api.openai.com,api.individual.githubcopilot.com,
+  # type: string-array)
  domain_allowlist:
    - api.anthropic.com
    - api.openai.com
+    - api.individual.githubcopilot.com
+  # URL of an upstream HTTP proxy to chain tunneled (non-allowlisted) requests
+  # through. Format: http://[user:pass@]host:port or https://[user:pass@]host:port.
+  # (default: <unset>, type: string)
+  upstream_proxy: ""
+  # Path to a PEM-encoded CA certificate to trust for the upstream proxy's TLS
+  # connection. Only needed for HTTPS upstream proxies with certificates not trusted
+  # by the system. If not provided, the system certificate pool is used.
+  # (default: <unset>, type: string)
+  upstream_proxy_ca: ""
 # Configure data retention policies for various database tables. Retention
 # policies automatically purge old data to reduce database size and improve
 # performance. Setting a retention duration to 0 disables automatic purging for
@@ -17,8 +17,10 @@ import (

 	"cdr.dev/slog/v3"
 	agentproto "github.com/coder/coder/v2/agent/proto"
+	"github.com/coder/coder/v2/coderd/agentapi/metadatabatcher"
 	"github.com/coder/coder/v2/coderd/agentapi/resourcesmonitor"
 	"github.com/coder/coder/v2/coderd/appearance"
+	"github.com/coder/coder/v2/coderd/boundaryusage"
 	"github.com/coder/coder/v2/coderd/connectionlog"
 	"github.com/coder/coder/v2/coderd/database"
 	"github.com/coder/coder/v2/coderd/database/pubsub"
@@ -65,10 +67,11 @@ type API struct {
 var _ agentproto.DRPCAgentServer = &API{}

 type Options struct {
-	AgentID        uuid.UUID
-	OwnerID        uuid.UUID
-	WorkspaceID    uuid.UUID
-	OrganizationID uuid.UUID
+	AgentID           uuid.UUID
+	OwnerID           uuid.UUID
+	WorkspaceID       uuid.UUID
+	OrganizationID    uuid.UUID
+	TemplateVersionID uuid.UUID

 	AuthenticatedCtx                  context.Context
 	Log                               slog.Logger
@@ -80,10 +83,12 @@ type Options struct {
 	DerpMapFn                         func() *tailcfg.DERPMap
 	TailnetCoordinator                *atomic.Pointer[tailnet.Coordinator]
 	StatsReporter                     *workspacestats.Reporter
+	MetadataBatcher                   *metadatabatcher.Batcher
 	AppearanceFetcher                 *atomic.Pointer[appearance.Fetcher]
 	PublishWorkspaceUpdateFn          func(ctx context.Context, userID uuid.UUID, event wspubsub.WorkspaceEvent)
 	PublishWorkspaceAgentLogsUpdateFn func(ctx context.Context, workspaceAgentID uuid.UUID, msg agentsdk.LogsNotifyMessage)
 	NetworkTelemetryHandler           func(batch []*tailnetproto.TelemetryEvent)
+	BoundaryUsageTracker              *boundaryusage.Tracker

 	AccessURL                 *url.URL
 	AppHostname               string
@@ -178,8 +183,8 @@ func New(opts Options, workspace database.Workspace) *API {
 		AgentFn:   api.agent,
 		Workspace: api.cachedWorkspaceFields,
 		Database:  opts.Database,
-		Pubsub:    opts.Pubsub,
 		Log:       opts.Log,
+		Batcher:   opts.MetadataBatcher,
 	}

 	api.LogsAPI = &LogsAPI{
@@ -221,8 +226,12 @@ func New(opts Options, workspace database.Workspace) *API {
 	}

 	api.BoundaryLogsAPI = &BoundaryLogsAPI{
-		Log:         opts.Log,
-		WorkspaceID: opts.WorkspaceID,
+		Log:                  opts.Log,
+		WorkspaceID:          opts.WorkspaceID,
+		OwnerID:              opts.OwnerID,
+		TemplateID:           workspace.TemplateID,
+		TemplateVersionID:    opts.TemplateVersionID,
+		BoundaryUsageTracker: opts.BoundaryUsageTracker,
 	}

 	// Start background cache refresh loop to handle workspace changes
@@ -8,14 +8,21 @@ import (

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

 type BoundaryLogsAPI struct {
-	Log         slog.Logger
-	WorkspaceID uuid.UUID
+	Log                  slog.Logger
+	WorkspaceID          uuid.UUID
+	OwnerID              uuid.UUID
+	TemplateID           uuid.UUID
+	TemplateVersionID    uuid.UUID
+	BoundaryUsageTracker *boundaryusage.Tracker
 }

 func (a *BoundaryLogsAPI) ReportBoundaryLogs(ctx context.Context, req *agentproto.ReportBoundaryLogsRequest) (*agentproto.ReportBoundaryLogsResponse, error) {
+	var allowed, denied int64
+
 	for _, l := range req.Logs {
 		var logTime time.Time
 		if l.Time != nil {
@@ -30,9 +37,17 @@ func (a *BoundaryLogsAPI) ReportBoundaryLogs(ctx context.Context, req *agentprot
 				continue
 			}

+			if l.Allowed {
+				allowed++
+			} else {
+				denied++
+			}
+
 			fields := []slog.Field{
 				slog.F("decision", allowBoolToString(l.Allowed)),
 				slog.F("workspace_id", a.WorkspaceID.String()),
+				slog.F("template_id", a.TemplateID.String()),
+				slog.F("template_version_id", a.TemplateVersionID.String()),
 				slog.F("http_method", r.HttpRequest.Method),
 				slog.F("http_url", r.HttpRequest.Url),
 				slog.F("event_time", logTime.Format(time.RFC3339Nano)),
@@ -48,6 +63,10 @@ func (a *BoundaryLogsAPI) ReportBoundaryLogs(ctx context.Context, req *agentprot
 		}
 	}

+	if a.BoundaryUsageTracker != nil && (allowed > 0 || denied > 0) {
+		a.BoundaryUsageTracker.Track(a.WorkspaceID, a.OwnerID, allowed, denied)
+	}
+
 	return &agentproto.ReportBoundaryLogsResponse{}, nil
 }

@@ -2,27 +2,25 @@ package agentapi

 import (
 	"context"
-	"encoding/json"
 	"fmt"
 	"time"

-	"github.com/google/uuid"
 	"golang.org/x/xerrors"

 	"cdr.dev/slog/v3"
 	agentproto "github.com/coder/coder/v2/agent/proto"
+	"github.com/coder/coder/v2/coderd/agentapi/metadatabatcher"
 	"github.com/coder/coder/v2/coderd/database"
 	"github.com/coder/coder/v2/coderd/database/dbauthz"
 	"github.com/coder/coder/v2/coderd/database/dbtime"
-	"github.com/coder/coder/v2/coderd/database/pubsub"
 )

 type MetadataAPI struct {
 	AgentFn   func(context.Context) (database.WorkspaceAgent, error)
 	Workspace *CachedWorkspaceFields
 	Database  database.Store
-	Pubsub    pubsub.Pubsub
 	Log       slog.Logger
+	Batcher   *metadatabatcher.Batcher

 	TimeNowFn func() time.Time // defaults to dbtime.Now()
 }
@@ -122,21 +120,10 @@ func (a *MetadataAPI) BatchUpdateMetadata(ctx context.Context, req *agentproto.B
 		)
 	}

-	err = a.Database.UpdateWorkspaceAgentMetadata(rbacCtx, dbUpdate)
+	// Use batcher to batch metadata updates.
+	err = a.Batcher.Add(workspaceAgent.ID, dbUpdate.Key, dbUpdate.Value, dbUpdate.Error, dbUpdate.CollectedAt)
 	if err != nil {
-		return nil, xerrors.Errorf("update workspace agent metadata in database: %w", err)
-	}
-
-	payload, err := json.Marshal(WorkspaceAgentMetadataChannelPayload{
-		CollectedAt: collectedAt,
-		Keys:        dbUpdate.Key,
-	})
-	if err != nil {
-		return nil, xerrors.Errorf("marshal workspace agent metadata channel payload: %w", err)
-	}
-	err = a.Pubsub.Publish(WatchWorkspaceAgentMetadataChannel(workspaceAgent.ID), payload)
-	if err != nil {
-		return nil, xerrors.Errorf("publish workspace agent metadata: %w", err)
+		return nil, xerrors.Errorf("add metadata to batcher: %w", err)
 	}

 	// If the metadata keys were too large, we return an error so the agent can
@@ -154,12 +141,3 @@ func ellipse(v string, n int) string {
 	}
 	return v
 }
-
-type WorkspaceAgentMetadataChannelPayload struct {
-	CollectedAt time.Time `json:"collected_at"`
-	Keys        []string  `json:"keys"`
-}
-
-func WatchWorkspaceAgentMetadataChannel(id uuid.UUID) string {
-	return "workspace_agent_metadata:" + id.String()
-}
@@ -2,44 +2,26 @@ package agentapi_test

 import (
 	"context"
-	"database/sql"
-	"encoding/json"
-	"sync/atomic"
 	"testing"
 	"time"

 	"github.com/google/uuid"
 	"github.com/prometheus/client_golang/prometheus"
+	prom_testutil "github.com/prometheus/client_golang/prometheus/testutil"
 	"github.com/stretchr/testify/require"
 	"go.uber.org/mock/gomock"
 	"google.golang.org/protobuf/types/known/timestamppb"

 	agentproto "github.com/coder/coder/v2/agent/proto"
 	"github.com/coder/coder/v2/coderd/agentapi"
+	"github.com/coder/coder/v2/coderd/agentapi/metadatabatcher"
 	"github.com/coder/coder/v2/coderd/database"
-	"github.com/coder/coder/v2/coderd/database/dbauthz"
 	"github.com/coder/coder/v2/coderd/database/dbmock"
 	"github.com/coder/coder/v2/coderd/database/dbtime"
 	"github.com/coder/coder/v2/coderd/database/pubsub"
-	"github.com/coder/coder/v2/coderd/rbac"
-	"github.com/coder/coder/v2/coderd/rbac/policy"
 	"github.com/coder/coder/v2/testutil"
-	"github.com/coder/quartz"
 )

-type fakePublisher struct {
-	// Nil pointer to pass interface check.
-	pubsub.Pubsub
-	publishes [][]byte
-}
-
-var _ pubsub.Pubsub = &fakePublisher{}
-
-func (f *fakePublisher) Publish(_ string, message []byte) error {
-	f.publishes = append(f.publishes, message)
-	return nil
-}
-
 func TestBatchUpdateMetadata(t *testing.T) {
 	t.Parallel()

@@ -50,8 +32,12 @@ func TestBatchUpdateMetadata(t *testing.T) {
 	t.Run("OK", func(t *testing.T) {
 		t.Parallel()

-		dbM := dbmock.NewMockStore(gomock.NewController(t))
-		pub := &fakePublisher{}
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		ctrl := gomock.NewController(t)
+		store := dbmock.NewMockStore(ctrl)
+		ps := pubsub.NewInMemory()
+		reg := prometheus.NewRegistry()

 		now := dbtime.Now()
 		req := &agentproto.BatchUpdateMetadataRequest{
@@ -76,24 +62,30 @@ func TestBatchUpdateMetadata(t *testing.T) {
 				},
 			},
 		}
+		batchSize := len(req.Metadata)
+		// This test sends 2 metadata entries. With batch size 2, we expect
+		// exactly 1 capacity flush.
+		store.EXPECT().
+			BatchUpdateWorkspaceAgentMetadata(gomock.Any(), gomock.Any()).
+			Return(nil).
+			Times(1)

-		dbM.EXPECT().UpdateWorkspaceAgentMetadata(gomock.Any(), database.UpdateWorkspaceAgentMetadataParams{
-			WorkspaceAgentID: agent.ID,
-			Key:              []string{req.Metadata[0].Key, req.Metadata[1].Key},
-			Value:            []string{req.Metadata[0].Result.Value, req.Metadata[1].Result.Value},
-			Error:            []string{req.Metadata[0].Result.Error, req.Metadata[1].Result.Error},
-			// The value from the agent is ignored.
-			CollectedAt: []time.Time{now, now},
-		}).Return(nil)
+		// Create a real batcher for the test with batch size matching the number
+		// of metadata entries to trigger exactly one capacity flush.
+		batcher, err := metadatabatcher.NewBatcher(ctx, reg, store, ps,
+			metadatabatcher.WithLogger(testutil.Logger(t)),
+			metadatabatcher.WithBatchSize(batchSize),
+		)
+		require.NoError(t, err)
+		t.Cleanup(batcher.Close)

 		api := &agentapi.MetadataAPI{
 			AgentFn: func(context.Context) (database.WorkspaceAgent, error) {
 				return agent, nil
 			},
 			Workspace: &agentapi.CachedWorkspaceFields{},
-			Database:  dbM,
-			Pubsub:    pub,
 			Log:       testutil.Logger(t),
+			Batcher:   batcher,
 			TimeNowFn: func() time.Time {
 				return now
 			},
@@ -103,27 +95,33 @@ func TestBatchUpdateMetadata(t *testing.T) {
 		require.NoError(t, err)
 		require.Equal(t, &agentproto.BatchUpdateMetadataResponse{}, resp)

-		require.Equal(t, 1, len(pub.publishes))
-		var gotEvent agentapi.WorkspaceAgentMetadataChannelPayload
-		require.NoError(t, json.Unmarshal(pub.publishes[0], &gotEvent))
-		require.Equal(t, agentapi.WorkspaceAgentMetadataChannelPayload{
-			CollectedAt: now,
-			Keys:        []string{req.Metadata[0].Key, req.Metadata[1].Key},
-		}, gotEvent)
+		// Wait for the capacity flush to complete before test ends.
+		testutil.Eventually(ctx, t, func(ctx context.Context) bool {
+			return prom_testutil.ToFloat64(batcher.Metrics.MetadataTotal) == 2.0
+		}, testutil.IntervalFast)
 	})

 	t.Run("ExceededLength", func(t *testing.T) {
 		t.Parallel()

-		dbM := dbmock.NewMockStore(gomock.NewController(t))
-		pub := pubsub.NewInMemory()
+		ctx := testutil.Context(t, testutil.WaitShort)
+		ctrl := gomock.NewController(t)
+		store := dbmock.NewMockStore(ctrl)
+		ps := pubsub.NewInMemory()
+		reg := prometheus.NewRegistry()

+		// This test sends 4 metadata entries with some exceeding length limits. We set the batchers batch size so that
+		// we can reliably ensure a batch is sent within the WaitShort time period.
+		store.EXPECT().
+			BatchUpdateWorkspaceAgentMetadata(gomock.Any(), gomock.Any()).
+			Return(nil).
+			Times(1)
+
+		now := dbtime.Now()
 		almostLongValue := ""
 		for i := 0; i < 2048; i++ {
 			almostLongValue += "a"
 		}
-
-		now := dbtime.Now()
 		req := &agentproto.BatchUpdateMetadataRequest{
 			Metadata: []*agentproto.Metadata{
 				{
@@ -152,34 +150,21 @@ func TestBatchUpdateMetadata(t *testing.T) {
 				},
 			},
 		}
-
-		dbM.EXPECT().UpdateWorkspaceAgentMetadata(gomock.Any(), database.UpdateWorkspaceAgentMetadataParams{
-			WorkspaceAgentID: agent.ID,
-			Key:              []string{req.Metadata[0].Key, req.Metadata[1].Key, req.Metadata[2].Key, req.Metadata[3].Key},
-			Value: []string{
-				almostLongValue,
-				almostLongValue, // truncated
-				"",
-				"",
-			},
-			Error: []string{
-				"",
-				"value of 2049 bytes exceeded 2048 bytes",
-				almostLongValue,
-				"error of 2049 bytes exceeded 2048 bytes", // replaced
-			},
-			// The value from the agent is ignored.
-			CollectedAt: []time.Time{now, now, now, now},
-		}).Return(nil)
+		batchSize := len(req.Metadata)
+		batcher, err := metadatabatcher.NewBatcher(ctx, reg, store, ps,
+			metadatabatcher.WithLogger(testutil.Logger(t)),
+			metadatabatcher.WithBatchSize(batchSize),
+		)
+		require.NoError(t, err)
+		t.Cleanup(batcher.Close)

 		api := &agentapi.MetadataAPI{
 			AgentFn: func(context.Context) (database.WorkspaceAgent, error) {
 				return agent, nil
 			},
 			Workspace: &agentapi.CachedWorkspaceFields{},
-			Database:  dbM,
-			Pubsub:    pub,
 			Log:       testutil.Logger(t),
+			Batcher:   batcher,
 			TimeNowFn: func() time.Time {
 				return now
 			},
@@ -188,13 +173,21 @@ func TestBatchUpdateMetadata(t *testing.T) {
 		resp, err := api.BatchUpdateMetadata(context.Background(), req)
 		require.NoError(t, err)
 		require.Equal(t, &agentproto.BatchUpdateMetadataResponse{}, resp)
+		// Wait for the capacity flush to complete before test ends.
+		testutil.Eventually(ctx, t, func(ctx context.Context) bool {
+			return prom_testutil.ToFloat64(batcher.Metrics.MetadataTotal) == 4.0
+		}, testutil.IntervalFast)
 	})

 	t.Run("KeysTooLong", func(t *testing.T) {
 		t.Parallel()

-		dbM := dbmock.NewMockStore(gomock.NewController(t))
-		pub := pubsub.NewInMemory()
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		ctrl := gomock.NewController(t)
+		store := dbmock.NewMockStore(ctrl)
+		ps := pubsub.NewInMemory()
+		reg := prometheus.NewRegistry()

 		now := dbtime.Now()
 		req := &agentproto.BatchUpdateMetadataRequest{
@@ -231,595 +224,40 @@ func TestBatchUpdateMetadata(t *testing.T) {
 				},
 			},
 		}
+		batchSize := len(req.Metadata)

-		dbM.EXPECT().UpdateWorkspaceAgentMetadata(gomock.Any(), database.UpdateWorkspaceAgentMetadataParams{
-			WorkspaceAgentID: agent.ID,
-			// No key 4.
-			Key:   []string{req.Metadata[0].Key, req.Metadata[1].Key, req.Metadata[2].Key},
-			Value: []string{req.Metadata[0].Result.Value, req.Metadata[1].Result.Value, req.Metadata[2].Result.Value},
-			Error: []string{req.Metadata[0].Result.Error, req.Metadata[1].Result.Error, req.Metadata[2].Result.Error},
-			// The value from the agent is ignored.
-			CollectedAt: []time.Time{now, now, now},
-		}).Return(nil)
+		// This test sends 4 metadata entries but rejects the last one due to excessive key length.
+		// We set the batchers batch size so that we can reliably ensure a batch is sent within the WaitShort time period.
+		store.EXPECT().
+			BatchUpdateWorkspaceAgentMetadata(gomock.Any(), gomock.Any()).
+			Return(nil).
+			Times(1)
+
+		batcher, err := metadatabatcher.NewBatcher(ctx, reg, store, ps,
+			metadatabatcher.WithLogger(testutil.Logger(t)),
+			metadatabatcher.WithBatchSize(batchSize-1), // one of the keys will be rejected
+		)
+		require.NoError(t, err)
+		t.Cleanup(batcher.Close)

 		api := &agentapi.MetadataAPI{
 			AgentFn: func(context.Context) (database.WorkspaceAgent, error) {
 				return agent, nil
 			},
 			Workspace: &agentapi.CachedWorkspaceFields{},
-			Database:  dbM,
-			Pubsub:    pub,
 			Log:       testutil.Logger(t),
+			Batcher:   batcher,
 			TimeNowFn: func() time.Time {
 				return now
 			},
 		}

-		// Watch the pubsub for events.
-		var (
-			eventCount int64
-			gotEvent   agentapi.WorkspaceAgentMetadataChannelPayload
-		)
-		cancel, err := pub.Subscribe(agentapi.WatchWorkspaceAgentMetadataChannel(agent.ID), func(ctx context.Context, message []byte) {
-			if atomic.AddInt64(&eventCount, 1) > 1 {
-				return
-			}
-			require.NoError(t, json.Unmarshal(message, &gotEvent))
-		})
-		require.NoError(t, err)
-		defer cancel()
-
 		resp, err := api.BatchUpdateMetadata(context.Background(), req)
+		// Should return error because keys are too long.
 		require.Error(t, err)
-		require.Equal(t, "metadata keys of 6145 bytes exceeded 6144 bytes", err.Error())
 		require.Nil(t, resp)
-
-		require.Equal(t, int64(1), atomic.LoadInt64(&eventCount))
-		require.Equal(t, agentapi.WorkspaceAgentMetadataChannelPayload{
-			CollectedAt: now,
-			// No key 4.
-			Keys: []string{req.Metadata[0].Key, req.Metadata[1].Key, req.Metadata[2].Key},
-		}, gotEvent)
-	})
-
-	// Test RBAC fast path with valid RBAC object - should NOT call GetWorkspaceByAgentID
-	// This test verifies that when a valid RBAC object is present in context, the dbauthz layer
-	// uses the fast path and skips the GetWorkspaceByAgentID database call.
-	t.Run("WorkspaceCached_SkipsDBCall", func(t *testing.T) {
-		t.Parallel()
-
-		var (
-			ctrl = gomock.NewController(t)
-			dbM  = dbmock.NewMockStore(ctrl)
-			pub  = &fakePublisher{}
-			now  = dbtime.Now()
-			// Set up consistent IDs that represent a valid workspace->agent relationship
-			workspaceID = uuid.MustParse("12345678-1234-1234-1234-123456789012")
-			templateID  = uuid.MustParse("aaaabbbb-cccc-dddd-eeee-ffffffff0000")
-			ownerID     = uuid.MustParse("87654321-4321-4321-4321-210987654321")
-			orgID       = uuid.MustParse("11111111-1111-1111-1111-111111111111")
-			agentID     = uuid.MustParse("aaaaaaaa-aaaa-aaaa-aaaa-aaaaaaaaaaaa")
-		)
-
-		agent := database.WorkspaceAgent{
-			ID: agentID,
-			// In a real scenario, this agent would belong to a resource in the workspace above
-		}
-
-		req := &agentproto.BatchUpdateMetadataRequest{
-			Metadata: []*agentproto.Metadata{
-				{
-					Key: "test_key",
-					Result: &agentproto.WorkspaceAgentMetadata_Result{
-						CollectedAt: timestamppb.New(now.Add(-time.Second)),
-						Age:         1,
-						Value:       "test_value",
-					},
-				},
-			},
-		}
-
-		// Expect UpdateWorkspaceAgentMetadata to be called
-		dbM.EXPECT().UpdateWorkspaceAgentMetadata(gomock.Any(), database.UpdateWorkspaceAgentMetadataParams{
-			WorkspaceAgentID: agent.ID,
-			Key:              []string{"test_key"},
-			Value:            []string{"test_value"},
-			Error:            []string{""},
-			CollectedAt:      []time.Time{now},
-		}).Return(nil)
-
-		// DO NOT expect GetWorkspaceByAgentID - the fast path should skip this call
-		// If GetWorkspaceByAgentID is called, the test will fail with "unexpected call"
-
-		// dbauthz will call Wrappers() to check for wrapped databases
-		dbM.EXPECT().Wrappers().Return([]string{}).AnyTimes()
-
-		// Set up dbauthz to test the actual authorization layer
-		auth := rbac.NewStrictCachingAuthorizer(prometheus.NewRegistry())
-		accessControlStore := &atomic.Pointer[dbauthz.AccessControlStore]{}
-		var acs dbauthz.AccessControlStore = dbauthz.AGPLTemplateAccessControlStore{}
-		accessControlStore.Store(&acs)
-
-		api := &agentapi.MetadataAPI{
-			AgentFn: func(_ context.Context) (database.WorkspaceAgent, error) {
-				return agent, nil
-			},
-			Workspace: &agentapi.CachedWorkspaceFields{},
-			Database:  dbauthz.New(dbM, auth, testutil.Logger(t), accessControlStore),
-			Pubsub:    pub,
-			Log:       testutil.Logger(t),
-			TimeNowFn: func() time.Time {
-				return now
-			},
-		}
-
-		api.Workspace.UpdateValues(database.Workspace{
-			ID:             workspaceID,
-			OwnerID:        ownerID,
-			OrganizationID: orgID,
-		})
-
-		// Create roles with workspace permissions
-		userRoles := rbac.Roles([]rbac.Role{
-			{
-				Identifier: rbac.RoleMember(),
-				User: []rbac.Permission{
-					{
-						Negate:       false,
-						ResourceType: rbac.ResourceWorkspace.Type,
-						Action:       policy.WildcardSymbol,
-					},
-				},
-				ByOrgID: map[string]rbac.OrgPermissions{
-					orgID.String(): {
-						Member: []rbac.Permission{
-							{
-								Negate:       false,
-								ResourceType: rbac.ResourceWorkspace.Type,
-								Action:       policy.WildcardSymbol,
-							},
-						},
-					},
-				},
-			},
-		})
-
-		agentScope := rbac.WorkspaceAgentScope(rbac.WorkspaceAgentScopeParams{
-			WorkspaceID: workspaceID,
-			OwnerID:     ownerID,
-			TemplateID:  templateID,
-			VersionID:   uuid.New(),
-		})
-
-		ctx := dbauthz.As(context.Background(), rbac.Subject{
-			Type:         rbac.SubjectTypeUser,
-			FriendlyName: "testuser",
-			Email:        "testuser@example.com",
-			ID:           ownerID.String(),
-			Roles:        userRoles,
-			Groups:       []string{orgID.String()},
-			Scope:        agentScope,
-		}.WithCachedASTValue())
-
-		resp, err := api.BatchUpdateMetadata(ctx, req)
-		require.NoError(t, err)
-		require.NotNil(t, resp)
-	})
-	// Test RBAC slow path - invalid RBAC object should fall back to GetWorkspaceByAgentID
-	// This test verifies that when the RBAC object has invalid IDs (nil UUIDs), the dbauthz layer
-	// falls back to the slow path and calls GetWorkspaceByAgentID.
-	t.Run("InvalidWorkspaceCached_RequiresDBCall", func(t *testing.T) {
-		t.Parallel()
-
-		var (
-			ctrl        = gomock.NewController(t)
-			dbM         = dbmock.NewMockStore(ctrl)
-			pub         = &fakePublisher{}
-			now         = dbtime.Now()
-			workspaceID = uuid.MustParse("12345678-1234-1234-1234-123456789012")
-			templateID  = uuid.MustParse("aaaabbbb-cccc-dddd-eeee-ffffffff0000")
-			ownerID     = uuid.MustParse("87654321-4321-4321-4321-210987654321")
-			orgID       = uuid.MustParse("11111111-1111-1111-1111-111111111111")
-			agentID     = uuid.MustParse("bbbbbbbb-bbbb-bbbb-bbbb-bbbbbbbbbbbb")
-		)
-
-		agent := database.WorkspaceAgent{
-			ID: agentID,
-		}
-
-		req := &agentproto.BatchUpdateMetadataRequest{
-			Metadata: []*agentproto.Metadata{
-				{
-					Key: "test_key",
-					Result: &agentproto.WorkspaceAgentMetadata_Result{
-						CollectedAt: timestamppb.New(now.Add(-time.Second)),
-						Age:         1,
-						Value:       "test_value",
-					},
-				},
-			},
-		}
-
-		// EXPECT GetWorkspaceByAgentID to be called because the RBAC fast path validation fails
-		dbM.EXPECT().GetWorkspaceByAgentID(gomock.Any(), agentID).Return(database.Workspace{
-			ID:             workspaceID,
-			OwnerID:        ownerID,
-			OrganizationID: orgID,
-		}, nil)
-
-		// Expect UpdateWorkspaceAgentMetadata to be called after authorization
-		dbM.EXPECT().UpdateWorkspaceAgentMetadata(gomock.Any(), database.UpdateWorkspaceAgentMetadataParams{
-			WorkspaceAgentID: agent.ID,
-			Key:              []string{"test_key"},
-			Value:            []string{"test_value"},
-			Error:            []string{""},
-			CollectedAt:      []time.Time{now},
-		}).Return(nil)
-
-		// dbauthz will call Wrappers() to check for wrapped databases
-		dbM.EXPECT().Wrappers().Return([]string{}).AnyTimes()
-
-		// Set up dbauthz to test the actual authorization layer
-		auth := rbac.NewStrictCachingAuthorizer(prometheus.NewRegistry())
-		accessControlStore := &atomic.Pointer[dbauthz.AccessControlStore]{}
-		var acs dbauthz.AccessControlStore = dbauthz.AGPLTemplateAccessControlStore{}
-		accessControlStore.Store(&acs)
-
-		api := &agentapi.MetadataAPI{
-			AgentFn: func(_ context.Context) (database.WorkspaceAgent, error) {
-				return agent, nil
-			},
-
-			Workspace: &agentapi.CachedWorkspaceFields{},
-			Database:  dbauthz.New(dbM, auth, testutil.Logger(t), accessControlStore),
-			Pubsub:    pub,
-			Log:       testutil.Logger(t),
-			TimeNowFn: func() time.Time {
-				return now
-			},
-		}
-
-		// Create an invalid RBAC object with nil UUIDs for owner/org
-		// This will fail dbauthz fast path validation and trigger GetWorkspaceByAgentID
-		api.Workspace.UpdateValues(database.Workspace{
-			ID:             uuid.MustParse("cccccccc-cccc-cccc-cccc-cccccccccccc"),
-			OwnerID:        uuid.Nil, // Invalid: fails dbauthz fast path validation
-			OrganizationID: uuid.Nil, // Invalid: fails dbauthz fast path validation
-		})
-
-		// Create roles with workspace permissions
-		userRoles := rbac.Roles([]rbac.Role{
-			{
-				Identifier: rbac.RoleMember(),
-				User: []rbac.Permission{
-					{
-						Negate:       false,
-						ResourceType: rbac.ResourceWorkspace.Type,
-						Action:       policy.WildcardSymbol,
-					},
-				},
-				ByOrgID: map[string]rbac.OrgPermissions{
-					orgID.String(): {
-						Member: []rbac.Permission{
-							{
-								Negate:       false,
-								ResourceType: rbac.ResourceWorkspace.Type,
-								Action:       policy.WildcardSymbol,
-							},
-						},
-					},
-				},
-			},
-		})
-
-		agentScope := rbac.WorkspaceAgentScope(rbac.WorkspaceAgentScopeParams{
-			WorkspaceID: workspaceID,
-			OwnerID:     ownerID,
-			TemplateID:  templateID,
-			VersionID:   uuid.New(),
-		})
-
-		ctx := dbauthz.As(context.Background(), rbac.Subject{
-			Type:         rbac.SubjectTypeUser,
-			FriendlyName: "testuser",
-			Email:        "testuser@example.com",
-			ID:           ownerID.String(),
-			Roles:        userRoles,
-			Groups:       []string{orgID.String()},
-			Scope:        agentScope,
-		}.WithCachedASTValue())
-
-		resp, err := api.BatchUpdateMetadata(ctx, req)
-		require.NoError(t, err)
-		require.NotNil(t, resp)
-	})
-
-	// Test RBAC slow path - no RBAC object in context
-	// This test verifies that when no RBAC object is present in context, the dbauthz layer
-	// falls back to the slow path and calls GetWorkspaceByAgentID.
-	t.Run("WorkspaceNotCached_RequiresDBCall", func(t *testing.T) {
-		t.Parallel()
-
-		var (
-			ctrl        = gomock.NewController(t)
-			dbM         = dbmock.NewMockStore(ctrl)
-			pub         = &fakePublisher{}
-			now         = dbtime.Now()
-			workspaceID = uuid.MustParse("12345678-1234-1234-1234-123456789012")
-			templateID  = uuid.MustParse("aaaabbbb-cccc-dddd-eeee-ffffffff0000")
-			ownerID     = uuid.MustParse("87654321-4321-4321-4321-210987654321")
-			orgID       = uuid.MustParse("11111111-1111-1111-1111-111111111111")
-			agentID     = uuid.MustParse("dddddddd-dddd-dddd-dddd-dddddddddddd")
-		)
-
-		agent := database.WorkspaceAgent{
-			ID: agentID,
-		}
-
-		req := &agentproto.BatchUpdateMetadataRequest{
-			Metadata: []*agentproto.Metadata{
-				{
-					Key: "test_key",
-					Result: &agentproto.WorkspaceAgentMetadata_Result{
-						CollectedAt: timestamppb.New(now.Add(-time.Second)),
-						Age:         1,
-						Value:       "test_value",
-					},
-				},
-			},
-		}
-
-		// EXPECT GetWorkspaceByAgentID to be called because no RBAC object is in context
-		dbM.EXPECT().GetWorkspaceByAgentID(gomock.Any(), agentID).Return(database.Workspace{
-			ID:             workspaceID,
-			OwnerID:        ownerID,
-			OrganizationID: orgID,
-		}, nil)
-
-		// Expect UpdateWorkspaceAgentMetadata to be called after authorization
-		dbM.EXPECT().UpdateWorkspaceAgentMetadata(gomock.Any(), database.UpdateWorkspaceAgentMetadataParams{
-			WorkspaceAgentID: agent.ID,
-			Key:              []string{"test_key"},
-			Value:            []string{"test_value"},
-			Error:            []string{""},
-			CollectedAt:      []time.Time{now},
-		}).Return(nil)
-
-		// dbauthz will call Wrappers() to check for wrapped databases
-		dbM.EXPECT().Wrappers().Return([]string{}).AnyTimes()
-
-		// Set up dbauthz to test the actual authorization layer
-		auth := rbac.NewStrictCachingAuthorizer(prometheus.NewRegistry())
-		accessControlStore := &atomic.Pointer[dbauthz.AccessControlStore]{}
-		var acs dbauthz.AccessControlStore = dbauthz.AGPLTemplateAccessControlStore{}
-		accessControlStore.Store(&acs)
-
-		api := &agentapi.MetadataAPI{
-			AgentFn: func(_ context.Context) (database.WorkspaceAgent, error) {
-				return agent, nil
-			},
-			Workspace: &agentapi.CachedWorkspaceFields{},
-			Database:  dbauthz.New(dbM, auth, testutil.Logger(t), accessControlStore),
-			Pubsub:    pub,
-			Log:       testutil.Logger(t),
-			TimeNowFn: func() time.Time {
-				return now
-			},
-		}
-
-		// Create roles with workspace permissions
-		userRoles := rbac.Roles([]rbac.Role{
-			{
-				Identifier: rbac.RoleMember(),
-				User: []rbac.Permission{
-					{
-						Negate:       false,
-						ResourceType: rbac.ResourceWorkspace.Type,
-						Action:       policy.WildcardSymbol,
-					},
-				},
-				ByOrgID: map[string]rbac.OrgPermissions{
-					orgID.String(): {
-						Member: []rbac.Permission{
-							{
-								Negate:       false,
-								ResourceType: rbac.ResourceWorkspace.Type,
-								Action:       policy.WildcardSymbol,
-							},
-						},
-					},
-				},
-			},
-		})
-
-		agentScope := rbac.WorkspaceAgentScope(rbac.WorkspaceAgentScopeParams{
-			WorkspaceID: workspaceID,
-			OwnerID:     ownerID,
-			TemplateID:  templateID,
-			VersionID:   uuid.New(),
-		})
-
-		ctx := dbauthz.As(context.Background(), rbac.Subject{
-			Type:         rbac.SubjectTypeUser,
-			FriendlyName: "testuser",
-			Email:        "testuser@example.com",
-			ID:           ownerID.String(),
-			Roles:        userRoles,
-			Groups:       []string{orgID.String()},
-			Scope:        agentScope,
-		}.WithCachedASTValue())
-
-		resp, err := api.BatchUpdateMetadata(ctx, req)
-		require.NoError(t, err)
-		require.NotNil(t, resp)
-	})
-
-	// Test cache refresh - AutostartSchedule updated
-	// This test verifies that the cache refresh mechanism actually calls GetWorkspaceByID
-	// and updates the cached workspace fields when the workspace is modified (e.g., autostart schedule changes).
-	t.Run("CacheRefreshed_AutostartScheduleUpdated", func(t *testing.T) {
-		t.Parallel()
-
-		var (
-			ctrl       = gomock.NewController(t)
-			dbM        = dbmock.NewMockStore(ctrl)
-			pub        = &fakePublisher{}
-			now        = dbtime.Now()
-			mClock     = quartz.NewMock(t)
-			tickerTrap = mClock.Trap().TickerFunc("cache_refresh")
-
-			workspaceID = uuid.MustParse("12345678-1234-1234-1234-123456789012")
-			ownerID     = uuid.MustParse("87654321-4321-4321-4321-210987654321")
-			orgID       = uuid.MustParse("11111111-1111-1111-1111-111111111111")
-			templateID  = uuid.MustParse("aaaabbbb-cccc-dddd-eeee-ffffffff0000")
-			agentID     = uuid.MustParse("ffffffff-ffff-ffff-ffff-ffffffffffff")
-		)
-
-		agent := database.WorkspaceAgent{
-			ID: agentID,
-		}
-
-		// Initial workspace - has Monday-Friday 9am autostart
-		initialWorkspace := database.Workspace{
-			ID:                workspaceID,
-			OwnerID:           ownerID,
-			OrganizationID:    orgID,
-			TemplateID:        templateID,
-			Name:              "my-workspace",
-			OwnerUsername:     "testuser",
-			TemplateName:      "test-template",
-			AutostartSchedule: sql.NullString{Valid: true, String: "CRON_TZ=UTC 0 9 * * 1-5"},
-		}
-
-		// Updated workspace - user changed autostart to 5pm and renamed workspace
-		updatedWorkspace := database.Workspace{
-			ID:                workspaceID,
-			OwnerID:           ownerID,
-			OrganizationID:    orgID,
-			TemplateID:        templateID,
-			Name:              "my-workspace-renamed", // Changed!
-			OwnerUsername:     "testuser",
-			TemplateName:      "test-template",
-			AutostartSchedule: sql.NullString{Valid: true, String: "CRON_TZ=UTC 0 17 * * 1-5"}, // Changed!
-			DormantAt:         sql.NullTime{},
-		}
-
-		req := &agentproto.BatchUpdateMetadataRequest{
-			Metadata: []*agentproto.Metadata{
-				{
-					Key: "test_key",
-					Result: &agentproto.WorkspaceAgentMetadata_Result{
-						CollectedAt: timestamppb.New(now.Add(-time.Second)),
-						Age:         1,
-						Value:       "test_value",
-					},
-				},
-			},
-		}
-
-		// EXPECT GetWorkspaceByID to be called during cache refresh
-		// This is the key assertion - proves the refresh mechanism is working
-		dbM.EXPECT().GetWorkspaceByID(gomock.Any(), workspaceID).Return(updatedWorkspace, nil)
-
-		// API needs to fetch the agent when calling metadata update
-		dbM.EXPECT().GetWorkspaceAgentByID(gomock.Any(), agentID).Return(agent, nil)
-
-		// After refresh, metadata update should work with updated cache
-		dbM.EXPECT().UpdateWorkspaceAgentMetadata(gomock.Any(), gomock.Any()).DoAndReturn(
-			func(ctx context.Context, params database.UpdateWorkspaceAgentMetadataParams) error {
-				require.Equal(t, agent.ID, params.WorkspaceAgentID)
-				require.Equal(t, []string{"test_key"}, params.Key)
-				require.Equal(t, []string{"test_value"}, params.Value)
-				require.Equal(t, []string{""}, params.Error)
-				require.Len(t, params.CollectedAt, 1)
-				return nil
-			},
-		).AnyTimes()
-
-		// May call GetWorkspaceByAgentID if slow path is used before refresh
-		dbM.EXPECT().GetWorkspaceByAgentID(gomock.Any(), agentID).Return(updatedWorkspace, nil).AnyTimes()
-
-		// dbauthz will call Wrappers()
-		dbM.EXPECT().Wrappers().Return([]string{}).AnyTimes()
-
-		// Set up dbauthz
-		auth := rbac.NewStrictCachingAuthorizer(prometheus.NewRegistry())
-		accessControlStore := &atomic.Pointer[dbauthz.AccessControlStore]{}
-		var acs dbauthz.AccessControlStore = dbauthz.AGPLTemplateAccessControlStore{}
-		accessControlStore.Store(&acs)
-
-		ctx, cancel := context.WithCancel(context.Background())
-		defer cancel()
-
-		// Create roles with workspace permissions
-		userRoles := rbac.Roles([]rbac.Role{
-			{
-				Identifier: rbac.RoleMember(),
-				User: []rbac.Permission{
-					{
-						Negate:       false,
-						ResourceType: rbac.ResourceWorkspace.Type,
-						Action:       policy.WildcardSymbol,
-					},
-				},
-				ByOrgID: map[string]rbac.OrgPermissions{
-					orgID.String(): {
-						Member: []rbac.Permission{
-							{
-								Negate:       false,
-								ResourceType: rbac.ResourceWorkspace.Type,
-								Action:       policy.WildcardSymbol,
-							},
-						},
-					},
-				},
-			},
-		})
-
-		agentScope := rbac.WorkspaceAgentScope(rbac.WorkspaceAgentScopeParams{
-			WorkspaceID: workspaceID,
-			OwnerID:     ownerID,
-			TemplateID:  templateID,
-			VersionID:   uuid.New(),
-		})
-
-		ctxWithActor := dbauthz.As(ctx, rbac.Subject{
-			Type:         rbac.SubjectTypeUser,
-			FriendlyName: "testuser",
-			Email:        "testuser@example.com",
-			ID:           ownerID.String(),
-			Roles:        userRoles,
-			Groups:       []string{orgID.String()},
-			Scope:        agentScope,
-		}.WithCachedASTValue())
-
-		// Create full API with cached workspace fields (initial state)
-		api := agentapi.New(agentapi.Options{
-			AuthenticatedCtx: ctxWithActor,
-			AgentID:          agentID,
-			WorkspaceID:      workspaceID,
-			OwnerID:          ownerID,
-			OrganizationID:   orgID,
-			Database:         dbauthz.New(dbM, auth, testutil.Logger(t), accessControlStore),
-			Log:              testutil.Logger(t),
-			Clock:            mClock,
-			Pubsub:           pub,
-		}, initialWorkspace) // Cache is initialized with 9am schedule and "my-workspace" name
-
-		// Wait for ticker to be set up and release it so it can fire
-		tickerTrap.MustWait(ctx).MustRelease(ctx)
-		tickerTrap.Close()
-
-		// Advance clock to trigger cache refresh and wait for it to complete
-		_, aw := mClock.AdvanceNext()
-		aw.MustWait(ctx)
-
-		// At this point, GetWorkspaceByID should have been called and cache updated
-		// The cache now has the 5pm schedule and "my-workspace-renamed" name
-
-		// Now call metadata update to verify the refreshed cache works
-		resp, err := api.MetadataAPI.BatchUpdateMetadata(ctxWithActor, req)
-		require.NoError(t, err)
-		require.NotNil(t, resp)
+		testutil.Eventually(ctx, t, func(ctx context.Context) bool {
+			return prom_testutil.ToFloat64(batcher.Metrics.MetadataTotal) == 3.0
+		}, testutil.IntervalFast)
 	})
 }
@@ -0,0 +1,59 @@
+package metadatabatcher
+
+import (
+	"encoding/base64"
+
+	"github.com/google/uuid"
+	"golang.org/x/xerrors"
+)
+
+const (
+	// uuidBase64Size is the size of a base64-encoded UUID without padding (22 characters).
+	UUIDBase64Size = 22
+
+	// maxAgentIDsPerChunk is the maximum number of agent IDs that can fit in a
+	// single pubsub message. PostgreSQL NOTIFY has an 8KB limit.
+	// With base64 encoding, each UUID is 22 characters, so we can fit
+	// ~363 agent IDs per chunk (8000 / 22 = 363.6).
+	maxAgentIDsPerChunk = maxPubsubPayloadSize / UUIDBase64Size
+)
+
+func EncodeAgentID(agentID uuid.UUID, dst []byte) error {
+	// Encode UUID bytes to base64 without padding (RawStdEncoding).
+	// This produces exactly 22 characters per UUID.
+	reqLen := base64.RawStdEncoding.EncodedLen(len(agentID))
+	if len(dst) < reqLen {
+		return xerrors.Errorf("destination byte slice was too small %d, required %d", len(dst), reqLen)
+	}
+	base64.RawStdEncoding.Encode(dst, agentID[:])
+	return nil
+}
+
+// EncodeAgentIDChunks encodes agent IDs into chunks that fit within the
+// PostgreSQL NOTIFY 8KB payload size limit. Each UUID is base64-encoded
+// (without padding) and concatenated into a single byte slice per chunk.
+func EncodeAgentIDChunks(agentIDs []uuid.UUID) ([][]byte, error) {
+	chunks := make([][]byte, 0, (len(agentIDs)+maxAgentIDsPerChunk-1)/maxAgentIDsPerChunk)
+
+	for i := 0; i < len(agentIDs); i += maxAgentIDsPerChunk {
+		end := i + maxAgentIDsPerChunk
+		if end > len(agentIDs) {
+			end = len(agentIDs)
+		}
+
+		chunk := agentIDs[i:end]
+
+		// Build payload by base64-encoding each UUID (without padding) and
+		// concatenating them. This is UTF-8 safe for PostgreSQL NOTIFY.
+		payload := make([]byte, len(chunk)*UUIDBase64Size)
+		for i, agentID := range chunk {
+			err := EncodeAgentID(agentID, payload[i*UUIDBase64Size:(i+1)*UUIDBase64Size])
+			if err != nil {
+				return nil, err
+			}
+		}
+		chunks = append(chunks, payload)
+	}
+
+	return chunks, nil
+}
@@ -0,0 +1,122 @@
+package metadatabatcher_test
+
+import (
+	"encoding/base64"
+	"testing"
+
+	"github.com/google/uuid"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/coderd/agentapi/metadatabatcher"
+)
+
+func TestEncodeDecodeRoundTrip(t *testing.T) {
+	t.Parallel()
+
+	tests := []struct {
+		name     string
+		agentIDs []uuid.UUID
+	}{
+		{
+			name:     "Empty",
+			agentIDs: []uuid.UUID{},
+		},
+		{
+			name:     "Single",
+			agentIDs: []uuid.UUID{uuid.New()},
+		},
+		{
+			name: "Multiple",
+			agentIDs: []uuid.UUID{
+				uuid.New(),
+				uuid.New(),
+				uuid.New(),
+			},
+		},
+		{
+			name: "Exactly 363 (one chunk)",
+			agentIDs: func() []uuid.UUID {
+				ids := make([]uuid.UUID, 363)
+				for i := range ids {
+					ids[i] = uuid.New()
+				}
+				return ids
+			}(),
+		},
+		{
+			name: "364 (two chunks)",
+			agentIDs: func() []uuid.UUID {
+				ids := make([]uuid.UUID, 364)
+				for i := range ids {
+					ids[i] = uuid.New()
+				}
+				return ids
+			}(),
+		},
+		{
+			name: "600 (multiple chunks)",
+			agentIDs: func() []uuid.UUID {
+				ids := make([]uuid.UUID, 600)
+				for i := range ids {
+					ids[i] = uuid.New()
+				}
+				return ids
+			}(),
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			t.Parallel()
+
+			// Encode the agent IDs into chunks.
+			chunks, err := metadatabatcher.EncodeAgentIDChunks(tt.agentIDs)
+			require.NoError(t, err)
+
+			// Decode all chunks and collect the agent IDs.
+			var decoded []uuid.UUID
+			for _, chunk := range chunks {
+				for i := 0; i < len(chunk); i += metadatabatcher.UUIDBase64Size {
+					var u uuid.UUID
+					_, err := base64.RawStdEncoding.Decode(u[:], chunk[i:i+metadatabatcher.UUIDBase64Size])
+					require.NoError(t, err)
+					decoded = append(decoded, u)
+				}
+			}
+
+			// Verify we got the same agent IDs back.
+			if len(tt.agentIDs) == 0 {
+				require.Empty(t, decoded)
+			} else {
+				require.Equal(t, tt.agentIDs, decoded)
+			}
+		})
+	}
+}
+
+// TestEncodeAgentIDChunks_PGPubsubSize ensures that each pubsub message generated via EncodeAgentIDChunks fits within
+// the max allowed 8kb by Postgres.
+func TestEncodeAgentIDChunks_PGPubsubSize(t *testing.T) {
+	t.Parallel()
+
+	// Create 600 agents (should split into 2 chunks: 363 + 237).
+	agentIDs := make([]uuid.UUID, 600)
+	for i := range agentIDs {
+		agentIDs[i] = uuid.New()
+	}
+
+	chunks, err := metadatabatcher.EncodeAgentIDChunks(agentIDs)
+	require.NoError(t, err)
+	require.Len(t, chunks, 2)
+
+	// First chunk should have 363 IDs (363 * 22 = 7986 bytes).
+	require.Equal(t, 363*22, len(chunks[0]))
+
+	// Second chunk should have 237 IDs (237 * 22 = 5214 bytes).
+	require.Equal(t, 237*22, len(chunks[1]))
+
+	// Each chunk should be under 8KB.
+	for i, chunk := range chunks {
+		require.LessOrEqual(t, len(chunk), 8000, "chunk %d exceeds 8KB limit", i)
+	}
+}
@@ -0,0 +1,398 @@
+package metadatabatcher
+
+import (
+	"context"
+	"sync/atomic"
+	"time"
+
+	"github.com/google/uuid"
+	"github.com/prometheus/client_golang/prometheus"
+	"golang.org/x/xerrors"
+
+	"cdr.dev/slog/v3"
+	"github.com/coder/coder/v2/coderd/database"
+	"github.com/coder/coder/v2/coderd/database/dbauthz"
+	"github.com/coder/coder/v2/coderd/database/pubsub"
+	"github.com/coder/quartz"
+)
+
+const (
+	// defaultMetadataBatchSize is the maximum number of metadata entries
+	// (key-value pairs across all agents) to batch before forcing a flush.
+	// With typical agents having 5-15 metadata keys, this accommodates
+	// 30-100 agents per batch.
+	defaultMetadataBatchSize = 500
+
+	// defaultChannelBufferMultiplier is the multiplier for the channel buffer size
+	// relative to the batch size. A 5x multiplier provides significant headroom
+	// for bursts while the batch is being flushed.
+	defaultChannelBufferMultiplier = 5
+
+	// defaultMetadataFlushInterval is how frequently to flush batched metadata
+	// updates to the database and pubsub. 5 seconds provides a good balance
+	// between reducing database load and maintaining reasonable UI update
+	// latency.
+	defaultMetadataFlushInterval = 5 * time.Second
+
+	// maxPubsubPayloadSize is the maximum size of a single pubsub message.
+	// PostgreSQL NOTIFY has an 8KB limit for the payload.
+	maxPubsubPayloadSize = 8000 // Leave some headroom below 8192 bytes
+
+	// Timeout to use for the context created when flushing the final batch due to the top level context being 'Done'
+	finalFlushTimeout = 15 * time.Second
+
+	// Channel to publish batch metadata updates to, each update contains a list of all Agent IDs that have an update in
+	// the most recent batch
+	MetadataBatchPubsubChannel = "workspace_agent_metadata_batch"
+
+	// flush reasons
+	flushCapacity = "capacity"
+	flushTicker   = "scheduled"
+	flushExit     = "shutdown"
+)
+
+// compositeKey uniquely identifies a metadata entry by agent ID and key name.
+type compositeKey struct {
+	agentID uuid.UUID
+	key     string
+}
+
+// value holds a single metadata key-value pair with its error state
+// and collection timestamp.
+type value struct {
+	v           string
+	error       string
+	collectedAt time.Time
+}
+
+// update represents a single metadata update to be batched.
+type update struct {
+	compositeKey
+	value
+}
+
+// Batcher holds a buffer of agent metadata updates and periodically
+// flushes them to the database and pubsub. This reduces database write
+// frequency and pubsub publish rate.
+type Batcher struct {
+	store database.Store
+	ps    pubsub.Pubsub
+	log   slog.Logger
+
+	// updateCh is the buffered channel that receives metadata updates from Add() calls.
+	updateCh chan update
+
+	// batch holds the current batch being accumulated. For updates with the same composite key the most recent value wins.
+	batch           map[compositeKey]value
+	currentBatchLen atomic.Int64
+	maxBatchSize    int
+
+	clock    quartz.Clock
+	timer    *quartz.Timer
+	interval time.Duration
+	// Used to only log at warn level for dropped keys infrequently, as it could be noisy in failure scenarios.
+	warnTicker *quartz.Ticker
+
+	// ctx is the context for the batcher. Used to check if shutdown has begun.
+	ctx    context.Context
+	cancel context.CancelFunc
+	done   chan struct{}
+
+	// Metrics collects Prometheus metrics for the batcher.
+	Metrics Metrics
+}
+
+// Option is a functional option for configuring a Batcher.
+type Option func(b *Batcher)
+
+func WithBatchSize(size int) Option {
+	return func(b *Batcher) {
+		b.maxBatchSize = size
+	}
+}
+
+func WithInterval(d time.Duration) Option {
+	return func(b *Batcher) {
+		b.interval = d
+	}
+}
+
+func WithLogger(log slog.Logger) Option {
+	return func(b *Batcher) {
+		b.log = log
+	}
+}
+
+func WithClock(clock quartz.Clock) Option {
+	return func(b *Batcher) {
+		b.clock = clock
+	}
+}
+
+// NewBatcher creates a new Batcher and starts it. Here ctx controls the lifetime of the batcher, canceling it will
+// result in the Batcher exiting it's processing routine (run).
+func NewBatcher(ctx context.Context, reg prometheus.Registerer, store database.Store, ps pubsub.Pubsub, opts ...Option) (*Batcher, error) {
+	b := &Batcher{
+		store:   store,
+		ps:      ps,
+		Metrics: NewMetrics(),
+		done:    make(chan struct{}),
+		log:     slog.Logger{},
+		clock:   quartz.NewReal(),
+	}
+
+	for _, opt := range opts {
+		opt(b)
+	}
+
+	b.Metrics.register(reg)
+
+	if b.interval == 0 {
+		b.interval = defaultMetadataFlushInterval
+	}
+
+	if b.maxBatchSize == 0 {
+		b.maxBatchSize = defaultMetadataBatchSize
+	}
+
+	// Create warn ticker after options are applied so it uses the correct clock.
+	b.warnTicker = b.clock.NewTicker(10 * time.Second)
+
+	if b.timer == nil {
+		b.timer = b.clock.NewTimer(b.interval)
+	}
+
+	// Create buffered channel with 5x batch size capacity
+	channelSize := b.maxBatchSize * defaultChannelBufferMultiplier
+	b.updateCh = make(chan update, channelSize)
+
+	// Initialize batch map
+	b.batch = make(map[compositeKey]value)
+
+	b.ctx, b.cancel = context.WithCancel(ctx)
+	go func() {
+		b.run(b.ctx)
+		close(b.done)
+	}()
+
+	return b, nil
+}
+
+func (b *Batcher) Close() {
+	b.cancel()
+	if b.timer != nil {
+		b.timer.Stop()
+	}
+	// Wait for the run function to end, it may be sending one last batch.
+	<-b.done
+}
+
+// Add adds metadata updates for an agent to the batcher by writing to a
+// buffered channel. If the channel is full, updates are dropped. Updates
+// to the same metadata key for the same agent are deduplicated in the batch,
+// keeping only the value with the most recent collectedAt timestamp.
+func (b *Batcher) Add(agentID uuid.UUID, keys []string, values []string, errors []string, collectedAt []time.Time) error {
+	if !(len(keys) == len(values) && len(values) == len(errors) && len(errors) == len(collectedAt)) {
+		return xerrors.Errorf("invalid Add call, all inputs must have the same number of items; keys: %d, values: %d, errors: %d, collectedAt: %d", len(keys), len(values), len(errors), len(collectedAt))
+	}
+
+	// Write each update to the channel. If the channel is full, drop the update.
+	var u update
+	droppedCount := 0
+	for i := range keys {
+		u.agentID = agentID
+		u.key = keys[i]
+		u.v = values[i]
+		u.error = errors[i]
+		u.collectedAt = collectedAt[i]
+
+		select {
+		case b.updateCh <- u:
+			// Successfully queued
+		default:
+			// Channel is full, drop this update
+			droppedCount++
+		}
+	}
+
+	// Log dropped keys if any were dropped.
+	if droppedCount > 0 {
+		msg := "metadata channel at capacity, dropped updates"
+		fields := []slog.Field{
+			slog.F("agent_id", agentID),
+			slog.F("channel_size", cap(b.updateCh)),
+			slog.F("dropped_count", droppedCount),
+		}
+		select {
+		case <-b.warnTicker.C:
+			b.log.Warn(context.Background(), msg, fields...)
+		default:
+			b.log.Debug(context.Background(), msg, fields...)
+		}
+
+		b.Metrics.DroppedKeysTotal.Add(float64(droppedCount))
+	}
+
+	return nil
+}
+
+// processUpdate adds a metadata update to the batch with deduplication based on timestamp.
+func (b *Batcher) processUpdate(update update) {
+	ck := compositeKey{
+		agentID: update.agentID,
+		key:     update.key,
+	}
+
+	// Check if key already exists and only update if new value is newer.
+	existing, exists := b.batch[ck]
+	if exists && update.collectedAt.Before(existing.collectedAt) {
+		return
+	}
+
+	b.batch[ck] = value{
+		v:           update.v,
+		error:       update.error,
+		collectedAt: update.collectedAt,
+	}
+	if !exists {
+		b.currentBatchLen.Add(1)
+	}
+}
+
+// run runs the batcher loop, reading from the update channel and flushing
+// periodically or when the batch reaches capacity.
+func (b *Batcher) run(ctx context.Context) {
+	// nolint:gocritic // This is only ever used for one thing - updating agent metadata.
+	authCtx := dbauthz.AsSystemRestricted(ctx)
+	for {
+		select {
+		case update := <-b.updateCh:
+			b.processUpdate(update)
+
+			// Check if batch has reached capacity
+			if int(b.currentBatchLen.Load()) >= b.maxBatchSize {
+				b.flush(authCtx, flushCapacity)
+				// Reset timer so the next scheduled flush is interval duration
+				// from now, not from when it was originally scheduled.
+				b.timer.Reset(b.interval, "metadataBatcher", "capacityFlush")
+			}
+
+		case <-b.timer.C:
+			b.flush(authCtx, flushTicker)
+			// Reset timer to schedule the next flush.
+			b.timer.Reset(b.interval, "metadataBatcher", "scheduledFlush")
+
+		case <-ctx.Done():
+			b.log.Debug(ctx, "context done, flushing before exit")
+
+			// We must create a new context here as the parent context is done.
+			ctxTimeout, cancel := context.WithTimeout(context.Background(), finalFlushTimeout)
+			defer cancel() //nolint:revive // We're returning, defer is fine.
+
+			// nolint:gocritic // This is only ever used for one thing - updating agent metadata.
+			b.flush(dbauthz.AsSystemRestricted(ctxTimeout), flushExit)
+			return
+		}
+	}
+}
+
+// flush flushes the current batch to the database and pubsub.
+func (b *Batcher) flush(ctx context.Context, reason string) {
+	count := len(b.batch)
+
+	if count == 0 {
+		return
+	}
+
+	start := b.clock.Now()
+	b.log.Debug(ctx, "flushing metadata batch",
+		slog.F("reason", reason),
+		slog.F("count", count),
+	)
+
+	// Convert batch map to parallel arrays for the batch query.
+	// Also build map of agent IDs for per-agent metrics and pubsub.
+	var (
+		agentIDs    = make([]uuid.UUID, 0, count)
+		keys        = make([]string, 0, count)
+		values      = make([]string, 0, count)
+		errors      = make([]string, 0, count)
+		collectedAt = make([]time.Time, 0, count)
+		agentKeys   = make(map[uuid.UUID]int) // Track keys per agent for metrics
+	)
+
+	for ck, mv := range b.batch {
+		agentIDs = append(agentIDs, ck.agentID)
+		keys = append(keys, ck.key)
+		values = append(values, mv.v)
+		errors = append(errors, mv.error)
+		collectedAt = append(collectedAt, mv.collectedAt)
+		agentKeys[ck.agentID]++
+	}
+
+	// Batch has been processed into slices for our DB request, so we can clear it.
+	// It's safe to clear before we know whether the flush is successful as agent metadata is not critical, and therefore
+	// we do not retry failed flushes and losing a batch of metadata is okay.
+	b.batch = make(map[compositeKey]value)
+	b.currentBatchLen.Store(0)
+
+	// Record per-agent utilization metrics.
+	for _, keyCount := range agentKeys {
+		b.Metrics.BatchUtilization.Observe(float64(keyCount))
+	}
+
+	// Update the database with all metadata updates in a single query.
+	err := b.store.BatchUpdateWorkspaceAgentMetadata(ctx, database.BatchUpdateWorkspaceAgentMetadataParams{
+		WorkspaceAgentID: agentIDs,
+		Key:              keys,
+		Value:            values,
+		Error:            errors,
+		CollectedAt:      collectedAt,
+	})
+	elapsed := b.clock.Since(start)
+
+	if err != nil {
+		if database.IsQueryCanceledError(err) {
+			b.log.Debug(ctx, "query canceled, skipping update of workspace agent metadata", slog.F("elapsed", elapsed))
+			return
+		}
+		b.log.Error(ctx, "error updating workspace agent metadata", slog.Error(err), slog.F("elapsed", elapsed))
+		return
+	}
+
+	// Build list of unique agent IDs for pubsub notification.
+	uniqueAgentIDs := make([]uuid.UUID, 0, len(agentKeys))
+	for agentID := range agentKeys {
+		uniqueAgentIDs = append(uniqueAgentIDs, agentID)
+	}
+
+	// Encode agent IDs into chunks and publish them.
+	chunks, err := EncodeAgentIDChunks(uniqueAgentIDs)
+	if err != nil {
+		b.log.Error(ctx, "Agent ID chunk encoding for pubsub failed",
+			slog.Error(err))
+	}
+	for _, chunk := range chunks {
+		if err := b.ps.Publish(MetadataBatchPubsubChannel, chunk); err != nil {
+			b.log.Error(ctx, "failed to publish workspace agent metadata batch",
+				slog.Error(err),
+				slog.F("chunk_size", len(chunk)/UUIDBase64Size),
+				slog.F("payload_size", len(chunk)),
+			)
+			b.Metrics.PublishErrors.Inc()
+		}
+	}
+
+	// Record successful batch size and flush duration after successful send/publish.
+	b.Metrics.BatchSize.Observe(float64(count))
+	b.Metrics.MetadataTotal.Add(float64(count))
+	b.Metrics.BatchesTotal.WithLabelValues(reason).Inc()
+	b.Metrics.FlushDuration.WithLabelValues(reason).Observe(time.Since(start).Seconds())
+
+	elapsed = time.Since(start)
+	b.log.Debug(ctx, "flush complete",
+		slog.F("count", count),
+		slog.F("elapsed", elapsed),
+		slog.F("reason", reason),
+	)
+}
@@ -0,0 +1,95 @@
+package metadatabatcher
+
+import (
+	"github.com/prometheus/client_golang/prometheus"
+)
+
+type Metrics struct {
+	BatchUtilization prometheus.Histogram
+	FlushDuration    *prometheus.HistogramVec
+	BatchSize        prometheus.Histogram
+	BatchesTotal     *prometheus.CounterVec
+	DroppedKeysTotal prometheus.Counter
+	MetadataTotal    prometheus.Counter
+	PublishErrors    prometheus.Counter
+}
+
+func NewMetrics() Metrics {
+	return Metrics{
+		BatchUtilization: prometheus.NewHistogram(prometheus.HistogramOpts{
+			Namespace: "coderd",
+			Subsystem: "agentapi",
+			Name:      "metadata_batch_utilization",
+			Help:      "Number of metadata keys per agent in each batch, updated before flushes.",
+			Buckets:   []float64{1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 40, 80, 160},
+		}),
+
+		BatchSize: prometheus.NewHistogram(prometheus.HistogramOpts{
+			Namespace: "coderd",
+			Subsystem: "agentapi",
+			Name:      "metadata_batch_size",
+			Help:      "Total number of metadata entries in each batch, updated before flushes.",
+			Buckets:   []float64{10, 25, 50, 100, 150, 200, 250, 300, 350, 400, 450, 500},
+		}),
+
+		FlushDuration: prometheus.NewHistogramVec(prometheus.HistogramOpts{
+			Namespace: "coderd",
+			Subsystem: "agentapi",
+			Name:      "metadata_flush_duration_seconds",
+			Help:      "Time taken to flush metadata batch to database and pubsub.",
+			Buckets:   []float64{0.01, 0.025, 0.05, 0.1, 0.25, 0.5, 1.0, 2.5, 5.0},
+		}, []string{"reason"}),
+
+		BatchesTotal: prometheus.NewCounterVec(prometheus.CounterOpts{
+			Namespace: "coderd",
+			Subsystem: "agentapi",
+			Name:      "metadata_batches_total",
+			Help:      "Total number of metadata batches flushed.",
+		}, []string{"reason"}),
+
+		DroppedKeysTotal: prometheus.NewCounter(prometheus.CounterOpts{
+			Namespace: "coderd",
+			Subsystem: "agentapi",
+			Name:      "metadata_dropped_keys_total",
+			Help:      "Total number of metadata keys dropped due to capacity limits.",
+		}),
+
+		MetadataTotal: prometheus.NewCounter(prometheus.CounterOpts{
+			Namespace: "coderd",
+			Subsystem: "agentapi",
+			Name:      "metadata_flushed_total",
+			Help:      "Total number of unique metadatas flushed.",
+		}),
+
+		PublishErrors: prometheus.NewCounter(prometheus.CounterOpts{
+			Namespace: "coderd",
+			Subsystem: "agentapi",
+			Name:      "metadata_publish_errors_total",
+			Help:      "Total number of metadata batch pubsub publish calls that have resulted in an error.",
+		}),
+	}
+}
+
+func (m Metrics) Collectors() []prometheus.Collector {
+	return []prometheus.Collector{
+		m.BatchUtilization,
+		m.BatchSize,
+		m.FlushDuration,
+		m.BatchesTotal,
+		m.DroppedKeysTotal,
+		m.MetadataTotal,
+		m.PublishErrors,
+	}
+}
+
+func (m Metrics) register(reg prometheus.Registerer) {
+	if reg != nil {
+		reg.MustRegister(m.BatchUtilization)
+		reg.MustRegister(m.BatchSize)
+		reg.MustRegister(m.FlushDuration)
+		reg.MustRegister(m.DroppedKeysTotal)
+		reg.MustRegister(m.BatchesTotal)
+		reg.MustRegister(m.MetadataTotal)
+		reg.MustRegister(m.PublishErrors)
+	}
+}
@@ -91,7 +91,7 @@ func (a *SubAgentAPI) CreateSubAgent(ctx context.Context, req *agentproto.Create
 		Name:                     agentName,
 		ResourceID:               parentAgent.ResourceID,
 		AuthToken:                uuid.New(),
-		AuthInstanceID:           parentAgent.AuthInstanceID,
+		AuthInstanceID:           sql.NullString{},
 		Architecture:             req.Architecture,
 		EnvironmentVariables:     pqtype.NullRawMessage{},
 		OperatingSystem:          req.OperatingSystem,
@@ -175,6 +175,52 @@ func TestSubAgentAPI(t *testing.T) {
 		}
 	})

+	// Context: https://github.com/coder/coder/pull/22196
+	t.Run("CreateSubAgentDoesNotInheritAuthInstanceID", func(t *testing.T) {
+		t.Parallel()
+
+		var (
+			log   = testutil.Logger(t)
+			clock = quartz.NewMock(t)
+
+			db, org     = newDatabaseWithOrg(t)
+			user, agent = newUserWithWorkspaceAgent(t, db, org)
+		)
+
+		// Given: The parent agent has an AuthInstanceID set
+		ctx := testutil.Context(t, testutil.WaitShort)
+		parentAgent, err := db.GetWorkspaceAgentByID(dbauthz.AsSystemRestricted(ctx), agent.ID)
+		require.NoError(t, err)
+		require.True(t, parentAgent.AuthInstanceID.Valid, "parent agent should have an AuthInstanceID")
+		require.NotEmpty(t, parentAgent.AuthInstanceID.String)
+
+		api := newAgentAPI(t, log, db, clock, user, org, agent)
+
+		// When: We create a sub agent
+		createResp, err := api.CreateSubAgent(ctx, &proto.CreateSubAgentRequest{
+			Name:            "sub-agent",
+			Directory:       "/workspaces/test",
+			Architecture:    "amd64",
+			OperatingSystem: "linux",
+		})
+		require.NoError(t, err)
+
+		subAgentID, err := uuid.FromBytes(createResp.Agent.Id)
+		require.NoError(t, err)
+
+		// Then: The sub-agent must NOT re-use the parent's AuthInstanceID.
+		subAgent, err := db.GetWorkspaceAgentByID(dbauthz.AsSystemRestricted(ctx), subAgentID)
+		require.NoError(t, err)
+		assert.False(t, subAgent.AuthInstanceID.Valid, "sub-agent should not have an AuthInstanceID")
+		assert.Empty(t, subAgent.AuthInstanceID.String, "sub-agent AuthInstanceID string should be empty")
+
+		// Double-check: looking up by the parent's instance ID must
+		// still return the parent, not the sub-agent.
+		lookedUp, err := db.GetWorkspaceAgentByInstanceID(dbauthz.AsSystemRestricted(ctx), parentAgent.AuthInstanceID.String)
+		require.NoError(t, err)
+		assert.Equal(t, parentAgent.ID, lookedUp.ID, "instance ID lookup should still return the parent agent")
+	})
+
 	type expectedAppError struct {
 		index int32
 		field string
--- a/Show More
+++ b/Show More