Merge branch 'main' into security-patch-train-doc

ci(.github): automate security patch PRs and backports
perf(coderd): batch chat heartbeat queries into single UPDATE per interval (#24037 )
2026-04-07 16:31:36 +02:00 · 2026-04-07 16:27:25 +02:00 · 2026-04-07 10:25:46 -04:00 · 2026-04-07 07:24:53 -07:00 · 2026-04-08 00:17:06 +10:00 · 2026-04-07 15:05:27 +01:00
182 changed files with 7175 additions and 2686 deletions
@@ -31,7 +31,8 @@ updates:
        patterns:
          - "golang.org/x/*"
    ignore:
-      # Ignore patch updates for all dependencies
+      # Patch updates are handled by the security-patch-prs workflow so this
+      # lane stays focused on broader dependency updates.
      - dependency-name: "*"
        update-types:
          - version-update:semver-patch
@@ -56,7 +57,7 @@ updates:
    labels: []
    ignore:
      # We need to coordinate terraform updates with the version hardcoded in
-      # our Go code.
+      # our Go code. These are handled by the security-patch-prs workflow.
      - dependency-name: "terraform"

  - package-ecosystem: "npm"
@@ -117,11 +118,11 @@ updates:
      interval: "weekly"
    commit-message:
      prefix: "chore"
+    labels: []
    groups:
      coder-modules:
        patterns:
          - "coder/*/coder"
-    labels: []
    ignore:
      - dependency-name: "*"
        update-types:
@@ -35,7 +35,7 @@ jobs:
      tailnet-integration: ${{ steps.filter.outputs.tailnet-integration }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -157,7 +157,7 @@ jobs:
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -247,7 +247,7 @@ jobs:
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -272,7 +272,7 @@ jobs:
    if: ${{ !cancelled() }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -327,7 +327,7 @@ jobs:
    timeout-minutes: 20
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -379,7 +379,7 @@ jobs:
          - windows-2022
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -575,7 +575,7 @@ jobs:
    timeout-minutes: 25
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -637,7 +637,7 @@ jobs:
    timeout-minutes: 25
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -709,7 +709,7 @@ jobs:
    timeout-minutes: 20
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -736,7 +736,7 @@ jobs:
    timeout-minutes: 20
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -769,7 +769,7 @@ jobs:
    name: ${{ matrix.variant.name }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -849,7 +849,7 @@ jobs:
    if: needs.changes.outputs.site == 'true' || needs.changes.outputs.ci == 'true'
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

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

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

@@ -1005,7 +1005,7 @@ jobs:
    if: always()
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -1043,7 +1043,7 @@ jobs:
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -1097,7 +1097,7 @@ jobs:
      IMAGE: ghcr.io/coder/coder-preview:${{ steps.build-docker.outputs.tag }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -1479,7 +1479,7 @@ jobs:
    if: needs.changes.outputs.db == 'true' || needs.changes.outputs.ci == 'true' || github.ref == 'refs/heads/main'
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

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

@@ -36,7 +36,7 @@ jobs:
      verdict: ${{ steps.check.outputs.verdict }} # DEPLOY or NOOP
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -65,7 +65,7 @@ jobs:
      packages: write # to retag image as dogfood
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -142,7 +142,7 @@ jobs:
    needs: deploy
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

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

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

@@ -125,7 +125,7 @@ jobs:
      id-token: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

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

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

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

@@ -39,7 +39,7 @@ jobs:
      PR_OPEN: ${{ steps.check_pr.outputs.pr_open }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -76,7 +76,7 @@ jobs:
    runs-on: "ubuntu-latest"
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -184,7 +184,7 @@ jobs:
      pull-requests: write # needed for commenting on PRs
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -228,7 +228,7 @@ jobs:
      CODER_IMAGE_TAG: ${{ needs.get_info.outputs.CODER_IMAGE_TAG }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -288,7 +288,7 @@ jobs:
      PR_HOSTNAME: "pr${{ needs.get_info.outputs.PR_NUMBER }}.${{ secrets.PR_DEPLOYMENTS_DOMAIN }}"
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

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

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

@@ -81,7 +81,7 @@ jobs:
      version: ${{ steps.version.outputs.version }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -673,7 +673,7 @@ jobs:

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

@@ -749,7 +749,7 @@ jobs:

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

@@ -20,7 +20,7 @@ jobs:

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

@@ -47,6 +47,6 @@ jobs:

      # Upload the results to GitHub's code scanning dashboard.
      - name: "Upload to code-scanning"
-        uses: github/codeql-action/upload-sarif@5d4e8d1aca955e8d8589aabd499c5cae939e33c7 # v3.29.5
+        uses: github/codeql-action/upload-sarif@c10b8064de6f491fea524254123dbe5e09572f13 # v3.29.5
        with:
          sarif_file: results.sarif
@@ -0,0 +1,354 @@
+name: security-backport
+
+on:
+  pull_request_target:
+    types:
+      - labeled
+      - unlabeled
+      - closed
+  workflow_dispatch:
+    inputs:
+      pull_request:
+        description: Pull request number to backport.
+        required: true
+        type: string
+
+permissions:
+  contents: write
+  pull-requests: write
+  issues: write
+
+concurrency:
+  group: ${{ github.workflow }}-${{ github.event.pull_request.number || inputs.pull_request }}
+  cancel-in-progress: false
+
+env:
+  LATEST_BRANCH: release/2.31
+  STABLE_BRANCH: release/2.30
+  STABLE_1_BRANCH: release/2.29
+
+jobs:
+  label-policy:
+    if: github.event_name == 'pull_request_target'
+    runs-on: ubuntu-latest
+    steps:
+      - name: Harden Runner
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        with:
+          egress-policy: audit
+
+      - name: Apply security backport label policy
+        shell: bash
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+        run: |
+          set -euo pipefail
+
+          pr_number="$(jq -r '.pull_request.number' "${GITHUB_EVENT_PATH}")"
+          pr_json="$(gh pr view "${pr_number}" --json number,title,url,baseRefName,labels)"
+
+          PR_JSON="${pr_json}" \
+          python3 - <<'PY'
+          import json
+          import os
+          import subprocess
+          import sys
+
+          pr = json.loads(os.environ["PR_JSON"])
+
+          pr_number = pr["number"]
+          labels = [label["name"] for label in pr.get("labels", [])]
+
+          def has(label: str) -> bool:
+              return label in labels
+
+          def ensure_label(label: str) -> None:
+              if not has(label):
+                  subprocess.run(
+                      ["gh", "pr", "edit", str(pr_number), "--add-label", label],
+                      check=False,
+                  )
+
+          def remove_label(label: str) -> None:
+              if has(label):
+                  subprocess.run(
+                      ["gh", "pr", "edit", str(pr_number), "--remove-label", label],
+                      check=False,
+                  )
+
+          def comment(body: str) -> None:
+              subprocess.run(
+                  ["gh", "pr", "comment", str(pr_number), "--body", body],
+                  check=True,
+              )
+
+          if not has("security:patch"):
+              remove_label("status:needs-severity")
+              sys.exit(0)
+
+          severity_labels = [
+              label
+              for label in ("severity:medium", "severity:high", "severity:critical")
+              if has(label)
+          ]
+          if len(severity_labels) == 0:
+              ensure_label("status:needs-severity")
+              comment(
+                  "This PR is labeled `security:patch` but is missing a severity "
+                  "label. Add one of `severity:medium`, `severity:high`, or "
+                  "`severity:critical` before backport automation can proceed."
+              )
+              sys.exit(0)
+
+          if len(severity_labels) > 1:
+              comment(
+                  "This PR has multiple severity labels. Keep exactly one of "
+                  "`severity:medium`, `severity:high`, or `severity:critical`."
+              )
+              sys.exit(1)
+
+          remove_label("status:needs-severity")
+
+          target_labels = [
+              label
+              for label in ("backport:stable", "backport:stable-1")
+              if has(label)
+          ]
+          has_none = has("backport:none")
+          if has_none and target_labels:
+              comment(
+                  "`backport:none` cannot be combined with other backport labels. "
+                  "Remove `backport:none` or remove the explicit backport targets."
+              )
+              sys.exit(1)
+
+          if not has_none and not target_labels:
+              ensure_label("backport:stable")
+              ensure_label("backport:stable-1")
+              comment(
+                  "Applied default backport labels `backport:stable` and "
+                  "`backport:stable-1` for a qualifying security patch."
+              )
+          PY
+
+  backport:
+    if: >
+      github.event_name == 'workflow_dispatch' ||
+      (
+        github.event_name == 'pull_request_target' &&
+        github.event.pull_request.merged == true
+      )
+    runs-on: ubuntu-latest
+    steps:
+      - name: Harden Runner
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        with:
+          egress-policy: audit
+
+      - name: Checkout
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+        with:
+          fetch-depth: 0
+          persist-credentials: false
+
+      - name: Resolve PR metadata
+        id: metadata
+        shell: bash
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+          INPUT_PR_NUMBER: ${{ inputs.pull_request }}
+          LATEST_BRANCH: ${{ env.LATEST_BRANCH }}
+          STABLE_BRANCH: ${{ env.STABLE_BRANCH }}
+          STABLE_1_BRANCH: ${{ env.STABLE_1_BRANCH }}
+        run: |
+          set -euo pipefail
+
+          if [ "${GITHUB_EVENT_NAME}" = "workflow_dispatch" ]; then
+            pr_number="${INPUT_PR_NUMBER}"
+          else
+            pr_number="$(jq -r '.pull_request.number' "${GITHUB_EVENT_PATH}")"
+          fi
+
+          case "${pr_number}" in
+            ''|*[!0-9]*)
+              echo "A valid pull request number is required."
+              exit 1
+              ;;
+          esac
+
+          pr_json="$(gh pr view "${pr_number}" --json number,title,url,mergeCommit,baseRefName,labels,mergedAt,author)"
+
+          PR_JSON="${pr_json}" \
+          python3 - <<'PY'
+          import json
+          import os
+          import sys
+
+          pr = json.loads(os.environ["PR_JSON"])
+          github_output = os.environ["GITHUB_OUTPUT"]
+
+          labels = [label["name"] for label in pr.get("labels", [])]
+          if "security:patch" not in labels:
+              print("Not a security patch PR; skipping.")
+              sys.exit(0)
+
+          severity_labels = [
+              label
+              for label in ("severity:medium", "severity:high", "severity:critical")
+              if label in labels
+          ]
+          if len(severity_labels) != 1:
+              raise SystemExit(
+                  "Merged security patch PR must have exactly one severity label."
+              )
+
+          if not pr.get("mergedAt"):
+              raise SystemExit(f"PR #{pr['number']} is not merged.")
+
+          if "backport:none" in labels:
+              target_pairs = []
+          else:
+              mapping = {
+                  "backport:stable": os.environ["STABLE_BRANCH"],
+                  "backport:stable-1": os.environ["STABLE_1_BRANCH"],
+              }
+              target_pairs = []
+              for label_name, branch in mapping.items():
+                  if label_name in labels and branch and branch != pr["baseRefName"]:
+                      target_pairs.append({"label": label_name, "branch": branch})
+
+          with open(github_output, "a", encoding="utf-8") as f:
+              f.write(f"pr_number={pr['number']}\n")
+              f.write(f"merge_sha={pr['mergeCommit']['oid']}\n")
+              f.write(f"title={pr['title']}\n")
+              f.write(f"url={pr['url']}\n")
+              f.write(f"author={pr['author']['login']}\n")
+              f.write(f"severity_label={severity_labels[0]}\n")
+              f.write(f"target_pairs={json.dumps(target_pairs)}\n")
+          PY
+
+      - name: Backport to release branches
+        if: ${{ steps.metadata.outputs.target_pairs != '[]' }}
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+          PR_NUMBER: ${{ steps.metadata.outputs.pr_number }}
+          MERGE_SHA: ${{ steps.metadata.outputs.merge_sha }}
+          PR_TITLE: ${{ steps.metadata.outputs.title }}
+          PR_URL: ${{ steps.metadata.outputs.url }}
+          PR_AUTHOR: ${{ steps.metadata.outputs.author }}
+          SEVERITY_LABEL: ${{ steps.metadata.outputs.severity_label }}
+          TARGET_PAIRS: ${{ steps.metadata.outputs.target_pairs }}
+        run: |
+          set -euo pipefail
+
+          git config user.name "github-actions[bot]"
+          git config user.email "41898282+github-actions[bot]@users.noreply.github.com"
+
+          git remote set-url origin "https://x-access-token:${GH_TOKEN}@github.com/${GITHUB_REPOSITORY}.git"
+          git fetch origin --prune
+
+          merge_parent_count="$(git rev-list --parents -n 1 "${MERGE_SHA}" | awk '{print NF-1}')"
+
+          failures=()
+          successes=()
+
+          while IFS=$'\t' read -r backport_label target_branch; do
+            [ -n "${target_branch}" ] || continue
+
+            safe_branch_name="${target_branch//\//-}"
+            head_branch="backport/${safe_branch_name}/pr-${PR_NUMBER}"
+
+            existing_pr="$(gh pr list \
+              --base "${target_branch}" \
+              --head "${head_branch}" \
+              --state all \
+              --json number,url \
+              --jq '.[0]')"
+            if [ -n "${existing_pr}" ] && [ "${existing_pr}" != "null" ]; then
+              pr_url="$(printf '%s' "${existing_pr}" | jq -r '.url')"
+              successes+=("${target_branch}:existing:${pr_url}")
+              continue
+            fi
+
+            git checkout -B "${head_branch}" "origin/${target_branch}"
+
+            if [ "${merge_parent_count}" -gt 1 ]; then
+              cherry_pick_args=(-m 1 "${MERGE_SHA}")
+            else
+              cherry_pick_args=("${MERGE_SHA}")
+            fi
+
+            if ! git cherry-pick -x "${cherry_pick_args[@]}"; then
+              git cherry-pick --abort || true
+              gh pr edit "${PR_NUMBER}" --add-label "backport:conflict" || true
+              gh pr comment "${PR_NUMBER}" --body \
+                "Automatic backport to \`${target_branch}\` conflicted. The original author or release manager should resolve it manually."
+              failures+=("${target_branch}:cherry-pick failed")
+              continue
+            fi
+
+            git push --force-with-lease origin "${head_branch}"
+
+            body_file="$(mktemp)"
+            printf '%s\n' \
+              "Automated backport of [#${PR_NUMBER}](${PR_URL})." \
+              "" \
+              "- Source PR: #${PR_NUMBER}" \
+              "- Source commit: ${MERGE_SHA}" \
+              "- Target branch: ${target_branch}" \
+              "- Severity: ${SEVERITY_LABEL}" \
+              > "${body_file}"
+
+            pr_url="$(gh pr create \
+              --base "${target_branch}" \
+              --head "${head_branch}" \
+              --title "${PR_TITLE} (backport to ${target_branch})" \
+              --body-file "${body_file}")"
+
+            backport_pr_number="$(gh pr list \
+              --base "${target_branch}" \
+              --head "${head_branch}" \
+              --state open \
+              --json number \
+              --jq '.[0].number')"
+
+            gh pr edit "${backport_pr_number}" \
+              --add-label "security:patch" \
+              --add-label "${SEVERITY_LABEL}" \
+              --add-label "${backport_label}" || true
+
+            successes+=("${target_branch}:created:${pr_url}")
+          done < <(
+            python3 - <<'PY'
+            import json
+            import os
+            for pair in json.loads(os.environ["TARGET_PAIRS"]):
+                print(f"{pair['label']}\t{pair['branch']}")
+            PY
+          )
+
+          summary_file="$(mktemp)"
+          {
+            echo "## Security backport summary"
+            echo
+            if [ "${#successes[@]}" -gt 0 ]; then
+              echo "### Created or existing"
+              for entry in "${successes[@]}"; do
+                echo "- ${entry}"
+              done
+              echo
+            fi
+            if [ "${#failures[@]}" -gt 0 ]; then
+              echo "### Failures"
+              for entry in "${failures[@]}"; do
+                echo "- ${entry}"
+              done
+            fi
+          } | tee -a "${GITHUB_STEP_SUMMARY}" > "${summary_file}"
+
+          gh pr comment "${PR_NUMBER}" --body-file "${summary_file}"
+
+          if [ "${#failures[@]}" -gt 0 ]; then
+            printf 'Backport failures:\n%s\n' "${failures[@]}" >&2
+            exit 1
+          fi
@@ -0,0 +1,214 @@
+name: security-patch-prs
+
+on:
+  workflow_dispatch:
+  schedule:
+    - cron: "0 3 * * 1-5"
+
+permissions:
+  contents: write
+  pull-requests: write
+
+jobs:
+  patch:
+    strategy:
+      fail-fast: false
+      matrix:
+        lane:
+          - gomod
+          - terraform
+    runs-on: ubuntu-latest
+    steps:
+      - name: Harden Runner
+        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        with:
+          egress-policy: audit
+
+      - name: Checkout
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+        with:
+          persist-credentials: false
+
+      - name: Setup Go
+        uses: ./.github/actions/setup-go
+
+      - name: Patch Go dependencies
+        if: matrix.lane == 'gomod'
+        shell: bash
+        run: |
+          set -euo pipefail
+
+          go get -u=patch ./...
+          go mod tidy
+
+          # Guardrail: do not auto-edit replace directives.
+          if git diff --unified=0 -- go.mod | grep -E '^[+-]replace '; then
+            echo "Refusing to auto-edit go.mod replace directives"
+            exit 1
+          fi
+
+          # Guardrail: only go.mod / go.sum may change.
+          extra="$(git diff --name-only | grep -Ev '^(go\.mod|go\.sum)$' || true)"
+          test -z "$extra" || { echo "Unexpected files changed:"; echo "$extra"; exit 1; }
+
+      - name: Patch bundled Terraform
+        if: matrix.lane == 'terraform'
+        shell: bash
+        run: |
+          set -euo pipefail
+
+          current="$(
+            grep -oE 'NewVersion\("[0-9]+\.[0-9]+\.[0-9]+"\)' \
+              provisioner/terraform/install.go \
+            | head -1 \
+            | grep -oE '[0-9]+\.[0-9]+\.[0-9]+'
+          )"
+
+          series="$(echo "$current" | cut -d. -f1,2)"
+
+          latest="$(
+            curl -fsSL https://releases.hashicorp.com/terraform/index.json \
+            | jq -r --arg series "$series" '
+                .versions
+                | keys[]
+                | select(startswith($series + "."))
+              ' \
+            | sort -V \
+            | tail -1
+          )"
+
+          test -n "$latest"
+          [ "$latest" != "$current" ] || exit 0
+
+          CURRENT_TERRAFORM_VERSION="$current" \
+          LATEST_TERRAFORM_VERSION="$latest" \
+          python3 - <<'PY'
+          from pathlib import Path
+          import os
+
+          current = os.environ["CURRENT_TERRAFORM_VERSION"]
+          latest = os.environ["LATEST_TERRAFORM_VERSION"]
+
+          updates = {
+              "scripts/Dockerfile.base": (
+                  f"terraform/{current}/",
+                  f"terraform/{latest}/",
+              ),
+              "provisioner/terraform/install.go": (
+                  f'NewVersion("{current}")',
+                  f'NewVersion("{latest}")',
+              ),
+              "install.sh": (
+                  f'TERRAFORM_VERSION="{current}"',
+                  f'TERRAFORM_VERSION="{latest}"',
+              ),
+          }
+
+          for path_str, (before, after) in updates.items():
+              path = Path(path_str)
+              content = path.read_text()
+              if before not in content:
+                  raise SystemExit(f"did not find expected text in {path_str}: {before}")
+              path.write_text(content.replace(before, after))
+          PY
+
+          # Guardrail: only the Terraform-version files may change.
+          extra="$(git diff --name-only | grep -Ev '^(scripts/Dockerfile.base|provisioner/terraform/install.go|install.sh)$' || true)"
+          test -z "$extra" || { echo "Unexpected files changed:"; echo "$extra"; exit 1; }
+
+      - name: Validate Go dependency patch
+        if: matrix.lane == 'gomod'
+        shell: bash
+        run: |
+          set -euo pipefail
+          go test ./...
+
+      - name: Validate Terraform patch
+        if: matrix.lane == 'terraform'
+        shell: bash
+        run: |
+          set -euo pipefail
+          go test ./provisioner/terraform/...
+          docker build -f scripts/Dockerfile.base .
+
+      - name: Skip PR creation when there are no changes
+        id: changes
+        shell: bash
+        run: |
+          set -euo pipefail
+
+          if git diff --quiet; then
+            echo "has_changes=false" >> "${GITHUB_OUTPUT}"
+          else
+            echo "has_changes=true" >> "${GITHUB_OUTPUT}"
+          fi
+
+      - name: Commit changes
+        if: steps.changes.outputs.has_changes == 'true'
+        shell: bash
+        run: |
+          set -euo pipefail
+
+          git config user.name "github-actions[bot]"
+          git config user.email "41898282+github-actions[bot]@users.noreply.github.com"
+
+          git checkout -B "secpatch/${{ matrix.lane }}"
+          git add -A
+          git commit -m "security: patch ${{ matrix.lane }}"
+
+      - name: Push branch
+        if: steps.changes.outputs.has_changes == 'true'
+        shell: bash
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+        run: |
+          set -euo pipefail
+
+          git push --force-with-lease \
+            "https://x-access-token:${GH_TOKEN}@github.com/${{ github.repository }}.git" \
+            "HEAD:refs/heads/secpatch/${{ matrix.lane }}"
+
+      - name: Create or update PR
+        if: steps.changes.outputs.has_changes == 'true'
+        shell: bash
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+        run: |
+          set -euo pipefail
+
+          branch="secpatch/${{ matrix.lane }}"
+          title="security: patch ${{ matrix.lane }}"
+          body="$(cat <<'EOF'
+          Automated security patch PR for `${{ matrix.lane }}`.
+
+          Scope:
+          - gomod: patch-level Go dependency updates only
+          - terraform: bundled Terraform patch updates only
+
+          Guardrails:
+          - no application-code edits
+          - no auto-editing of go.mod replace directives
+          - CI must pass
+          EOF
+          )"
+
+          existing_pr="$(gh pr list --head "${branch}" --base main --json number --jq '.[0].number // empty')"
+          if [[ -n "${existing_pr}" ]]; then
+            gh pr edit "${existing_pr}" \
+              --title "${title}" \
+              --body "${body}"
+            pr_number="${existing_pr}"
+          else
+            gh pr create \
+              --base main \
+              --head "${branch}" \
+              --title "${title}" \
+              --body "${body}"
+            pr_number="$(gh pr list --head "${branch}" --base main --json number --jq '.[0].number // empty')"
+          fi
+
+          for label in security dependencies automated-pr; do
+            if gh label list --json name --jq '.[].name' | grep -Fxq "${label}"; then
+              gh pr edit "${pr_number}" --add-label "${label}"
+            fi
+          done
@@ -27,7 +27,7 @@ jobs:
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -40,7 +40,7 @@ jobs:
        uses: ./.github/actions/setup-go

      - name: Initialize CodeQL
-        uses: github/codeql-action/init@5d4e8d1aca955e8d8589aabd499c5cae939e33c7 # v3.29.5
+        uses: github/codeql-action/init@c10b8064de6f491fea524254123dbe5e09572f13 # v3.29.5
        with:
          languages: go, javascript

@@ -50,7 +50,7 @@ jobs:
          rm Makefile

      - name: Perform CodeQL Analysis
-        uses: github/codeql-action/analyze@5d4e8d1aca955e8d8589aabd499c5cae939e33c7 # v3.29.5
+        uses: github/codeql-action/analyze@c10b8064de6f491fea524254123dbe5e09572f13 # v3.29.5

      - name: Send Slack notification on failure
        if: ${{ failure() }}
@@ -18,7 +18,7 @@ jobs:
      pull-requests: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

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

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

@@ -21,7 +21,7 @@ jobs:
      pull-requests: write # required to post PR review comments by the action
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
        with:
          egress-policy: audit

@@ -187,7 +187,11 @@ func (*Manager) connectServer(ctx context.Context, cfg ServerConfig) (*client.Cl
 	connectCtx, cancel := context.WithTimeout(ctx, connectTimeout)
 	defer cancel()

-	if err := c.Start(connectCtx); err != nil {
+	// Use the parent ctx (not connectCtx) so the subprocess outlives
+	// the connect/initialize handshake. connectCtx bounds only the
+	// Initialize call below. The subprocess is cleaned up when the
+	// Manager is closed or ctx is canceled.
+	if err := c.Start(ctx); err != nil {
 		_ = c.Close()
 		return nil, xerrors.Errorf("start %q: %w", cfg.Name, err)
 	}
@@ -1,6 +1,11 @@
 package agentmcp

 import (
+	"bufio"
+	"context"
+	"encoding/json"
+	"fmt"
+	"os"
 	"testing"

 	"github.com/mark3labs/mcp-go/mcp"
@@ -8,6 +13,7 @@ import (
 	"github.com/stretchr/testify/require"

 	"github.com/coder/coder/v2/codersdk/workspacesdk"
+	"github.com/coder/coder/v2/testutil"
 )

 func TestSplitToolName(t *testing.T) {
@@ -193,3 +199,118 @@ func TestConvertResult(t *testing.T) {
 		})
 	}
 }
+
+// TestConnectServer_StdioProcessSurvivesConnect verifies that a stdio MCP
+// server subprocess remains alive after connectServer returns. This is a
+// regression test for a bug where the subprocess was tied to a short-lived
+// connectCtx and killed as soon as the context was canceled.
+func TestConnectServer_StdioProcessSurvivesConnect(t *testing.T) {
+	t.Parallel()
+
+	if os.Getenv("TEST_MCP_FAKE_SERVER") == "1" {
+		// Child process: act as a minimal MCP server over stdio.
+		runFakeMCPServer()
+		return
+	}
+
+	// Get the path to the test binary so we can re-exec ourselves
+	// as a fake MCP server subprocess.
+	testBin, err := os.Executable()
+	require.NoError(t, err)
+
+	cfg := ServerConfig{
+		Name:      "fake",
+		Transport: "stdio",
+		Command:   testBin,
+		Args:      []string{"-test.run=^TestConnectServer_StdioProcessSurvivesConnect$"},
+		Env:       map[string]string{"TEST_MCP_FAKE_SERVER": "1"},
+	}
+
+	ctx := testutil.Context(t, testutil.WaitLong)
+	m := &Manager{}
+	client, err := m.connectServer(ctx, cfg)
+	require.NoError(t, err, "connectServer should succeed")
+	t.Cleanup(func() { _ = client.Close() })
+
+	// At this point connectServer has returned and its internal
+	// connectCtx has been canceled. The subprocess must still be
+	// alive. Verify by listing tools (requires a live server).
+	listCtx, listCancel := context.WithTimeout(ctx, testutil.WaitShort)
+	defer listCancel()
+	result, err := client.ListTools(listCtx, mcp.ListToolsRequest{})
+	require.NoError(t, err, "ListTools should succeed — server must be alive after connect")
+	require.Len(t, result.Tools, 1)
+	assert.Equal(t, "echo", result.Tools[0].Name)
+}
+
+// runFakeMCPServer implements a minimal JSON-RPC / MCP server over
+// stdin/stdout, just enough for initialize + tools/list.
+func runFakeMCPServer() {
+	scanner := bufio.NewScanner(os.Stdin)
+	for scanner.Scan() {
+		line := scanner.Bytes()
+
+		var req struct {
+			JSONRPC string          `json:"jsonrpc"`
+			ID      json.RawMessage `json:"id"`
+			Method  string          `json:"method"`
+		}
+		if err := json.Unmarshal(line, &req); err != nil {
+			continue
+		}
+
+		var resp any
+		switch req.Method {
+		case "initialize":
+			resp = map[string]any{
+				"jsonrpc": "2.0",
+				"id":      req.ID,
+				"result": map[string]any{
+					"protocolVersion": "2025-03-26",
+					"capabilities": map[string]any{
+						"tools": map[string]any{},
+					},
+					"serverInfo": map[string]any{
+						"name":    "fake-server",
+						"version": "0.0.1",
+					},
+				},
+			}
+		case "notifications/initialized":
+			// No response needed for notifications.
+			continue
+		case "tools/list":
+			resp = map[string]any{
+				"jsonrpc": "2.0",
+				"id":      req.ID,
+				"result": map[string]any{
+					"tools": []map[string]any{
+						{
+							"name":        "echo",
+							"description": "echoes input",
+							"inputSchema": map[string]any{
+								"type":       "object",
+								"properties": map[string]any{},
+							},
+						},
+					},
+				},
+			}
+		default:
+			resp = map[string]any{
+				"jsonrpc": "2.0",
+				"id":      req.ID,
+				"error": map[string]any{
+					"code":    -32601,
+					"message": "method not found",
+				},
+			}
+		}
+
+		out, err := json.Marshal(resp)
+		if err != nil {
+			continue
+		}
+		_, _ = fmt.Fprintf(os.Stdout, "%s\n", out)
+	}
+}
@@ -3,11 +3,13 @@
 		"enabled": true,
 		"clientKind": "git",
 		"useIgnoreFile": true,
-		"defaultBranch": "main",
+		"defaultBranch": "main"
 	},
 	"files": {
-		"includes": ["**", "!**/pnpm-lock.yaml"],
-		"ignoreUnknown": true,
+		// static/*.html are Go templates with {{ }} directives that
+		// Biome's HTML parser does not support.
+		"includes": ["**", "!**/pnpm-lock.yaml", "!**/static/*.html"],
+		"ignoreUnknown": true
 	},
 	"linter": {
 		"rules": {
@@ -15,7 +17,7 @@
 				"noSvgWithoutTitle": "off",
 				"useButtonType": "off",
 				"useSemanticElements": "off",
-				"noStaticElementInteractions": "off",
+				"noStaticElementInteractions": "off"
 			},
 			"correctness": {
 				"noUnusedImports": "warn",
@@ -24,9 +26,9 @@
 				"noUnusedVariables": {
 					"level": "warn",
 					"options": {
-						"ignoreRestSiblings": true,
-					},
-				},
+						"ignoreRestSiblings": true
+					}
+				}
 			},
 			"style": {
 				"noNonNullAssertion": "off",
@@ -47,7 +49,7 @@
 						"paths": {
 							"react": {
 								"message": "React 19 no longer requires forwardRef. Use ref as a prop instead.",
-								"importNames": ["forwardRef"],
+								"importNames": ["forwardRef"]
 							},
 							// "@mui/material/Alert": "Use components/Alert/Alert instead.",
 							// "@mui/material/AlertTitle": "Use components/Alert/Alert instead.",
@@ -115,10 +117,10 @@
 							"@emotion/styled": "Use Tailwind CSS instead.",
 							// "@emotion/cache": "Use Tailwind CSS instead.",
 							// "components/Stack/Stack": "Use Tailwind flex utilities instead (e.g., <div className='flex flex-col gap-4'>).",
-							"lodash": "Use lodash/<name> instead.",
-						},
-					},
-				},
+							"lodash": "Use lodash/<name> instead."
+						}
+					}
+				}
 			},
 			"suspicious": {
 				"noArrayIndexKey": "off",
@@ -129,14 +131,21 @@
 				"noConsole": {
 					"level": "error",
 					"options": {
-						"allow": ["error", "info", "warn"],
-					},
-				},
+						"allow": ["error", "info", "warn"]
+					}
+				}
 			},
 			"complexity": {
-				"noImportantStyles": "off", // TODO: check and fix !important styles
-			},
-		},
+				"noImportantStyles": "off" // TODO: check and fix !important styles
+			}
+		}
 	},
-	"$schema": "./node_modules/@biomejs/biome/configuration_schema.json",
+	"css": {
+		"parser": {
+			// Biome 2.3+ requires opt-in for @apply and other
+			// Tailwind directives.
+			"tailwindDirectives": true
+		}
+	},
+	"$schema": "./node_modules/@biomejs/biome/configuration_schema.json"
 }
@@ -14175,6 +14175,9 @@ const docTemplate = `{
                },
                "count": {
                    "type": "integer"
+                },
+                "count_cap": {
+                    "type": "integer"
                }
            }
        },
@@ -14496,6 +14499,9 @@ const docTemplate = `{
                },
                "count": {
                    "type": "integer"
+                },
+                "count_cap": {
+                    "type": "integer"
                }
            }
        },
@@ -12739,6 +12739,9 @@
 				},
 				"count": {
 					"type": "integer"
+				},
+				"count_cap": {
+					"type": "integer"
 				}
 			}
 		},
@@ -13039,6 +13042,9 @@
 				},
 				"count": {
 					"type": "integer"
+				},
+				"count_cap": {
+					"type": "integer"
 				}
 			}
 		},
@@ -26,6 +26,11 @@ import (
 	"github.com/coder/coder/v2/codersdk"
 )

+// Limit the count query to avoid a slow sequential scan due to joins
+// on a large table. Set to 0 to disable capping (but also see the note
+// in the SQL query).
+const auditLogCountCap = 2000
+
 // @Summary Get audit logs
 // @ID get-audit-logs
 // @Security CoderSessionToken
@@ -66,7 +71,7 @@ func (api *API) auditLogs(rw http.ResponseWriter, r *http.Request) {
 		countFilter.Username = ""
 	}

-	// Use the same filters to count the number of audit logs
+	countFilter.CountCap = auditLogCountCap
 	count, err := api.Database.CountAuditLogs(ctx, countFilter)
 	if dbauthz.IsNotAuthorizedError(err) {
 		httpapi.Forbidden(rw)
@@ -81,6 +86,7 @@ func (api *API) auditLogs(rw http.ResponseWriter, r *http.Request) {
 		httpapi.Write(ctx, rw, http.StatusOK, codersdk.AuditLogResponse{
 			AuditLogs: []codersdk.AuditLog{},
 			Count:     0,
+			CountCap:  auditLogCountCap,
 		})
 		return
 	}
@@ -98,6 +104,7 @@ func (api *API) auditLogs(rw http.ResponseWriter, r *http.Request) {
 	httpapi.Write(ctx, rw, http.StatusOK, codersdk.AuditLogResponse{
 		AuditLogs: api.convertAuditLogs(ctx, dblogs),
 		Count:     count,
+		CountCap:  auditLogCountCap,
 	})
 }

@@ -1528,7 +1528,10 @@ func nullInt64Ptr(v sql.NullInt64) *int64 {
 // Chat converts a database.Chat to a codersdk.Chat. It coalesces
 // nil slices and maps to empty values for JSON serialization and
 // derives RootChatID from the parent chain when not explicitly set.
-func Chat(c database.Chat, diffStatus *database.ChatDiffStatus) codersdk.Chat {
+// When diffStatus is non-nil the response includes diff metadata.
+// When files is non-empty the response includes file metadata;
+// pass nil to omit the files field (e.g. list endpoints).
+func Chat(c database.Chat, diffStatus *database.ChatDiffStatus, files []database.GetChatFileMetadataByChatIDRow) codersdk.Chat {
 	mcpServerIDs := c.MCPServerIDs
 	if mcpServerIDs == nil {
 		mcpServerIDs = []uuid.UUID{}
@@ -1581,6 +1584,19 @@ func Chat(c database.Chat, diffStatus *database.ChatDiffStatus) codersdk.Chat {
 		convertedDiffStatus := ChatDiffStatus(c.ID, diffStatus)
 		chat.DiffStatus = &convertedDiffStatus
 	}
+	if len(files) > 0 {
+		chat.Files = make([]codersdk.ChatFileMetadata, 0, len(files))
+		for _, row := range files {
+			chat.Files = append(chat.Files, codersdk.ChatFileMetadata{
+				ID:             row.ID,
+				OwnerID:        row.OwnerID,
+				OrganizationID: row.OrganizationID,
+				Name:           row.Name,
+				MimeType:       row.Mimetype,
+				CreatedAt:      row.CreatedAt,
+			})
+		}
+	}
 	if c.LastInjectedContext.Valid {
 		var parts []codersdk.ChatMessagePart
 		// Internal fields are stripped at write time in
@@ -1604,9 +1620,9 @@ func ChatRows(rows []database.GetChatsRow, diffStatusesByChatID map[uuid.UUID]da
 	for i, row := range rows {
 		diffStatus, ok := diffStatusesByChatID[row.Chat.ID]
 		if ok {
-			result[i] = Chat(row.Chat, &diffStatus)
+			result[i] = Chat(row.Chat, &diffStatus, nil)
 		} else {
-			result[i] = Chat(row.Chat, nil)
+			result[i] = Chat(row.Chat, nil, nil)
 			if diffStatusesByChatID != nil {
 				emptyDiffStatus := ChatDiffStatus(row.Chat.ID, nil)
 				result[i].DiffStatus = &emptyDiffStatus
@@ -561,14 +561,26 @@ func TestChat_AllFieldsPopulated(t *testing.T) {
 		ChatID: input.ID,
 	}

-	got := db2sdk.Chat(input, diffStatus)
+	fileRows := []database.GetChatFileMetadataByChatIDRow{
+		{
+			ID:             uuid.New(),
+			OwnerID:        input.OwnerID,
+			OrganizationID: uuid.New(),
+			Name:           "test.png",
+			Mimetype:       "image/png",
+			CreatedAt:      now,
+		},
+	}
+
+	got := db2sdk.Chat(input, diffStatus, fileRows)

 	v := reflect.ValueOf(got)
 	typ := v.Type()
 	// HasUnread is populated by ChatRows (which joins the
-	// read-cursor query), not by Chat, so it is expected
-	// to remain zero here.
-	skip := map[string]bool{"HasUnread": true}
+	// read-cursor query), not by Chat. Warnings is a transient
+	// field populated by handlers, not the converter. Both are
+	// expected to remain zero here.
+	skip := map[string]bool{"HasUnread": true, "Warnings": true}
 	for i := range typ.NumField() {
 		field := typ.Field(i)
 		if skip[field.Name] {
@@ -581,6 +593,112 @@ func TestChat_AllFieldsPopulated(t *testing.T) {
 	}
 }

+func TestChat_FileMetadataConversion(t *testing.T) {
+	t.Parallel()
+
+	ownerID := uuid.New()
+	orgID := uuid.New()
+	fileID := uuid.New()
+	now := dbtime.Now()
+
+	chat := database.Chat{
+		ID:                uuid.New(),
+		OwnerID:           ownerID,
+		LastModelConfigID: uuid.New(),
+		Title:             "file metadata test",
+		Status:            database.ChatStatusWaiting,
+		CreatedAt:         now,
+		UpdatedAt:         now,
+	}
+
+	rows := []database.GetChatFileMetadataByChatIDRow{
+		{
+			ID:             fileID,
+			OwnerID:        ownerID,
+			OrganizationID: orgID,
+			Name:           "screenshot.png",
+			Mimetype:       "image/png",
+			CreatedAt:      now,
+		},
+	}
+
+	result := db2sdk.Chat(chat, nil, rows)
+
+	require.Len(t, result.Files, 1)
+	f := result.Files[0]
+	require.Equal(t, fileID, f.ID)
+	require.Equal(t, ownerID, f.OwnerID, "OwnerID must be mapped from DB row")
+	require.Equal(t, orgID, f.OrganizationID, "OrganizationID must be mapped from DB row")
+	require.Equal(t, "screenshot.png", f.Name)
+	require.Equal(t, "image/png", f.MimeType)
+	require.Equal(t, now, f.CreatedAt)
+
+	// Verify JSON serialization uses snake_case for mime_type.
+	data, err := json.Marshal(f)
+	require.NoError(t, err)
+	require.Contains(t, string(data), `"mime_type"`)
+	require.NotContains(t, string(data), `"mimetype"`)
+}
+
+func TestChat_NilFilesOmitted(t *testing.T) {
+	t.Parallel()
+
+	chat := database.Chat{
+		ID:                uuid.New(),
+		OwnerID:           uuid.New(),
+		LastModelConfigID: uuid.New(),
+		Title:             "no files",
+		Status:            database.ChatStatusWaiting,
+		CreatedAt:         dbtime.Now(),
+		UpdatedAt:         dbtime.Now(),
+	}
+
+	result := db2sdk.Chat(chat, nil, nil)
+	require.Empty(t, result.Files)
+}
+
+func TestChat_MultipleFiles(t *testing.T) {
+	t.Parallel()
+
+	now := dbtime.Now()
+	file1 := uuid.New()
+	file2 := uuid.New()
+
+	chat := database.Chat{
+		ID:                uuid.New(),
+		OwnerID:           uuid.New(),
+		LastModelConfigID: uuid.New(),
+		Title:             "multi file test",
+		Status:            database.ChatStatusWaiting,
+		CreatedAt:         now,
+		UpdatedAt:         now,
+	}
+
+	rows := []database.GetChatFileMetadataByChatIDRow{
+		{
+			ID:             file1,
+			OwnerID:        chat.OwnerID,
+			OrganizationID: uuid.New(),
+			Name:           "a.png",
+			Mimetype:       "image/png",
+			CreatedAt:      now,
+		},
+		{
+			ID:             file2,
+			OwnerID:        chat.OwnerID,
+			OrganizationID: uuid.New(),
+			Name:           "b.txt",
+			Mimetype:       "text/plain",
+			CreatedAt:      now,
+		},
+	}
+
+	result := db2sdk.Chat(chat, nil, rows)
+	require.Len(t, result.Files, 2)
+	require.Equal(t, "a.png", result.Files[0].Name)
+	require.Equal(t, "b.txt", result.Files[1].Name)
+}
+
 func TestChatQueuedMessage_MalformedContent(t *testing.T) {
 	t.Parallel()

@@ -2583,6 +2583,10 @@ func (q *querier) GetChatFileByID(ctx context.Context, id uuid.UUID) (database.C
 	return file, nil
 }

+func (q *querier) GetChatFileMetadataByChatID(ctx context.Context, chatID uuid.UUID) ([]database.GetChatFileMetadataByChatIDRow, error) {
+	return fetchWithPostFilter(q.auth, policy.ActionRead, q.db.GetChatFileMetadataByChatID)(ctx, chatID)
+}
+
 func (q *querier) GetChatFilesByIDs(ctx context.Context, ids []uuid.UUID) ([]database.ChatFile, error) {
 	files, err := q.db.GetChatFilesByIDs(ctx, ids)
 	if err != nil {
@@ -5393,6 +5397,17 @@ func (q *querier) InsertWorkspaceResourceMetadata(ctx context.Context, arg datab
 	return q.db.InsertWorkspaceResourceMetadata(ctx, arg)
 }

+func (q *querier) LinkChatFiles(ctx context.Context, arg database.LinkChatFilesParams) (int32, error) {
+	chat, err := q.db.GetChatByID(ctx, arg.ChatID)
+	if err != nil {
+		return 0, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
+		return 0, err
+	}
+	return q.db.LinkChatFiles(ctx, arg)
+}
+
 func (q *querier) ListAIBridgeClients(ctx context.Context, arg database.ListAIBridgeClientsParams) ([]string, error) {
 	prep, err := prepareSQLFilter(ctx, q.auth, policy.ActionRead, rbac.ResourceAibridgeInterception.Type)
 	if err != nil {
@@ -5767,15 +5782,15 @@ func (q *querier) UpdateChatByID(ctx context.Context, arg database.UpdateChatByI
 	return q.db.UpdateChatByID(ctx, arg)
 }

-func (q *querier) UpdateChatHeartbeat(ctx context.Context, arg database.UpdateChatHeartbeatParams) (int64, error) {
-	chat, err := q.db.GetChatByID(ctx, arg.ID)
-	if err != nil {
-		return 0, err
+func (q *querier) UpdateChatHeartbeats(ctx context.Context, arg database.UpdateChatHeartbeatsParams) ([]uuid.UUID, error) {
+	// The batch heartbeat is a system-level operation filtered by
+	// worker_id. Authorization is enforced by the AsChatd context
+	// at the call site rather than per-row, because checking each
+	// row individually would defeat the purpose of batching.
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceChat); err != nil {
+		return nil, err
 	}
-	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
-		return 0, err
-	}
-	return q.db.UpdateChatHeartbeat(ctx, arg)
+	return q.db.UpdateChatHeartbeats(ctx, arg)
 }

 func (q *querier) UpdateChatLabelsByID(ctx context.Context, arg database.UpdateChatLabelsByIDParams) (database.Chat, error) {
@@ -400,6 +400,17 @@ func (s *MethodTestSuite) TestChats() {
 		dbm.EXPECT().UnarchiveChatByID(gomock.Any(), chat.ID).Return([]database.Chat{chat}, nil).AnyTimes()
 		check.Args(chat.ID).Asserts(chat, policy.ActionUpdate).Returns([]database.Chat{chat})
 	}))
+	s.Run("LinkChatFiles", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		arg := database.LinkChatFilesParams{
+			ChatID:       chat.ID,
+			MaxFileLinks: int32(codersdk.MaxChatFileIDs),
+			FileIds:      []uuid.UUID{uuid.New()},
+		}
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		dbm.EXPECT().LinkChatFiles(gomock.Any(), arg).Return(int32(0), nil).AnyTimes()
+		check.Args(arg).Asserts(chat, policy.ActionUpdate).Returns(int32(0))
+	}))
 	s.Run("PinChatByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		chat := testutil.Fake(s.T(), faker, database.Chat{})
 		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
@@ -576,6 +587,19 @@ func (s *MethodTestSuite) TestChats() {
 		dbm.EXPECT().GetChatFilesByIDs(gomock.Any(), []uuid.UUID{file.ID}).Return([]database.ChatFile{file}, nil).AnyTimes()
 		check.Args([]uuid.UUID{file.ID}).Asserts(rbac.ResourceChat.WithOwner(file.OwnerID.String()).InOrg(file.OrganizationID).WithID(file.ID), policy.ActionRead).Returns([]database.ChatFile{file})
 	}))
+	s.Run("GetChatFileMetadataByChatID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		file := testutil.Fake(s.T(), faker, database.ChatFile{})
+		rows := []database.GetChatFileMetadataByChatIDRow{{
+			ID:             file.ID,
+			Name:           file.Name,
+			Mimetype:       file.Mimetype,
+			CreatedAt:      file.CreatedAt,
+			OwnerID:        file.OwnerID,
+			OrganizationID: file.OrganizationID,
+		}}
+		dbm.EXPECT().GetChatFileMetadataByChatID(gomock.Any(), file.ID).Return(rows, nil).AnyTimes()
+		check.Args(file.ID).Asserts(rbac.ResourceChat.WithOwner(file.OwnerID.String()).InOrg(file.OrganizationID).WithID(file.ID), policy.ActionRead).Returns(rows)
+	}))
 	s.Run("GetChatMessageByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		chat := testutil.Fake(s.T(), faker, database.Chat{})
 		msg := testutil.Fake(s.T(), faker, database.ChatMessage{ChatID: chat.ID})
@@ -818,15 +842,15 @@ func (s *MethodTestSuite) TestChats() {
 		dbm.EXPECT().UpdateChatStatusPreserveUpdatedAt(gomock.Any(), arg).Return(chat, nil).AnyTimes()
 		check.Args(arg).Asserts(chat, policy.ActionUpdate).Returns(chat)
 	}))
-	s.Run("UpdateChatHeartbeat", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		chat := testutil.Fake(s.T(), faker, database.Chat{})
-		arg := database.UpdateChatHeartbeatParams{
-			ID:       chat.ID,
+	s.Run("UpdateChatHeartbeats", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		resultID := uuid.New()
+		arg := database.UpdateChatHeartbeatsParams{
+			IDs:      []uuid.UUID{resultID},
 			WorkerID: uuid.New(),
+			Now:      time.Now(),
 		}
-		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
-		dbm.EXPECT().UpdateChatHeartbeat(gomock.Any(), arg).Return(int64(1), nil).AnyTimes()
-		check.Args(arg).Asserts(chat, policy.ActionUpdate).Returns(int64(1))
+		dbm.EXPECT().UpdateChatHeartbeats(gomock.Any(), arg).Return([]uuid.UUID{resultID}, nil).AnyTimes()
+		check.Args(arg).Asserts(rbac.ResourceChat, policy.ActionUpdate).Returns([]uuid.UUID{resultID})
 	}))
 	s.Run("UpdateChatMessageByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		chat := testutil.Fake(s.T(), faker, database.Chat{})
@@ -1128,6 +1128,14 @@ func (m queryMetricsStore) GetChatFileByID(ctx context.Context, id uuid.UUID) (d
 	return r0, r1
 }

+func (m queryMetricsStore) GetChatFileMetadataByChatID(ctx context.Context, chatID uuid.UUID) ([]database.GetChatFileMetadataByChatIDRow, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatFileMetadataByChatID(ctx, chatID)
+	m.queryLatencies.WithLabelValues("GetChatFileMetadataByChatID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatFileMetadataByChatID").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetChatFilesByIDs(ctx context.Context, ids []uuid.UUID) ([]database.ChatFile, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetChatFilesByIDs(ctx, ids)
@@ -3776,6 +3784,14 @@ func (m queryMetricsStore) InsertWorkspaceResourceMetadata(ctx context.Context,
 	return r0, r1
 }

+func (m queryMetricsStore) LinkChatFiles(ctx context.Context, arg database.LinkChatFilesParams) (int32, error) {
+	start := time.Now()
+	r0, r1 := m.s.LinkChatFiles(ctx, arg)
+	m.queryLatencies.WithLabelValues("LinkChatFiles").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "LinkChatFiles").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) ListAIBridgeClients(ctx context.Context, arg database.ListAIBridgeClientsParams) ([]string, error) {
 	start := time.Now()
 	r0, r1 := m.s.ListAIBridgeClients(ctx, arg)
@@ -4120,11 +4136,11 @@ func (m queryMetricsStore) UpdateChatByID(ctx context.Context, arg database.Upda
 	return r0, r1
 }

-func (m queryMetricsStore) UpdateChatHeartbeat(ctx context.Context, arg database.UpdateChatHeartbeatParams) (int64, error) {
+func (m queryMetricsStore) UpdateChatHeartbeats(ctx context.Context, arg database.UpdateChatHeartbeatsParams) ([]uuid.UUID, error) {
 	start := time.Now()
-	r0, r1 := m.s.UpdateChatHeartbeat(ctx, arg)
-	m.queryLatencies.WithLabelValues("UpdateChatHeartbeat").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateChatHeartbeat").Inc()
+	r0, r1 := m.s.UpdateChatHeartbeats(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpdateChatHeartbeats").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateChatHeartbeats").Inc()
 	return r0, r1
 }

@@ -2072,6 +2072,21 @@ func (mr *MockStoreMockRecorder) GetChatFileByID(ctx, id any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatFileByID", reflect.TypeOf((*MockStore)(nil).GetChatFileByID), ctx, id)
 }

+// GetChatFileMetadataByChatID mocks base method.
+func (m *MockStore) GetChatFileMetadataByChatID(ctx context.Context, chatID uuid.UUID) ([]database.GetChatFileMetadataByChatIDRow, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatFileMetadataByChatID", ctx, chatID)
+	ret0, _ := ret[0].([]database.GetChatFileMetadataByChatIDRow)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatFileMetadataByChatID indicates an expected call of GetChatFileMetadataByChatID.
+func (mr *MockStoreMockRecorder) GetChatFileMetadataByChatID(ctx, chatID any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatFileMetadataByChatID", reflect.TypeOf((*MockStore)(nil).GetChatFileMetadataByChatID), ctx, chatID)
+}
+
 // GetChatFilesByIDs mocks base method.
 func (m *MockStore) GetChatFilesByIDs(ctx context.Context, ids []uuid.UUID) ([]database.ChatFile, error) {
 	m.ctrl.T.Helper()
@@ -7066,6 +7081,21 @@ func (mr *MockStoreMockRecorder) InsertWorkspaceResourceMetadata(ctx, arg any) *
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "InsertWorkspaceResourceMetadata", reflect.TypeOf((*MockStore)(nil).InsertWorkspaceResourceMetadata), ctx, arg)
 }

+// LinkChatFiles mocks base method.
+func (m *MockStore) LinkChatFiles(ctx context.Context, arg database.LinkChatFilesParams) (int32, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "LinkChatFiles", ctx, arg)
+	ret0, _ := ret[0].(int32)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// LinkChatFiles indicates an expected call of LinkChatFiles.
+func (mr *MockStoreMockRecorder) LinkChatFiles(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "LinkChatFiles", reflect.TypeOf((*MockStore)(nil).LinkChatFiles), ctx, arg)
+}
+
 // ListAIBridgeClients mocks base method.
 func (m *MockStore) ListAIBridgeClients(ctx context.Context, arg database.ListAIBridgeClientsParams) ([]string, error) {
 	m.ctrl.T.Helper()
@@ -7805,19 +7835,19 @@ func (mr *MockStoreMockRecorder) UpdateChatByID(ctx, arg any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateChatByID", reflect.TypeOf((*MockStore)(nil).UpdateChatByID), ctx, arg)
 }

-// UpdateChatHeartbeat mocks base method.
-func (m *MockStore) UpdateChatHeartbeat(ctx context.Context, arg database.UpdateChatHeartbeatParams) (int64, error) {
+// UpdateChatHeartbeats mocks base method.
+func (m *MockStore) UpdateChatHeartbeats(ctx context.Context, arg database.UpdateChatHeartbeatsParams) ([]uuid.UUID, error) {
 	m.ctrl.T.Helper()
-	ret := m.ctrl.Call(m, "UpdateChatHeartbeat", ctx, arg)
-	ret0, _ := ret[0].(int64)
+	ret := m.ctrl.Call(m, "UpdateChatHeartbeats", ctx, arg)
+	ret0, _ := ret[0].([]uuid.UUID)
 	ret1, _ := ret[1].(error)
 	return ret0, ret1
 }

-// UpdateChatHeartbeat indicates an expected call of UpdateChatHeartbeat.
-func (mr *MockStoreMockRecorder) UpdateChatHeartbeat(ctx, arg any) *gomock.Call {
+// UpdateChatHeartbeats indicates an expected call of UpdateChatHeartbeats.
+func (mr *MockStoreMockRecorder) UpdateChatHeartbeats(ctx, arg any) *gomock.Call {
 	mr.mock.ctrl.T.Helper()
-	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateChatHeartbeat", reflect.TypeOf((*MockStore)(nil).UpdateChatHeartbeat), ctx, arg)
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateChatHeartbeats", reflect.TypeOf((*MockStore)(nil).UpdateChatHeartbeats), ctx, arg)
 }

 // UpdateChatLabelsByID mocks base method.
@@ -1269,6 +1269,11 @@ CREATE TABLE chat_diff_statuses (
    head_branch text
 );

+CREATE TABLE chat_file_links (
+    chat_id uuid NOT NULL,
+    file_id uuid NOT NULL
+);
+
 CREATE TABLE chat_files (
    id uuid DEFAULT gen_random_uuid() NOT NULL,
    owner_id uuid NOT NULL,
@@ -3344,6 +3349,9 @@ ALTER TABLE ONLY boundary_usage_stats
 ALTER TABLE ONLY chat_diff_statuses
    ADD CONSTRAINT chat_diff_statuses_pkey PRIMARY KEY (chat_id);

+ALTER TABLE ONLY chat_file_links
+    ADD CONSTRAINT chat_file_links_chat_id_file_id_key UNIQUE (chat_id, file_id);
+
 ALTER TABLE ONLY chat_files
    ADD CONSTRAINT chat_files_pkey PRIMARY KEY (id);

@@ -3734,6 +3742,8 @@ CREATE INDEX idx_audit_logs_time_desc ON audit_logs USING btree ("time" DESC);

 CREATE INDEX idx_chat_diff_statuses_stale_at ON chat_diff_statuses USING btree (stale_at);

+CREATE INDEX idx_chat_file_links_chat_id ON chat_file_links USING btree (chat_id);
+
 CREATE INDEX idx_chat_files_org ON chat_files USING btree (organization_id);

 CREATE INDEX idx_chat_files_owner ON chat_files USING btree (owner_id);
@@ -4036,6 +4046,12 @@ ALTER TABLE ONLY api_keys
 ALTER TABLE ONLY chat_diff_statuses
    ADD CONSTRAINT chat_diff_statuses_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;

+ALTER TABLE ONLY chat_file_links
+    ADD CONSTRAINT chat_file_links_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
+
+ALTER TABLE ONLY chat_file_links
+    ADD CONSTRAINT chat_file_links_file_id_fkey FOREIGN KEY (file_id) REFERENCES chat_files(id) ON DELETE CASCADE;
+
 ALTER TABLE ONLY chat_files
    ADD CONSTRAINT chat_files_organization_id_fkey FOREIGN KEY (organization_id) REFERENCES organizations(id) ON DELETE CASCADE;

@@ -10,6 +10,8 @@ const (
 	ForeignKeyAibridgeInterceptionsInitiatorID                    ForeignKeyConstraint = "aibridge_interceptions_initiator_id_fkey"                        // ALTER TABLE ONLY aibridge_interceptions ADD CONSTRAINT aibridge_interceptions_initiator_id_fkey FOREIGN KEY (initiator_id) REFERENCES users(id);
 	ForeignKeyAPIKeysUserIDUUID                                   ForeignKeyConstraint = "api_keys_user_id_uuid_fkey"                                      // ALTER TABLE ONLY api_keys ADD CONSTRAINT api_keys_user_id_uuid_fkey FOREIGN KEY (user_id) REFERENCES users(id) ON DELETE CASCADE;
 	ForeignKeyChatDiffStatusesChatID                              ForeignKeyConstraint = "chat_diff_statuses_chat_id_fkey"                                 // ALTER TABLE ONLY chat_diff_statuses ADD CONSTRAINT chat_diff_statuses_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
+	ForeignKeyChatFileLinksChatID                                 ForeignKeyConstraint = "chat_file_links_chat_id_fkey"                                    // ALTER TABLE ONLY chat_file_links ADD CONSTRAINT chat_file_links_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
+	ForeignKeyChatFileLinksFileID                                 ForeignKeyConstraint = "chat_file_links_file_id_fkey"                                    // ALTER TABLE ONLY chat_file_links ADD CONSTRAINT chat_file_links_file_id_fkey FOREIGN KEY (file_id) REFERENCES chat_files(id) ON DELETE CASCADE;
 	ForeignKeyChatFilesOrganizationID                             ForeignKeyConstraint = "chat_files_organization_id_fkey"                                 // ALTER TABLE ONLY chat_files ADD CONSTRAINT chat_files_organization_id_fkey FOREIGN KEY (organization_id) REFERENCES organizations(id) ON DELETE CASCADE;
 	ForeignKeyChatFilesOwnerID                                    ForeignKeyConstraint = "chat_files_owner_id_fkey"                                        // ALTER TABLE ONLY chat_files ADD CONSTRAINT chat_files_owner_id_fkey FOREIGN KEY (owner_id) REFERENCES users(id) ON DELETE CASCADE;
 	ForeignKeyChatMessagesChatID                                  ForeignKeyConstraint = "chat_messages_chat_id_fkey"                                      // ALTER TABLE ONLY chat_messages ADD CONSTRAINT chat_messages_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
@@ -0,0 +1,9 @@
+ALTER TABLE chats ADD COLUMN file_ids uuid[] DEFAULT '{}'::uuid[] NOT NULL;
+
+UPDATE chats SET file_ids = (
+    SELECT COALESCE(array_agg(cfl.file_id), '{}')
+    FROM chat_file_links cfl
+    WHERE cfl.chat_id = chats.id
+);
+
+DROP TABLE chat_file_links;
@@ -0,0 +1,17 @@
+CREATE TABLE chat_file_links (
+    chat_id uuid NOT NULL,
+    file_id uuid NOT NULL,
+    UNIQUE (chat_id, file_id)
+);
+
+CREATE INDEX idx_chat_file_links_chat_id ON chat_file_links (chat_id);
+
+ALTER TABLE chat_file_links
+    ADD CONSTRAINT chat_file_links_chat_id_fkey
+    FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
+
+ALTER TABLE chat_file_links
+    ADD CONSTRAINT chat_file_links_file_id_fkey
+    FOREIGN KEY (file_id) REFERENCES chat_files(id) ON DELETE CASCADE;
+
+ALTER TABLE chats DROP COLUMN IF EXISTS file_ids;
@@ -0,0 +1,5 @@
+INSERT INTO chat_file_links (chat_id, file_id)
+VALUES (
+    '72c0438a-18eb-4688-ab80-e4c6a126ef96',
+    '00000000-0000-0000-0000-000000000099'
+);
@@ -187,6 +187,10 @@ func (c ChatFile) RBACObject() rbac.Object {
 	return rbac.ResourceChat.WithID(c.ID).WithOwner(c.OwnerID.String()).InOrg(c.OrganizationID)
 }

+func (c GetChatFileMetadataByChatIDRow) RBACObject() rbac.Object {
+	return rbac.ResourceChat.WithID(c.ID).WithOwner(c.OwnerID.String()).InOrg(c.OrganizationID)
+}
+
 func (s APIKeyScope) ToRBAC() rbac.ScopeName {
 	switch s {
 	case ApiKeyScopeCoderAll:
@@ -584,6 +584,7 @@ func (q *sqlQuerier) CountAuthorizedAuditLogs(ctx context.Context, arg CountAudi
 		arg.DateTo,
 		arg.BuildReason,
 		arg.RequestID,
+		arg.CountCap,
 	)
 	if err != nil {
 		return 0, err
@@ -720,6 +721,7 @@ func (q *sqlQuerier) CountAuthorizedConnectionLogs(ctx context.Context, arg Coun
 		arg.WorkspaceID,
 		arg.ConnectionID,
 		arg.Status,
+		arg.CountCap,
 	)
 	if err != nil {
 		return 0, err
@@ -145,5 +145,13 @@ func extractWhereClause(query string) string {
 	// Remove SQL comments
 	whereClause = regexp.MustCompile(`(?m)--.*$`).ReplaceAllString(whereClause, "")

+	// Normalize indentation so subquery wrapping doesn't cause
+	// mismatches.
+	lines := strings.Split(whereClause, "\n")
+	for i, line := range lines {
+		lines[i] = strings.TrimLeft(line, " \t")
+	}
+	whereClause = strings.Join(lines, "\n")
+
 	return strings.TrimSpace(whereClause)
 }
@@ -4218,6 +4218,11 @@ type ChatFile struct {
 	Data           []byte    `db:"data" json:"data"`
 }

+type ChatFileLink struct {
+	ChatID uuid.UUID `db:"chat_id" json:"chat_id"`
+	FileID uuid.UUID `db:"file_id" json:"file_id"`
+}
+
 type ChatMessage struct {
 	ID                  int64                 `db:"id" json:"id"`
 	ChatID              uuid.UUID             `db:"chat_id" json:"chat_id"`
@@ -244,6 +244,10 @@ type sqlcQuerier interface {
 	GetChatDiffStatusByChatID(ctx context.Context, chatID uuid.UUID) (ChatDiffStatus, error)
 	GetChatDiffStatusesByChatIDs(ctx context.Context, chatIds []uuid.UUID) ([]ChatDiffStatus, error)
 	GetChatFileByID(ctx context.Context, id uuid.UUID) (ChatFile, error)
+	// GetChatFileMetadataByChatID returns lightweight file metadata for
+	// all files linked to a chat. The data column is excluded to avoid
+	// loading file content.
+	GetChatFileMetadataByChatID(ctx context.Context, chatID uuid.UUID) ([]GetChatFileMetadataByChatIDRow, error)
 	GetChatFilesByIDs(ctx context.Context, ids []uuid.UUID) ([]ChatFile, error)
 	// GetChatIncludeDefaultSystemPrompt preserves the legacy default
 	// for deployments created before the explicit include-default toggle.
@@ -778,6 +782,15 @@ type sqlcQuerier interface {
 	InsertWorkspaceProxy(ctx context.Context, arg InsertWorkspaceProxyParams) (WorkspaceProxy, error)
 	InsertWorkspaceResource(ctx context.Context, arg InsertWorkspaceResourceParams) (WorkspaceResource, error)
 	InsertWorkspaceResourceMetadata(ctx context.Context, arg InsertWorkspaceResourceMetadataParams) ([]WorkspaceResourceMetadatum, error)
+	// LinkChatFiles inserts file associations into the chat_file_links
+	// join table with deduplication (ON CONFLICT DO NOTHING). The INSERT
+	// is conditional: it only proceeds when the total number of links
+	// (existing + genuinely new) does not exceed max_file_links. Returns
+	// the number of genuinely new file IDs that were NOT inserted due to
+	// the cap. A return value of 0 means all files were linked (or were
+	// already linked). A positive value means the cap blocked that many
+	// new links.
+	LinkChatFiles(ctx context.Context, arg LinkChatFilesParams) (int32, error)
 	ListAIBridgeClients(ctx context.Context, arg ListAIBridgeClientsParams) ([]string, error)
 	ListAIBridgeInterceptions(ctx context.Context, arg ListAIBridgeInterceptionsParams) ([]ListAIBridgeInterceptionsRow, error)
 	// Finds all unique AI Bridge interception telemetry summaries combinations
@@ -857,9 +870,11 @@ type sqlcQuerier interface {
 	UpdateAPIKeyByID(ctx context.Context, arg UpdateAPIKeyByIDParams) error
 	UpdateChatBuildAgentBinding(ctx context.Context, arg UpdateChatBuildAgentBindingParams) (Chat, error)
 	UpdateChatByID(ctx context.Context, arg UpdateChatByIDParams) (Chat, error)
-	// Bumps the heartbeat timestamp for a running chat so that other
-	// replicas know the worker is still alive.
-	UpdateChatHeartbeat(ctx context.Context, arg UpdateChatHeartbeatParams) (int64, error)
+	// Bumps the heartbeat timestamp for the given set of chat IDs,
+	// provided they are still running and owned by the specified
+	// worker. Returns the IDs that were actually updated so the
+	// caller can detect stolen or completed chats via set-difference.
+	UpdateChatHeartbeats(ctx context.Context, arg UpdateChatHeartbeatsParams) ([]uuid.UUID, error)
 	UpdateChatLabelsByID(ctx context.Context, arg UpdateChatLabelsByIDParams) (Chat, error)
 	// Updates the cached injected context parts (AGENTS.md +
 	// skills) on the chat row. Called only when context changes
@@ -2275,93 +2275,105 @@ func (q *sqlQuerier) UpdateAPIKeyByID(ctx context.Context, arg UpdateAPIKeyByIDP
 }

 const countAuditLogs = `-- name: CountAuditLogs :one
-SELECT COUNT(*)
-FROM audit_logs
-	LEFT JOIN users ON audit_logs.user_id = users.id
-	LEFT JOIN organizations ON audit_logs.organization_id = organizations.id
-	-- First join on workspaces to get the initial workspace create
-	-- to workspace build 1 id. This is because the first create is
-	-- is a different audit log than subsequent starts.
-	LEFT JOIN workspaces ON audit_logs.resource_type = 'workspace'
-	AND audit_logs.resource_id = workspaces.id
-	-- Get the reason from the build if the resource type
-	-- is a workspace_build
-	LEFT JOIN workspace_builds wb_build ON audit_logs.resource_type = 'workspace_build'
-	AND audit_logs.resource_id = wb_build.id
-	-- Get the reason from the build #1 if this is the first
-	-- workspace create.
-	LEFT JOIN workspace_builds wb_workspace ON audit_logs.resource_type = 'workspace'
-	AND audit_logs.action = 'create'
-	AND workspaces.id = wb_workspace.workspace_id
-	AND wb_workspace.build_number = 1
-WHERE
-	-- Filter resource_type
-	CASE
-		WHEN $1::text != '' THEN resource_type = $1::resource_type
-		ELSE true
-	END
-	-- Filter resource_id
-	AND CASE
-		WHEN $2::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN resource_id = $2
-		ELSE true
-	END
-	-- Filter organization_id
-	AND CASE
-		WHEN $3::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN audit_logs.organization_id = $3
-		ELSE true
-	END
-	-- Filter by resource_target
-	AND CASE
-		WHEN $4::text != '' THEN resource_target = $4
-		ELSE true
-	END
-	-- Filter action
-	AND CASE
-		WHEN $5::text != '' THEN action = $5::audit_action
-		ELSE true
-	END
-	-- Filter by user_id
-	AND CASE
-		WHEN $6::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN user_id = $6
-		ELSE true
-	END
-	-- Filter by username
-	AND CASE
-		WHEN $7::text != '' THEN user_id = (
-			SELECT id
-			FROM users
-			WHERE lower(username) = lower($7)
-				AND deleted = false
-		)
-		ELSE true
-	END
-	-- Filter by user_email
-	AND CASE
-		WHEN $8::text != '' THEN users.email = $8
-		ELSE true
-	END
-	-- Filter by date_from
-	AND CASE
-		WHEN $9::timestamp with time zone != '0001-01-01 00:00:00Z' THEN "time" >= $9
-		ELSE true
-	END
-	-- Filter by date_to
-	AND CASE
-		WHEN $10::timestamp with time zone != '0001-01-01 00:00:00Z' THEN "time" <= $10
-		ELSE true
-	END
-	-- Filter by build_reason
-	AND CASE
-		WHEN $11::text != '' THEN COALESCE(wb_build.reason::text, wb_workspace.reason::text) = $11
-		ELSE true
-	END
-	-- Filter request_id
-	AND CASE
-		WHEN $12::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN audit_logs.request_id = $12
-		ELSE true
-	END
-	-- Authorize Filter clause will be injected below in CountAuthorizedAuditLogs
-	-- @authorize_filter
+SELECT COUNT(*) FROM (
+	SELECT 1
+	FROM audit_logs
+		LEFT JOIN users ON audit_logs.user_id = users.id
+		LEFT JOIN organizations ON audit_logs.organization_id = organizations.id
+		-- First join on workspaces to get the initial workspace create
+		-- to workspace build 1 id. This is because the first create is
+		-- is a different audit log than subsequent starts.
+		LEFT JOIN workspaces ON audit_logs.resource_type = 'workspace'
+		AND audit_logs.resource_id = workspaces.id
+		-- Get the reason from the build if the resource type
+		-- is a workspace_build
+		LEFT JOIN workspace_builds wb_build ON audit_logs.resource_type = 'workspace_build'
+		AND audit_logs.resource_id = wb_build.id
+		-- Get the reason from the build #1 if this is the first
+		-- workspace create.
+		LEFT JOIN workspace_builds wb_workspace ON audit_logs.resource_type = 'workspace'
+		AND audit_logs.action = 'create'
+		AND workspaces.id = wb_workspace.workspace_id
+		AND wb_workspace.build_number = 1
+	WHERE
+		-- Filter resource_type
+		CASE
+			WHEN $1::text != '' THEN resource_type = $1::resource_type
+			ELSE true
+		END
+		-- Filter resource_id
+		AND CASE
+			WHEN $2::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN resource_id = $2
+			ELSE true
+		END
+		-- Filter organization_id
+		AND CASE
+			WHEN $3::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN audit_logs.organization_id = $3
+			ELSE true
+		END
+		-- Filter by resource_target
+		AND CASE
+			WHEN $4::text != '' THEN resource_target = $4
+			ELSE true
+		END
+		-- Filter action
+		AND CASE
+			WHEN $5::text != '' THEN action = $5::audit_action
+			ELSE true
+		END
+		-- Filter by user_id
+		AND CASE
+			WHEN $6::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN user_id = $6
+			ELSE true
+		END
+		-- Filter by username
+		AND CASE
+			WHEN $7::text != '' THEN user_id = (
+				SELECT id
+				FROM users
+				WHERE lower(username) = lower($7)
+					AND deleted = false
+			)
+			ELSE true
+		END
+		-- Filter by user_email
+		AND CASE
+			WHEN $8::text != '' THEN users.email = $8
+			ELSE true
+		END
+		-- Filter by date_from
+		AND CASE
+			WHEN $9::timestamp with time zone != '0001-01-01 00:00:00Z' THEN "time" >= $9
+			ELSE true
+		END
+		-- Filter by date_to
+		AND CASE
+			WHEN $10::timestamp with time zone != '0001-01-01 00:00:00Z' THEN "time" <= $10
+			ELSE true
+		END
+		-- Filter by build_reason
+		AND CASE
+			WHEN $11::text != '' THEN COALESCE(wb_build.reason::text, wb_workspace.reason::text) = $11
+			ELSE true
+		END
+		-- Filter request_id
+		AND CASE
+			WHEN $12::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN audit_logs.request_id = $12
+			ELSE true
+		END
+		-- Authorize Filter clause will be injected below in CountAuthorizedAuditLogs
+		-- @authorize_filter
+	-- Avoid a slow scan on a large table with joins. The caller
+	-- passes the count cap and we add 1 so the frontend can detect
+	-- capping and show "... of N+". A cap of 0 means no limit (NULLIF
+	-- -> NULL + 1 = NULL).
+	-- NOTE: Parameterizing this so that we can easily change from,
+	-- e.g., 2000 to 5000. However, use literal NULL (or no LIMIT)
+	-- here if disabling the capping on a large table permanently.
+	-- This way the PG planner can plan parallel execution for
+	-- potential large wins.
+	LIMIT NULLIF($13::int, 0) + 1
+) AS limited_count
 `

 type CountAuditLogsParams struct {
@@ -2377,6 +2389,7 @@ type CountAuditLogsParams struct {
 	DateTo         time.Time `db:"date_to" json:"date_to"`
 	BuildReason    string    `db:"build_reason" json:"build_reason"`
 	RequestID      uuid.UUID `db:"request_id" json:"request_id"`
+	CountCap       int32     `db:"count_cap" json:"count_cap"`
 }

 func (q *sqlQuerier) CountAuditLogs(ctx context.Context, arg CountAuditLogsParams) (int64, error) {
@@ -2393,6 +2406,7 @@ func (q *sqlQuerier) CountAuditLogs(ctx context.Context, arg CountAuditLogsParam
 		arg.DateTo,
 		arg.BuildReason,
 		arg.RequestID,
+		arg.CountCap,
 	)
 	var count int64
 	err := row.Scan(&count)
@@ -2889,6 +2903,56 @@ func (q *sqlQuerier) GetChatFileByID(ctx context.Context, id uuid.UUID) (ChatFil
 	return i, err
 }

+const getChatFileMetadataByChatID = `-- name: GetChatFileMetadataByChatID :many
+SELECT cf.id, cf.owner_id, cf.organization_id, cf.name, cf.mimetype, cf.created_at
+FROM chat_files cf
+JOIN chat_file_links cfl ON cfl.file_id = cf.id
+WHERE cfl.chat_id = $1::uuid
+ORDER BY cf.created_at ASC
+`
+
+type GetChatFileMetadataByChatIDRow struct {
+	ID             uuid.UUID `db:"id" json:"id"`
+	OwnerID        uuid.UUID `db:"owner_id" json:"owner_id"`
+	OrganizationID uuid.UUID `db:"organization_id" json:"organization_id"`
+	Name           string    `db:"name" json:"name"`
+	Mimetype       string    `db:"mimetype" json:"mimetype"`
+	CreatedAt      time.Time `db:"created_at" json:"created_at"`
+}
+
+// GetChatFileMetadataByChatID returns lightweight file metadata for
+// all files linked to a chat. The data column is excluded to avoid
+// loading file content.
+func (q *sqlQuerier) GetChatFileMetadataByChatID(ctx context.Context, chatID uuid.UUID) ([]GetChatFileMetadataByChatIDRow, error) {
+	rows, err := q.db.QueryContext(ctx, getChatFileMetadataByChatID, chatID)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []GetChatFileMetadataByChatIDRow
+	for rows.Next() {
+		var i GetChatFileMetadataByChatIDRow
+		if err := rows.Scan(
+			&i.ID,
+			&i.OwnerID,
+			&i.OrganizationID,
+			&i.Name,
+			&i.Mimetype,
+			&i.CreatedAt,
+		); err != nil {
+			return nil, err
+		}
+		items = append(items, i)
+	}
+	if err := rows.Close(); err != nil {
+		return nil, err
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
+
 const getChatFilesByIDs = `-- name: GetChatFilesByIDs :many
 SELECT id, owner_id, organization_id, created_at, name, mimetype, data FROM chat_files WHERE id = ANY($1::uuid[])
 `
@@ -4530,7 +4594,8 @@ WITH chat_costs AS (
        COALESCE(SUM(cm.input_tokens), 0)::bigint AS total_input_tokens,
        COALESCE(SUM(cm.output_tokens), 0)::bigint AS total_output_tokens,
        COALESCE(SUM(cm.cache_read_tokens), 0)::bigint AS total_cache_read_tokens,
-        COALESCE(SUM(cm.cache_creation_tokens), 0)::bigint AS total_cache_creation_tokens
+        COALESCE(SUM(cm.cache_creation_tokens), 0)::bigint AS total_cache_creation_tokens,
+        COALESCE(SUM(cm.runtime_ms), 0)::bigint AS total_runtime_ms
    FROM chat_messages cm
    JOIN chats c ON c.id = cm.chat_id
    WHERE c.owner_id = $1::uuid
@@ -4547,7 +4612,8 @@ SELECT
    cc.total_input_tokens,
    cc.total_output_tokens,
    cc.total_cache_read_tokens,
-    cc.total_cache_creation_tokens
+    cc.total_cache_creation_tokens,
+    cc.total_runtime_ms
 FROM chat_costs cc
 LEFT JOIN chats rc ON rc.id = cc.root_chat_id
 ORDER BY cc.total_cost_micros DESC
@@ -4568,6 +4634,7 @@ type GetChatCostPerChatRow struct {
 	TotalOutputTokens        int64     `db:"total_output_tokens" json:"total_output_tokens"`
 	TotalCacheReadTokens     int64     `db:"total_cache_read_tokens" json:"total_cache_read_tokens"`
 	TotalCacheCreationTokens int64     `db:"total_cache_creation_tokens" json:"total_cache_creation_tokens"`
+	TotalRuntimeMs           int64     `db:"total_runtime_ms" json:"total_runtime_ms"`
 }

 // Per-root-chat cost breakdown for a single user within a date range.
@@ -4591,6 +4658,7 @@ func (q *sqlQuerier) GetChatCostPerChat(ctx context.Context, arg GetChatCostPerC
 			&i.TotalOutputTokens,
 			&i.TotalCacheReadTokens,
 			&i.TotalCacheCreationTokens,
+			&i.TotalRuntimeMs,
 		); err != nil {
 			return nil, err
 		}
@@ -4622,7 +4690,8 @@ SELECT
    COALESCE(SUM(cm.input_tokens), 0)::bigint AS total_input_tokens,
    COALESCE(SUM(cm.output_tokens), 0)::bigint AS total_output_tokens,
    COALESCE(SUM(cm.cache_read_tokens), 0)::bigint AS total_cache_read_tokens,
-    COALESCE(SUM(cm.cache_creation_tokens), 0)::bigint AS total_cache_creation_tokens
+    COALESCE(SUM(cm.cache_creation_tokens), 0)::bigint AS total_cache_creation_tokens,
+    COALESCE(SUM(cm.runtime_ms), 0)::bigint AS total_runtime_ms
 FROM
    chat_messages cm
 JOIN
@@ -4657,6 +4726,7 @@ type GetChatCostPerModelRow struct {
 	TotalOutputTokens        int64     `db:"total_output_tokens" json:"total_output_tokens"`
 	TotalCacheReadTokens     int64     `db:"total_cache_read_tokens" json:"total_cache_read_tokens"`
 	TotalCacheCreationTokens int64     `db:"total_cache_creation_tokens" json:"total_cache_creation_tokens"`
+	TotalRuntimeMs           int64     `db:"total_runtime_ms" json:"total_runtime_ms"`
 }

 // Per-model cost breakdown for a single user within a date range.
@@ -4681,6 +4751,7 @@ func (q *sqlQuerier) GetChatCostPerModel(ctx context.Context, arg GetChatCostPer
 			&i.TotalOutputTokens,
 			&i.TotalCacheReadTokens,
 			&i.TotalCacheCreationTokens,
+			&i.TotalRuntimeMs,
 		); err != nil {
 			return nil, err
 		}
@@ -4714,7 +4785,8 @@ WITH chat_cost_users AS (
        COALESCE(SUM(cm.input_tokens), 0)::bigint AS total_input_tokens,
        COALESCE(SUM(cm.output_tokens), 0)::bigint AS total_output_tokens,
        COALESCE(SUM(cm.cache_read_tokens), 0)::bigint AS total_cache_read_tokens,
-        COALESCE(SUM(cm.cache_creation_tokens), 0)::bigint AS total_cache_creation_tokens
+        COALESCE(SUM(cm.cache_creation_tokens), 0)::bigint AS total_cache_creation_tokens,
+        COALESCE(SUM(cm.runtime_ms), 0)::bigint AS total_runtime_ms
    FROM
        chat_messages cm
    JOIN
@@ -4748,6 +4820,7 @@ SELECT
    total_output_tokens,
    total_cache_read_tokens,
    total_cache_creation_tokens,
+    total_runtime_ms,
    COUNT(*) OVER()::bigint AS total_count
 FROM
    chat_cost_users
@@ -4780,6 +4853,7 @@ type GetChatCostPerUserRow struct {
 	TotalOutputTokens        int64     `db:"total_output_tokens" json:"total_output_tokens"`
 	TotalCacheReadTokens     int64     `db:"total_cache_read_tokens" json:"total_cache_read_tokens"`
 	TotalCacheCreationTokens int64     `db:"total_cache_creation_tokens" json:"total_cache_creation_tokens"`
+	TotalRuntimeMs           int64     `db:"total_runtime_ms" json:"total_runtime_ms"`
 	TotalCount               int64     `db:"total_count" json:"total_count"`
 }

@@ -4812,6 +4886,7 @@ func (q *sqlQuerier) GetChatCostPerUser(ctx context.Context, arg GetChatCostPerU
 			&i.TotalOutputTokens,
 			&i.TotalCacheReadTokens,
 			&i.TotalCacheCreationTokens,
+			&i.TotalRuntimeMs,
 			&i.TotalCount,
 		); err != nil {
 			return nil, err
@@ -4846,7 +4921,8 @@ SELECT
    COALESCE(SUM(cm.input_tokens), 0)::bigint AS total_input_tokens,
    COALESCE(SUM(cm.output_tokens), 0)::bigint AS total_output_tokens,
    COALESCE(SUM(cm.cache_read_tokens), 0)::bigint AS total_cache_read_tokens,
-    COALESCE(SUM(cm.cache_creation_tokens), 0)::bigint AS total_cache_creation_tokens
+    COALESCE(SUM(cm.cache_creation_tokens), 0)::bigint AS total_cache_creation_tokens,
+    COALESCE(SUM(cm.runtime_ms), 0)::bigint AS total_runtime_ms
 FROM
    chat_messages cm
 JOIN
@@ -4872,6 +4948,7 @@ type GetChatCostSummaryRow struct {
 	TotalOutputTokens        int64 `db:"total_output_tokens" json:"total_output_tokens"`
 	TotalCacheReadTokens     int64 `db:"total_cache_read_tokens" json:"total_cache_read_tokens"`
 	TotalCacheCreationTokens int64 `db:"total_cache_creation_tokens" json:"total_cache_creation_tokens"`
+	TotalRuntimeMs           int64 `db:"total_runtime_ms" json:"total_runtime_ms"`
 }

 // Aggregate cost summary for a single user within a date range.
@@ -4887,6 +4964,7 @@ func (q *sqlQuerier) GetChatCostSummary(ctx context.Context, arg GetChatCostSumm
 		&i.TotalOutputTokens,
 		&i.TotalCacheReadTokens,
 		&i.TotalCacheCreationTokens,
+		&i.TotalRuntimeMs,
 	)
 	return i, err
 }
@@ -6019,6 +6097,57 @@ func (q *sqlQuerier) InsertChatQueuedMessage(ctx context.Context, arg InsertChat
 	return i, err
 }

+const linkChatFiles = `-- name: LinkChatFiles :one
+WITH current AS (
+    SELECT COUNT(*) AS cnt
+    FROM chat_file_links
+    WHERE chat_id = $1::uuid
+),
+new_links AS (
+    SELECT $1::uuid AS chat_id, unnest($2::uuid[]) AS file_id
+),
+genuinely_new AS (
+    SELECT nl.chat_id, nl.file_id
+    FROM new_links nl
+    WHERE NOT EXISTS (
+        SELECT 1 FROM chat_file_links cfl
+        WHERE cfl.chat_id = nl.chat_id AND cfl.file_id = nl.file_id
+    )
+),
+inserted AS (
+    INSERT INTO chat_file_links (chat_id, file_id)
+    SELECT gn.chat_id, gn.file_id
+    FROM genuinely_new gn, current c
+    WHERE c.cnt + (SELECT COUNT(*) FROM genuinely_new) <= $3::int
+    ON CONFLICT (chat_id, file_id) DO NOTHING
+    RETURNING file_id
+)
+SELECT
+    (SELECT COUNT(*)::int FROM genuinely_new) -
+    (SELECT COUNT(*)::int FROM inserted) AS rejected_new_files
+`
+
+type LinkChatFilesParams struct {
+	ChatID       uuid.UUID   `db:"chat_id" json:"chat_id"`
+	FileIds      []uuid.UUID `db:"file_ids" json:"file_ids"`
+	MaxFileLinks int32       `db:"max_file_links" json:"max_file_links"`
+}
+
+// LinkChatFiles inserts file associations into the chat_file_links
+// join table with deduplication (ON CONFLICT DO NOTHING). The INSERT
+// is conditional: it only proceeds when the total number of links
+// (existing + genuinely new) does not exceed max_file_links. Returns
+// the number of genuinely new file IDs that were NOT inserted due to
+// the cap. A return value of 0 means all files were linked (or were
+// already linked). A positive value means the cap blocked that many
+// new links.
+func (q *sqlQuerier) LinkChatFiles(ctx context.Context, arg LinkChatFilesParams) (int32, error) {
+	row := q.db.QueryRowContext(ctx, linkChatFiles, arg.ChatID, pq.Array(arg.FileIds), arg.MaxFileLinks)
+	var rejected_new_files int32
+	err := row.Scan(&rejected_new_files)
+	return rejected_new_files, err
+}
+
 const listChatUsageLimitGroupOverrides = `-- name: ListChatUsageLimitGroupOverrides :many
 SELECT
    g.id AS group_id,
@@ -6486,30 +6615,49 @@ func (q *sqlQuerier) UpdateChatByID(ctx context.Context, arg UpdateChatByIDParam
 	return i, err
 }

-const updateChatHeartbeat = `-- name: UpdateChatHeartbeat :execrows
+const updateChatHeartbeats = `-- name: UpdateChatHeartbeats :many
 UPDATE
    chats
 SET
-    heartbeat_at = NOW()
+    heartbeat_at = $1::timestamptz
 WHERE
-    id = $1::uuid
-    AND worker_id = $2::uuid
+    id = ANY($2::uuid[])
+    AND worker_id = $3::uuid
    AND status = 'running'::chat_status
+RETURNING id
 `

-type UpdateChatHeartbeatParams struct {
-	ID       uuid.UUID `db:"id" json:"id"`
-	WorkerID uuid.UUID `db:"worker_id" json:"worker_id"`
+type UpdateChatHeartbeatsParams struct {
+	Now      time.Time   `db:"now" json:"now"`
+	IDs      []uuid.UUID `db:"ids" json:"ids"`
+	WorkerID uuid.UUID   `db:"worker_id" json:"worker_id"`
 }

-// Bumps the heartbeat timestamp for a running chat so that other
-// replicas know the worker is still alive.
-func (q *sqlQuerier) UpdateChatHeartbeat(ctx context.Context, arg UpdateChatHeartbeatParams) (int64, error) {
-	result, err := q.db.ExecContext(ctx, updateChatHeartbeat, arg.ID, arg.WorkerID)
+// Bumps the heartbeat timestamp for the given set of chat IDs,
+// provided they are still running and owned by the specified
+// worker. Returns the IDs that were actually updated so the
+// caller can detect stolen or completed chats via set-difference.
+func (q *sqlQuerier) UpdateChatHeartbeats(ctx context.Context, arg UpdateChatHeartbeatsParams) ([]uuid.UUID, error) {
+	rows, err := q.db.QueryContext(ctx, updateChatHeartbeats, arg.Now, pq.Array(arg.IDs), arg.WorkerID)
 	if err != nil {
-		return 0, err
+		return nil, err
 	}
-	return result.RowsAffected()
+	defer rows.Close()
+	var items []uuid.UUID
+	for rows.Next() {
+		var id uuid.UUID
+		if err := rows.Scan(&id); err != nil {
+			return nil, err
+		}
+		items = append(items, id)
+	}
+	if err := rows.Close(); err != nil {
+		return nil, err
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
 }

 const updateChatLabelsByID = `-- name: UpdateChatLabelsByID :one
@@ -7456,110 +7604,113 @@ func (q *sqlQuerier) BatchUpsertConnectionLogs(ctx context.Context, arg BatchUps
 }

 const countConnectionLogs = `-- name: CountConnectionLogs :one
-SELECT
-	COUNT(*) AS count
-FROM
-	connection_logs
-JOIN users AS workspace_owner ON
-	connection_logs.workspace_owner_id = workspace_owner.id
-LEFT JOIN users ON
-	connection_logs.user_id = users.id
-JOIN organizations ON
-	connection_logs.organization_id = organizations.id
-WHERE
-	-- Filter organization_id
-	CASE
-		WHEN $1 :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
-			connection_logs.organization_id = $1
-		ELSE true
-	END
-	-- Filter by workspace owner username
-	AND CASE
-		WHEN $2 :: text != '' THEN
-			workspace_owner_id = (
-				SELECT id FROM users
-				WHERE lower(username) = lower($2) AND deleted = false
-			)
-		ELSE true
-	END
-	-- Filter by workspace_owner_id
-	AND CASE
-		WHEN $3 :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
-			workspace_owner_id = $3
-		ELSE true
-	END
-	-- Filter by workspace_owner_email
-	AND CASE
-		WHEN $4 :: text != '' THEN
-			workspace_owner_id = (
-				SELECT id FROM users
-				WHERE email = $4 AND deleted = false
-			)
-		ELSE true
-	END
-	-- Filter by type
-	AND CASE
-		WHEN $5 :: text != '' THEN
-			type = $5 :: connection_type
-		ELSE true
-	END
-	-- Filter by user_id
-	AND CASE
-		WHEN $6 :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
-			user_id = $6
-		ELSE true
-	END
-	-- Filter by username
-	AND CASE
-		WHEN $7 :: text != '' THEN
-			user_id = (
-				SELECT id FROM users
-				WHERE lower(username) = lower($7) AND deleted = false
-			)
-		ELSE true
-	END
-	-- Filter by user_email
-	AND CASE
-		WHEN $8 :: text != '' THEN
-			users.email = $8
-		ELSE true
-	END
-	-- Filter by connected_after
-	AND CASE
-		WHEN $9 :: timestamp with time zone != '0001-01-01 00:00:00Z' THEN
-			connect_time >= $9
-		ELSE true
-	END
-	-- Filter by connected_before
-	AND CASE
-		WHEN $10 :: timestamp with time zone != '0001-01-01 00:00:00Z' THEN
-			connect_time <= $10
-		ELSE true
-	END
-	-- Filter by workspace_id
-	AND CASE
-		WHEN $11 :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
-			connection_logs.workspace_id = $11
-		ELSE true
-	END
-	-- Filter by connection_id
-	AND CASE
-		WHEN $12 :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
-			connection_logs.connection_id = $12
-		ELSE true
-	END
-	-- Filter by whether the session has a disconnect_time
-	AND CASE
-		WHEN $13 :: text != '' THEN
-			(($13 = 'ongoing' AND disconnect_time IS NULL) OR
-			($13 = 'completed' AND disconnect_time IS NOT NULL)) AND
-			-- Exclude web events, since we don't know their close time.
-			"type" NOT IN ('workspace_app', 'port_forwarding')
-		ELSE true
-	END
-	-- Authorize Filter clause will be injected below in
-	-- CountAuthorizedConnectionLogs
-	-- @authorize_filter
+SELECT COUNT(*) AS count FROM (
+	SELECT 1
+	FROM
+		connection_logs
+	JOIN users AS workspace_owner ON
+		connection_logs.workspace_owner_id = workspace_owner.id
+	LEFT JOIN users ON
+		connection_logs.user_id = users.id
+	JOIN organizations ON
+		connection_logs.organization_id = organizations.id
+	WHERE
+		-- Filter organization_id
+		CASE
+			WHEN $1 :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
+				connection_logs.organization_id = $1
+			ELSE true
+		END
+		-- Filter by workspace owner username
+		AND CASE
+			WHEN $2 :: text != '' THEN
+				workspace_owner_id = (
+					SELECT id FROM users
+					WHERE lower(username) = lower($2) AND deleted = false
+				)
+			ELSE true
+		END
+		-- Filter by workspace_owner_id
+		AND CASE
+			WHEN $3 :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
+				workspace_owner_id = $3
+			ELSE true
+		END
+		-- Filter by workspace_owner_email
+		AND CASE
+			WHEN $4 :: text != '' THEN
+				workspace_owner_id = (
+					SELECT id FROM users
+					WHERE email = $4 AND deleted = false
+				)
+			ELSE true
+		END
+		-- Filter by type
+		AND CASE
+			WHEN $5 :: text != '' THEN
+				type = $5 :: connection_type
+			ELSE true
+		END
+		-- Filter by user_id
+		AND CASE
+			WHEN $6 :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
+				user_id = $6
+			ELSE true
+		END
+		-- Filter by username
+		AND CASE
+			WHEN $7 :: text != '' THEN
+				user_id = (
+					SELECT id FROM users
+					WHERE lower(username) = lower($7) AND deleted = false
+				)
+			ELSE true
+		END
+		-- Filter by user_email
+		AND CASE
+			WHEN $8 :: text != '' THEN
+				users.email = $8
+			ELSE true
+		END
+		-- Filter by connected_after
+		AND CASE
+			WHEN $9 :: timestamp with time zone != '0001-01-01 00:00:00Z' THEN
+				connect_time >= $9
+			ELSE true
+		END
+		-- Filter by connected_before
+		AND CASE
+			WHEN $10 :: timestamp with time zone != '0001-01-01 00:00:00Z' THEN
+				connect_time <= $10
+			ELSE true
+		END
+		-- Filter by workspace_id
+		AND CASE
+			WHEN $11 :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
+				connection_logs.workspace_id = $11
+			ELSE true
+		END
+		-- Filter by connection_id
+		AND CASE
+			WHEN $12 :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
+				connection_logs.connection_id = $12
+			ELSE true
+		END
+		-- Filter by whether the session has a disconnect_time
+		AND CASE
+			WHEN $13 :: text != '' THEN
+				(($13 = 'ongoing' AND disconnect_time IS NULL) OR
+				($13 = 'completed' AND disconnect_time IS NOT NULL)) AND
+				-- Exclude web events, since we don't know their close time.
+				"type" NOT IN ('workspace_app', 'port_forwarding')
+			ELSE true
+		END
+		-- Authorize Filter clause will be injected below in
+		-- CountAuthorizedConnectionLogs
+		-- @authorize_filter
+	-- NOTE: See the CountAuditLogs LIMIT note.
+	LIMIT NULLIF($14::int, 0) + 1
+) AS limited_count
 `

 type CountConnectionLogsParams struct {
@@ -7576,6 +7727,7 @@ type CountConnectionLogsParams struct {
 	WorkspaceID         uuid.UUID `db:"workspace_id" json:"workspace_id"`
 	ConnectionID        uuid.UUID `db:"connection_id" json:"connection_id"`
 	Status              string    `db:"status" json:"status"`
+	CountCap            int32     `db:"count_cap" json:"count_cap"`
 }

 func (q *sqlQuerier) CountConnectionLogs(ctx context.Context, arg CountConnectionLogsParams) (int64, error) {
@@ -7593,6 +7745,7 @@ func (q *sqlQuerier) CountConnectionLogs(ctx context.Context, arg CountConnectio
 		arg.WorkspaceID,
 		arg.ConnectionID,
 		arg.Status,
+		arg.CountCap,
 	)
 	var count int64
 	err := row.Scan(&count)
@@ -149,94 +149,105 @@ VALUES (
 RETURNING *;

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

 -- name: DeleteOldAuditLogConnectionEvents :exec
 DELETE FROM audit_logs
@@ -8,3 +8,13 @@ SELECT * FROM chat_files WHERE id = @id::uuid;

 -- name: GetChatFilesByIDs :many
 SELECT * FROM chat_files WHERE id = ANY(@ids::uuid[]);
+
+-- name: GetChatFileMetadataByChatID :many
+-- GetChatFileMetadataByChatID returns lightweight file metadata for
+-- all files linked to a chat. The data column is excluded to avoid
+-- loading file content.
+SELECT cf.id, cf.owner_id, cf.organization_id, cf.name, cf.mimetype, cf.created_at
+FROM chat_files cf
+JOIN chat_file_links cfl ON cfl.file_id = cf.id
+WHERE cfl.chat_id = @chat_id::uuid
+ORDER BY cf.created_at ASC;
@@ -567,6 +567,43 @@ WHERE
 RETURNING
    *;

+-- name: LinkChatFiles :one
+-- LinkChatFiles inserts file associations into the chat_file_links
+-- join table with deduplication (ON CONFLICT DO NOTHING). The INSERT
+-- is conditional: it only proceeds when the total number of links
+-- (existing + genuinely new) does not exceed max_file_links. Returns
+-- the number of genuinely new file IDs that were NOT inserted due to
+-- the cap. A return value of 0 means all files were linked (or were
+-- already linked). A positive value means the cap blocked that many
+-- new links.
+WITH current AS (
+    SELECT COUNT(*) AS cnt
+    FROM chat_file_links
+    WHERE chat_id = @chat_id::uuid
+),
+new_links AS (
+    SELECT @chat_id::uuid AS chat_id, unnest(@file_ids::uuid[]) AS file_id
+),
+genuinely_new AS (
+    SELECT nl.chat_id, nl.file_id
+    FROM new_links nl
+    WHERE NOT EXISTS (
+        SELECT 1 FROM chat_file_links cfl
+        WHERE cfl.chat_id = nl.chat_id AND cfl.file_id = nl.file_id
+    )
+),
+inserted AS (
+    INSERT INTO chat_file_links (chat_id, file_id)
+    SELECT gn.chat_id, gn.file_id
+    FROM genuinely_new gn, current c
+    WHERE c.cnt + (SELECT COUNT(*) FROM genuinely_new) <= @max_file_links::int
+    ON CONFLICT (chat_id, file_id) DO NOTHING
+    RETURNING file_id
+)
+SELECT
+    (SELECT COUNT(*)::int FROM genuinely_new) -
+    (SELECT COUNT(*)::int FROM inserted) AS rejected_new_files;
+
 -- name: AcquireChats :many
 -- Acquires up to @num_chats pending chats for processing. Uses SKIP LOCKED
 -- to prevent multiple replicas from acquiring the same chat.
@@ -637,17 +674,20 @@ WHERE
    status = 'running'::chat_status
    AND heartbeat_at < @stale_threshold::timestamptz;

-- name: UpdateChatHeartbeat :execrows
-- Bumps the heartbeat timestamp for a running chat so that other
-- replicas know the worker is still alive.
+-- name: UpdateChatHeartbeats :many
+-- Bumps the heartbeat timestamp for the given set of chat IDs,
+-- provided they are still running and owned by the specified
+-- worker. Returns the IDs that were actually updated so the
+-- caller can detect stolen or completed chats via set-difference.
 UPDATE
    chats
 SET
-    heartbeat_at = NOW()
+    heartbeat_at = @now::timestamptz
 WHERE
-    id = @id::uuid
+    id = ANY(@ids::uuid[])
    AND worker_id = @worker_id::uuid
-    AND status = 'running'::chat_status;
+    AND status = 'running'::chat_status
+RETURNING id;

 -- name: GetChatDiffStatusByChatID :one
 SELECT
@@ -883,7 +923,8 @@ SELECT
    COALESCE(SUM(cm.input_tokens), 0)::bigint AS total_input_tokens,
    COALESCE(SUM(cm.output_tokens), 0)::bigint AS total_output_tokens,
    COALESCE(SUM(cm.cache_read_tokens), 0)::bigint AS total_cache_read_tokens,
-    COALESCE(SUM(cm.cache_creation_tokens), 0)::bigint AS total_cache_creation_tokens
+    COALESCE(SUM(cm.cache_creation_tokens), 0)::bigint AS total_cache_creation_tokens,
+    COALESCE(SUM(cm.runtime_ms), 0)::bigint AS total_runtime_ms
 FROM
    chat_messages cm
 JOIN
@@ -913,7 +954,8 @@ SELECT
    COALESCE(SUM(cm.input_tokens), 0)::bigint AS total_input_tokens,
    COALESCE(SUM(cm.output_tokens), 0)::bigint AS total_output_tokens,
    COALESCE(SUM(cm.cache_read_tokens), 0)::bigint AS total_cache_read_tokens,
-    COALESCE(SUM(cm.cache_creation_tokens), 0)::bigint AS total_cache_creation_tokens
+    COALESCE(SUM(cm.cache_creation_tokens), 0)::bigint AS total_cache_creation_tokens,
+    COALESCE(SUM(cm.runtime_ms), 0)::bigint AS total_runtime_ms
 FROM
    chat_messages cm
 JOIN
@@ -948,7 +990,8 @@ WITH chat_costs AS (
        COALESCE(SUM(cm.input_tokens), 0)::bigint AS total_input_tokens,
        COALESCE(SUM(cm.output_tokens), 0)::bigint AS total_output_tokens,
        COALESCE(SUM(cm.cache_read_tokens), 0)::bigint AS total_cache_read_tokens,
-        COALESCE(SUM(cm.cache_creation_tokens), 0)::bigint AS total_cache_creation_tokens
+        COALESCE(SUM(cm.cache_creation_tokens), 0)::bigint AS total_cache_creation_tokens,
+        COALESCE(SUM(cm.runtime_ms), 0)::bigint AS total_runtime_ms
    FROM chat_messages cm
    JOIN chats c ON c.id = cm.chat_id
    WHERE c.owner_id = @owner_id::uuid
@@ -965,7 +1008,8 @@ SELECT
    cc.total_input_tokens,
    cc.total_output_tokens,
    cc.total_cache_read_tokens,
-    cc.total_cache_creation_tokens
+    cc.total_cache_creation_tokens,
+    cc.total_runtime_ms
 FROM chat_costs cc
 LEFT JOIN chats rc ON rc.id = cc.root_chat_id
 ORDER BY cc.total_cost_micros DESC;
@@ -991,7 +1035,8 @@ WITH chat_cost_users AS (
        COALESCE(SUM(cm.input_tokens), 0)::bigint AS total_input_tokens,
        COALESCE(SUM(cm.output_tokens), 0)::bigint AS total_output_tokens,
        COALESCE(SUM(cm.cache_read_tokens), 0)::bigint AS total_cache_read_tokens,
-        COALESCE(SUM(cm.cache_creation_tokens), 0)::bigint AS total_cache_creation_tokens
+        COALESCE(SUM(cm.cache_creation_tokens), 0)::bigint AS total_cache_creation_tokens,
+        COALESCE(SUM(cm.runtime_ms), 0)::bigint AS total_runtime_ms
    FROM
        chat_messages cm
    JOIN
@@ -1025,6 +1070,7 @@ SELECT
    total_output_tokens,
    total_cache_read_tokens,
    total_cache_creation_tokens,
+    total_runtime_ms,
    COUNT(*) OVER()::bigint AS total_count
 FROM
    chat_cost_users
@@ -133,111 +133,113 @@ OFFSET
 	@offset_opt;

 -- name: CountConnectionLogs :one
-SELECT
-	COUNT(*) AS count
-FROM
-	connection_logs
-JOIN users AS workspace_owner ON
-	connection_logs.workspace_owner_id = workspace_owner.id
-LEFT JOIN users ON
-	connection_logs.user_id = users.id
-JOIN organizations ON
-	connection_logs.organization_id = organizations.id
-WHERE
-	-- Filter organization_id
-	CASE
-		WHEN @organization_id :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
-			connection_logs.organization_id = @organization_id
-		ELSE true
-	END
-	-- Filter by workspace owner username
-	AND CASE
-		WHEN @workspace_owner :: text != '' THEN
-			workspace_owner_id = (
-				SELECT id FROM users
-				WHERE lower(username) = lower(@workspace_owner) AND deleted = false
-			)
-		ELSE true
-	END
-	-- Filter by workspace_owner_id
-	AND CASE
-		WHEN @workspace_owner_id :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
-			workspace_owner_id = @workspace_owner_id
-		ELSE true
-	END
-	-- Filter by workspace_owner_email
-	AND CASE
-		WHEN @workspace_owner_email :: text != '' THEN
-			workspace_owner_id = (
-				SELECT id FROM users
-				WHERE email = @workspace_owner_email AND deleted = false
-			)
-		ELSE true
-	END
-	-- Filter by type
-	AND CASE
-		WHEN @type :: text != '' THEN
-			type = @type :: connection_type
-		ELSE true
-	END
-	-- Filter by user_id
-	AND CASE
-		WHEN @user_id :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
-			user_id = @user_id
-		ELSE true
-	END
-	-- Filter by username
-	AND CASE
-		WHEN @username :: text != '' THEN
-			user_id = (
-				SELECT id FROM users
-				WHERE lower(username) = lower(@username) AND deleted = false
-			)
-		ELSE true
-	END
-	-- Filter by user_email
-	AND CASE
-		WHEN @user_email :: text != '' THEN
-			users.email = @user_email
-		ELSE true
-	END
-	-- Filter by connected_after
-	AND CASE
-		WHEN @connected_after :: timestamp with time zone != '0001-01-01 00:00:00Z' THEN
-			connect_time >= @connected_after
-		ELSE true
-	END
-	-- Filter by connected_before
-	AND CASE
-		WHEN @connected_before :: timestamp with time zone != '0001-01-01 00:00:00Z' THEN
-			connect_time <= @connected_before
-		ELSE true
-	END
-	-- Filter by workspace_id
-	AND CASE
-		WHEN @workspace_id :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
-			connection_logs.workspace_id = @workspace_id
-		ELSE true
-	END
-	-- Filter by connection_id
-	AND CASE
-		WHEN @connection_id :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
-			connection_logs.connection_id = @connection_id
-		ELSE true
-	END
-	-- Filter by whether the session has a disconnect_time
-	AND CASE
-		WHEN @status :: text != '' THEN
-			((@status = 'ongoing' AND disconnect_time IS NULL) OR
-			(@status = 'completed' AND disconnect_time IS NOT NULL)) AND
-			-- Exclude web events, since we don't know their close time.
-			"type" NOT IN ('workspace_app', 'port_forwarding')
-		ELSE true
-	END
-	-- Authorize Filter clause will be injected below in
-	-- CountAuthorizedConnectionLogs
-	-- @authorize_filter
-;
+SELECT COUNT(*) AS count FROM (
+	SELECT 1
+	FROM
+		connection_logs
+	JOIN users AS workspace_owner ON
+		connection_logs.workspace_owner_id = workspace_owner.id
+	LEFT JOIN users ON
+		connection_logs.user_id = users.id
+	JOIN organizations ON
+		connection_logs.organization_id = organizations.id
+	WHERE
+		-- Filter organization_id
+		CASE
+			WHEN @organization_id :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
+				connection_logs.organization_id = @organization_id
+			ELSE true
+		END
+		-- Filter by workspace owner username
+		AND CASE
+			WHEN @workspace_owner :: text != '' THEN
+				workspace_owner_id = (
+					SELECT id FROM users
+					WHERE lower(username) = lower(@workspace_owner) AND deleted = false
+				)
+			ELSE true
+		END
+		-- Filter by workspace_owner_id
+		AND CASE
+			WHEN @workspace_owner_id :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
+				workspace_owner_id = @workspace_owner_id
+			ELSE true
+		END
+		-- Filter by workspace_owner_email
+		AND CASE
+			WHEN @workspace_owner_email :: text != '' THEN
+				workspace_owner_id = (
+					SELECT id FROM users
+					WHERE email = @workspace_owner_email AND deleted = false
+				)
+			ELSE true
+		END
+		-- Filter by type
+		AND CASE
+			WHEN @type :: text != '' THEN
+				type = @type :: connection_type
+			ELSE true
+		END
+		-- Filter by user_id
+		AND CASE
+			WHEN @user_id :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
+				user_id = @user_id
+			ELSE true
+		END
+		-- Filter by username
+		AND CASE
+			WHEN @username :: text != '' THEN
+				user_id = (
+					SELECT id FROM users
+					WHERE lower(username) = lower(@username) AND deleted = false
+				)
+			ELSE true
+		END
+		-- Filter by user_email
+		AND CASE
+			WHEN @user_email :: text != '' THEN
+				users.email = @user_email
+			ELSE true
+		END
+		-- Filter by connected_after
+		AND CASE
+			WHEN @connected_after :: timestamp with time zone != '0001-01-01 00:00:00Z' THEN
+				connect_time >= @connected_after
+			ELSE true
+		END
+		-- Filter by connected_before
+		AND CASE
+			WHEN @connected_before :: timestamp with time zone != '0001-01-01 00:00:00Z' THEN
+				connect_time <= @connected_before
+			ELSE true
+		END
+		-- Filter by workspace_id
+		AND CASE
+			WHEN @workspace_id :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
+				connection_logs.workspace_id = @workspace_id
+			ELSE true
+		END
+		-- Filter by connection_id
+		AND CASE
+			WHEN @connection_id :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN
+				connection_logs.connection_id = @connection_id
+			ELSE true
+		END
+		-- Filter by whether the session has a disconnect_time
+		AND CASE
+			WHEN @status :: text != '' THEN
+				((@status = 'ongoing' AND disconnect_time IS NULL) OR
+				(@status = 'completed' AND disconnect_time IS NOT NULL)) AND
+				-- Exclude web events, since we don't know their close time.
+				"type" NOT IN ('workspace_app', 'port_forwarding')
+			ELSE true
+		END
+		-- Authorize Filter clause will be injected below in
+		-- CountAuthorizedConnectionLogs
+		-- @authorize_filter
+	-- NOTE: See the CountAuditLogs LIMIT note.
+	LIMIT NULLIF(@count_cap::int, 0) + 1
+) AS limited_count;

 -- name: DeleteOldConnectionLogs :execrows
 WITH old_logs AS (
@@ -247,6 +247,7 @@ sql:
          mcp_server_tool_snapshots: MCPServerToolSnapshots
          mcp_server_config_id: MCPServerConfigID
          mcp_server_ids: MCPServerIDs
+          max_file_links: MaxFileLinks
          icon_url: IconURL
          oauth2_client_id: OAuth2ClientID
          oauth2_client_secret: OAuth2ClientSecret
@@ -16,6 +16,7 @@ const (
 	UniqueAuditLogsPkey                                       UniqueConstraint = "audit_logs_pkey"                                                 // ALTER TABLE ONLY audit_logs ADD CONSTRAINT audit_logs_pkey PRIMARY KEY (id);
 	UniqueBoundaryUsageStatsPkey                              UniqueConstraint = "boundary_usage_stats_pkey"                                       // ALTER TABLE ONLY boundary_usage_stats ADD CONSTRAINT boundary_usage_stats_pkey PRIMARY KEY (replica_id);
 	UniqueChatDiffStatusesPkey                                UniqueConstraint = "chat_diff_statuses_pkey"                                         // ALTER TABLE ONLY chat_diff_statuses ADD CONSTRAINT chat_diff_statuses_pkey PRIMARY KEY (chat_id);
+	UniqueChatFileLinksChatIDFileIDKey                        UniqueConstraint = "chat_file_links_chat_id_file_id_key"                             // ALTER TABLE ONLY chat_file_links ADD CONSTRAINT chat_file_links_chat_id_file_id_key UNIQUE (chat_id, file_id);
 	UniqueChatFilesPkey                                       UniqueConstraint = "chat_files_pkey"                                                 // ALTER TABLE ONLY chat_files ADD CONSTRAINT chat_files_pkey PRIMARY KEY (id);
 	UniqueChatMessagesPkey                                    UniqueConstraint = "chat_messages_pkey"                                              // ALTER TABLE ONLY chat_messages ADD CONSTRAINT chat_messages_pkey PRIMARY KEY (id);
 	UniqueChatModelConfigsPkey                                UniqueConstraint = "chat_model_configs_pkey"                                         // ALTER TABLE ONLY chat_model_configs ADD CONSTRAINT chat_model_configs_pkey PRIMARY KEY (id);
@@ -403,7 +403,17 @@ func (api *API) postChats(rw http.ResponseWriter, r *http.Request) {
 		return
 	}

-	contentBlocks, titleSource, inputError := createChatInputFromRequest(ctx, api.Database, req)
+	// Validate per-chat system prompt length.
+	const maxSystemPromptLen = 10000
+	if len(req.SystemPrompt) > maxSystemPromptLen {
+		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
+			Message: "System prompt exceeds maximum length.",
+			Detail:  fmt.Sprintf("System prompt must be at most %d characters, got %d.", maxSystemPromptLen, len(req.SystemPrompt)),
+		})
+		return
+	}
+
+	contentBlocks, titleSource, fileIDs, inputError := createChatInputFromRequest(ctx, api.Database, req)
 	if inputError != nil {
 		httpapi.Write(ctx, rw, http.StatusBadRequest, *inputError)
 		return
@@ -483,7 +493,7 @@ func (api *API) postChats(rw http.ResponseWriter, r *http.Request) {
 		WorkspaceID:        workspaceSelection.WorkspaceID,
 		Title:              title,
 		ModelConfigID:      modelConfigID,
-		SystemPrompt:       api.resolvedChatSystemPrompt(ctx),
+		SystemPrompt:       req.SystemPrompt,
 		InitialUserContent: contentBlocks,
 		MCPServerIDs:       mcpServerIDs,
 		Labels:             labels,
@@ -514,7 +524,32 @@ func (api *API) postChats(rw http.ResponseWriter, r *http.Request) {
 		return
 	}

-	httpapi.Write(ctx, rw, http.StatusCreated, db2sdk.Chat(chat, nil))
+	// Link any user-uploaded files referenced in the initial
+	// message to this newly created chat (best-effort; cap
+	// enforced in SQL).
+	unlinked, capExceeded := api.linkFilesToChat(ctx, chat.ID, fileIDs)
+
+	// Re-read the chat so the response reflects the authoritative
+	// database state (file links are deduped in the join table).
+	chat, err = api.Database.GetChatByID(ctx, chat.ID)
+	if err != nil {
+		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
+			Message: "Failed to read back chat after creation.",
+			Detail:  err.Error(),
+		})
+		return
+	}
+
+	chatFiles := api.fetchChatFileMetadata(ctx, chat.ID)
+	response := db2sdk.Chat(chat, nil, chatFiles)
+	if len(unlinked) > 0 {
+		if capExceeded {
+			response.Warnings = append(response.Warnings, fileLinkCapWarning(len(unlinked)))
+		} else {
+			response.Warnings = append(response.Warnings, fileLinkErrorWarning(len(unlinked)))
+		}
+	}
+	httpapi.Write(ctx, rw, http.StatusCreated, response)
 }

 // EXPERIMENTAL: this endpoint is experimental and is subject to change.
@@ -717,6 +752,7 @@ func (api *API) chatCostSummary(rw http.ResponseWriter, r *http.Request) {
 		TotalOutputTokens:        summary.TotalOutputTokens,
 		TotalCacheReadTokens:     summary.TotalCacheReadTokens,
 		TotalCacheCreationTokens: summary.TotalCacheCreationTokens,
+		TotalRuntimeMs:           summary.TotalRuntimeMs,
 		ByModel:                  modelBreakdowns,
 		ByChat:                   chatBreakdowns,
 	}
@@ -1290,7 +1326,11 @@ func (api *API) getChat(rw http.ResponseWriter, r *http.Request) {
 			slog.Error(err),
 		)
 	}
-	httpapi.Write(ctx, rw, http.StatusOK, db2sdk.Chat(chat, diffStatus))
+
+	// Hydrate file metadata for all files linked to this chat.
+	chatFiles := api.fetchChatFileMetadata(ctx, chat.ID)
+
+	httpapi.Write(ctx, rw, http.StatusOK, db2sdk.Chat(chat, diffStatus, chatFiles))
 }

 // EXPERIMENTAL: this endpoint is experimental and is subject to change.
@@ -1780,7 +1820,7 @@ func (api *API) postChatMessages(rw http.ResponseWriter, r *http.Request) {
 		return
 	}

-	contentBlocks, _, inputError := createChatInputFromParts(ctx, api.Database, req.Content, "content")
+	contentBlocks, _, fileIDs, inputError := createChatInputFromParts(ctx, api.Database, req.Content, "content")
 	if inputError != nil {
 		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
 			Message: inputError.Message,
@@ -1819,6 +1859,20 @@ func (api *API) postChatMessages(rw http.ResponseWriter, r *http.Request) {
 		}
 	}

+	busyBehavior := chatd.SendMessageBusyBehaviorQueue
+	switch req.BusyBehavior {
+	case codersdk.ChatBusyBehaviorInterrupt:
+		busyBehavior = chatd.SendMessageBusyBehaviorInterrupt
+	case codersdk.ChatBusyBehaviorQueue, "":
+		// Default to queue.
+	default:
+		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
+			Message: "Invalid busy_behavior value.",
+			Detail:  `Must be "queue" or "interrupt".`,
+		})
+		return
+	}
+
 	sendResult, sendErr := api.chatDaemon.SendMessage(
 		ctx,
 		chatd.SendMessageOptions{
@@ -1826,7 +1880,7 @@ func (api *API) postChatMessages(rw http.ResponseWriter, r *http.Request) {
 			CreatedBy:     apiKey.UserID,
 			Content:       contentBlocks,
 			ModelConfigID: req.ModelConfigID,
-			BusyBehavior:  chatd.SendMessageBusyBehaviorQueue,
+			BusyBehavior:  busyBehavior,
 			MCPServerIDs:  req.MCPServerIDs,
 		},
 	)
@@ -1848,6 +1902,9 @@ func (api *API) postChatMessages(rw http.ResponseWriter, r *http.Request) {
 		return
 	}

+	// Link any user-uploaded files referenced in this message
+	// to the chat (best-effort; cap enforced in SQL).
+	unlinked, capExceeded := api.linkFilesToChat(ctx, chatID, fileIDs)
 	response := codersdk.CreateChatMessageResponse{Queued: sendResult.Queued}
 	if sendResult.Queued {
 		if sendResult.QueuedMessage != nil {
@@ -1857,6 +1914,13 @@ func (api *API) postChatMessages(rw http.ResponseWriter, r *http.Request) {
 		message := convertChatMessage(sendResult.Message)
 		response.Message = &message
 	}
+	if len(unlinked) > 0 {
+		if capExceeded {
+			response.Warnings = append(response.Warnings, fileLinkCapWarning(len(unlinked)))
+		} else {
+			response.Warnings = append(response.Warnings, fileLinkErrorWarning(len(unlinked)))
+		}
+	}

 	httpapi.Write(ctx, rw, http.StatusOK, response)
 }
@@ -1890,7 +1954,7 @@ func (api *API) patchChatMessage(rw http.ResponseWriter, r *http.Request) {
 		return
 	}

-	contentBlocks, _, inputError := createChatInputFromParts(ctx, api.Database, req.Content, "content")
+	contentBlocks, _, fileIDs, inputError := createChatInputFromParts(ctx, api.Database, req.Content, "content")
 	if inputError != nil {
 		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
 			Message: inputError.Message,
@@ -1929,8 +1993,20 @@ func (api *API) patchChatMessage(rw http.ResponseWriter, r *http.Request) {
 		return
 	}

-	message := convertChatMessage(editResult.Message)
-	httpapi.Write(ctx, rw, http.StatusOK, message)
+	// Link any user-uploaded files referenced in the edited
+	// message to the chat (best-effort; cap enforced in SQL).
+	unlinked, capExceeded := api.linkFilesToChat(ctx, chat.ID, fileIDs)
+	response := codersdk.EditChatMessageResponse{
+		Message: convertChatMessage(editResult.Message),
+	}
+	if len(unlinked) > 0 {
+		if capExceeded {
+			response.Warnings = append(response.Warnings, fileLinkCapWarning(len(unlinked)))
+		} else {
+			response.Warnings = append(response.Warnings, fileLinkErrorWarning(len(unlinked)))
+		}
+	}
+	httpapi.Write(ctx, rw, http.StatusOK, response)
 }

 // EXPERIMENTAL: this endpoint is experimental and is subject to change.
@@ -2207,7 +2283,7 @@ func (api *API) interruptChat(rw http.ResponseWriter, r *http.Request) {
 		chat = updatedChat
 	}

-	httpapi.Write(ctx, rw, http.StatusOK, db2sdk.Chat(chat, nil))
+	httpapi.Write(ctx, rw, http.StatusOK, db2sdk.Chat(chat, nil, nil))
 }

 // EXPERIMENTAL: this endpoint is experimental and is subject to change.
@@ -2251,7 +2327,7 @@ func (api *API) regenerateChatTitle(rw http.ResponseWriter, r *http.Request) {
 		return
 	}

-	httpapi.Write(ctx, rw, http.StatusOK, db2sdk.Chat(updatedChat, nil))
+	httpapi.Write(ctx, rw, http.StatusOK, db2sdk.Chat(updatedChat, nil, nil))
 }

 // EXPERIMENTAL: this endpoint is experimental and is subject to change.
@@ -3476,35 +3552,6 @@ func (api *API) deleteUserChatCompactionThreshold(rw http.ResponseWriter, r *htt
 	rw.WriteHeader(http.StatusNoContent)
 }

-func (api *API) resolvedChatSystemPrompt(ctx context.Context) string {
-	config, err := api.Database.GetChatSystemPromptConfig(ctx)
-	if err != nil {
-		// We intentionally fail open here. When the prompt configuration
-		// cannot be read, returning the built-in default keeps the chat
-		// grounded instead of sending no system guidance at all.
-		api.Logger.Error(ctx, "failed to fetch chat system prompt configuration, using default", slog.Error(err))
-		return chatd.DefaultSystemPrompt
-	}
-
-	sanitizedCustom := chatd.SanitizePromptText(config.ChatSystemPrompt)
-	if sanitizedCustom == "" && strings.TrimSpace(config.ChatSystemPrompt) != "" {
-		api.Logger.Warn(ctx, "custom system prompt became empty after sanitization, omitting custom portion")
-	}
-
-	var parts []string
-	if config.IncludeDefaultSystemPrompt {
-		parts = append(parts, chatd.DefaultSystemPrompt)
-	}
-	if sanitizedCustom != "" {
-		parts = append(parts, sanitizedCustom)
-	}
-	result := strings.Join(parts, "\n\n")
-	if result == "" {
-		api.Logger.Warn(ctx, "resolved system prompt is empty, no system prompt will be injected into chats")
-	}
-	return result
-}
-
 func (api *API) postChatFile(rw http.ResponseWriter, r *http.Request) {
 	ctx := r.Context()
 	apiKey := httpmw.APIKey(r)
@@ -3692,6 +3739,7 @@ func (api *API) chatFileByID(rw http.ResponseWriter, r *http.Request) {
 func createChatInputFromRequest(ctx context.Context, db database.Store, req codersdk.CreateChatRequest) (
 	[]codersdk.ChatMessagePart,
 	string,
+	[]uuid.UUID,
 	*codersdk.Response,
 ) {
 	return createChatInputFromParts(ctx, db, req.Content, "content")
@@ -3702,14 +3750,15 @@ func createChatInputFromParts(
 	db database.Store,
 	parts []codersdk.ChatInputPart,
 	fieldName string,
-) ([]codersdk.ChatMessagePart, string, *codersdk.Response) {
+) ([]codersdk.ChatMessagePart, string, []uuid.UUID, *codersdk.Response) {
 	if len(parts) == 0 {
-		return nil, "", &codersdk.Response{
+		return nil, "", nil, &codersdk.Response{
 			Message: "Content is required.",
 			Detail:  "Content cannot be empty.",
 		}
 	}

+	var fileIDs []uuid.UUID
 	content := make([]codersdk.ChatMessagePart, 0, len(parts))
 	textParts := make([]string, 0, len(parts))
 	for i, part := range parts {
@@ -3717,7 +3766,7 @@ func createChatInputFromParts(
 		case string(codersdk.ChatInputPartTypeText):
 			text := strings.TrimSpace(part.Text)
 			if text == "" {
-				return nil, "", &codersdk.Response{
+				return nil, "", nil, &codersdk.Response{
 					Message: "Invalid input part.",
 					Detail:  fmt.Sprintf("%s[%d].text cannot be empty.", fieldName, i),
 				}
@@ -3726,7 +3775,7 @@ func createChatInputFromParts(
 			textParts = append(textParts, text)
 		case string(codersdk.ChatInputPartTypeFile):
 			if part.FileID == uuid.Nil {
-				return nil, "", &codersdk.Response{
+				return nil, "", nil, &codersdk.Response{
 					Message: "Invalid input part.",
 					Detail:  fmt.Sprintf("%s[%d].file_id is required for file parts.", fieldName, i),
 				}
@@ -3737,20 +3786,23 @@ func createChatInputFromParts(
 			chatFile, err := db.GetChatFileByID(ctx, part.FileID)
 			if err != nil {
 				if httpapi.Is404Error(err) {
-					return nil, "", &codersdk.Response{
+					return nil, "", nil, &codersdk.Response{
 						Message: "Invalid input part.",
 						Detail:  fmt.Sprintf("%s[%d].file_id references a file that does not exist.", fieldName, i),
 					}
 				}
-				return nil, "", &codersdk.Response{
+				return nil, "", nil, &codersdk.Response{
 					Message: "Internal error.",
 					Detail:  fmt.Sprintf("Failed to retrieve file for %s[%d].", fieldName, i),
 				}
 			}
 			content = append(content, codersdk.ChatMessageFile(part.FileID, chatFile.Mimetype))
+			fileIDs = append(fileIDs, part.FileID)
+		// file-reference parts carry inline code snippets, not uploaded
+		// files. They have no FileID and are excluded from file tracking.
 		case string(codersdk.ChatInputPartTypeFileReference):
 			if part.FileName == "" {
-				return nil, "", &codersdk.Response{
+				return nil, "", nil, &codersdk.Response{
 					Message: "Invalid input part.",
 					Detail:  fmt.Sprintf("%s[%d].file_name cannot be empty for file-reference.", fieldName, i),
 				}
@@ -3767,21 +3819,8 @@ func createChatInputFromParts(
 				_, _ = fmt.Fprintf(&sb, "\n```%s\n%s\n```", part.FileName, strings.TrimSpace(part.Content))
 			}
 			textParts = append(textParts, sb.String())
-		case string(codersdk.ChatInputPartTypeSkill):
-			if part.SkillName == "" {
-				return nil, "", &codersdk.Response{
-					Message: "Invalid input part.",
-					Detail:  fmt.Sprintf("%s[%d].skill_name cannot be empty for skill parts.", fieldName, i),
-				}
-			}
-			content = append(content, codersdk.ChatMessagePart{
-				Type:             codersdk.ChatMessagePartTypeSkill,
-				SkillName:        part.SkillName,
-				SkillDescription: part.SkillDescription,
-			})
-			textParts = append(textParts, fmt.Sprintf("Use the %q skill", part.SkillName))
 		default:
-			return nil, "", &codersdk.Response{
+			return nil, "", nil, &codersdk.Response{
 				Message: "Invalid input part.",
 				Detail: fmt.Sprintf(
 					"%s[%d].type %q is not supported.",
@@ -3796,13 +3835,13 @@ func createChatInputFromParts(
 	// Allow file-only messages. The titleSource may be empty
 	// when only file parts are provided, callers handle this.
 	if len(content) == 0 {
-		return nil, "", &codersdk.Response{
+		return nil, "", nil, &codersdk.Response{
 			Message: "Content is required.",
 			Detail:  fmt.Sprintf("%s must include at least one text or file part.", fieldName),
 		}
 	}
 	titleSource := strings.TrimSpace(strings.Join(textParts, " "))
-	return content, titleSource, nil
+	return content, titleSource, fileIDs, nil
 }

 func chatTitleFromMessage(message string) string {
@@ -3837,6 +3876,70 @@ func truncateRunes(value string, maxLen int) string {
 	return string(runes[:maxLen])
 }

+// linkFilesToChat inserts file-link rows into the chat_file_links
+// join table. Cap enforcement and dedup are handled atomically in
+// SQL. On success returns (nil, false). On failure returns the full
+// input fileIDs slice — linking is all-or-nothing because the
+// SQL operates on the batch atomically. capExceeded indicates
+// whether the failure was due to the cap being exceeded (true)
+// or a database error (false).
+// Failures are logged but never block the caller.
+func (api *API) linkFilesToChat(ctx context.Context, chatID uuid.UUID, fileIDs []uuid.UUID) (unlinked []uuid.UUID, capExceeded bool) {
+	if len(fileIDs) == 0 {
+		return nil, false
+	}
+	rejected, err := api.Database.LinkChatFiles(ctx, database.LinkChatFilesParams{
+		ChatID:       chatID,
+		MaxFileLinks: int32(codersdk.MaxChatFileIDs),
+		FileIds:      fileIDs,
+	})
+	if err != nil {
+		api.Logger.Error(ctx, "failed to link files to chat",
+			slog.F("chat_id", chatID),
+			slog.F("file_ids", fileIDs),
+			slog.Error(err),
+		)
+		return fileIDs, false
+	}
+	if rejected > 0 {
+		api.Logger.Warn(ctx, "file cap reached, files not linked",
+			slog.F("chat_id", chatID),
+			slog.F("file_ids", fileIDs),
+			slog.F("max_file_links", codersdk.MaxChatFileIDs),
+		)
+		return fileIDs, true
+	}
+	return nil, false
+}
+
+// fileLinkCapWarning builds a user-facing warning when a batch
+// of file IDs was atomically rejected because the resulting
+// array would exceed the per-chat file cap.
+func fileLinkCapWarning(count int) string {
+	return fmt.Sprintf("file linking skipped: batch of %d file(s) would exceed limit of %d", count, codersdk.MaxChatFileIDs)
+}
+
+// fileLinkErrorWarning builds a user-facing warning when a
+// database error prevented linking files to a chat.
+func fileLinkErrorWarning(count int) string {
+	return fmt.Sprintf("%d file(s) could not be linked due to a server error", count)
+}
+
+// fetchChatFileMetadata returns metadata for all files linked to
+// the given chat. Errors are logged and result in a nil return
+// (callers treat file metadata as best-effort).
+func (api *API) fetchChatFileMetadata(ctx context.Context, chatID uuid.UUID) []database.GetChatFileMetadataByChatIDRow {
+	rows, err := api.Database.GetChatFileMetadataByChatID(ctx, chatID)
+	if err != nil {
+		api.Logger.Error(ctx, "failed to fetch chat file metadata",
+			slog.F("chat_id", chatID),
+			slog.Error(err),
+		)
+		return nil
+	}
+	return rows
+}
+
 func convertChatCostModelBreakdown(model database.GetChatCostPerModelRow) codersdk.ChatCostModelBreakdown {
 	displayName := strings.TrimSpace(model.DisplayName)
 	if displayName == "" {
@@ -3853,6 +3956,7 @@ func convertChatCostModelBreakdown(model database.GetChatCostPerModelRow) coders
 		TotalOutputTokens:        model.TotalOutputTokens,
 		TotalCacheReadTokens:     model.TotalCacheReadTokens,
 		TotalCacheCreationTokens: model.TotalCacheCreationTokens,
+		TotalRuntimeMs:           model.TotalRuntimeMs,
 	}
 }

@@ -3866,6 +3970,7 @@ func convertChatCostChatBreakdown(chat database.GetChatCostPerChatRow) codersdk.
 		TotalOutputTokens:        chat.TotalOutputTokens,
 		TotalCacheReadTokens:     chat.TotalCacheReadTokens,
 		TotalCacheCreationTokens: chat.TotalCacheCreationTokens,
+		TotalRuntimeMs:           chat.TotalRuntimeMs,
 	}
 }

@@ -3882,6 +3987,7 @@ func convertChatCostUserRollup(user database.GetChatCostPerUserRow) codersdk.Cha
 		TotalOutputTokens:        user.TotalOutputTokens,
 		TotalCacheReadTokens:     user.TotalCacheReadTokens,
 		TotalCacheCreationTokens: user.TotalCacheCreationTokens,
+		TotalRuntimeMs:           user.TotalRuntimeMs,
 	}
 }

@@ -313,6 +313,111 @@ func TestPostChats(t *testing.T) {
 		}
 	})

+	t.Run("WithPerChatSystemPrompt", func(t *testing.T) {
+		t.Parallel()
+
+		ctx := testutil.Context(t, testutil.WaitLong)
+		client, db := newChatClientWithDatabase(t)
+		_ = coderdtest.CreateFirstUser(t, client.Client)
+		_ = createChatModelConfig(t, client)
+
+		chat, err := client.CreateChat(ctx, codersdk.CreateChatRequest{
+			Content: []codersdk.ChatInputPart{
+				{
+					Type: codersdk.ChatInputPartTypeText,
+					Text: "hello with system prompt",
+				},
+			},
+			SystemPrompt: "You are a Go expert.",
+		})
+		require.NoError(t, err)
+		require.NotEqual(t, uuid.Nil, chat.ID)
+
+		// Use the DB directly to see system messages, which are
+		// hidden from the public API.
+		dbMessages, err := db.GetChatMessagesForPromptByChatID(dbauthz.AsSystemRestricted(ctx), chat.ID)
+		require.NoError(t, err)
+
+		// Expect: deployment system prompt, per-chat system prompt,
+		// workspace awareness, user message.
+		var systemMessages []database.ChatMessage
+		for _, msg := range dbMessages {
+			if msg.Role == database.ChatMessageRoleSystem {
+				systemMessages = append(systemMessages, msg)
+			}
+		}
+		require.GreaterOrEqual(t, len(systemMessages), 2,
+			"expected at least deployment + per-chat system messages")
+
+		// The per-chat system prompt should be the second system
+		// message and contain the user-specified text.
+		foundPerChat := false
+		for _, msg := range systemMessages {
+			if msg.Content.Valid {
+				raw := string(msg.Content.RawMessage)
+				if strings.Contains(raw, "You are a Go expert.") {
+					foundPerChat = true
+					break
+				}
+			}
+		}
+		require.True(t, foundPerChat,
+			"per-chat system prompt not found in system messages")
+	})
+
+	t.Run("PerChatSystemPromptEmpty", func(t *testing.T) {
+		t.Parallel()
+
+		ctx := testutil.Context(t, testutil.WaitLong)
+		client, db := newChatClientWithDatabase(t)
+		_ = coderdtest.CreateFirstUser(t, client.Client)
+		_ = createChatModelConfig(t, client)
+
+		chat, err := client.CreateChat(ctx, codersdk.CreateChatRequest{
+			Content: []codersdk.ChatInputPart{
+				{
+					Type: codersdk.ChatInputPartTypeText,
+					Text: "hello without system prompt",
+				},
+			},
+			SystemPrompt: "",
+		})
+		require.NoError(t, err)
+
+		dbMessages, err := db.GetChatMessagesForPromptByChatID(dbauthz.AsSystemRestricted(ctx), chat.ID)
+		require.NoError(t, err)
+
+		// No per-chat system prompt should be present.
+		for _, msg := range dbMessages {
+			if msg.Role == database.ChatMessageRoleSystem && msg.Content.Valid {
+				raw := string(msg.Content.RawMessage)
+				require.NotContains(t, raw, "You are a Go expert.",
+					"unexpected per-chat system prompt in messages")
+			}
+		}
+	})
+
+	t.Run("PerChatSystemPromptTooLong", func(t *testing.T) {
+		t.Parallel()
+
+		ctx := testutil.Context(t, testutil.WaitLong)
+		client := newChatClient(t)
+		_ = coderdtest.CreateFirstUser(t, client.Client)
+		_ = createChatModelConfig(t, client)
+
+		longPrompt := strings.Repeat("a", 10001)
+		_, err := client.CreateChat(ctx, codersdk.CreateChatRequest{
+			Content: []codersdk.ChatInputPart{
+				{
+					Type: codersdk.ChatInputPartTypeText,
+					Text: "hello",
+				},
+			},
+			SystemPrompt: longPrompt,
+		})
+		requireSDKError(t, err, http.StatusBadRequest)
+	})
+
 	t.Run("WorkspaceNotAccessible", func(t *testing.T) {
 		t.Parallel()

@@ -3122,6 +3227,153 @@ func TestGetChat(t *testing.T) {
 		_, err = otherClient.GetChat(ctx, createdChat.ID)
 		requireSDKError(t, err, http.StatusNotFound)
 	})
+
+	t.Run("FilesHydrated", func(t *testing.T) {
+		t.Parallel()
+
+		ctx := testutil.Context(t, testutil.WaitLong)
+		client := newChatClient(t)
+		firstUser := coderdtest.CreateFirstUser(t, client.Client)
+		_ = createChatModelConfig(t, client)
+
+		// Upload a file.
+		pngData := append([]byte{0x89, 0x50, 0x4E, 0x47, 0x0D, 0x0A, 0x1A, 0x0A}, make([]byte, 64)...)
+		uploadResp, err := client.UploadChatFile(ctx, firstUser.OrganizationID, "image/png", "hydrated.png", bytes.NewReader(pngData))
+		require.NoError(t, err)
+
+		// Create a chat with a text + file part.
+		chat, err := client.CreateChat(ctx, codersdk.CreateChatRequest{
+			Content: []codersdk.ChatInputPart{
+				{Type: codersdk.ChatInputPartTypeText, Text: "check file hydration"},
+				{Type: codersdk.ChatInputPartTypeFile, FileID: uploadResp.ID},
+			},
+		})
+		require.NoError(t, err)
+
+		// GET the chat — files must be hydrated with all metadata fields.
+		chatResult, err := client.GetChat(ctx, chat.ID)
+		require.NoError(t, err)
+		require.Len(t, chatResult.Files, 1)
+		f := chatResult.Files[0]
+		require.Equal(t, uploadResp.ID, f.ID)
+		require.Equal(t, firstUser.UserID, f.OwnerID)
+		require.NotEqual(t, uuid.Nil, f.OrganizationID)
+		require.Equal(t, "image/png", f.MimeType)
+		require.Equal(t, "hydrated.png", f.Name)
+		require.NotZero(t, f.CreatedAt)
+	})
+
+	// ToolCreatedFilesLinked exercises the DB path that chatd uses
+	// when a tool (e.g. propose_plan) creates a file: InsertChatFile
+	// then LinkChatFiles. This is a DB-level test because driving
+	// the full chatd tool-call pipeline requires an LLM mock.
+	t.Run("ToolCreatedFilesLinked", func(t *testing.T) {
+		t.Parallel()
+
+		ctx := testutil.Context(t, testutil.WaitLong)
+		client, store := newChatClientWithDatabase(t)
+		firstUser := coderdtest.CreateFirstUser(t, client.Client)
+		_ = createChatModelConfig(t, client)
+
+		// Create a chat via the API so all metadata is set up.
+		chat, err := client.CreateChat(ctx, codersdk.CreateChatRequest{
+			Content: []codersdk.ChatInputPart{
+				{Type: codersdk.ChatInputPartTypeText, Text: "tool file test"},
+			},
+		})
+		require.NoError(t, err)
+
+		// Mimic what chatd's StoreFile closure does:
+		// 1. InsertChatFile
+		// 2. LinkChatFiles
+		//nolint:gocritic // Using AsChatd to mimic the chatd background worker.
+		chatdCtx := dbauthz.AsChatd(ctx)
+		fileRow, err := store.InsertChatFile(chatdCtx, database.InsertChatFileParams{
+			OwnerID:        firstUser.UserID,
+			OrganizationID: firstUser.OrganizationID,
+			Name:           "plan.md",
+			Mimetype:       "text/markdown",
+			Data:           []byte("# Plan"),
+		})
+		require.NoError(t, err)
+
+		rejected, err := store.LinkChatFiles(chatdCtx, database.LinkChatFilesParams{
+			ChatID:       chat.ID,
+			MaxFileLinks: int32(codersdk.MaxChatFileIDs),
+			FileIds:      []uuid.UUID{fileRow.ID},
+		})
+		require.NoError(t, err)
+		require.Equal(t, int32(0), rejected, "0 rejected = all files linked")
+
+		// Verify via the API that the file appears in the chat.
+		chatResult, err := client.GetChat(ctx, chat.ID)
+		require.NoError(t, err)
+		require.Len(t, chatResult.Files, 1)
+		f := chatResult.Files[0]
+		require.Equal(t, fileRow.ID, f.ID)
+		require.Equal(t, firstUser.UserID, f.OwnerID)
+		require.Equal(t, firstUser.OrganizationID, f.OrganizationID)
+		require.Equal(t, "plan.md", f.Name)
+		require.Equal(t, "text/markdown", f.MimeType)
+
+		// Fill up to the cap by inserting more files via the
+		// chatd DB path, then verify the cap is enforced.
+		for i := 1; i < codersdk.MaxChatFileIDs; i++ {
+			extra, err := store.InsertChatFile(chatdCtx, database.InsertChatFileParams{
+				OwnerID:        firstUser.UserID,
+				OrganizationID: firstUser.OrganizationID,
+				Name:           fmt.Sprintf("file%d.md", i),
+				Mimetype:       "text/markdown",
+				Data:           []byte("data"),
+			})
+			require.NoError(t, err)
+			_, err = store.LinkChatFiles(chatdCtx, database.LinkChatFilesParams{
+				ChatID:       chat.ID,
+				MaxFileLinks: int32(codersdk.MaxChatFileIDs),
+				FileIds:      []uuid.UUID{extra.ID},
+			})
+			require.NoError(t, err)
+		}
+
+		// Chat should now have exactly MaxChatFileIDs files.
+		chatResult, err = client.GetChat(ctx, chat.ID)
+		require.NoError(t, err)
+		require.Len(t, chatResult.Files, codersdk.MaxChatFileIDs)
+
+		// Attempt to add one more file — should be rejected (0 rows).
+		overflow, err := store.InsertChatFile(chatdCtx, database.InsertChatFileParams{
+			OwnerID:        firstUser.UserID,
+			OrganizationID: firstUser.OrganizationID,
+			Name:           "overflow.md",
+			Mimetype:       "text/markdown",
+			Data:           []byte("too many"),
+		})
+		require.NoError(t, err)
+		rejected, err = store.LinkChatFiles(chatdCtx, database.LinkChatFilesParams{
+			ChatID:       chat.ID,
+			MaxFileLinks: int32(codersdk.MaxChatFileIDs),
+			FileIds:      []uuid.UUID{overflow.ID},
+		})
+		require.NoError(t, err)
+		require.Equal(t, int32(1), rejected, "cap should reject the 21st file")
+
+		// Re-appending an already-linked ID at cap should succeed
+		// (dedup means no array growth).
+		rejected, err = store.LinkChatFiles(chatdCtx, database.LinkChatFilesParams{
+			ChatID:       chat.ID,
+			MaxFileLinks: int32(codersdk.MaxChatFileIDs),
+			FileIds:      []uuid.UUID{fileRow.ID},
+		})
+		require.NoError(t, err)
+		// ON CONFLICT DO NOTHING returns 0 rows when the link
+		// already exists, which is fine — the file is still linked.
+		require.Equal(t, int32(0), rejected, "dedup of existing ID should be a no-op")
+
+		// Count should still be exactly MaxChatFileIDs.
+		chatResult, err = client.GetChat(ctx, chat.ID)
+		require.NoError(t, err)
+		require.Len(t, chatResult.Files, codersdk.MaxChatFileIDs)
+	})
 }

 func TestArchiveChat(t *testing.T) {
@@ -4135,104 +4387,6 @@ func TestChatMessageWithFileReferences(t *testing.T) {
 	})
 }

-func TestChatMessageWithSkillParts(t *testing.T) {
-	t.Parallel()
-
-	createChatForTest := func(t *testing.T, client *codersdk.ExperimentalClient) codersdk.Chat {
-		t.Helper()
-		ctx := testutil.Context(t, testutil.WaitLong)
-		chat, err := client.CreateChat(ctx, codersdk.CreateChatRequest{
-			Content: []codersdk.ChatInputPart{{
-				Type: codersdk.ChatInputPartTypeText,
-				Text: "initial message",
-			}},
-		})
-		require.NoError(t, err)
-		return chat
-	}
-
-	t.Run("SkillPartRoundTrip", func(t *testing.T) {
-		t.Parallel()
-
-		ctx := testutil.Context(t, testutil.WaitLong)
-		client := newChatClient(t)
-		_ = coderdtest.CreateFirstUser(t, client.Client)
-		_ = createChatModelConfig(t, client)
-		chat := createChatForTest(t, client)
-
-		created, err := client.CreateChatMessage(ctx, chat.ID, codersdk.CreateChatMessageRequest{
-			Content: []codersdk.ChatInputPart{
-				{
-					Type: codersdk.ChatInputPartTypeText,
-					Text: "please run this skill",
-				},
-				{
-					Type:             codersdk.ChatInputPartTypeSkill,
-					SkillName:        "deep-review",
-					SkillDescription: "Multi-reviewer code review",
-				},
-			},
-		})
-		require.NoError(t, err)
-
-		checkSkill := func(part codersdk.ChatMessagePart) bool {
-			return part.Type == codersdk.ChatMessagePartTypeSkill &&
-				part.SkillName == "deep-review" &&
-				part.SkillDescription == "Multi-reviewer code review"
-		}
-
-		var found bool
-		require.Eventually(t, func() bool {
-			messagesResult, getErr := client.GetChatMessages(ctx, chat.ID, nil)
-			if getErr != nil {
-				return false
-			}
-			for _, message := range messagesResult.Messages {
-				if message.Role != codersdk.ChatMessageRoleUser {
-					continue
-				}
-				for _, part := range message.Content {
-					if checkSkill(part) {
-						found = true
-						return true
-					}
-				}
-			}
-			if created.Queued && created.QueuedMessage != nil {
-				for _, queued := range messagesResult.QueuedMessages {
-					for _, part := range queued.Content {
-						if checkSkill(part) {
-							found = true
-							return true
-						}
-					}
-				}
-			}
-			return false
-		}, testutil.WaitLong, testutil.IntervalFast)
-		require.True(t, found, "expected to find skill part in stored message")
-	})
-
-	t.Run("SkillPartEmptyNameRejected", func(t *testing.T) {
-		t.Parallel()
-
-		ctx := testutil.Context(t, testutil.WaitLong)
-		client := newChatClient(t)
-		_ = coderdtest.CreateFirstUser(t, client.Client)
-		_ = createChatModelConfig(t, client)
-		chat := createChatForTest(t, client)
-
-		_, err := client.CreateChatMessage(ctx, chat.ID, codersdk.CreateChatMessageRequest{
-			Content: []codersdk.ChatInputPart{{
-				Type:      codersdk.ChatInputPartTypeSkill,
-				SkillName: "",
-			}},
-		})
-		require.Error(t, err)
-		require.Contains(t, err.Error(), "skill_name cannot be empty")
-	})
-}
-
 func TestChatMessageWithFiles(t *testing.T) {
 	t.Parallel()

@@ -4366,6 +4520,14 @@ func TestChatMessageWithFiles(t *testing.T) {

 		// With no text, chatTitleFromMessage("") returns "New Chat".
 		require.Equal(t, "New Chat", chat.Title)
+		require.Len(t, chat.Files, 1)
+		f := chat.Files[0]
+		require.Equal(t, uploadResp.ID, f.ID)
+		require.Equal(t, firstUser.UserID, f.OwnerID)
+		require.NotEqual(t, uuid.Nil, f.OrganizationID)
+		require.Equal(t, "image/png", f.MimeType)
+		require.Equal(t, "test.png", f.Name)
+		require.NotZero(t, f.CreatedAt)
 	})

 	t.Run("InvalidFileID", func(t *testing.T) {
@@ -4400,6 +4562,189 @@ func TestChatMessageWithFiles(t *testing.T) {
 		require.Equal(t, "Invalid input part.", sdkErr.Message)
 		require.Contains(t, sdkErr.Detail, "does not exist")
 	})
+
+	t.Run("FilesLinkedOnSend", func(t *testing.T) {
+		t.Parallel()
+
+		ctx := testutil.Context(t, testutil.WaitLong)
+		client := newChatClient(t)
+		firstUser := coderdtest.CreateFirstUser(t, client.Client)
+		_ = createChatModelConfig(t, client)
+
+		// Create a text-only chat (no files initially).
+		chat, err := client.CreateChat(ctx, codersdk.CreateChatRequest{
+			Content: []codersdk.ChatInputPart{
+				{Type: codersdk.ChatInputPartTypeText, Text: "no files yet"},
+			},
+		})
+		require.NoError(t, err)
+
+		// Upload a file.
+		pngData := append([]byte{0x89, 0x50, 0x4E, 0x47, 0x0D, 0x0A, 0x1A, 0x0A}, make([]byte, 64)...)
+		uploadResp, err := client.UploadChatFile(ctx, firstUser.OrganizationID, "image/png", "linked.png", bytes.NewReader(pngData))
+		require.NoError(t, err)
+
+		// Send a message with the file.
+		_, err = client.CreateChatMessage(ctx, chat.ID, codersdk.CreateChatMessageRequest{
+			Content: []codersdk.ChatInputPart{
+				{Type: codersdk.ChatInputPartTypeText, Text: "here is a file"},
+				{Type: codersdk.ChatInputPartTypeFile, FileID: uploadResp.ID},
+			},
+		})
+		require.NoError(t, err)
+
+		// GET the chat — file should be linked.
+		chatResult, err := client.GetChat(ctx, chat.ID)
+		require.NoError(t, err)
+		require.Len(t, chatResult.Files, 1)
+		require.Equal(t, uploadResp.ID, chatResult.Files[0].ID)
+		require.Equal(t, "linked.png", chatResult.Files[0].Name)
+	})
+
+	t.Run("DedupFileIDs", func(t *testing.T) {
+		t.Parallel()
+
+		ctx := testutil.Context(t, testutil.WaitLong)
+		client := newChatClient(t)
+		firstUser := coderdtest.CreateFirstUser(t, client.Client)
+		_ = createChatModelConfig(t, client)
+
+		// Upload a file.
+		pngData := append([]byte{0x89, 0x50, 0x4E, 0x47, 0x0D, 0x0A, 0x1A, 0x0A}, make([]byte, 64)...)
+		uploadResp, err := client.UploadChatFile(ctx, firstUser.OrganizationID, "image/png", "dedup.png", bytes.NewReader(pngData))
+		require.NoError(t, err)
+
+		// Create a chat with a file.
+		chat, err := client.CreateChat(ctx, codersdk.CreateChatRequest{
+			Content: []codersdk.ChatInputPart{
+				{Type: codersdk.ChatInputPartTypeText, Text: "first mention"},
+				{Type: codersdk.ChatInputPartTypeFile, FileID: uploadResp.ID},
+			},
+		})
+		require.NoError(t, err)
+
+		// Send another message with the SAME file.
+		msgResp, err := client.CreateChatMessage(ctx, chat.ID, codersdk.CreateChatMessageRequest{
+			Content: []codersdk.ChatInputPart{
+				{Type: codersdk.ChatInputPartTypeText, Text: "same file again"},
+				{Type: codersdk.ChatInputPartTypeFile, FileID: uploadResp.ID},
+			},
+		})
+		require.NoError(t, err)
+		require.Empty(t, msgResp.Warnings, "dedup below cap should not produce warnings")
+
+		// GET — should have exactly 1 file (deduped by SQL DISTINCT).
+		chatResult, err := client.GetChat(ctx, chat.ID)
+		require.NoError(t, err)
+		require.Len(t, chatResult.Files, 1, "duplicate file IDs should be deduped")
+		require.Equal(t, uploadResp.ID, chatResult.Files[0].ID)
+	})
+
+	t.Run("FileCapExceeded", func(t *testing.T) {
+		t.Parallel()
+
+		ctx := testutil.Context(t, testutil.WaitLong)
+		client := newChatClient(t)
+		firstUser := coderdtest.CreateFirstUser(t, client.Client)
+		_ = createChatModelConfig(t, client)
+
+		pngData := append([]byte{0x89, 0x50, 0x4E, 0x47, 0x0D, 0x0A, 0x1A, 0x0A}, make([]byte, 64)...)
+
+		// Upload MaxChatFileIDs files.
+		fileIDs := make([]uuid.UUID, 0, codersdk.MaxChatFileIDs)
+		for i := range codersdk.MaxChatFileIDs {
+			resp, err := client.UploadChatFile(ctx, firstUser.OrganizationID, "image/png", fmt.Sprintf("file%d.png", i), bytes.NewReader(pngData))
+			require.NoError(t, err)
+			fileIDs = append(fileIDs, resp.ID)
+		}
+
+		// Create a chat using all MaxChatFileIDs files.
+		parts := []codersdk.ChatInputPart{
+			{Type: codersdk.ChatInputPartTypeText, Text: "max files"},
+		}
+		for _, fid := range fileIDs {
+			parts = append(parts, codersdk.ChatInputPart{Type: codersdk.ChatInputPartTypeFile, FileID: fid})
+		}
+		chat, err := client.CreateChat(ctx, codersdk.CreateChatRequest{Content: parts})
+		require.NoError(t, err)
+		require.Empty(t, chat.Warnings, "creating a chat at exactly the cap should not warn")
+		require.Len(t, chat.Files, codersdk.MaxChatFileIDs, "all files should be linked on creation")
+
+		// Upload one more file.
+		extraResp, err := client.UploadChatFile(ctx, firstUser.OrganizationID, "image/png", "one-too-many.png", bytes.NewReader(pngData))
+		require.NoError(t, err)
+
+		// Sending a message with the extra file should succeed
+		// (message goes through) but the file should NOT be linked
+		// (cap enforced in SQL). The response includes a warning.
+		msgResp, err := client.CreateChatMessage(ctx, chat.ID, codersdk.CreateChatMessageRequest{
+			Content: []codersdk.ChatInputPart{
+				{Type: codersdk.ChatInputPartTypeText, Text: "one too many"},
+				{Type: codersdk.ChatInputPartTypeFile, FileID: extraResp.ID},
+			},
+		})
+		require.NoError(t, err)
+		require.NotEmpty(t, msgResp.Warnings, "response should warn about unlinked files")
+		require.Contains(t, msgResp.Warnings[0], "file linking skipped")
+
+		// The extra file should NOT appear in the chat's files.
+		chatResult, err := client.GetChat(ctx, chat.ID)
+		require.NoError(t, err)
+		require.Len(t, chatResult.Files, codersdk.MaxChatFileIDs,
+			"file count should not exceed the cap")
+
+		// Sending a message referencing an already-linked file
+		// should succeed with no warnings (dedup, no array growth).
+		msgResp2, err := client.CreateChatMessage(ctx, chat.ID, codersdk.CreateChatMessageRequest{
+			Content: []codersdk.ChatInputPart{
+				{Type: codersdk.ChatInputPartTypeText, Text: "re-reference existing"},
+				{Type: codersdk.ChatInputPartTypeFile, FileID: fileIDs[0]},
+			},
+		})
+		require.NoError(t, err)
+		require.Empty(t, msgResp2.Warnings, "re-referencing an existing file should not warn")
+	})
+
+	t.Run("FileCapOnCreate", func(t *testing.T) {
+		t.Parallel()
+
+		ctx := testutil.Context(t, testutil.WaitLong)
+		client := newChatClient(t)
+		firstUser := coderdtest.CreateFirstUser(t, client.Client)
+		_ = createChatModelConfig(t, client)
+
+		pngData := append([]byte{0x89, 0x50, 0x4E, 0x47, 0x0D, 0x0A, 0x1A, 0x0A}, make([]byte, 64)...)
+
+		// Upload MaxChatFileIDs + 1 files.
+		fileIDs := make([]uuid.UUID, 0, codersdk.MaxChatFileIDs+1)
+		for i := range codersdk.MaxChatFileIDs + 1 {
+			resp, err := client.UploadChatFile(ctx, firstUser.OrganizationID, "image/png", fmt.Sprintf("create%d.png", i), bytes.NewReader(pngData))
+			require.NoError(t, err)
+			fileIDs = append(fileIDs, resp.ID)
+		}
+
+		// Create a chat with all files (one over the cap).
+		parts := []codersdk.ChatInputPart{
+			{Type: codersdk.ChatInputPartTypeText, Text: "over cap on create"},
+		}
+		for _, fid := range fileIDs {
+			parts = append(parts, codersdk.ChatInputPart{Type: codersdk.ChatInputPartTypeFile, FileID: fid})
+		}
+		chat, err := client.CreateChat(ctx, codersdk.CreateChatRequest{Content: parts})
+		require.NoError(t, err, "chat creation should succeed even when cap is exceeded")
+		require.NotEmpty(t, chat.Warnings, "response should warn about unlinked files")
+		require.Contains(t, chat.Warnings[0], "file linking skipped")
+
+		// Only MaxChatFileIDs files should actually be linked.
+		// With SQL-level batch rejection, ALL files are rejected
+		// when the result would exceed the cap. Since we're
+		// sending MaxChatFileIDs+1 files, the deduped count is
+		// 21 > 20, so 0 rows are affected and all files are
+		// unlinked.
+		chatResult, err := client.GetChat(ctx, chat.ID)
+		require.NoError(t, err)
+		require.Empty(t, chatResult.Files, "no files should be linked when batch exceeds cap")
+	})
 }

 func TestPatchChatMessage(t *testing.T) {
@@ -4446,11 +4791,11 @@ func TestPatchChatMessage(t *testing.T) {
 		require.NoError(t, err)
 		// The edited message is soft-deleted and a new one is inserted,
 		// so the returned ID will differ from the original.
-		require.NotEqual(t, userMessageID, edited.ID)
-		require.Equal(t, codersdk.ChatMessageRoleUser, edited.Role)
+		require.NotEqual(t, userMessageID, edited.Message.ID)
+		require.Equal(t, codersdk.ChatMessageRoleUser, edited.Message.Role)

 		foundEditedText := false
-		for _, part := range edited.Content {
+		for _, part := range edited.Message.Content {
 			if part.Type == codersdk.ChatMessagePartTypeText && part.Text == "hello after edit" {
 				foundEditedText = true
 			}
@@ -4538,11 +4883,11 @@ func TestPatchChatMessage(t *testing.T) {
 		require.NoError(t, err)
 		// The edited message is soft-deleted and a new one is inserted,
 		// so the returned ID will differ from the original.
-		require.NotEqual(t, userMessageID, edited.ID)
+		require.NotEqual(t, userMessageID, edited.Message.ID)

 		// Assert the edit response preserves the file_id.
 		var foundText, foundFile bool
-		for _, part := range edited.Content {
+		for _, part := range edited.Message.Content {
 			if part.Type == codersdk.ChatMessagePartTypeText && part.Text == "after edit with file" {
 				foundText = true
 			}
@@ -4685,6 +5030,112 @@ func TestPatchChatMessage(t *testing.T) {
 		sdkErr := requireSDKError(t, err, http.StatusBadRequest)
 		require.Equal(t, "Invalid chat message ID.", sdkErr.Message)
 	})
+
+	t.Run("FilesLinkedOnEdit", func(t *testing.T) {
+		t.Parallel()
+
+		ctx := testutil.Context(t, testutil.WaitLong)
+		client := newChatClient(t)
+		firstUser := coderdtest.CreateFirstUser(t, client.Client)
+		_ = createChatModelConfig(t, client)
+
+		// Create a text-only chat.
+		chat, err := client.CreateChat(ctx, codersdk.CreateChatRequest{
+			Content: []codersdk.ChatInputPart{
+				{Type: codersdk.ChatInputPartTypeText, Text: "before file edit"},
+			},
+		})
+		require.NoError(t, err)
+
+		// Upload a file.
+		pngData := append([]byte{0x89, 0x50, 0x4E, 0x47, 0x0D, 0x0A, 0x1A, 0x0A}, make([]byte, 64)...)
+		uploadResp, err := client.UploadChatFile(ctx, firstUser.OrganizationID, "image/png", "edit-linked.png", bytes.NewReader(pngData))
+		require.NoError(t, err)
+
+		// Find the user message ID.
+		messagesResult, err := client.GetChatMessages(ctx, chat.ID, nil)
+		require.NoError(t, err)
+		var userMessageID int64
+		for _, msg := range messagesResult.Messages {
+			if msg.Role == codersdk.ChatMessageRoleUser {
+				userMessageID = msg.ID
+				break
+			}
+		}
+		require.NotZero(t, userMessageID)
+
+		// Edit the message to include the file.
+		_, err = client.EditChatMessage(ctx, chat.ID, userMessageID, codersdk.EditChatMessageRequest{
+			Content: []codersdk.ChatInputPart{
+				{Type: codersdk.ChatInputPartTypeText, Text: "after file edit"},
+				{Type: codersdk.ChatInputPartTypeFile, FileID: uploadResp.ID},
+			},
+		})
+		require.NoError(t, err)
+
+		// GET the chat — file should be linked.
+		chatResult, err := client.GetChat(ctx, chat.ID)
+		require.NoError(t, err)
+		require.Len(t, chatResult.Files, 1)
+		f := chatResult.Files[0]
+		require.Equal(t, uploadResp.ID, f.ID)
+		require.Equal(t, "edit-linked.png", f.Name)
+		require.Equal(t, "image/png", f.MimeType)
+	})
+
+	t.Run("CapExceededOnEdit", func(t *testing.T) {
+		t.Parallel()
+
+		ctx := testutil.Context(t, testutil.WaitLong)
+		client := newChatClient(t)
+		firstUser := coderdtest.CreateFirstUser(t, client.Client)
+		_ = createChatModelConfig(t, client)
+
+		// Create a chat with MaxChatFileIDs files already linked.
+		parts := []codersdk.ChatInputPart{
+			{Type: codersdk.ChatInputPartTypeText, Text: "fill to cap"},
+		}
+		pngData := append([]byte{0x89, 0x50, 0x4E, 0x47, 0x0D, 0x0A, 0x1A, 0x0A}, make([]byte, 64)...)
+		for i := range codersdk.MaxChatFileIDs {
+			up, err := client.UploadChatFile(ctx, firstUser.OrganizationID, "image/png", fmt.Sprintf("cap-%d.png", i), bytes.NewReader(pngData))
+			require.NoError(t, err)
+			parts = append(parts, codersdk.ChatInputPart{Type: codersdk.ChatInputPartTypeFile, FileID: up.ID})
+		}
+		chat, err := client.CreateChat(ctx, codersdk.CreateChatRequest{Content: parts})
+		require.NoError(t, err)
+		require.Empty(t, chat.Warnings, "all files should link on create")
+
+		// Find the user message.
+		messagesResult, err := client.GetChatMessages(ctx, chat.ID, nil)
+		require.NoError(t, err)
+		var userMessageID int64
+		for _, msg := range messagesResult.Messages {
+			if msg.Role == codersdk.ChatMessageRoleUser {
+				userMessageID = msg.ID
+				break
+			}
+		}
+		require.NotZero(t, userMessageID)
+
+		// Upload one more file and try to link via edit.
+		extra, err := client.UploadChatFile(ctx, firstUser.OrganizationID, "image/png", "one-too-many.png", bytes.NewReader(pngData))
+		require.NoError(t, err)
+		edited, err := client.EditChatMessage(ctx, chat.ID, userMessageID, codersdk.EditChatMessageRequest{
+			Content: []codersdk.ChatInputPart{
+				{Type: codersdk.ChatInputPartTypeText, Text: "edit with extra file"},
+				{Type: codersdk.ChatInputPartTypeFile, FileID: extra.ID},
+			},
+		})
+		require.NoError(t, err)
+		require.NotEmpty(t, edited.Warnings, "edit should surface cap warning")
+		require.Contains(t, edited.Warnings[0], "file linking skipped")
+
+		// Verify the cap is still enforced.
+		chatResult, err := client.GetChat(ctx, chat.ID)
+		require.NoError(t, err)
+		require.Len(t, chatResult.Files, codersdk.MaxChatFileIDs,
+			"file count should not exceed the cap")
+	})
 }

 func TestStreamChat(t *testing.T) {
@@ -6177,7 +6628,7 @@ func seedChatCostFixture(t *testing.T) chatCostTestFixture {
 		ContextLimit:        []int64{0, 0},
 		Compressed:          []bool{false, false},
 		TotalCostMicros:     []int64{500, 500},
-		RuntimeMs:           []int64{0, 0},
+		RuntimeMs:           []int64{1500, 2500},
 	})
 	require.NoError(t, err)
 	require.Len(t, results, 2)
@@ -6210,16 +6661,19 @@ func assertChatCostSummary(t *testing.T, summary codersdk.ChatCostSummary, model
 	require.Equal(t, int64(0), summary.UnpricedMessageCount)
 	require.Equal(t, int64(200), summary.TotalInputTokens)
 	require.Equal(t, int64(100), summary.TotalOutputTokens)
+	require.Equal(t, int64(4000), summary.TotalRuntimeMs)

 	require.Len(t, summary.ByModel, 1)
 	require.Equal(t, modelConfigID, summary.ByModel[0].ModelConfigID)
 	require.Equal(t, int64(1000), summary.ByModel[0].TotalCostMicros)
 	require.Equal(t, int64(2), summary.ByModel[0].MessageCount)
+	require.Equal(t, int64(4000), summary.ByModel[0].TotalRuntimeMs)

 	require.Len(t, summary.ByChat, 1)
 	require.Equal(t, chatID, summary.ByChat[0].RootChatID)
 	require.Equal(t, int64(1000), summary.ByChat[0].TotalCostMicros)
 	require.Equal(t, int64(2), summary.ByChat[0].MessageCount)
+	require.Equal(t, int64(4000), summary.ByChat[0].TotalRuntimeMs)
 }

 func TestChatCostSummary(t *testing.T) {
@@ -298,6 +298,40 @@ neq(input.object.owner, "");
 			ExpectedSQL:       p("'' = 'org-id'"),
 			VariableConverter: regosql.ChatConverter(),
 		},
+		{
+			Name: "AuditLogUUID",
+			Queries: []string{
+				`"8c0b9bdc-a013-4b14-a49b-5747bc335708" = input.object.org_owner`,
+				`input.object.org_owner != ""`,
+				`neq(input.object.org_owner, "8c0b9bdc-a013-4b14-a49b-5747bc335708")`,
+				`input.object.org_owner in {"8c0b9bdc-a013-4b14-a49b-5747bc335708", "05f58202-4bfc-43ce-9ba4-5ff6e0174a71"}`,
+				`"read" in input.object.acl_group_list[input.object.org_owner]`,
+			},
+			ExpectedSQL: p(
+				p("audit_logs.organization_id = '8c0b9bdc-a013-4b14-a49b-5747bc335708'::uuid") + " OR " +
+					p("audit_logs.organization_id IS NOT NULL") + " OR " +
+					p("audit_logs.organization_id != '8c0b9bdc-a013-4b14-a49b-5747bc335708'::uuid") + " OR " +
+					p("audit_logs.organization_id = ANY(ARRAY ['05f58202-4bfc-43ce-9ba4-5ff6e0174a71'::uuid,'8c0b9bdc-a013-4b14-a49b-5747bc335708'::uuid])") + " OR " +
+					"(false)"),
+			VariableConverter: regosql.AuditLogConverter(),
+		},
+		{
+			Name: "ConnectionLogUUID",
+			Queries: []string{
+				`"8c0b9bdc-a013-4b14-a49b-5747bc335708" = input.object.org_owner`,
+				`input.object.org_owner != ""`,
+				`neq(input.object.org_owner, "8c0b9bdc-a013-4b14-a49b-5747bc335708")`,
+				`input.object.org_owner in {"8c0b9bdc-a013-4b14-a49b-5747bc335708"}`,
+				`"read" in input.object.acl_group_list[input.object.org_owner]`,
+			},
+			ExpectedSQL: p(
+				p("connection_logs.organization_id = '8c0b9bdc-a013-4b14-a49b-5747bc335708'::uuid") + " OR " +
+					p("connection_logs.organization_id IS NOT NULL") + " OR " +
+					p("connection_logs.organization_id != '8c0b9bdc-a013-4b14-a49b-5747bc335708'::uuid") + " OR " +
+					p("connection_logs.organization_id = ANY(ARRAY ['8c0b9bdc-a013-4b14-a49b-5747bc335708'::uuid])") + " OR " +
+					"(false)"),
+			VariableConverter: regosql.ConnectionLogConverter(),
+		},
 	}

 	for _, tc := range testCases {
@@ -53,7 +53,7 @@ func WorkspaceConverter() *sqltypes.VariableConverter {
 func AuditLogConverter() *sqltypes.VariableConverter {
 	matcher := sqltypes.NewVariableConverter().RegisterMatcher(
 		resourceIDMatcher(),
-		sqltypes.StringVarMatcher("COALESCE(audit_logs.organization_id :: text, '')", []string{"input", "object", "org_owner"}),
+		sqltypes.UUIDVarMatcher("audit_logs.organization_id", []string{"input", "object", "org_owner"}),
 		// Audit logs have no user owner, only owner by an organization.
 		sqltypes.AlwaysFalse(userOwnerMatcher()),
 	)
@@ -67,7 +67,7 @@ func AuditLogConverter() *sqltypes.VariableConverter {
 func ConnectionLogConverter() *sqltypes.VariableConverter {
 	matcher := sqltypes.NewVariableConverter().RegisterMatcher(
 		resourceIDMatcher(),
-		sqltypes.StringVarMatcher("COALESCE(connection_logs.organization_id :: text, '')", []string{"input", "object", "org_owner"}),
+		sqltypes.UUIDVarMatcher("connection_logs.organization_id", []string{"input", "object", "org_owner"}),
 		// Connection logs have no user owner, only owner by an organization.
 		sqltypes.AlwaysFalse(userOwnerMatcher()),
 	)
@@ -0,0 +1,114 @@
+package sqltypes
+
+import (
+	"fmt"
+	"strings"
+
+	"github.com/open-policy-agent/opa/ast"
+	"golang.org/x/xerrors"
+)
+
+var (
+	_ VariableMatcher  = astUUIDVar{}
+	_ Node             = astUUIDVar{}
+	_ SupportsEquality = astUUIDVar{}
+)
+
+// astUUIDVar is a variable that represents a UUID column. Unlike
+// astStringVar it emits native UUID comparisons (column = 'val'::uuid)
+// instead of text-based ones (COALESCE(column::text, ”) = 'val').
+// This allows PostgreSQL to use indexes on UUID columns.
+type astUUIDVar struct {
+	Source       RegoSource
+	FieldPath    []string
+	ColumnString string
+}
+
+func UUIDVarMatcher(sqlColumn string, regoPath []string) VariableMatcher {
+	return astUUIDVar{FieldPath: regoPath, ColumnString: sqlColumn}
+}
+
+func (astUUIDVar) UseAs() Node { return astUUIDVar{} }
+
+func (u astUUIDVar) ConvertVariable(rego ast.Ref) (Node, bool) {
+	left, err := RegoVarPath(u.FieldPath, rego)
+	if err == nil && len(left) == 0 {
+		return astUUIDVar{
+			Source:       RegoSource(rego.String()),
+			FieldPath:    u.FieldPath,
+			ColumnString: u.ColumnString,
+		}, true
+	}
+
+	return nil, false
+}
+
+func (u astUUIDVar) SQLString(_ *SQLGenerator) string {
+	return u.ColumnString
+}
+
+// EqualsSQLString handles equality comparisons for UUID columns.
+// Rego always produces string literals, so we accept AstString and
+// cast the literal to ::uuid in the output SQL. This lets PG use
+// native UUID indexes instead of falling back to text comparisons.
+// nolint:revive
+func (u astUUIDVar) EqualsSQLString(cfg *SQLGenerator, not bool, other Node) (string, error) {
+	switch other.UseAs().(type) {
+	case AstString:
+		// The other side is a rego string literal like
+		// "8c0b9bdc-a013-4b14-a49b-5747bc335708". Emit a comparison
+		// that casts the literal to uuid so PG can use indexes:
+		//   column = 'val'::uuid
+		// instead of the text-based:
+		//   'val' = COALESCE(column::text, '')
+		s, ok := other.(AstString)
+		if !ok {
+			return "", xerrors.Errorf("expected AstString, got %T", other)
+		}
+		if s.Value == "" {
+			// Empty string in rego means "no value". Compare the
+			// column against NULL since UUID columns represent
+			// absent values as NULL, not empty strings.
+			op := "IS NULL"
+			if not {
+				op = "IS NOT NULL"
+			}
+			return fmt.Sprintf("%s %s", u.ColumnString, op), nil
+		}
+		return fmt.Sprintf("%s %s '%s'::uuid",
+			u.ColumnString, equalsOp(not), s.Value), nil
+	case astUUIDVar:
+		return basicSQLEquality(cfg, not, u, other), nil
+	default:
+		return "", xerrors.Errorf("unsupported equality: %T %s %T",
+			u, equalsOp(not), other)
+	}
+}
+
+// ContainedInSQL implements SupportsContainedIn so that a UUID column
+// can appear in membership checks like `col = ANY(ARRAY[...])`. The
+// array elements are rego strings, so we cast each to ::uuid.
+func (u astUUIDVar) ContainedInSQL(_ *SQLGenerator, haystack Node) (string, error) {
+	arr, ok := haystack.(ASTArray)
+	if !ok {
+		return "", xerrors.Errorf("unsupported containedIn: %T in %T", u, haystack)
+	}
+
+	if len(arr.Value) == 0 {
+		return "false", nil
+	}
+
+	// Build ARRAY['uuid1'::uuid, 'uuid2'::uuid, ...]
+	values := make([]string, 0, len(arr.Value))
+	for _, v := range arr.Value {
+		s, ok := v.(AstString)
+		if !ok {
+			return "", xerrors.Errorf("expected AstString array element, got %T", v)
+		}
+		values = append(values, fmt.Sprintf("'%s'::uuid", s.Value))
+	}
+
+	return fmt.Sprintf("%s = ANY(ARRAY [%s])",
+		u.ColumnString,
+		strings.Join(values, ",")), nil
+}
@@ -66,7 +66,7 @@ func AuditLogs(ctx context.Context, db database.Store, query string) (database.G
 	}

 	// Prepare the count filter, which uses the same parameters as the GetAuditLogsOffsetParams.
-	// nolint:exhaustruct // UserID is not obtained from the query parameters.
+	// nolint:exhaustruct // UserID and CountCap are not obtained from the query parameters.
 	countFilter := database.CountAuditLogsParams{
 		RequestID:      filter.RequestID,
 		ResourceID:     filter.ResourceID,
@@ -123,6 +123,7 @@ func ConnectionLogs(ctx context.Context, db database.Store, query string, apiKey
 	}

 	// This MUST be kept in sync with the above
+	// nolint:exhaustruct // CountCap is not obtained from the query parameters.
 	countFilter := database.CountConnectionLogsParams{
 		OrganizationID:      filter.OrganizationID,
 		WorkspaceOwner:      filter.WorkspaceOwner,
@@ -7,6 +7,7 @@ import (
 	"encoding/json"
 	"errors"
 	"fmt"
+	"maps"
 	"net/http"
 	"slices"
 	"strconv"
@@ -90,6 +91,12 @@ const (
 	// goroutines and lifecycle management.
 	streamDropWarnInterval = 10 * time.Second

+	// bufferRetainGracePeriod is how long the message_part
+	// buffer is kept after processing completes. This gives
+	// cross-replica relay subscribers time to connect and
+	// snapshot the buffer before it is garbage-collected.
+	bufferRetainGracePeriod = 5 * time.Second
+
 	// DefaultMaxChatsPerAcquire is the maximum number of chats to
 	// acquire in a single processOnce call. Batching avoids
 	// waiting a full polling interval between acquisitions
@@ -145,6 +152,12 @@ type Server struct {
 	inFlightChatStaleAfter     time.Duration
 	chatHeartbeatInterval      time.Duration

+	// heartbeatMu guards heartbeatRegistry.
+	heartbeatMu sync.Mutex
+	// heartbeatRegistry maps chat IDs to their cancel functions
+	// and workspace state for the centralized heartbeat loop.
+	heartbeatRegistry map[uuid.UUID]*heartbeatEntry
+
 	// wakeCh is signaled by SendMessage, EditMessage, CreateChat,
 	// and PromoteQueued so the run loop calls processOnce
 	// immediately instead of waiting for the next ticker.
@@ -691,6 +704,24 @@ type chatStreamState struct {
 	bufferLastWarnAt     time.Time
 	subscriberDropCount  int64
 	subscriberLastWarnAt time.Time
+	// bufferRetainedAt records when processing completed and
+	// the buffer was retained for late-connecting relay
+	// subscribers. Zero while buffering is active. When
+	// non-zero, cleanupStreamIfIdle skips GC until the grace
+	// period expires so cross-replica relays can still
+	// snapshot the buffer.
+	bufferRetainedAt time.Time
+}
+
+// heartbeatEntry tracks a single chat's cancel function and workspace
+// state for the centralized heartbeat loop. Instead of spawning a
+// per-chat goroutine, processChat registers an entry here and the
+// single heartbeatLoop goroutine handles all chats.
+type heartbeatEntry struct {
+	cancelWithCause context.CancelCauseFunc
+	chatID          uuid.UUID
+	workspaceID     uuid.NullUUID
+	logger          slog.Logger
 }

 // resetDropCounters zeroes the rate-limiting state for both buffer
@@ -873,7 +904,8 @@ func (p *Server) CreateChat(ctx context.Context, opts CreateOptions) (database.C
 			return xerrors.Errorf("insert chat: %w", err)
 		}

-		systemPrompt := strings.TrimSpace(opts.SystemPrompt)
+		deploymentPrompt := p.resolveDeploymentSystemPrompt(ctx)
+		userPrompt := SanitizePromptText(opts.SystemPrompt)
 		var workspaceAwareness string
 		if opts.WorkspaceID.Valid {
 			workspaceAwareness = "This chat is attached to a workspace. You can use workspace tools like execute, read_file, write_file, etc."
@@ -895,16 +927,32 @@ func (p *Server) CreateChat(ctx context.Context, opts CreateOptions) (database.C
 			ChatID: insertedChat.ID,
 		}

-		if systemPrompt != "" {
-			systemContent, err := chatprompt.MarshalParts([]codersdk.ChatMessagePart{
-				codersdk.ChatMessageText(systemPrompt),
+		if deploymentPrompt != "" {
+			deploymentContent, err := chatprompt.MarshalParts([]codersdk.ChatMessagePart{
+				codersdk.ChatMessageText(deploymentPrompt),
 			})
 			if err != nil {
-				return xerrors.Errorf("marshal system prompt: %w", err)
+				return xerrors.Errorf("marshal deployment system prompt: %w", err)
 			}
 			appendChatMessage(&msgParams, newChatMessage(
 				database.ChatMessageRoleSystem,
-				systemContent,
+				deploymentContent,
+				database.ChatMessageVisibilityModel,
+				opts.ModelConfigID,
+				chatprompt.CurrentContentVersion,
+			))
+		}
+
+		if userPrompt != "" {
+			userPromptContent, err := chatprompt.MarshalParts([]codersdk.ChatMessagePart{
+				codersdk.ChatMessageText(userPrompt),
+			})
+			if err != nil {
+				return xerrors.Errorf("marshal user system prompt: %w", err)
+			}
+			appendChatMessage(&msgParams, newChatMessage(
+				database.ChatMessageRoleSystem,
+				userPromptContent,
 				database.ChatMessageVisibilityModel,
 				opts.ModelConfigID,
 				chatprompt.CurrentContentVersion,
@@ -2390,8 +2438,8 @@ func New(cfg Config) *Server {
 		clock:                          clk,
 		recordingSem:                   make(chan struct{}, maxConcurrentRecordingUploads),
 		wakeCh:                         make(chan struct{}, 1),
+		heartbeatRegistry:              make(map[uuid.UUID]*heartbeatEntry),
 	}
-
 	//nolint:gocritic // The chat processor uses a scoped chatd context.
 	ctx = dbauthz.AsChatd(ctx)

@@ -2431,6 +2479,9 @@ func (p *Server) start(ctx context.Context) {
 	// to handle chats orphaned by crashed or redeployed workers.
 	p.recoverStaleChats(ctx)

+	// Single heartbeat loop for all chats on this replica.
+	go p.heartbeatLoop(ctx)
+
 	acquireTicker := p.clock.NewTicker(
 		p.pendingChatAcquireInterval,
 		"chatd",
@@ -2681,11 +2732,113 @@ func (p *Server) getOrCreateStreamState(chatID uuid.UUID) *chatStreamState {

 // cleanupStreamIfIdle removes the chat entry from the sync.Map
 // when there are no subscribers and the stream is not buffering.
+// When bufferRetainedAt is set, cleanup is deferred until the
+// grace period expires so cross-replica relay subscribers can
+// still snapshot the buffer.
 // The caller must hold state.mu.
 func (p *Server) cleanupStreamIfIdle(chatID uuid.UUID, state *chatStreamState) {
-	if !state.buffering && len(state.subscribers) == 0 {
-		p.chatStreams.Delete(chatID)
-		p.workspaceMCPToolsCache.Delete(chatID)
+	if state.buffering || len(state.subscribers) > 0 {
+		return
+	}
+	// Keep stream state alive during the grace period so
+	// late-connecting relay subscribers can snapshot the
+	// buffer after the worker finishes processing.
+	if !state.bufferRetainedAt.IsZero() &&
+		p.clock.Now().Before(state.bufferRetainedAt.Add(bufferRetainGracePeriod)) {
+		return
+	}
+	p.chatStreams.Delete(chatID)
+	p.workspaceMCPToolsCache.Delete(chatID)
+}
+
+// registerHeartbeat enrolls a chat in the centralized batch
+// heartbeat loop. Must be called after chatCtx is created.
+func (p *Server) registerHeartbeat(entry *heartbeatEntry) {
+	p.heartbeatMu.Lock()
+	defer p.heartbeatMu.Unlock()
+	if _, exists := p.heartbeatRegistry[entry.chatID]; exists {
+		p.logger.Warn(context.Background(),
+			"duplicate heartbeat registration, skipping",
+			slog.F("chat_id", entry.chatID))
+		return
+	}
+	p.heartbeatRegistry[entry.chatID] = entry
+}
+
+// unregisterHeartbeat removes a chat from the centralized
+// heartbeat loop when chat processing finishes.
+func (p *Server) unregisterHeartbeat(chatID uuid.UUID) {
+	p.heartbeatMu.Lock()
+	defer p.heartbeatMu.Unlock()
+	delete(p.heartbeatRegistry, chatID)
+}
+
+// heartbeatLoop runs in a single goroutine, issuing one batch
+// heartbeat query per interval for all registered chats.
+func (p *Server) heartbeatLoop(ctx context.Context) {
+	ticker := p.clock.NewTicker(p.chatHeartbeatInterval, "chatd", "batch-heartbeat")
+	defer ticker.Stop()
+	for {
+		select {
+		case <-ctx.Done():
+			return
+		case <-ticker.C:
+			p.heartbeatTick(ctx)
+		}
+	}
+}
+
+// heartbeatTick issues a single batch UPDATE for all running chats
+// owned by this worker. Chats missing from the result set are
+// interrupted (stolen by another replica or already completed).
+func (p *Server) heartbeatTick(ctx context.Context) {
+	// Snapshot the registry under the lock.
+	p.heartbeatMu.Lock()
+	snapshot := maps.Clone(p.heartbeatRegistry)
+	p.heartbeatMu.Unlock()
+
+	if len(snapshot) == 0 {
+		return
+	}
+
+	// Collect the IDs we believe we own.
+	ids := slices.Collect(maps.Keys(snapshot))
+
+	//nolint:gocritic // AsChatd provides narrowly-scoped daemon
+	// access for batch-updating heartbeats.
+	chatdCtx := dbauthz.AsChatd(ctx)
+	updatedIDs, err := p.db.UpdateChatHeartbeats(chatdCtx, database.UpdateChatHeartbeatsParams{
+		IDs:      ids,
+		WorkerID: p.workerID,
+		Now:      p.clock.Now(),
+	})
+	if err != nil {
+		p.logger.Error(ctx, "batch heartbeat failed", slog.Error(err))
+		return
+	}
+
+	// Build a set of IDs that were successfully updated.
+	updated := make(map[uuid.UUID]struct{}, len(updatedIDs))
+	for _, id := range updatedIDs {
+		updated[id] = struct{}{}
+	}
+
+	// Interrupt registered chats that were not in the result
+	// (stolen by another replica or already completed).
+	for id, entry := range snapshot {
+		if _, ok := updated[id]; !ok {
+			entry.logger.Warn(ctx, "chat not in batch heartbeat result, interrupting")
+			entry.cancelWithCause(chatloop.ErrInterrupted)
+			continue
+		}
+		// Bump workspace usage for surviving chats.
+		newWsID := p.trackWorkspaceUsage(ctx, entry.chatID, entry.workspaceID, entry.logger)
+		// Update workspace ID in the registry for next tick.
+		p.heartbeatMu.Lock()
+		if current, exists := p.heartbeatRegistry[id]; exists {
+			current.workspaceID = newWsID
+		}
+		p.heartbeatMu.Unlock()
 	}
 }

@@ -3163,7 +3316,11 @@ func (p *Server) publishChatPubsubEvent(chat database.Chat, kind coderdpubsub.Ch
 	if p.pubsub == nil {
 		return
 	}
-	sdkChat := db2sdk.Chat(chat, nil) // we have diffStatus already converted
+	// diffStatus is applied below. File metadata is intentionally
+	// omitted from pubsub events to avoid an extra DB query per
+	// publish. Clients must merge pubsub updates, not replace
+	// cached file metadata.
+	sdkChat := db2sdk.Chat(chat, nil, nil)
 	if diffStatus != nil {
 		sdkChat.DiffStatus = diffStatus
 	}
@@ -3530,33 +3687,17 @@ func (p *Server) processChat(ctx context.Context, chat database.Chat) {
 		}
 	}()

-	// Periodically update the heartbeat so other replicas know this
-	// worker is still alive. The goroutine stops when chatCtx is
-	// canceled (either by completion or interruption).
-	go func() {
-		ticker := p.clock.NewTicker(p.chatHeartbeatInterval, "chatd", "heartbeat")
-		defer ticker.Stop()
-		for {
-			select {
-			case <-chatCtx.Done():
-				return
-			case <-ticker.C:
-				rows, err := p.db.UpdateChatHeartbeat(chatCtx, database.UpdateChatHeartbeatParams{
-					ID:       chat.ID,
-					WorkerID: p.workerID,
-				})
-				if err != nil {
-					logger.Warn(chatCtx, "failed to update chat heartbeat", slog.Error(err))
-					continue
-				}
-				if rows == 0 {
-					cancel(chatloop.ErrInterrupted)
-					return
-				}
-				chat.WorkspaceID = p.trackWorkspaceUsage(chatCtx, chat.ID, chat.WorkspaceID, logger)
-			}
-		}
-	}()
+	// Register with the centralized heartbeat loop instead of
+	// running a per-chat goroutine. The loop issues a single batch
+	// UPDATE for all chats on this worker and detects stolen chats
+	// via set-difference.
+	p.registerHeartbeat(&heartbeatEntry{
+		cancelWithCause: cancel,
+		chatID:          chat.ID,
+		workspaceID:     chat.WorkspaceID,
+		logger:          logger,
+	})
+	defer p.unregisterHeartbeat(chat.ID)

 	// Start buffering stream events BEFORE publishing the running
 	// status. This closes a race where a subscriber sees
@@ -3567,15 +3708,20 @@ func (p *Server) processChat(ctx context.Context, chat database.Chat) {
 	streamState := p.getOrCreateStreamState(chat.ID)
 	streamState.mu.Lock()
 	streamState.buffer = nil
+	streamState.bufferRetainedAt = time.Time{}
 	streamState.resetDropCounters()
 	streamState.buffering = true
 	streamState.mu.Unlock()
 	defer func() {
 		streamState.mu.Lock()
-		streamState.buffer = nil
 		streamState.resetDropCounters()
 		streamState.buffering = false
-		p.cleanupStreamIfIdle(chat.ID, streamState)
+		// Retain the buffer for a grace period so
+		// cross-replica relay subscribers can still snapshot
+		// it after processing completes. The buffer is
+		// cleared when the next processChat starts or when
+		// cleanupStreamIfIdle runs after the grace period.
+		streamState.bufferRetainedAt = p.clock.Now()
 		streamState.mu.Unlock()
 	}()

@@ -3905,14 +4051,6 @@ func (p *Server) runChat(
 		)
 	}()

-	prompt, err := chatprompt.ConvertMessagesWithFiles(ctx, messages, p.chatFileResolver(), logger)
-	if err != nil {
-		return result, xerrors.Errorf("build chat prompt: %w", err)
-	}
-	if chat.ParentChatID.Valid {
-		prompt = chatprompt.InsertSystem(prompt, defaultSubagentInstruction)
-	}
-
 	// Detect computer-use subagent via the mode column.
 	isComputerUse := chat.Mode.Valid && chat.Mode.ChatMode == database.ChatModeComputerUse

@@ -3969,7 +4107,20 @@ func (p *Server) runChat(
 			needsInstructionPersist = true
 		}
 	}
+	// Convert messages to prompt format in parallel with g2 work.
+	// ConvertMessagesWithFiles only reads `messages` (available
+	// after g.Wait()) and resolves file references via the DB.
+	// No g2 task reads or writes `prompt`, so this is safe.
+	var prompt []fantasy.Message
 	var g2 errgroup.Group
+	g2.Go(func() error {
+		var err error
+		prompt, err = chatprompt.ConvertMessagesWithFiles(ctx, messages, p.chatFileResolver(), logger)
+		if err != nil {
+			return xerrors.Errorf("build chat prompt: %w", err)
+		}
+		return nil
+	})
 	if needsInstructionPersist {
 		g2.Go(func() error {
 			var persistErr error
@@ -4083,8 +4234,12 @@ func (p *Server) runChat(
 			return nil
 		})
 	}
-	// All g2 goroutines return nil; error is discarded.
-	_ = g2.Wait()
+	if err := g2.Wait(); err != nil {
+		return result, err
+	}
+	if chat.ParentChatID.Valid {
+		prompt = chatprompt.InsertSystem(prompt, defaultSubagentInstruction)
+	}
 	if mcpCleanup != nil {
 		defer mcpCleanup()
 	}
@@ -4302,17 +4457,12 @@ func (p *Server) runChat(
 			p.publishMessage(chat.ID, msg)
 		}

-		// Clear the stream buffer now that the step is
-		// persisted. Late-joining subscribers will load
-		// these messages from the database instead.
-		if val, ok := p.chatStreams.Load(chat.ID); ok {
-			if ss, ok := val.(*chatStreamState); ok {
-				ss.mu.Lock()
-				ss.buffer = nil
-				ss.resetDropCounters()
-				ss.mu.Unlock()
-			}
-		}
+		// Do NOT clear the stream buffer here. Cross-replica
+		// relay subscribers may still need to snapshot buffered
+		// message_parts after processing completes. The buffer
+		// is bounded by maxStreamBufferSize and is cleared when
+		// the next processChat starts or when the stream state
+		// is garbage-collected after the retention grace period.

 		return nil
 	}
@@ -4475,6 +4625,27 @@ func (p *Server) runChat(
 					return uuid.Nil, xerrors.Errorf("insert chat file: %w", err)
 				}

+				// Cap enforcement and dedup are handled atomically
+				// in SQL. rejected > 0 = cap exceeded.
+				rejected, err := p.db.LinkChatFiles(ctx, database.LinkChatFilesParams{
+					ChatID:       chatSnapshot.ID,
+					MaxFileLinks: int32(codersdk.MaxChatFileIDs),
+					FileIds:      []uuid.UUID{row.ID},
+				})
+				switch {
+				case err != nil:
+					p.logger.Error(ctx, "failed to link file to chat",
+						slog.F("chat_id", chatSnapshot.ID),
+						slog.F("file_id", row.ID),
+						slog.Error(err),
+					)
+				case rejected > 0:
+					p.logger.Warn(ctx, "file cap reached, file not linked to chat",
+						slog.F("chat_id", chatSnapshot.ID),
+						slog.F("file_id", row.ID),
+						slog.F("max_file_links", codersdk.MaxChatFileIDs),
+					)
+				}
 				return row.ID, nil
 			},
 		}))
@@ -4547,7 +4718,7 @@ func (p *Server) runChat(
 		prompt = filterPromptForChainMode(prompt, chainInfo.trailingUserCount)
 	}

-	err = chatloop.Run(ctx, chatloop.RunOptions{
+	err := chatloop.Run(ctx, chatloop.RunOptions{
 		Model:    model,
 		Messages: prompt,
 		Tools:    tools, MaxSteps: maxChatSteps,
@@ -5196,6 +5367,37 @@ func (p *Server) resolveUserCompactionThreshold(ctx context.Context, userID uuid
 	return int32(val), true
 }

+// resolveDeploymentSystemPrompt builds the deployment-level system
+// prompt from the built-in default and the admin-configured custom
+// prompt stored in site_configs.
+func (p *Server) resolveDeploymentSystemPrompt(ctx context.Context) string {
+	config, err := p.db.GetChatSystemPromptConfig(ctx)
+	if err != nil {
+		// Fail open: use the built-in default so chats always have
+		// some system guidance.
+		p.logger.Error(ctx, "failed to fetch chat system prompt configuration, using default", slog.Error(err))
+		return DefaultSystemPrompt
+	}
+
+	sanitizedCustom := SanitizePromptText(config.ChatSystemPrompt)
+	if sanitizedCustom == "" && strings.TrimSpace(config.ChatSystemPrompt) != "" {
+		p.logger.Warn(ctx, "custom system prompt became empty after sanitization, omitting custom portion")
+	}
+
+	var parts []string
+	if config.IncludeDefaultSystemPrompt {
+		parts = append(parts, DefaultSystemPrompt)
+	}
+	if sanitizedCustom != "" {
+		parts = append(parts, sanitizedCustom)
+	}
+	result := strings.Join(parts, "\n\n")
+	if result == "" {
+		p.logger.Warn(ctx, "resolved system prompt is empty, no system prompt will be injected into chats")
+	}
+	return result
+}
+
 // resolveUserPrompt fetches the user's custom chat prompt from the
 // database and wraps it in <user-instructions> tags. Returns empty
 // string if no prompt is set.
@@ -21,6 +21,7 @@ import (
 	dbpubsub "github.com/coder/coder/v2/coderd/database/pubsub"
 	coderdpubsub "github.com/coder/coder/v2/coderd/pubsub"
 	"github.com/coder/coder/v2/coderd/x/chatd/chaterror"
+	"github.com/coder/coder/v2/coderd/x/chatd/chatloop"
 	"github.com/coder/coder/v2/coderd/x/chatd/chatprovider"
 	"github.com/coder/coder/v2/coderd/x/chatd/chattest"
 	"github.com/coder/coder/v2/coderd/x/chatd/chattool"
@@ -2071,6 +2072,7 @@ func TestProcessChat_IgnoresStaleControlNotification(t *testing.T) {
 		workerID:              workerID,
 		chatHeartbeatInterval: time.Minute,
 		configCache:           newChatConfigCache(ctx, db, clock),
+		heartbeatRegistry:     make(map[uuid.UUID]*heartbeatEntry),
 	}

 	// Publish a stale "pending" notification on the control channel
@@ -2133,3 +2135,130 @@ func TestProcessChat_IgnoresStaleControlNotification(t *testing.T) {
 	require.Equal(t, database.ChatStatusError, finalStatus,
 		"processChat should have reached runChat (error), not been interrupted (waiting)")
 }
+
+// TestHeartbeatTick_StolenChatIsInterrupted verifies that when the
+// batch heartbeat UPDATE does not return a registered chat's ID
+// (because another replica stole it or it was completed), the
+// heartbeat tick cancels that chat's context with ErrInterrupted
+// while leaving surviving chats untouched.
+func TestHeartbeatTick_StolenChatIsInterrupted(t *testing.T) {
+	t.Parallel()
+
+	ctx := testutil.Context(t, testutil.WaitShort)
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+	ctrl := gomock.NewController(t)
+	db := dbmock.NewMockStore(ctrl)
+	clock := quartz.NewMock(t)
+
+	workerID := uuid.New()
+
+	server := &Server{
+		db:                    db,
+		logger:                logger,
+		clock:                 clock,
+		workerID:              workerID,
+		chatHeartbeatInterval: time.Minute,
+		heartbeatRegistry:     make(map[uuid.UUID]*heartbeatEntry),
+	}
+
+	// Create three chats with independent cancel functions.
+	chat1 := uuid.New()
+	chat2 := uuid.New()
+	chat3 := uuid.New()
+
+	_, cancel1 := context.WithCancelCause(ctx)
+	_, cancel2 := context.WithCancelCause(ctx)
+	ctx3, cancel3 := context.WithCancelCause(ctx)
+
+	server.registerHeartbeat(&heartbeatEntry{
+		cancelWithCause: cancel1,
+		chatID:          chat1,
+		logger:          logger,
+	})
+	server.registerHeartbeat(&heartbeatEntry{
+		cancelWithCause: cancel2,
+		chatID:          chat2,
+		logger:          logger,
+	})
+	server.registerHeartbeat(&heartbeatEntry{
+		cancelWithCause: cancel3,
+		chatID:          chat3,
+		logger:          logger,
+	})
+
+	// The batch UPDATE returns only chat1 and chat2 —
+	// chat3 was "stolen" by another replica.
+	db.EXPECT().UpdateChatHeartbeats(gomock.Any(), gomock.Any()).DoAndReturn(
+		func(_ context.Context, params database.UpdateChatHeartbeatsParams) ([]uuid.UUID, error) {
+			require.Equal(t, workerID, params.WorkerID)
+			require.Len(t, params.IDs, 3)
+			// Return only chat1 and chat2 as surviving.
+			return []uuid.UUID{chat1, chat2}, nil
+		},
+	)
+
+	server.heartbeatTick(ctx)
+
+	// chat3's context should be canceled with ErrInterrupted.
+	require.ErrorIs(t, context.Cause(ctx3), chatloop.ErrInterrupted,
+		"stolen chat should be interrupted")
+
+	// chat3 should have been removed from the registry by
+	// unregister (in production this happens via defer in
+	// processChat). The heartbeat tick itself does not
+	// unregister — it only cancels. Verify the entry is
+	// still present (processChat's defer would clean it up).
+	server.heartbeatMu.Lock()
+	_, chat1Exists := server.heartbeatRegistry[chat1]
+	_, chat2Exists := server.heartbeatRegistry[chat2]
+	_, chat3Exists := server.heartbeatRegistry[chat3]
+	server.heartbeatMu.Unlock()
+
+	require.True(t, chat1Exists, "surviving chat1 should remain registered")
+	require.True(t, chat2Exists, "surviving chat2 should remain registered")
+	require.True(t, chat3Exists,
+		"stolen chat3 should still be in registry (processChat defer removes it)")
+}
+
+// TestHeartbeatTick_DBErrorDoesNotInterruptChats verifies that a
+// transient database failure causes the tick to log and return
+// without canceling any registered chats.
+func TestHeartbeatTick_DBErrorDoesNotInterruptChats(t *testing.T) {
+	t.Parallel()
+
+	ctx := testutil.Context(t, testutil.WaitShort)
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+	ctrl := gomock.NewController(t)
+	db := dbmock.NewMockStore(ctrl)
+	clock := quartz.NewMock(t)
+
+	server := &Server{
+		db:                    db,
+		logger:                logger,
+		clock:                 clock,
+		workerID:              uuid.New(),
+		chatHeartbeatInterval: time.Minute,
+		heartbeatRegistry:     make(map[uuid.UUID]*heartbeatEntry),
+	}
+
+	chatID := uuid.New()
+	chatCtx, cancel := context.WithCancelCause(ctx)
+
+	server.registerHeartbeat(&heartbeatEntry{
+		cancelWithCause: cancel,
+		chatID:          chatID,
+		logger:          logger,
+	})
+
+	// Simulate a transient DB error.
+	db.EXPECT().UpdateChatHeartbeats(gomock.Any(), gomock.Any()).Return(
+		nil, xerrors.New("connection reset"),
+	)
+
+	server.heartbeatTick(ctx)
+
+	// Chat should NOT be interrupted — the tick logged and
+	// returned early.
+	require.NoError(t, chatCtx.Err(),
+		"chat context should not be canceled on transient DB error")
+}
@@ -474,7 +474,7 @@ func TestArchiveChatInterruptsActiveProcessing(t *testing.T) {
 	require.Equal(t, 1, userMessages, "expected queued message to stay queued after archive")
 }

-func TestUpdateChatHeartbeatRequiresOwnership(t *testing.T) {
+func TestUpdateChatHeartbeatsRequiresOwnership(t *testing.T) {
 	t.Parallel()

 	db, ps := dbtestutil.NewDB(t)
@@ -501,19 +501,24 @@ func TestUpdateChatHeartbeatRequiresOwnership(t *testing.T) {
 	})
 	require.NoError(t, err)

-	rows, err := db.UpdateChatHeartbeat(ctx, database.UpdateChatHeartbeatParams{
-		ID:       chat.ID,
+	// Wrong worker_id should return no IDs.
+	ids, err := db.UpdateChatHeartbeats(ctx, database.UpdateChatHeartbeatsParams{
+		IDs:      []uuid.UUID{chat.ID},
 		WorkerID: uuid.New(),
+		Now:      time.Now(),
 	})
 	require.NoError(t, err)
-	require.Equal(t, int64(0), rows)
+	require.Empty(t, ids)

-	rows, err = db.UpdateChatHeartbeat(ctx, database.UpdateChatHeartbeatParams{
-		ID:       chat.ID,
+	// Correct worker_id should return the chat's ID.
+	ids, err = db.UpdateChatHeartbeats(ctx, database.UpdateChatHeartbeatsParams{
+		IDs:      []uuid.UUID{chat.ID},
 		WorkerID: workerID,
+		Now:      time.Now(),
 	})
 	require.NoError(t, err)
-	require.Equal(t, int64(1), rows)
+	require.Len(t, ids, 1)
+	require.Equal(t, chat.ID, ids[0])
 }

 func TestSendMessageQueueBehaviorQueuesWhenBusy(t *testing.T) {
@@ -70,8 +70,8 @@ func TestRun_ActiveToolsPrepareBehavior(t *testing.T) {
 	require.Equal(t, 1, persistStepCalls)
 	require.True(t, persistedStep.ContextLimit.Valid)
 	require.Equal(t, int64(4096), persistedStep.ContextLimit.Int64)
-	require.Greater(t, persistedStep.Runtime, time.Duration(0),
-		"step runtime should be positive")
+	require.GreaterOrEqual(t, persistedStep.Runtime, time.Duration(0),
+		"step runtime should be non-negative")

 	require.NotEmpty(t, capturedCall.Prompt)
 	require.False(t, containsPromptSentinel(capturedCall.Prompt))
@@ -1192,23 +1192,6 @@ func fileReferencePartToText(part codersdk.ChatMessagePart) string {
 	return sb.String()
 }

-// skillPartToText formats a skill SDK part as plain text for
-// LLM consumption. The user explicitly attached this skill chip
-// to their message, so the text makes clear they want the agent
-// to use the named skill (listed in <available-skills>).
-func skillPartToText(part codersdk.ChatMessagePart) string {
-	if part.SkillDescription != "" {
-		return fmt.Sprintf(
-			"Use the %q skill (%s). Read it with read_skill before following its instructions.",
-			part.SkillName, part.SkillDescription,
-		)
-	}
-	return fmt.Sprintf(
-		"Use the %q skill. Read it with read_skill before following its instructions.",
-		part.SkillName,
-	)
-}
-
 // toolResultPartToMessagePart converts an SDK tool-result part
 // into a fantasy ToolResultPart for LLM dispatch.
 func toolResultPartToMessagePart(logger slog.Logger, part codersdk.ChatMessagePart) fantasy.ToolResultPart {
@@ -1377,12 +1360,6 @@ func partsToMessageParts(
 			result = append(result, fantasy.TextPart{
 				Text: fileReferencePartToText(part),
 			})
-		case codersdk.ChatMessagePartTypeSkill:
-			// Skill parts from user input are converted to text
-			// so the LLM knows which skill the user requested.
-			result = append(result, fantasy.TextPart{
-				Text: skillPartToText(part),
-			})
 		case codersdk.ChatMessagePartTypeContextFile:
 			if part.ContextFileContent == "" {
 				continue
@@ -1088,49 +1088,6 @@ func TestFileReferencePreservation(t *testing.T) {
 	assert.Contains(t, textPart.Text, "func main() {}")
 }

-// TestSkillPartPreservation verifies skill parts survive the
-// storage round-trip and convert to text for LLMs.
-func TestSkillPartPreservation(t *testing.T) {
-	t.Parallel()
-
-	raw, err := chatprompt.MarshalParts([]codersdk.ChatMessagePart{{
-		Type:             codersdk.ChatMessagePartTypeSkill,
-		SkillName:        "deep-review",
-		SkillDescription: "Multi-reviewer code review",
-	}})
-	require.NoError(t, err)
-
-	// Storage round-trip: all fields intact.
-	parts, err := chatprompt.ParseContent(testMsg(codersdk.ChatMessageRoleUser, raw))
-	require.NoError(t, err)
-	require.Len(t, parts, 1)
-	assert.Equal(t, codersdk.ChatMessagePartTypeSkill, parts[0].Type)
-	assert.Equal(t, "deep-review", parts[0].SkillName)
-	assert.Equal(t, "Multi-reviewer code review", parts[0].SkillDescription)
-
-	// LLM dispatch: skill becomes a TextPart.
-	prompt, err := chatprompt.ConvertMessagesWithFiles(
-		context.Background(),
-		[]database.ChatMessage{{
-			Role:       database.ChatMessageRoleUser,
-			Visibility: database.ChatMessageVisibilityBoth,
-			Content:    raw,
-		}},
-		nil,
-		slogtest.Make(t, nil),
-	)
-	require.NoError(t, err)
-	require.Len(t, prompt, 1)
-	require.Len(t, prompt[0].Content, 1)
-
-	textPart, ok := fantasy.AsMessagePart[fantasy.TextPart](prompt[0].Content[0])
-	require.True(t, ok, "skill should become TextPart for LLM")
-	assert.Contains(t, textPart.Text, "deep-review")
-	assert.Contains(t, textPart.Text, "read_skill")
-	assert.Contains(t, textPart.Text, "Multi-reviewer code review")
-	assert.Contains(t, textPart.Text, "Multi-reviewer code review")
-}
-
 // TestAssistantWriteRoundTrip verifies the Stage 4 write path:
 // fantasy.Content (with ProviderMetadata) → PartFromContent →
 // MarshalParts → DB → ParseContent (SDK path) →
@@ -9,6 +9,7 @@ import (
 	"fmt"
 	"net/http"
 	"net/url"
+	"slices"
 	"strings"
 	"sync"
 	"time"
@@ -49,10 +50,11 @@ const connectTimeout = 10 * time.Second
 const toolCallTimeout = 60 * time.Second

 // ConnectAll connects to all configured MCP servers, discovers
-// their tools, and returns them as fantasy.AgentTool values. It
-// skips servers that fail to connect and logs warnings. The
-// returned cleanup function must be called to close all
-// connections.
+// their tools, and returns them as fantasy.AgentTool values.
+// Tools are sorted by their prefixed name so callers
+// receive a deterministic order. It skips servers that fail to
+// connect and logs warnings. The returned cleanup function
+// must be called to close all connections.
 func ConnectAll(
 	ctx context.Context,
 	logger slog.Logger,
@@ -108,7 +110,9 @@ func ConnectAll(
 			}

 			mu.Lock()
-			clients = append(clients, mcpClient)
+			if mcpClient != nil {
+				clients = append(clients, mcpClient)
+			}
 			tools = append(tools, serverTools...)
 			mu.Unlock()
 			return nil
@@ -119,6 +123,31 @@ func ConnectAll(
 	// discarded.
 	_ = eg.Wait()

+	// Sort tools by prefixed name for deterministic ordering
+	// regardless of goroutine completion order. Ties, possible
+	// when the __ separator produces ambiguous prefixed names,
+	// are broken by config ID. Stable prompt construction
+	// depends on consistent tool ordering.
+	slices.SortFunc(tools, func(a, b fantasy.AgentTool) int {
+		// All tools in this slice are mcpToolWrapper values
+		// created by connectOne above, so these checked
+		// assertions should always succeed. The config ID
+		// tiebreaker resolves the __ separator ambiguity
+		// documented at the top of this file.
+		aTool, ok := a.(MCPToolIdentifier)
+		if !ok {
+			panic(fmt.Sprintf("unexpected tool type %T", a))
+		}
+		bTool, ok := b.(MCPToolIdentifier)
+		if !ok {
+			panic(fmt.Sprintf("unexpected tool type %T", b))
+		}
+		return cmp.Or(
+			cmp.Compare(a.Info().Name, b.Info().Name),
+			cmp.Compare(aTool.MCPServerConfigID().String(), bTool.MCPServerConfigID().String()),
+		)
+	})
+
 	return tools, cleanup
 }

@@ -63,6 +63,17 @@ func greetTool() mcpserver.ServerTool {
 	}
 }

+// makeTool returns a ServerTool with the given name and a
+// no-op handler that always returns "ok".
+func makeTool(name string) mcpserver.ServerTool {
+	return mcpserver.ServerTool{
+		Tool: mcp.NewTool(name),
+		Handler: func(_ context.Context, _ mcp.CallToolRequest) (*mcp.CallToolResult, error) {
+			return mcp.NewToolResultText("ok"), nil
+		},
+	}
+}
+
 // makeConfig builds a database.MCPServerConfig suitable for tests.
 func makeConfig(slug, url string) database.MCPServerConfig {
 	return database.MCPServerConfig{
@@ -198,6 +209,121 @@ func TestConnectAll_MultipleServers(t *testing.T) {
 	assert.Contains(t, names, "beta__greet")
 }

+func TestConnectAll_NoToolsAfterFiltering(t *testing.T) {
+	t.Parallel()
+	ctx := context.Background()
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+
+	ts := newTestMCPServer(t, echoTool())
+
+	cfg := makeConfig("filtered", ts.URL)
+	cfg.ToolAllowList = []string{"greet"}
+
+	tools, cleanup := mcpclient.ConnectAll(
+		ctx,
+		logger,
+		[]database.MCPServerConfig{cfg},
+		nil,
+	)
+
+	require.Empty(t, tools)
+	assert.NotPanics(t, cleanup)
+}
+
+func TestConnectAll_DeterministicOrder(t *testing.T) {
+	t.Parallel()
+
+	t.Run("AcrossServers", func(t *testing.T) {
+		t.Parallel()
+		ctx := context.Background()
+		logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+
+		ts1 := newTestMCPServer(t, makeTool("zebra"))
+		ts2 := newTestMCPServer(t, makeTool("alpha"))
+		ts3 := newTestMCPServer(t, makeTool("middle"))
+
+		tools, cleanup := mcpclient.ConnectAll(
+			ctx,
+			logger,
+			[]database.MCPServerConfig{
+				makeConfig("srv3", ts3.URL),
+				makeConfig("srv1", ts1.URL),
+				makeConfig("srv2", ts2.URL),
+			},
+			nil,
+		)
+		t.Cleanup(cleanup)
+
+		require.Len(t, tools, 3)
+		// Sorted by full prefixed name (slug__tool), so slug
+		// order determines the sequence, not the tool name.
+		assert.Equal(t,
+			[]string{"srv1__zebra", "srv2__alpha", "srv3__middle"},
+			toolNames(tools),
+		)
+	})
+
+	t.Run("WithMultiToolServer", func(t *testing.T) {
+		t.Parallel()
+		ctx := context.Background()
+		logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+
+		multi := newTestMCPServer(t, makeTool("zeta"), makeTool("beta"))
+		other := newTestMCPServer(t, makeTool("gamma"))
+
+		tools, cleanup := mcpclient.ConnectAll(
+			ctx,
+			logger,
+			[]database.MCPServerConfig{
+				makeConfig("zzz", multi.URL),
+				makeConfig("aaa", other.URL),
+			},
+			nil,
+		)
+		t.Cleanup(cleanup)
+
+		require.Len(t, tools, 3)
+		assert.Equal(t,
+			[]string{"aaa__gamma", "zzz__beta", "zzz__zeta"},
+			toolNames(tools),
+		)
+	})
+
+	t.Run("TiebreakByConfigID", func(t *testing.T) {
+		t.Parallel()
+		ctx := context.Background()
+		logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+
+		ts1 := newTestMCPServer(t, makeTool("b__z"))
+		ts2 := newTestMCPServer(t, makeTool("z"))
+
+		// Use fixed UUIDs so the tiebreaker order is
+		// predictable. Both servers produce the same prefixed
+		// name, a__b__z, due to the __ separator ambiguity.
+		cfg1 := makeConfig("a", ts1.URL)
+		cfg1.ID = uuid.MustParse("00000000-0000-0000-0000-000000000002")
+
+		cfg2 := makeConfig("a__b", ts2.URL)
+		cfg2.ID = uuid.MustParse("00000000-0000-0000-0000-000000000001")
+
+		tools, cleanup := mcpclient.ConnectAll(
+			ctx,
+			logger,
+			[]database.MCPServerConfig{cfg1, cfg2},
+			nil,
+		)
+		t.Cleanup(cleanup)
+
+		require.Len(t, tools, 2)
+		assert.Equal(t, []string{"a__b__z", "a__b__z"}, toolNames(tools))
+
+		id0 := tools[0].(mcpclient.MCPToolIdentifier).MCPServerConfigID()
+		id1 := tools[1].(mcpclient.MCPToolIdentifier).MCPServerConfigID()
+		assert.Equal(t, cfg2.ID, id0, "lower config ID should sort first")
+		assert.Equal(t, cfg1.ID, id1, "higher config ID should sort second")
+	})
+}
+
 func TestConnectAll_AuthHeaders(t *testing.T) {
 	t.Parallel()
 	ctx := context.Background()
@@ -1055,12 +1055,17 @@ func TestAwaitSubagentCompletion(t *testing.T) {
 		require.NoError(t, err)
 		defer cancelProbe()

-		// Transition the child first, then publish once the
-		// durable completion state is observable. Pubsub only
-		// wakes the waiter; it does not guarantee the report is
-		// visible in the same instant as the notification.
-		setChatStatus(ctx, t, db, child.ID, database.ChatStatusWaiting, "")
+		// Insert the message BEFORE transitioning to Waiting.
+		// Stale PG LISTEN/NOTIFY notifications from the
+		// processor's earlier run can still be buffered in the
+		// pgListener after drainInflight returns. If such a
+		// notification is dispatched between setChatStatus and
+		// insertAssistantMessage, checkSubagentCompletion would
+		// see done=true (Waiting) with an empty report. By
+		// inserting the message first, the report is guaranteed
+		// to be committed before the status makes it visible.
 		insertAssistantMessage(ctx, t, db, child.ID, model.ID, "pubsub result")
+		setChatStatus(ctx, t, db, child.ID, database.ChatStatusWaiting, "")
 		require.EventuallyWithT(t, func(c *assert.CollectT) {
 			chat, report, done, err := server.checkSubagentCompletion(ctx, child.ID)
 			require.NoError(c, err)
@@ -1,6 +1,7 @@
 package chatd_test

 import (
+	"strings"
 	"testing"

 	"github.com/google/uuid"
@@ -110,19 +111,19 @@ func TestSpawnComputerUseAgent_SystemPromptFormat(t *testing.T) {

 	// The system message raw content is a JSON-encoded string.
 	// It should contain the system prompt with the user prompt.
-	var rawSystemContent string
+	var foundPrompt bool
 	for _, msg := range messages {
 		if msg.Role != "system" {
 			continue
 		}
-		if msg.Content.Valid {
-			rawSystemContent = string(msg.Content.RawMessage)
+		if msg.Content.Valid && strings.Contains(string(msg.Content.RawMessage), prompt) {
+			foundPrompt = true
 			break
 		}
 	}

-	assert.Contains(t, rawSystemContent, prompt,
-		"system prompt raw content should contain the user prompt")
+	assert.True(t, foundPrompt,
+		"at least one system message should contain the user prompt")
 }

 func TestSpawnComputerUseAgent_ChildIsListedUnderParent(t *testing.T) {
@@ -212,6 +212,7 @@ type AuditLogsRequest struct {
 type AuditLogResponse struct {
 	AuditLogs []AuditLog `json:"audit_logs"`
 	Count     int64      `json:"count"`
+	CountCap  int64      `json:"count_cap"`
 }

 type CreateTestAuditLogRequest struct {
@@ -26,6 +26,12 @@ import (
 // threshold settings.
 const ChatCompactionThresholdKeyPrefix = "chat_compaction_threshold_pct:"

+// MaxChatFileIDs is the maximum number of file IDs that can be
+// associated with a single chat. This limit prevents unbounded
+// growth in the chat_file_links table. It is easier to raise
+// this limit than to lower it.
+const MaxChatFileIDs = 20
+
 // CompactionThresholdKey returns the user-config key for a specific
 // model configuration's compaction threshold.
 func CompactionThresholdKey(modelConfigID uuid.UUID) string {
@@ -46,24 +52,25 @@ const (

 // Chat represents a chat session with an AI agent.
 type Chat struct {
-	ID                uuid.UUID         `json:"id" format:"uuid"`
-	OwnerID           uuid.UUID         `json:"owner_id" format:"uuid"`
-	WorkspaceID       *uuid.UUID        `json:"workspace_id,omitempty" format:"uuid"`
-	BuildID           *uuid.UUID        `json:"build_id,omitempty" format:"uuid"`
-	AgentID           *uuid.UUID        `json:"agent_id,omitempty" format:"uuid"`
-	ParentChatID      *uuid.UUID        `json:"parent_chat_id,omitempty" format:"uuid"`
-	RootChatID        *uuid.UUID        `json:"root_chat_id,omitempty" format:"uuid"`
-	LastModelConfigID uuid.UUID         `json:"last_model_config_id" format:"uuid"`
-	Title             string            `json:"title"`
-	Status            ChatStatus        `json:"status"`
-	LastError         *string           `json:"last_error"`
-	DiffStatus        *ChatDiffStatus   `json:"diff_status,omitempty"`
-	CreatedAt         time.Time         `json:"created_at" format:"date-time"`
-	UpdatedAt         time.Time         `json:"updated_at" format:"date-time"`
-	Archived          bool              `json:"archived"`
-	PinOrder          int32             `json:"pin_order"`
-	MCPServerIDs      []uuid.UUID       `json:"mcp_server_ids" format:"uuid"`
-	Labels            map[string]string `json:"labels"`
+	ID                uuid.UUID          `json:"id" format:"uuid"`
+	OwnerID           uuid.UUID          `json:"owner_id" format:"uuid"`
+	WorkspaceID       *uuid.UUID         `json:"workspace_id,omitempty" format:"uuid"`
+	BuildID           *uuid.UUID         `json:"build_id,omitempty" format:"uuid"`
+	AgentID           *uuid.UUID         `json:"agent_id,omitempty" format:"uuid"`
+	ParentChatID      *uuid.UUID         `json:"parent_chat_id,omitempty" format:"uuid"`
+	RootChatID        *uuid.UUID         `json:"root_chat_id,omitempty" format:"uuid"`
+	LastModelConfigID uuid.UUID          `json:"last_model_config_id" format:"uuid"`
+	Title             string             `json:"title"`
+	Status            ChatStatus         `json:"status"`
+	LastError         *string            `json:"last_error"`
+	DiffStatus        *ChatDiffStatus    `json:"diff_status,omitempty"`
+	CreatedAt         time.Time          `json:"created_at" format:"date-time"`
+	UpdatedAt         time.Time          `json:"updated_at" format:"date-time"`
+	Archived          bool               `json:"archived"`
+	PinOrder          int32              `json:"pin_order"`
+	MCPServerIDs      []uuid.UUID        `json:"mcp_server_ids" format:"uuid"`
+	Labels            map[string]string  `json:"labels"`
+	Files             []ChatFileMetadata `json:"files,omitempty"`
 	// HasUnread is true when assistant messages exist beyond
 	// the owner's read cursor, which updates on stream
 	// connect and disconnect.
@@ -73,6 +80,18 @@ type Chat struct {
 	// is updated only when context changes — first workspace
 	// attach or agent change.
 	LastInjectedContext []ChatMessagePart `json:"last_injected_context,omitempty"`
+	Warnings            []string          `json:"warnings,omitempty"`
+}
+
+// ChatFileMetadata contains lightweight metadata about a file
+// associated with a chat, excluding the file content itself.
+type ChatFileMetadata struct {
+	ID             uuid.UUID `json:"id" format:"uuid"`
+	OwnerID        uuid.UUID `json:"owner_id" format:"uuid"`
+	OrganizationID uuid.UUID `json:"organization_id" format:"uuid"`
+	Name           string    `json:"name"`
+	MimeType       string    `json:"mime_type"`
+	CreatedAt      time.Time `json:"created_at" format:"date-time"`
 }

 // ChatMessage represents a single message in a chat.
@@ -326,7 +345,6 @@ const (
 	ChatInputPartTypeText          ChatInputPartType = "text"
 	ChatInputPartTypeFile          ChatInputPartType = "file"
 	ChatInputPartTypeFileReference ChatInputPartType = "file-reference"
-	ChatInputPartTypeSkill         ChatInputPartType = "skill"
 )

 // ChatInputPart is a single user input part for creating a chat.
@@ -341,15 +359,12 @@ type ChatInputPart struct {
 	EndLine   int    `json:"end_line,omitempty"`
 	// The code content from the diff that was commented on.
 	Content string `json:"content,omitempty"`
-	// The following fields are only set when Type is
-	// ChatInputPartTypeSkill.
-	SkillName        string `json:"skill_name,omitempty"`
-	SkillDescription string `json:"skill_description,omitempty"`
 }

 // CreateChatRequest is the request to create a new chat.
 type CreateChatRequest struct {
 	Content       []ChatInputPart   `json:"content"`
+	SystemPrompt  string            `json:"system_prompt,omitempty"`
 	WorkspaceID   *uuid.UUID        `json:"workspace_id,omitempty" format:"uuid"`
 	ModelConfigID *uuid.UUID        `json:"model_config_id,omitempty" format:"uuid"`
 	MCPServerIDs  []uuid.UUID       `json:"mcp_server_ids,omitempty" format:"uuid"`
@@ -373,11 +388,27 @@ type UpdateChatRequest struct {
 	Labels   *map[string]string `json:"labels,omitempty"`
 }

+// ChatBusyBehavior controls what happens when a user sends a message
+// while the chat is already processing.
+type ChatBusyBehavior string
+
+const (
+	// ChatBusyBehaviorQueue queues the message for processing after
+	// the current run finishes.
+	ChatBusyBehaviorQueue ChatBusyBehavior = "queue"
+	// ChatBusyBehaviorInterrupt queues the message and interrupts
+	// the active run. The partial assistant response is persisted
+	// before the queued message is promoted, preserving correct
+	// conversation order.
+	ChatBusyBehaviorInterrupt ChatBusyBehavior = "interrupt"
+)
+
 // CreateChatMessageRequest is the request to add a message to a chat.
 type CreateChatMessageRequest struct {
-	Content       []ChatInputPart `json:"content"`
-	ModelConfigID *uuid.UUID      `json:"model_config_id,omitempty" format:"uuid"`
-	MCPServerIDs  *[]uuid.UUID    `json:"mcp_server_ids,omitempty" format:"uuid"`
+	Content       []ChatInputPart  `json:"content"`
+	ModelConfigID *uuid.UUID       `json:"model_config_id,omitempty" format:"uuid"`
+	MCPServerIDs  *[]uuid.UUID     `json:"mcp_server_ids,omitempty" format:"uuid"`
+	BusyBehavior  ChatBusyBehavior `json:"busy_behavior,omitempty" enums:"queue,interrupt"`
 }

 // EditChatMessageRequest is the request to edit a user message in a chat.
@@ -390,6 +421,15 @@ type CreateChatMessageResponse struct {
 	Message       *ChatMessage       `json:"message,omitempty"`
 	QueuedMessage *ChatQueuedMessage `json:"queued_message,omitempty"`
 	Queued        bool               `json:"queued"`
+	Warnings      []string           `json:"warnings,omitempty"`
+}
+
+// EditChatMessageResponse is the response from editing a message in a chat.
+// Edits are always synchronous (no queueing), so the message is returned
+// directly.
+type EditChatMessageResponse struct {
+	Message  ChatMessage `json:"message"`
+	Warnings []string    `json:"warnings,omitempty"`
 }

 // UploadChatFileResponse is the response from uploading a chat file.
@@ -631,7 +671,7 @@ type ChatModelOpenAIProviderOptions struct {
 	ParallelToolCalls   *bool            `json:"parallel_tool_calls,omitempty" description:"Whether the model may make multiple tool calls in parallel"`
 	User                *string          `json:"user,omitempty" description:"Unique identifier for the end user for abuse monitoring" hidden:"true"`
 	ReasoningEffort     *string          `json:"reasoning_effort,omitempty" description:"Controls the level of reasoning effort" enum:"none,minimal,low,medium,high,xhigh"`
-	ReasoningSummary    *string          `json:"reasoning_summary,omitempty" description:"Controls whether reasoning tokens are summarized in the response"`
+	ReasoningSummary    *string          `json:"reasoning_summary,omitempty" description:"Controls whether reasoning tokens are summarized in the response" enum:"auto,concise,detailed"`
 	MaxCompletionTokens *int64           `json:"max_completion_tokens,omitempty" description:"Upper bound on tokens the model may generate"`
 	TextVerbosity       *string          `json:"text_verbosity,omitempty" description:"Controls the verbosity of the text response" enum:"low,medium,high"`
 	Prediction          map[string]any   `json:"prediction,omitempty" description:"Predicted output content to speed up responses" hidden:"true"`
@@ -639,12 +679,12 @@ type ChatModelOpenAIProviderOptions struct {
 	Metadata            map[string]any   `json:"metadata,omitempty" description:"Arbitrary metadata to attach to the request" hidden:"true"`
 	PromptCacheKey      *string          `json:"prompt_cache_key,omitempty" description:"Key for enabling cross-request prompt caching"`
 	SafetyIdentifier    *string          `json:"safety_identifier,omitempty" description:"Developer-specific safety identifier for the request" hidden:"true"`
-	ServiceTier         *string          `json:"service_tier,omitempty" description:"Latency tier to use for processing the request"`
+	ServiceTier         *string          `json:"service_tier,omitempty" description:"Latency tier to use for processing the request" enum:"auto,default,flex,scale,priority"`
 	StructuredOutputs   *bool            `json:"structured_outputs,omitempty" description:"Whether to enable structured JSON output mode" hidden:"true"`
 	StrictJSONSchema    *bool            `json:"strict_json_schema,omitempty" description:"Whether to enforce strict adherence to the JSON schema" hidden:"true"`
 	WebSearchEnabled    *bool            `json:"web_search_enabled,omitempty" description:"Enable OpenAI web search tool for grounding responses with real-time information"`
 	SearchContextSize   *string          `json:"search_context_size,omitempty" description:"Amount of search context to use" enum:"low,medium,high"`
-	AllowedDomains      []string         `json:"allowed_domains,omitempty" description:"Restrict web search to these domains"`
+	AllowedDomains      []string         `json:"allowed_domains,omitempty" label:"Web Search: Allowed Domains" description:"Restrict web search to these domains"`
 }

 // ChatModelAnthropicThinkingOptions configures Anthropic thinking budget.
@@ -656,11 +696,11 @@ type ChatModelAnthropicThinkingOptions struct {
 type ChatModelAnthropicProviderOptions struct {
 	SendReasoning          *bool                              `json:"send_reasoning,omitempty" description:"Whether to include reasoning content in the response"`
 	Thinking               *ChatModelAnthropicThinkingOptions `json:"thinking,omitempty" description:"Configuration for extended thinking"`
-	Effort                 *string                            `json:"effort,omitempty" description:"Controls the level of reasoning effort" enum:"low,medium,high,max"`
+	Effort                 *string                            `json:"effort,omitempty" label:"Reasoning Effort" description:"Controls the level of reasoning effort" enum:"low,medium,high,max"`
 	DisableParallelToolUse *bool                              `json:"disable_parallel_tool_use,omitempty" description:"Whether to disable parallel tool execution"`
 	WebSearchEnabled       *bool                              `json:"web_search_enabled,omitempty" description:"Enable Anthropic web search tool for grounding responses with real-time information"`
-	AllowedDomains         []string                           `json:"allowed_domains,omitempty" description:"Restrict web search to these domains (cannot be used with blocked_domains)"`
-	BlockedDomains         []string                           `json:"blocked_domains,omitempty" description:"Block web search on these domains (cannot be used with allowed_domains)"`
+	AllowedDomains         []string                           `json:"allowed_domains,omitempty" label:"Web Search: Allowed Domains" description:"Restrict web search to these domains (cannot be used with blocked_domains)"`
+	BlockedDomains         []string                           `json:"blocked_domains,omitempty" label:"Web Search: Blocked Domains" description:"Block web search on these domains (cannot be used with allowed_domains)"`
 }

 // ChatModelGoogleThinkingConfig configures Google thinking behavior.
@@ -979,6 +1019,7 @@ type ChatCostSummary struct {
 	TotalOutputTokens        int64                    `json:"total_output_tokens"`
 	TotalCacheReadTokens     int64                    `json:"total_cache_read_tokens"`
 	TotalCacheCreationTokens int64                    `json:"total_cache_creation_tokens"`
+	TotalRuntimeMs           int64                    `json:"total_runtime_ms"`
 	ByModel                  []ChatCostModelBreakdown `json:"by_model"`
 	ByChat                   []ChatCostChatBreakdown  `json:"by_chat"`
 	UsageLimit               *ChatUsageLimitStatus    `json:"usage_limit,omitempty"`
@@ -996,6 +1037,7 @@ type ChatCostModelBreakdown struct {
 	TotalOutputTokens        int64     `json:"total_output_tokens"`
 	TotalCacheReadTokens     int64     `json:"total_cache_read_tokens"`
 	TotalCacheCreationTokens int64     `json:"total_cache_creation_tokens"`
+	TotalRuntimeMs           int64     `json:"total_runtime_ms"`
 }

 // ChatCostChatBreakdown contains per-root-chat cost aggregation.
@@ -1008,6 +1050,7 @@ type ChatCostChatBreakdown struct {
 	TotalOutputTokens        int64     `json:"total_output_tokens"`
 	TotalCacheReadTokens     int64     `json:"total_cache_read_tokens"`
 	TotalCacheCreationTokens int64     `json:"total_cache_creation_tokens"`
+	TotalRuntimeMs           int64     `json:"total_runtime_ms"`
 }

 // ChatCostUserRollup contains per-user cost aggregation for admin views.
@@ -1023,6 +1066,7 @@ type ChatCostUserRollup struct {
 	TotalOutputTokens        int64     `json:"total_output_tokens"`
 	TotalCacheReadTokens     int64     `json:"total_cache_read_tokens"`
 	TotalCacheCreationTokens int64     `json:"total_cache_creation_tokens"`
+	TotalRuntimeMs           int64     `json:"total_runtime_ms"`
 }

 // ChatCostUsersResponse is the response from the admin chat cost users endpoint.
@@ -1940,7 +1984,7 @@ func (c *ExperimentalClient) EditChatMessage(
 	chatID uuid.UUID,
 	messageID int64,
 	req EditChatMessageRequest,
-) (ChatMessage, error) {
+) (EditChatMessageResponse, error) {
 	res, err := c.Request(
 		ctx,
 		http.MethodPatch,
@@ -1948,14 +1992,14 @@ func (c *ExperimentalClient) EditChatMessage(
 		req,
 	)
 	if err != nil {
-		return ChatMessage{}, err
+		return EditChatMessageResponse{}, err
 	}
 	if res.StatusCode != http.StatusOK {
-		return ChatMessage{}, readBodyAsChatUsageLimitError(res)
+		return EditChatMessageResponse{}, readBodyAsChatUsageLimitError(res)
 	}
 	defer res.Body.Close()
-	var message ChatMessage
-	return message, json.NewDecoder(res.Body).Decode(&message)
+	var resp EditChatMessageResponse
+	return resp, json.NewDecoder(res.Body).Decode(&resp)
 }

 // InterruptChat cancels an in-flight chat run and leaves it waiting.
@@ -96,6 +96,7 @@ type ConnectionLogsRequest struct {
 type ConnectionLogResponse struct {
 	ConnectionLogs []ConnectionLog `json:"connection_logs"`
 	Count          int64           `json:"count"`
+	CountCap       int64           `json:"count_cap"`
 }

 func (c *Client) ConnectionLogs(ctx context.Context, req ConnectionLogsRequest) (ConnectionLogResponse, error) {
@@ -7,6 +7,14 @@ features, you can [request a trial](https://coder.com/trial) or

 ![Licenses screen shows license information and seat consumption](../../images/admin/licenses/licenses-screen.png)

+## Offline license validation
+
+Coder license keys are signed JWTs that are validated locally using cryptographic
+signatures. No outbound connection to Coder's servers is required for license
+validation. This means licenses work in
+[air-gapped and offline deployments](../../install/airgap.md) without any
+additional configuration.
+
 ## Adding your license key

 There are two ways to add a license to a Coder deployment:
@@ -134,6 +134,12 @@ edited message onward, truncating any messages that followed it.
 |-----------|-------------------|----------|----------------------------------|
 | `content` | `ChatInputPart[]` | yes      | The replacement message content. |

+The response is an `EditChatMessageResponse` with the edited `message`
+and an optional `warnings` array. When file references in the edited
+content cannot be linked (e.g. the per-chat file cap is reached), the
+edit still succeeds and the `warnings` array describes which files
+were not linked.
+
 ### Stream updates

 `GET /api/experimental/chats/{chat}/stream`
@@ -201,7 +207,9 @@ Each event is a JSON object with `kind` and `chat` fields:

 `GET /api/experimental/chats`

-Returns all chats owned by the authenticated user.
+Returns all chats owned by the authenticated user. The `files` field is
+populated on `POST /chats` and `GET /chats/{id}`. Other endpoints that
+return a `Chat` object omit it.

 | Query parameter | Type     | Required | Description                                                      |
 |-----------------|----------|----------|------------------------------------------------------------------|
@@ -212,7 +220,17 @@ Returns all chats owned by the authenticated user.

 `GET /api/experimental/chats/{chat}`

-Returns the `Chat` object (metadata only, no messages).
+Returns the `Chat` object (metadata only, no messages). The response
+includes a `files` field (`ChatFileMetadata[]`) containing metadata for
+files that have been successfully linked to the chat. File linking is
+best-effort; if linking fails, the file remains in message content but
+will be absent from this field.
+
+When file linking is skipped (e.g. the per-chat file cap is reached),
+`POST /chats` includes a `warnings` array on the `Chat` response and
+`POST /chats/{chat}/messages` includes a `warnings` array on the
+`CreateChatMessageResponse`. The `warnings` field is `omitempty` and
+absent when all files are linked successfully.

 ### Get chat messages

@@ -295,6 +313,10 @@ file, use `GET /api/experimental/chats/files/{file}`.
 Supported formats: PNG, JPEG, GIF, WebP (up to 10 MB). The server
 validates actual file content regardless of the declared `Content-Type`.

+Files referenced in messages are automatically linked to the chat and
+appear in the `files` field on subsequent
+`GET /api/experimental/chats/{chat}` responses.
+
 ## Chat statuses

 | Status      | Meaning                                                      |
@@ -13,6 +13,7 @@ air-gapped with Kubernetes or Docker.
 | PostgreSQL                | If no [PostgreSQL connection URL](../reference/cli/server.md#--postgres-url) is specified, Coder will download Postgres from [repo1.maven.org](https://repo1.maven.org)                                                                                            | An external database is required, you must specify a [PostgreSQL connection URL](../reference/cli/server.md#--postgres-url)                                                                                                                                                                          |
 | Telemetry                 | Telemetry is on by default, and [can be disabled](../reference/cli/server.md#--telemetry)                                                                                                                                                                          | Telemetry [can be disabled](../reference/cli/server.md#--telemetry)                                                                                                                                                                                                                                  |
 | Update check              | By default, Coder checks for updates from [GitHub releases](https://github.com/coder/coder/releases)                                                                                                                                                               | Update checks [can be disabled](../reference/cli/server.md#--update-check)                                                                                                                                                                                                                           |
+| License validation        | License keys are validated locally using cryptographic signatures. No outbound connection to Coder is required                                                                                                                                                     | No changes needed. See [offline license validation](../admin/licensing/index.md#offline-license-validation)                                                                                                                                                                                          |
 | AI Governance Usage Count | By default, deployments with the [AI Governance Add On](../ai-coder/ai-governance.md) report usage data                                                                                                                                                            | [Contact us](https://coder.com/contact) to request a license with usage reporting off.                                                                                                                                                                                                               |

 ## Air-gapped container images
@@ -1299,6 +1299,12 @@
 					"description": "Custom claims/scopes with Okta for group/role sync",
 					"path": "./tutorials/configuring-okta.md"
 				},
+				{
+					"title": "Persistent Shared Workspaces",
+					"description": "Set up long-lived shared workspaces with service accounts and workspace sharing",
+					"path": "./tutorials/persistent-shared-workspaces.md",
+					"state": ["premium"]
+				},
 				{
 					"title": "Google to AWS Federation",
 					"description": "Federating a Google Cloud service account to AWS",
@@ -90,7 +90,8 @@ curl -X GET http://coder-server:8080/api/v2/audit?limit=0 \
      "user_agent": "string"
    }
  ],
-  "count": 0
+  "count": 0,
+  "count_cap": 0
 }
 ```

@@ -291,7 +291,8 @@ curl -X GET http://coder-server:8080/api/v2/connectionlog?limit=0 \
      "workspace_owner_username": "string"
    }
  ],
-  "count": 0
+  "count": 0,
+  "count_cap": 0
 }
 ```

@@ -1740,7 +1740,8 @@
      "user_agent": "string"
    }
  ],
-  "count": 0
+  "count": 0,
+  "count_cap": 0
 }
 ```

@@ -1750,6 +1751,7 @@
 |--------------|-------------------------------------------------|----------|--------------|-------------|
 | `audit_logs` | array of [codersdk.AuditLog](#codersdkauditlog) | false    |              |             |
 | `count`      | integer                                         | false    |              |             |
+| `count_cap`  | integer                                         | false    |              |             |

 ## codersdk.AuthMethod

@@ -2173,7 +2175,8 @@ AuthorizationObject can represent a "set" of objects, such as: all workspaces in
      "workspace_owner_username": "string"
    }
  ],
-  "count": 0
+  "count": 0,
+  "count_cap": 0
 }
 ```

@@ -2183,6 +2186,7 @@ AuthorizationObject can represent a "set" of objects, such as: all workspaces in
 |-------------------|-----------------------------------------------------------|----------|--------------|-------------|
 | `connection_logs` | array of [codersdk.ConnectionLog](#codersdkconnectionlog) | false    |              |             |
 | `count`           | integer                                                   | false    |              |             |
+| `count_cap`       | integer                                                   | false    |              |             |

 ## codersdk.ConnectionLogSSHInfo

@@ -0,0 +1,258 @@
+# Persistent Shared Workspaces with Service Accounts
+
+> [!NOTE]
+> This guide requires a
+> [Premium license](https://coder.com/pricing#compare-plans) because service
+> accounts are a Premium feature. For more details,
+> [contact your account team](https://coder.com/contact).
+
+This guide walks through setting up a long-lived workspace that is owned by a
+service account and shared with a rotating set of users. Because no single
+person owns the workspace, it persists across team changes and every user
+authenticates as themselves.
+
+This pattern is useful for any scenario where a workspace outlives the people
+who use it:
+
+- **On-call rotations** — Engineers share a workspace pre-loaded with runbooks,
+  dashboards, and monitoring tools. Access rotates with the shift schedule.
+- **Shared staging or QA** — A team workspace hosts a persistent staging
+  environment. Testers and reviewers are added and removed as sprints change.
+- **Pair programming** — A service-account-owned workspace gives two or more
+  developers a shared environment without either one owning (and accidentally
+  deleting) it.
+- **Contractor onboarding** — An external team gets scoped access to a workspace
+  for the duration of an engagement, then access is revoked.
+
+The steps below use an **on-call SRE workspace** as a running example, but the
+same commands apply to any of the scenarios above. Substitute the usernames,
+group names, and template to match your use case.
+
+## Prerequisites
+
+- A running Coder deployment (v2.32+) with workspace sharing enabled. Sharing
+  is on by default for OSS; Premium deployments may require
+  [admin configuration](../user-guides/shared-workspaces.md#policies).
+- The [Coder CLI](../install/index.md) installed and authenticated.
+- An account with the `Owner` or `User Admin` role.
+- [OIDC authentication](../admin/users/oidc-auth/index.md) configured so
+  shared users log in with their corporate SSO identity. Configure
+  [refresh tokens](../admin/users/oidc-auth/refresh-tokens.md) to prevent
+  session timeouts during long work sessions.
+- A [wildcard access URL](../admin/networking/wildcard-access-url.md) configured
+  (e.g. `*.coder.example.com`) so that shared users can access workspace apps
+  without a 404.
+- (Recommended) [IdP Group Sync](../admin/users/idp-sync.md#group-sync)
+  configured if your identity provider manages group membership for the teams
+  that will share the workspace.
+
+## 1. Create a service account
+
+Create a dedicated service account that will own the shared workspace. Service
+accounts are non-human accounts intended for automation and shared ownership.
+Because no individual user owns the workspace, there are no personal
+credentials to expose and the shared environment is not affected when any user
+leaves the team or the organization.
+
+```shell
+# On-call example — substitute a name that fits your use case
+coder users create \
+  --username oncall-sre \
+  --service-account
+```
+
+## 2. Generate an API token for the service account
+
+Generate a long-lived API token so you can create and manage workspaces on
+behalf of the service account:
+
+```shell
+coder tokens create \
+  --user oncall-sre \
+  --name oncall-automation \
+  --lifetime 8760h
+```
+
+Store this token securely (e.g. in a secrets manager like Vault or AWS Secrets
+Manager).
+
+> [!IMPORTANT]
+> Never distribute this token to end users. The token is for workspace
+> administration only. Shared users authenticate as themselves and reach the
+> workspace through sharing.
+
+## 3. Create the workspace
+
+Authenticate as the service account and create the workspace:
+
+```shell
+export CODER_SESSION_TOKEN="<token-from-step-2>"
+
+coder create oncall-sre/oncall-workspace \
+  --template your-oncall-template \
+  --use-parameter-defaults \
+  --yes
+```
+
+> [!TIP]
+> Design a dedicated template for the workspace with the tools your team
+> needs pre-installed (e.g. monitoring dashboards for on-call, test runners
+> for QA). Set `subdomain = true` on workspace apps so that shared users can
+> access web-based tools without a 404. See
+> [Accessing workspace apps in shared workspaces](../user-guides/shared-workspaces.md#accessing-workspace-apps-in-shared-workspaces).
+
+## 4. Share the workspace
+
+Use `coder sharing share` to grant access to users who need the workspace:
+
+```shell
+coder sharing share oncall-sre/oncall-workspace --user alice
+```
+
+This gives `alice` the default `use` role, which allows connection via SSH and
+workspace apps, starting and stopping the workspace, and viewing logs and stats.
+
+To grant `admin` permissions (which includes all `use` permissions as well as renaming, updating, and inviting
+others to join with the `use` role):
+
+```shell
+coder sharing share oncall-sre/oncall-workspace --user alice:admin
+```
+
+To share with multiple users at once:
+
+```shell
+coder sharing share oncall-sre/oncall-workspace --user alice:admin,bob
+```
+
+To share with an entire Coder group:
+
+```shell
+coder sharing share oncall-sre/oncall-workspace --group sre-oncall
+```
+
+> [!NOTE]
+> Groups can be synced from your identity provider using
+> [IdP Sync](../admin/users/idp-sync.md#group-sync). If your IdP already
+> manages team membership, sharing with a group is the simplest approach.
+
+## 5. Rotate access
+
+When team membership changes, remove outgoing users and add incoming ones:
+
+```shell
+# Remove outgoing user
+coder sharing remove oncall-sre/oncall-workspace --user alice
+
+# Add incoming user
+coder sharing share oncall-sre/oncall-workspace --user carol
+```
+
+> [!IMPORTANT]
+> The workspace must be restarted for user removal to take effect.
+
+Verify current sharing status at any time:
+
+```shell
+coder sharing status oncall-sre/oncall-workspace
+```
+
+## 6. Automate access changes (optional)
+
+For use cases with frequent rotation (such as on-call shifts), you can integrate
+the share/remove commands into external tooling like PagerDuty, Opsgenie, or a
+cron job.
+
+### Rotation script
+
+```shell
+#!/bin/bash
+# rotate-access.sh
+# Usage: ./rotate-access.sh <outgoing-user> <incoming-user>
+
+WORKSPACE="oncall-sre/oncall-workspace"
+OUTGOING="$1"
+INCOMING="$2"
+
+if [ -n "$OUTGOING" ]; then
+  echo "Removing access for $OUTGOING..."
+  coder sharing remove "$WORKSPACE" --user "$OUTGOING"
+fi
+
+echo "Granting access to $INCOMING..."
+coder sharing share "$WORKSPACE" --user "$INCOMING"
+
+echo "Restarting workspace to apply changes..."
+coder restart "$WORKSPACE" --yes
+
+echo "Current sharing status:"
+coder sharing status "$WORKSPACE"
+```
+
+### Group-based rotation with IdP Sync
+
+If your identity provider manages group membership (e.g. an `sre-oncall` group
+in Okta or Azure AD), you can skip manual share/remove commands entirely:
+
+1. Configure [Group Sync](../admin/users/idp-sync.md#group-sync) to
+   synchronize the group from your IdP to Coder.
+
+1. Share the workspace with the group once:
+
+   ```shell
+   coder sharing share oncall-sre/oncall-workspace --group sre-oncall
+   ```
+
+1. When your IdP rotates group membership, Coder group membership updates on
+   next login. All current members have access; removed members lose access
+   after a workspace restart.
+
+## Finding shared workspaces
+
+Shared users can find workspaces shared with them:
+
+```shell
+# List all workspaces shared with you
+coder list --search shared:true
+
+# List workspaces shared with a specific user
+coder list --search shared_with_user:alice
+
+# List workspaces shared with a specific group
+coder list --search shared_with_group:sre-oncall
+```
+
+## Troubleshooting
+
+### Shared user sees 404 on workspace apps
+
+Workspace apps using path-based routing block non-owners by default. Configure a
+[wildcard access URL](../admin/networking/wildcard-access-url.md) and set
+`subdomain = true` on the workspace app in your template.
+
+### Removed user still has access
+
+Access removal requires a workspace restart. Run
+`coder restart <workspace>` after removing a user or group.
+
+### Group sync not updating membership
+
+Group membership changes in your IdP are not reflected until the user logs out
+and back in. Group sync runs at login time, not on a polling schedule. Check the
+Coder server logs with
+`CODER_LOG_FILTER=".*userauth.*|.*groups returned.*"` for details. See
+[Troubleshooting group sync](../admin/users/idp-sync.md#troubleshooting-grouproleorganization-sync)
+for more information.
+
+## Next steps
+
+- [Shared Workspaces](../user-guides/shared-workspaces.md) — full reference
+  for workspace sharing features and UI
+- [IdP Sync](../admin/users/idp-sync.md) — group, role, and organization
+  sync configuration
+- [Configuring Okta](./configuring-okta.md) — Okta-specific OIDC setup with
+  custom claims and scopes
+- [Security Best Practices](./best-practices/security-best-practices.md) —
+  deployment-wide security hardening
+- [Sessions and Tokens](../admin/users/sessions-tokens.md) — API token
+  management and scoping
@@ -5,7 +5,7 @@ terraform {
    }
    docker = {
      source  = "kreuzwerker/docker"
-      version = "~> 3.0"
+      version = "~> 4.0"
    }
    envbuilder = {
      source = "coder/envbuilder"
@@ -1,5 +1,5 @@
 # 1.93.1
-FROM rust:slim@sha256:1d0000a49fb62f4fde24455f49d59c6c088af46202d65d8f455b722f7263e8f8 AS rust-utils
+FROM rust:slim@sha256:a08d20a404f947ed358dfb63d1ee7e0b88ecad3c45ba9682ccbf2cb09c98acca AS rust-utils
 # Install rust helper programs
 ENV CARGO_INSTALL_ROOT=/tmp/
 # Use more reliable mirrors for Debian packages
@@ -8,7 +8,7 @@ RUN sed -i 's|http://deb.debian.org/debian|http://mirrors.edge.kernel.org/debian
 RUN apt-get update && apt-get install -y libssl-dev openssl pkg-config build-essential
 RUN cargo install jj-cli typos-cli watchexec-cli

-FROM ubuntu:jammy@sha256:5e5b128eb4ff35ee52687c20d081dcc15b8cb55e113247683f435224fc58b956 AS go
+FROM ubuntu:jammy@sha256:eb29ed27b0821dca09c2e28b39135e185fc1302036427d5f4d70a41ce8fd7659 AS go

 # Install Go manually, so that we can control the version
 ARG GO_VERSION=1.25.8
@@ -83,7 +83,7 @@ RUN curl -L -o protoc.zip https://github.com/protocolbuffers/protobuf/releases/d
 	unzip protoc.zip && \
 	rm protoc.zip

-FROM ubuntu:jammy@sha256:5e5b128eb4ff35ee52687c20d081dcc15b8cb55e113247683f435224fc58b956
+FROM ubuntu:jammy@sha256:eb29ed27b0821dca09c2e28b39135e185fc1302036427d5f4d70a41ce8fd7659

 SHELL ["/bin/bash", "-c"]

@@ -6,7 +6,7 @@ terraform {
    }
    docker = {
      source  = "kreuzwerker/docker"
-      version = "~> 3.6"
+      version = "~> 4.0"
    }
  }
 }
@@ -922,7 +922,7 @@ resource "coder_script" "boundary_config_setup" {
 module "claude-code" {
  count               = data.coder_task.me.enabled ? data.coder_workspace.me.start_count : 0
  source              = "dev.registry.coder.com/coder/claude-code/coder"
-  version             = "4.8.2"
+  version             = "4.9.1"
  enable_boundary     = true
  agent_id            = coder_agent.dev.id
  workdir             = local.repo_dir
@@ -16,6 +16,9 @@ import (
 	"github.com/coder/coder/v2/codersdk"
 )

+// NOTE: See the auditLogCountCap note.
+const connectionLogCountCap = 2000
+
 // @Summary Get connection logs
 // @ID get-connection-logs
 // @Security CoderSessionToken
@@ -49,6 +52,7 @@ func (api *API) connectionLogs(rw http.ResponseWriter, r *http.Request) {
 	// #nosec G115 - Safe conversion as pagination limit is expected to be within int32 range
 	filter.LimitOpt = int32(page.Limit)

+	countFilter.CountCap = connectionLogCountCap
 	count, err := api.Database.CountConnectionLogs(ctx, countFilter)
 	if dbauthz.IsNotAuthorizedError(err) {
 		httpapi.Forbidden(rw)
@@ -63,6 +67,7 @@ func (api *API) connectionLogs(rw http.ResponseWriter, r *http.Request) {
 		httpapi.Write(ctx, rw, http.StatusOK, codersdk.ConnectionLogResponse{
 			ConnectionLogs: []codersdk.ConnectionLog{},
 			Count:          0,
+			CountCap:       connectionLogCountCap,
 		})
 		return
 	}
@@ -80,6 +85,7 @@ func (api *API) connectionLogs(rw http.ResponseWriter, r *http.Request) {
 	httpapi.Write(ctx, rw, http.StatusOK, codersdk.ConnectionLogResponse{
 		ConnectionLogs: convertConnectionLogs(dblogs),
 		Count:          count,
+		CountCap:       connectionLogCountCap,
 	})
 }

@@ -26,6 +26,12 @@ const RelaySourceHeader = "X-Coder-Relay-Source-Replica"
 const (
 	authorizationHeader = "Authorization"
 	cookieHeader        = "Cookie"
+
+	// relayDrainTimeout is how long an established relay is
+	// kept open after the chat leaves running state, giving
+	// buffered snapshot events time to be forwarded before
+	// the relay is torn down.
+	relayDrainTimeout = 200 * time.Millisecond
 )

 // MultiReplicaSubscribeConfig holds the dependencies for multi-replica chat
@@ -169,6 +175,21 @@ func NewMultiReplicaSubscribeFn(
 		var reconnectTimer *quartz.Timer
 		var reconnectCh <-chan time.Time

+		// drainAndClose is set when the chat transitions away
+		// from running while a relay dial is still in progress.
+		// Instead of canceling the dial immediately, we let it
+		// complete so the snapshot of buffered message_parts
+		// can be forwarded to the subscriber.
+		var drainAndClose bool
+
+		// Drain timer state. When the relay connects in
+		// drain-and-close mode, a short timer is started.
+		// During this window the normal relayPartsCh case
+		// forwards buffered snapshot events. When the timer
+		// fires the relay is torn down.
+		var drainTimer *quartz.Timer
+		var drainTimerCh <-chan time.Time
+
 		// Helper to close relay and stop any pending reconnect
 		// timer.
 		closeRelay := func() {
@@ -200,6 +221,12 @@ func NewMultiReplicaSubscribeFn(
 				reconnectTimer = nil
 				reconnectCh = nil
 			}
+			if drainTimer != nil {
+				drainTimer.Stop()
+				drainTimer = nil
+				drainTimerCh = nil
+			}
+			drainAndClose = false
 		}

 		// openRelayAsync dials the remote replica in a background
@@ -335,16 +362,52 @@ func NewMultiReplicaSubscribeFn(
 					// A nil parts channel signals the dial
 					// failed — schedule a retry.
 					if result.parts == nil {
-						scheduleRelayReconnect()
+						if drainAndClose {
+							// Dial failed and we were only
+							// waiting to drain — nothing to do.
+							drainAndClose = false
+						} else {
+							scheduleRelayReconnect()
+						}
 						continue
-					}
-					// An async relay dial completed; swap
+					} // An async relay dial completed; swap
 					// in the new relay channel.
 					if relayCancel != nil {
 						relayCancel()
 					}
 					relayParts = result.parts
 					relayCancel = result.cancel
+					if drainAndClose {
+						// The chat is no longer running on
+						// the remote worker, but the dial
+						// completed. Verify no new worker
+						// has claimed the chat before we
+						// drain stale parts.
+						currentChat, dbErr := params.DB.GetChatByID(ctx, chatID)
+						if dbErr != nil {
+							logger.Warn(ctx, "failed to check chat status for relay drain",
+								slog.F("chat_id", chatID),
+								slog.Error(dbErr),
+							)
+						}
+						if dbErr == nil && currentChat.Status == database.ChatStatusRunning &&
+							currentChat.WorkerID.Valid &&
+							currentChat.WorkerID.UUID != params.WorkerID {
+							// A new worker picked up the chat;
+							// discard the stale relay and let
+							// openRelayAsync handle the new one.
+							closeRelay()
+						} else {
+							// Chat is still idle — drain the
+							// buffered snapshot before closing.
+							if drainTimer != nil {
+								drainTimer.Stop()
+							}
+							drainTimer = cfg.clock().NewTimer(relayDrainTimeout, "drain")
+							drainTimerCh = drainTimer.C
+							drainAndClose = false
+						}
+					}
 				case <-reconnectCh:
 					reconnectCh = nil
 					// Re-check whether the chat is still
@@ -374,8 +437,31 @@ func NewMultiReplicaSubscribeFn(
 					if sn.Status == database.ChatStatusRunning && sn.WorkerID != uuid.Nil && sn.WorkerID != params.WorkerID {
 						openRelayAsync(sn.WorkerID)
 					} else {
-						closeRelay()
+						switch {
+						case dialCancel != nil && relayParts == nil:
+							// In-progress dial: let it complete
+							// so its snapshot can be forwarded.
+							drainAndClose = true
+						case relayParts != nil:
+							// Active relay: give it a short
+							// window to deliver any remaining
+							// buffered parts before closing.
+							if drainTimer != nil {
+								drainTimer.Stop()
+							}
+							drainTimer = cfg.clock().NewTimer(relayDrainTimeout, "drain")
+							drainTimerCh = drainTimer.C
+						default:
+							closeRelay()
+						}
 					}
+				case <-drainTimerCh:
+					drainTimerCh = nil
+					drainTimer = nil
+					closeRelay()
+					drainTimerCh = nil
+					drainTimer = nil
+					closeRelay()
 				case event, ok := <-relayPartsCh:
 					if !ok {
 						if relayCancel != nil {
@@ -1245,3 +1245,334 @@ func TestSubscribeRelayMultipleReconnects(t *testing.T) {
 	consumePart("relay-3")
 	require.GreaterOrEqual(t, int(callCount.Load()), 3)
 }
+
+// TestSubscribeRelayDialCanceledOnFastCompletion demonstrates a race
+// condition in multi-replica chat streaming where the relay connection
+// from the subscriber replica to the worker replica is canceled before
+// it can be established because the worker completes processing before
+// the async relay dial finishes.
+//
+// Scenario:
+//  1. Subscriber subscribes to a chat while it's in waiting state (no relay).
+//  2. User sends a message → chat becomes pending → worker picks it up.
+//  3. Subscriber receives status=running via pubsub → enterprise opens relay async.
+//  4. Worker completes quickly → publishes committed message + status=waiting.
+//  5. Subscriber receives status=waiting → enterprise cancels the in-progress relay dial.
+//  6. The relay was never established, so no message_part events were delivered.
+//  7. The committed message arrives via pubsub (durable path), but streaming is lost.
+//
+// This reproduces the user-facing issue where refreshing the page is needed
+// to see a response: the streaming tokens never arrive via the relay, and
+// the response only appears after the full committed message is delivered.
+func TestSubscribeRelayDialCanceledOnFastCompletion(t *testing.T) {
+	t.Parallel()
+
+	db, ps := dbtestutil.NewDB(t)
+	workerID := uuid.New()
+	subscriberID := uuid.New()
+
+	var dialAttempted atomic.Bool
+
+	// Gate: closed when the worker finishes processing.
+	workerDone := make(chan struct{})
+
+	openAIURL := chattest.NewOpenAI(t, func(req *chattest.OpenAIRequest) chattest.OpenAIResponse {
+		if !req.Stream {
+			return chattest.OpenAINonStreamingResponse("fast-completion-relay-race")
+		}
+		return chattest.OpenAIStreamingResponse(
+			chattest.OpenAITextChunks("hello ", "world ", "from ", "the ", "worker")...,
+		)
+	})
+
+	// Worker server with a 1-hour acquire interval so it only processes
+	// when explicitly woken by SendMessage's signalWake.
+	workerLogger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+	worker := osschatd.New(osschatd.Config{
+		Logger:                     workerLogger,
+		Database:                   db,
+		ReplicaID:                  workerID,
+		Pubsub:                     ps,
+		PendingChatAcquireInterval: time.Hour,
+		InFlightChatStaleAfter:     testutil.WaitSuperLong,
+	})
+	t.Cleanup(func() {
+		require.NoError(t, worker.Close())
+	})
+
+	// Subscriber's relay dialer blocks until the worker finishes,
+	// simulating a slow relay dial (network latency between replicas).
+	// After the worker completes, the dialer connects to the worker
+	// to retrieve buffered parts from the retained buffer.
+	subscriber := newTestServer(t, db, ps, subscriberID, func(
+		ctx context.Context,
+		chatID uuid.UUID,
+		targetWorkerID uuid.UUID,
+		requestHeader http.Header,
+	) (
+		[]codersdk.ChatStreamEvent,
+		<-chan codersdk.ChatStreamEvent,
+		func(),
+		error,
+	) {
+		dialAttempted.Store(true)
+		// Block until the worker finishes processing, simulating
+		// a slow relay dial.
+		select {
+		case <-workerDone:
+		case <-ctx.Done():
+			return nil, nil, nil, ctx.Err()
+		}
+		// Connect to the worker. The buffer is retained for a
+		// grace period after processing, so the relay still gets
+		// the message_part snapshot.
+		snapshot, relayEvents, cancel, ok := worker.Subscribe(ctx, chatID, requestHeader, math.MaxInt64)
+		if !ok {
+			return nil, nil, nil, xerrors.New("worker subscribe failed")
+		}
+		return snapshot, relayEvents, cancel, nil
+	}, nil)
+
+	ctx := testutil.Context(t, testutil.WaitLong)
+	user, model := seedChatDependencies(ctx, t, db)
+	setOpenAIProviderBaseURL(ctx, t, db, openAIURL)
+
+	// Create the chat in waiting state so the subscriber sees it
+	// before the worker picks it up (avoids the synchronous relay
+	// path in Subscribe).
+	chat := seedWaitingChat(ctx, t, db, user, model, "fast-completion-relay-race")
+
+	// Subscribe from the subscriber replica while the chat is idle.
+	// No relay is opened because the chat is in waiting state.
+	_, events, subCancel, ok := subscriber.Subscribe(ctx, chat.ID, nil, 0)
+	require.True(t, ok)
+	defer subCancel()
+
+	// Send a message via the worker server to transition the chat to
+	// pending and wake the worker's processing loop.
+	_, err := worker.SendMessage(ctx, osschatd.SendMessageOptions{
+		ChatID:    chat.ID,
+		CreatedBy: user.ID,
+		Content:   []codersdk.ChatMessagePart{codersdk.ChatMessageText("hello")},
+	})
+	require.NoError(t, err)
+
+	// Wait for the worker to fully process the chat.
+	require.Eventually(t, func() bool {
+		fromDB, dbErr := db.GetChatByID(ctx, chat.ID)
+		if dbErr != nil {
+			return false
+		}
+		return fromDB.Status == database.ChatStatusWaiting
+	}, testutil.WaitMedium, testutil.IntervalFast)
+
+	// Release the relay dial now that the worker is done.
+	close(workerDone)
+
+	// Collect all events that arrived at the subscriber.
+	var messageParts []string
+	var committedAssistantMsgs int
+
+	// Drain events until we see both the committed message (via
+	// pubsub) and at least one streaming part (via relay
+	// drain-and-close).
+	require.Eventually(t, func() bool {
+		select {
+		case event := <-events:
+			switch event.Type {
+			case codersdk.ChatStreamEventTypeMessagePart:
+				if event.MessagePart != nil {
+					messageParts = append(messageParts, event.MessagePart.Part.Text)
+				}
+			case codersdk.ChatStreamEventTypeMessage:
+				if event.Message != nil && event.Message.Role == codersdk.ChatMessageRoleAssistant {
+					committedAssistantMsgs++
+				}
+			}
+			return committedAssistantMsgs > 0 && len(messageParts) > 0
+		default:
+			return false
+		}
+	}, testutil.WaitLong, testutil.IntervalFast)
+
+	// The committed assistant message arrives via pubsub → DB query
+	// (durable path).
+	require.Equal(t, 1, committedAssistantMsgs,
+		"committed assistant message should arrive via pubsub durable path")
+
+	// The relay dial was attempted when status=running arrived.
+	require.True(t, dialAttempted.Load(),
+		"relay dial should have been attempted when status changed to running")
+
+	// Streaming parts are now received even though the relay was
+	// slower than the worker: the OSS buffer retention grace period
+	// keeps parts available, and the enterprise relay completes the
+	// dial (drain-and-close) instead of canceling it immediately.
+	require.NotEmpty(t, messageParts,
+		"streaming parts should be received via the relay even when the "+
+			"worker completes before the relay is established")
+}
+
+// TestSubscribeRelayEstablishedMidStream demonstrates that when the
+// relay is established while the worker is still streaming, the
+// subscriber receives buffered parts via the relay snapshot and live
+// parts through the relay channel.
+//
+// This is the complementary test to TestSubscribeRelayDialCanceledOnFastCompletion:
+// it shows the relay mechanism works correctly when timing is favorable
+// (relay connects before the worker finishes), contrasting with the race
+// condition where the relay is too slow.
+func TestSubscribeRelayEstablishedMidStream(t *testing.T) {
+	t.Parallel()
+
+	db, ps := dbtestutil.NewDB(t)
+	workerID := uuid.New()
+	subscriberID := uuid.New()
+
+	// Gate: worker blocks after first streaming request until we
+	// release it. This gives the relay time to establish.
+	firstChunkEmitted := make(chan struct{})
+	continueStreaming := make(chan struct{})
+
+	openAIURL := chattest.NewOpenAI(t, func(req *chattest.OpenAIRequest) chattest.OpenAIResponse {
+		if !req.Stream {
+			return chattest.OpenAINonStreamingResponse("mid-stream-relay")
+		}
+		// Signal that the first streaming request was received,
+		// then block until released.
+		select {
+		case <-firstChunkEmitted:
+		default:
+			close(firstChunkEmitted)
+		}
+		<-continueStreaming
+		return chattest.OpenAIStreamingResponse(
+			chattest.OpenAITextChunks("continued ", "response")...,
+		)
+	})
+
+	// Worker with a 1-hour acquire interval; only processes when
+	// explicitly woken.
+	workerLogger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+	worker := osschatd.New(osschatd.Config{
+		Logger:                     workerLogger,
+		Database:                   db,
+		ReplicaID:                  workerID,
+		Pubsub:                     ps,
+		PendingChatAcquireInterval: time.Hour,
+		InFlightChatStaleAfter:     testutil.WaitSuperLong,
+	})
+	t.Cleanup(func() {
+		require.NoError(t, worker.Close())
+	})
+
+	// Subscriber's dialer connects to the worker with no delay.
+	// This simulates a relay that succeeds promptly.
+	subscriber := newTestServer(t, db, ps, subscriberID, func(
+		ctx context.Context,
+		chatID uuid.UUID,
+		targetWorkerID uuid.UUID,
+		requestHeader http.Header,
+	) (
+		[]codersdk.ChatStreamEvent,
+		<-chan codersdk.ChatStreamEvent,
+		func(),
+		error,
+	) {
+		if targetWorkerID != workerID {
+			return nil, nil, nil, xerrors.Errorf("unexpected relay target %s", targetWorkerID)
+		}
+		snapshot, relayEvents, cancel, ok := worker.Subscribe(ctx, chatID, requestHeader, math.MaxInt64)
+		if !ok {
+			return nil, nil, nil, xerrors.New("worker subscribe failed")
+		}
+		return snapshot, relayEvents, cancel, nil
+	}, nil)
+
+	ctx := testutil.Context(t, testutil.WaitLong)
+	user, model := seedChatDependencies(ctx, t, db)
+	setOpenAIProviderBaseURL(ctx, t, db, openAIURL)
+
+	// Create the chat in waiting state.
+	chat := seedWaitingChat(ctx, t, db, user, model, "mid-stream-relay")
+
+	// Subscribe from the subscriber replica while the chat is idle.
+	_, events, subCancel, ok := subscriber.Subscribe(ctx, chat.ID, nil, 0)
+	require.True(t, ok)
+	defer subCancel()
+
+	// Send a message to make the chat pending and wake the worker.
+	_, err := worker.SendMessage(ctx, osschatd.SendMessageOptions{
+		ChatID:    chat.ID,
+		CreatedBy: user.ID,
+		Content:   []codersdk.ChatMessagePart{codersdk.ChatMessageText("hello")},
+	})
+	require.NoError(t, err)
+
+	// Wait for the worker to reach the LLM (first streaming request).
+	select {
+	case <-firstChunkEmitted:
+	case <-ctx.Done():
+		t.Fatal("timed out waiting for worker to start streaming")
+	}
+
+	// Wait for the subscriber to receive the running status, which
+	// triggers the relay. Because the dialer is non-blocking, the
+	// relay establishes promptly.
+	require.Eventually(t, func() bool {
+		select {
+		case event := <-events:
+			return event.Type == codersdk.ChatStreamEventTypeStatus &&
+				event.Status != nil &&
+				event.Status.Status == codersdk.ChatStatusRunning
+		default:
+			return false
+		}
+	}, testutil.WaitMedium, testutil.IntervalFast)
+
+	// Now release the worker to continue streaming.
+	close(continueStreaming)
+
+	// Wait for the worker to complete.
+	require.Eventually(t, func() bool {
+		fromDB, dbErr := db.GetChatByID(ctx, chat.ID)
+		if dbErr != nil {
+			return false
+		}
+		return fromDB.Status == database.ChatStatusWaiting
+	}, testutil.WaitMedium, testutil.IntervalFast)
+
+	// Collect remaining events.
+	var messageParts []string
+	var hasCommittedMsg bool
+
+	require.Eventually(t, func() bool {
+		select {
+		case event := <-events:
+			switch event.Type {
+			case codersdk.ChatStreamEventTypeMessagePart:
+				if event.MessagePart != nil {
+					messageParts = append(messageParts, event.MessagePart.Part.Text)
+				}
+			case codersdk.ChatStreamEventTypeMessage:
+				if event.Message != nil && event.Message.Role == codersdk.ChatMessageRoleAssistant {
+					hasCommittedMsg = true
+				}
+			}
+			return hasCommittedMsg
+		default:
+			return false
+		}
+	}, testutil.WaitLong, testutil.IntervalFast)
+
+	// The committed message arrives via pubsub.
+	require.True(t, hasCommittedMsg,
+		"committed assistant message should arrive")
+
+	// When the relay is established mid-stream, streaming parts
+	// SHOULD be received through the relay. This contrasts with
+	// TestSubscribeRelayDialCanceledOnFastCompletion where no parts
+	// arrive because the relay is never established.
+	require.NotEmpty(t, messageParts,
+		"streaming parts should be received when relay establishes while worker is still streaming")
+}
@@ -33,7 +33,7 @@ data "coder_task" "me" {}
 module "claude-code" {
  count               = data.coder_workspace.me.start_count
  source              = "registry.coder.com/coder/claude-code/coder"
-  version             = "4.8.2"
+  version             = "4.9.1"
  agent_id            = coder_agent.main.id
  workdir             = "/home/coder/projects"
  order               = 999
@@ -91,7 +91,7 @@ require (
 	github.com/acarl005/stripansi v0.0.0-20180116102854-5a71ef0e047d
 	github.com/adrg/xdg v0.5.0
 	github.com/ammario/tlru v0.4.0
-	github.com/andybalholm/brotli v1.2.0
+	github.com/andybalholm/brotli v1.2.1
 	github.com/aquasecurity/trivy-iac v0.8.0
 	github.com/armon/circbuf v0.0.0-20190214190532-5111143e8da2
 	github.com/awalterschulze/gographviz v2.0.3+incompatible
@@ -136,11 +136,11 @@ require (
 	github.com/go-chi/chi/v5 v5.2.4
 	github.com/go-chi/cors v1.2.1
 	github.com/go-chi/httprate v0.15.0
-	github.com/go-jose/go-jose/v4 v4.1.3
+	github.com/go-jose/go-jose/v4 v4.1.4
 	github.com/go-logr/logr v1.4.3
 	github.com/go-playground/validator/v10 v10.30.0
 	github.com/gofrs/flock v0.13.0
-	github.com/gohugoio/hugo v0.159.2
+	github.com/gohugoio/hugo v0.160.0
 	github.com/golang-jwt/jwt/v4 v4.5.2
 	github.com/golang-migrate/migrate/v4 v4.19.0
 	github.com/gomarkdown/markdown v0.0.0-20240930133441-72d49d9543d8
@@ -162,7 +162,7 @@ require (
 	github.com/justinas/nosurf v1.2.0
 	github.com/kballard/go-shellquote v0.0.0-20180428030007-95032a82bc51
 	github.com/kirsle/configdir v0.0.0-20170128060238-e45d2f54772f
-	github.com/klauspost/compress v1.18.4
+	github.com/klauspost/compress v1.18.5
 	github.com/lib/pq v1.10.9
 	github.com/mattn/go-isatty v0.0.20
 	github.com/mitchellh/go-wordwrap v1.0.1
@@ -193,7 +193,7 @@ require (
 	github.com/tidwall/gjson v1.18.0
 	github.com/u-root/u-root v0.14.0
 	github.com/unrolled/secure v1.17.0
-	github.com/valyala/fasthttp v1.69.0
+	github.com/valyala/fasthttp v1.70.0
 	github.com/wagslane/go-password-validator v0.3.0
 	github.com/zclconf/go-cty-yaml v1.2.0
 	go.mozilla.org/pkcs7 v0.9.0
@@ -218,7 +218,7 @@ require (
 	golang.org/x/text v0.35.0
 	golang.org/x/tools v0.43.0
 	golang.org/x/xerrors v0.0.0-20240903120638-7835f813f4da
-	google.golang.org/api v0.273.0
+	google.golang.org/api v0.274.0
 	google.golang.org/grpc v1.80.0
 	google.golang.org/protobuf v1.36.11
 	gopkg.in/DataDog/dd-trace-go.v1 v1.74.0
@@ -434,7 +434,7 @@ require (
 	github.com/xeipuuv/gojsonschema v1.2.0 // indirect
 	github.com/xi2/xz v0.0.0-20171230120015-48954b6210f8 // indirect
 	github.com/yashtewari/glob-intersection v0.2.0 // indirect
-	github.com/yuin/goldmark v1.7.17 // indirect
+	github.com/yuin/goldmark v1.8.2 // indirect
 	github.com/yuin/goldmark-emoji v1.0.6 // indirect
 	github.com/yusufpapurcu/wmi v1.2.4 // indirect
 	github.com/zclconf/go-cty v1.17.0
@@ -128,8 +128,8 @@ github.com/ammario/tlru v0.4.0 h1:sJ80I0swN3KOX2YxC6w8FbCqpQucWdbb+J36C05FPuU=
 github.com/ammario/tlru v0.4.0/go.mod h1:aYzRFu0XLo4KavE9W8Lx7tzjkX+pAApz+NgcKYIFUBQ=
 github.com/andreyvit/diff v0.0.0-20170406064948-c7f18ee00883 h1:bvNMNQO63//z+xNgfBlViaCIJKLlCJ6/fmUseuG0wVQ=
 github.com/andreyvit/diff v0.0.0-20170406064948-c7f18ee00883/go.mod h1:rCTlJbsFo29Kk6CurOXKm700vrz8f0KW0JNfpkRJY/8=
-github.com/andybalholm/brotli v1.2.0 h1:ukwgCxwYrmACq68yiUqwIWnGY0cTPox/M94sVwToPjQ=
-github.com/andybalholm/brotli v1.2.0/go.mod h1:rzTDkvFWvIrjDXZHkuS16NPggd91W3kUSvPlQ1pLaKY=
+github.com/andybalholm/brotli v1.2.1 h1:R+f5xP285VArJDRgowrfb9DqL18yVK0gKAW/F+eTWro=
+github.com/andybalholm/brotli v1.2.1/go.mod h1:rzTDkvFWvIrjDXZHkuS16NPggd91W3kUSvPlQ1pLaKY=
 github.com/anmitsu/go-shlex v0.0.0-20200514113438-38f4b401e2be h1:9AeTilPcZAjCFIImctFaOjnTIavg87rW78vTPkQqLI8=
 github.com/anmitsu/go-shlex v0.0.0-20200514113438-38f4b401e2be/go.mod h1:ySMOLuWl6zY27l47sB3qLNK6tF2fkHG55UZxx8oIVo4=
 github.com/apparentlymart/go-cidr v1.1.0 h1:2mAhrMoF+nhXqxTzSZMUzDHkLjmIHC+Zzn4tdgBZjnU=
@@ -518,8 +518,8 @@ github.com/go-git/go-git/v5 v5.17.1 h1:WnljyxIzSj9BRRUlnmAU35ohDsjRK0EKmL0evDqi5
 github.com/go-git/go-git/v5 v5.17.1/go.mod h1:pW/VmeqkanRFqR6AljLcs7EA7FbZaN5MQqO7oZADXpo=
 github.com/go-ini/ini v1.67.0 h1:z6ZrTEZqSWOTyH2FlglNbNgARyHG8oLW9gMELqKr06A=
 github.com/go-ini/ini v1.67.0/go.mod h1:ByCAeIL28uOIIG0E3PJtZPDL8WnHpFKFOtgjp+3Ies8=
-github.com/go-jose/go-jose/v4 v4.1.3 h1:CVLmWDhDVRa6Mi/IgCgaopNosCaHz7zrMeF9MlZRkrs=
-github.com/go-jose/go-jose/v4 v4.1.3/go.mod h1:x4oUasVrzR7071A4TnHLGSPpNOm2a21K9Kf04k1rs08=
+github.com/go-jose/go-jose/v4 v4.1.4 h1:moDMcTHmvE6Groj34emNPLs/qtYXRVcd6S7NHbHz3kA=
+github.com/go-jose/go-jose/v4 v4.1.4/go.mod h1:x4oUasVrzR7071A4TnHLGSPpNOm2a21K9Kf04k1rs08=
 github.com/go-json-experiment/json v0.0.0-20251027170946-4849db3c2f7e h1:Lf/gRkoycfOBPa42vU2bbgPurFong6zXeFtPoxholzU=
 github.com/go-json-experiment/json v0.0.0-20251027170946-4849db3c2f7e/go.mod h1:uNVvRXArCGbZ508SxYYTC5v1JWoz2voff5pm25jU1Ok=
 github.com/go-logr/logr v1.2.0/go.mod h1:jdQByPbusPIv2/zmleS9BjJVeZ6kBagPoEUsqbVz/1A=
@@ -611,12 +611,12 @@ github.com/gohugoio/hashstructure v0.6.0 h1:7wMB/2CfXoThFYhdWRGv3u3rUM761Cq29CxU
 github.com/gohugoio/hashstructure v0.6.0/go.mod h1:lapVLk9XidheHG1IQ4ZSbyYrXcaILU1ZEP/+vno5rBQ=
 github.com/gohugoio/httpcache v0.8.0 h1:hNdsmGSELztetYCsPVgjA960zSa4dfEqqF/SficorCU=
 github.com/gohugoio/httpcache v0.8.0/go.mod h1:fMlPrdY/vVJhAriLZnrF5QpN3BNAcoBClgAyQd+lGFI=
-github.com/gohugoio/hugo v0.159.2 h1:tpS6pcShcP3Khl8WA1NAxVHi2D3/ib9BbM8+m7NECUA=
-github.com/gohugoio/hugo v0.159.2/go.mod h1:vKww5V9i8MYzFD8JVvhRN+AKdDfKV0UvbFpmCDtTr/A=
-github.com/gohugoio/hugo-goldmark-extensions/extras v0.6.0 h1:c16engMi6zyOGeCrP73RWC9fom94wXGpVzncu3GXBjI=
-github.com/gohugoio/hugo-goldmark-extensions/extras v0.6.0/go.mod h1:e3+TRCT4Uz6NkZOAVMOMgPeJ+7KEtQMX8hdB+WG4qRs=
-github.com/gohugoio/hugo-goldmark-extensions/passthrough v0.4.0 h1:awFlqaCQ0N/RS9ndIBpDYNms101I1sGbDRG1bksa5Js=
-github.com/gohugoio/hugo-goldmark-extensions/passthrough v0.4.0/go.mod h1:lK1CjqrueCd3OBnsLLQJGrQ+uodWfT9M9Cq2zfDWJCE=
+github.com/gohugoio/hugo v0.160.0 h1:WmmygLg2ahijM4w2VHFn/DdBR+OpJ9H9pH3d8OApNDY=
+github.com/gohugoio/hugo v0.160.0/go.mod h1:+VA5jOO3iGELh+6cig098PT2Cd9iNhwUPRqCUe3Ce7w=
+github.com/gohugoio/hugo-goldmark-extensions/extras v0.7.0 h1:I/n6v7VImJ3aISLnn73JAHXyjcQsMVvbguQPTk9Ehus=
+github.com/gohugoio/hugo-goldmark-extensions/extras v0.7.0/go.mod h1:9LJNfKWFmhEJ7HW0in5znezMwH+FYMBIhNZ3VWtRcRs=
+github.com/gohugoio/hugo-goldmark-extensions/passthrough v0.5.0 h1:p13Q0DBCrBRpJGtbtlgkYNCs4TnIlZJh8vHgnAiofrI=
+github.com/gohugoio/hugo-goldmark-extensions/passthrough v0.5.0/go.mod h1:ob9PCHy/ocsQhTz68uxhyInaYCbbVNpOOrJkIoSeD+8=
 github.com/golang-jwt/jwt/v4 v4.5.2 h1:YtQM7lnr8iZ+j5q71MGKkNw9Mn7AjHM68uc9g5fXeUI=
 github.com/golang-jwt/jwt/v4 v4.5.2/go.mod h1:m21LjoU+eqJr34lmDMbreY2eSTRJ1cv77w39/MY0Ch0=
 github.com/golang-jwt/jwt/v5 v5.2.1/go.mod h1:pqrtFR0X4osieyHYxtmOUWsAWrfe1Q5UVIyoH402zdk=
@@ -794,8 +794,8 @@ github.com/kirsle/configdir v0.0.0-20170128060238-e45d2f54772f h1:dKccXx7xA56UNq
 github.com/kirsle/configdir v0.0.0-20170128060238-e45d2f54772f/go.mod h1:4rEELDSfUAlBSyUjPG0JnaNGjf13JySHFeRdD/3dLP0=
 github.com/kisielk/errcheck v1.5.0/go.mod h1:pFxgyoBC7bSaBwPgfKdkLd5X25qrDl4LWUI2bnpBCr8=
 github.com/kisielk/gotool v1.0.0/go.mod h1:XhKaO+MFFWcvkIS/tQcRk01m1F5IRFswLeQ+oQHNcck=
-github.com/klauspost/compress v1.18.4 h1:RPhnKRAQ4Fh8zU2FY/6ZFDwTVTxgJ/EMydqSTzE9a2c=
-github.com/klauspost/compress v1.18.4/go.mod h1:R0h/fSBs8DE4ENlcrlib3PsXS61voFxhIs2DeRhCvJ4=
+github.com/klauspost/compress v1.18.5 h1:/h1gH5Ce+VWNLSWqPzOVn6XBO+vJbCNGvjoaGBFW2IE=
+github.com/klauspost/compress v1.18.5/go.mod h1:cwPg85FWrGar70rWktvGQj8/hthj3wpl0PGDogxkrSQ=
 github.com/klauspost/cpuid/v2 v2.2.10 h1:tBs3QSyvjDyFTq3uoc/9xFpCuOsJQFNPiAhYdw2skhE=
 github.com/klauspost/cpuid/v2 v2.2.10/go.mod h1:hqwkgyIinND0mEev00jJYCxPNVRVXFQeu1XKlok6oO0=
 github.com/kortschak/wol v0.0.0-20200729010619-da482cc4850a h1:+RR6SqnTkDLWyICxS1xpjCi/3dhyV+TgZwA6Ww3KncQ=
@@ -1188,8 +1188,8 @@ github.com/urfave/cli/v2 v2.27.5 h1:WoHEJLdsXr6dDWoJgMq/CboDmyY/8HMMH1fTECbih+w=
 github.com/urfave/cli/v2 v2.27.5/go.mod h1:3Sevf16NykTbInEnD0yKkjDAeZDS0A6bzhBH5hrMvTQ=
 github.com/valyala/bytebufferpool v1.0.0 h1:GqA5TC/0021Y/b9FG4Oi9Mr3q7XYx6KllzawFIhcdPw=
 github.com/valyala/bytebufferpool v1.0.0/go.mod h1:6bBcMArwyJ5K/AmCkWv1jt77kVWyCJ6HpOuEn7z0Csc=
-github.com/valyala/fasthttp v1.69.0 h1:fNLLESD2SooWeh2cidsuFtOcrEi4uB4m1mPrkJMZyVI=
-github.com/valyala/fasthttp v1.69.0/go.mod h1:4wA4PfAraPlAsJ5jMSqCE2ug5tqUPwKXxVj8oNECGcw=
+github.com/valyala/fasthttp v1.70.0 h1:LAhMGcWk13QZWm85+eg8ZBNbrq5mnkWFGbHMUJHIdXA=
+github.com/valyala/fasthttp v1.70.0/go.mod h1:oDZEHHkJ/Buyklg6uURmYs19442zFSnCIfX3j1FY3pE=
 github.com/valyala/fastjson v1.6.4 h1:uAUNq9Z6ymTgGhcm0UynUAB6tlbakBrz6CQFax3BXVQ=
 github.com/valyala/fastjson v1.6.4/go.mod h1:CLCAqky6SMuOcxStkYQvblddUtoRxhYMGLrsQns1aXY=
 github.com/vbatts/tar-split v0.12.2 h1:w/Y6tjxpeiFMR47yzZPlPj/FcPLpXbTUi/9H7d3CPa4=
@@ -1252,8 +1252,8 @@ github.com/yuin/goldmark v1.1.27/go.mod h1:3hX8gzYuyVAZsxl0MRgGTJEmQBFcNTphYh9de
 github.com/yuin/goldmark v1.2.1/go.mod h1:3hX8gzYuyVAZsxl0MRgGTJEmQBFcNTphYh9decYSb74=
 github.com/yuin/goldmark v1.3.5/go.mod h1:mwnBkeHKe2W/ZEtQ+71ViKU8L12m81fl3OWwC1Zlc8k=
 github.com/yuin/goldmark v1.4.13/go.mod h1:6yULJ656Px+3vBD8DxQVa3kxgyrAnzto9xy5taEt/CY=
-github.com/yuin/goldmark v1.7.17 h1:p36OVWwRb246iHxA/U4p8OPEpOTESm4n+g+8t0EE5uA=
-github.com/yuin/goldmark v1.7.17/go.mod h1:ip/1k0VRfGynBgxOz0yCqHrbZXhcjxyuS66Brc7iBKg=
+github.com/yuin/goldmark v1.8.2 h1:kEGpgqJXdgbkhcOgBxkC0X0PmoPG1ZyoZ117rDVp4zE=
+github.com/yuin/goldmark v1.8.2/go.mod h1:ip/1k0VRfGynBgxOz0yCqHrbZXhcjxyuS66Brc7iBKg=
 github.com/yuin/goldmark-emoji v1.0.6 h1:QWfF2FYaXwL74tfGOW5izeiZepUDroDJfWubQI9HTHs=
 github.com/yuin/goldmark-emoji v1.0.6/go.mod h1:ukxJDKFpdFb5x0a5HqbdlcKtebh086iJpI31LTKmWuA=
 github.com/yusufpapurcu/wmi v1.2.4 h1:zFUKzehAFReQwLys1b/iSMl+JQGSCSjtVqQn9bBrPo0=
@@ -1375,8 +1375,8 @@ golang.org/x/crypto v0.49.0 h1:+Ng2ULVvLHnJ/ZFEq4KdcDd/cfjrrjjNSXNzxg0Y4U4=
 golang.org/x/crypto v0.49.0/go.mod h1:ErX4dUh2UM+CFYiXZRTcMpEcN8b/1gxEuv3nODoYtCA=
 golang.org/x/exp v0.0.0-20260218203240-3dfff04db8fa h1:Zt3DZoOFFYkKhDT3v7Lm9FDMEV06GpzjG2jrqW+QTE0=
 golang.org/x/exp v0.0.0-20260218203240-3dfff04db8fa/go.mod h1:K79w1Vqn7PoiZn+TkNpx3BUWUQksGO3JcVX6qIjytmA=
-golang.org/x/image v0.37.0 h1:ZiRjArKI8GwxZOoEtUfhrBtaCN+4b/7709dlT6SSnQA=
-golang.org/x/image v0.37.0/go.mod h1:/3f6vaXC+6CEanU4KJxbcUZyEePbyKbaLoDOe4ehFYY=
+golang.org/x/image v0.38.0 h1:5l+q+Y9JDC7mBOMjo4/aPhMDcxEptsX+Tt3GgRQRPuE=
+golang.org/x/image v0.38.0/go.mod h1:/3f6vaXC+6CEanU4KJxbcUZyEePbyKbaLoDOe4ehFYY=
 golang.org/x/mod v0.2.0/go.mod h1:s0Qsj1ACt9ePp/hMypM3fl4fZqREWJwdYDEqhRiZZUA=
 golang.org/x/mod v0.3.0/go.mod h1:s0Qsj1ACt9ePp/hMypM3fl4fZqREWJwdYDEqhRiZZUA=
 golang.org/x/mod v0.4.2/go.mod h1:s0Qsj1ACt9ePp/hMypM3fl4fZqREWJwdYDEqhRiZZUA=
@@ -1514,8 +1514,8 @@ golang.zx2c4.com/wireguard/windows v0.5.3 h1:On6j2Rpn3OEMXqBq00QEDC7bWSZrPIHKIus
 golang.zx2c4.com/wireguard/windows v0.5.3/go.mod h1:9TEe8TJmtwyQebdFwAkEWOPr3prrtqm+REGFifP60hI=
 gonum.org/v1/gonum v0.17.0 h1:VbpOemQlsSMrYmn7T2OUvQ4dqxQXU+ouZFQsZOx50z4=
 gonum.org/v1/gonum v0.17.0/go.mod h1:El3tOrEuMpv2UdMrbNlKEh9vd86bmQ6vqIcDwxEOc1E=
-google.golang.org/api v0.273.0 h1:r/Bcv36Xa/te1ugaN1kdJ5LoA5Wj/cL+a4gj6FiPBjQ=
-google.golang.org/api v0.273.0/go.mod h1:JbAt7mF+XVmWu6xNP8/+CTiGH30ofmCmk9nM8d8fHew=
+google.golang.org/api v0.274.0 h1:aYhycS5QQCwxHLwfEHRRLf9yNsfvp1JadKKWBE54RFA=
+google.golang.org/api v0.274.0/go.mod h1:JbAt7mF+XVmWu6xNP8/+CTiGH30ofmCmk9nM8d8fHew=
 google.golang.org/appengine v1.1.0/go.mod h1:EbEs0AVv82hx2wNQdGPgUI5lhzA/G0D9YwlJXL52JkM=
 google.golang.org/appengine v1.6.8 h1:IhEN5q69dyKagZPYMSdIjS2HqprW324FRQZJcGqPAsM=
 google.golang.org/appengine v1.6.8/go.mod h1:1jJ3jBArFh5pcgW8gCtRJnepW8FzD1V44FJffLiz/Ds=
@@ -9,7 +9,7 @@
 		"storybook": "pnpm run -C site/ storybook"
 	},
 	"devDependencies": {
-		"@biomejs/biome": "2.2.0",
+		"@biomejs/biome": "2.4.10",
 		"markdown-table-formatter": "^1.6.1",
 		"markdownlint-cli2": "^0.16.0",
 		"quicktype": "^23.0.0"
@@ -12,8 +12,8 @@ importers:
  .:
    devDependencies:
      '@biomejs/biome':
-        specifier: 2.2.0
-        version: 2.2.0
+        specifier: 2.4.10
+        version: 2.4.10
      markdown-table-formatter:
        specifier: ^1.6.1
        version: 1.6.1
@@ -26,55 +26,55 @@ importers:

 packages:

-  '@biomejs/biome@2.2.0':
-    resolution: {integrity: sha512-3On3RSYLsX+n9KnoSgfoYlckYBoU6VRM22cw1gB4Y0OuUVSYd/O/2saOJMrA4HFfA1Ff0eacOvMN1yAAvHtzIw==}
+  '@biomejs/biome@2.4.10':
+    resolution: {integrity: sha512-xxA3AphFQ1geij4JTHXv4EeSTda1IFn22ye9LdyVPoJU19fNVl0uzfEuhsfQ4Yue/0FaLs2/ccVi4UDiE7R30w==}
    engines: {node: '>=14.21.3'}
    hasBin: true

-  '@biomejs/cli-darwin-arm64@2.2.0':
-    resolution: {integrity: sha512-zKbwUUh+9uFmWfS8IFxmVD6XwqFcENjZvEyfOxHs1epjdH3wyyMQG80FGDsmauPwS2r5kXdEM0v/+dTIA9FXAg==}
+  '@biomejs/cli-darwin-arm64@2.4.10':
+    resolution: {integrity: sha512-vuzzI1cWqDVzOMIkYyHbKqp+AkQq4K7k+UCXWpkYcY/HDn1UxdsbsfgtVpa40shem8Kax4TLDLlx8kMAecgqiw==}
    engines: {node: '>=14.21.3'}
    cpu: [arm64]
    os: [darwin]

-  '@biomejs/cli-darwin-x64@2.2.0':
-    resolution: {integrity: sha512-+OmT4dsX2eTfhD5crUOPw3RPhaR+SKVspvGVmSdZ9y9O/AgL8pla6T4hOn1q+VAFBHuHhsdxDRJgFCSC7RaMOw==}
+  '@biomejs/cli-darwin-x64@2.4.10':
+    resolution: {integrity: sha512-14fzASRo+BPotwp7nWULy2W5xeUyFnTaq1V13Etrrxkrih+ez/2QfgFm5Ehtf5vSjtgx/IJycMMpn5kPd5ZNaA==}
    engines: {node: '>=14.21.3'}
    cpu: [x64]
    os: [darwin]

-  '@biomejs/cli-linux-arm64-musl@2.2.0':
-    resolution: {integrity: sha512-egKpOa+4FL9YO+SMUMLUvf543cprjevNc3CAgDNFLcjknuNMcZ0GLJYa3EGTCR2xIkIUJDVneBV3O9OcIlCEZQ==}
+  '@biomejs/cli-linux-arm64-musl@2.4.10':
+    resolution: {integrity: sha512-WrJY6UuiSD/Dh+nwK2qOTu8kdMDlLV3dLMmychIghHPAysWFq1/DGC1pVZx8POE3ZkzKR3PUUnVrtZfMfaJjyQ==}
    engines: {node: '>=14.21.3'}
    cpu: [arm64]
    os: [linux]

-  '@biomejs/cli-linux-arm64@2.2.0':
-    resolution: {integrity: sha512-6eoRdF2yW5FnW9Lpeivh7Mayhq0KDdaDMYOJnH9aT02KuSIX5V1HmWJCQQPwIQbhDh68Zrcpl8inRlTEan0SXw==}
+  '@biomejs/cli-linux-arm64@2.4.10':
+    resolution: {integrity: sha512-7MH1CMW5uuxQ/s7FLST63qF8B3Hgu2HRdZ7tA1X1+mk+St4JOuIrqdhIBnnyqeyWJNI+Bww7Es5QZ0wIc1Cmkw==}
    engines: {node: '>=14.21.3'}
    cpu: [arm64]
    os: [linux]

-  '@biomejs/cli-linux-x64-musl@2.2.0':
-    resolution: {integrity: sha512-I5J85yWwUWpgJyC1CcytNSGusu2p9HjDnOPAFG4Y515hwRD0jpR9sT9/T1cKHtuCvEQ/sBvx+6zhz9l9wEJGAg==}
+  '@biomejs/cli-linux-x64-musl@2.4.10':
+    resolution: {integrity: sha512-kDTi3pI6PBN6CiczsWYOyP2zk0IJI08EWEQyDMQWW221rPaaEz6FvjLhnU07KMzLv8q3qSuoB93ua6inSQ55Tw==}
    engines: {node: '>=14.21.3'}
    cpu: [x64]
    os: [linux]

-  '@biomejs/cli-linux-x64@2.2.0':
-    resolution: {integrity: sha512-5UmQx/OZAfJfi25zAnAGHUMuOd+LOsliIt119x2soA2gLggQYrVPA+2kMUxR6Mw5M1deUF/AWWP2qpxgH7Nyfw==}
+  '@biomejs/cli-linux-x64@2.4.10':
+    resolution: {integrity: sha512-tZLvEEi2u9Xu1zAqRjTcpIDGVtldigVvzug2fTuPG0ME/g8/mXpRPcNgLB22bGn6FvLJpHHnqLnwliOu8xjYrg==}
    engines: {node: '>=14.21.3'}
    cpu: [x64]
    os: [linux]

-  '@biomejs/cli-win32-arm64@2.2.0':
-    resolution: {integrity: sha512-n9a1/f2CwIDmNMNkFs+JI0ZjFnMO0jdOyGNtihgUNFnlmd84yIYY2KMTBmMV58ZlVHjgmY5Y6E1hVTnSRieggA==}
+  '@biomejs/cli-win32-arm64@2.4.10':
+    resolution: {integrity: sha512-umwQU6qPzH+ISTf/eHyJ/QoQnJs3V9Vpjz2OjZXe9MVBZ7prgGafMy7yYeRGnlmDAn87AKTF3Q6weLoMGpeqdQ==}
    engines: {node: '>=14.21.3'}
    cpu: [arm64]
    os: [win32]

-  '@biomejs/cli-win32-x64@2.2.0':
-    resolution: {integrity: sha512-Nawu5nHjP/zPKTIryh2AavzTc/KEg4um/MxWdXW0A6P/RZOyIpa7+QSjeXwAwX/utJGaCoXRPWtF3m5U/bB3Ww==}
+  '@biomejs/cli-win32-x64@2.4.10':
+    resolution: {integrity: sha512-aW/JU5GuyH4uxMrNYpoC2kjaHlyJGLgIa3XkhPEZI0uKhZhJZU8BuEyJmvgzSPQNGozBwWjC972RaNdcJ9KyJg==}
    engines: {node: '>=14.21.3'}
    cpu: [x64]
    os: [win32]
@@ -778,39 +778,39 @@ packages:

 snapshots:

-  '@biomejs/biome@2.2.0':
+  '@biomejs/biome@2.4.10':
    optionalDependencies:
-      '@biomejs/cli-darwin-arm64': 2.2.0
-      '@biomejs/cli-darwin-x64': 2.2.0
-      '@biomejs/cli-linux-arm64': 2.2.0
-      '@biomejs/cli-linux-arm64-musl': 2.2.0
-      '@biomejs/cli-linux-x64': 2.2.0
-      '@biomejs/cli-linux-x64-musl': 2.2.0
-      '@biomejs/cli-win32-arm64': 2.2.0
-      '@biomejs/cli-win32-x64': 2.2.0
+      '@biomejs/cli-darwin-arm64': 2.4.10
+      '@biomejs/cli-darwin-x64': 2.4.10
+      '@biomejs/cli-linux-arm64': 2.4.10
+      '@biomejs/cli-linux-arm64-musl': 2.4.10
+      '@biomejs/cli-linux-x64': 2.4.10
+      '@biomejs/cli-linux-x64-musl': 2.4.10
+      '@biomejs/cli-win32-arm64': 2.4.10
+      '@biomejs/cli-win32-x64': 2.4.10

-  '@biomejs/cli-darwin-arm64@2.2.0':
+  '@biomejs/cli-darwin-arm64@2.4.10':
    optional: true

-  '@biomejs/cli-darwin-x64@2.2.0':
+  '@biomejs/cli-darwin-x64@2.4.10':
    optional: true

-  '@biomejs/cli-linux-arm64-musl@2.2.0':
+  '@biomejs/cli-linux-arm64-musl@2.4.10':
    optional: true

-  '@biomejs/cli-linux-arm64@2.2.0':
+  '@biomejs/cli-linux-arm64@2.4.10':
    optional: true

-  '@biomejs/cli-linux-x64-musl@2.2.0':
+  '@biomejs/cli-linux-x64-musl@2.4.10':
    optional: true

-  '@biomejs/cli-linux-x64@2.2.0':
+  '@biomejs/cli-linux-x64@2.4.10':
    optional: true

-  '@biomejs/cli-win32-arm64@2.2.0':
+  '@biomejs/cli-win32-arm64@2.4.10':
    optional: true

-  '@biomejs/cli-win32-x64@2.2.0':
+  '@biomejs/cli-win32-x64@2.4.10':
    optional: true

  '@cspotcode/source-map-support@0.8.1':
@@ -381,6 +381,7 @@ func provisionEnv(
 		"CODER_WORKSPACE_BUILD_ID="+metadata.GetWorkspaceBuildId(),
 		"CODER_TASK_ID="+metadata.GetTaskId(),
 		"CODER_TASK_PROMPT="+metadata.GetTaskPrompt(),
+		"AWS_SDK_UA_APP_ID=APN_1.1/pc_cdfmjwn8i6u8l9fwz8h82e4w3$",
 	)
 	if metadata.GetPrebuiltWorkspaceBuildStage().IsPrebuild() {
 		env = append(env, provider.IsPrebuildEnvironmentVariable()+"=true")
@@ -1298,6 +1298,7 @@ func TestProvision_SafeEnv(t *testing.T) {
 	require.Contains(t, log, passedValue)
 	require.NotContains(t, log, secretValue)
 	require.Contains(t, log, "CODER_")
+	require.Contains(t, log, "AWS_SDK_UA_APP_ID=APN_1.1/pc_cdfmjwn8i6u8l9fwz8h82e4w3$")

 	apply := applyComplete.Type.(*proto.Response_Apply)
 	require.NotEmpty(t, apply.Apply.State, "state exists")
@@ -18,6 +18,7 @@ type SchemaField struct {
 	GoName      string   `json:"go_name"`
 	Type        string   `json:"type"`
 	Description string   `json:"description,omitempty"`
+	Label       string   `json:"label,omitempty"`
 	Required    bool     `json:"required"`
 	Enum        []string `json:"enum,omitempty"`
 	InputType   string   `json:"input_type"`
@@ -135,6 +136,7 @@ func extractFields(t reflect.Type, prefix string, skip map[string]bool) FieldGro

 		typeName := goTypeToSchemaType(f.Type)
 		description := f.Tag.Get("description")
+		label := f.Tag.Get("label")
 		enumTag := f.Tag.Get("enum")

 		var enumValues []string
@@ -150,6 +152,7 @@ func extractFields(t reflect.Type, prefix string, skip map[string]bool) FieldGro
 			GoName:      goFieldPath(prefix, f.Name, t, fullJSONName),
 			Type:        typeName,
 			Description: description,
+			Label:       label,
 			Required:    required,
 			Enum:        enumValues,
 			InputType:   inputType,
@@ -12,162 +12,164 @@ import {
 } from "../helpers";
 import { beforeCoderTest, resetExternalAuthKey } from "../hooks";

-test.describe.skip("externalAuth", () => {
-	test.beforeAll(async ({ baseURL }) => {
-		const srv = await createServer(gitAuth.webPort);
+test.describe
+	.skip("externalAuth", () => {
+		test.beforeAll(async ({ baseURL }) => {
+			const srv = await createServer(gitAuth.webPort);

-		// The GitHub validate endpoint returns the currently authenticated user!
-		srv.use(gitAuth.validatePath, (_req, res) => {
-			res.write(JSON.stringify(ghUser));
-			res.end();
+			// The GitHub validate endpoint returns the currently authenticated user!
+			srv.use(gitAuth.validatePath, (_req, res) => {
+				res.write(JSON.stringify(ghUser));
+				res.end();
+			});
+			srv.use(gitAuth.tokenPath, (_req, res) => {
+				const r = (Math.random() + 1).toString(36).substring(7);
+				res.write(JSON.stringify({ access_token: r }));
+				res.end();
+			});
+			srv.use(gitAuth.authPath, (req, res) => {
+				res.redirect(
+					`${baseURL}/external-auth/${gitAuth.webProvider}/callback?code=1234&state=${req.query.state}`,
+				);
+			});
 		});
-		srv.use(gitAuth.tokenPath, (_req, res) => {
-			const r = (Math.random() + 1).toString(36).substring(7);
-			res.write(JSON.stringify({ access_token: r }));
-			res.end();
+
+		test.beforeEach(async ({ context, page }) => {
+			beforeCoderTest(page);
+			await login(page);
+			await resetExternalAuthKey(context);
 		});
-		srv.use(gitAuth.authPath, (req, res) => {
-			res.redirect(
-				`${baseURL}/external-auth/${gitAuth.webProvider}/callback?code=1234&state=${req.query.state}`,
+
+		// Ensures that a Git auth provider with the device flow functions and completes!
+		test("external auth device", async ({ page }) => {
+			const device: ExternalAuthDevice = {
+				device_code: "1234",
+				user_code: "1234-5678",
+				expires_in: 900,
+				interval: 1,
+				verification_uri: "",
+			};
+
+			// Start a server to mock the GitHub API.
+			const srv = await createServer(gitAuth.devicePort);
+			srv.use(gitAuth.validatePath, (_req, res) => {
+				res.write(JSON.stringify(ghUser));
+				res.end();
+			});
+			srv.use(gitAuth.codePath, (_req, res) => {
+				res.write(JSON.stringify(device));
+				res.end();
+			});
+			srv.use(gitAuth.installationsPath, (_req, res) => {
+				res.write(JSON.stringify(ghInstall));
+				res.end();
+			});
+
+			const token = {
+				access_token: "",
+				error: "authorization_pending",
+				error_description: "",
+			};
+			// First we send a result from the API that the token hasn't been
+			// authorized yet to ensure the UI reacts properly.
+			const sentPending = new Awaiter();
+			srv.use(gitAuth.tokenPath, (_req, res) => {
+				res.write(JSON.stringify(token));
+				res.end();
+				sentPending.done();
+			});
+
+			await page.goto(`/external-auth/${gitAuth.deviceProvider}`, {
+				waitUntil: "domcontentloaded",
+			});
+			await page.getByText(device.user_code).isVisible();
+			await sentPending.wait();
+			// Update the token to be valid and ensure the UI updates!
+			token.error = "";
+			token.access_token = "hello-world";
+			await page.waitForSelector("text=1 organization authorized");
+		});
+
+		test("external auth web", async ({ page }) => {
+			await page.goto(`/external-auth/${gitAuth.webProvider}`, {
+				waitUntil: "domcontentloaded",
+			});
+			// This endpoint doesn't have the installations URL set intentionally!
+			await page.waitForSelector("text=You've authenticated with GitHub!");
+		});
+
+		test("successful external auth from workspace", async ({ page }) => {
+			const templateName = await createTemplate(
+				page,
+				echoResponsesWithExternalAuth([
+					{ id: gitAuth.webProvider, optional: false },
+				]),
 			);
+
+			await createWorkspace(page, templateName, { useExternalAuth: true });
 		});
-	});

-	test.beforeEach(async ({ context, page }) => {
-		beforeCoderTest(page);
-		await login(page);
-		await resetExternalAuthKey(context);
-	});
-
-	// Ensures that a Git auth provider with the device flow functions and completes!
-	test("external auth device", async ({ page }) => {
-		const device: ExternalAuthDevice = {
-			device_code: "1234",
-			user_code: "1234-5678",
-			expires_in: 900,
-			interval: 1,
-			verification_uri: "",
+		const ghUser: Endpoints["GET /user"]["response"]["data"] = {
+			login: "kylecarbs",
+			id: 7122116,
+			node_id: "MDQ6VXNlcjcxMjIxMTY=",
+			avatar_url: "https://avatars.githubusercontent.com/u/7122116?v=4",
+			gravatar_id: "",
+			url: "https://api.github.com/users/kylecarbs",
+			html_url: "https://github.com/kylecarbs",
+			followers_url: "https://api.github.com/users/kylecarbs/followers",
+			following_url:
+				"https://api.github.com/users/kylecarbs/following{/other_user}",
+			gists_url: "https://api.github.com/users/kylecarbs/gists{/gist_id}",
+			starred_url:
+				"https://api.github.com/users/kylecarbs/starred{/owner}{/repo}",
+			subscriptions_url: "https://api.github.com/users/kylecarbs/subscriptions",
+			organizations_url: "https://api.github.com/users/kylecarbs/orgs",
+			repos_url: "https://api.github.com/users/kylecarbs/repos",
+			events_url: "https://api.github.com/users/kylecarbs/events{/privacy}",
+			received_events_url:
+				"https://api.github.com/users/kylecarbs/received_events",
+			type: "User",
+			site_admin: false,
+			name: "Kyle Carberry",
+			company: "@coder",
+			blog: "https://carberry.com",
+			location: "Austin, TX",
+			email: "kyle@carberry.com",
+			hireable: null,
+			bio: "hey there",
+			twitter_username: "kylecarbs",
+			public_repos: 52,
+			public_gists: 9,
+			followers: 208,
+			following: 31,
+			created_at: "2014-04-01T02:24:41Z",
+			updated_at: "2023-06-26T13:03:09Z",
 		};

-		// Start a server to mock the GitHub API.
-		const srv = await createServer(gitAuth.devicePort);
-		srv.use(gitAuth.validatePath, (_req, res) => {
-			res.write(JSON.stringify(ghUser));
-			res.end();
-		});
-		srv.use(gitAuth.codePath, (_req, res) => {
-			res.write(JSON.stringify(device));
-			res.end();
-		});
-		srv.use(gitAuth.installationsPath, (_req, res) => {
-			res.write(JSON.stringify(ghInstall));
-			res.end();
-		});
-
-		const token = {
-			access_token: "",
-			error: "authorization_pending",
-			error_description: "",
-		};
-		// First we send a result from the API that the token hasn't been
-		// authorized yet to ensure the UI reacts properly.
-		const sentPending = new Awaiter();
-		srv.use(gitAuth.tokenPath, (_req, res) => {
-			res.write(JSON.stringify(token));
-			res.end();
-			sentPending.done();
-		});
-
-		await page.goto(`/external-auth/${gitAuth.deviceProvider}`, {
-			waitUntil: "domcontentloaded",
-		});
-		await page.getByText(device.user_code).isVisible();
-		await sentPending.wait();
-		// Update the token to be valid and ensure the UI updates!
-		token.error = "";
-		token.access_token = "hello-world";
-		await page.waitForSelector("text=1 organization authorized");
-	});
-
-	test("external auth web", async ({ page }) => {
-		await page.goto(`/external-auth/${gitAuth.webProvider}`, {
-			waitUntil: "domcontentloaded",
-		});
-		// This endpoint doesn't have the installations URL set intentionally!
-		await page.waitForSelector("text=You've authenticated with GitHub!");
-	});
-
-	test("successful external auth from workspace", async ({ page }) => {
-		const templateName = await createTemplate(
-			page,
-			echoResponsesWithExternalAuth([
-				{ id: gitAuth.webProvider, optional: false },
-			]),
-		);
-
-		await createWorkspace(page, templateName, { useExternalAuth: true });
-	});
-
-	const ghUser: Endpoints["GET /user"]["response"]["data"] = {
-		login: "kylecarbs",
-		id: 7122116,
-		node_id: "MDQ6VXNlcjcxMjIxMTY=",
-		avatar_url: "https://avatars.githubusercontent.com/u/7122116?v=4",
-		gravatar_id: "",
-		url: "https://api.github.com/users/kylecarbs",
-		html_url: "https://github.com/kylecarbs",
-		followers_url: "https://api.github.com/users/kylecarbs/followers",
-		following_url:
-			"https://api.github.com/users/kylecarbs/following{/other_user}",
-		gists_url: "https://api.github.com/users/kylecarbs/gists{/gist_id}",
-		starred_url:
-			"https://api.github.com/users/kylecarbs/starred{/owner}{/repo}",
-		subscriptions_url: "https://api.github.com/users/kylecarbs/subscriptions",
-		organizations_url: "https://api.github.com/users/kylecarbs/orgs",
-		repos_url: "https://api.github.com/users/kylecarbs/repos",
-		events_url: "https://api.github.com/users/kylecarbs/events{/privacy}",
-		received_events_url:
-			"https://api.github.com/users/kylecarbs/received_events",
-		type: "User",
-		site_admin: false,
-		name: "Kyle Carberry",
-		company: "@coder",
-		blog: "https://carberry.com",
-		location: "Austin, TX",
-		email: "kyle@carberry.com",
-		hireable: null,
-		bio: "hey there",
-		twitter_username: "kylecarbs",
-		public_repos: 52,
-		public_gists: 9,
-		followers: 208,
-		following: 31,
-		created_at: "2014-04-01T02:24:41Z",
-		updated_at: "2023-06-26T13:03:09Z",
-	};
-
-	const ghInstall: Endpoints["GET /user/installations"]["response"]["data"] = {
-		installations: [
+		const ghInstall: Endpoints["GET /user/installations"]["response"]["data"] =
 			{
-				id: 1,
-				access_tokens_url: "",
-				account: ghUser,
-				app_id: 1,
-				app_slug: "coder",
-				created_at: "2014-04-01T02:24:41Z",
-				events: [],
-				html_url: "",
-				permissions: {},
-				repositories_url: "",
-				repository_selection: "all",
-				single_file_name: "",
-				suspended_at: null,
-				suspended_by: null,
-				target_id: 1,
-				target_type: "",
-				updated_at: "2023-06-26T13:03:09Z",
-			},
-		],
-		total_count: 1,
-	};
-});
+				installations: [
+					{
+						id: 1,
+						access_tokens_url: "",
+						account: ghUser,
+						app_id: 1,
+						app_slug: "coder",
+						created_at: "2014-04-01T02:24:41Z",
+						events: [],
+						html_url: "",
+						permissions: {},
+						repositories_url: "",
+						repository_selection: "all",
+						single_file_name: "",
+						suspended_at: null,
+						suspended_by: null,
+						target_id: 1,
+						target_type: "",
+						updated_at: "2023-06-26T13:03:09Z",
+					},
+				],
+				total_count: 1,
+			};
+	});
@@ -127,7 +127,7 @@
 	"devDependencies": {
 		"@babel/core": "7.29.0",
 		"@babel/plugin-syntax-typescript": "7.28.6",
-		"@biomejs/biome": "2.2.4",
+		"@biomejs/biome": "2.4.10",
 		"@chromatic-com/storybook": "5.0.1",
 		"@octokit/types": "12.6.0",
 		"@playwright/test": "1.50.1",
@@ -276,8 +276,8 @@ importers:
        specifier: 7.28.6
        version: 7.28.6(@babel/core@7.29.0)
      '@biomejs/biome':
-        specifier: 2.2.4
-        version: 2.2.4
+        specifier: 2.4.10
+        version: 2.4.10
      '@chromatic-com/storybook':
        specifier: 5.0.1
        version: 5.0.1(storybook@10.3.3(@testing-library/dom@10.4.0)(prettier@3.4.1)(react-dom@19.2.2(react@19.2.2))(react@19.2.2))
@@ -469,7 +469,7 @@ importers:
        version: 8.0.2(@emnapi/core@1.7.1)(@emnapi/runtime@1.7.1)(@types/node@20.19.25)(esbuild@0.25.12)(jiti@1.21.7)(yaml@2.7.0)
      vite-plugin-checker:
        specifier: 0.12.0
-        version: 0.12.0(@biomejs/biome@2.2.4)(optionator@0.9.3)(typescript@6.0.2)(vite@8.0.2(@emnapi/core@1.7.1)(@emnapi/runtime@1.7.1)(@types/node@20.19.25)(esbuild@0.25.12)(jiti@1.21.7)(yaml@2.7.0))
+        version: 0.12.0(@biomejs/biome@2.4.10)(optionator@0.9.3)(typescript@6.0.2)(vite@8.0.2(@emnapi/core@1.7.1)(@emnapi/runtime@1.7.1)(@types/node@20.19.25)(esbuild@0.25.12)(jiti@1.21.7)(yaml@2.7.0))
      vitest:
        specifier: 4.1.1
        version: 4.1.1(@types/node@20.19.25)(@vitest/browser-playwright@4.1.1)(jsdom@27.2.0)(msw@2.4.8(typescript@6.0.2))(vite@8.0.2(@emnapi/core@1.7.1)(@emnapi/runtime@1.7.1)(@types/node@20.19.25)(esbuild@0.25.12)(jiti@1.21.7)(yaml@2.7.0))
@@ -708,55 +708,55 @@ packages:
  '@bcoe/v8-coverage@0.2.3':
    resolution: {integrity: sha512-0hYQ8SB4Db5zvZB4axdMHGwEaQjkZzFjQiN9LVYvIFB2nSUHW9tYpxWriPrWDASIxiaXax83REcLxuSdnGPZtw==, tarball: https://registry.npmjs.org/@bcoe/v8-coverage/-/v8-coverage-0.2.3.tgz}

-  '@biomejs/biome@2.2.4':
-    resolution: {integrity: sha512-TBHU5bUy/Ok6m8c0y3pZiuO/BZoY/OcGxoLlrfQof5s8ISVwbVBdFINPQZyFfKwil8XibYWb7JMwnT8wT4WVPg==, tarball: https://registry.npmjs.org/@biomejs/biome/-/biome-2.2.4.tgz}
+  '@biomejs/biome@2.4.10':
+    resolution: {integrity: sha512-xxA3AphFQ1geij4JTHXv4EeSTda1IFn22ye9LdyVPoJU19fNVl0uzfEuhsfQ4Yue/0FaLs2/ccVi4UDiE7R30w==, tarball: https://registry.npmjs.org/@biomejs/biome/-/biome-2.4.10.tgz}
    engines: {node: '>=14.21.3'}
    hasBin: true

-  '@biomejs/cli-darwin-arm64@2.2.4':
-    resolution: {integrity: sha512-RJe2uiyaloN4hne4d2+qVj3d3gFJFbmrr5PYtkkjei1O9c+BjGXgpUPVbi8Pl8syumhzJjFsSIYkcLt2VlVLMA==, tarball: https://registry.npmjs.org/@biomejs/cli-darwin-arm64/-/cli-darwin-arm64-2.2.4.tgz}
+  '@biomejs/cli-darwin-arm64@2.4.10':
+    resolution: {integrity: sha512-vuzzI1cWqDVzOMIkYyHbKqp+AkQq4K7k+UCXWpkYcY/HDn1UxdsbsfgtVpa40shem8Kax4TLDLlx8kMAecgqiw==, tarball: https://registry.npmjs.org/@biomejs/cli-darwin-arm64/-/cli-darwin-arm64-2.4.10.tgz}
    engines: {node: '>=14.21.3'}
    cpu: [arm64]
    os: [darwin]

-  '@biomejs/cli-darwin-x64@2.2.4':
-    resolution: {integrity: sha512-cFsdB4ePanVWfTnPVaUX+yr8qV8ifxjBKMkZwN7gKb20qXPxd/PmwqUH8mY5wnM9+U0QwM76CxFyBRJhC9tQwg==, tarball: https://registry.npmjs.org/@biomejs/cli-darwin-x64/-/cli-darwin-x64-2.2.4.tgz}
+  '@biomejs/cli-darwin-x64@2.4.10':
+    resolution: {integrity: sha512-14fzASRo+BPotwp7nWULy2W5xeUyFnTaq1V13Etrrxkrih+ez/2QfgFm5Ehtf5vSjtgx/IJycMMpn5kPd5ZNaA==, tarball: https://registry.npmjs.org/@biomejs/cli-darwin-x64/-/cli-darwin-x64-2.4.10.tgz}
    engines: {node: '>=14.21.3'}
    cpu: [x64]
    os: [darwin]

-  '@biomejs/cli-linux-arm64-musl@2.2.4':
-    resolution: {integrity: sha512-7TNPkMQEWfjvJDaZRSkDCPT/2r5ESFPKx+TEev+I2BXDGIjfCZk2+b88FOhnJNHtksbOZv8ZWnxrA5gyTYhSsQ==, tarball: https://registry.npmjs.org/@biomejs/cli-linux-arm64-musl/-/cli-linux-arm64-musl-2.2.4.tgz}
+  '@biomejs/cli-linux-arm64-musl@2.4.10':
+    resolution: {integrity: sha512-WrJY6UuiSD/Dh+nwK2qOTu8kdMDlLV3dLMmychIghHPAysWFq1/DGC1pVZx8POE3ZkzKR3PUUnVrtZfMfaJjyQ==, tarball: https://registry.npmjs.org/@biomejs/cli-linux-arm64-musl/-/cli-linux-arm64-musl-2.4.10.tgz}
    engines: {node: '>=14.21.3'}
    cpu: [arm64]
    os: [linux]

-  '@biomejs/cli-linux-arm64@2.2.4':
-    resolution: {integrity: sha512-M/Iz48p4NAzMXOuH+tsn5BvG/Jb07KOMTdSVwJpicmhN309BeEyRyQX+n1XDF0JVSlu28+hiTQ2L4rZPvu7nMw==, tarball: https://registry.npmjs.org/@biomejs/cli-linux-arm64/-/cli-linux-arm64-2.2.4.tgz}
+  '@biomejs/cli-linux-arm64@2.4.10':
+    resolution: {integrity: sha512-7MH1CMW5uuxQ/s7FLST63qF8B3Hgu2HRdZ7tA1X1+mk+St4JOuIrqdhIBnnyqeyWJNI+Bww7Es5QZ0wIc1Cmkw==, tarball: https://registry.npmjs.org/@biomejs/cli-linux-arm64/-/cli-linux-arm64-2.4.10.tgz}
    engines: {node: '>=14.21.3'}
    cpu: [arm64]
    os: [linux]

-  '@biomejs/cli-linux-x64-musl@2.2.4':
-    resolution: {integrity: sha512-m41nFDS0ksXK2gwXL6W6yZTYPMH0LughqbsxInSKetoH6morVj43szqKx79Iudkp8WRT5SxSh7qVb8KCUiewGg==, tarball: https://registry.npmjs.org/@biomejs/cli-linux-x64-musl/-/cli-linux-x64-musl-2.2.4.tgz}
+  '@biomejs/cli-linux-x64-musl@2.4.10':
+    resolution: {integrity: sha512-kDTi3pI6PBN6CiczsWYOyP2zk0IJI08EWEQyDMQWW221rPaaEz6FvjLhnU07KMzLv8q3qSuoB93ua6inSQ55Tw==, tarball: https://registry.npmjs.org/@biomejs/cli-linux-x64-musl/-/cli-linux-x64-musl-2.4.10.tgz}
    engines: {node: '>=14.21.3'}
    cpu: [x64]
    os: [linux]

-  '@biomejs/cli-linux-x64@2.2.4':
-    resolution: {integrity: sha512-orr3nnf2Dpb2ssl6aihQtvcKtLySLta4E2UcXdp7+RTa7mfJjBgIsbS0B9GC8gVu0hjOu021aU8b3/I1tn+pVQ==, tarball: https://registry.npmjs.org/@biomejs/cli-linux-x64/-/cli-linux-x64-2.2.4.tgz}
+  '@biomejs/cli-linux-x64@2.4.10':
+    resolution: {integrity: sha512-tZLvEEi2u9Xu1zAqRjTcpIDGVtldigVvzug2fTuPG0ME/g8/mXpRPcNgLB22bGn6FvLJpHHnqLnwliOu8xjYrg==, tarball: https://registry.npmjs.org/@biomejs/cli-linux-x64/-/cli-linux-x64-2.4.10.tgz}
    engines: {node: '>=14.21.3'}
    cpu: [x64]
    os: [linux]

-  '@biomejs/cli-win32-arm64@2.2.4':
-    resolution: {integrity: sha512-NXnfTeKHDFUWfxAefa57DiGmu9VyKi0cDqFpdI+1hJWQjGJhJutHPX0b5m+eXvTKOaf+brU+P0JrQAZMb5yYaQ==, tarball: https://registry.npmjs.org/@biomejs/cli-win32-arm64/-/cli-win32-arm64-2.2.4.tgz}
+  '@biomejs/cli-win32-arm64@2.4.10':
+    resolution: {integrity: sha512-umwQU6qPzH+ISTf/eHyJ/QoQnJs3V9Vpjz2OjZXe9MVBZ7prgGafMy7yYeRGnlmDAn87AKTF3Q6weLoMGpeqdQ==, tarball: https://registry.npmjs.org/@biomejs/cli-win32-arm64/-/cli-win32-arm64-2.4.10.tgz}
    engines: {node: '>=14.21.3'}
    cpu: [arm64]
    os: [win32]

-  '@biomejs/cli-win32-x64@2.2.4':
-    resolution: {integrity: sha512-3Y4V4zVRarVh/B/eSHczR4LYoSVyv3Dfuvm3cWs5w/HScccS0+Wt/lHOcDTRYeHjQmMYVC3rIRWqyN2EI52+zg==, tarball: https://registry.npmjs.org/@biomejs/cli-win32-x64/-/cli-win32-x64-2.2.4.tgz}
+  '@biomejs/cli-win32-x64@2.4.10':
+    resolution: {integrity: sha512-aW/JU5GuyH4uxMrNYpoC2kjaHlyJGLgIa3XkhPEZI0uKhZhJZU8BuEyJmvgzSPQNGozBwWjC972RaNdcJ9KyJg==, tarball: https://registry.npmjs.org/@biomejs/cli-win32-x64/-/cli-win32-x64-2.4.10.tgz}
    engines: {node: '>=14.21.3'}
    cpu: [x64]
    os: [win32]
@@ -7697,39 +7697,39 @@ snapshots:

  '@bcoe/v8-coverage@0.2.3': {}

-  '@biomejs/biome@2.2.4':
+  '@biomejs/biome@2.4.10':
    optionalDependencies:
-      '@biomejs/cli-darwin-arm64': 2.2.4
-      '@biomejs/cli-darwin-x64': 2.2.4
-      '@biomejs/cli-linux-arm64': 2.2.4
-      '@biomejs/cli-linux-arm64-musl': 2.2.4
-      '@biomejs/cli-linux-x64': 2.2.4
-      '@biomejs/cli-linux-x64-musl': 2.2.4
-      '@biomejs/cli-win32-arm64': 2.2.4
-      '@biomejs/cli-win32-x64': 2.2.4
+      '@biomejs/cli-darwin-arm64': 2.4.10
+      '@biomejs/cli-darwin-x64': 2.4.10
+      '@biomejs/cli-linux-arm64': 2.4.10
+      '@biomejs/cli-linux-arm64-musl': 2.4.10
+      '@biomejs/cli-linux-x64': 2.4.10
+      '@biomejs/cli-linux-x64-musl': 2.4.10
+      '@biomejs/cli-win32-arm64': 2.4.10
+      '@biomejs/cli-win32-x64': 2.4.10

-  '@biomejs/cli-darwin-arm64@2.2.4':
+  '@biomejs/cli-darwin-arm64@2.4.10':
    optional: true

-  '@biomejs/cli-darwin-x64@2.2.4':
+  '@biomejs/cli-darwin-x64@2.4.10':
    optional: true

-  '@biomejs/cli-linux-arm64-musl@2.2.4':
+  '@biomejs/cli-linux-arm64-musl@2.4.10':
    optional: true

-  '@biomejs/cli-linux-arm64@2.2.4':
+  '@biomejs/cli-linux-arm64@2.4.10':
    optional: true

-  '@biomejs/cli-linux-x64-musl@2.2.4':
+  '@biomejs/cli-linux-x64-musl@2.4.10':
    optional: true

-  '@biomejs/cli-linux-x64@2.2.4':
+  '@biomejs/cli-linux-x64@2.4.10':
    optional: true

-  '@biomejs/cli-win32-arm64@2.2.4':
+  '@biomejs/cli-win32-arm64@2.4.10':
    optional: true

-  '@biomejs/cli-win32-x64@2.2.4':
+  '@biomejs/cli-win32-x64@2.4.10':
    optional: true

  '@blazediff/core@1.9.1': {}
@@ -15034,7 +15034,7 @@ snapshots:
      d3-time: 3.1.0
      d3-timer: 3.0.1

-  vite-plugin-checker@0.12.0(@biomejs/biome@2.2.4)(optionator@0.9.3)(typescript@6.0.2)(vite@8.0.2(@emnapi/core@1.7.1)(@emnapi/runtime@1.7.1)(@types/node@20.19.25)(esbuild@0.25.12)(jiti@1.21.7)(yaml@2.7.0)):
+  vite-plugin-checker@0.12.0(@biomejs/biome@2.4.10)(optionator@0.9.3)(typescript@6.0.2)(vite@8.0.2(@emnapi/core@1.7.1)(@emnapi/runtime@1.7.1)(@types/node@20.19.25)(esbuild@0.25.12)(jiti@1.21.7)(yaml@2.7.0)):
    dependencies:
      '@babel/code-frame': 7.29.0
      chokidar: 4.0.3
@@ -15046,7 +15046,7 @@ snapshots:
      vite: 8.0.2(@emnapi/core@1.7.1)(@emnapi/runtime@1.7.1)(@types/node@20.19.25)(esbuild@0.25.12)(jiti@1.21.7)(yaml@2.7.0)
      vscode-uri: 3.1.0
    optionalDependencies:
-      '@biomejs/biome': 2.2.4
+      '@biomejs/biome': 2.4.10
      optionator: 0.9.3
      typescript: 6.0.2

@@ -147,12 +147,9 @@ describe("api.ts", () => {
 				{ q: "owner:me" },
 				"/api/v2/workspaces?q=owner%3Ame",
 			],
-		])(
-			"Workspaces - getURLWithSearchParams(%p, %p) returns %p",
-			(basePath, filter, expected) => {
-				expect(getURLWithSearchParams(basePath, filter)).toBe(expected);
-			},
-		);
+		])("Workspaces - getURLWithSearchParams(%p, %p) returns %p", (basePath, filter, expected) => {
+			expect(getURLWithSearchParams(basePath, filter)).toBe(expected);
+		});
 	});

 	describe("getURLWithSearchParams - users", () => {
@@ -164,12 +161,9 @@ describe("api.ts", () => {
 				"/api/v2/users?q=status%3Aactive",
 			],
 			["/api/v2/users", { q: "" }, "/api/v2/users"],
-		])(
-			"Users - getURLWithSearchParams(%p, %p) returns %p",
-			(basePath, filter, expected) => {
-				expect(getURLWithSearchParams(basePath, filter)).toBe(expected);
-			},
-		);
+		])("Users - getURLWithSearchParams(%p, %p) returns %p", (basePath, filter, expected) => {
+			expect(getURLWithSearchParams(basePath, filter)).toBe(expected);
+		});
 	});

 	describe("update", () => {
@@ -3170,14 +3170,13 @@ class ExperimentalApiMethods {
 		chatId: string,
 		messageId: number,
 		req: TypesGen.EditChatMessageRequest,
-	): Promise<TypesGen.ChatMessage> => {
-		const response = await this.axios.patch<TypesGen.ChatMessage>(
+	): Promise<TypesGen.EditChatMessageResponse> => {
+		const response = await this.axios.patch<TypesGen.EditChatMessageResponse>(
 			`/api/experimental/chats/${chatId}/messages/${messageId}`,
 			req,
 		);
 		return response.data;
 	};
-
 	interruptChat = async (chatId: string): Promise<TypesGen.Chat> => {
 		const response = await this.axios.post<TypesGen.Chat>(
 			`/api/experimental/chats/${chatId}/interrupt`,
@@ -13,6 +13,8 @@ export interface FieldSchema {
 	type: "string" | "integer" | "number" | "boolean" | "array" | "object";
 	/** Human-readable description of the field. May be absent for some fields. */
 	description?: string;
+	/** Optional display label override. When absent, derive from json_name. */
+	label?: string;
 	/** Whether this field is required when configuring the provider. */
 	required: boolean;
 	/** Hint for how the frontend should render the input control. */
@@ -107,6 +107,7 @@
 					"go_name": "Effort",
 					"type": "string",
 					"description": "Controls the level of reasoning effort",
+					"label": "Reasoning Effort",
 					"required": false,
 					"enum": ["low", "medium", "high", "max"],
 					"input_type": "select"
@@ -132,6 +133,7 @@
 					"go_name": "AllowedDomains",
 					"type": "array",
 					"description": "Restrict web search to these domains (cannot be used with blocked_domains)",
+					"label": "Web Search: Allowed Domains",
 					"required": false,
 					"input_type": "json"
 				},
@@ -140,6 +142,7 @@
 					"go_name": "BlockedDomains",
 					"type": "array",
 					"description": "Block web search on these domains (cannot be used with allowed_domains)",
+					"label": "Web Search: Blocked Domains",
 					"required": false,
 					"input_type": "json"
 				}
@@ -286,7 +289,8 @@
 					"type": "string",
 					"description": "Controls whether reasoning tokens are summarized in the response",
 					"required": false,
-					"input_type": "input"
+					"enum": ["auto", "concise", "detailed"],
+					"input_type": "select"
 				},
 				{
 					"json_name": "max_completion_tokens",
@@ -354,7 +358,8 @@
 					"type": "string",
 					"description": "Latency tier to use for processing the request",
 					"required": false,
-					"input_type": "input"
+					"enum": ["auto", "default", "flex", "scale", "priority"],
+					"input_type": "select"
 				},
 				{
 					"json_name": "structured_outputs",
@@ -396,6 +401,7 @@
 					"go_name": "AllowedDomains",
 					"type": "array",
 					"description": "Restrict web search to these domains",
+					"label": "Web Search: Allowed Domains",
 					"required": false,
 					"input_type": "json"
 				}
@@ -913,6 +913,7 @@ export interface AuditLog {
 export interface AuditLogResponse {
 	readonly audit_logs: readonly AuditLog[];
 	readonly count: number;
+	readonly count_cap: number;
 }

 // From codersdk/audit.go
@@ -1200,6 +1201,7 @@ export interface Chat {
 	readonly pin_order: number;
 	readonly mcp_server_ids: readonly string[];
 	readonly labels: Record<string, string>;
+	readonly files?: readonly ChatFileMetadata[];
 	/**
 	 * HasUnread is true when assistant messages exist beyond
 	 * the owner's read cursor, which updates on stream
@@ -1213,8 +1215,14 @@ export interface Chat {
 	 * attach or agent change.
 	 */
 	readonly last_injected_context?: readonly ChatMessagePart[];
+	readonly warnings?: readonly string[];
 }

+// From codersdk/chats.go
+export type ChatBusyBehavior = "interrupt" | "queue";
+
+export const ChatBusyBehaviors: ChatBusyBehavior[] = ["interrupt", "queue"];
+
 // From codersdk/chats.go
 /**
 * ChatCompactionThresholdKeyPrefix scopes per-model chat compaction
@@ -1263,6 +1271,7 @@ export interface ChatCostChatBreakdown {
 	readonly total_output_tokens: number;
 	readonly total_cache_read_tokens: number;
 	readonly total_cache_creation_tokens: number;
+	readonly total_runtime_ms: number;
 }

 // From codersdk/chats.go
@@ -1280,6 +1289,7 @@ export interface ChatCostModelBreakdown {
 	readonly total_output_tokens: number;
 	readonly total_cache_read_tokens: number;
 	readonly total_cache_creation_tokens: number;
+	readonly total_runtime_ms: number;
 }

 // From codersdk/chats.go
@@ -1296,6 +1306,7 @@ export interface ChatCostSummary {
 	readonly total_output_tokens: number;
 	readonly total_cache_read_tokens: number;
 	readonly total_cache_creation_tokens: number;
+	readonly total_runtime_ms: number;
 	readonly by_model: readonly ChatCostModelBreakdown[];
 	readonly by_chat: readonly ChatCostChatBreakdown[];
 	readonly usage_limit?: ChatUsageLimitStatus;
@@ -1326,6 +1337,7 @@ export interface ChatCostUserRollup {
 	readonly total_output_tokens: number;
 	readonly total_cache_read_tokens: number;
 	readonly total_cache_creation_tokens: number;
+	readonly total_runtime_ms: number;
 }

 // From codersdk/chats.go
@@ -1398,6 +1410,20 @@ export interface ChatDiffStatus {
 	readonly stale_at?: string;
 }

+// From codersdk/chats.go
+/**
+ * ChatFileMetadata contains lightweight metadata about a file
+ * associated with a chat, excluding the file content itself.
+ */
+export interface ChatFileMetadata {
+	readonly id: string;
+	readonly owner_id: string;
+	readonly organization_id: string;
+	readonly name: string;
+	readonly mime_type: string;
+	readonly created_at: string;
+}
+
 // From codersdk/chats.go
 export interface ChatFilePart {
 	readonly type: "file";
@@ -1451,21 +1477,14 @@ export interface ChatInputPart {
 	 * The code content from the diff that was commented on.
 	 */
 	readonly content?: string;
-	/**
-	 * The following fields are only set when Type is
-	 * ChatInputPartTypeSkill.
-	 */
-	readonly skill_name?: string;
-	readonly skill_description?: string;
 }

 // From codersdk/chats.go
-export type ChatInputPartType = "file" | "file-reference" | "skill" | "text";
+export type ChatInputPartType = "file" | "file-reference" | "text";

 export const ChatInputPartTypes: ChatInputPartType[] = [
 	"file",
 	"file-reference",
-	"skill",
 	"text",
 ];

@@ -2251,6 +2270,7 @@ export interface ConnectionLog {
 export interface ConnectionLogResponse {
 	readonly connection_logs: readonly ConnectionLog[];
 	readonly count: number;
+	readonly count_cap: number;
 }

 // From codersdk/connectionlog.go
@@ -2341,6 +2361,7 @@ export interface CreateChatMessageRequest {
 	readonly content: readonly ChatInputPart[];
 	readonly model_config_id?: string;
 	readonly mcp_server_ids?: string[];
+	readonly busy_behavior?: ChatBusyBehavior;
 }

 // From codersdk/chats.go
@@ -2351,6 +2372,7 @@ export interface CreateChatMessageResponse {
 	readonly message?: ChatMessage;
 	readonly queued_message?: ChatQueuedMessage;
 	readonly queued: boolean;
+	readonly warnings?: readonly string[];
 }

 // From codersdk/chats.go
@@ -2389,6 +2411,7 @@ export interface CreateChatProviderConfigRequest {
 */
 export interface CreateChatRequest {
 	readonly content: readonly ChatInputPart[];
+	readonly system_prompt?: string;
 	readonly workspace_id?: string;
 	readonly model_config_id?: string;
 	readonly mcp_server_ids?: readonly string[];
@@ -3201,6 +3224,17 @@ export interface EditChatMessageRequest {
 	readonly content: readonly ChatInputPart[];
 }

+// From codersdk/chats.go
+/**
+ * EditChatMessageResponse is the response from editing a message in a chat.
+ * Edits are always synchronous (no queueing), so the message is returned
+ * directly.
+ */
+export interface EditChatMessageResponse {
+	readonly message: ChatMessage;
+	readonly warnings?: readonly string[];
+}
+
 // From codersdk/externalauth.go
 export type EnhancedExternalAuthProvider =
 	| "azure-devops"
@@ -4108,6 +4142,15 @@ export interface MatchedProvisioners {
 	readonly most_recently_seen?: string;
 }

+// From codersdk/chats.go
+/**
+ * MaxChatFileIDs is the maximum number of file IDs that can be
+ * associated with a single chat. This limit prevents unbounded
+ * growth in the chat_file_links table. It is easier to raise
+ * this limit than to lower it.
+ */
+export const MaxChatFileIDs = 20;
+
 // From codersdk/organizations.go
 export interface MinimalOrganization {
 	readonly id: string;
@@ -10,4 +10,4 @@ const CollapsibleTrigger = CollapsiblePrimitive.CollapsibleTrigger;

 const CollapsibleContent = CollapsiblePrimitive.CollapsibleContent;

-export { Collapsible, CollapsibleTrigger, CollapsibleContent };
+export { Collapsible, CollapsibleContent, CollapsibleTrigger };
@@ -12,11 +12,13 @@ import { useClipboard } from "#/hooks/useClipboard";
 type CopyButtonProps = ButtonProps & {
 	text: string;
 	label: string;
+	tooltipSide?: "top" | "bottom" | "left" | "right";
 };

 export const CopyButton: FC<CopyButtonProps> = ({
 	text,
 	label,
+	tooltipSide,
 	...buttonProps
 }) => {
 	const { showCopiedSuccess, copyToClipboard } = useClipboard();
@@ -34,7 +36,7 @@ export const CopyButton: FC<CopyButtonProps> = ({
 					<span className="sr-only">{label}</span>
 				</Button>
 			</TooltipTrigger>
-			<TooltipContent>{label}</TooltipContent>
+			<TooltipContent side={tooltipSide}>{label}</TooltipContent>
 		</Tooltip>
 	);
 };
@@ -67,4 +67,4 @@ export const DialogActionButtons: FC<DialogActionButtonsProps> = ({
 * Re-export of MUI's Dialog component, for convenience.
 * @link See original documentation here: https://mui.com/material-ui/react-dialog/
 */
-export { MuiDialog as Dialog, type DialogProps };
+export { type DialogProps, MuiDialog as Dialog };
@@ -1,8 +1,8 @@
 import { css, type Interpolation, type Theme } from "@emotion/react";
 import CircularProgress from "@mui/material/CircularProgress";
-import IconButton from "@mui/material/IconButton";
 import { CloudUploadIcon, FolderIcon, TrashIcon } from "lucide-react";
 import { type DragEvent, type FC, type ReactNode, useRef } from "react";
+import { Button } from "#/components/Button/Button";
 import { Stack } from "#/components/Stack/Stack";
 import { useClickable } from "#/hooks/useClickable";

@@ -46,9 +46,14 @@ export const FileUpload: FC<FileUploadProps> = ({
 					<span>{file.name}</span>
 				</Stack>

-				<IconButton title={removeLabel} size="small" onClick={onRemove}>
+				<Button
+					variant="subtle"
+					size="icon-lg"
+					onClick={onRemove}
+					title={removeLabel}
+				>
 					<TrashIcon className="size-icon-sm" />
-				</IconButton>
+				</Button>
 			</Stack>
 		);
 	}
--- a/Show More
+++ b/Show More