feat: refactor chatd to use objstore

Signed-off-by: Danny Kopping <danny@coder.com>

.github/cherry-pick-bot.yml

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

.github/workflows/backport.yaml

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

.github/workflows/cherry-pick.yaml

@@ -0,0 +1,143 @@
+# Automatically cherry-pick merged PRs to the latest release branch when the
+# "cherry-pick" label is applied. Works whether the label is added before or
+# after the PR is merged.
+#
+# Usage:
+#   1. Add the "cherry-pick" label to a PR targeting main.
+#   2. When the PR merges (or if already merged), the workflow detects the
+#      latest release/* branch and opens a cherry-pick PR against it.
+#
+# The created PRs follow existing repo conventions:
+#   - Branch:  backport/<pr>-to-<version>
+#   - Title:   <original PR title> (#<pr>)
+#   - Body:    links back to the original PR and merge commit
+
+name: Cherry-pick to release
+on:
+  pull_request_target:
+    branches:
+      - main
+    types:
+      - closed
+      - labeled
+
+permissions:
+  contents: write
+  pull-requests: write
+
+# Prevent duplicate runs for the same PR when both 'closed' and 'labeled'
+# fire in quick succession.
+concurrency:
+  group: cherry-pick-${{ github.event.pull_request.number }}
+
+jobs:
+  cherry-pick:
+    name: Cherry-pick to latest release
+    if: >
+      github.event.pull_request.merged == true &&
+      contains(github.event.pull_request.labels.*.name, 'cherry-pick')
+    runs-on: ubuntu-latest
+    env:
+      PR_NUMBER: ${{ github.event.pull_request.number }}
+      PR_TITLE: ${{ github.event.pull_request.title }}
+      PR_URL: ${{ github.event.pull_request.html_url }}
+      MERGE_SHA: ${{ github.event.pull_request.merge_commit_sha }}
+      SENDER: ${{ github.event.sender.login }}
+    steps:
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+        with:
+          # Full history required for cherry-pick and branch discovery.
+          fetch-depth: 0
+
+      - name: Cherry-pick and open PR
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+        run: |
+          set -euo pipefail
+
+          # Find the latest release branch matching the exact release/2.X
+          # pattern (no suffixes like release/2.31_hotfix).
+          RELEASE_BRANCH=$(
+            git branch -r \
+              | grep -E '^\s*origin/release/2\.[0-9]+$' \
+              | sed 's|.*origin/||' \
+              | sort -t. -k2 -n -r \
+              | head -1
+          )
+
+          if [ -z "$RELEASE_BRANCH" ]; then
+            echo "::error::No release branch found."
+            exit 1
+          fi
+
+          # Strip the release/ prefix for naming.
+          VERSION="${RELEASE_BRANCH#release/}"
+          BACKPORT_BRANCH="backport/${PR_NUMBER}-to-${VERSION}"
+
+          echo "Target branch: $RELEASE_BRANCH"
+          echo "Backport branch: $BACKPORT_BRANCH"
+
+          # Check if backport branch already exists (idempotency for re-runs).
+          if git ls-remote --exit-code origin "refs/heads/${BACKPORT_BRANCH}" >/dev/null 2>&1; then
+            echo "Branch ${BACKPORT_BRANCH} already exists, skipping."
+            exit 0
+          fi
+
+          git config user.name "github-actions[bot]"
+          git config user.email "41898282+github-actions[bot]@users.noreply.github.com"
+
+          # Create the backport branch from the target release branch.
+          git checkout -b "$BACKPORT_BRANCH" "origin/${RELEASE_BRANCH}"
+
+          # Cherry-pick the merge commit. Use -x to record provenance and
+          # -m1 to pick the first parent (the main branch side).
+          CONFLICT=false
+          if ! git cherry-pick -x -m1 "$MERGE_SHA"; then
+            CONFLICT=true
+            echo "::warning::Cherry-pick to ${RELEASE_BRANCH} had conflicts."
+
+            # Abort the failed cherry-pick and create an empty commit with
+            # instructions so the PR can still be opened.
+            git cherry-pick --abort
+            git commit --allow-empty -m "cherry-pick of #${PR_NUMBER} failed — resolve conflicts manually
+
+          Cherry-pick of ${MERGE_SHA} onto ${RELEASE_BRANCH} had conflicts.
+          To resolve:
+            git fetch origin ${BACKPORT_BRANCH}
+            git checkout ${BACKPORT_BRANCH}
+            git cherry-pick -x -m1 ${MERGE_SHA}
+            # resolve conflicts
+            git push origin ${BACKPORT_BRANCH}"
+          fi
+
+          git push origin "$BACKPORT_BRANCH"
+
+          BODY=$(cat <<EOF
+          Cherry-pick of ${PR_URL}
+
+          Original PR: #${PR_NUMBER} — ${PR_TITLE}
+          Merge commit: ${MERGE_SHA}
+          Requested by: @${SENDER}
+          EOF
+          )
+
+          TITLE="${PR_TITLE} (#${PR_NUMBER})"
+          if [ "$CONFLICT" = true ]; then
+            TITLE="[CONFLICT] ${TITLE}"
+          fi
+
+          # Check if a PR already exists for this branch (idempotency
+          # for re-runs). Use --state all to catch closed/merged PRs too.
+          EXISTING_PR=$(gh pr list --head "$BACKPORT_BRANCH" --base "$RELEASE_BRANCH" --state all --json number --jq '.[0].number // empty')
+          if [ -n "$EXISTING_PR" ]; then
+            echo "PR #${EXISTING_PR} already exists for ${BACKPORT_BRANCH}, skipping."
+            exit 0
+          fi
+
+          gh pr create \
+            --base "$RELEASE_BRANCH" \
+            --head "$BACKPORT_BRANCH" \
+            --title "$TITLE" \
+            --body "$BODY" \
+            --assignee "$SENDER" \
+            --reviewer "$SENDER"

.github/workflows/ci.yaml

@@ -35,7 +35,7 @@ jobs:
       tailnet-integration: ${{ steps.filter.outputs.tailnet-integration }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -157,7 +157,7 @@ jobs:
     runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -247,7 +247,7 @@ jobs:
     runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -272,7 +272,7 @@ jobs:
     if: ${{ !cancelled() }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -327,7 +327,7 @@ jobs:
     timeout-minutes: 20
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -379,7 +379,7 @@ jobs:
           - windows-2022
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -575,7 +575,7 @@ jobs:
     timeout-minutes: 25
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -637,7 +637,7 @@ jobs:
     timeout-minutes: 25
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -709,7 +709,7 @@ jobs:
     timeout-minutes: 20
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -736,7 +736,7 @@ jobs:
     timeout-minutes: 20
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -769,7 +769,7 @@ jobs:
     name: ${{ matrix.variant.name }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -849,7 +849,7 @@ jobs:
     if: needs.changes.outputs.site == 'true' || needs.changes.outputs.ci == 'true'
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -930,7 +930,7 @@ jobs:
 
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -1005,7 +1005,7 @@ jobs:
     if: always()
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -1043,7 +1043,7 @@ jobs:
     runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -1097,7 +1097,7 @@ jobs:
       IMAGE: ghcr.io/coder/coder-preview:${{ steps.build-docker.outputs.tag }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -1479,7 +1479,7 @@ jobs:
     if: needs.changes.outputs.db == 'true' || needs.changes.outputs.ci == 'true' || github.ref == 'refs/heads/main'
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 

.github/workflows/dependabot.yaml

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

.github/workflows/deploy.yaml

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

.github/workflows/docker-base.yaml

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

.github/workflows/dogfood.yaml

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

.github/workflows/nightly-gauntlet.yaml

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

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

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

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

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

.github/workflows/pr-cleanup.yaml

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

.github/workflows/pr-deploy.yaml

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

.github/workflows/release-validation.yaml

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

.github/workflows/release.yaml

@@ -81,7 +81,7 @@ jobs:
       version: ${{ steps.version.outputs.version }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -121,22 +121,22 @@ jobs:
           fi
 
           # Derive the release branch from the version tag.
-          # Standard: 2.10.2 -> release/2.10
-          # RC:       2.32.0-rc.0 -> release/2.32-rc.0
+          # Non-RC releases must be on a release/X.Y branch.
+          # RC tags are allowed on any branch (typically main).
           version="$(./scripts/version.sh)"
+          # Strip any pre-release suffix first (e.g. 2.32.0-rc.0 -> 2.32.0)
+          base_version="${version%%-*}"
+          # Then strip patch to get major.minor (e.g. 2.32.0 -> 2.32)
+          release_branch="release/${base_version%.*}"
+
           if [[ "$version" == *-rc.* ]]; then
-            # Extract major.minor and rc suffix from e.g. 2.32.0-rc.0
-            base_version="${version%%-rc.*}"   # 2.32.0
-            major_minor="${base_version%.*}"   # 2.32
-            rc_suffix="${version##*-rc.}"      # 0
-            release_branch="release/${major_minor}-rc.${rc_suffix}"
+            echo "RC release detected — skipping release branch check (RC tags are cut from main)."
           else
-            release_branch=release/${version%.*}
-          fi
-          branch_contains_tag=$(git branch --remotes --contains "${GITHUB_REF}" --list "*/${release_branch}" --format='%(refname)')
-          if [[ -z "${branch_contains_tag}" ]]; then
-            echo "Ref tag must exist in a branch named ${release_branch} when creating a release, did you use scripts/release.sh?"
-            exit 1
+            branch_contains_tag=$(git branch --remotes --contains "${GITHUB_REF}" --list "*/${release_branch}" --format='%(refname)')
+            if [[ -z "${branch_contains_tag}" ]]; then
+              echo "Ref tag must exist in a branch named ${release_branch} when creating a non-RC release, did you use scripts/release.sh?"
+              exit 1
+            fi
           fi
 
           if [[ -z "${CODER_RELEASE_NOTES}" ]]; then
@@ -673,7 +673,7 @@ jobs:
 
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 
@@ -749,7 +749,7 @@ jobs:
 
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@fa2e9d605c4eeb9fcad4c99c224cee0c6c7f3594 # v2.16.0
+        uses: step-security/harden-runner@fe104658747b27e96e4f7e80cd0a94068e53901d # v2.16.1
         with:
           egress-policy: audit
 

.github/workflows/scorecard.yml

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

.github/workflows/security.yaml

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

.github/workflows/stale.yaml

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

.github/workflows/typos.toml

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

.github/workflows/weekly-docs.yaml

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

.gitignore

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

Makefile

@@ -91,6 +91,59 @@ define atomic_write
 		mv "$$tmpfile" "$@" && rm -rf "$$tmpdir"
 endef
 
+# Helper binary targets. Built with go build -o to avoid caching
+# link-stage executables in GOCACHE. Each binary is a real Make
+# target so parallel -j builds serialize correctly instead of
+# racing on the same output path.
+
+_gen/bin/apitypings: $(wildcard scripts/apitypings/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/apitypings
+
+_gen/bin/auditdocgen: $(wildcard scripts/auditdocgen/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/auditdocgen
+
+_gen/bin/check-scopes: $(wildcard scripts/check-scopes/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/check-scopes
+
+_gen/bin/clidocgen: $(wildcard scripts/clidocgen/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/clidocgen
+
+_gen/bin/dbdump: $(wildcard coderd/database/gen/dump/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./coderd/database/gen/dump
+
+_gen/bin/examplegen: $(wildcard scripts/examplegen/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/examplegen
+
+_gen/bin/gensite: $(wildcard scripts/gensite/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/gensite
+
+_gen/bin/apikeyscopesgen: $(wildcard scripts/apikeyscopesgen/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/apikeyscopesgen
+
+_gen/bin/metricsdocgen: $(wildcard scripts/metricsdocgen/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/metricsdocgen
+
+_gen/bin/metricsdocgen-scanner: $(wildcard scripts/metricsdocgen/scanner/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/metricsdocgen/scanner
+
+_gen/bin/modeloptionsgen: $(wildcard scripts/modeloptionsgen/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/modeloptionsgen
+
+_gen/bin/typegen: $(wildcard scripts/typegen/*.go) | _gen
+	@mkdir -p _gen/bin
+	go build -o $@ ./scripts/typegen
+
 # Shared temp directory for atomic writes. Lives at the project root
 # so all targets share the same filesystem, and is gitignored.
 # Order-only prerequisite: recipes that need it depend on | _gen
@@ -201,6 +254,7 @@ endif
 
 clean:
 	rm -rf build/ site/build/ site/out/
+	rm -rf _gen/bin
 	mkdir -p build/
 	git restore site/out/
 .PHONY: clean
@@ -654,8 +708,8 @@ lint/go:
 	go tool github.com/coder/paralleltestctx/cmd/paralleltestctx -custom-funcs="testutil.Context" ./...
 .PHONY: lint/go
 
-lint/examples:
-	go run ./scripts/examplegen/main.go -lint
+lint/examples: | _gen/bin/examplegen
+	_gen/bin/examplegen -lint
 .PHONY: lint/examples
 
 # Use shfmt to determine the shell files, takes editorconfig into consideration.
@@ -693,8 +747,8 @@ lint/actions/zizmor:
 .PHONY: lint/actions/zizmor
 
 # Verify api_key_scope enum contains all RBAC <resource>:<action> values.
-lint/check-scopes: coderd/database/dump.sql
-	go run ./scripts/check-scopes
+lint/check-scopes: coderd/database/dump.sql | _gen/bin/check-scopes
+	_gen/bin/check-scopes
 .PHONY: lint/check-scopes
 
 # Verify migrations do not hardcode the public schema.
@@ -734,8 +788,8 @@ lint/typos: build/typos-$(TYPOS_VERSION)
 # The pre-push hook is allowlisted, see scripts/githooks/pre-push.
 #
 # pre-commit uses two phases: gen+fmt first, then lint+build. This
-# avoids races where gen's `go run` creates temporary .go files that
-# lint's find-based checks pick up. Within each phase, targets run in
+# avoids races where gen creates temporary .go files that lint's
+# find-based checks pick up. Within each phase, targets run in
 # parallel via -j. It fails if any tracked files have unstaged
 # changes afterward.
 
@@ -949,8 +1003,8 @@ gen/mark-fresh:
 
 # Runs migrations to output a dump of the database schema after migrations are
 # applied.
-coderd/database/dump.sql: coderd/database/gen/dump/main.go $(wildcard coderd/database/migrations/*.sql)
-	go run ./coderd/database/gen/dump/main.go
+coderd/database/dump.sql: coderd/database/gen/dump/main.go $(wildcard coderd/database/migrations/*.sql) | _gen/bin/dbdump
+	_gen/bin/dbdump
 	touch "$@"
 
 # Generates Go code for querying the database.
@@ -1067,88 +1121,88 @@ enterprise/aibridged/proto/aibridged.pb.go: enterprise/aibridged/proto/aibridged
 		--go-drpc_opt=paths=source_relative \
 		./enterprise/aibridged/proto/aibridged.proto
 
-site/src/api/typesGenerated.ts: site/node_modules/.installed $(wildcard scripts/apitypings/*) $(shell find ./codersdk $(FIND_EXCLUSIONS) -type f -name '*.go') | _gen
-	$(call atomic_write,go run -C ./scripts/apitypings main.go,./scripts/biome_format.sh)
+site/src/api/typesGenerated.ts: site/node_modules/.installed $(wildcard scripts/apitypings/*) $(shell find ./codersdk $(FIND_EXCLUSIONS) -type f -name '*.go') | _gen _gen/bin/apitypings
+	$(call atomic_write,_gen/bin/apitypings,./scripts/biome_format.sh)
 
 site/e2e/provisionerGenerated.ts: site/node_modules/.installed provisionerd/proto/provisionerd.pb.go provisionersdk/proto/provisioner.pb.go
 	(cd site/ && pnpm run gen:provisioner)
 	touch "$@"
 
-site/src/theme/icons.json: site/node_modules/.installed $(wildcard scripts/gensite/*) $(wildcard site/static/icon/*) | _gen
+site/src/theme/icons.json: site/node_modules/.installed $(wildcard scripts/gensite/*) $(wildcard site/static/icon/*) | _gen _gen/bin/gensite
 	tmpdir=$$(mktemp -d -p _gen) && tmpfile=$$(realpath "$$tmpdir")/$(notdir $@) && \
-		go run ./scripts/gensite/ -icons "$$tmpfile" && \
+		_gen/bin/gensite -icons "$$tmpfile" && \
 		./scripts/biome_format.sh "$$tmpfile" && \
 		mv "$$tmpfile" "$@" && rm -rf "$$tmpdir"
 
-examples/examples.gen.json: scripts/examplegen/main.go examples/examples.go $(shell find ./examples/templates) | _gen
-	$(call atomic_write,go run ./scripts/examplegen/main.go)
+examples/examples.gen.json: scripts/examplegen/main.go examples/examples.go $(shell find ./examples/templates) | _gen _gen/bin/examplegen
+	$(call atomic_write,_gen/bin/examplegen)
 
-coderd/rbac/object_gen.go: scripts/typegen/rbacobject.gotmpl scripts/typegen/main.go coderd/rbac/object.go coderd/rbac/policy/policy.go | _gen
-	$(call atomic_write,go run ./scripts/typegen/main.go rbac object)
+coderd/rbac/object_gen.go: scripts/typegen/rbacobject.gotmpl scripts/typegen/main.go coderd/rbac/object.go coderd/rbac/policy/policy.go | _gen _gen/bin/typegen
+	$(call atomic_write,_gen/bin/typegen rbac object)
 	touch "$@"
 
-# NOTE: depends on object_gen.go because `go run` compiles
-# coderd/rbac which includes it.
+# NOTE: depends on object_gen.go because the generator build
+# compiles coderd/rbac which includes it.
 coderd/rbac/scopes_constants_gen.go: scripts/typegen/scopenames.gotmpl scripts/typegen/main.go coderd/rbac/policy/policy.go \
-	coderd/rbac/object_gen.go | _gen
+	coderd/rbac/object_gen.go | _gen _gen/bin/typegen
 	# Write to a temp file first to avoid truncating the package
 	# during build since the generator imports the rbac package.
-	$(call atomic_write,go run ./scripts/typegen/main.go rbac scopenames)
+	$(call atomic_write,_gen/bin/typegen rbac scopenames)
 	touch "$@"
 
 # NOTE: depends on object_gen.go and scopes_constants_gen.go because
-# `go run` compiles coderd/rbac which includes both.
+# the generator build compiles coderd/rbac which includes both.
 codersdk/rbacresources_gen.go: scripts/typegen/codersdk.gotmpl scripts/typegen/main.go coderd/rbac/object.go coderd/rbac/policy/policy.go \
-	coderd/rbac/object_gen.go coderd/rbac/scopes_constants_gen.go | _gen
+	coderd/rbac/object_gen.go coderd/rbac/scopes_constants_gen.go | _gen _gen/bin/typegen
 	# Write to a temp file to avoid truncating the target, which
 	# would break the codersdk package and any parallel build targets.
-	$(call atomic_write,go run scripts/typegen/main.go rbac codersdk)
+	$(call atomic_write,_gen/bin/typegen rbac codersdk)
 	touch "$@"
 
 # NOTE: depends on object_gen.go and scopes_constants_gen.go because
-# `go run` compiles coderd/rbac which includes both.
+# the generator build compiles coderd/rbac which includes both.
 codersdk/apikey_scopes_gen.go: scripts/apikeyscopesgen/main.go coderd/rbac/scopes_catalog.go coderd/rbac/scopes.go \
-	coderd/rbac/object_gen.go coderd/rbac/scopes_constants_gen.go | _gen
+	coderd/rbac/object_gen.go coderd/rbac/scopes_constants_gen.go | _gen _gen/bin/apikeyscopesgen
 	# Generate SDK constants for external API key scopes.
-	$(call atomic_write,go run ./scripts/apikeyscopesgen)
+	$(call atomic_write,_gen/bin/apikeyscopesgen)
 	touch "$@"
 
 # NOTE: depends on object_gen.go and scopes_constants_gen.go because
-# `go run` compiles coderd/rbac which includes both.
+# the generator build compiles coderd/rbac which includes both.
 site/src/api/rbacresourcesGenerated.ts: site/node_modules/.installed scripts/typegen/codersdk.gotmpl scripts/typegen/main.go coderd/rbac/object.go coderd/rbac/policy/policy.go \
-	coderd/rbac/object_gen.go coderd/rbac/scopes_constants_gen.go | _gen
-	$(call atomic_write,go run scripts/typegen/main.go rbac typescript,./scripts/biome_format.sh)
+	coderd/rbac/object_gen.go coderd/rbac/scopes_constants_gen.go | _gen _gen/bin/typegen
+	$(call atomic_write,_gen/bin/typegen rbac typescript,./scripts/biome_format.sh)
 
-site/src/api/countriesGenerated.ts: site/node_modules/.installed scripts/typegen/countries.tstmpl scripts/typegen/main.go codersdk/countries.go | _gen
-	$(call atomic_write,go run scripts/typegen/main.go countries,./scripts/biome_format.sh)
+site/src/api/countriesGenerated.ts: site/node_modules/.installed scripts/typegen/countries.tstmpl scripts/typegen/main.go codersdk/countries.go | _gen _gen/bin/typegen
+	$(call atomic_write,_gen/bin/typegen countries,./scripts/biome_format.sh)
 
-site/src/api/chatModelOptionsGenerated.json: scripts/modeloptionsgen/main.go codersdk/chats.go | _gen
-	$(call atomic_write,go run ./scripts/modeloptionsgen/main.go | tail -n +2,./scripts/biome_format.sh)
+site/src/api/chatModelOptionsGenerated.json: scripts/modeloptionsgen/main.go codersdk/chats.go | _gen _gen/bin/modeloptionsgen
+	$(call atomic_write,_gen/bin/modeloptionsgen | tail -n +2,./scripts/biome_format.sh)
 
-scripts/metricsdocgen/generated_metrics: $(GO_SRC_FILES) | _gen
-	$(call atomic_write,go run ./scripts/metricsdocgen/scanner)
+scripts/metricsdocgen/generated_metrics: $(GO_SRC_FILES) | _gen _gen/bin/metricsdocgen-scanner
+	$(call atomic_write,_gen/bin/metricsdocgen-scanner)
 
-docs/admin/integrations/prometheus.md: node_modules/.installed scripts/metricsdocgen/main.go scripts/metricsdocgen/metrics scripts/metricsdocgen/generated_metrics | _gen
+docs/admin/integrations/prometheus.md: node_modules/.installed scripts/metricsdocgen/main.go scripts/metricsdocgen/metrics scripts/metricsdocgen/generated_metrics | _gen _gen/bin/metricsdocgen
 	tmpdir=$$(mktemp -d -p _gen) && tmpfile=$$(realpath "$$tmpdir")/$(notdir $@) && cp "$@" "$$tmpfile" && \
-		go run scripts/metricsdocgen/main.go --prometheus-doc-file="$$tmpfile" && \
+		_gen/bin/metricsdocgen --prometheus-doc-file="$$tmpfile" && \
 		pnpm exec markdownlint-cli2 --fix "$$tmpfile" && \
 		pnpm exec markdown-table-formatter "$$tmpfile" && \
 		mv "$$tmpfile" "$@" && rm -rf "$$tmpdir"
 
-docs/reference/cli/index.md: node_modules/.installed scripts/clidocgen/main.go examples/examples.gen.json $(GO_SRC_FILES) | _gen
+docs/reference/cli/index.md: node_modules/.installed scripts/clidocgen/main.go examples/examples.gen.json $(GO_SRC_FILES) | _gen _gen/bin/clidocgen
 	tmpdir=$$(mktemp -d -p _gen) && \
 		tmpdir=$$(realpath "$$tmpdir") && \
 		mkdir -p "$$tmpdir/docs/reference/cli" && \
 		cp docs/manifest.json "$$tmpdir/docs/manifest.json" && \
-		CI=true DOCS_DIR="$$tmpdir/docs" go run ./scripts/clidocgen && \
+		CI=true DOCS_DIR="$$tmpdir/docs" _gen/bin/clidocgen && \
 		pnpm exec markdownlint-cli2 --fix "$$tmpdir/docs/reference/cli/*.md" && \
 		pnpm exec markdown-table-formatter "$$tmpdir/docs/reference/cli/*.md" && \
 		for f in "$$tmpdir/docs/reference/cli/"*.md; do mv "$$f" "docs/reference/cli/$$(basename "$$f")"; done && \
 		rm -rf "$$tmpdir"
 
-docs/admin/security/audit-logs.md: node_modules/.installed coderd/database/querier.go scripts/auditdocgen/main.go enterprise/audit/table.go coderd/rbac/object_gen.go | _gen
+docs/admin/security/audit-logs.md: node_modules/.installed coderd/database/querier.go scripts/auditdocgen/main.go enterprise/audit/table.go coderd/rbac/object_gen.go | _gen _gen/bin/auditdocgen
 	tmpdir=$$(mktemp -d -p _gen) && tmpfile=$$(realpath "$$tmpdir")/$(notdir $@) && cp "$@" "$$tmpfile" && \
-		go run scripts/auditdocgen/main.go --audit-doc-file="$$tmpfile" && \
+		_gen/bin/auditdocgen --audit-doc-file="$$tmpfile" && \
 		pnpm exec markdownlint-cli2 --fix "$$tmpfile" && \
 		pnpm exec markdown-table-formatter "$$tmpfile" && \
 		mv "$$tmpfile" "$@" && rm -rf "$$tmpdir"

agent/agent.go

@@ -102,6 +102,8 @@ type Options struct {
 	ReportMetadataInterval       time.Duration
 	ServiceBannerRefreshInterval time.Duration
 	BlockFileTransfer            bool
+	BlockReversePortForwarding   bool
+	BlockLocalPortForwarding     bool
 	Execer                       agentexec.Execer
 	Devcontainers                bool
 	DevcontainerAPIOptions       []agentcontainers.Option // Enable Devcontainers for these to be effective.
@@ -214,6 +216,8 @@ func New(options Options) Agent {
 		subsystems:                         options.Subsystems,
 		logSender:                          agentsdk.NewLogSender(options.Logger),
 		blockFileTransfer:                  options.BlockFileTransfer,
+		blockReversePortForwarding:         options.BlockReversePortForwarding,
+		blockLocalPortForwarding:           options.BlockLocalPortForwarding,
 
 		prometheusRegistry: prometheusRegistry,
 		metrics:            newAgentMetrics(prometheusRegistry),
@@ -280,6 +284,8 @@ type agent struct {
 	sshServer                          *agentssh.Server
 	sshMaxTimeout                      time.Duration
 	blockFileTransfer                  bool
+	blockReversePortForwarding         bool
+	blockLocalPortForwarding           bool
 
 	lifecycleUpdate            chan struct{}
 	lifecycleReported          chan codersdk.WorkspaceAgentLifecycle
@@ -331,12 +337,14 @@ func (a *agent) TailnetConn() *tailnet.Conn {
 func (a *agent) init() {
 	// pass the "hard" context because we explicitly close the SSH server as part of graceful shutdown.
 	sshSrv, err := agentssh.NewServer(a.hardCtx, a.logger.Named("ssh-server"), a.prometheusRegistry, a.filesystem, a.execer, &agentssh.Config{
-		MaxTimeout:          a.sshMaxTimeout,
-		MOTDFile:            func() string { return a.manifest.Load().MOTDFile },
-		AnnouncementBanners: func() *[]codersdk.BannerConfig { return a.announcementBanners.Load() },
-		UpdateEnv:           a.updateCommandEnv,
-		WorkingDirectory:    func() string { return a.manifest.Load().Directory },
-		BlockFileTransfer:   a.blockFileTransfer,
+		MaxTimeout:                 a.sshMaxTimeout,
+		MOTDFile:                   func() string { return a.manifest.Load().MOTDFile },
+		AnnouncementBanners:        func() *[]codersdk.BannerConfig { return a.announcementBanners.Load() },
+		UpdateEnv:                  a.updateCommandEnv,
+		WorkingDirectory:           func() string { return a.manifest.Load().Directory },
+		BlockFileTransfer:          a.blockFileTransfer,
+		BlockReversePortForwarding: a.blockReversePortForwarding,
+		BlockLocalPortForwarding:   a.blockLocalPortForwarding,
 		ReportConnection: func(id uuid.UUID, magicType agentssh.MagicSessionType, ip string) func(code int, reason string) {
 			var connectionType proto.Connection_Type
 			switch magicType {

agent/agent_test.go

@@ -986,6 +986,161 @@ func TestAgent_TCPRemoteForwarding(t *testing.T) {
 	requireEcho(t, conn)
 }
 
+func TestAgent_TCPLocalForwardingBlocked(t *testing.T) {
+	t.Parallel()
+	ctx := testutil.Context(t, testutil.WaitLong)
+
+	rl, err := net.Listen("tcp", "127.0.0.1:0")
+	require.NoError(t, err)
+	defer rl.Close()
+	tcpAddr, valid := rl.Addr().(*net.TCPAddr)
+	require.True(t, valid)
+	remotePort := tcpAddr.Port
+
+	//nolint:dogsled
+	agentConn, _, _, _, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, o *agent.Options) {
+		o.BlockLocalPortForwarding = true
+	})
+	sshClient, err := agentConn.SSHClient(ctx)
+	require.NoError(t, err)
+	defer sshClient.Close()
+
+	_, err = sshClient.Dial("tcp", fmt.Sprintf("127.0.0.1:%d", remotePort))
+	require.ErrorContains(t, err, "administratively prohibited")
+}
+
+func TestAgent_TCPRemoteForwardingBlocked(t *testing.T) {
+	t.Parallel()
+	ctx := testutil.Context(t, testutil.WaitLong)
+
+	//nolint:dogsled
+	agentConn, _, _, _, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, o *agent.Options) {
+		o.BlockReversePortForwarding = true
+	})
+	sshClient, err := agentConn.SSHClient(ctx)
+	require.NoError(t, err)
+	defer sshClient.Close()
+
+	localhost := netip.MustParseAddr("127.0.0.1")
+	randomPort := testutil.RandomPortNoListen(t)
+	addr := net.TCPAddrFromAddrPort(netip.AddrPortFrom(localhost, randomPort))
+	_, err = sshClient.ListenTCP(addr)
+	require.ErrorContains(t, err, "tcpip-forward request denied by peer")
+}
+
+func TestAgent_UnixLocalForwardingBlocked(t *testing.T) {
+	t.Parallel()
+	if runtime.GOOS == "windows" {
+		t.Skip("unix domain sockets are not fully supported on Windows")
+	}
+	ctx := testutil.Context(t, testutil.WaitLong)
+	tmpdir := testutil.TempDirUnixSocket(t)
+	remoteSocketPath := filepath.Join(tmpdir, "remote-socket")
+
+	l, err := net.Listen("unix", remoteSocketPath)
+	require.NoError(t, err)
+	defer l.Close()
+
+	//nolint:dogsled
+	agentConn, _, _, _, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, o *agent.Options) {
+		o.BlockLocalPortForwarding = true
+	})
+	sshClient, err := agentConn.SSHClient(ctx)
+	require.NoError(t, err)
+	defer sshClient.Close()
+
+	_, err = sshClient.Dial("unix", remoteSocketPath)
+	require.ErrorContains(t, err, "administratively prohibited")
+}
+
+func TestAgent_UnixRemoteForwardingBlocked(t *testing.T) {
+	t.Parallel()
+	if runtime.GOOS == "windows" {
+		t.Skip("unix domain sockets are not fully supported on Windows")
+	}
+	ctx := testutil.Context(t, testutil.WaitLong)
+	tmpdir := testutil.TempDirUnixSocket(t)
+	remoteSocketPath := filepath.Join(tmpdir, "remote-socket")
+
+	//nolint:dogsled
+	agentConn, _, _, _, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, o *agent.Options) {
+		o.BlockReversePortForwarding = true
+	})
+	sshClient, err := agentConn.SSHClient(ctx)
+	require.NoError(t, err)
+	defer sshClient.Close()
+
+	_, err = sshClient.ListenUnix(remoteSocketPath)
+	require.ErrorContains(t, err, "streamlocal-forward@openssh.com request denied by peer")
+}
+
+// TestAgent_LocalBlockedDoesNotAffectReverse verifies that blocking
+// local port forwarding does not prevent reverse port forwarding from
+// working. A field-name transposition at any plumbing hop would cause
+// both directions to be blocked when only one flag is set.
+func TestAgent_LocalBlockedDoesNotAffectReverse(t *testing.T) {
+	t.Parallel()
+	ctx := testutil.Context(t, testutil.WaitLong)
+
+	//nolint:dogsled
+	agentConn, _, _, _, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, o *agent.Options) {
+		o.BlockLocalPortForwarding = true
+	})
+	sshClient, err := agentConn.SSHClient(ctx)
+	require.NoError(t, err)
+	defer sshClient.Close()
+
+	// Reverse forwarding must still work.
+	localhost := netip.MustParseAddr("127.0.0.1")
+	var ll net.Listener
+	for {
+		randomPort := testutil.RandomPortNoListen(t)
+		addr := net.TCPAddrFromAddrPort(netip.AddrPortFrom(localhost, randomPort))
+		ll, err = sshClient.ListenTCP(addr)
+		if err != nil {
+			t.Logf("error remote forwarding: %s", err.Error())
+			select {
+			case <-ctx.Done():
+				t.Fatal("timed out getting random listener")
+			default:
+				continue
+			}
+		}
+		break
+	}
+	_ = ll.Close()
+}
+
+// TestAgent_ReverseBlockedDoesNotAffectLocal verifies that blocking
+// reverse port forwarding does not prevent local port forwarding from
+// working.
+func TestAgent_ReverseBlockedDoesNotAffectLocal(t *testing.T) {
+	t.Parallel()
+	ctx := testutil.Context(t, testutil.WaitLong)
+
+	rl, err := net.Listen("tcp", "127.0.0.1:0")
+	require.NoError(t, err)
+	defer rl.Close()
+	tcpAddr, valid := rl.Addr().(*net.TCPAddr)
+	require.True(t, valid)
+	remotePort := tcpAddr.Port
+	go echoOnce(t, rl)
+
+	//nolint:dogsled
+	agentConn, _, _, _, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, o *agent.Options) {
+		o.BlockReversePortForwarding = true
+	})
+	sshClient, err := agentConn.SSHClient(ctx)
+	require.NoError(t, err)
+	defer sshClient.Close()
+
+	// Local forwarding must still work.
+	conn, err := sshClient.Dial("tcp", fmt.Sprintf("127.0.0.1:%d", remotePort))
+	require.NoError(t, err)
+	defer conn.Close()
+	requireEcho(t, conn)
+}
+
 func TestAgent_UnixLocalForwarding(t *testing.T) {
 	t.Parallel()
 	if runtime.GOOS == "windows" {

agent/agentcontextconfig/api.go

@@ -134,6 +134,33 @@ func Config(workingDir string) (workspacesdk.ContextConfigResponse, []string) {
 	}, ResolvePaths(mcpConfigFile, workingDir)
 }
 
+// ContextPartsFromDir reads instruction files and discovers skills
+// from a specific directory, using default file names. This is used
+// by the CLI chat context commands to read context from an arbitrary
+// directory without consulting agent env vars.
+func ContextPartsFromDir(dir string) []codersdk.ChatMessagePart {
+	var parts []codersdk.ChatMessagePart
+
+	if entry, found := readInstructionFileFromDir(dir, DefaultInstructionsFile); found {
+		parts = append(parts, entry)
+	}
+
+	// Reuse ResolvePaths so CLI skill discovery follows the same
+	// project-relative path handling as agent config resolution.
+	skillParts := discoverSkills(
+		ResolvePaths(strings.Join([]string{DefaultSkillsDir, "skills"}, ","), dir),
+		DefaultSkillMetaFile,
+	)
+	parts = append(parts, skillParts...)
+
+	// Guarantee non-nil slice.
+	if parts == nil {
+		parts = []codersdk.ChatMessagePart{}
+	}
+
+	return parts
+}
+
 // MCPConfigFiles returns the resolved MCP configuration file
 // paths for the agent's MCP manager.
 func (api *API) MCPConfigFiles() []string {

agent/agentcontextconfig/api_test.go

@@ -23,18 +23,144 @@ func filterParts(parts []codersdk.ChatMessagePart, t codersdk.ChatMessagePartTyp
 	return out
 }
 
-func TestConfig(t *testing.T) {
-	t.Run("Defaults", func(t *testing.T) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
+func writeSkillMetaFileInRoot(t *testing.T, skillsRoot, name, description string) string {
+	t.Helper()
 
-		// Clear all env vars so defaults are used.
-		t.Setenv(agentcontextconfig.EnvInstructionsDirs, "")
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
+	skillDir := filepath.Join(skillsRoot, name)
+	require.NoError(t, os.MkdirAll(skillDir, 0o755))
+	require.NoError(t, os.WriteFile(
+		filepath.Join(skillDir, "SKILL.md"),
+		[]byte("---\nname: "+name+"\ndescription: "+description+"\n---\nSkill body"),
+		0o600,
+	))
+
+	return skillDir
+}
+
+func writeSkillMetaFile(t *testing.T, dir, name, description string) string {
+	t.Helper()
+	return writeSkillMetaFileInRoot(t, filepath.Join(dir, ".agents", "skills"), name, description)
+}
+
+func TestContextPartsFromDir(t *testing.T) {
+	t.Parallel()
+
+	t.Run("ReturnsInstructionFilePart", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		instructionPath := filepath.Join(dir, "AGENTS.md")
+		require.NoError(t, os.WriteFile(instructionPath, []byte("project instructions"), 0o600))
+
+		parts := agentcontextconfig.ContextPartsFromDir(dir)
+		contextParts := filterParts(parts, codersdk.ChatMessagePartTypeContextFile)
+		skillParts := filterParts(parts, codersdk.ChatMessagePartTypeSkill)
+
+		require.Len(t, parts, 1)
+		require.Len(t, contextParts, 1)
+		require.Empty(t, skillParts)
+		require.Equal(t, instructionPath, contextParts[0].ContextFilePath)
+		require.Equal(t, "project instructions", contextParts[0].ContextFileContent)
+		require.False(t, contextParts[0].ContextFileTruncated)
+	})
+
+	t.Run("ReturnsSkillParts", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		skillDir := writeSkillMetaFile(t, dir, "my-skill", "A test skill")
+
+		parts := agentcontextconfig.ContextPartsFromDir(dir)
+		contextParts := filterParts(parts, codersdk.ChatMessagePartTypeContextFile)
+		skillParts := filterParts(parts, codersdk.ChatMessagePartTypeSkill)
+
+		require.Len(t, parts, 1)
+		require.Empty(t, contextParts)
+		require.Len(t, skillParts, 1)
+		require.Equal(t, "my-skill", skillParts[0].SkillName)
+		require.Equal(t, "A test skill", skillParts[0].SkillDescription)
+		require.Equal(t, skillDir, skillParts[0].SkillDir)
+		require.Equal(t, "SKILL.md", skillParts[0].ContextFileSkillMetaFile)
+	})
+
+	t.Run("ReturnsSkillPartsFromSkillsDir", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		skillDir := writeSkillMetaFileInRoot(
+			t,
+			filepath.Join(dir, "skills"),
+			"my-skill",
+			"A test skill",
+		)
+
+		parts := agentcontextconfig.ContextPartsFromDir(dir)
+		contextParts := filterParts(parts, codersdk.ChatMessagePartTypeContextFile)
+		skillParts := filterParts(parts, codersdk.ChatMessagePartTypeSkill)
+
+		require.Len(t, parts, 1)
+		require.Empty(t, contextParts)
+		require.Len(t, skillParts, 1)
+		require.Equal(t, "my-skill", skillParts[0].SkillName)
+		require.Equal(t, "A test skill", skillParts[0].SkillDescription)
+		require.Equal(t, skillDir, skillParts[0].SkillDir)
+		require.Equal(t, "SKILL.md", skillParts[0].ContextFileSkillMetaFile)
+	})
+
+	t.Run("ReturnsEmptyForEmptyDir", func(t *testing.T) {
+		t.Parallel()
+
+		parts := agentcontextconfig.ContextPartsFromDir(t.TempDir())
+
+		require.NotNil(t, parts)
+		require.Empty(t, parts)
+	})
+
+	t.Run("ReturnsCombinedResults", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		instructionPath := filepath.Join(dir, "AGENTS.md")
+		require.NoError(t, os.WriteFile(instructionPath, []byte("combined instructions"), 0o600))
+		skillDir := writeSkillMetaFile(t, dir, "combined-skill", "Combined test skill")
+
+		parts := agentcontextconfig.ContextPartsFromDir(dir)
+		contextParts := filterParts(parts, codersdk.ChatMessagePartTypeContextFile)
+		skillParts := filterParts(parts, codersdk.ChatMessagePartTypeSkill)
+
+		require.Len(t, parts, 2)
+		require.Len(t, contextParts, 1)
+		require.Len(t, skillParts, 1)
+		require.Equal(t, instructionPath, contextParts[0].ContextFilePath)
+		require.Equal(t, "combined instructions", contextParts[0].ContextFileContent)
+		require.Equal(t, "combined-skill", skillParts[0].SkillName)
+		require.Equal(t, skillDir, skillParts[0].SkillDir)
+	})
+}
+
+func setupConfigTestEnv(t *testing.T, overrides map[string]string) string {
+	t.Helper()
+
+	fakeHome := t.TempDir()
+	t.Setenv("HOME", fakeHome)
+	t.Setenv("USERPROFILE", fakeHome)
+	t.Setenv(agentcontextconfig.EnvInstructionsDirs, "")
+	t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
+	t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
+	t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
+	t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
+
+	for key, value := range overrides {
+		t.Setenv(key, value)
+	}
+
+	return fakeHome
+}
+
+func TestConfig(t *testing.T) {
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
+	t.Run("Defaults", func(t *testing.T) {
+		setupConfigTestEnv(t, nil)
 
 		workDir := platformAbsPath("work")
 		cfg, mcpFiles := agentcontextconfig.Config(workDir)
@@ -46,20 +172,18 @@ func TestConfig(t *testing.T) {
 		require.Equal(t, []string{filepath.Join(workDir, ".mcp.json")}, mcpFiles)
 	})
 
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
 	t.Run("CustomEnvVars", func(t *testing.T) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
-
 		optInstructions := t.TempDir()
 		optSkills := t.TempDir()
 		optMCP := platformAbsPath("opt", "mcp.json")
-
-		t.Setenv(agentcontextconfig.EnvInstructionsDirs, optInstructions)
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "CUSTOM.md")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, optSkills)
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "META.yaml")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, optMCP)
+		setupConfigTestEnv(t, map[string]string{
+			agentcontextconfig.EnvInstructionsDirs: optInstructions,
+			agentcontextconfig.EnvInstructionsFile: "CUSTOM.md",
+			agentcontextconfig.EnvSkillsDirs:       optSkills,
+			agentcontextconfig.EnvSkillMetaFile:    "META.yaml",
+			agentcontextconfig.EnvMCPConfigFiles:   optMCP,
+		})
 
 		// Create files matching the custom names so we can
 		// verify the env vars actually change lookup behavior.
@@ -85,15 +209,12 @@ func TestConfig(t *testing.T) {
 		require.Equal(t, "META.yaml", skillParts[0].ContextFileSkillMetaFile)
 	})
 
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
 	t.Run("WhitespaceInFileNames", func(t *testing.T) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
+		fakeHome := setupConfigTestEnv(t, map[string]string{
+			agentcontextconfig.EnvInstructionsFile: "  CLAUDE.md  ",
+		})
 		t.Setenv(agentcontextconfig.EnvInstructionsDirs, fakeHome)
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "  CLAUDE.md  ")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
 
 		workDir := t.TempDir()
 		// Create a file matching the trimmed name.
@@ -106,19 +227,13 @@ func TestConfig(t *testing.T) {
 		require.Equal(t, "hello", ctxFiles[0].ContextFileContent)
 	})
 
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
 	t.Run("CommaSeparatedDirs", func(t *testing.T) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
-
 		a := t.TempDir()
 		b := t.TempDir()
-
-		t.Setenv(agentcontextconfig.EnvInstructionsDirs, a+","+b)
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
+		setupConfigTestEnv(t, map[string]string{
+			agentcontextconfig.EnvInstructionsDirs: a + "," + b,
+		})
 
 		// Put instruction files in both dirs.
 		require.NoError(t, os.WriteFile(filepath.Join(a, "AGENTS.md"), []byte("from a"), 0o600))
@@ -133,17 +248,10 @@ func TestConfig(t *testing.T) {
 		require.Equal(t, "from b", ctxFiles[1].ContextFileContent)
 	})
 
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
 	t.Run("ReadsInstructionFiles", func(t *testing.T) {
-		t.Setenv(agentcontextconfig.EnvInstructionsDirs, "")
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
-
 		workDir := t.TempDir()
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
+		fakeHome := setupConfigTestEnv(t, nil)
 
 		// Create ~/.coder/AGENTS.md
 		coderDir := filepath.Join(fakeHome, ".coder")
@@ -164,16 +272,9 @@ func TestConfig(t *testing.T) {
 		require.False(t, ctxFiles[0].ContextFileTruncated)
 	})
 
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
 	t.Run("ReadsWorkingDirInstructionFile", func(t *testing.T) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
-		t.Setenv(agentcontextconfig.EnvInstructionsDirs, "")
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
-
+		setupConfigTestEnv(t, nil)
 		workDir := t.TempDir()
 
 		// Create AGENTS.md in the working directory.
@@ -193,16 +294,9 @@ func TestConfig(t *testing.T) {
 		require.Equal(t, filepath.Join(workDir, "AGENTS.md"), ctxFiles[0].ContextFilePath)
 	})
 
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
 	t.Run("TruncatesLargeInstructionFile", func(t *testing.T) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
-		t.Setenv(agentcontextconfig.EnvInstructionsDirs, "")
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
-
+		setupConfigTestEnv(t, nil)
 		workDir := t.TempDir()
 		largeContent := strings.Repeat("a", 64*1024+100)
 		require.NoError(t, os.WriteFile(filepath.Join(workDir, "AGENTS.md"), []byte(largeContent), 0o600))
@@ -215,79 +309,47 @@ func TestConfig(t *testing.T) {
 		require.Len(t, ctxFiles[0].ContextFileContent, 64*1024)
 	})
 
-	t.Run("SanitizesHTMLComments", func(t *testing.T) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
-		t.Setenv(agentcontextconfig.EnvInstructionsDirs, "")
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
+	sanitizationTests := []struct {
+		name     string
+		input    string
+		expected string
+	}{
+		{
+			name:     "SanitizesHTMLComments",
+			input:    "visible\n<!-- hidden -->content",
+			expected: "visible\ncontent",
+		},
+		{
+			name:     "SanitizesInvisibleUnicode",
+			input:    "before\u200bafter",
+			expected: "beforeafter",
+		},
+		{
+			name:     "NormalizesCRLF",
+			input:    "line1\r\nline2\rline3",
+			expected: "line1\nline2\nline3",
+		},
+	}
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
+	for _, tt := range sanitizationTests {
+		t.Run(tt.name, func(t *testing.T) {
+			setupConfigTestEnv(t, nil)
+			workDir := t.TempDir()
+			require.NoError(t, os.WriteFile(
+				filepath.Join(workDir, "AGENTS.md"),
+				[]byte(tt.input),
+				0o600,
+			))
 
-		workDir := t.TempDir()
-		require.NoError(t, os.WriteFile(
-			filepath.Join(workDir, "AGENTS.md"),
-			[]byte("visible\n<!-- hidden -->content"),
-			0o600,
-		))
+			cfg, _ := agentcontextconfig.Config(workDir)
 
-		cfg, _ := agentcontextconfig.Config(workDir)
-
-		ctxFiles := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeContextFile)
-		require.Len(t, ctxFiles, 1)
-		require.Equal(t, "visible\ncontent", ctxFiles[0].ContextFileContent)
-	})
-
-	t.Run("SanitizesInvisibleUnicode", func(t *testing.T) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
-		t.Setenv(agentcontextconfig.EnvInstructionsDirs, "")
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
-
-		workDir := t.TempDir()
-		// U+200B (zero-width space) should be stripped.
-		require.NoError(t, os.WriteFile(
-			filepath.Join(workDir, "AGENTS.md"),
-			[]byte("before\u200bafter"),
-			0o600,
-		))
-
-		cfg, _ := agentcontextconfig.Config(workDir)
-
-		ctxFiles := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeContextFile)
-		require.Len(t, ctxFiles, 1)
-		require.Equal(t, "beforeafter", ctxFiles[0].ContextFileContent)
-	})
-
-	t.Run("NormalizesCRLF", func(t *testing.T) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
-		t.Setenv(agentcontextconfig.EnvInstructionsDirs, "")
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
-
-		workDir := t.TempDir()
-		require.NoError(t, os.WriteFile(
-			filepath.Join(workDir, "AGENTS.md"),
-			[]byte("line1\r\nline2\rline3"),
-			0o600,
-		))
-
-		cfg, _ := agentcontextconfig.Config(workDir)
-
-		ctxFiles := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeContextFile)
-		require.Len(t, ctxFiles, 1)
-		require.Equal(t, "line1\nline2\nline3", ctxFiles[0].ContextFileContent)
-	})
+			ctxFiles := filterParts(cfg.Parts, codersdk.ChatMessagePartTypeContextFile)
+			require.Len(t, ctxFiles, 1)
+			require.Equal(t, tt.expected, ctxFiles[0].ContextFileContent)
+		})
+	}
 
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
 	t.Run("DiscoversSkills", func(t *testing.T) {
 		fakeHome := t.TempDir()
 		t.Setenv("HOME", fakeHome)
@@ -320,17 +382,13 @@ func TestConfig(t *testing.T) {
 		require.Equal(t, "SKILL.md", skillParts[0].ContextFileSkillMetaFile)
 	})
 
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
 	t.Run("SkipsMissingDirs", func(t *testing.T) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
-
 		nonExistent := filepath.Join(t.TempDir(), "does-not-exist")
-		t.Setenv(agentcontextconfig.EnvInstructionsDirs, nonExistent)
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, nonExistent)
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
+		setupConfigTestEnv(t, map[string]string{
+			agentcontextconfig.EnvInstructionsDirs: nonExistent,
+			agentcontextconfig.EnvSkillsDirs:       nonExistent,
+		})
 
 		workDir := t.TempDir()
 		cfg, _ := agentcontextconfig.Config(workDir)
@@ -340,17 +398,13 @@ func TestConfig(t *testing.T) {
 		require.Empty(t, cfg.Parts)
 	})
 
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
 	t.Run("MCPConfigFilesResolvedSeparately", func(t *testing.T) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
-		t.Setenv(agentcontextconfig.EnvInstructionsDirs, fakeHome)
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillsDirs, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-
 		optMCP := platformAbsPath("opt", "custom.json")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, optMCP)
+		fakeHome := setupConfigTestEnv(t, map[string]string{
+			agentcontextconfig.EnvMCPConfigFiles: optMCP,
+		})
+		t.Setenv(agentcontextconfig.EnvInstructionsDirs, fakeHome)
 
 		workDir := t.TempDir()
 		_, mcpFiles := agentcontextconfig.Config(workDir)
@@ -358,14 +412,10 @@ func TestConfig(t *testing.T) {
 		require.Equal(t, []string{optMCP}, mcpFiles)
 	})
 
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
 	t.Run("SkillNameMustMatchDir", func(t *testing.T) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
+		fakeHome := setupConfigTestEnv(t, nil)
 		t.Setenv(agentcontextconfig.EnvInstructionsDirs, fakeHome)
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
 
 		workDir := t.TempDir()
 		skillsDir := filepath.Join(workDir, "skills")
@@ -385,14 +435,10 @@ func TestConfig(t *testing.T) {
 		require.Empty(t, skillParts)
 	})
 
+	//nolint:paralleltest // Uses t.Setenv to mutate process-wide environment.
 	t.Run("DuplicateSkillsFirstWins", func(t *testing.T) {
-		fakeHome := t.TempDir()
-		t.Setenv("HOME", fakeHome)
-		t.Setenv("USERPROFILE", fakeHome)
+		fakeHome := setupConfigTestEnv(t, nil)
 		t.Setenv(agentcontextconfig.EnvInstructionsDirs, fakeHome)
-		t.Setenv(agentcontextconfig.EnvInstructionsFile, "")
-		t.Setenv(agentcontextconfig.EnvSkillMetaFile, "")
-		t.Setenv(agentcontextconfig.EnvMCPConfigFiles, "")
 
 		workDir := t.TempDir()
 		skillsDir1 := filepath.Join(workDir, "skills1")

agent/agentssh/agentssh.go

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

agent/agentssh/forward.go

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

agent/x/agentdesktop/api.go

@@ -5,7 +5,9 @@ import (
 	"encoding/json"
 	"errors"
 	"io"
+	"mime/multipart"
 	"net/http"
+	"net/textproto"
 	"strconv"
 	"sync"
 	"time"
@@ -620,6 +622,11 @@ func (a *API) handleRecordingStop(rw http.ResponseWriter, r *http.Request) {
 		return
 	}
 	defer artifact.Reader.Close()
+	defer func() {
+		if artifact.ThumbnailReader != nil {
+			_ = artifact.ThumbnailReader.Close()
+		}
+	}()
 
 	if artifact.Size > workspacesdk.MaxRecordingSize {
 		a.logger.Warn(ctx, "recording file exceeds maximum size",
@@ -633,10 +640,60 @@ func (a *API) handleRecordingStop(rw http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	rw.Header().Set("Content-Type", "video/mp4")
-	rw.Header().Set("Content-Length", strconv.FormatInt(artifact.Size, 10))
+	// Discard the thumbnail if it exceeds the maximum size.
+	// The server-side consumer also enforces this per-part, but
+	// rejecting it here avoids streaming a large thumbnail over
+	// the wire for nothing.
+	if artifact.ThumbnailReader != nil && artifact.ThumbnailSize > workspacesdk.MaxThumbnailSize {
+		a.logger.Warn(ctx, "thumbnail file exceeds maximum size, omitting",
+			slog.F("recording_id", recordingID),
+			slog.F("size", artifact.ThumbnailSize),
+			slog.F("max_size", workspacesdk.MaxThumbnailSize),
+		)
+		_ = artifact.ThumbnailReader.Close()
+		artifact.ThumbnailReader = nil
+		artifact.ThumbnailSize = 0
+	}
+
+	// The multipart response is best-effort: once WriteHeader(200) is
+	// called, CreatePart failures produce a truncated response without
+	// the closing boundary. The server-side consumer handles this
+	// gracefully, preserving any parts read before the error.
+	mw := multipart.NewWriter(rw)
+	defer mw.Close()
+	rw.Header().Set("Content-Type", "multipart/mixed; boundary="+mw.Boundary())
 	rw.WriteHeader(http.StatusOK)
-	_, _ = io.Copy(rw, artifact.Reader)
+
+	// Part 1: video/mp4 (always present).
+	videoPart, err := mw.CreatePart(textproto.MIMEHeader{
+		"Content-Type": {"video/mp4"},
+	})
+	if err != nil {
+		a.logger.Warn(ctx, "failed to create video multipart part",
+			slog.F("recording_id", recordingID),
+			slog.Error(err))
+		return
+	}
+	if _, err := io.Copy(videoPart, artifact.Reader); err != nil {
+		a.logger.Warn(ctx, "failed to write video multipart part",
+			slog.F("recording_id", recordingID),
+			slog.Error(err))
+		return
+	}
+
+	// Part 2: image/jpeg (present only when thumbnail was extracted).
+	if artifact.ThumbnailReader != nil {
+		thumbPart, err := mw.CreatePart(textproto.MIMEHeader{
+			"Content-Type": {"image/jpeg"},
+		})
+		if err != nil {
+			a.logger.Warn(ctx, "failed to create thumbnail multipart part",
+				slog.F("recording_id", recordingID),
+				slog.Error(err))
+			return
+		}
+		_, _ = io.Copy(thumbPart, artifact.ThumbnailReader)
+	}
 }
 
 // coordFromAction extracts the coordinate pair from a DesktopAction,

agent/x/agentdesktop/api_test.go

@@ -4,12 +4,17 @@ import (
 	"bytes"
 	"context"
 	"encoding/json"
+	"errors"
 	"fmt"
+	"io"
+	"mime"
+	"mime/multipart"
 	"net"
 	"net/http"
 	"net/http/httptest"
 	"os"
 	"slices"
+	"strings"
 	"sync"
 	"testing"
 	"time"
@@ -59,6 +64,8 @@ type fakeDesktop struct {
 	lastKeyDown string
 	lastKeyUp   string
 
+	thumbnailData []byte // if set, StopRecording includes a thumbnail
+
 	// Recording tracking (guarded by recMu).
 	recMu         sync.Mutex
 	recordings    map[string]string // ID → file path
@@ -187,10 +194,15 @@ func (f *fakeDesktop) StopRecording(_ context.Context, recordingID string) (*age
 		_ = file.Close()
 		return nil, err
 	}
-	return &agentdesktop.RecordingArtifact{
+	artifact := &agentdesktop.RecordingArtifact{
 		Reader: file,
 		Size:   info.Size(),
-	}, nil
+	}
+	if f.thumbnailData != nil {
+		artifact.ThumbnailReader = io.NopCloser(bytes.NewReader(f.thumbnailData))
+		artifact.ThumbnailSize = int64(len(f.thumbnailData))
+	}
+	return artifact, nil
 }
 
 func (f *fakeDesktop) RecordActivity() {
@@ -785,8 +797,8 @@ func TestRecordingStartStop(t *testing.T) {
 	req = httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
 	handler.ServeHTTP(rr, req)
 	require.Equal(t, http.StatusOK, rr.Code)
-	assert.Equal(t, "video/mp4", rr.Header().Get("Content-Type"))
-	assert.Equal(t, []byte("fake-mp4-data-"+testRecIDDefault+"-1"), rr.Body.Bytes())
+	parts := parseMultipartParts(t, rr.Header().Get("Content-Type"), rr.Body.Bytes())
+	assert.Equal(t, []byte("fake-mp4-data-"+testRecIDDefault+"-1"), parts["video/mp4"])
 }
 
 func TestRecordingStartFails(t *testing.T) {
@@ -847,8 +859,8 @@ func TestRecordingStartIdempotent(t *testing.T) {
 	req := httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
 	handler.ServeHTTP(rr, req)
 	require.Equal(t, http.StatusOK, rr.Code)
-	assert.Equal(t, "video/mp4", rr.Header().Get("Content-Type"))
-	assert.Equal(t, []byte("fake-mp4-data-"+testRecIDStartIdempotent+"-1"), rr.Body.Bytes())
+	parts := parseMultipartParts(t, rr.Header().Get("Content-Type"), rr.Body.Bytes())
+	assert.Equal(t, []byte("fake-mp4-data-"+testRecIDStartIdempotent+"-1"), parts["video/mp4"])
 }
 
 func TestRecordingStopIdempotent(t *testing.T) {
@@ -872,7 +884,7 @@ func TestRecordingStopIdempotent(t *testing.T) {
 	require.Equal(t, http.StatusOK, rr.Code)
 
 	// Stop twice - both should succeed with identical data.
-	var bodies [2][]byte
+	var videoParts [2][]byte
 	for i := range 2 {
 		body, err := json.Marshal(map[string]string{"recording_id": testRecIDStopIdempotent})
 		require.NoError(t, err)
@@ -880,10 +892,10 @@ func TestRecordingStopIdempotent(t *testing.T) {
 		request := httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(body))
 		handler.ServeHTTP(recorder, request)
 		require.Equal(t, http.StatusOK, recorder.Code)
-		assert.Equal(t, "video/mp4", recorder.Header().Get("Content-Type"))
-		bodies[i] = recorder.Body.Bytes()
+		parts := parseMultipartParts(t, recorder.Header().Get("Content-Type"), recorder.Body.Bytes())
+		videoParts[i] = parts["video/mp4"]
 	}
-	assert.Equal(t, bodies[0], bodies[1])
+	assert.Equal(t, videoParts[0], videoParts[1])
 }
 
 func TestRecordingStopInvalidIDFormat(t *testing.T) {
@@ -1004,8 +1016,8 @@ func TestRecordingMultipleSimultaneous(t *testing.T) {
 		req := httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(body))
 		handler.ServeHTTP(rr, req)
 		require.Equal(t, http.StatusOK, rr.Code)
-		assert.Equal(t, "video/mp4", rr.Header().Get("Content-Type"))
-		assert.Equal(t, expected[id], rr.Body.Bytes())
+		parts := parseMultipartParts(t, rr.Header().Get("Content-Type"), rr.Body.Bytes())
+		assert.Equal(t, expected[id], parts["video/mp4"])
 	}
 }
 
@@ -1112,8 +1124,8 @@ func TestRecordingStartAfterCompleted(t *testing.T) {
 	req = httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
 	handler.ServeHTTP(rr, req)
 	require.Equal(t, http.StatusOK, rr.Code)
-	assert.Equal(t, "video/mp4", rr.Header().Get("Content-Type"))
-	firstData := rr.Body.Bytes()
+	firstParts := parseMultipartParts(t, rr.Header().Get("Content-Type"), rr.Body.Bytes())
+	firstData := firstParts["video/mp4"]
 	require.NotEmpty(t, firstData)
 
 	// Step 3: Start again with the same ID - should succeed
@@ -1128,8 +1140,8 @@ func TestRecordingStartAfterCompleted(t *testing.T) {
 	req = httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
 	handler.ServeHTTP(rr, req)
 	require.Equal(t, http.StatusOK, rr.Code)
-	assert.Equal(t, "video/mp4", rr.Header().Get("Content-Type"))
-	secondData := rr.Body.Bytes()
+	secondParts := parseMultipartParts(t, rr.Header().Get("Content-Type"), rr.Body.Bytes())
+	secondData := secondParts["video/mp4"]
 	require.NotEmpty(t, secondData)
 
 	// The two recordings should have different data because the
@@ -1235,3 +1247,166 @@ func TestRecordingStopCorrupted(t *testing.T) {
 	require.NoError(t, err)
 	assert.Equal(t, "Recording is corrupted.", respStop.Message)
 }
+
+// parseMultipartParts parses a multipart/mixed response and returns
+// a map from Content-Type to body bytes.
+func parseMultipartParts(t *testing.T, contentType string, body []byte) map[string][]byte {
+	t.Helper()
+	_, params, err := mime.ParseMediaType(contentType)
+	require.NoError(t, err, "parse Content-Type")
+	boundary := params["boundary"]
+	require.NotEmpty(t, boundary, "missing boundary")
+	mr := multipart.NewReader(bytes.NewReader(body), boundary)
+	parts := make(map[string][]byte)
+	for {
+		part, err := mr.NextPart()
+		if errors.Is(err, io.EOF) {
+			break
+		}
+		require.NoError(t, err, "unexpected multipart parse error")
+		ct := part.Header.Get("Content-Type")
+		data, readErr := io.ReadAll(part)
+		require.NoError(t, readErr)
+		parts[ct] = data
+	}
+	return parts
+}
+
+func TestHandleRecordingStop_WithThumbnail(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	// Create a fake JPEG header: 0xFF 0xD8 0xFF followed by 509 zero bytes.
+	thumbnail := make([]byte, 512)
+	thumbnail[0] = 0xff
+	thumbnail[1] = 0xd8
+	thumbnail[2] = 0xff
+
+	fake := &fakeDesktop{
+		startCfg:      agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+		thumbnailData: thumbnail,
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	// Start recording.
+	recID := uuid.New().String()
+	startBody, err := json.Marshal(map[string]string{"recording_id": recID})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(startBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Stop recording.
+	stopBody, err := json.Marshal(map[string]string{"recording_id": recID})
+	require.NoError(t, err)
+	rr = httptest.NewRecorder()
+	req = httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Verify multipart response.
+	ct := rr.Header().Get("Content-Type")
+	assert.True(t, strings.HasPrefix(ct, "multipart/mixed"),
+		"expected multipart/mixed Content-Type, got %s", ct)
+
+	parts := parseMultipartParts(t, ct, rr.Body.Bytes())
+	assert.Len(t, parts, 2, "expected exactly 2 parts (video + thumbnail)")
+
+	// The fake writes "fake-mp4-data-<id>-<counter>" as the MP4 content.
+	expectedMP4 := []byte("fake-mp4-data-" + recID + "-1")
+	assert.Equal(t, expectedMP4, parts["video/mp4"])
+	assert.Equal(t, thumbnail, parts["image/jpeg"])
+}
+
+func TestHandleRecordingStop_NoThumbnail(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	fake := &fakeDesktop{
+		startCfg: agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	// Start recording.
+	recID := uuid.New().String()
+	startBody, err := json.Marshal(map[string]string{"recording_id": recID})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(startBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Stop recording.
+	stopBody, err := json.Marshal(map[string]string{"recording_id": recID})
+	require.NoError(t, err)
+	rr = httptest.NewRecorder()
+	req = httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Verify multipart response.
+	ct := rr.Header().Get("Content-Type")
+	assert.True(t, strings.HasPrefix(ct, "multipart/mixed"),
+		"expected multipart/mixed Content-Type, got %s", ct)
+
+	parts := parseMultipartParts(t, ct, rr.Body.Bytes())
+	assert.Len(t, parts, 1, "expected exactly 1 part (video only)")
+
+	expectedMP4 := []byte("fake-mp4-data-" + recID + "-1")
+	assert.Equal(t, expectedMP4, parts["video/mp4"])
+}
+
+func TestHandleRecordingStop_OversizedThumbnail(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	// Create thumbnail data that exceeds MaxThumbnailSize.
+	oversizedThumb := make([]byte, workspacesdk.MaxThumbnailSize+1)
+	oversizedThumb[0] = 0xff
+	oversizedThumb[1] = 0xd8
+	oversizedThumb[2] = 0xff
+
+	fake := &fakeDesktop{
+		startCfg:      agentdesktop.DisplayConfig{Width: 1920, Height: 1080},
+		thumbnailData: oversizedThumb,
+	}
+	api := agentdesktop.NewAPI(logger, fake, nil)
+	defer api.Close()
+
+	handler := api.Routes()
+
+	// Start recording.
+	recID := uuid.New().String()
+	startBody, err := json.Marshal(map[string]string{"recording_id": recID})
+	require.NoError(t, err)
+	rr := httptest.NewRecorder()
+	req := httptest.NewRequest(http.MethodPost, "/recording/start", bytes.NewReader(startBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Stop recording.
+	stopBody, err := json.Marshal(map[string]string{"recording_id": recID})
+	require.NoError(t, err)
+	rr = httptest.NewRecorder()
+	req = httptest.NewRequest(http.MethodPost, "/recording/stop", bytes.NewReader(stopBody))
+	handler.ServeHTTP(rr, req)
+	require.Equal(t, http.StatusOK, rr.Code)
+
+	// Verify multipart response contains only the video part.
+	ct := rr.Header().Get("Content-Type")
+	assert.True(t, strings.HasPrefix(ct, "multipart/mixed"),
+		"expected multipart/mixed Content-Type, got %s", ct)
+
+	parts := parseMultipartParts(t, ct, rr.Body.Bytes())
+	assert.Len(t, parts, 1, "expected exactly 1 part (video only, oversized thumbnail discarded)")
+
+	expectedMP4 := []byte("fake-mp4-data-" + recID + "-1")
+	assert.Equal(t, expectedMP4, parts["video/mp4"])
+}

agent/x/agentdesktop/desktop.go

@@ -105,6 +105,11 @@ type RecordingArtifact struct {
 	Reader io.ReadCloser
 	// Size is the byte length of the MP4 content.
 	Size int64
+	// ThumbnailReader is the JPEG thumbnail. May be nil if no
+	// thumbnail was produced. Callers must close it when done.
+	ThumbnailReader io.ReadCloser
+	// ThumbnailSize is the byte length of the thumbnail.
+	ThumbnailSize int64
 }
 
 // DisplayConfig describes a running desktop session.

agent/x/agentdesktop/portabledesktop.go

@@ -56,6 +56,7 @@ type screenshotOutput struct {
 type recordingProcess struct {
 	cmd        *exec.Cmd
 	filePath   string
+	thumbPath  string
 	stopped    bool
 	killed     bool          // true when the process was SIGKILLed
 	done       chan struct{} // closed when cmd.Wait() returns
@@ -383,13 +384,20 @@ func (p *portableDesktop) StartRecording(ctx context.Context, recordingID string
 			}
 		}
 		// Completed recording - discard old file, start fresh.
-		if err := os.Remove(rec.filePath); err != nil && !os.IsNotExist(err) {
+		if err := os.Remove(rec.filePath); err != nil && !errors.Is(err, os.ErrNotExist) {
 			p.logger.Warn(ctx, "failed to remove old recording file",
 				slog.F("recording_id", recordingID),
 				slog.F("file_path", rec.filePath),
 				slog.Error(err),
 			)
 		}
+		if err := os.Remove(rec.thumbPath); err != nil && !errors.Is(err, os.ErrNotExist) {
+			p.logger.Warn(ctx, "failed to remove old thumbnail file",
+				slog.F("recording_id", recordingID),
+				slog.F("thumbnail_path", rec.thumbPath),
+				slog.Error(err),
+			)
+		}
 		delete(p.recordings, recordingID)
 	}
 
@@ -406,6 +414,7 @@ func (p *portableDesktop) StartRecording(ctx context.Context, recordingID string
 	}
 
 	filePath := filepath.Join(os.TempDir(), "coder-recording-"+recordingID+".mp4")
+	thumbPath := filepath.Join(os.TempDir(), "coder-recording-"+recordingID+".thumb.jpg")
 
 	// Use a background context so the process outlives the HTTP
 	// request that triggered it.
@@ -419,6 +428,7 @@ func (p *portableDesktop) StartRecording(ctx context.Context, recordingID string
 		"--idle-speedup", "20",
 		"--idle-min-duration", "0.35",
 		"--idle-noise-tolerance", "-38dB",
+		"--thumbnail", thumbPath,
 		filePath)
 
 	if err := cmd.Start(); err != nil {
@@ -427,9 +437,10 @@ func (p *portableDesktop) StartRecording(ctx context.Context, recordingID string
 	}
 
 	rec := &recordingProcess{
-		cmd:      cmd,
-		filePath: filePath,
-		done:     make(chan struct{}),
+		cmd:       cmd,
+		filePath:  filePath,
+		thumbPath: thumbPath,
+		done:      make(chan struct{}),
 	}
 	go func() {
 		rec.waitErr = cmd.Wait()
@@ -499,10 +510,35 @@ func (p *portableDesktop) StopRecording(ctx context.Context, recordingID string)
 		_ = f.Close()
 		return nil, xerrors.Errorf("stat recording artifact: %w", err)
 	}
-	return &RecordingArtifact{
+	artifact := &RecordingArtifact{
 		Reader: f,
 		Size:   info.Size(),
-	}, nil
+	}
+	// Attach thumbnail if the subprocess wrote one.
+	thumbFile, err := os.Open(rec.thumbPath)
+	if err != nil {
+		p.logger.Warn(ctx, "thumbnail not available",
+			slog.F("thumbnail_path", rec.thumbPath),
+			slog.Error(err))
+		return artifact, nil
+	}
+	thumbInfo, err := thumbFile.Stat()
+	if err != nil {
+		_ = thumbFile.Close()
+		p.logger.Warn(ctx, "thumbnail stat failed",
+			slog.F("thumbnail_path", rec.thumbPath),
+			slog.Error(err))
+		return artifact, nil
+	}
+	if thumbInfo.Size() == 0 {
+		_ = thumbFile.Close()
+		p.logger.Warn(ctx, "thumbnail file is empty",
+			slog.F("thumbnail_path", rec.thumbPath))
+		return artifact, nil
+	}
+	artifact.ThumbnailReader = thumbFile
+	artifact.ThumbnailSize = thumbInfo.Size()
+	return artifact, nil
 }
 
 // lockedStopRecordingProcess stops a single recording via stopOnce.
@@ -571,18 +607,33 @@ func (p *portableDesktop) lockedCleanStaleRecordings(ctx context.Context) {
 		}
 		info, err := os.Stat(rec.filePath)
 		if err != nil {
-			// File already removed or inaccessible; drop entry.
+			// File already removed or inaccessible; clean up
+			// any leftover thumbnail and drop the entry.
+			if err := os.Remove(rec.thumbPath); err != nil && !errors.Is(err, os.ErrNotExist) {
+				p.logger.Warn(ctx, "failed to remove stale thumbnail file",
+					slog.F("recording_id", id),
+					slog.F("thumbnail_path", rec.thumbPath),
+					slog.Error(err),
+				)
+			}
 			delete(p.recordings, id)
 			continue
 		}
 		if p.clock.Since(info.ModTime()) > time.Hour {
-			if err := os.Remove(rec.filePath); err != nil && !os.IsNotExist(err) {
+			if err := os.Remove(rec.filePath); err != nil && !errors.Is(err, os.ErrNotExist) {
 				p.logger.Warn(ctx, "failed to remove stale recording file",
 					slog.F("recording_id", id),
 					slog.F("file_path", rec.filePath),
 					slog.Error(err),
 				)
 			}
+			if err := os.Remove(rec.thumbPath); err != nil && !errors.Is(err, os.ErrNotExist) {
+				p.logger.Warn(ctx, "failed to remove stale thumbnail file",
+					slog.F("recording_id", id),
+					slog.F("thumbnail_path", rec.thumbPath),
+					slog.Error(err),
+				)
+			}
 			delete(p.recordings, id)
 		}
 	}
@@ -603,13 +654,14 @@ func (p *portableDesktop) Close() error {
 	// Snapshot recording file paths and idle goroutine channels
 	// for cleanup, then clear the map.
 	type recEntry struct {
-		id       string
-		filePath string
-		idleDone chan struct{}
+		id        string
+		filePath  string
+		thumbPath string
+		idleDone  chan struct{}
 	}
 	var allRecs []recEntry
 	for id, rec := range p.recordings {
-		allRecs = append(allRecs, recEntry{id: id, filePath: rec.filePath, idleDone: rec.idleDone})
+		allRecs = append(allRecs, recEntry{id: id, filePath: rec.filePath, thumbPath: rec.thumbPath, idleDone: rec.idleDone})
 		delete(p.recordings, id)
 	}
 	session := p.session
@@ -630,13 +682,20 @@ func (p *portableDesktop) Close() error {
 	go func() {
 		defer close(cleanupDone)
 		for _, entry := range allRecs {
-			if err := os.Remove(entry.filePath); err != nil && !os.IsNotExist(err) {
+			if err := os.Remove(entry.filePath); err != nil && !errors.Is(err, os.ErrNotExist) {
 				p.logger.Warn(context.Background(), "failed to remove recording file on close",
 					slog.F("recording_id", entry.id),
 					slog.F("file_path", entry.filePath),
 					slog.Error(err),
 				)
 			}
+			if err := os.Remove(entry.thumbPath); err != nil && !errors.Is(err, os.ErrNotExist) {
+				p.logger.Warn(context.Background(), "failed to remove thumbnail file on close",
+					slog.F("recording_id", entry.id),
+					slog.F("thumbnail_path", entry.thumbPath),
+					slog.Error(err),
+				)
+			}
 		}
 		if session != nil {
 			session.cancel()

agent/x/agentdesktop/portabledesktop_internal_test.go

@@ -2,6 +2,7 @@ package agentdesktop
 
 import (
 	"context"
+	"io"
 	"os"
 	"os/exec"
 	"path/filepath"
@@ -584,6 +585,7 @@ func TestPortableDesktop_StartRecording(t *testing.T) {
 		joined := strings.Join(cmd, " ")
 		if strings.Contains(joined, "record") && strings.Contains(joined, "coder-recording-"+recID) {
 			found = true
+			assert.Contains(t, joined, "--thumbnail", "record command should include --thumbnail flag")
 			break
 		}
 	}
@@ -666,6 +668,66 @@ func TestPortableDesktop_StopRecording_ReturnsArtifact(t *testing.T) {
 	defer artifact.Reader.Close()
 	assert.Equal(t, int64(len("fake-mp4-data")), artifact.Size)
 
+	// No thumbnail file exists, so ThumbnailReader should be nil.
+	assert.Nil(t, artifact.ThumbnailReader, "ThumbnailReader should be nil when no thumbnail file exists")
+
+	require.NoError(t, pd.Close())
+}
+
+func TestPortableDesktop_StopRecording_WithThumbnail(t *testing.T) {
+	t.Parallel()
+
+	logger := slogtest.Make(t, nil)
+	rec := &recordedExecer{
+		scripts: map[string]string{
+			"record": `trap 'exit 0' INT; sleep 120 & wait`,
+			"up":     `printf '{"vncPort":5901,"geometry":"1920x1080"}\n' && sleep 120`,
+		},
+	}
+
+	clk := quartz.NewReal()
+	pd := &portableDesktop{
+		logger:       logger,
+		execer:       rec,
+		scriptBinDir: t.TempDir(),
+		clock:        clk,
+		binPath:      "portabledesktop",
+		recordings:   make(map[string]*recordingProcess),
+	}
+	pd.lastDesktopActionAt.Store(clk.Now().UnixNano())
+
+	ctx := t.Context()
+	recID := uuid.New().String()
+	err := pd.StartRecording(ctx, recID)
+	require.NoError(t, err)
+
+	// Write a dummy MP4 file at the expected path.
+	filePath := filepath.Join(os.TempDir(), "coder-recording-"+recID+".mp4")
+	require.NoError(t, os.WriteFile(filePath, []byte("fake-mp4-data"), 0o600))
+	t.Cleanup(func() { _ = os.Remove(filePath) })
+
+	// Write a thumbnail file at the expected path.
+	thumbPath := filepath.Join(os.TempDir(), "coder-recording-"+recID+".thumb.jpg")
+	thumbContent := []byte("fake-jpeg-thumbnail")
+	require.NoError(t, os.WriteFile(thumbPath, thumbContent, 0o600))
+	t.Cleanup(func() { _ = os.Remove(thumbPath) })
+
+	artifact, err := pd.StopRecording(ctx, recID)
+	require.NoError(t, err)
+	defer artifact.Reader.Close()
+
+	assert.Equal(t, int64(len("fake-mp4-data")), artifact.Size)
+
+	// Thumbnail should be attached.
+	require.NotNil(t, artifact.ThumbnailReader, "ThumbnailReader should be non-nil when thumbnail file exists")
+	defer artifact.ThumbnailReader.Close()
+	assert.Equal(t, int64(len(thumbContent)), artifact.ThumbnailSize)
+
+	// Read and verify thumbnail content.
+	thumbData, err := io.ReadAll(artifact.ThumbnailReader)
+	require.NoError(t, err)
+	assert.Equal(t, thumbContent, thumbData)
+
 	require.NoError(t, pd.Close())
 }
 

agent/x/agentmcp/manager.go

@@ -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)
 	}

agent/x/agentmcp/manager_internal_test.go

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

biome.jsonc

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

buildinfo/buildinfo.go

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

buildinfo/buildinfo_test.go

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

cli/agent.go

@@ -53,6 +53,8 @@ func workspaceAgent() *serpent.Command {
 		slogJSONPath                   string
 		slogStackdriverPath            string
 		blockFileTransfer              bool
+		blockReversePortForwarding     bool
+		blockLocalPortForwarding       bool
 		agentHeaderCommand             string
 		agentHeader                    []string
 		devcontainers                  bool
@@ -319,10 +321,12 @@ func workspaceAgent() *serpent.Command {
 					SSHMaxTimeout:        sshMaxTimeout,
 					Subsystems:           subsystems,
 
-					PrometheusRegistry: prometheusRegistry,
-					BlockFileTransfer:  blockFileTransfer,
-					Execer:             execer,
-					Devcontainers:      devcontainers,
+					PrometheusRegistry:         prometheusRegistry,
+					BlockFileTransfer:          blockFileTransfer,
+					BlockReversePortForwarding: blockReversePortForwarding,
+					BlockLocalPortForwarding:   blockLocalPortForwarding,
+					Execer:                     execer,
+					Devcontainers:              devcontainers,
 					DevcontainerAPIOptions: []agentcontainers.Option{
 						agentcontainers.WithSubAgentURL(agentAuth.agentURL.String()),
 						agentcontainers.WithProjectDiscovery(devcontainerProjectDiscovery),
@@ -493,6 +497,20 @@ func workspaceAgent() *serpent.Command {
 			Description: fmt.Sprintf("Block file transfer using known applications: %s.", strings.Join(agentssh.BlockedFileTransferCommands, ",")),
 			Value:       serpent.BoolOf(&blockFileTransfer),
 		},
+		{
+			Flag:        "block-reverse-port-forwarding",
+			Default:     "false",
+			Env:         "CODER_AGENT_BLOCK_REVERSE_PORT_FORWARDING",
+			Description: "Block reverse port forwarding through the SSH server (ssh -R).",
+			Value:       serpent.BoolOf(&blockReversePortForwarding),
+		},
+		{
+			Flag:        "block-local-port-forwarding",
+			Default:     "false",
+			Env:         "CODER_AGENT_BLOCK_LOCAL_PORT_FORWARDING",
+			Description: "Block local port forwarding through the SSH server (ssh -L).",
+			Value:       serpent.BoolOf(&blockLocalPortForwarding),
+		},
 		{
 			Flag:        "devcontainers-enable",
 			Default:     "true",

cli/exp_chat.go

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

cli/exp_chat_test.go

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

cli/root.go

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

cli/root_internal_test.go

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

cli/server.go

@@ -79,6 +79,7 @@ import (
 	"github.com/coder/coder/v2/coderd/notifications"
 	"github.com/coder/coder/v2/coderd/notifications/reports"
 	"github.com/coder/coder/v2/coderd/oauthpki"
+	"github.com/coder/coder/v2/coderd/objstore"
 	"github.com/coder/coder/v2/coderd/pproflabel"
 	"github.com/coder/coder/v2/coderd/prometheusmetrics"
 	"github.com/coder/coder/v2/coderd/prometheusmetrics/insights"
@@ -638,12 +639,19 @@ func (r *RootCmd) Server(newAPI func(context.Context, *coderd.Options) (*coderd.
 					vals.WorkspaceHostnameSuffix.String())
 			}
 
+			objStore, err := objstore.FromConfig(ctx, vals.ObjectStore, r.globalConfig)
+			if err != nil {
+				return xerrors.Errorf("initialize object store: %w", err)
+			}
+			defer objStore.Close()
+
 			options := &coderd.Options{
 				AccessURL:                   vals.AccessURL.Value(),
 				AppHostname:                 appHostname,
 				AppHostnameRegex:            appHostnameRegex,
 				Logger:                      logger.Named("coderd"),
 				Database:                    nil,
+				ObjectStore:                 objStore,
 				BaseDERPMap:                 derpMap,
 				Pubsub:                      nil,
 				CacheDir:                    cacheDir,
@@ -1075,7 +1083,7 @@ func (r *RootCmd) Server(newAPI func(context.Context, *coderd.Options) (*coderd.
 			defer shutdownConns()
 
 			// Ensures that old database entries are cleaned up over time!
-			purger := dbpurge.New(ctx, logger.Named("dbpurge"), options.Database, options.DeploymentValues, quartz.NewReal(), options.PrometheusRegistry)
+			purger := dbpurge.New(ctx, logger.Named("dbpurge"), options.Database, options.DeploymentValues, quartz.NewReal(), options.PrometheusRegistry, objStore)
 			defer purger.Close()
 
 			// Updates workspace usage

cli/ssh.go

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

cli/ssh_internal_test.go

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

cli/testdata/coder_agent_--help.golden

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

cli/testdata/coder_server_--help.golden

@@ -773,6 +773,41 @@ OIDC OPTIONS:
           requirement, and can lead to an insecure OIDC configuration. It is not
           recommended to use this flag.
 
+OBJECT STORE OPTIONS: 
+Configure the object storage backend for binary data (chat files, transcripts,
+etc.). Defaults to local filesystem storage.
+
+      --objectstore-backend string, $CODER_OBJECTSTORE_BACKEND (default: local)
+          The storage backend for binary data such as chat files. Valid values:
+          local, s3, gcs.
+
+      --objectstore-gcs-bucket string, $CODER_OBJECTSTORE_GCS_BUCKET
+          GCS bucket name. Required when the backend is "gcs".
+
+      --objectstore-gcs-credentials-file string, $CODER_OBJECTSTORE_GCS_CREDENTIALS_FILE
+          Path to a GCS service account key file. If empty, Application Default
+          Credentials are used.
+
+      --objectstore-gcs-prefix string, $CODER_OBJECTSTORE_GCS_PREFIX
+          Optional key prefix within the GCS bucket.
+
+      --objectstore-local-dir string, $CODER_OBJECTSTORE_LOCAL_DIR
+          Root directory for the local filesystem object store backend. Only
+          used when the backend is "local".
+
+      --objectstore-s3-bucket string, $CODER_OBJECTSTORE_S3_BUCKET
+          S3 bucket name. Required when the backend is "s3".
+
+      --objectstore-s3-endpoint string, $CODER_OBJECTSTORE_S3_ENDPOINT
+          Custom S3-compatible endpoint URL (e.g. for MinIO, R2, Cloudflare).
+          Leave empty for standard AWS S3.
+
+      --objectstore-s3-prefix string, $CODER_OBJECTSTORE_S3_PREFIX
+          Optional key prefix within the S3 bucket.
+
+      --objectstore-s3-region string, $CODER_OBJECTSTORE_S3_REGION
+          AWS region for the S3 bucket.
+
 PROVISIONING OPTIONS: 
 Tune the behavior of the provisioner, which is responsible for creating,
 updating, and deleting workspace resources.

cli/testdata/server-config.yaml.golden

@@ -908,3 +908,37 @@ retention:
   # build are always retained. Set to 0 to disable automatic deletion.
   # (default: 7d, type: duration)
   workspace_agent_logs: 168h0m0s
+# Configure the object storage backend for binary data (chat files, transcripts,
+# etc.). Defaults to local filesystem storage.
+objectStore:
+  # The storage backend for binary data such as chat files. Valid values: local, s3,
+  # gcs.
+  # (default: local, type: string)
+  backend: local
+  # Root directory for the local filesystem object store backend. Only used when the
+  # backend is "local".
+  # (default: <unset>, type: string)
+  local_dir: ""
+  # S3 bucket name. Required when the backend is "s3".
+  # (default: <unset>, type: string)
+  s3_bucket: ""
+  # AWS region for the S3 bucket.
+  # (default: <unset>, type: string)
+  s3_region: ""
+  # Optional key prefix within the S3 bucket.
+  # (default: <unset>, type: string)
+  s3_prefix: ""
+  # Custom S3-compatible endpoint URL (e.g. for MinIO, R2, Cloudflare). Leave empty
+  # for standard AWS S3.
+  # (default: <unset>, type: string)
+  s3_endpoint: ""
+  # GCS bucket name. Required when the backend is "gcs".
+  # (default: <unset>, type: string)
+  gcs_bucket: ""
+  # Optional key prefix within the GCS bucket.
+  # (default: <unset>, type: string)
+  gcs_prefix: ""
+  # Path to a GCS service account key file. If empty, Application Default
+  # Credentials are used.
+  # (default: <unset>, type: string)
+  gcs_credentials_file: ""

cli/usercreate_test.go

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

coderd/agentapi/logs.go

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

coderd/agentapi/logs_test.go

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

coderd/apidoc/docs.go

@@ -1266,6 +1266,68 @@ const docTemplate = `{
                 ]
             }
         },
+        "/experimental/chats/config/retention-days": {
+            "get": {
+                "produces": [
+                    "application/json"
+                ],
+                "tags": [
+                    "Chats"
+                ],
+                "summary": "Get chat retention days",
+                "operationId": "get-chat-retention-days",
+                "responses": {
+                    "200": {
+                        "description": "OK",
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.ChatRetentionDaysResponse"
+                        }
+                    }
+                },
+                "security": [
+                    {
+                        "CoderSessionToken": []
+                    }
+                ],
+                "x-apidocgen": {
+                    "skip": true
+                }
+            },
+            "put": {
+                "consumes": [
+                    "application/json"
+                ],
+                "tags": [
+                    "Chats"
+                ],
+                "summary": "Update chat retention days",
+                "operationId": "update-chat-retention-days",
+                "parameters": [
+                    {
+                        "description": "Request body",
+                        "name": "request",
+                        "in": "body",
+                        "required": true,
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.UpdateChatRetentionDaysRequest"
+                        }
+                    }
+                ],
+                "responses": {
+                    "204": {
+                        "description": "No Content"
+                    }
+                },
+                "security": [
+                    {
+                        "CoderSessionToken": []
+                    }
+                ],
+                "x-apidocgen": {
+                    "skip": true
+                }
+            }
+        },
         "/experimental/watch-all-workspacebuilds": {
             "get": {
                 "produces": [
@@ -9452,6 +9514,212 @@ const docTemplate = `{
                 ]
             }
         },
+        "/users/{user}/secrets": {
+            "get": {
+                "produces": [
+                    "application/json"
+                ],
+                "tags": [
+                    "Secrets"
+                ],
+                "summary": "List user secrets",
+                "operationId": "list-user-secrets",
+                "parameters": [
+                    {
+                        "type": "string",
+                        "description": "User ID, username, or me",
+                        "name": "user",
+                        "in": "path",
+                        "required": true
+                    }
+                ],
+                "responses": {
+                    "200": {
+                        "description": "OK",
+                        "schema": {
+                            "type": "array",
+                            "items": {
+                                "$ref": "#/definitions/codersdk.UserSecret"
+                            }
+                        }
+                    }
+                },
+                "security": [
+                    {
+                        "CoderSessionToken": []
+                    }
+                ]
+            },
+            "post": {
+                "consumes": [
+                    "application/json"
+                ],
+                "produces": [
+                    "application/json"
+                ],
+                "tags": [
+                    "Secrets"
+                ],
+                "summary": "Create a new user secret",
+                "operationId": "create-a-new-user-secret",
+                "parameters": [
+                    {
+                        "type": "string",
+                        "description": "User ID, username, or me",
+                        "name": "user",
+                        "in": "path",
+                        "required": true
+                    },
+                    {
+                        "description": "Create secret request",
+                        "name": "request",
+                        "in": "body",
+                        "required": true,
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.CreateUserSecretRequest"
+                        }
+                    }
+                ],
+                "responses": {
+                    "201": {
+                        "description": "Created",
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.UserSecret"
+                        }
+                    }
+                },
+                "security": [
+                    {
+                        "CoderSessionToken": []
+                    }
+                ]
+            }
+        },
+        "/users/{user}/secrets/{name}": {
+            "get": {
+                "produces": [
+                    "application/json"
+                ],
+                "tags": [
+                    "Secrets"
+                ],
+                "summary": "Get a user secret by name",
+                "operationId": "get-a-user-secret-by-name",
+                "parameters": [
+                    {
+                        "type": "string",
+                        "description": "User ID, username, or me",
+                        "name": "user",
+                        "in": "path",
+                        "required": true
+                    },
+                    {
+                        "type": "string",
+                        "description": "Secret name",
+                        "name": "name",
+                        "in": "path",
+                        "required": true
+                    }
+                ],
+                "responses": {
+                    "200": {
+                        "description": "OK",
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.UserSecret"
+                        }
+                    }
+                },
+                "security": [
+                    {
+                        "CoderSessionToken": []
+                    }
+                ]
+            },
+            "delete": {
+                "tags": [
+                    "Secrets"
+                ],
+                "summary": "Delete a user secret",
+                "operationId": "delete-a-user-secret",
+                "parameters": [
+                    {
+                        "type": "string",
+                        "description": "User ID, username, or me",
+                        "name": "user",
+                        "in": "path",
+                        "required": true
+                    },
+                    {
+                        "type": "string",
+                        "description": "Secret name",
+                        "name": "name",
+                        "in": "path",
+                        "required": true
+                    }
+                ],
+                "responses": {
+                    "204": {
+                        "description": "No Content"
+                    }
+                },
+                "security": [
+                    {
+                        "CoderSessionToken": []
+                    }
+                ]
+            },
+            "patch": {
+                "consumes": [
+                    "application/json"
+                ],
+                "produces": [
+                    "application/json"
+                ],
+                "tags": [
+                    "Secrets"
+                ],
+                "summary": "Update a user secret",
+                "operationId": "update-a-user-secret",
+                "parameters": [
+                    {
+                        "type": "string",
+                        "description": "User ID, username, or me",
+                        "name": "user",
+                        "in": "path",
+                        "required": true
+                    },
+                    {
+                        "type": "string",
+                        "description": "Secret name",
+                        "name": "name",
+                        "in": "path",
+                        "required": true
+                    },
+                    {
+                        "description": "Update secret request",
+                        "name": "request",
+                        "in": "body",
+                        "required": true,
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.UpdateUserSecretRequest"
+                        }
+                    }
+                ],
+                "responses": {
+                    "200": {
+                        "description": "OK",
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.UserSecret"
+                        }
+                    }
+                },
+                "security": [
+                    {
+                        "CoderSessionToken": []
+                    }
+                ]
+            }
+        },
         "/users/{user}/status/activate": {
             "put": {
                 "produces": [
@@ -13177,6 +13445,12 @@ const docTemplate = `{
                         "$ref": "#/definitions/codersdk.AIBridgeAgenticAction"
                     }
                 },
+                "credential_hint": {
+                    "type": "string"
+                },
+                "credential_kind": {
+                    "type": "string"
+                },
                 "ended_at": {
                     "type": "string",
                     "format": "date-time"
@@ -14175,6 +14449,9 @@ const docTemplate = `{
                 },
                 "count": {
                     "type": "integer"
+                },
+                "count_cap": {
+                    "type": "integer"
                 }
             }
         },
@@ -14417,6 +14694,14 @@ const docTemplate = `{
                 }
             }
         },
+        "codersdk.ChatRetentionDaysResponse": {
+            "type": "object",
+            "properties": {
+                "retention_days": {
+                    "type": "integer"
+                }
+            }
+        },
         "codersdk.ConnectionLatency": {
             "type": "object",
             "properties": {
@@ -14496,6 +14781,9 @@ const docTemplate = `{
                 },
                 "count": {
                     "type": "integer"
+                },
+                "count_cap": {
+                    "type": "integer"
                 }
             }
         },
@@ -15066,6 +15354,26 @@ const docTemplate = `{
                 }
             }
         },
+        "codersdk.CreateUserSecretRequest": {
+            "type": "object",
+            "properties": {
+                "description": {
+                    "type": "string"
+                },
+                "env_name": {
+                    "type": "string"
+                },
+                "file_path": {
+                    "type": "string"
+                },
+                "name": {
+                    "type": "string"
+                },
+                "value": {
+                    "type": "string"
+                }
+            }
+        },
         "codersdk.CreateWorkspaceBuildReason": {
             "type": "string",
             "enum": [
@@ -15617,6 +15925,9 @@ const docTemplate = `{
                 "oauth2": {
                     "$ref": "#/definitions/codersdk.OAuth2Config"
                 },
+                "object_store": {
+                    "$ref": "#/definitions/codersdk.ObjectStoreConfig"
+                },
                 "oidc": {
                     "$ref": "#/definitions/codersdk.OIDCConfig"
                 },
@@ -17633,6 +17944,47 @@ const docTemplate = `{
                 }
             }
         },
+        "codersdk.ObjectStoreConfig": {
+            "type": "object",
+            "properties": {
+                "backend": {
+                    "description": "Backend selects the storage backend: \"local\" (default), \"s3\", or \"gcs\".",
+                    "type": "string"
+                },
+                "gcs_bucket": {
+                    "description": "GCSBucket is the GCS bucket name. Required when Backend is \"gcs\".",
+                    "type": "string"
+                },
+                "gcs_credentials_file": {
+                    "description": "GCSCredentialsFile is an optional path to a GCS service account\nkey file. If empty, Application Default Credentials are used.",
+                    "type": "string"
+                },
+                "gcs_prefix": {
+                    "description": "GCSPrefix is an optional key prefix within the GCS bucket.",
+                    "type": "string"
+                },
+                "local_dir": {
+                    "description": "LocalDir is the root directory for the local filesystem backend.\nOnly used when Backend is \"local\". Defaults to \u003cconfig-dir\u003e/objectstore/.",
+                    "type": "string"
+                },
+                "s3_bucket": {
+                    "description": "S3Bucket is the S3 bucket name. Required when Backend is \"s3\".",
+                    "type": "string"
+                },
+                "s3_endpoint": {
+                    "description": "S3Endpoint is a custom S3-compatible endpoint URL (for MinIO, R2, etc.).",
+                    "type": "string"
+                },
+                "s3_prefix": {
+                    "description": "S3Prefix is an optional key prefix within the S3 bucket.",
+                    "type": "string"
+                },
+                "s3_region": {
+                    "description": "S3Region is the AWS region for the S3 bucket.",
+                    "type": "string"
+                }
+            }
+        },
         "codersdk.OptionType": {
             "type": "string",
             "enum": [
@@ -20946,6 +21298,14 @@ const docTemplate = `{
                 }
             }
         },
+        "codersdk.UpdateChatRetentionDaysRequest": {
+            "type": "object",
+            "properties": {
+                "retention_days": {
+                    "type": "integer"
+                }
+            }
+        },
         "codersdk.UpdateCheckResponse": {
             "type": "object",
             "properties": {
@@ -21187,6 +21547,23 @@ const docTemplate = `{
                 }
             }
         },
+        "codersdk.UpdateUserSecretRequest": {
+            "type": "object",
+            "properties": {
+                "description": {
+                    "type": "string"
+                },
+                "env_name": {
+                    "type": "string"
+                },
+                "file_path": {
+                    "type": "string"
+                },
+                "value": {
+                    "type": "string"
+                }
+            }
+        },
         "codersdk.UpdateWorkspaceACL": {
             "type": "object",
             "properties": {
@@ -21642,6 +22019,35 @@ const docTemplate = `{
                 }
             }
         },
+        "codersdk.UserSecret": {
+            "type": "object",
+            "properties": {
+                "created_at": {
+                    "type": "string",
+                    "format": "date-time"
+                },
+                "description": {
+                    "type": "string"
+                },
+                "env_name": {
+                    "type": "string"
+                },
+                "file_path": {
+                    "type": "string"
+                },
+                "id": {
+                    "type": "string",
+                    "format": "uuid"
+                },
+                "name": {
+                    "type": "string"
+                },
+                "updated_at": {
+                    "type": "string",
+                    "format": "date-time"
+                }
+            }
+        },
         "codersdk.UserStatus": {
             "type": "string",
             "enum": [

coderd/apidoc/swagger.json

@@ -1103,6 +1103,60 @@
 				]
 			}
 		},
+		"/experimental/chats/config/retention-days": {
+			"get": {
+				"produces": ["application/json"],
+				"tags": ["Chats"],
+				"summary": "Get chat retention days",
+				"operationId": "get-chat-retention-days",
+				"responses": {
+					"200": {
+						"description": "OK",
+						"schema": {
+							"$ref": "#/definitions/codersdk.ChatRetentionDaysResponse"
+						}
+					}
+				},
+				"security": [
+					{
+						"CoderSessionToken": []
+					}
+				],
+				"x-apidocgen": {
+					"skip": true
+				}
+			},
+			"put": {
+				"consumes": ["application/json"],
+				"tags": ["Chats"],
+				"summary": "Update chat retention days",
+				"operationId": "update-chat-retention-days",
+				"parameters": [
+					{
+						"description": "Request body",
+						"name": "request",
+						"in": "body",
+						"required": true,
+						"schema": {
+							"$ref": "#/definitions/codersdk.UpdateChatRetentionDaysRequest"
+						}
+					}
+				],
+				"responses": {
+					"204": {
+						"description": "No Content"
+					}
+				},
+				"security": [
+					{
+						"CoderSessionToken": []
+					}
+				],
+				"x-apidocgen": {
+					"skip": true
+				}
+			}
+		},
 		"/experimental/watch-all-workspacebuilds": {
 			"get": {
 				"produces": ["application/json"],
@@ -8377,6 +8431,190 @@
 				]
 			}
 		},
+		"/users/{user}/secrets": {
+			"get": {
+				"produces": ["application/json"],
+				"tags": ["Secrets"],
+				"summary": "List user secrets",
+				"operationId": "list-user-secrets",
+				"parameters": [
+					{
+						"type": "string",
+						"description": "User ID, username, or me",
+						"name": "user",
+						"in": "path",
+						"required": true
+					}
+				],
+				"responses": {
+					"200": {
+						"description": "OK",
+						"schema": {
+							"type": "array",
+							"items": {
+								"$ref": "#/definitions/codersdk.UserSecret"
+							}
+						}
+					}
+				},
+				"security": [
+					{
+						"CoderSessionToken": []
+					}
+				]
+			},
+			"post": {
+				"consumes": ["application/json"],
+				"produces": ["application/json"],
+				"tags": ["Secrets"],
+				"summary": "Create a new user secret",
+				"operationId": "create-a-new-user-secret",
+				"parameters": [
+					{
+						"type": "string",
+						"description": "User ID, username, or me",
+						"name": "user",
+						"in": "path",
+						"required": true
+					},
+					{
+						"description": "Create secret request",
+						"name": "request",
+						"in": "body",
+						"required": true,
+						"schema": {
+							"$ref": "#/definitions/codersdk.CreateUserSecretRequest"
+						}
+					}
+				],
+				"responses": {
+					"201": {
+						"description": "Created",
+						"schema": {
+							"$ref": "#/definitions/codersdk.UserSecret"
+						}
+					}
+				},
+				"security": [
+					{
+						"CoderSessionToken": []
+					}
+				]
+			}
+		},
+		"/users/{user}/secrets/{name}": {
+			"get": {
+				"produces": ["application/json"],
+				"tags": ["Secrets"],
+				"summary": "Get a user secret by name",
+				"operationId": "get-a-user-secret-by-name",
+				"parameters": [
+					{
+						"type": "string",
+						"description": "User ID, username, or me",
+						"name": "user",
+						"in": "path",
+						"required": true
+					},
+					{
+						"type": "string",
+						"description": "Secret name",
+						"name": "name",
+						"in": "path",
+						"required": true
+					}
+				],
+				"responses": {
+					"200": {
+						"description": "OK",
+						"schema": {
+							"$ref": "#/definitions/codersdk.UserSecret"
+						}
+					}
+				},
+				"security": [
+					{
+						"CoderSessionToken": []
+					}
+				]
+			},
+			"delete": {
+				"tags": ["Secrets"],
+				"summary": "Delete a user secret",
+				"operationId": "delete-a-user-secret",
+				"parameters": [
+					{
+						"type": "string",
+						"description": "User ID, username, or me",
+						"name": "user",
+						"in": "path",
+						"required": true
+					},
+					{
+						"type": "string",
+						"description": "Secret name",
+						"name": "name",
+						"in": "path",
+						"required": true
+					}
+				],
+				"responses": {
+					"204": {
+						"description": "No Content"
+					}
+				},
+				"security": [
+					{
+						"CoderSessionToken": []
+					}
+				]
+			},
+			"patch": {
+				"consumes": ["application/json"],
+				"produces": ["application/json"],
+				"tags": ["Secrets"],
+				"summary": "Update a user secret",
+				"operationId": "update-a-user-secret",
+				"parameters": [
+					{
+						"type": "string",
+						"description": "User ID, username, or me",
+						"name": "user",
+						"in": "path",
+						"required": true
+					},
+					{
+						"type": "string",
+						"description": "Secret name",
+						"name": "name",
+						"in": "path",
+						"required": true
+					},
+					{
+						"description": "Update secret request",
+						"name": "request",
+						"in": "body",
+						"required": true,
+						"schema": {
+							"$ref": "#/definitions/codersdk.UpdateUserSecretRequest"
+						}
+					}
+				],
+				"responses": {
+					"200": {
+						"description": "OK",
+						"schema": {
+							"$ref": "#/definitions/codersdk.UserSecret"
+						}
+					}
+				},
+				"security": [
+					{
+						"CoderSessionToken": []
+					}
+				]
+			}
+		},
 		"/users/{user}/status/activate": {
 			"put": {
 				"produces": ["application/json"],
@@ -11755,6 +11993,12 @@
 						"$ref": "#/definitions/codersdk.AIBridgeAgenticAction"
 					}
 				},
+				"credential_hint": {
+					"type": "string"
+				},
+				"credential_kind": {
+					"type": "string"
+				},
 				"ended_at": {
 					"type": "string",
 					"format": "date-time"
@@ -12739,6 +12983,9 @@
 				},
 				"count": {
 					"type": "integer"
+				},
+				"count_cap": {
+					"type": "integer"
 				}
 			}
 		},
@@ -12960,6 +13207,14 @@
 				}
 			}
 		},
+		"codersdk.ChatRetentionDaysResponse": {
+			"type": "object",
+			"properties": {
+				"retention_days": {
+					"type": "integer"
+				}
+			}
+		},
 		"codersdk.ConnectionLatency": {
 			"type": "object",
 			"properties": {
@@ -13039,6 +13294,9 @@
 				},
 				"count": {
 					"type": "integer"
+				},
+				"count_cap": {
+					"type": "integer"
 				}
 			}
 		},
@@ -13575,6 +13833,26 @@
 				}
 			}
 		},
+		"codersdk.CreateUserSecretRequest": {
+			"type": "object",
+			"properties": {
+				"description": {
+					"type": "string"
+				},
+				"env_name": {
+					"type": "string"
+				},
+				"file_path": {
+					"type": "string"
+				},
+				"name": {
+					"type": "string"
+				},
+				"value": {
+					"type": "string"
+				}
+			}
+		},
 		"codersdk.CreateWorkspaceBuildReason": {
 			"type": "string",
 			"enum": [
@@ -14114,6 +14392,9 @@
 				"oauth2": {
 					"$ref": "#/definitions/codersdk.OAuth2Config"
 				},
+				"object_store": {
+					"$ref": "#/definitions/codersdk.ObjectStoreConfig"
+				},
 				"oidc": {
 					"$ref": "#/definitions/codersdk.OIDCConfig"
 				},
@@ -16060,6 +16341,47 @@
 				}
 			}
 		},
+		"codersdk.ObjectStoreConfig": {
+			"type": "object",
+			"properties": {
+				"backend": {
+					"description": "Backend selects the storage backend: \"local\" (default), \"s3\", or \"gcs\".",
+					"type": "string"
+				},
+				"gcs_bucket": {
+					"description": "GCSBucket is the GCS bucket name. Required when Backend is \"gcs\".",
+					"type": "string"
+				},
+				"gcs_credentials_file": {
+					"description": "GCSCredentialsFile is an optional path to a GCS service account\nkey file. If empty, Application Default Credentials are used.",
+					"type": "string"
+				},
+				"gcs_prefix": {
+					"description": "GCSPrefix is an optional key prefix within the GCS bucket.",
+					"type": "string"
+				},
+				"local_dir": {
+					"description": "LocalDir is the root directory for the local filesystem backend.\nOnly used when Backend is \"local\". Defaults to \u003cconfig-dir\u003e/objectstore/.",
+					"type": "string"
+				},
+				"s3_bucket": {
+					"description": "S3Bucket is the S3 bucket name. Required when Backend is \"s3\".",
+					"type": "string"
+				},
+				"s3_endpoint": {
+					"description": "S3Endpoint is a custom S3-compatible endpoint URL (for MinIO, R2, etc.).",
+					"type": "string"
+				},
+				"s3_prefix": {
+					"description": "S3Prefix is an optional key prefix within the S3 bucket.",
+					"type": "string"
+				},
+				"s3_region": {
+					"description": "S3Region is the AWS region for the S3 bucket.",
+					"type": "string"
+				}
+			}
+		},
 		"codersdk.OptionType": {
 			"type": "string",
 			"enum": ["string", "number", "bool", "list(string)"],
@@ -19237,6 +19559,14 @@
 				}
 			}
 		},
+		"codersdk.UpdateChatRetentionDaysRequest": {
+			"type": "object",
+			"properties": {
+				"retention_days": {
+					"type": "integer"
+				}
+			}
+		},
 		"codersdk.UpdateCheckResponse": {
 			"type": "object",
 			"properties": {
@@ -19469,6 +19799,23 @@
 				}
 			}
 		},
+		"codersdk.UpdateUserSecretRequest": {
+			"type": "object",
+			"properties": {
+				"description": {
+					"type": "string"
+				},
+				"env_name": {
+					"type": "string"
+				},
+				"file_path": {
+					"type": "string"
+				},
+				"value": {
+					"type": "string"
+				}
+			}
+		},
 		"codersdk.UpdateWorkspaceACL": {
 			"type": "object",
 			"properties": {
@@ -19899,6 +20246,35 @@
 				}
 			}
 		},
+		"codersdk.UserSecret": {
+			"type": "object",
+			"properties": {
+				"created_at": {
+					"type": "string",
+					"format": "date-time"
+				},
+				"description": {
+					"type": "string"
+				},
+				"env_name": {
+					"type": "string"
+				},
+				"file_path": {
+					"type": "string"
+				},
+				"id": {
+					"type": "string",
+					"format": "uuid"
+				},
+				"name": {
+					"type": "string"
+				},
+				"updated_at": {
+					"type": "string",
+					"format": "date-time"
+				}
+			}
+		},
 		"codersdk.UserStatus": {
 			"type": "string",
 			"enum": ["active", "dormant", "suspended"],

coderd/audit.go

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

coderd/coderd.go

@@ -71,6 +71,7 @@ import (
 	"github.com/coder/coder/v2/coderd/metricscache"
 	"github.com/coder/coder/v2/coderd/notifications"
 	"github.com/coder/coder/v2/coderd/oauth2provider"
+	"github.com/coder/coder/v2/coderd/objstore"
 	"github.com/coder/coder/v2/coderd/portsharing"
 	"github.com/coder/coder/v2/coderd/pproflabel"
 	"github.com/coder/coder/v2/coderd/prebuilds"
@@ -158,6 +159,7 @@ type Options struct {
 	AppHostnameRegex *regexp.Regexp
 	Logger           slog.Logger
 	Database         database.Store
+	ObjectStore      objstore.Store
 	Pubsub           pubsub.Pubsub
 	RuntimeConfig    *runtimeconfig.Manager
 
@@ -792,6 +794,7 @@ func New(options *Options) *API {
 			Pubsub:                         options.Pubsub,
 			WebpushDispatcher:              options.WebPushDispatcher,
 			UsageTracker:                   options.WorkspaceUsageTracker,
+			ObjectStore:                    options.ObjectStore,
 		})
 		gitSyncLogger := options.Logger.Named("gitsync")
 		refresher := gitsync.NewRefresher(
@@ -1189,6 +1192,8 @@ func New(options *Options) *API {
 				r.Delete("/user-compaction-thresholds/{modelConfig}", api.deleteUserChatCompactionThreshold)
 				r.Get("/workspace-ttl", api.getChatWorkspaceTTL)
 				r.Put("/workspace-ttl", api.putChatWorkspaceTTL)
+				r.Get("/retention-days", api.getChatRetentionDays)
+				r.Put("/retention-days", api.putChatRetentionDays)
 				r.Get("/template-allowlist", api.getChatTemplateAllowlist)
 				r.Put("/template-allowlist", api.putChatTemplateAllowlist)
 			})
@@ -1243,6 +1248,7 @@ func New(options *Options) *API {
 					r.Get("/git", api.watchChatGit)
 				})
 				r.Post("/interrupt", api.interruptChat)
+				r.Post("/tool-results", api.postChatToolResults)
 				r.Post("/title/regenerate", api.regenerateChatTitle)
 				r.Get("/diff", api.getChatDiffContents)
 				r.Route("/queue/{queuedMessage}", func(r chi.Router) {
@@ -1605,6 +1611,15 @@ func New(options *Options) *API {
 
 						r.Get("/gitsshkey", api.gitSSHKey)
 						r.Put("/gitsshkey", api.regenerateGitSSHKey)
+						r.Route("/secrets", func(r chi.Router) {
+							r.Post("/", api.postUserSecret)
+							r.Get("/", api.getUserSecrets)
+							r.Route("/{name}", func(r chi.Router) {
+								r.Get("/", api.getUserSecret)
+								r.Patch("/", api.patchUserSecret)
+								r.Delete("/", api.deleteUserSecret)
+							})
+						})
 						r.Route("/notifications", func(r chi.Router) {
 							r.Route("/preferences", func(r chi.Router) {
 								r.Get("/", api.userNotificationPreferences)
@@ -1650,6 +1665,10 @@ func New(options *Options) *API {
 				r.Get("/gitsshkey", api.agentGitSSHKey)
 				r.Post("/log-source", api.workspaceAgentPostLogSource)
 				r.Get("/reinit", api.workspaceAgentReinit)
+				r.Route("/experimental", func(r chi.Router) {
+					r.Post("/chat-context", api.workspaceAgentAddChatContext)
+					r.Delete("/chat-context", api.workspaceAgentClearChatContext)
+				})
 				r.Route("/tasks/{task}", func(r chi.Router) {
 					r.Post("/log-snapshot", api.postWorkspaceAgentTaskLogSnapshot)
 				})

coderd/coderdtest/swaggerparser.go

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

coderd/coderdtest/users.go

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

coderd/database/db2sdk/db2sdk.go

@@ -538,6 +538,12 @@ func WorkspaceAgent(derpMap *tailcfg.DERPMap, coordinator tailnet.Coordinator,
 	switch {
 	case workspaceAgent.Status != codersdk.WorkspaceAgentConnected && workspaceAgent.LifecycleState == codersdk.WorkspaceAgentLifecycleOff:
 		workspaceAgent.Health.Reason = "agent is not running"
+	case workspaceAgent.Status == codersdk.WorkspaceAgentConnecting:
+		// Note: the case above catches connecting+off as "not running".
+		// This case handles connecting agents with a non-off lifecycle
+		// (e.g. "created" or "starting"), where the agent binary has
+		// not yet established a connection to coderd.
+		workspaceAgent.Health.Reason = "agent has not yet connected"
 	case workspaceAgent.Status == codersdk.WorkspaceAgentTimeout:
 		workspaceAgent.Health.Reason = "agent is taking too long to connect"
 	case workspaceAgent.Status == codersdk.WorkspaceAgentDisconnected:
@@ -1234,6 +1240,8 @@ func buildAIBridgeThread(
 	if rootIntc != nil {
 		thread.Model = rootIntc.Model
 		thread.Provider = rootIntc.Provider
+		thread.CredentialKind = string(rootIntc.CredentialKind)
+		thread.CredentialHint = rootIntc.CredentialHint
 		// Get first user prompt from root interception.
 		// A thread can only have one prompt, by definition, since we currently
 		// only store the last prompt observed in an interception.
@@ -1528,7 +1536,10 @@ 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 +1592,19 @@ 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 +1628,9 @@ func ChatRows(rows []database.GetChatsRow, diffStatusesByChatID map[uuid.UUID]da
 	for i, row := range rows {
 		diffStatus, ok := diffStatusesByChatID[row.Chat.ID]
 		if ok {
-			result[i] = Chat(row.Chat, &diffStatus)
+			result[i] = Chat(row.Chat, &diffStatus, nil)
 		} else {
-			result[i] = Chat(row.Chat, nil)
+			result[i] = Chat(row.Chat, nil, nil)
 			if diffStatusesByChatID != nil {
 				emptyDiffStatus := ChatDiffStatus(row.Chat.ID, nil)
 				result[i].DiffStatus = &emptyDiffStatus
@@ -1699,3 +1723,41 @@ func ChatDiffStatus(chatID uuid.UUID, status *database.ChatDiffStatus) codersdk.
 
 	return result
 }
+
+// UserSecret converts a database ListUserSecretsRow (metadata only,
+// no value) to an SDK UserSecret.
+func UserSecret(secret database.ListUserSecretsRow) codersdk.UserSecret {
+	return codersdk.UserSecret{
+		ID:          secret.ID,
+		Name:        secret.Name,
+		Description: secret.Description,
+		EnvName:     secret.EnvName,
+		FilePath:    secret.FilePath,
+		CreatedAt:   secret.CreatedAt,
+		UpdatedAt:   secret.UpdatedAt,
+	}
+}
+
+// UserSecretFromFull converts a full database UserSecret row to an
+// SDK UserSecret, omitting the value and encryption key ID.
+func UserSecretFromFull(secret database.UserSecret) codersdk.UserSecret {
+	return codersdk.UserSecret{
+		ID:          secret.ID,
+		Name:        secret.Name,
+		Description: secret.Description,
+		EnvName:     secret.EnvName,
+		FilePath:    secret.FilePath,
+		CreatedAt:   secret.CreatedAt,
+		UpdatedAt:   secret.UpdatedAt,
+	}
+}
+
+// UserSecrets converts a slice of database ListUserSecretsRow to
+// SDK UserSecret values.
+func UserSecrets(secrets []database.ListUserSecretsRow) []codersdk.UserSecret {
+	result := make([]codersdk.UserSecret, 0, len(secrets))
+	for _, s := range secrets {
+		result = append(result, UserSecret(s))
+	}
+	return result
+}

coderd/database/db2sdk/db2sdk_test.go

@@ -552,6 +552,10 @@ func TestChat_AllFieldsPopulated(t *testing.T) {
 			RawMessage: json.RawMessage(`[{"type":"context-file","context_file_path":"/AGENTS.md"}]`),
 			Valid:      true,
 		},
+		DynamicTools: pqtype.NullRawMessage{
+			RawMessage: json.RawMessage(`[{"name":"tool1","description":"test tool","inputSchema":{"type":"object"}}]`),
+			Valid:      true,
+		},
 	}
 	// Only ChatID is needed here. This test checks that
 	// Chat.DiffStatus is non-nil, not that every DiffStatus
@@ -561,14 +565,26 @@ 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 +597,112 @@ func TestChat_AllFieldsPopulated(t *testing.T) {
 	}
 }
 
+func TestChat_FileMetadataConversion(t *testing.T) {
+	t.Parallel()
+
+	ownerID := uuid.New()
+	orgID := uuid.New()
+	fileID := uuid.New()
+	now := dbtime.Now()
+
+	chat := database.Chat{
+		ID:                uuid.New(),
+		OwnerID:           ownerID,
+		LastModelConfigID: uuid.New(),
+		Title:             "file metadata test",
+		Status:            database.ChatStatusWaiting,
+		CreatedAt:         now,
+		UpdatedAt:         now,
+	}
+
+	rows := []database.GetChatFileMetadataByChatIDRow{
+		{
+			ID:             fileID,
+			OwnerID:        ownerID,
+			OrganizationID: orgID,
+			Name:           "screenshot.png",
+			Mimetype:       "image/png",
+			CreatedAt:      now,
+		},
+	}
+
+	result := db2sdk.Chat(chat, nil, rows)
+
+	require.Len(t, result.Files, 1)
+	f := result.Files[0]
+	require.Equal(t, fileID, f.ID)
+	require.Equal(t, ownerID, f.OwnerID, "OwnerID must be mapped from DB row")
+	require.Equal(t, orgID, f.OrganizationID, "OrganizationID must be mapped from DB row")
+	require.Equal(t, "screenshot.png", f.Name)
+	require.Equal(t, "image/png", f.MimeType)
+	require.Equal(t, now, f.CreatedAt)
+
+	// Verify JSON serialization uses snake_case for mime_type.
+	data, err := json.Marshal(f)
+	require.NoError(t, err)
+	require.Contains(t, string(data), `"mime_type"`)
+	require.NotContains(t, string(data), `"mimetype"`)
+}
+
+func TestChat_NilFilesOmitted(t *testing.T) {
+	t.Parallel()
+
+	chat := database.Chat{
+		ID:                uuid.New(),
+		OwnerID:           uuid.New(),
+		LastModelConfigID: uuid.New(),
+		Title:             "no files",
+		Status:            database.ChatStatusWaiting,
+		CreatedAt:         dbtime.Now(),
+		UpdatedAt:         dbtime.Now(),
+	}
+
+	result := db2sdk.Chat(chat, nil, nil)
+	require.Empty(t, result.Files)
+}
+
+func TestChat_MultipleFiles(t *testing.T) {
+	t.Parallel()
+
+	now := dbtime.Now()
+	file1 := uuid.New()
+	file2 := uuid.New()
+
+	chat := database.Chat{
+		ID:                uuid.New(),
+		OwnerID:           uuid.New(),
+		LastModelConfigID: uuid.New(),
+		Title:             "multi file test",
+		Status:            database.ChatStatusWaiting,
+		CreatedAt:         now,
+		UpdatedAt:         now,
+	}
+
+	rows := []database.GetChatFileMetadataByChatIDRow{
+		{
+			ID:             file1,
+			OwnerID:        chat.OwnerID,
+			OrganizationID: uuid.New(),
+			Name:           "a.png",
+			Mimetype:       "image/png",
+			CreatedAt:      now,
+		},
+		{
+			ID:             file2,
+			OwnerID:        chat.OwnerID,
+			OrganizationID: uuid.New(),
+			Name:           "b.txt",
+			Mimetype:       "text/plain",
+			CreatedAt:      now,
+		},
+	}
+
+	result := db2sdk.Chat(chat, nil, rows)
+	require.Len(t, result.Files, 2)
+	require.Equal(t, "a.png", result.Files[0].Name)
+	require.Equal(t, "b.txt", result.Files[1].Name)
+}
+
 func TestChatQueuedMessage_MalformedContent(t *testing.T) {
 	t.Parallel()
 

coderd/database/dbauthz/dbauthz.go

@@ -1708,6 +1708,17 @@ func (q *querier) CleanupDeletedMCPServerIDsFromChats(ctx context.Context) error
 	return q.db.CleanupDeletedMCPServerIDsFromChats(ctx)
 }
 
+func (q *querier) ClearChatMessageProviderResponseIDsByChatID(ctx context.Context, chatID uuid.UUID) error {
+	chat, err := q.db.GetChatByID(ctx, chatID)
+	if err != nil {
+		return err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
+		return err
+	}
+	return q.db.ClearChatMessageProviderResponseIDsByChatID(ctx, chatID)
+}
+
 func (q *querier) CountAIBridgeInterceptions(ctx context.Context, arg database.CountAIBridgeInterceptionsParams) (int64, error) {
 	prep, err := prepareSQLFilter(ctx, q.auth, policy.ActionRead, rbac.ResourceAibridgeInterception.Type)
 	if err != nil {
@@ -2031,6 +2042,20 @@ func (q *querier) DeleteOldAuditLogs(ctx context.Context, arg database.DeleteOld
 	return q.db.DeleteOldAuditLogs(ctx, arg)
 }
 
+func (q *querier) DeleteOldChatFiles(ctx context.Context, arg database.DeleteOldChatFilesParams) ([]database.DeleteOldChatFilesRow, error) {
+	if err := q.authorizeContext(ctx, policy.ActionDelete, rbac.ResourceSystem); err != nil {
+		return nil, err
+	}
+	return q.db.DeleteOldChatFiles(ctx, arg)
+}
+
+func (q *querier) DeleteOldChats(ctx context.Context, arg database.DeleteOldChatsParams) (int64, error) {
+	if err := q.authorizeContext(ctx, policy.ActionDelete, rbac.ResourceSystem); err != nil {
+		return 0, err
+	}
+	return q.db.DeleteOldChats(ctx, arg)
+}
+
 func (q *querier) DeleteOldConnectionLogs(ctx context.Context, arg database.DeleteOldConnectionLogsParams) (int64, error) {
 	if err := q.authorizeContext(ctx, policy.ActionDelete, rbac.ResourceSystem); err != nil {
 		return 0, err
@@ -2155,17 +2180,12 @@ func (q *querier) DeleteUserChatProviderKey(ctx context.Context, arg database.De
 	return q.db.DeleteUserChatProviderKey(ctx, arg)
 }
 
-func (q *querier) DeleteUserSecret(ctx context.Context, id uuid.UUID) error {
-	// First get the secret to check ownership
-	secret, err := q.GetUserSecret(ctx, id)
-	if err != nil {
-		return err
+func (q *querier) DeleteUserSecretByUserIDAndName(ctx context.Context, arg database.DeleteUserSecretByUserIDAndNameParams) (int64, error) {
+	obj := rbac.ResourceUserSecret.WithOwner(arg.UserID.String())
+	if err := q.authorizeContext(ctx, policy.ActionDelete, obj); err != nil {
+		return 0, err
 	}
-
-	if err := q.authorizeContext(ctx, policy.ActionDelete, secret); err != nil {
-		return err
-	}
-	return q.db.DeleteUserSecret(ctx, id)
+	return q.db.DeleteUserSecretByUserIDAndName(ctx, arg)
 }
 
 func (q *querier) DeleteWebpushSubscriptionByUserIDAndEndpoint(ctx context.Context, arg database.DeleteWebpushSubscriptionByUserIDAndEndpointParams) error {
@@ -2404,6 +2424,10 @@ func (q *querier) GetActiveAISeatCount(ctx context.Context) (int64, error) {
 	return q.db.GetActiveAISeatCount(ctx)
 }
 
+func (q *querier) GetActiveChatsByAgentID(ctx context.Context, agentID uuid.UUID) ([]database.Chat, error) {
+	return fetchWithPostFilter(q.auth, policy.ActionRead, q.db.GetActiveChatsByAgentID)(ctx, agentID)
+}
+
 func (q *querier) GetActivePresetPrebuildSchedules(ctx context.Context) ([]database.TemplateVersionPresetPrebuildSchedule, error) {
 	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceTemplate.All()); err != nil {
 		return nil, err
@@ -2583,6 +2607,10 @@ func (q *querier) GetChatFileByID(ctx context.Context, id uuid.UUID) (database.C
 	return file, nil
 }
 
+func (q *querier) GetChatFileMetadataByChatID(ctx context.Context, chatID uuid.UUID) ([]database.GetChatFileMetadataByChatIDRow, error) {
+	return fetchWithPostFilter(q.auth, policy.ActionRead, q.db.GetChatFileMetadataByChatID)(ctx, chatID)
+}
+
 func (q *querier) GetChatFilesByIDs(ctx context.Context, ids []uuid.UUID) ([]database.ChatFile, error) {
 	files, err := q.db.GetChatFilesByIDs(ctx, ids)
 	if err != nil {
@@ -2623,6 +2651,14 @@ func (q *querier) GetChatMessageByID(ctx context.Context, id int64) (database.Ch
 	return msg, nil
 }
 
+func (q *querier) GetChatMessageSummariesPerChat(ctx context.Context, createdAfter time.Time) ([]database.GetChatMessageSummariesPerChatRow, error) {
+	// Telemetry queries are called from system contexts only.
+	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceSystem); err != nil {
+		return nil, err
+	}
+	return q.db.GetChatMessageSummariesPerChat(ctx, createdAfter)
+}
+
 func (q *querier) GetChatMessagesByChatID(ctx context.Context, arg database.GetChatMessagesByChatIDParams) ([]database.ChatMessage, error) {
 	// Authorize read on the parent chat.
 	_, err := q.GetChatByID(ctx, arg.ChatID)
@@ -2671,6 +2707,14 @@ func (q *querier) GetChatModelConfigs(ctx context.Context) ([]database.ChatModel
 	return q.db.GetChatModelConfigs(ctx)
 }
 
+func (q *querier) GetChatModelConfigsForTelemetry(ctx context.Context) ([]database.GetChatModelConfigsForTelemetryRow, error) {
+	// Telemetry queries are called from system contexts only.
+	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceSystem); err != nil {
+		return nil, err
+	}
+	return q.db.GetChatModelConfigsForTelemetry(ctx)
+}
+
 func (q *querier) GetChatProviderByID(ctx context.Context, id uuid.UUID) (database.ChatProvider, error) {
 	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceDeploymentConfig); err != nil {
 		return database.ChatProvider{}, err
@@ -2700,6 +2744,15 @@ func (q *querier) GetChatQueuedMessages(ctx context.Context, chatID uuid.UUID) (
 	return q.db.GetChatQueuedMessages(ctx, chatID)
 }
 
+func (q *querier) GetChatRetentionDays(ctx context.Context) (int32, error) {
+	// Chat retention is a deployment-wide config read by dbpurge.
+	// Only requires a valid actor in context.
+	if _, ok := ActorFromContext(ctx); !ok {
+		return 0, ErrNoActor
+	}
+	return q.db.GetChatRetentionDays(ctx)
+}
+
 func (q *querier) GetChatSystemPrompt(ctx context.Context) (string, error) {
 	// The system prompt is a deployment-wide setting read during chat
 	// creation by every authenticated user, so no RBAC policy check
@@ -2778,6 +2831,14 @@ func (q *querier) GetChatsByWorkspaceIDs(ctx context.Context, ids []uuid.UUID) (
 	return fetchWithPostFilter(q.auth, policy.ActionRead, q.db.GetChatsByWorkspaceIDs)(ctx, ids)
 }
 
+func (q *querier) GetChatsUpdatedAfter(ctx context.Context, updatedAfter time.Time) ([]database.GetChatsUpdatedAfterRow, error) {
+	// Telemetry queries are called from system contexts only.
+	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceSystem); err != nil {
+		return nil, err
+	}
+	return q.db.GetChatsUpdatedAfter(ctx, updatedAfter)
+}
+
 func (q *querier) GetConnectionLogsOffset(ctx context.Context, arg database.GetConnectionLogsOffsetParams) ([]database.GetConnectionLogsOffsetRow, error) {
 	// Just like with the audit logs query, shortcut if the user is an owner.
 	err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceConnectionLog)
@@ -4124,19 +4185,6 @@ func (q *querier) GetUserNotificationPreferences(ctx context.Context, userID uui
 	return q.db.GetUserNotificationPreferences(ctx, userID)
 }
 
-func (q *querier) GetUserSecret(ctx context.Context, id uuid.UUID) (database.UserSecret, error) {
-	// First get the secret to check ownership
-	secret, err := q.db.GetUserSecret(ctx, id)
-	if err != nil {
-		return database.UserSecret{}, err
-	}
-
-	if err := q.authorizeContext(ctx, policy.ActionRead, secret); err != nil {
-		return database.UserSecret{}, err
-	}
-	return secret, nil
-}
-
 func (q *querier) GetUserSecretByUserIDAndName(ctx context.Context, arg database.GetUserSecretByUserIDAndNameParams) (database.UserSecret, error) {
 	obj := rbac.ResourceUserSecret.WithOwner(arg.UserID.String())
 	if err := q.authorizeContext(ctx, policy.ActionRead, obj); err != nil {
@@ -5393,6 +5441,17 @@ func (q *querier) InsertWorkspaceResourceMetadata(ctx context.Context, arg datab
 	return q.db.InsertWorkspaceResourceMetadata(ctx, arg)
 }
 
+func (q *querier) LinkChatFiles(ctx context.Context, arg database.LinkChatFilesParams) (int32, error) {
+	chat, err := q.db.GetChatByID(ctx, arg.ChatID)
+	if err != nil {
+		return 0, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
+		return 0, err
+	}
+	return q.db.LinkChatFiles(ctx, arg)
+}
+
 func (q *querier) ListAIBridgeClients(ctx context.Context, arg database.ListAIBridgeClientsParams) ([]string, error) {
 	prep, err := prepareSQLFilter(ctx, q.auth, policy.ActionRead, rbac.ResourceAibridgeInterception.Type)
 	if err != nil {
@@ -5509,7 +5568,7 @@ func (q *querier) ListUserChatCompactionThresholds(ctx context.Context, userID u
 	return q.db.ListUserChatCompactionThresholds(ctx, userID)
 }
 
-func (q *querier) ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]database.UserSecret, error) {
+func (q *querier) ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]database.ListUserSecretsRow, error) {
 	obj := rbac.ResourceUserSecret.WithOwner(userID.String())
 	if err := q.authorizeContext(ctx, policy.ActionRead, obj); err != nil {
 		return nil, err
@@ -5517,6 +5576,16 @@ func (q *querier) ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]data
 	return q.db.ListUserSecrets(ctx, userID)
 }
 
+func (q *querier) ListUserSecretsWithValues(ctx context.Context, userID uuid.UUID) ([]database.UserSecret, error) {
+	// This query returns decrypted secret values and must only be called
+	// from system contexts (provisioner, agent manifest). REST API
+	// handlers should use ListUserSecrets (metadata only).
+	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceSystem); err != nil {
+		return nil, err
+	}
+	return q.db.ListUserSecretsWithValues(ctx, userID)
+}
+
 func (q *querier) ListWorkspaceAgentPortShares(ctx context.Context, workspaceID uuid.UUID) ([]database.WorkspaceAgentPortShare, error) {
 	workspace, err := q.db.GetWorkspaceByID(ctx, workspaceID)
 	if err != nil {
@@ -5674,6 +5743,17 @@ func (q *querier) SoftDeleteChatMessagesAfterID(ctx context.Context, arg databas
 	return q.db.SoftDeleteChatMessagesAfterID(ctx, arg)
 }
 
+func (q *querier) SoftDeleteContextFileMessages(ctx context.Context, chatID uuid.UUID) error {
+	chat, err := q.db.GetChatByID(ctx, chatID)
+	if err != nil {
+		return err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
+		return err
+	}
+	return q.db.SoftDeleteContextFileMessages(ctx, chatID)
+}
+
 func (q *querier) TryAcquireLock(ctx context.Context, id int64) (bool, error) {
 	return q.db.TryAcquireLock(ctx, id)
 }
@@ -5767,15 +5847,15 @@ 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) {
@@ -6617,17 +6697,12 @@ func (q *querier) UpdateUserRoles(ctx context.Context, arg database.UpdateUserRo
 	return q.db.UpdateUserRoles(ctx, arg)
 }
 
-func (q *querier) UpdateUserSecret(ctx context.Context, arg database.UpdateUserSecretParams) (database.UserSecret, error) {
-	// First get the secret to check ownership
-	secret, err := q.db.GetUserSecret(ctx, arg.ID)
-	if err != nil {
+func (q *querier) UpdateUserSecretByUserIDAndName(ctx context.Context, arg database.UpdateUserSecretByUserIDAndNameParams) (database.UserSecret, error) {
+	obj := rbac.ResourceUserSecret.WithOwner(arg.UserID.String())
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, obj); err != nil {
 		return database.UserSecret{}, err
 	}
-
-	if err := q.authorizeContext(ctx, policy.ActionUpdate, secret); err != nil {
-		return database.UserSecret{}, err
-	}
-	return q.db.UpdateUserSecret(ctx, arg)
+	return q.db.UpdateUserSecretByUserIDAndName(ctx, arg)
 }
 
 func (q *querier) UpdateUserStatus(ctx context.Context, arg database.UpdateUserStatusParams) (database.User, error) {
@@ -7029,6 +7104,13 @@ func (q *querier) UpsertChatIncludeDefaultSystemPrompt(ctx context.Context, incl
 	return q.db.UpsertChatIncludeDefaultSystemPrompt(ctx, includeDefaultSystemPrompt)
 }
 
+func (q *querier) UpsertChatRetentionDays(ctx context.Context, retentionDays int32) error {
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceDeploymentConfig); err != nil {
+		return err
+	}
+	return q.db.UpsertChatRetentionDays(ctx, retentionDays)
+}
+
 func (q *querier) UpsertChatSystemPrompt(ctx context.Context, value string) error {
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceDeploymentConfig); err != nil {
 		return err

coderd/database/dbauthz/dbauthz_test.go

@@ -400,6 +400,17 @@ func (s *MethodTestSuite) TestChats() {
 		dbm.EXPECT().UnarchiveChatByID(gomock.Any(), chat.ID).Return([]database.Chat{chat}, nil).AnyTimes()
 		check.Args(chat.ID).Asserts(chat, policy.ActionUpdate).Returns([]database.Chat{chat})
 	}))
+	s.Run("LinkChatFiles", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		arg := database.LinkChatFilesParams{
+			ChatID:       chat.ID,
+			MaxFileLinks: int32(codersdk.MaxChatFileIDs),
+			FileIds:      []uuid.UUID{uuid.New()},
+		}
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		dbm.EXPECT().LinkChatFiles(gomock.Any(), arg).Return(int32(0), nil).AnyTimes()
+		check.Args(arg).Asserts(chat, policy.ActionUpdate).Returns(int32(0))
+	}))
 	s.Run("PinChatByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		chat := testutil.Fake(s.T(), faker, database.Chat{})
 		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
@@ -467,6 +478,24 @@ func (s *MethodTestSuite) TestChats() {
 		dbm.EXPECT().GetChatsByWorkspaceIDs(gomock.Any(), arg).Return([]database.Chat{chatA, chatB}, nil).AnyTimes()
 		check.Args(arg).Asserts(chatA, policy.ActionRead, chatB, policy.ActionRead).Returns([]database.Chat{chatA, chatB})
 	}))
+	s.Run("GetActiveChatsByAgentID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		agentID := uuid.New()
+		dbm.EXPECT().GetActiveChatsByAgentID(gomock.Any(), agentID).Return([]database.Chat{chat}, nil).AnyTimes()
+		check.Args(agentID).Asserts(chat, policy.ActionRead).Returns([]database.Chat{chat})
+	}))
+	s.Run("SoftDeleteContextFileMessages", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		dbm.EXPECT().SoftDeleteContextFileMessages(gomock.Any(), chat.ID).Return(nil).AnyTimes()
+		check.Args(chat.ID).Asserts(chat, policy.ActionUpdate).Returns()
+	}))
+	s.Run("ClearChatMessageProviderResponseIDsByChatID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		dbm.EXPECT().ClearChatMessageProviderResponseIDsByChatID(gomock.Any(), chat.ID).Return(nil).AnyTimes()
+		check.Args(chat.ID).Asserts(chat, policy.ActionUpdate).Returns()
+	}))
 	s.Run("GetChatCostPerChat", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
 		arg := database.GetChatCostPerChatParams{
 			OwnerID:   uuid.New(),
@@ -576,6 +605,35 @@ func (s *MethodTestSuite) TestChats() {
 		dbm.EXPECT().GetChatFilesByIDs(gomock.Any(), []uuid.UUID{file.ID}).Return([]database.ChatFile{file}, nil).AnyTimes()
 		check.Args([]uuid.UUID{file.ID}).Asserts(rbac.ResourceChat.WithOwner(file.OwnerID.String()).InOrg(file.OrganizationID).WithID(file.ID), policy.ActionRead).Returns([]database.ChatFile{file})
 	}))
+	s.Run("GetChatFileMetadataByChatID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		file := testutil.Fake(s.T(), faker, database.ChatFile{})
+		rows := []database.GetChatFileMetadataByChatIDRow{{
+			ID:             file.ID,
+			Name:           file.Name,
+			Mimetype:       file.Mimetype,
+			CreatedAt:      file.CreatedAt,
+			OwnerID:        file.OwnerID,
+			OrganizationID: file.OrganizationID,
+		}}
+		dbm.EXPECT().GetChatFileMetadataByChatID(gomock.Any(), file.ID).Return(rows, nil).AnyTimes()
+		check.Args(file.ID).Asserts(rbac.ResourceChat.WithOwner(file.OwnerID.String()).InOrg(file.OrganizationID).WithID(file.ID), policy.ActionRead).Returns(rows)
+	}))
+	s.Run("DeleteOldChatFiles", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		dbm.EXPECT().DeleteOldChatFiles(gomock.Any(), database.DeleteOldChatFilesParams{}).Return(int64(0), nil).AnyTimes()
+		check.Args(database.DeleteOldChatFilesParams{}).Asserts(rbac.ResourceSystem, policy.ActionDelete)
+	}))
+	s.Run("DeleteOldChats", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		dbm.EXPECT().DeleteOldChats(gomock.Any(), database.DeleteOldChatsParams{}).Return(int64(0), nil).AnyTimes()
+		check.Args(database.DeleteOldChatsParams{}).Asserts(rbac.ResourceSystem, policy.ActionDelete)
+	}))
+	s.Run("GetChatRetentionDays", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		dbm.EXPECT().GetChatRetentionDays(gomock.Any()).Return(int32(30), nil).AnyTimes()
+		check.Args().Asserts()
+	}))
+	s.Run("UpsertChatRetentionDays", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		dbm.EXPECT().UpsertChatRetentionDays(gomock.Any(), int32(30)).Return(nil).AnyTimes()
+		check.Args(int32(30)).Asserts(rbac.ResourceDeploymentConfig, policy.ActionUpdate)
+	}))
 	s.Run("GetChatMessageByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		chat := testutil.Fake(s.T(), faker, database.Chat{})
 		msg := testutil.Fake(s.T(), faker, database.ChatMessage{ChatID: chat.ID})
@@ -818,15 +876,15 @@ 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{})
@@ -3972,6 +4030,20 @@ func (s *MethodTestSuite) TestSystemFunctions() {
 		dbm.EXPECT().GetWorkspaceAgentsCreatedAfter(gomock.Any(), ts).Return([]database.WorkspaceAgent{}, nil).AnyTimes()
 		check.Args(ts).Asserts(rbac.ResourceSystem, policy.ActionRead)
 	}))
+	s.Run("GetChatsUpdatedAfter", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		ts := dbtime.Now()
+		dbm.EXPECT().GetChatsUpdatedAfter(gomock.Any(), ts).Return([]database.GetChatsUpdatedAfterRow{}, nil).AnyTimes()
+		check.Args(ts).Asserts(rbac.ResourceSystem, policy.ActionRead)
+	}))
+	s.Run("GetChatMessageSummariesPerChat", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		ts := dbtime.Now()
+		dbm.EXPECT().GetChatMessageSummariesPerChat(gomock.Any(), ts).Return([]database.GetChatMessageSummariesPerChatRow{}, nil).AnyTimes()
+		check.Args(ts).Asserts(rbac.ResourceSystem, policy.ActionRead)
+	}))
+	s.Run("GetChatModelConfigsForTelemetry", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		dbm.EXPECT().GetChatModelConfigsForTelemetry(gomock.Any()).Return([]database.GetChatModelConfigsForTelemetryRow{}, nil).AnyTimes()
+		check.Args().Asserts(rbac.ResourceSystem, policy.ActionRead)
+	}))
 	s.Run("GetWorkspaceAppsCreatedAfter", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
 		ts := dbtime.Now()
 		dbm.EXPECT().GetWorkspaceAppsCreatedAfter(gomock.Any(), ts).Return([]database.WorkspaceApp{}, nil).AnyTimes()
@@ -5322,19 +5394,20 @@ func (s *MethodTestSuite) TestUserSecrets() {
 			Asserts(rbac.ResourceUserSecret.WithOwner(user.ID.String()), policy.ActionRead).
 			Returns(secret)
 	}))
-	s.Run("GetUserSecret", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		secret := testutil.Fake(s.T(), faker, database.UserSecret{})
-		dbm.EXPECT().GetUserSecret(gomock.Any(), secret.ID).Return(secret, nil).AnyTimes()
-		check.Args(secret.ID).
-			Asserts(secret, policy.ActionRead).
-			Returns(secret)
-	}))
 	s.Run("ListUserSecrets", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		user := testutil.Fake(s.T(), faker, database.User{})
-		secret := testutil.Fake(s.T(), faker, database.UserSecret{UserID: user.ID})
-		dbm.EXPECT().ListUserSecrets(gomock.Any(), user.ID).Return([]database.UserSecret{secret}, nil).AnyTimes()
+		row := testutil.Fake(s.T(), faker, database.ListUserSecretsRow{UserID: user.ID})
+		dbm.EXPECT().ListUserSecrets(gomock.Any(), user.ID).Return([]database.ListUserSecretsRow{row}, nil).AnyTimes()
 		check.Args(user.ID).
 			Asserts(rbac.ResourceUserSecret.WithOwner(user.ID.String()), policy.ActionRead).
+			Returns([]database.ListUserSecretsRow{row})
+	}))
+	s.Run("ListUserSecretsWithValues", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		user := testutil.Fake(s.T(), faker, database.User{})
+		secret := testutil.Fake(s.T(), faker, database.UserSecret{UserID: user.ID})
+		dbm.EXPECT().ListUserSecretsWithValues(gomock.Any(), user.ID).Return([]database.UserSecret{secret}, nil).AnyTimes()
+		check.Args(user.ID).
+			Asserts(rbac.ResourceSystem, policy.ActionRead).
 			Returns([]database.UserSecret{secret})
 	}))
 	s.Run("CreateUserSecret", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
@@ -5346,23 +5419,22 @@ func (s *MethodTestSuite) TestUserSecrets() {
 			Asserts(rbac.ResourceUserSecret.WithOwner(user.ID.String()), policy.ActionCreate).
 			Returns(ret)
 	}))
-	s.Run("UpdateUserSecret", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		secret := testutil.Fake(s.T(), faker, database.UserSecret{})
-		updated := testutil.Fake(s.T(), faker, database.UserSecret{ID: secret.ID})
-		arg := database.UpdateUserSecretParams{ID: secret.ID}
-		dbm.EXPECT().GetUserSecret(gomock.Any(), secret.ID).Return(secret, nil).AnyTimes()
-		dbm.EXPECT().UpdateUserSecret(gomock.Any(), arg).Return(updated, nil).AnyTimes()
+	s.Run("UpdateUserSecretByUserIDAndName", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		user := testutil.Fake(s.T(), faker, database.User{})
+		updated := testutil.Fake(s.T(), faker, database.UserSecret{UserID: user.ID})
+		arg := database.UpdateUserSecretByUserIDAndNameParams{UserID: user.ID, Name: "test"}
+		dbm.EXPECT().UpdateUserSecretByUserIDAndName(gomock.Any(), arg).Return(updated, nil).AnyTimes()
 		check.Args(arg).
-			Asserts(secret, policy.ActionUpdate).
+			Asserts(rbac.ResourceUserSecret.WithOwner(user.ID.String()), policy.ActionUpdate).
 			Returns(updated)
 	}))
-	s.Run("DeleteUserSecret", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
-		secret := testutil.Fake(s.T(), faker, database.UserSecret{})
-		dbm.EXPECT().GetUserSecret(gomock.Any(), secret.ID).Return(secret, nil).AnyTimes()
-		dbm.EXPECT().DeleteUserSecret(gomock.Any(), secret.ID).Return(nil).AnyTimes()
-		check.Args(secret.ID).
-			Asserts(secret, policy.ActionRead, secret, policy.ActionDelete).
-			Returns()
+	s.Run("DeleteUserSecretByUserIDAndName", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		user := testutil.Fake(s.T(), faker, database.User{})
+		arg := database.DeleteUserSecretByUserIDAndNameParams{UserID: user.ID, Name: "test"}
+		dbm.EXPECT().DeleteUserSecretByUserIDAndName(gomock.Any(), arg).Return(int64(1), nil).AnyTimes()
+		check.Args(arg).
+			Asserts(rbac.ResourceUserSecret.WithOwner(user.ID.String()), policy.ActionDelete).
+			Returns(int64(1))
 	}))
 }
 

coderd/database/dbgen/dbgen.go

@@ -1597,6 +1597,7 @@ func UserSecret(t testing.TB, db database.Store, seed database.UserSecret) datab
 		Name:        takeFirst(seed.Name, "secret-name"),
 		Description: takeFirst(seed.Description, "secret description"),
 		Value:       takeFirst(seed.Value, "secret value"),
+		ValueKeyID:  seed.ValueKeyID,
 		EnvName:     takeFirst(seed.EnvName, "SECRET_ENV_NAME"),
 		FilePath:    takeFirst(seed.FilePath, "~/secret/file/path"),
 	})
@@ -1643,6 +1644,8 @@ func AIBridgeInterception(t testing.TB, db database.Store, seed database.InsertA
 		ThreadParentInterceptionID: seed.ThreadParentInterceptionID,
 		ThreadRootInterceptionID:   seed.ThreadRootInterceptionID,
 		ClientSessionID:            seed.ClientSessionID,
+		CredentialKind:             takeFirst(seed.CredentialKind, database.CredentialKindCentralized),
+		CredentialHint:             takeFirst(seed.CredentialHint, ""),
 	})
 	if endedAt != nil {
 		interception, err = db.UpdateAIBridgeInterceptionEnded(genCtx, database.UpdateAIBridgeInterceptionEndedParams{

coderd/database/dbmetrics/querymetrics.go

@@ -280,6 +280,14 @@ func (m queryMetricsStore) CleanupDeletedMCPServerIDsFromChats(ctx context.Conte
 	return r0
 }
 
+func (m queryMetricsStore) ClearChatMessageProviderResponseIDsByChatID(ctx context.Context, chatID uuid.UUID) error {
+	start := time.Now()
+	r0 := m.s.ClearChatMessageProviderResponseIDsByChatID(ctx, chatID)
+	m.queryLatencies.WithLabelValues("ClearChatMessageProviderResponseIDsByChatID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "ClearChatMessageProviderResponseIDsByChatID").Inc()
+	return r0
+}
+
 func (m queryMetricsStore) CountAIBridgeInterceptions(ctx context.Context, arg database.CountAIBridgeInterceptionsParams) (int64, error) {
 	start := time.Now()
 	r0, r1 := m.s.CountAIBridgeInterceptions(ctx, arg)
@@ -592,6 +600,22 @@ func (m queryMetricsStore) DeleteOldAuditLogs(ctx context.Context, arg database.
 	return r0, r1
 }
 
+func (m queryMetricsStore) DeleteOldChatFiles(ctx context.Context, arg database.DeleteOldChatFilesParams) ([]database.DeleteOldChatFilesRow, error) {
+	start := time.Now()
+	r0, r1 := m.s.DeleteOldChatFiles(ctx, arg)
+	m.queryLatencies.WithLabelValues("DeleteOldChatFiles").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "DeleteOldChatFiles").Inc()
+	return r0, r1
+}
+
+func (m queryMetricsStore) DeleteOldChats(ctx context.Context, arg database.DeleteOldChatsParams) (int64, error) {
+	start := time.Now()
+	r0, r1 := m.s.DeleteOldChats(ctx, arg)
+	m.queryLatencies.WithLabelValues("DeleteOldChats").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "DeleteOldChats").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) DeleteOldConnectionLogs(ctx context.Context, arg database.DeleteOldConnectionLogsParams) (int64, error) {
 	start := time.Now()
 	r0, r1 := m.s.DeleteOldConnectionLogs(ctx, arg)
@@ -712,12 +736,12 @@ func (m queryMetricsStore) DeleteUserChatProviderKey(ctx context.Context, arg da
 	return r0
 }
 
-func (m queryMetricsStore) DeleteUserSecret(ctx context.Context, id uuid.UUID) error {
+func (m queryMetricsStore) DeleteUserSecretByUserIDAndName(ctx context.Context, arg database.DeleteUserSecretByUserIDAndNameParams) (int64, error) {
 	start := time.Now()
-	r0 := m.s.DeleteUserSecret(ctx, id)
-	m.queryLatencies.WithLabelValues("DeleteUserSecret").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "DeleteUserSecret").Inc()
-	return r0
+	r0, r1 := m.s.DeleteUserSecretByUserIDAndName(ctx, arg)
+	m.queryLatencies.WithLabelValues("DeleteUserSecretByUserIDAndName").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "DeleteUserSecretByUserIDAndName").Inc()
+	return r0, r1
 }
 
 func (m queryMetricsStore) DeleteWebpushSubscriptionByUserIDAndEndpoint(ctx context.Context, arg database.DeleteWebpushSubscriptionByUserIDAndEndpointParams) error {
@@ -952,6 +976,14 @@ func (m queryMetricsStore) GetActiveAISeatCount(ctx context.Context) (int64, err
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetActiveChatsByAgentID(ctx context.Context, agentID uuid.UUID) ([]database.Chat, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetActiveChatsByAgentID(ctx, agentID)
+	m.queryLatencies.WithLabelValues("GetActiveChatsByAgentID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetActiveChatsByAgentID").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetActivePresetPrebuildSchedules(ctx context.Context) ([]database.TemplateVersionPresetPrebuildSchedule, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetActivePresetPrebuildSchedules(ctx)
@@ -1128,6 +1160,14 @@ func (m queryMetricsStore) GetChatFileByID(ctx context.Context, id uuid.UUID) (d
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetChatFileMetadataByChatID(ctx context.Context, chatID uuid.UUID) ([]database.GetChatFileMetadataByChatIDRow, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatFileMetadataByChatID(ctx, chatID)
+	m.queryLatencies.WithLabelValues("GetChatFileMetadataByChatID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatFileMetadataByChatID").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetChatFilesByIDs(ctx context.Context, ids []uuid.UUID) ([]database.ChatFile, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetChatFilesByIDs(ctx, ids)
@@ -1152,6 +1192,14 @@ func (m queryMetricsStore) GetChatMessageByID(ctx context.Context, id int64) (da
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetChatMessageSummariesPerChat(ctx context.Context, createdAfter time.Time) ([]database.GetChatMessageSummariesPerChatRow, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatMessageSummariesPerChat(ctx, createdAfter)
+	m.queryLatencies.WithLabelValues("GetChatMessageSummariesPerChat").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatMessageSummariesPerChat").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetChatMessagesByChatID(ctx context.Context, chatID database.GetChatMessagesByChatIDParams) ([]database.ChatMessage, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetChatMessagesByChatID(ctx, chatID)
@@ -1200,6 +1248,14 @@ func (m queryMetricsStore) GetChatModelConfigs(ctx context.Context) ([]database.
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetChatModelConfigsForTelemetry(ctx context.Context) ([]database.GetChatModelConfigsForTelemetryRow, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatModelConfigsForTelemetry(ctx)
+	m.queryLatencies.WithLabelValues("GetChatModelConfigsForTelemetry").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatModelConfigsForTelemetry").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetChatProviderByID(ctx context.Context, id uuid.UUID) (database.ChatProvider, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetChatProviderByID(ctx, id)
@@ -1232,6 +1288,14 @@ func (m queryMetricsStore) GetChatQueuedMessages(ctx context.Context, chatID uui
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetChatRetentionDays(ctx context.Context) (int32, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatRetentionDays(ctx)
+	m.queryLatencies.WithLabelValues("GetChatRetentionDays").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatRetentionDays").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetChatSystemPrompt(ctx context.Context) (string, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetChatSystemPrompt(ctx)
@@ -1304,6 +1368,14 @@ func (m queryMetricsStore) GetChatsByWorkspaceIDs(ctx context.Context, ids []uui
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetChatsUpdatedAfter(ctx context.Context, updatedAfter time.Time) ([]database.GetChatsUpdatedAfterRow, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatsUpdatedAfter(ctx, updatedAfter)
+	m.queryLatencies.WithLabelValues("GetChatsUpdatedAfter").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatsUpdatedAfter").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetConnectionLogsOffset(ctx context.Context, arg database.GetConnectionLogsOffsetParams) ([]database.GetConnectionLogsOffsetRow, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetConnectionLogsOffset(ctx, arg)
@@ -2616,14 +2688,6 @@ func (m queryMetricsStore) GetUserNotificationPreferences(ctx context.Context, u
 	return r0, r1
 }
 
-func (m queryMetricsStore) GetUserSecret(ctx context.Context, id uuid.UUID) (database.UserSecret, error) {
-	start := time.Now()
-	r0, r1 := m.s.GetUserSecret(ctx, id)
-	m.queryLatencies.WithLabelValues("GetUserSecret").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetUserSecret").Inc()
-	return r0, r1
-}
-
 func (m queryMetricsStore) GetUserSecretByUserIDAndName(ctx context.Context, arg database.GetUserSecretByUserIDAndNameParams) (database.UserSecret, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetUserSecretByUserIDAndName(ctx, arg)
@@ -3776,6 +3840,14 @@ func (m queryMetricsStore) InsertWorkspaceResourceMetadata(ctx context.Context,
 	return r0, r1
 }
 
+func (m queryMetricsStore) LinkChatFiles(ctx context.Context, arg database.LinkChatFilesParams) (int32, error) {
+	start := time.Now()
+	r0, r1 := m.s.LinkChatFiles(ctx, arg)
+	m.queryLatencies.WithLabelValues("LinkChatFiles").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "LinkChatFiles").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) ListAIBridgeClients(ctx context.Context, arg database.ListAIBridgeClientsParams) ([]string, error) {
 	start := time.Now()
 	r0, r1 := m.s.ListAIBridgeClients(ctx, arg)
@@ -3904,7 +3976,7 @@ func (m queryMetricsStore) ListUserChatCompactionThresholds(ctx context.Context,
 	return r0, r1
 }
 
-func (m queryMetricsStore) ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]database.UserSecret, error) {
+func (m queryMetricsStore) ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]database.ListUserSecretsRow, error) {
 	start := time.Now()
 	r0, r1 := m.s.ListUserSecrets(ctx, userID)
 	m.queryLatencies.WithLabelValues("ListUserSecrets").Observe(time.Since(start).Seconds())
@@ -3912,6 +3984,14 @@ func (m queryMetricsStore) ListUserSecrets(ctx context.Context, userID uuid.UUID
 	return r0, r1
 }
 
+func (m queryMetricsStore) ListUserSecretsWithValues(ctx context.Context, userID uuid.UUID) ([]database.UserSecret, error) {
+	start := time.Now()
+	r0, r1 := m.s.ListUserSecretsWithValues(ctx, userID)
+	m.queryLatencies.WithLabelValues("ListUserSecretsWithValues").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "ListUserSecretsWithValues").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) ListWorkspaceAgentPortShares(ctx context.Context, workspaceID uuid.UUID) ([]database.WorkspaceAgentPortShare, error) {
 	start := time.Now()
 	r0, r1 := m.s.ListWorkspaceAgentPortShares(ctx, workspaceID)
@@ -4040,6 +4120,14 @@ func (m queryMetricsStore) SoftDeleteChatMessagesAfterID(ctx context.Context, ar
 	return r0
 }
 
+func (m queryMetricsStore) SoftDeleteContextFileMessages(ctx context.Context, chatID uuid.UUID) error {
+	start := time.Now()
+	r0 := m.s.SoftDeleteContextFileMessages(ctx, chatID)
+	m.queryLatencies.WithLabelValues("SoftDeleteContextFileMessages").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "SoftDeleteContextFileMessages").Inc()
+	return r0
+}
+
 func (m queryMetricsStore) TryAcquireLock(ctx context.Context, pgTryAdvisoryXactLock int64) (bool, error) {
 	start := time.Now()
 	r0, r1 := m.s.TryAcquireLock(ctx, pgTryAdvisoryXactLock)
@@ -4120,11 +4208,11 @@ 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
 }
 
@@ -4680,11 +4768,11 @@ func (m queryMetricsStore) UpdateUserRoles(ctx context.Context, arg database.Upd
 	return r0, r1
 }
 
-func (m queryMetricsStore) UpdateUserSecret(ctx context.Context, arg database.UpdateUserSecretParams) (database.UserSecret, error) {
+func (m queryMetricsStore) UpdateUserSecretByUserIDAndName(ctx context.Context, arg database.UpdateUserSecretByUserIDAndNameParams) (database.UserSecret, error) {
 	start := time.Now()
-	r0, r1 := m.s.UpdateUserSecret(ctx, arg)
-	m.queryLatencies.WithLabelValues("UpdateUserSecret").Observe(time.Since(start).Seconds())
-	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateUserSecret").Inc()
+	r0, r1 := m.s.UpdateUserSecretByUserIDAndName(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpdateUserSecretByUserIDAndName").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateUserSecretByUserIDAndName").Inc()
 	return r0, r1
 }
 
@@ -4984,6 +5072,14 @@ func (m queryMetricsStore) UpsertChatIncludeDefaultSystemPrompt(ctx context.Cont
 	return r0
 }
 
+func (m queryMetricsStore) UpsertChatRetentionDays(ctx context.Context, retentionDays int32) error {
+	start := time.Now()
+	r0 := m.s.UpsertChatRetentionDays(ctx, retentionDays)
+	m.queryLatencies.WithLabelValues("UpsertChatRetentionDays").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpsertChatRetentionDays").Inc()
+	return r0
+}
+
 func (m queryMetricsStore) UpsertChatSystemPrompt(ctx context.Context, value string) error {
 	start := time.Now()
 	r0 := m.s.UpsertChatSystemPrompt(ctx, value)

coderd/database/dbmock/dbmock.go

@@ -363,6 +363,20 @@ func (mr *MockStoreMockRecorder) CleanupDeletedMCPServerIDsFromChats(ctx any) *g
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "CleanupDeletedMCPServerIDsFromChats", reflect.TypeOf((*MockStore)(nil).CleanupDeletedMCPServerIDsFromChats), ctx)
 }
 
+// ClearChatMessageProviderResponseIDsByChatID mocks base method.
+func (m *MockStore) ClearChatMessageProviderResponseIDsByChatID(ctx context.Context, chatID uuid.UUID) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "ClearChatMessageProviderResponseIDsByChatID", ctx, chatID)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// ClearChatMessageProviderResponseIDsByChatID indicates an expected call of ClearChatMessageProviderResponseIDsByChatID.
+func (mr *MockStoreMockRecorder) ClearChatMessageProviderResponseIDsByChatID(ctx, chatID any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "ClearChatMessageProviderResponseIDsByChatID", reflect.TypeOf((*MockStore)(nil).ClearChatMessageProviderResponseIDsByChatID), ctx, chatID)
+}
+
 // CountAIBridgeInterceptions mocks base method.
 func (m *MockStore) CountAIBridgeInterceptions(ctx context.Context, arg database.CountAIBridgeInterceptionsParams) (int64, error) {
 	m.ctrl.T.Helper()
@@ -984,6 +998,36 @@ func (mr *MockStoreMockRecorder) DeleteOldAuditLogs(ctx, arg any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteOldAuditLogs", reflect.TypeOf((*MockStore)(nil).DeleteOldAuditLogs), ctx, arg)
 }
 
+// DeleteOldChatFiles mocks base method.
+func (m *MockStore) DeleteOldChatFiles(ctx context.Context, arg database.DeleteOldChatFilesParams) ([]database.DeleteOldChatFilesRow, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "DeleteOldChatFiles", ctx, arg)
+	ret0, _ := ret[0].([]database.DeleteOldChatFilesRow)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// DeleteOldChatFiles indicates an expected call of DeleteOldChatFiles.
+func (mr *MockStoreMockRecorder) DeleteOldChatFiles(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteOldChatFiles", reflect.TypeOf((*MockStore)(nil).DeleteOldChatFiles), ctx, arg)
+}
+
+// DeleteOldChats mocks base method.
+func (m *MockStore) DeleteOldChats(ctx context.Context, arg database.DeleteOldChatsParams) (int64, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "DeleteOldChats", ctx, arg)
+	ret0, _ := ret[0].(int64)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// DeleteOldChats indicates an expected call of DeleteOldChats.
+func (mr *MockStoreMockRecorder) DeleteOldChats(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteOldChats", reflect.TypeOf((*MockStore)(nil).DeleteOldChats), ctx, arg)
+}
+
 // DeleteOldConnectionLogs mocks base method.
 func (m *MockStore) DeleteOldConnectionLogs(ctx context.Context, arg database.DeleteOldConnectionLogsParams) (int64, error) {
 	m.ctrl.T.Helper()
@@ -1199,18 +1243,19 @@ func (mr *MockStoreMockRecorder) DeleteUserChatProviderKey(ctx, arg any) *gomock
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteUserChatProviderKey", reflect.TypeOf((*MockStore)(nil).DeleteUserChatProviderKey), ctx, arg)
 }
 
-// DeleteUserSecret mocks base method.
-func (m *MockStore) DeleteUserSecret(ctx context.Context, id uuid.UUID) error {
+// DeleteUserSecretByUserIDAndName mocks base method.
+func (m *MockStore) DeleteUserSecretByUserIDAndName(ctx context.Context, arg database.DeleteUserSecretByUserIDAndNameParams) (int64, error) {
 	m.ctrl.T.Helper()
-	ret := m.ctrl.Call(m, "DeleteUserSecret", ctx, id)
-	ret0, _ := ret[0].(error)
-	return ret0
+	ret := m.ctrl.Call(m, "DeleteUserSecretByUserIDAndName", ctx, arg)
+	ret0, _ := ret[0].(int64)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
 }
 
-// DeleteUserSecret indicates an expected call of DeleteUserSecret.
-func (mr *MockStoreMockRecorder) DeleteUserSecret(ctx, id any) *gomock.Call {
+// DeleteUserSecretByUserIDAndName indicates an expected call of DeleteUserSecretByUserIDAndName.
+func (mr *MockStoreMockRecorder) DeleteUserSecretByUserIDAndName(ctx, arg any) *gomock.Call {
 	mr.mock.ctrl.T.Helper()
-	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteUserSecret", reflect.TypeOf((*MockStore)(nil).DeleteUserSecret), ctx, id)
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteUserSecretByUserIDAndName", reflect.TypeOf((*MockStore)(nil).DeleteUserSecretByUserIDAndName), ctx, arg)
 }
 
 // DeleteWebpushSubscriptionByUserIDAndEndpoint mocks base method.
@@ -1637,6 +1682,21 @@ func (mr *MockStoreMockRecorder) GetActiveAISeatCount(ctx any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetActiveAISeatCount", reflect.TypeOf((*MockStore)(nil).GetActiveAISeatCount), ctx)
 }
 
+// GetActiveChatsByAgentID mocks base method.
+func (m *MockStore) GetActiveChatsByAgentID(ctx context.Context, agentID uuid.UUID) ([]database.Chat, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetActiveChatsByAgentID", ctx, agentID)
+	ret0, _ := ret[0].([]database.Chat)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetActiveChatsByAgentID indicates an expected call of GetActiveChatsByAgentID.
+func (mr *MockStoreMockRecorder) GetActiveChatsByAgentID(ctx, agentID any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetActiveChatsByAgentID", reflect.TypeOf((*MockStore)(nil).GetActiveChatsByAgentID), ctx, agentID)
+}
+
 // GetActivePresetPrebuildSchedules mocks base method.
 func (m *MockStore) GetActivePresetPrebuildSchedules(ctx context.Context) ([]database.TemplateVersionPresetPrebuildSchedule, error) {
 	m.ctrl.T.Helper()
@@ -2072,6 +2132,21 @@ func (mr *MockStoreMockRecorder) GetChatFileByID(ctx, id any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatFileByID", reflect.TypeOf((*MockStore)(nil).GetChatFileByID), ctx, id)
 }
 
+// GetChatFileMetadataByChatID mocks base method.
+func (m *MockStore) GetChatFileMetadataByChatID(ctx context.Context, chatID uuid.UUID) ([]database.GetChatFileMetadataByChatIDRow, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatFileMetadataByChatID", ctx, chatID)
+	ret0, _ := ret[0].([]database.GetChatFileMetadataByChatIDRow)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatFileMetadataByChatID indicates an expected call of GetChatFileMetadataByChatID.
+func (mr *MockStoreMockRecorder) GetChatFileMetadataByChatID(ctx, chatID any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatFileMetadataByChatID", reflect.TypeOf((*MockStore)(nil).GetChatFileMetadataByChatID), ctx, chatID)
+}
+
 // GetChatFilesByIDs mocks base method.
 func (m *MockStore) GetChatFilesByIDs(ctx context.Context, ids []uuid.UUID) ([]database.ChatFile, error) {
 	m.ctrl.T.Helper()
@@ -2117,6 +2192,21 @@ func (mr *MockStoreMockRecorder) GetChatMessageByID(ctx, id any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatMessageByID", reflect.TypeOf((*MockStore)(nil).GetChatMessageByID), ctx, id)
 }
 
+// GetChatMessageSummariesPerChat mocks base method.
+func (m *MockStore) GetChatMessageSummariesPerChat(ctx context.Context, createdAfter time.Time) ([]database.GetChatMessageSummariesPerChatRow, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatMessageSummariesPerChat", ctx, createdAfter)
+	ret0, _ := ret[0].([]database.GetChatMessageSummariesPerChatRow)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatMessageSummariesPerChat indicates an expected call of GetChatMessageSummariesPerChat.
+func (mr *MockStoreMockRecorder) GetChatMessageSummariesPerChat(ctx, createdAfter any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatMessageSummariesPerChat", reflect.TypeOf((*MockStore)(nil).GetChatMessageSummariesPerChat), ctx, createdAfter)
+}
+
 // GetChatMessagesByChatID mocks base method.
 func (m *MockStore) GetChatMessagesByChatID(ctx context.Context, arg database.GetChatMessagesByChatIDParams) ([]database.ChatMessage, error) {
 	m.ctrl.T.Helper()
@@ -2207,6 +2297,21 @@ func (mr *MockStoreMockRecorder) GetChatModelConfigs(ctx any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatModelConfigs", reflect.TypeOf((*MockStore)(nil).GetChatModelConfigs), ctx)
 }
 
+// GetChatModelConfigsForTelemetry mocks base method.
+func (m *MockStore) GetChatModelConfigsForTelemetry(ctx context.Context) ([]database.GetChatModelConfigsForTelemetryRow, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatModelConfigsForTelemetry", ctx)
+	ret0, _ := ret[0].([]database.GetChatModelConfigsForTelemetryRow)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatModelConfigsForTelemetry indicates an expected call of GetChatModelConfigsForTelemetry.
+func (mr *MockStoreMockRecorder) GetChatModelConfigsForTelemetry(ctx any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatModelConfigsForTelemetry", reflect.TypeOf((*MockStore)(nil).GetChatModelConfigsForTelemetry), ctx)
+}
+
 // GetChatProviderByID mocks base method.
 func (m *MockStore) GetChatProviderByID(ctx context.Context, id uuid.UUID) (database.ChatProvider, error) {
 	m.ctrl.T.Helper()
@@ -2267,6 +2372,21 @@ func (mr *MockStoreMockRecorder) GetChatQueuedMessages(ctx, chatID any) *gomock.
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatQueuedMessages", reflect.TypeOf((*MockStore)(nil).GetChatQueuedMessages), ctx, chatID)
 }
 
+// GetChatRetentionDays mocks base method.
+func (m *MockStore) GetChatRetentionDays(ctx context.Context) (int32, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatRetentionDays", ctx)
+	ret0, _ := ret[0].(int32)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatRetentionDays indicates an expected call of GetChatRetentionDays.
+func (mr *MockStoreMockRecorder) GetChatRetentionDays(ctx any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatRetentionDays", reflect.TypeOf((*MockStore)(nil).GetChatRetentionDays), ctx)
+}
+
 // GetChatSystemPrompt mocks base method.
 func (m *MockStore) GetChatSystemPrompt(ctx context.Context) (string, error) {
 	m.ctrl.T.Helper()
@@ -2402,6 +2522,21 @@ func (mr *MockStoreMockRecorder) GetChatsByWorkspaceIDs(ctx, ids any) *gomock.Ca
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatsByWorkspaceIDs", reflect.TypeOf((*MockStore)(nil).GetChatsByWorkspaceIDs), ctx, ids)
 }
 
+// GetChatsUpdatedAfter mocks base method.
+func (m *MockStore) GetChatsUpdatedAfter(ctx context.Context, updatedAfter time.Time) ([]database.GetChatsUpdatedAfterRow, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatsUpdatedAfter", ctx, updatedAfter)
+	ret0, _ := ret[0].([]database.GetChatsUpdatedAfterRow)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatsUpdatedAfter indicates an expected call of GetChatsUpdatedAfter.
+func (mr *MockStoreMockRecorder) GetChatsUpdatedAfter(ctx, updatedAfter any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatsUpdatedAfter", reflect.TypeOf((*MockStore)(nil).GetChatsUpdatedAfter), ctx, updatedAfter)
+}
+
 // GetConnectionLogsOffset mocks base method.
 func (m *MockStore) GetConnectionLogsOffset(ctx context.Context, arg database.GetConnectionLogsOffsetParams) ([]database.GetConnectionLogsOffsetRow, error) {
 	m.ctrl.T.Helper()
@@ -4892,21 +5027,6 @@ func (mr *MockStoreMockRecorder) GetUserNotificationPreferences(ctx, userID any)
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetUserNotificationPreferences", reflect.TypeOf((*MockStore)(nil).GetUserNotificationPreferences), ctx, userID)
 }
 
-// GetUserSecret mocks base method.
-func (m *MockStore) GetUserSecret(ctx context.Context, id uuid.UUID) (database.UserSecret, error) {
-	m.ctrl.T.Helper()
-	ret := m.ctrl.Call(m, "GetUserSecret", ctx, id)
-	ret0, _ := ret[0].(database.UserSecret)
-	ret1, _ := ret[1].(error)
-	return ret0, ret1
-}
-
-// GetUserSecret indicates an expected call of GetUserSecret.
-func (mr *MockStoreMockRecorder) GetUserSecret(ctx, id any) *gomock.Call {
-	mr.mock.ctrl.T.Helper()
-	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetUserSecret", reflect.TypeOf((*MockStore)(nil).GetUserSecret), ctx, id)
-}
-
 // GetUserSecretByUserIDAndName mocks base method.
 func (m *MockStore) GetUserSecretByUserIDAndName(ctx context.Context, arg database.GetUserSecretByUserIDAndNameParams) (database.UserSecret, error) {
 	m.ctrl.T.Helper()
@@ -7066,6 +7186,21 @@ func (mr *MockStoreMockRecorder) InsertWorkspaceResourceMetadata(ctx, arg any) *
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "InsertWorkspaceResourceMetadata", reflect.TypeOf((*MockStore)(nil).InsertWorkspaceResourceMetadata), ctx, arg)
 }
 
+// LinkChatFiles mocks base method.
+func (m *MockStore) LinkChatFiles(ctx context.Context, arg database.LinkChatFilesParams) (int32, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "LinkChatFiles", ctx, arg)
+	ret0, _ := ret[0].(int32)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// LinkChatFiles indicates an expected call of LinkChatFiles.
+func (mr *MockStoreMockRecorder) LinkChatFiles(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "LinkChatFiles", reflect.TypeOf((*MockStore)(nil).LinkChatFiles), ctx, arg)
+}
+
 // ListAIBridgeClients mocks base method.
 func (m *MockStore) ListAIBridgeClients(ctx context.Context, arg database.ListAIBridgeClientsParams) ([]string, error) {
 	m.ctrl.T.Helper()
@@ -7382,10 +7517,10 @@ func (mr *MockStoreMockRecorder) ListUserChatCompactionThresholds(ctx, userID an
 }
 
 // ListUserSecrets mocks base method.
-func (m *MockStore) ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]database.UserSecret, error) {
+func (m *MockStore) ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]database.ListUserSecretsRow, error) {
 	m.ctrl.T.Helper()
 	ret := m.ctrl.Call(m, "ListUserSecrets", ctx, userID)
-	ret0, _ := ret[0].([]database.UserSecret)
+	ret0, _ := ret[0].([]database.ListUserSecretsRow)
 	ret1, _ := ret[1].(error)
 	return ret0, ret1
 }
@@ -7396,6 +7531,21 @@ func (mr *MockStoreMockRecorder) ListUserSecrets(ctx, userID any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "ListUserSecrets", reflect.TypeOf((*MockStore)(nil).ListUserSecrets), ctx, userID)
 }
 
+// ListUserSecretsWithValues mocks base method.
+func (m *MockStore) ListUserSecretsWithValues(ctx context.Context, userID uuid.UUID) ([]database.UserSecret, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "ListUserSecretsWithValues", ctx, userID)
+	ret0, _ := ret[0].([]database.UserSecret)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// ListUserSecretsWithValues indicates an expected call of ListUserSecretsWithValues.
+func (mr *MockStoreMockRecorder) ListUserSecretsWithValues(ctx, userID any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "ListUserSecretsWithValues", reflect.TypeOf((*MockStore)(nil).ListUserSecretsWithValues), ctx, userID)
+}
+
 // ListWorkspaceAgentPortShares mocks base method.
 func (m *MockStore) ListWorkspaceAgentPortShares(ctx context.Context, workspaceID uuid.UUID) ([]database.WorkspaceAgentPortShare, error) {
 	m.ctrl.T.Helper()
@@ -7660,6 +7810,20 @@ func (mr *MockStoreMockRecorder) SoftDeleteChatMessagesAfterID(ctx, arg any) *go
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "SoftDeleteChatMessagesAfterID", reflect.TypeOf((*MockStore)(nil).SoftDeleteChatMessagesAfterID), ctx, arg)
 }
 
+// SoftDeleteContextFileMessages mocks base method.
+func (m *MockStore) SoftDeleteContextFileMessages(ctx context.Context, chatID uuid.UUID) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "SoftDeleteContextFileMessages", ctx, chatID)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// SoftDeleteContextFileMessages indicates an expected call of SoftDeleteContextFileMessages.
+func (mr *MockStoreMockRecorder) SoftDeleteContextFileMessages(ctx, chatID any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "SoftDeleteContextFileMessages", reflect.TypeOf((*MockStore)(nil).SoftDeleteContextFileMessages), ctx, chatID)
+}
+
 // TryAcquireLock mocks base method.
 func (m *MockStore) TryAcquireLock(ctx context.Context, pgTryAdvisoryXactLock int64) (bool, error) {
 	m.ctrl.T.Helper()
@@ -7805,19 +7969,19 @@ 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.
@@ -8824,19 +8988,19 @@ func (mr *MockStoreMockRecorder) UpdateUserRoles(ctx, arg any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateUserRoles", reflect.TypeOf((*MockStore)(nil).UpdateUserRoles), ctx, arg)
 }
 
-// UpdateUserSecret mocks base method.
-func (m *MockStore) UpdateUserSecret(ctx context.Context, arg database.UpdateUserSecretParams) (database.UserSecret, error) {
+// UpdateUserSecretByUserIDAndName mocks base method.
+func (m *MockStore) UpdateUserSecretByUserIDAndName(ctx context.Context, arg database.UpdateUserSecretByUserIDAndNameParams) (database.UserSecret, error) {
 	m.ctrl.T.Helper()
-	ret := m.ctrl.Call(m, "UpdateUserSecret", ctx, arg)
+	ret := m.ctrl.Call(m, "UpdateUserSecretByUserIDAndName", ctx, arg)
 	ret0, _ := ret[0].(database.UserSecret)
 	ret1, _ := ret[1].(error)
 	return ret0, ret1
 }
 
-// UpdateUserSecret indicates an expected call of UpdateUserSecret.
-func (mr *MockStoreMockRecorder) UpdateUserSecret(ctx, arg any) *gomock.Call {
+// UpdateUserSecretByUserIDAndName indicates an expected call of UpdateUserSecretByUserIDAndName.
+func (mr *MockStoreMockRecorder) UpdateUserSecretByUserIDAndName(ctx, arg any) *gomock.Call {
 	mr.mock.ctrl.T.Helper()
-	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateUserSecret", reflect.TypeOf((*MockStore)(nil).UpdateUserSecret), ctx, arg)
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateUserSecretByUserIDAndName", reflect.TypeOf((*MockStore)(nil).UpdateUserSecretByUserIDAndName), ctx, arg)
 }
 
 // UpdateUserStatus mocks base method.
@@ -9369,6 +9533,20 @@ func (mr *MockStoreMockRecorder) UpsertChatIncludeDefaultSystemPrompt(ctx, inclu
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpsertChatIncludeDefaultSystemPrompt", reflect.TypeOf((*MockStore)(nil).UpsertChatIncludeDefaultSystemPrompt), ctx, includeDefaultSystemPrompt)
 }
 
+// UpsertChatRetentionDays mocks base method.
+func (m *MockStore) UpsertChatRetentionDays(ctx context.Context, retentionDays int32) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "UpsertChatRetentionDays", ctx, retentionDays)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// UpsertChatRetentionDays indicates an expected call of UpsertChatRetentionDays.
+func (mr *MockStoreMockRecorder) UpsertChatRetentionDays(ctx, retentionDays any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpsertChatRetentionDays", reflect.TypeOf((*MockStore)(nil).UpsertChatRetentionDays), ctx, retentionDays)
+}
+
 // UpsertChatSystemPrompt mocks base method.
 func (m *MockStore) UpsertChatSystemPrompt(ctx context.Context, value string) error {
 	m.ctrl.T.Helper()

coderd/database/dbpurge/dbpurge.go

@@ -3,6 +3,7 @@ package dbpurge
 import (
 	"context"
 	"io"
+	"sync"
 	"time"
 
 	"github.com/prometheus/client_golang/prometheus"
@@ -12,6 +13,7 @@ import (
 	"github.com/coder/coder/v2/coderd/database"
 	"github.com/coder/coder/v2/coderd/database/dbauthz"
 	"github.com/coder/coder/v2/coderd/database/dbtime"
+	"github.com/coder/coder/v2/coderd/objstore"
 	"github.com/coder/coder/v2/coderd/pproflabel"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/quartz"
@@ -34,13 +36,22 @@ const (
 	// long enough to cover the maximum interval of a heartbeat event (currently
 	// 1 hour) plus some buffer.
 	maxTelemetryHeartbeatAge = 24 * time.Hour
+	// Batch sizes for chat purging. Both use 1000, which is smaller
+	// than audit/connection log batches (10000), because chat_files
+	// rows contain bytea blob data that make large batches heavier.
+	chatsBatchSize     = 1000
+	chatFilesBatchSize = 1000
 )
 
+// chatFilesNamespace is the object store namespace under which chat
+// files are stored.
+const chatFilesNamespace = "chatfiles"
+
 // New creates a new periodically purging database instance.
 // It is the caller's responsibility to call Close on the returned instance.
 //
 // This is for cleaning up old, unused resources from the database that take up space.
-func New(ctx context.Context, logger slog.Logger, db database.Store, vals *codersdk.DeploymentValues, clk quartz.Clock, reg prometheus.Registerer) io.Closer {
+func New(ctx context.Context, logger slog.Logger, db database.Store, vals *codersdk.DeploymentValues, clk quartz.Clock, reg prometheus.Registerer, objStore objstore.Store) io.Closer {
 	closed := make(chan struct{})
 
 	ctx, cancelFunc := context.WithCancel(ctx)
@@ -64,6 +75,22 @@ func New(ctx context.Context, logger slog.Logger, db database.Store, vals *coder
 	}, []string{"record_type"})
 	reg.MustRegister(recordsPurged)
 
+	objStoreInflight := prometheus.NewGauge(prometheus.GaugeOpts{
+		Namespace: "coderd",
+		Subsystem: "dbpurge",
+		Name:      "objstore_delete_inflight",
+		Help:      "Number of object store files currently enqueued for deletion.",
+	})
+	reg.MustRegister(objStoreInflight)
+
+	objStoreDeleted := prometheus.NewCounter(prometheus.CounterOpts{
+		Namespace: "coderd",
+		Subsystem: "dbpurge",
+		Name:      "objstore_files_deleted_total",
+		Help:      "Total number of object store files successfully deleted.",
+	})
+	reg.MustRegister(objStoreDeleted)
+
 	inst := &instance{
 		cancel:            cancelFunc,
 		closed:            closed,
@@ -72,6 +99,9 @@ func New(ctx context.Context, logger slog.Logger, db database.Store, vals *coder
 		clk:               clk,
 		iterationDuration: iterationDuration,
 		recordsPurged:     recordsPurged,
+		objStore:          objStore,
+		objStoreInflight:  objStoreInflight,
+		objStoreDeleted:   objStoreDeleted,
 	}
 
 	// Start the ticker with the initial delay.
@@ -109,6 +139,17 @@ func New(ctx context.Context, logger slog.Logger, db database.Store, vals *coder
 // purgeTick performs a single purge iteration. It returns an error if the
 // purge fails.
 func (i *instance) purgeTick(ctx context.Context, db database.Store, start time.Time) error {
+	// Read chat retention config outside the transaction to
+	// avoid poisoning the tx if the stored value is corrupt.
+	// A SQL-level cast error (e.g. non-numeric text) puts PG
+	// into error state, failing all subsequent queries in the
+	// same transaction.
+	chatRetentionDays, err := db.GetChatRetentionDays(ctx)
+	if err != nil {
+		i.logger.Warn(ctx, "failed to read chat retention config, skipping chat purge", slog.Error(err))
+		chatRetentionDays = 0
+	}
+
 	// Start a transaction to grab advisory lock, we don't want to run
 	// multiple purges at the same time (multiple replicas).
 	return db.InTx(func(tx database.Store) error {
@@ -213,12 +254,50 @@ func (i *instance) purgeTick(ctx context.Context, db database.Store, start time.
 			}
 		}
 
+		// Chat retention is configured via site_configs. When
+		// enabled, old archived chats are deleted first, then
+		// orphaned chat files. Deleting a chat cascades to
+		// chat_file_links (removing references) but not to
+		// chat_files directly, so files from deleted chats
+		// become orphaned and are caught by DeleteOldChatFiles
+		// in the same tick.
+		var purgedChats int64
+		var purgedChatFiles int64
+		if chatRetentionDays > 0 {
+			chatRetention := time.Duration(chatRetentionDays) * 24 * time.Hour
+			deleteChatsBefore := start.Add(-chatRetention)
+
+			purgedChats, err = tx.DeleteOldChats(ctx, database.DeleteOldChatsParams{
+				BeforeTime: deleteChatsBefore,
+				LimitCount: chatsBatchSize,
+			})
+			if err != nil {
+				return xerrors.Errorf("failed to delete old chats: %w", err)
+			}
+
+			deletedFiles, err := tx.DeleteOldChatFiles(ctx, database.DeleteOldChatFilesParams{
+				BeforeTime: deleteChatsBefore,
+				LimitCount: chatFilesBatchSize,
+			})
+			if err != nil {
+				return xerrors.Errorf("failed to delete old chat files: %w", err)
+			}
+			purgedChatFiles = int64(len(deletedFiles))
+
+			// Collect object store keys from the deleted rows
+			// and delete them in a background goroutine so
+			// slow object store I/O does not hold the
+			// advisory lock or block the next tick.
+			i.deleteObjStoreKeys(ctx, deletedFiles)
+		}
 		i.logger.Debug(ctx, "purged old database entries",
 			slog.F("workspace_agent_logs", purgedWorkspaceAgentLogs),
 			slog.F("expired_api_keys", expiredAPIKeys),
 			slog.F("aibridge_records", purgedAIBridgeRecords),
 			slog.F("connection_logs", purgedConnectionLogs),
 			slog.F("audit_logs", purgedAuditLogs),
+			slog.F("chats", purgedChats),
+			slog.F("chat_files", purgedChatFiles),
 			slog.F("duration", i.clk.Since(start)),
 		)
 
@@ -232,6 +311,8 @@ func (i *instance) purgeTick(ctx context.Context, db database.Store, start time.
 			i.recordsPurged.WithLabelValues("aibridge_records").Add(float64(purgedAIBridgeRecords))
 			i.recordsPurged.WithLabelValues("connection_logs").Add(float64(purgedConnectionLogs))
 			i.recordsPurged.WithLabelValues("audit_logs").Add(float64(purgedAuditLogs))
+			i.recordsPurged.WithLabelValues("chats").Add(float64(purgedChats))
+			i.recordsPurged.WithLabelValues("chat_files").Add(float64(purgedChatFiles))
 		}
 
 		return nil
@@ -246,6 +327,13 @@ type instance struct {
 	clk               quartz.Clock
 	iterationDuration *prometheus.HistogramVec
 	recordsPurged     *prometheus.CounterVec
+	objStore          objstore.Store
+	objStoreInflight  prometheus.Gauge
+	objStoreDeleted   prometheus.Counter
+
+	// objDeleteMu serializes background object store delete batches
+	// so at most one goroutine is deleting at a time.
+	objDeleteMu sync.Mutex
 }
 
 func (i *instance) Close() error {
@@ -253,3 +341,62 @@ func (i *instance) Close() error {
 	<-i.closed
 	return nil
 }
+
+// deleteObjStoreKeys removes object store entries for the given
+// deleted chat file rows. The work runs in a background goroutine
+// guarded by a mutex so that slow object store I/O never blocks
+// the purge transaction or the next tick. At most one delete batch
+// runs at a time; if a batch is already in flight the new keys are
+// silently dropped (they will be orphan-collected on a future tick
+// if needed).
+func (i *instance) deleteObjStoreKeys(ctx context.Context, rows []database.DeleteOldChatFilesRow) {
+	// Collect non-empty object store keys.
+	var keys []string
+	for _, r := range rows {
+		if r.ObjectStoreKey.Valid && r.ObjectStoreKey.String != "" {
+			keys = append(keys, r.ObjectStoreKey.String)
+		}
+	}
+	if len(keys) == 0 {
+		return
+	}
+
+	// Try to acquire the mutex without blocking. If another
+	// delete batch is already running, skip this one.
+	if !i.objDeleteMu.TryLock() {
+		i.logger.Debug(ctx, "object store delete already in progress, skipping batch",
+			slog.F("skipped_keys", len(keys)))
+		return
+	}
+
+	i.objStoreInflight.Add(float64(len(keys)))
+
+	go func() {
+		defer i.objDeleteMu.Unlock()
+
+		var deleted int
+		for _, key := range keys {
+			if ctx.Err() != nil {
+				remaining := len(keys) - deleted
+				i.objStoreInflight.Sub(float64(remaining))
+				i.logger.Debug(ctx, "context canceled during object store cleanup",
+					slog.F("deleted", deleted),
+					slog.F("remaining", remaining))
+				return
+			}
+			if err := i.objStore.Delete(ctx, chatFilesNamespace, key); err != nil {
+				i.logger.Warn(ctx, "failed to delete chat file from object store",
+					slog.F("key", key),
+					slog.Error(err))
+			} else {
+				deleted++
+			}
+			i.objStoreInflight.Dec()
+		}
+
+		i.objStoreDeleted.Add(float64(deleted))
+		i.logger.Debug(ctx, "deleted chat files from object store",
+			slog.F("deleted", deleted),
+			slog.F("failed", len(keys)-deleted))
+	}()
+}

coderd/database/dbpurge/dbpurge_test.go

@@ -12,6 +12,7 @@ import (
 	"time"
 
 	"github.com/google/uuid"
+	"github.com/lib/pq"
 	"github.com/prometheus/client_golang/prometheus"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
@@ -53,8 +54,9 @@ func TestPurge(t *testing.T) {
 	clk := quartz.NewMock(t)
 	done := awaitDoTick(ctx, t, clk)
 	mDB := dbmock.NewMockStore(gomock.NewController(t))
+	mDB.EXPECT().GetChatRetentionDays(gomock.Any()).Return(int32(0), nil).AnyTimes()
 	mDB.EXPECT().InTx(gomock.Any(), database.DefaultTXOptions().WithID("db_purge")).Return(nil).Times(2)
-	purger := dbpurge.New(context.Background(), testutil.Logger(t), mDB, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry())
+	purger := dbpurge.New(context.Background(), testutil.Logger(t), mDB, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry(), nil)
 	<-done // wait for doTick() to run.
 	require.NoError(t, purger.Close())
 }
@@ -88,7 +90,7 @@ func TestMetrics(t *testing.T) {
 			Retention: codersdk.RetentionConfig{
 				APIKeys: serpent.Duration(7 * 24 * time.Hour), // 7 days retention
 			},
-		}, clk, reg)
+		}, clk, reg, nil)
 		defer closer.Close()
 		testutil.TryReceive(ctx, t, done)
 
@@ -125,6 +127,16 @@ func TestMetrics(t *testing.T) {
 			"record_type": "audit_logs",
 		})
 		require.GreaterOrEqual(t, auditLogs, 0)
+
+		chats := promhelp.CounterValue(t, reg, "coderd_dbpurge_records_purged_total", prometheus.Labels{
+			"record_type": "chats",
+		})
+		require.GreaterOrEqual(t, chats, 0)
+
+		chatFiles := promhelp.CounterValue(t, reg, "coderd_dbpurge_records_purged_total", prometheus.Labels{
+			"record_type": "chat_files",
+		})
+		require.GreaterOrEqual(t, chatFiles, 0)
 	})
 
 	t.Run("FailedIteration", func(t *testing.T) {
@@ -138,6 +150,7 @@ func TestMetrics(t *testing.T) {
 
 		ctrl := gomock.NewController(t)
 		mDB := dbmock.NewMockStore(ctrl)
+		mDB.EXPECT().GetChatRetentionDays(gomock.Any()).Return(int32(0), nil).AnyTimes()
 		mDB.EXPECT().InTx(gomock.Any(), database.DefaultTXOptions().WithID("db_purge")).
 			Return(xerrors.New("simulated database error")).
 			MinTimes(1)
@@ -145,7 +158,7 @@ func TestMetrics(t *testing.T) {
 		logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
 
 		done := awaitDoTick(ctx, t, clk)
-		closer := dbpurge.New(ctx, logger, mDB, &codersdk.DeploymentValues{}, clk, reg)
+		closer := dbpurge.New(ctx, logger, mDB, &codersdk.DeploymentValues{}, clk, reg, nil)
 		defer closer.Close()
 		testutil.TryReceive(ctx, t, done)
 
@@ -235,7 +248,7 @@ func TestDeleteOldWorkspaceAgentStats(t *testing.T) {
 	})
 
 	// when
-	closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry())
+	closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry(), nil)
 	defer closer.Close()
 
 	// then
@@ -260,7 +273,7 @@ func TestDeleteOldWorkspaceAgentStats(t *testing.T) {
 
 	// Start a new purger to immediately trigger delete after rollup.
 	_ = closer.Close()
-	closer = dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry())
+	closer = dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry(), nil)
 	defer closer.Close()
 
 	// then
@@ -355,7 +368,7 @@ func TestDeleteOldWorkspaceAgentLogs(t *testing.T) {
 		Retention: codersdk.RetentionConfig{
 			WorkspaceAgentLogs: serpent.Duration(7 * 24 * time.Hour),
 		},
-	}, clk, prometheus.NewRegistry())
+	}, clk, prometheus.NewRegistry(), nil)
 
 	defer closer.Close()
 	<-done // doTick() has now run.
@@ -570,7 +583,7 @@ func TestDeleteOldWorkspaceAgentLogsRetention(t *testing.T) {
 			done := awaitDoTick(ctx, t, clk)
 			closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{
 				Retention: tc.retentionConfig,
-			}, clk, prometheus.NewRegistry())
+			}, clk, prometheus.NewRegistry(), nil)
 			defer closer.Close()
 			testutil.TryReceive(ctx, t, done)
 
@@ -661,7 +674,7 @@ func TestDeleteOldProvisionerDaemons(t *testing.T) {
 	require.NoError(t, err)
 
 	// when
-	closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry())
+	closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry(), nil)
 	defer closer.Close()
 
 	// then
@@ -765,7 +778,7 @@ func TestDeleteOldAuditLogConnectionEvents(t *testing.T) {
 
 	// Run the purge
 	done := awaitDoTick(ctx, t, clk)
-	closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry())
+	closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry(), nil)
 	defer closer.Close()
 	// Wait for tick
 	testutil.TryReceive(ctx, t, done)
@@ -928,7 +941,7 @@ func TestDeleteOldTelemetryHeartbeats(t *testing.T) {
 	require.NoError(t, err)
 
 	done := awaitDoTick(ctx, t, clk)
-	closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry())
+	closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry(), nil)
 	defer closer.Close()
 	<-done // doTick() has now run.
 
@@ -1047,7 +1060,7 @@ func TestDeleteOldConnectionLogs(t *testing.T) {
 			done := awaitDoTick(ctx, t, clk)
 			closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{
 				Retention: tc.retentionConfig,
-			}, clk, prometheus.NewRegistry())
+			}, clk, prometheus.NewRegistry(), nil)
 			defer closer.Close()
 			testutil.TryReceive(ctx, t, done)
 
@@ -1303,7 +1316,7 @@ func TestDeleteOldAIBridgeRecords(t *testing.T) {
 						Retention: serpent.Duration(tc.retention),
 					},
 				},
-			}, clk, prometheus.NewRegistry())
+			}, clk, prometheus.NewRegistry(), nil)
 			defer closer.Close()
 			testutil.TryReceive(ctx, t, done)
 
@@ -1390,7 +1403,7 @@ func TestDeleteOldAuditLogs(t *testing.T) {
 			done := awaitDoTick(ctx, t, clk)
 			closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{
 				Retention: tc.retentionConfig,
-			}, clk, prometheus.NewRegistry())
+			}, clk, prometheus.NewRegistry(), nil)
 			defer closer.Close()
 			testutil.TryReceive(ctx, t, done)
 
@@ -1480,7 +1493,7 @@ func TestDeleteOldAuditLogs(t *testing.T) {
 			Retention: codersdk.RetentionConfig{
 				AuditLogs: serpent.Duration(retentionPeriod),
 			},
-		}, clk, prometheus.NewRegistry())
+		}, clk, prometheus.NewRegistry(), nil)
 		defer closer.Close()
 		testutil.TryReceive(ctx, t, done)
 
@@ -1600,7 +1613,7 @@ func TestDeleteExpiredAPIKeys(t *testing.T) {
 			done := awaitDoTick(ctx, t, clk)
 			closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{
 				Retention: tc.retentionConfig,
-			}, clk, prometheus.NewRegistry())
+			}, clk, prometheus.NewRegistry(), nil)
 			defer closer.Close()
 			testutil.TryReceive(ctx, t, done)
 
@@ -1634,3 +1647,488 @@ func TestDeleteExpiredAPIKeys(t *testing.T) {
 func ptr[T any](v T) *T {
 	return &v
 }
+
+//nolint:paralleltest // It uses LockIDDBPurge.
+func TestDeleteOldChatFiles(t *testing.T) {
+	now := time.Date(2025, 6, 15, 12, 0, 0, 0, time.UTC)
+
+	// createChatFile inserts a chat file and backdates created_at.
+	createChatFile := func(ctx context.Context, t *testing.T, db database.Store, rawDB *sql.DB, ownerID, orgID uuid.UUID, createdAt time.Time) uuid.UUID {
+		t.Helper()
+		row, err := db.InsertChatFile(ctx, database.InsertChatFileParams{
+			OwnerID:        ownerID,
+			OrganizationID: orgID,
+			Name:           "test.png",
+			Mimetype:       "image/png",
+			Data:           []byte("fake-image-data"),
+		})
+		require.NoError(t, err)
+		_, err = rawDB.ExecContext(ctx, "UPDATE chat_files SET created_at = $1 WHERE id = $2", createdAt, row.ID)
+		require.NoError(t, err)
+		return row.ID
+	}
+
+	// createChat inserts a chat and optionally archives it, then
+	// backdates updated_at to control the "archived since" window.
+	createChat := func(ctx context.Context, t *testing.T, db database.Store, rawDB *sql.DB, ownerID, modelConfigID uuid.UUID, archived bool, updatedAt time.Time) database.Chat {
+		t.Helper()
+		chat, err := db.InsertChat(ctx, database.InsertChatParams{
+			OwnerID:           ownerID,
+			LastModelConfigID: modelConfigID,
+			Title:             "test-chat",
+			Status:            database.ChatStatusWaiting,
+		})
+		require.NoError(t, err)
+		if archived {
+			_, err = db.ArchiveChatByID(ctx, chat.ID)
+			require.NoError(t, err)
+		}
+		_, err = rawDB.ExecContext(ctx, "UPDATE chats SET updated_at = $1 WHERE id = $2", updatedAt, chat.ID)
+		require.NoError(t, err)
+		return chat
+	}
+	// setupChatDeps creates the common dependencies needed for
+	// chat-related tests: user, org, org member, provider, model config.
+	type chatDeps struct {
+		user        database.User
+		org         database.Organization
+		modelConfig database.ChatModelConfig
+	}
+	setupChatDeps := func(ctx context.Context, t *testing.T, db database.Store) chatDeps {
+		t.Helper()
+		user := dbgen.User(t, db, database.User{})
+		org := dbgen.Organization(t, db, database.Organization{})
+		_ = dbgen.OrganizationMember(t, db, database.OrganizationMember{UserID: user.ID, OrganizationID: org.ID})
+		_, err := db.InsertChatProvider(ctx, database.InsertChatProviderParams{
+			Provider:             "openai",
+			DisplayName:          "OpenAI",
+			Enabled:              true,
+			CentralApiKeyEnabled: true,
+		})
+		require.NoError(t, err)
+		mc, err := db.InsertChatModelConfig(ctx, database.InsertChatModelConfigParams{
+			Provider:     "openai",
+			Model:        "test-model",
+			ContextLimit: 8192,
+			Options:      json.RawMessage("{}"),
+		})
+		require.NoError(t, err)
+		return chatDeps{user: user, org: org, modelConfig: mc}
+	}
+
+	tests := []struct {
+		name string
+		run  func(t *testing.T)
+	}{
+		{
+			name: "ChatRetentionDisabled",
+			run: func(t *testing.T) {
+				ctx := testutil.Context(t, testutil.WaitLong)
+				clk := quartz.NewMock(t)
+				clk.Set(now).MustWait(ctx)
+
+				db, _, rawDB := dbtestutil.NewDBWithSQLDB(t, dbtestutil.WithDumpOnFailure())
+				logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+				deps := setupChatDeps(ctx, t, db)
+
+				// Disable retention.
+				err := db.UpsertChatRetentionDays(ctx, int32(0))
+				require.NoError(t, err)
+
+				// Create an old archived chat and an orphaned old file.
+				oldChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, true, now.Add(-31*24*time.Hour))
+				oldFileID := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-31*24*time.Hour))
+
+				done := awaitDoTick(ctx, t, clk)
+				closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry(), nil)
+				defer closer.Close()
+				testutil.TryReceive(ctx, t, done)
+
+				// Both should still exist.
+				_, err = db.GetChatByID(ctx, oldChat.ID)
+				require.NoError(t, err, "chat should not be deleted when retention is disabled")
+				_, err = db.GetChatFileByID(ctx, oldFileID)
+				require.NoError(t, err, "chat file should not be deleted when retention is disabled")
+			},
+		},
+		{
+			name: "OldArchivedChatsDeleted",
+			run: func(t *testing.T) {
+				ctx := testutil.Context(t, testutil.WaitLong)
+				clk := quartz.NewMock(t)
+				clk.Set(now).MustWait(ctx)
+
+				db, _, rawDB := dbtestutil.NewDBWithSQLDB(t, dbtestutil.WithDumpOnFailure())
+				logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+				deps := setupChatDeps(ctx, t, db)
+
+				err := db.UpsertChatRetentionDays(ctx, int32(30))
+				require.NoError(t, err)
+
+				// Old archived chat (31 days) — should be deleted.
+				oldChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, true, now.Add(-31*24*time.Hour))
+				// Insert a message so we can verify CASCADE.
+				_, err = db.InsertChatMessages(ctx, database.InsertChatMessagesParams{
+					ChatID:              oldChat.ID,
+					CreatedBy:           []uuid.UUID{deps.user.ID},
+					ModelConfigID:       []uuid.UUID{deps.modelConfig.ID},
+					Role:                []database.ChatMessageRole{database.ChatMessageRoleUser},
+					Content:             []string{`[{"type":"text","text":"hello"}]`},
+					ContentVersion:      []int16{0},
+					Visibility:          []database.ChatMessageVisibility{database.ChatMessageVisibilityBoth},
+					InputTokens:         []int64{0},
+					OutputTokens:        []int64{0},
+					TotalTokens:         []int64{0},
+					ReasoningTokens:     []int64{0},
+					CacheCreationTokens: []int64{0},
+					CacheReadTokens:     []int64{0},
+					ContextLimit:        []int64{0},
+					Compressed:          []bool{false},
+					TotalCostMicros:     []int64{0},
+					RuntimeMs:           []int64{0},
+					ProviderResponseID:  []string{""},
+				})
+				require.NoError(t, err)
+
+				// Recently archived chat (10 days) — should be retained.
+				recentChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, true, now.Add(-10*24*time.Hour))
+
+				// Active chat — should be retained.
+				activeChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, false, now)
+
+				done := awaitDoTick(ctx, t, clk)
+				closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry(), nil)
+				defer closer.Close()
+				testutil.TryReceive(ctx, t, done)
+
+				// Old archived chat should be gone.
+				_, err = db.GetChatByID(ctx, oldChat.ID)
+				require.Error(t, err, "old archived chat should be deleted")
+
+				// Its messages should be gone too (CASCADE).
+				msgs, err := db.GetChatMessagesByChatID(ctx, database.GetChatMessagesByChatIDParams{
+					ChatID:  oldChat.ID,
+					AfterID: 0,
+				})
+				require.NoError(t, err)
+				require.Empty(t, msgs, "messages should be cascade-deleted")
+
+				// Recent archived and active chats should remain.
+				_, err = db.GetChatByID(ctx, recentChat.ID)
+				require.NoError(t, err, "recently archived chat should be retained")
+				_, err = db.GetChatByID(ctx, activeChat.ID)
+				require.NoError(t, err, "active chat should be retained")
+			},
+		},
+		{
+			name: "OrphanedOldFilesDeleted",
+			run: func(t *testing.T) {
+				ctx := testutil.Context(t, testutil.WaitLong)
+				clk := quartz.NewMock(t)
+				clk.Set(now).MustWait(ctx)
+
+				db, _, rawDB := dbtestutil.NewDBWithSQLDB(t, dbtestutil.WithDumpOnFailure())
+				logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+				deps := setupChatDeps(ctx, t, db)
+
+				err := db.UpsertChatRetentionDays(ctx, int32(30))
+				require.NoError(t, err)
+
+				// File A: 31 days old, NOT in any chat -> should be deleted.
+				fileA := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-31*24*time.Hour))
+
+				// File B: 31 days old, in an active chat -> should be retained.
+				fileB := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-31*24*time.Hour))
+				activeChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, false, now)
+				_, err = db.LinkChatFiles(ctx, database.LinkChatFilesParams{
+					ChatID:       activeChat.ID,
+					MaxFileLinks: 100,
+					FileIds:      []uuid.UUID{fileB},
+				})
+				require.NoError(t, err)
+
+				// File C: 10 days old, NOT in any chat -> should be retained (too young).
+				fileC := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-10*24*time.Hour))
+
+				// File near boundary: 29d23h old — close to threshold.
+				fileBoundary := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-30*24*time.Hour).Add(time.Hour))
+
+				done := awaitDoTick(ctx, t, clk)
+				closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry(), nil)
+				defer closer.Close()
+				testutil.TryReceive(ctx, t, done)
+
+				_, err = db.GetChatFileByID(ctx, fileA)
+				require.Error(t, err, "orphaned old file A should be deleted")
+
+				_, err = db.GetChatFileByID(ctx, fileB)
+				require.NoError(t, err, "file B in active chat should be retained")
+
+				_, err = db.GetChatFileByID(ctx, fileC)
+				require.NoError(t, err, "young file C should be retained")
+
+				_, err = db.GetChatFileByID(ctx, fileBoundary)
+				require.NoError(t, err, "file near 30d boundary should be retained")
+			},
+		},
+		{
+			name: "ArchivedChatFilesDeleted",
+			run: func(t *testing.T) {
+				ctx := testutil.Context(t, testutil.WaitLong)
+				clk := quartz.NewMock(t)
+				clk.Set(now).MustWait(ctx)
+
+				db, _, rawDB := dbtestutil.NewDBWithSQLDB(t, dbtestutil.WithDumpOnFailure())
+				logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+				deps := setupChatDeps(ctx, t, db)
+
+				err := db.UpsertChatRetentionDays(ctx, int32(30))
+				require.NoError(t, err)
+
+				// File D: 31 days old, in a chat archived 31 days ago -> should be deleted.
+				fileD := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-31*24*time.Hour))
+				oldArchivedChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, true, now.Add(-31*24*time.Hour))
+				_, err = db.LinkChatFiles(ctx, database.LinkChatFilesParams{
+					ChatID:       oldArchivedChat.ID,
+					MaxFileLinks: 100,
+					FileIds:      []uuid.UUID{fileD},
+				})
+				require.NoError(t, err)
+				// LinkChatFiles does not update chats.updated_at, so backdate.
+				_, err = rawDB.ExecContext(ctx, "UPDATE chats SET updated_at = $1 WHERE id = $2",
+					now.Add(-31*24*time.Hour), oldArchivedChat.ID)
+				require.NoError(t, err)
+
+				// File E: 31 days old, in a chat archived 10 days ago -> should be retained.
+				fileE := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-31*24*time.Hour))
+				recentArchivedChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, true, now.Add(-10*24*time.Hour))
+				_, err = db.LinkChatFiles(ctx, database.LinkChatFilesParams{
+					ChatID:       recentArchivedChat.ID,
+					MaxFileLinks: 100,
+					FileIds:      []uuid.UUID{fileE},
+				})
+				require.NoError(t, err)
+				_, err = rawDB.ExecContext(ctx, "UPDATE chats SET updated_at = $1 WHERE id = $2",
+					now.Add(-10*24*time.Hour), recentArchivedChat.ID)
+				require.NoError(t, err)
+
+				// File F: 31 days old, in BOTH an active chat AND an old archived chat -> should be retained.
+				fileF := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-31*24*time.Hour))
+				anotherOldArchivedChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, true, now.Add(-31*24*time.Hour))
+				_, err = db.LinkChatFiles(ctx, database.LinkChatFilesParams{
+					ChatID:       anotherOldArchivedChat.ID,
+					MaxFileLinks: 100,
+					FileIds:      []uuid.UUID{fileF},
+				})
+				require.NoError(t, err)
+				_, err = rawDB.ExecContext(ctx, "UPDATE chats SET updated_at = $1 WHERE id = $2",
+					now.Add(-31*24*time.Hour), anotherOldArchivedChat.ID)
+				require.NoError(t, err)
+
+				activeChatForF := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, false, now)
+				_, err = db.LinkChatFiles(ctx, database.LinkChatFilesParams{
+					ChatID:       activeChatForF.ID,
+					MaxFileLinks: 100,
+					FileIds:      []uuid.UUID{fileF},
+				})
+				require.NoError(t, err)
+
+				done := awaitDoTick(ctx, t, clk)
+				closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk, prometheus.NewRegistry(), nil)
+				defer closer.Close()
+				testutil.TryReceive(ctx, t, done)
+
+				_, err = db.GetChatFileByID(ctx, fileD)
+				require.Error(t, err, "file D in old archived chat should be deleted")
+
+				_, err = db.GetChatFileByID(ctx, fileE)
+				require.NoError(t, err, "file E in recently archived chat should be retained")
+
+				_, err = db.GetChatFileByID(ctx, fileF)
+				require.NoError(t, err, "file F in active + old archived chat should be retained")
+			},
+		},
+		{
+			name: "UnarchiveAfterFilePurge",
+			run: func(t *testing.T) {
+				// Validates that when dbpurge deletes chat_files rows,
+				// the FK cascade on chat_file_links automatically
+				// removes the stale links. Unarchiving a chat after
+				// file purge should show only surviving files.
+				ctx := testutil.Context(t, testutil.WaitLong)
+				db, _, rawDB := dbtestutil.NewDBWithSQLDB(t, dbtestutil.WithDumpOnFailure())
+				deps := setupChatDeps(ctx, t, db)
+
+				// Create a chat with three attached files.
+				fileA := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now)
+				fileB := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now)
+				fileC := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now)
+
+				chat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, false, now)
+				_, err := db.LinkChatFiles(ctx, database.LinkChatFilesParams{
+					ChatID:       chat.ID,
+					MaxFileLinks: 100,
+					FileIds:      []uuid.UUID{fileA, fileB, fileC},
+				})
+				require.NoError(t, err)
+
+				// Archive the chat.
+				_, err = db.ArchiveChatByID(ctx, chat.ID)
+				require.NoError(t, err)
+
+				// Simulate dbpurge deleting files A and B. The FK
+				// cascade on chat_file_links_file_id_fkey should
+				// automatically remove the corresponding link rows.
+				_, err = rawDB.ExecContext(ctx, "DELETE FROM chat_files WHERE id = ANY($1)", pq.Array([]uuid.UUID{fileA, fileB}))
+				require.NoError(t, err)
+
+				// Unarchive the chat.
+				_, err = db.UnarchiveChatByID(ctx, chat.ID)
+				require.NoError(t, err)
+
+				// Only file C should remain linked (FK cascade
+				// removed the links for deleted files A and B).
+				files, err := db.GetChatFileMetadataByChatID(ctx, chat.ID)
+				require.NoError(t, err)
+				require.Len(t, files, 1, "only surviving file should be linked")
+				require.Equal(t, fileC, files[0].ID)
+
+				// Edge case: delete the last file too. The chat
+				// should have zero linked files, not an error.
+				_, err = db.ArchiveChatByID(ctx, chat.ID)
+				require.NoError(t, err)
+				_, err = rawDB.ExecContext(ctx, "DELETE FROM chat_files WHERE id = $1", fileC)
+				require.NoError(t, err)
+				_, err = db.UnarchiveChatByID(ctx, chat.ID)
+				require.NoError(t, err)
+
+				files, err = db.GetChatFileMetadataByChatID(ctx, chat.ID)
+				require.NoError(t, err)
+				require.Empty(t, files, "all-files-deleted should yield empty result")
+
+				// Test parent+child cascade: deleting files should
+				// clean up links for both parent and child chats
+				// independently via FK cascade.
+				parentChat := createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, false, now)
+				childChat, err := db.InsertChat(ctx, database.InsertChatParams{
+					OwnerID:           deps.user.ID,
+					LastModelConfigID: deps.modelConfig.ID,
+					Title:             "child-chat",
+					Status:            database.ChatStatusWaiting,
+				})
+				require.NoError(t, err)
+				// Set root_chat_id to link child to parent.
+				_, err = rawDB.ExecContext(ctx, "UPDATE chats SET root_chat_id = $1 WHERE id = $2", parentChat.ID, childChat.ID)
+				require.NoError(t, err)
+
+				// Attach different files to parent and child.
+				parentFileKeep := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now)
+				parentFileStale := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now)
+				childFileKeep := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now)
+				childFileStale := createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now)
+
+				_, err = db.LinkChatFiles(ctx, database.LinkChatFilesParams{
+					ChatID:       parentChat.ID,
+					MaxFileLinks: 100,
+					FileIds:      []uuid.UUID{parentFileKeep, parentFileStale},
+				})
+				require.NoError(t, err)
+				_, err = db.LinkChatFiles(ctx, database.LinkChatFilesParams{
+					ChatID:       childChat.ID,
+					MaxFileLinks: 100,
+					FileIds:      []uuid.UUID{childFileKeep, childFileStale},
+				})
+				require.NoError(t, err)
+
+				// Archive via parent (cascades to child).
+				_, err = db.ArchiveChatByID(ctx, parentChat.ID)
+				require.NoError(t, err)
+
+				// Delete one file from each chat.
+				_, err = rawDB.ExecContext(ctx, "DELETE FROM chat_files WHERE id = ANY($1)",
+					pq.Array([]uuid.UUID{parentFileStale, childFileStale}))
+				require.NoError(t, err)
+
+				// Unarchive via parent.
+				_, err = db.UnarchiveChatByID(ctx, parentChat.ID)
+				require.NoError(t, err)
+
+				parentFiles, err := db.GetChatFileMetadataByChatID(ctx, parentChat.ID)
+				require.NoError(t, err)
+				require.Len(t, parentFiles, 1)
+				require.Equal(t, parentFileKeep, parentFiles[0].ID,
+					"parent should retain only non-stale file")
+
+				childFiles, err := db.GetChatFileMetadataByChatID(ctx, childChat.ID)
+				require.NoError(t, err)
+				require.Len(t, childFiles, 1)
+				require.Equal(t, childFileKeep, childFiles[0].ID,
+					"child should retain only non-stale file")
+			},
+		},
+		{
+			name: "BatchLimitFiles",
+			run: func(t *testing.T) {
+				ctx := testutil.Context(t, testutil.WaitLong)
+				db, _, rawDB := dbtestutil.NewDBWithSQLDB(t, dbtestutil.WithDumpOnFailure())
+				deps := setupChatDeps(ctx, t, db)
+
+				// Create 3 deletable orphaned files (all 31 days old).
+				for range 3 {
+					createChatFile(ctx, t, db, rawDB, deps.user.ID, deps.org.ID, now.Add(-31*24*time.Hour))
+				}
+
+				// Delete with limit 2 — should delete 2, leave 1.
+				deleted, err := db.DeleteOldChatFiles(ctx, database.DeleteOldChatFilesParams{
+					BeforeTime: now.Add(-30 * 24 * time.Hour),
+					LimitCount: 2,
+				})
+				require.NoError(t, err)
+				require.Equal(t, int64(2), deleted, "should delete exactly 2 files")
+
+				// Delete again — should delete the remaining 1.
+				deleted, err = db.DeleteOldChatFiles(ctx, database.DeleteOldChatFilesParams{
+					BeforeTime: now.Add(-30 * 24 * time.Hour),
+					LimitCount: 2,
+				})
+				require.NoError(t, err)
+				require.Equal(t, int64(1), deleted, "should delete remaining 1 file")
+			},
+		},
+		{
+			name: "BatchLimitChats",
+			run: func(t *testing.T) {
+				ctx := testutil.Context(t, testutil.WaitLong)
+				db, _, rawDB := dbtestutil.NewDBWithSQLDB(t, dbtestutil.WithDumpOnFailure())
+				deps := setupChatDeps(ctx, t, db)
+
+				// Create 3 deletable old archived chats.
+				for range 3 {
+					createChat(ctx, t, db, rawDB, deps.user.ID, deps.modelConfig.ID, true, now.Add(-31*24*time.Hour))
+				}
+
+				// Delete with limit 2 — should delete 2, leave 1.
+				deleted, err := db.DeleteOldChats(ctx, database.DeleteOldChatsParams{
+					BeforeTime: now.Add(-30 * 24 * time.Hour),
+					LimitCount: 2,
+				})
+				require.NoError(t, err)
+				require.Equal(t, int64(2), deleted, "should delete exactly 2 chats")
+
+				// Delete again — should delete the remaining 1.
+				deleted, err = db.DeleteOldChats(ctx, database.DeleteOldChatsParams{
+					BeforeTime: now.Add(-30 * 24 * time.Hour),
+					LimitCount: 2,
+				})
+				require.NoError(t, err)
+				require.Equal(t, int64(1), deleted, "should delete remaining 1 chat")
+			},
+		},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			tc.run(t)
+		})
+	}
+}

coderd/database/dump.sql

@@ -293,7 +293,8 @@ CREATE TYPE chat_status AS ENUM (
     'running',
     'paused',
     'completed',
-    'error'
+    'error',
+    'requires_action'
 );
 
 CREATE TYPE connection_status AS ENUM (
@@ -315,6 +316,11 @@ CREATE TYPE cors_behavior AS ENUM (
     'passthru'
 );
 
+CREATE TYPE credential_kind AS ENUM (
+    'centralized',
+    'byok'
+);
+
 CREATE TYPE crypto_key_feature AS ENUM (
     'workspace_apps_token',
     'workspace_apps_api_key',
@@ -1101,7 +1107,9 @@ CREATE TABLE aibridge_interceptions (
     thread_root_id uuid,
     client_session_id character varying(256),
     session_id text GENERATED ALWAYS AS (COALESCE(client_session_id, ((thread_root_id)::text)::character varying, ((id)::text)::character varying)) STORED NOT NULL,
-    provider_name text DEFAULT ''::text NOT NULL
+    provider_name text DEFAULT ''::text NOT NULL,
+    credential_kind credential_kind DEFAULT 'centralized'::credential_kind NOT NULL,
+    credential_hint character varying(15) DEFAULT ''::character varying NOT NULL
 );
 
 COMMENT ON TABLE aibridge_interceptions IS 'Audit log of requests intercepted by AI Bridge';
@@ -1118,6 +1126,10 @@ COMMENT ON COLUMN aibridge_interceptions.session_id IS 'Groups related intercept
 
 COMMENT ON COLUMN aibridge_interceptions.provider_name IS 'The provider instance name which may differ from provider when multiple instances of the same provider type exist.';
 
+COMMENT ON COLUMN aibridge_interceptions.credential_kind IS 'How the request was authenticated: centralized or byok.';
+
+COMMENT ON COLUMN aibridge_interceptions.credential_hint IS 'Masked credential identifier for audit (e.g. sk-a***efgh).';
+
 CREATE TABLE aibridge_model_thoughts (
     interception_id uuid NOT NULL,
     content text NOT NULL,
@@ -1269,6 +1281,11 @@ 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,
@@ -1276,7 +1293,8 @@ CREATE TABLE chat_files (
     created_at timestamp with time zone DEFAULT now() NOT NULL,
     name text DEFAULT ''::text NOT NULL,
     mimetype text NOT NULL,
-    data bytea NOT NULL
+    data bytea,
+    object_store_key text
 );
 
 CREATE TABLE chat_messages (
@@ -1413,7 +1431,8 @@ CREATE TABLE chats (
     agent_id uuid,
     pin_order integer DEFAULT 0 NOT NULL,
     last_read_message_id bigint,
-    last_injected_context jsonb
+    last_injected_context jsonb,
+    dynamic_tools jsonb
 );
 
 CREATE TABLE connection_logs (
@@ -3344,6 +3363,9 @@ 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 +3756,8 @@ 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);
@@ -3760,6 +3784,8 @@ CREATE INDEX idx_chat_providers_enabled ON chat_providers USING btree (enabled);
 
 CREATE INDEX idx_chat_queued_messages_chat_id ON chat_queued_messages USING btree (chat_id);
 
+CREATE INDEX idx_chats_agent_id ON chats USING btree (agent_id) WHERE (agent_id IS NOT NULL);
+
 CREATE INDEX idx_chats_labels ON chats USING gin (labels);
 
 CREATE INDEX idx_chats_last_model_config_id ON chats USING btree (last_model_config_id);
@@ -4036,6 +4062,12 @@ 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;
 

coderd/database/foreign_key_constraint.go

@@ -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;

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

@@ -0,0 +1,7 @@
+-- Backfill any NULL data values before restoring NOT NULL would require
+-- reading from the object store, which is not possible in a migration.
+-- Instead, delete rows that only exist in the object store.
+DELETE FROM chat_files WHERE data IS NULL;
+
+ALTER TABLE chat_files ALTER COLUMN data SET NOT NULL;
+ALTER TABLE chat_files DROP COLUMN object_store_key;

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

@@ -0,0 +1,8 @@
+-- Add object_store_key to track files stored in external object storage.
+-- When non-NULL, the file data lives in the object store under this key
+-- and the data column may be NULL.
+ALTER TABLE chat_files ADD COLUMN object_store_key TEXT;
+
+-- Make data nullable so new writes can skip the BYTEA column when
+-- storing in the object store.
+ALTER TABLE chat_files ALTER COLUMN data DROP NOT NULL;

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

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

coderd/database/modelmethods.go

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

coderd/database/modelqueries.go

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

coderd/database/modelqueries_internal_test.go

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

coderd/database/models.go

@@ -1290,12 +1290,13 @@ func AllChatModeValues() []ChatMode {
 type ChatStatus string
 
 const (
-	ChatStatusWaiting   ChatStatus = "waiting"
-	ChatStatusPending   ChatStatus = "pending"
-	ChatStatusRunning   ChatStatus = "running"
-	ChatStatusPaused    ChatStatus = "paused"
-	ChatStatusCompleted ChatStatus = "completed"
-	ChatStatusError     ChatStatus = "error"
+	ChatStatusWaiting        ChatStatus = "waiting"
+	ChatStatusPending        ChatStatus = "pending"
+	ChatStatusRunning        ChatStatus = "running"
+	ChatStatusPaused         ChatStatus = "paused"
+	ChatStatusCompleted      ChatStatus = "completed"
+	ChatStatusError          ChatStatus = "error"
+	ChatStatusRequiresAction ChatStatus = "requires_action"
 )
 
 func (e *ChatStatus) Scan(src interface{}) error {
@@ -1340,7 +1341,8 @@ func (e ChatStatus) Valid() bool {
 		ChatStatusRunning,
 		ChatStatusPaused,
 		ChatStatusCompleted,
-		ChatStatusError:
+		ChatStatusError,
+		ChatStatusRequiresAction:
 		return true
 	}
 	return false
@@ -1354,6 +1356,7 @@ func AllChatStatusValues() []ChatStatus {
 		ChatStatusPaused,
 		ChatStatusCompleted,
 		ChatStatusError,
+		ChatStatusRequiresAction,
 	}
 }
 
@@ -1543,6 +1546,64 @@ func AllCorsBehaviorValues() []CorsBehavior {
 	}
 }
 
+type CredentialKind string
+
+const (
+	CredentialKindCentralized CredentialKind = "centralized"
+	CredentialKindByok        CredentialKind = "byok"
+)
+
+func (e *CredentialKind) Scan(src interface{}) error {
+	switch s := src.(type) {
+	case []byte:
+		*e = CredentialKind(s)
+	case string:
+		*e = CredentialKind(s)
+	default:
+		return fmt.Errorf("unsupported scan type for CredentialKind: %T", src)
+	}
+	return nil
+}
+
+type NullCredentialKind struct {
+	CredentialKind CredentialKind `json:"credential_kind"`
+	Valid          bool           `json:"valid"` // Valid is true if CredentialKind is not NULL
+}
+
+// Scan implements the Scanner interface.
+func (ns *NullCredentialKind) Scan(value interface{}) error {
+	if value == nil {
+		ns.CredentialKind, ns.Valid = "", false
+		return nil
+	}
+	ns.Valid = true
+	return ns.CredentialKind.Scan(value)
+}
+
+// Value implements the driver Valuer interface.
+func (ns NullCredentialKind) Value() (driver.Value, error) {
+	if !ns.Valid {
+		return nil, nil
+	}
+	return string(ns.CredentialKind), nil
+}
+
+func (e CredentialKind) Valid() bool {
+	switch e {
+	case CredentialKindCentralized,
+		CredentialKindByok:
+		return true
+	}
+	return false
+}
+
+func AllCredentialKindValues() []CredentialKind {
+	return []CredentialKind{
+		CredentialKindCentralized,
+		CredentialKindByok,
+	}
+}
+
 type CryptoKeyFeature string
 
 const (
@@ -4040,6 +4101,10 @@ type AIBridgeInterception struct {
 	SessionID string `db:"session_id" json:"session_id"`
 	// The provider instance name which may differ from provider when multiple instances of the same provider type exist.
 	ProviderName string `db:"provider_name" json:"provider_name"`
+	// How the request was authenticated: centralized or byok.
+	CredentialKind CredentialKind `db:"credential_kind" json:"credential_kind"`
+	// Masked credential identifier for audit (e.g. sk-a***efgh).
+	CredentialHint string `db:"credential_hint" json:"credential_hint"`
 }
 
 // Audit log of model thinking in intercepted requests in AI Bridge
@@ -4180,6 +4245,7 @@ type Chat struct {
 	PinOrder            int32                 `db:"pin_order" json:"pin_order"`
 	LastReadMessageID   sql.NullInt64         `db:"last_read_message_id" json:"last_read_message_id"`
 	LastInjectedContext pqtype.NullRawMessage `db:"last_injected_context" json:"last_injected_context"`
+	DynamicTools        pqtype.NullRawMessage `db:"dynamic_tools" json:"dynamic_tools"`
 }
 
 type ChatDiffStatus struct {
@@ -4209,13 +4275,19 @@ type ChatDiffStatus struct {
 }
 
 type ChatFile 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"`
-	CreatedAt      time.Time `db:"created_at" json:"created_at"`
-	Name           string    `db:"name" json:"name"`
-	Mimetype       string    `db:"mimetype" json:"mimetype"`
-	Data           []byte    `db:"data" json:"data"`
+	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"`
+	CreatedAt      time.Time      `db:"created_at" json:"created_at"`
+	Name           string         `db:"name" json:"name"`
+	Mimetype       string         `db:"mimetype" json:"mimetype"`
+	Data           []byte         `db:"data" json:"data"`
+	ObjectStoreKey sql.NullString `db:"object_store_key" json:"object_store_key"`
+}
+
+type ChatFileLink struct {
+	ChatID uuid.UUID `db:"chat_id" json:"chat_id"`
+	FileID uuid.UUID `db:"file_id" json:"file_id"`
 }
 
 type ChatMessage struct {

coderd/database/querier.go

@@ -76,6 +76,7 @@ type sqlcQuerier interface {
 	CleanTailnetLostPeers(ctx context.Context) error
 	CleanTailnetTunnels(ctx context.Context) error
 	CleanupDeletedMCPServerIDsFromChats(ctx context.Context) error
+	ClearChatMessageProviderResponseIDsByChatID(ctx context.Context, chatID uuid.UUID) error
 	CountAIBridgeInterceptions(ctx context.Context, arg CountAIBridgeInterceptionsParams) (int64, error)
 	CountAIBridgeSessions(ctx context.Context, arg CountAIBridgeSessionsParams) (int64, error)
 	CountAuditLogs(ctx context.Context, arg CountAuditLogsParams) (int64, error)
@@ -128,6 +129,24 @@ type sqlcQuerier interface {
 	// connection events (connect, disconnect, open, close) which are handled
 	// separately by DeleteOldAuditLogConnectionEvents.
 	DeleteOldAuditLogs(ctx context.Context, arg DeleteOldAuditLogsParams) (int64, error)
+	// TODO(cian): Add indexes on chats(archived, updated_at) and
+	// chat_files(created_at) for purge query performance.
+	// See: https://github.com/coder/internal/issues/1438
+	// Deletes chat files that are older than the given threshold and are
+	// not referenced by any chat that is still active or was archived
+	// within the same threshold window. This covers two cases:
+	// 1. Orphaned files not linked to any chat.
+	// 2. Files whose every referencing chat has been archived for longer
+	//    than the retention period.
+	// Returns the deleted rows so callers can clean up associated object
+	// store entries.
+	DeleteOldChatFiles(ctx context.Context, arg DeleteOldChatFilesParams) ([]DeleteOldChatFilesRow, error)
+	// Deletes chats that have been archived for longer than the given
+	// threshold. Active (non-archived) chats are never deleted.
+	// Related chat_messages, chat_diff_statuses, and
+	// chat_queued_messages are removed via ON DELETE CASCADE.
+	// Parent/root references on child chats are SET NULL.
+	DeleteOldChats(ctx context.Context, arg DeleteOldChatsParams) (int64, error)
 	DeleteOldConnectionLogs(ctx context.Context, arg DeleteOldConnectionLogsParams) (int64, error)
 	// Delete all notification messages which have not been updated for over a week.
 	DeleteOldNotificationMessages(ctx context.Context) error
@@ -152,7 +171,7 @@ type sqlcQuerier interface {
 	DeleteTask(ctx context.Context, arg DeleteTaskParams) (uuid.UUID, error)
 	DeleteUserChatCompactionThreshold(ctx context.Context, arg DeleteUserChatCompactionThresholdParams) error
 	DeleteUserChatProviderKey(ctx context.Context, arg DeleteUserChatProviderKeyParams) error
-	DeleteUserSecret(ctx context.Context, id uuid.UUID) error
+	DeleteUserSecretByUserIDAndName(ctx context.Context, arg DeleteUserSecretByUserIDAndNameParams) (int64, error)
 	DeleteWebpushSubscriptionByUserIDAndEndpoint(ctx context.Context, arg DeleteWebpushSubscriptionByUserIDAndEndpointParams) error
 	DeleteWebpushSubscriptions(ctx context.Context, ids []uuid.UUID) error
 	DeleteWorkspaceACLByID(ctx context.Context, id uuid.UUID) error
@@ -199,6 +218,7 @@ type sqlcQuerier interface {
 	GetAPIKeysByUserID(ctx context.Context, arg GetAPIKeysByUserIDParams) ([]APIKey, error)
 	GetAPIKeysLastUsedAfter(ctx context.Context, lastUsed time.Time) ([]APIKey, error)
 	GetActiveAISeatCount(ctx context.Context) (int64, error)
+	GetActiveChatsByAgentID(ctx context.Context, agentID uuid.UUID) ([]Chat, error)
 	GetActivePresetPrebuildSchedules(ctx context.Context) ([]TemplateVersionPresetPrebuildSchedule, error)
 	GetActiveUserCount(ctx context.Context, includeSystem bool) (int64, error)
 	GetActiveWorkspaceBuildsByTemplateID(ctx context.Context, templateID uuid.UUID) ([]WorkspaceBuild, error)
@@ -244,6 +264,10 @@ 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.
@@ -251,16 +275,27 @@ type sqlcQuerier interface {
 	// otherwise the setting defaults to true.
 	GetChatIncludeDefaultSystemPrompt(ctx context.Context) (bool, error)
 	GetChatMessageByID(ctx context.Context, id int64) (ChatMessage, error)
+	// Aggregates message-level metrics per chat for messages created
+	// after the given timestamp. Uses message created_at so that
+	// ongoing activity in long-running chats is captured each window.
+	GetChatMessageSummariesPerChat(ctx context.Context, createdAfter time.Time) ([]GetChatMessageSummariesPerChatRow, error)
 	GetChatMessagesByChatID(ctx context.Context, arg GetChatMessagesByChatIDParams) ([]ChatMessage, error)
 	GetChatMessagesByChatIDAscPaginated(ctx context.Context, arg GetChatMessagesByChatIDAscPaginatedParams) ([]ChatMessage, error)
 	GetChatMessagesByChatIDDescPaginated(ctx context.Context, arg GetChatMessagesByChatIDDescPaginatedParams) ([]ChatMessage, error)
 	GetChatMessagesForPromptByChatID(ctx context.Context, chatID uuid.UUID) ([]ChatMessage, error)
 	GetChatModelConfigByID(ctx context.Context, id uuid.UUID) (ChatModelConfig, error)
 	GetChatModelConfigs(ctx context.Context) ([]ChatModelConfig, error)
+	// Returns all model configurations for telemetry snapshot collection.
+	GetChatModelConfigsForTelemetry(ctx context.Context) ([]GetChatModelConfigsForTelemetryRow, error)
 	GetChatProviderByID(ctx context.Context, id uuid.UUID) (ChatProvider, error)
 	GetChatProviderByProvider(ctx context.Context, provider string) (ChatProvider, error)
 	GetChatProviders(ctx context.Context) ([]ChatProvider, error)
 	GetChatQueuedMessages(ctx context.Context, chatID uuid.UUID) ([]ChatQueuedMessage, error)
+	// Returns the chat retention period in days. Chats archived longer
+	// than this and orphaned chat files older than this are purged by
+	// dbpurge. Returns 30 (days) when no value has been configured.
+	// A value of 0 disables chat purging entirely.
+	GetChatRetentionDays(ctx context.Context) (int32, error)
 	GetChatSystemPrompt(ctx context.Context) (string, error)
 	// GetChatSystemPromptConfig returns both chat system prompt settings in a
 	// single read to avoid torn reads between separate site-config lookups.
@@ -279,6 +314,10 @@ type sqlcQuerier interface {
 	GetChatWorkspaceTTL(ctx context.Context) (string, error)
 	GetChats(ctx context.Context, arg GetChatsParams) ([]GetChatsRow, error)
 	GetChatsByWorkspaceIDs(ctx context.Context, ids []uuid.UUID) ([]Chat, error)
+	// Retrieves chats updated after the given timestamp for telemetry
+	// snapshot collection. Uses updated_at so that long-running chats
+	// still appear in each snapshot window while they are active.
+	GetChatsUpdatedAfter(ctx context.Context, updatedAfter time.Time) ([]GetChatsUpdatedAfterRow, error)
 	GetConnectionLogsOffset(ctx context.Context, arg GetConnectionLogsOffsetParams) ([]GetConnectionLogsOffsetRow, error)
 	GetCryptoKeyByFeatureAndSequence(ctx context.Context, arg GetCryptoKeyByFeatureAndSequenceParams) (CryptoKey, error)
 	GetCryptoKeys(ctx context.Context) ([]CryptoKey, error)
@@ -474,8 +513,10 @@ type sqlcQuerier interface {
 	GetReplicasUpdatedAfter(ctx context.Context, updatedAt time.Time) ([]Replica, error)
 	GetRunningPrebuiltWorkspaces(ctx context.Context) ([]GetRunningPrebuiltWorkspacesRow, error)
 	GetRuntimeConfig(ctx context.Context, key string) (string, error)
-	// Find chats that appear stuck (running but heartbeat has expired).
-	// Used for recovery after coderd crashes or long hangs.
+	// Find chats that appear stuck and need recovery. This covers:
+	//   1. Running chats whose heartbeat has expired (worker crash).
+	//   2. Chats awaiting client action (requires_action) past the
+	//      timeout threshold (client disappeared).
 	GetStaleChats(ctx context.Context, staleThreshold time.Time) ([]Chat, error)
 	GetTailnetPeers(ctx context.Context, id uuid.UUID) ([]TailnetPeer, error)
 	GetTailnetTunnelPeerBindingsBatch(ctx context.Context, ids []uuid.UUID) ([]GetTailnetTunnelPeerBindingsBatchRow, error)
@@ -594,7 +635,6 @@ type sqlcQuerier interface {
 	GetUserLinkByUserIDLoginType(ctx context.Context, arg GetUserLinkByUserIDLoginTypeParams) (UserLink, error)
 	GetUserLinksByUserID(ctx context.Context, userID uuid.UUID) ([]UserLink, error)
 	GetUserNotificationPreferences(ctx context.Context, userID uuid.UUID) ([]NotificationPreference, error)
-	GetUserSecret(ctx context.Context, id uuid.UUID) (UserSecret, error)
 	GetUserSecretByUserIDAndName(ctx context.Context, arg GetUserSecretByUserIDAndNameParams) (UserSecret, error)
 	// GetUserStatusCounts returns the count of users in each status over time.
 	// The time range is inclusively defined by the start_time and end_time parameters.
@@ -778,6 +818,15 @@ type sqlcQuerier interface {
 	InsertWorkspaceProxy(ctx context.Context, arg InsertWorkspaceProxyParams) (WorkspaceProxy, error)
 	InsertWorkspaceResource(ctx context.Context, arg InsertWorkspaceResourceParams) (WorkspaceResource, error)
 	InsertWorkspaceResourceMetadata(ctx context.Context, arg InsertWorkspaceResourceMetadataParams) ([]WorkspaceResourceMetadatum, error)
+	// LinkChatFiles inserts file associations into the chat_file_links
+	// join table with deduplication (ON CONFLICT DO NOTHING). The INSERT
+	// is conditional: it only proceeds when the total number of links
+	// (existing + genuinely new) does not exceed max_file_links. Returns
+	// the number of genuinely new file IDs that were NOT inserted due to
+	// the cap. A return value of 0 means all files were linked (or were
+	// already linked). A positive value means the cap blocked that many
+	// new links.
+	LinkChatFiles(ctx context.Context, arg LinkChatFilesParams) (int32, error)
 	ListAIBridgeClients(ctx context.Context, arg ListAIBridgeClientsParams) ([]string, error)
 	ListAIBridgeInterceptions(ctx context.Context, arg ListAIBridgeInterceptionsParams) ([]ListAIBridgeInterceptionsRow, error)
 	// Finds all unique AI Bridge interception telemetry summaries combinations
@@ -805,7 +854,13 @@ type sqlcQuerier interface {
 	ListProvisionerKeysByOrganizationExcludeReserved(ctx context.Context, organizationID uuid.UUID) ([]ProvisionerKey, error)
 	ListTasks(ctx context.Context, arg ListTasksParams) ([]Task, error)
 	ListUserChatCompactionThresholds(ctx context.Context, userID uuid.UUID) ([]UserConfig, error)
-	ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]UserSecret, error)
+	// Returns metadata only (no value or value_key_id) for the
+	// REST API list and get endpoints.
+	ListUserSecrets(ctx context.Context, userID uuid.UUID) ([]ListUserSecretsRow, error)
+	// Returns all columns including the secret value. Used by the
+	// provisioner (build-time injection) and the agent manifest
+	// (runtime injection).
+	ListUserSecretsWithValues(ctx context.Context, userID uuid.UUID) ([]UserSecret, error)
 	ListWorkspaceAgentPortShares(ctx context.Context, workspaceID uuid.UUID) ([]WorkspaceAgentPortShare, error)
 	MarkAllInboxNotificationsAsRead(ctx context.Context, arg MarkAllInboxNotificationsAsReadParams) error
 	OIDCClaimFieldValues(ctx context.Context, arg OIDCClaimFieldValuesParams) ([]string, error)
@@ -842,11 +897,16 @@ type sqlcQuerier interface {
 	SelectUsageEventsForPublishing(ctx context.Context, now time.Time) ([]UsageEvent, error)
 	SoftDeleteChatMessageByID(ctx context.Context, id int64) error
 	SoftDeleteChatMessagesAfterID(ctx context.Context, arg SoftDeleteChatMessagesAfterIDParams) error
+	SoftDeleteContextFileMessages(ctx context.Context, chatID uuid.UUID) error
 	// Non blocking lock. Returns true if the lock was acquired, false otherwise.
 	//
 	// This must be called from within a transaction. The lock will be automatically
 	// released when the transaction ends.
 	TryAcquireLock(ctx context.Context, pgTryAdvisoryXactLock int64) (bool, error)
+	// Unarchives a chat (and its children). Stale file references are
+	// handled automatically by FK cascades on chat_file_links: when
+	// dbpurge deletes a chat_files row, the corresponding
+	// chat_file_links rows are cascade-deleted by PostgreSQL.
 	UnarchiveChatByID(ctx context.Context, id uuid.UUID) ([]Chat, error)
 	// This will always work regardless of the current state of the template version.
 	UnarchiveTemplateVersion(ctx context.Context, arg UnarchiveTemplateVersionParams) error
@@ -857,9 +917,11 @@ 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
@@ -942,7 +1004,7 @@ type sqlcQuerier interface {
 	UpdateUserProfile(ctx context.Context, arg UpdateUserProfileParams) (User, error)
 	UpdateUserQuietHoursSchedule(ctx context.Context, arg UpdateUserQuietHoursScheduleParams) (User, error)
 	UpdateUserRoles(ctx context.Context, arg UpdateUserRolesParams) (User, error)
-	UpdateUserSecret(ctx context.Context, arg UpdateUserSecretParams) (UserSecret, error)
+	UpdateUserSecretByUserIDAndName(ctx context.Context, arg UpdateUserSecretByUserIDAndNameParams) (UserSecret, error)
 	UpdateUserStatus(ctx context.Context, arg UpdateUserStatusParams) (User, error)
 	UpdateUserTaskNotificationAlertDismissed(ctx context.Context, arg UpdateUserTaskNotificationAlertDismissedParams) (bool, error)
 	UpdateUserTerminalFont(ctx context.Context, arg UpdateUserTerminalFontParams) (UserConfig, error)
@@ -986,6 +1048,7 @@ type sqlcQuerier interface {
 	UpsertChatDiffStatus(ctx context.Context, arg UpsertChatDiffStatusParams) (ChatDiffStatus, error)
 	UpsertChatDiffStatusReference(ctx context.Context, arg UpsertChatDiffStatusReferenceParams) (ChatDiffStatus, error)
 	UpsertChatIncludeDefaultSystemPrompt(ctx context.Context, includeDefaultSystemPrompt bool) error
+	UpsertChatRetentionDays(ctx context.Context, retentionDays int32) error
 	UpsertChatSystemPrompt(ctx context.Context, value string) error
 	UpsertChatTemplateAllowlist(ctx context.Context, templateAllowlist string) error
 	UpsertChatUsageLimitConfig(ctx context.Context, arg UpsertChatUsageLimitConfigParams) (ChatUsageLimitConfig, error)

coderd/database/querier_test.go

@@ -7339,13 +7339,7 @@ func TestUserSecretsCRUDOperations(t *testing.T) {
 		require.NoError(t, err)
 		assert.Equal(t, secretID, createdSecret.ID)
 
-		// 2. READ by ID
-		readSecret, err := db.GetUserSecret(ctx, createdSecret.ID)
-		require.NoError(t, err)
-		assert.Equal(t, createdSecret.ID, readSecret.ID)
-		assert.Equal(t, "workflow-secret", readSecret.Name)
-
-		// 3. READ by UserID and Name
+		// 2. READ by UserID and Name
 		readByNameParams := database.GetUserSecretByUserIDAndNameParams{
 			UserID: testUser.ID,
 			Name:   "workflow-secret",
@@ -7353,33 +7347,43 @@ func TestUserSecretsCRUDOperations(t *testing.T) {
 		readByNameSecret, err := db.GetUserSecretByUserIDAndName(ctx, readByNameParams)
 		require.NoError(t, err)
 		assert.Equal(t, createdSecret.ID, readByNameSecret.ID)
+		assert.Equal(t, "workflow-secret", readByNameSecret.Name)
 
-		// 4. LIST
+		// 3. LIST (metadata only)
 		secrets, err := db.ListUserSecrets(ctx, testUser.ID)
 		require.NoError(t, err)
 		require.Len(t, secrets, 1)
 		assert.Equal(t, createdSecret.ID, secrets[0].ID)
 
-		// 5. UPDATE
-		updateParams := database.UpdateUserSecretParams{
-			ID:          createdSecret.ID,
-			Description: "Updated workflow description",
-			Value:       "updated-workflow-value",
-			EnvName:     "UPDATED_WORKFLOW_ENV",
-			FilePath:    "/updated/workflow/path",
+		// 4. LIST with values
+		secretsWithValues, err := db.ListUserSecretsWithValues(ctx, testUser.ID)
+		require.NoError(t, err)
+		require.Len(t, secretsWithValues, 1)
+		assert.Equal(t, "workflow-value", secretsWithValues[0].Value)
+
+		// 5. UPDATE (partial - only description)
+		updateParams := database.UpdateUserSecretByUserIDAndNameParams{
+			UserID:            testUser.ID,
+			Name:              "workflow-secret",
+			UpdateDescription: true,
+			Description:       "Updated workflow description",
 		}
 
-		updatedSecret, err := db.UpdateUserSecret(ctx, updateParams)
+		updatedSecret, err := db.UpdateUserSecretByUserIDAndName(ctx, updateParams)
 		require.NoError(t, err)
 		assert.Equal(t, "Updated workflow description", updatedSecret.Description)
-		assert.Equal(t, "updated-workflow-value", updatedSecret.Value)
+		assert.Equal(t, "workflow-value", updatedSecret.Value) // Value unchanged
+		assert.Equal(t, "WORKFLOW_ENV", updatedSecret.EnvName) // EnvName unchanged
 
 		// 6. DELETE
-		err = db.DeleteUserSecret(ctx, createdSecret.ID)
+		_, err = db.DeleteUserSecretByUserIDAndName(ctx, database.DeleteUserSecretByUserIDAndNameParams{
+			UserID: testUser.ID,
+			Name:   "workflow-secret",
+		})
 		require.NoError(t, err)
 
 		// Verify deletion
-		_, err = db.GetUserSecret(ctx, createdSecret.ID)
+		_, err = db.GetUserSecretByUserIDAndName(ctx, readByNameParams)
 		require.Error(t, err)
 		assert.Contains(t, err.Error(), "no rows in result set")
 
@@ -7449,9 +7453,13 @@ func TestUserSecretsCRUDOperations(t *testing.T) {
 		})
 
 		// Verify both secrets exist
-		_, err = db.GetUserSecret(ctx, secret1.ID)
+		_, err = db.GetUserSecretByUserIDAndName(ctx, database.GetUserSecretByUserIDAndNameParams{
+			UserID: testUser.ID, Name: secret1.Name,
+		})
 		require.NoError(t, err)
-		_, err = db.GetUserSecret(ctx, secret2.ID)
+		_, err = db.GetUserSecretByUserIDAndName(ctx, database.GetUserSecretByUserIDAndNameParams{
+			UserID: testUser.ID, Name: secret2.Name,
+		})
 		require.NoError(t, err)
 	})
 }
@@ -7474,14 +7482,14 @@ func TestUserSecretsAuthorization(t *testing.T) {
 	org := dbgen.Organization(t, db, database.Organization{})
 
 	// Create secrets for users
-	user1Secret := dbgen.UserSecret(t, db, database.UserSecret{
+	_ = dbgen.UserSecret(t, db, database.UserSecret{
 		UserID:      user1.ID,
 		Name:        "user1-secret",
 		Description: "User 1's secret",
 		Value:       "user1-value",
 	})
 
-	user2Secret := dbgen.UserSecret(t, db, database.UserSecret{
+	_ = dbgen.UserSecret(t, db, database.UserSecret{
 		UserID:      user2.ID,
 		Name:        "user2-secret",
 		Description: "User 2's secret",
@@ -7491,7 +7499,8 @@ func TestUserSecretsAuthorization(t *testing.T) {
 	testCases := []struct {
 		name           string
 		subject        rbac.Subject
-		secretID       uuid.UUID
+		lookupUserID   uuid.UUID
+		lookupName     string
 		expectedAccess bool
 	}{
 		{
@@ -7501,7 +7510,8 @@ func TestUserSecretsAuthorization(t *testing.T) {
 				Roles: rbac.RoleIdentifiers{rbac.RoleMember()},
 				Scope: rbac.ScopeAll,
 			},
-			secretID:       user1Secret.ID,
+			lookupUserID:   user1.ID,
+			lookupName:     "user1-secret",
 			expectedAccess: true,
 		},
 		{
@@ -7511,7 +7521,8 @@ func TestUserSecretsAuthorization(t *testing.T) {
 				Roles: rbac.RoleIdentifiers{rbac.RoleMember()},
 				Scope: rbac.ScopeAll,
 			},
-			secretID:       user2Secret.ID,
+			lookupUserID:   user2.ID,
+			lookupName:     "user2-secret",
 			expectedAccess: false,
 		},
 		{
@@ -7521,7 +7532,8 @@ func TestUserSecretsAuthorization(t *testing.T) {
 				Roles: rbac.RoleIdentifiers{rbac.RoleOwner()},
 				Scope: rbac.ScopeAll,
 			},
-			secretID:       user1Secret.ID,
+			lookupUserID:   user1.ID,
+			lookupName:     "user1-secret",
 			expectedAccess: false,
 		},
 		{
@@ -7531,7 +7543,8 @@ func TestUserSecretsAuthorization(t *testing.T) {
 				Roles: rbac.RoleIdentifiers{rbac.ScopedRoleOrgAdmin(org.ID)},
 				Scope: rbac.ScopeAll,
 			},
-			secretID:       user1Secret.ID,
+			lookupUserID:   user1.ID,
+			lookupName:     "user1-secret",
 			expectedAccess: false,
 		},
 	}
@@ -7543,8 +7556,10 @@ func TestUserSecretsAuthorization(t *testing.T) {
 
 			authCtx := dbauthz.As(ctx, tc.subject)
 
-			// Test GetUserSecret
-			_, err := authDB.GetUserSecret(authCtx, tc.secretID)
+			_, err := authDB.GetUserSecretByUserIDAndName(authCtx, database.GetUserSecretByUserIDAndNameParams{
+				UserID: tc.lookupUserID,
+				Name:   tc.lookupName,
+			})
 
 			if tc.expectedAccess {
 				require.NoError(t, err, "expected access to be granted")
@@ -9070,10 +9085,11 @@ func TestUpdateAIBridgeInterceptionEnded(t *testing.T) {
 
 		for _, uid := range []uuid.UUID{{1}, {2}, {3}} {
 			insertParams := database.InsertAIBridgeInterceptionParams{
-				ID:          uid,
-				InitiatorID: user.ID,
-				Metadata:    json.RawMessage("{}"),
-				Client:      sql.NullString{String: "client", Valid: true},
+				ID:             uid,
+				InitiatorID:    user.ID,
+				Metadata:       json.RawMessage("{}"),
+				Client:         sql.NullString{String: "client", Valid: true},
+				CredentialKind: database.CredentialKindCentralized,
 			}
 
 			intc, err := db.InsertAIBridgeInterception(ctx, insertParams)

coderd/database/queries/aibridge.sql

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

coderd/database/queries/auditlogs.sql

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

coderd/database/queries/chatfiles.sql

@@ -1,6 +1,6 @@
 -- name: InsertChatFile :one
-INSERT INTO chat_files (owner_id, organization_id, name, mimetype, data)
-VALUES (@owner_id::uuid, @organization_id::uuid, @name::text, @mimetype::text, @data::bytea)
+INSERT INTO chat_files (owner_id, organization_id, name, mimetype, data, object_store_key)
+VALUES (@owner_id::uuid, @organization_id::uuid, @name::text, @mimetype::text, @data::bytea, @object_store_key::text)
 RETURNING id, owner_id, organization_id, created_at, name, mimetype;
 
 -- name: GetChatFileByID :one
@@ -8,3 +8,50 @@ SELECT * FROM chat_files WHERE id = @id::uuid;
 
 -- name: GetChatFilesByIDs :many
 SELECT * FROM chat_files WHERE id = ANY(@ids::uuid[]);
+
+-- name: GetChatFileMetadataByChatID :many
+-- GetChatFileMetadataByChatID returns lightweight file metadata for
+-- all files linked to a chat. The data column is excluded to avoid
+-- loading file content.
+SELECT cf.id, cf.owner_id, cf.organization_id, cf.name, cf.mimetype, cf.created_at
+FROM chat_files cf
+JOIN chat_file_links cfl ON cfl.file_id = cf.id
+WHERE cfl.chat_id = @chat_id::uuid
+ORDER BY cf.created_at ASC;
+
+-- TODO(cian): Add indexes on chats(archived, updated_at) and
+-- chat_files(created_at) for purge query performance.
+-- See: https://github.com/coder/internal/issues/1438
+-- name: DeleteOldChatFiles :many
+-- Deletes chat files that are older than the given threshold and are
+-- not referenced by any chat that is still active or was archived
+-- within the same threshold window. This covers two cases:
+-- 1. Orphaned files not linked to any chat.
+-- 2. Files whose every referencing chat has been archived for longer
+--    than the retention period.
+-- Returns the deleted rows so callers can clean up associated object
+-- store entries.
+WITH kept_file_ids AS (
+    -- NOTE: This uses updated_at as a proxy for archive time
+    -- because there is no archived_at column. Correctness
+    -- requires that updated_at is never backdated on archived
+    -- chats. See ArchiveChatByID.
+    SELECT DISTINCT cfl.file_id
+    FROM chat_file_links cfl
+    JOIN chats c ON c.id = cfl.chat_id
+    WHERE c.archived = false
+       OR c.updated_at >= @before_time::timestamptz
+),
+deletable AS (
+    SELECT cf.id
+    FROM chat_files cf
+    LEFT JOIN kept_file_ids k ON cf.id = k.file_id
+    WHERE cf.created_at < @before_time::timestamptz
+      AND k.file_id IS NULL
+    ORDER BY cf.created_at ASC
+    LIMIT @limit_count
+)
+DELETE FROM chat_files
+USING deletable
+WHERE chat_files.id = deletable.id
+RETURNING chat_files.id, chat_files.object_store_key;

coderd/database/queries/chats.sql

@@ -10,9 +10,14 @@ FROM chats
 ORDER BY (id = @id::uuid) DESC, created_at ASC, id ASC;
 
 -- name: UnarchiveChatByID :many
+-- Unarchives a chat (and its children). Stale file references are
+-- handled automatically by FK cascades on chat_file_links: when
+-- dbpurge deletes a chat_files row, the corresponding
+-- chat_file_links rows are cascade-deleted by PostgreSQL.
 WITH chats AS (
-    UPDATE chats
-    SET archived = false, updated_at = NOW()
+    UPDATE chats SET
+        archived = false,
+        updated_at = NOW()
     WHERE id = @id::uuid OR root_chat_id = @id::uuid
     RETURNING *
 )
@@ -394,7 +399,8 @@ INSERT INTO chats (
     mode,
     status,
     mcp_server_ids,
-    labels
+    labels,
+    dynamic_tools
 ) VALUES (
     @owner_id::uuid,
     sqlc.narg('workspace_id')::uuid,
@@ -407,7 +413,8 @@ INSERT INTO chats (
     sqlc.narg('mode')::chat_mode,
     @status::chat_status,
     COALESCE(@mcp_server_ids::uuid[], '{}'::uuid[]),
-    COALESCE(sqlc.narg('labels')::jsonb, '{}'::jsonb)
+    COALESCE(sqlc.narg('labels')::jsonb, '{}'::jsonb),
+    sqlc.narg('dynamic_tools')::jsonb
 )
 RETURNING
     *;
@@ -567,6 +574,43 @@ 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.
@@ -627,27 +671,34 @@ RETURNING
     *;
 
 -- name: GetStaleChats :many
--- Find chats that appear stuck (running but heartbeat has expired).
--- Used for recovery after coderd crashes or long hangs.
+-- Find chats that appear stuck and need recovery. This covers:
+--   1. Running chats whose heartbeat has expired (worker crash).
+--   2. Chats awaiting client action (requires_action) past the
+--      timeout threshold (client disappeared).
 SELECT
     *
 FROM
     chats
 WHERE
-    status = 'running'::chat_status
-    AND heartbeat_at < @stale_threshold::timestamptz;
+    (status = 'running'::chat_status
+        AND heartbeat_at < @stale_threshold::timestamptz)
+    OR (status = 'requires_action'::chat_status
+        AND updated_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 +934,8 @@ 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 +965,8 @@ 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 +1001,8 @@ 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 +1019,8 @@ 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 +1046,8 @@ 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 +1081,7 @@ 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
@@ -1174,3 +1231,88 @@ LIMIT 1;
 UPDATE chats
 SET last_read_message_id = @last_read_message_id::bigint
 WHERE id = @id::uuid;
+
+-- name: DeleteOldChats :execrows
+-- Deletes chats that have been archived for longer than the given
+-- threshold. Active (non-archived) chats are never deleted.
+-- Related chat_messages, chat_diff_statuses, and
+-- chat_queued_messages are removed via ON DELETE CASCADE.
+-- Parent/root references on child chats are SET NULL.
+WITH deletable AS (
+    SELECT id
+    FROM chats
+    WHERE archived = true
+      AND updated_at < @before_time::timestamptz
+    ORDER BY updated_at ASC
+    LIMIT @limit_count
+)
+DELETE FROM chats
+USING deletable
+WHERE chats.id = deletable.id
+  AND chats.archived = true;
+
+-- name: GetChatsUpdatedAfter :many
+-- Retrieves chats updated after the given timestamp for telemetry
+-- snapshot collection. Uses updated_at so that long-running chats
+-- still appear in each snapshot window while they are active.
+SELECT
+    id, owner_id, created_at, updated_at, status,
+    (parent_chat_id IS NOT NULL)::bool AS has_parent,
+    root_chat_id, workspace_id,
+    mode, archived, last_model_config_id
+FROM chats
+WHERE updated_at > @updated_after;
+
+-- name: GetChatMessageSummariesPerChat :many
+-- Aggregates message-level metrics per chat for messages created
+-- after the given timestamp. Uses message created_at so that
+-- ongoing activity in long-running chats is captured each window.
+SELECT
+    cm.chat_id,
+    COUNT(*)::bigint AS message_count,
+    COUNT(*) FILTER (WHERE cm.role = 'user')::bigint AS user_message_count,
+    COUNT(*) FILTER (WHERE cm.role = 'assistant')::bigint AS assistant_message_count,
+    COUNT(*) FILTER (WHERE cm.role = 'tool')::bigint AS tool_message_count,
+    COUNT(*) FILTER (WHERE cm.role = 'system')::bigint AS system_message_count,
+    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.reasoning_tokens), 0)::bigint AS total_reasoning_tokens,
+    COALESCE(SUM(cm.cache_creation_tokens), 0)::bigint AS total_cache_creation_tokens,
+    COALESCE(SUM(cm.cache_read_tokens), 0)::bigint AS total_cache_read_tokens,
+    COALESCE(SUM(cm.total_cost_micros), 0)::bigint AS total_cost_micros,
+    COALESCE(SUM(cm.runtime_ms), 0)::bigint AS total_runtime_ms,
+    COUNT(DISTINCT cm.model_config_id)::bigint AS distinct_model_count,
+    COUNT(*) FILTER (WHERE cm.compressed)::bigint AS compressed_message_count
+FROM chat_messages cm
+WHERE cm.created_at > @created_after
+  AND cm.deleted = false
+GROUP BY cm.chat_id;
+
+-- name: GetChatModelConfigsForTelemetry :many
+-- Returns all model configurations for telemetry snapshot collection.
+SELECT id, provider, model, context_limit, enabled, is_default
+FROM chat_model_configs
+WHERE deleted = false;
+-- name: GetActiveChatsByAgentID :many
+SELECT *
+FROM chats
+WHERE agent_id = @agent_id::uuid
+    AND archived = false
+    -- Active statuses only: waiting, pending, running, paused,
+    -- requires_action.
+    -- Excludes completed and error (terminal states).
+    AND status IN ('waiting', 'running', 'paused', 'pending', 'requires_action')
+ORDER BY updated_at DESC;
+
+-- name: ClearChatMessageProviderResponseIDsByChatID :exec
+UPDATE chat_messages
+SET provider_response_id = NULL
+WHERE chat_id = @chat_id::uuid
+    AND deleted = false
+    AND provider_response_id IS NOT NULL;
+
+-- name: SoftDeleteContextFileMessages :exec
+UPDATE chat_messages SET deleted = true
+WHERE chat_id = @chat_id::uuid
+    AND deleted = false
+    AND content::jsonb @> '[{"type": "context-file"}]';

coderd/database/queries/connectionlogs.sql

@@ -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 (

coderd/database/queries/siteconfig.sql

@@ -236,3 +236,20 @@ VALUES ('agents_workspace_ttl', @workspace_ttl::text)
 ON CONFLICT (key) DO UPDATE
 SET value = @workspace_ttl::text
 WHERE site_configs.key = 'agents_workspace_ttl';
+
+-- name: GetChatRetentionDays :one
+-- Returns the chat retention period in days. Chats archived longer
+-- than this and orphaned chat files older than this are purged by
+-- dbpurge. Returns 30 (days) when no value has been configured.
+-- A value of 0 disables chat purging entirely.
+SELECT COALESCE(
+    (SELECT value::integer FROM site_configs
+     WHERE key = 'agents_chat_retention_days'),
+    30
+) :: integer AS retention_days;
+
+-- name: UpsertChatRetentionDays :exec
+INSERT INTO site_configs (key, value)
+VALUES ('agents_chat_retention_days', CAST(@retention_days AS integer)::text)
+ON CONFLICT (key) DO UPDATE SET value = CAST(@retention_days AS integer)::text
+WHERE site_configs.key = 'agents_chat_retention_days';

coderd/database/queries/user_secrets.sql

@@ -1,14 +1,26 @@
 -- name: GetUserSecretByUserIDAndName :one
-SELECT * FROM user_secrets
-WHERE user_id = $1 AND name = $2;
-
--- name: GetUserSecret :one
-SELECT * FROM user_secrets
-WHERE id = $1;
+SELECT *
+FROM user_secrets
+WHERE user_id = @user_id AND name = @name;
 
 -- name: ListUserSecrets :many
-SELECT * FROM user_secrets
-WHERE user_id = $1
+-- Returns metadata only (no value or value_key_id) for the
+-- REST API list and get endpoints.
+SELECT
+    id, user_id, name, description,
+    env_name, file_path,
+    created_at, updated_at
+FROM user_secrets
+WHERE user_id = @user_id
+ORDER BY name ASC;
+
+-- name: ListUserSecretsWithValues :many
+-- Returns all columns including the secret value. Used by the
+-- provisioner (build-time injection) and the agent manifest
+-- (runtime injection).
+SELECT *
+FROM user_secrets
+WHERE user_id = @user_id
 ORDER BY name ASC;
 
 -- name: CreateUserSecret :one
@@ -18,23 +30,32 @@ INSERT INTO user_secrets (
     name,
     description,
     value,
+    value_key_id,
     env_name,
     file_path
 ) VALUES (
-    $1, $2, $3, $4, $5, $6, $7
+    @id,
+    @user_id,
+    @name,
+    @description,
+    @value,
+    @value_key_id,
+    @env_name,
+    @file_path
 ) RETURNING *;
 
--- name: UpdateUserSecret :one
+-- name: UpdateUserSecretByUserIDAndName :one
 UPDATE user_secrets
 SET
-    description = $2,
-    value = $3,
-    env_name = $4,
-    file_path = $5,
-    updated_at = CURRENT_TIMESTAMP
-WHERE id = $1
+    value       = CASE WHEN @update_value::bool THEN @value ELSE value END,
+    value_key_id = CASE WHEN @update_value::bool THEN @value_key_id ELSE value_key_id END,
+    description = CASE WHEN @update_description::bool THEN @description ELSE description END,
+    env_name    = CASE WHEN @update_env_name::bool THEN @env_name ELSE env_name END,
+    file_path   = CASE WHEN @update_file_path::bool THEN @file_path ELSE file_path END,
+    updated_at  = CURRENT_TIMESTAMP
+WHERE user_id = @user_id AND name = @name
 RETURNING *;
 
--- name: DeleteUserSecret :exec
+-- name: DeleteUserSecretByUserIDAndName :execrows
 DELETE FROM user_secrets
-WHERE id = $1;
+WHERE user_id = @user_id AND name = @name;

coderd/database/sqlc.yaml

@@ -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

coderd/database/unique_constraint.go

@@ -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);

coderd/exp_chats.go

@@ -137,8 +137,9 @@ func publishChatConfigEvent(logger slog.Logger, ps dbpubsub.Pubsub, kind pubsub.
 func (api *API) watchChats(rw http.ResponseWriter, r *http.Request) {
 	ctx := r.Context()
 	apiKey := httpmw.APIKey(r)
+	logger := api.Logger.Named("chat_watcher")
 
-	sendEvent, senderClosed, err := httpapi.OneWayWebSocketEventSender(api.Logger)(rw, r)
+	conn, err := websocket.Accept(rw, r, nil)
 	if err != nil {
 		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
 			Message: "Failed to open chat watch stream.",
@@ -146,54 +147,44 @@ func (api *API) watchChats(rw http.ResponseWriter, r *http.Request) {
 		})
 		return
 	}
-	defer func() {
-		<-senderClosed
-	}()
 
-	cancelSubscribe, err := api.Pubsub.SubscribeWithErr(pubsub.ChatEventChannel(apiKey.UserID),
-		pubsub.HandleChatEvent(
-			func(ctx context.Context, payload pubsub.ChatEvent, err error) {
+	ctx, cancel := context.WithCancel(ctx)
+	defer cancel()
+
+	_ = conn.CloseRead(context.Background())
+
+	ctx, wsNetConn := codersdk.WebsocketNetConn(ctx, conn, websocket.MessageText)
+	defer wsNetConn.Close()
+
+	go httpapi.HeartbeatClose(ctx, logger, cancel, conn)
+
+	// The encoder is only written from the SubscribeWithErr callback,
+	// which delivers serially per subscription. Do not add a second
+	// write path without introducing synchronization.
+	encoder := json.NewEncoder(wsNetConn)
+
+	cancelSubscribe, err := api.Pubsub.SubscribeWithErr(pubsub.ChatWatchEventChannel(apiKey.UserID),
+		pubsub.HandleChatWatchEvent(
+			func(ctx context.Context, payload codersdk.ChatWatchEvent, err error) {
 				if err != nil {
-					api.Logger.Error(ctx, "chat event subscription error", slog.Error(err))
+					logger.Error(ctx, "chat watch event subscription error", slog.Error(err))
 					return
 				}
-				if err := sendEvent(codersdk.ServerSentEvent{
-					Type: codersdk.ServerSentEventTypeData,
-					Data: payload,
-				}); err != nil {
-					api.Logger.Debug(ctx, "failed to send chat event", slog.Error(err))
+				if err := encoder.Encode(payload); err != nil {
+					logger.Debug(ctx, "failed to send chat watch event", slog.Error(err))
+					cancel()
+					return
 				}
 			},
 		))
 	if err != nil {
-		if err := sendEvent(codersdk.ServerSentEvent{
-			Type: codersdk.ServerSentEventTypeError,
-			Data: codersdk.Response{
-				Message: "Internal error subscribing to chat events.",
-				Detail:  err.Error(),
-			},
-		}); err != nil {
-			api.Logger.Debug(ctx, "failed to send chat subscribe error event", slog.Error(err))
-		}
+		logger.Error(ctx, "failed to subscribe to chat watch events", slog.Error(err))
+		_ = conn.Close(websocket.StatusInternalError, "Failed to subscribe to chat events.")
 		return
 	}
 	defer cancelSubscribe()
 
-	// Send initial ping to signal the connection is ready.
-	if err := sendEvent(codersdk.ServerSentEvent{
-		Type: codersdk.ServerSentEventTypePing,
-	}); err != nil {
-		api.Logger.Debug(ctx, "failed to send chat ping event", slog.Error(err))
-	}
-
-	for {
-		select {
-		case <-ctx.Done():
-			return
-		case <-senderClosed:
-			return
-		}
-	}
+	<-ctx.Done()
 }
 
 // EXPERIMENTAL: chatsByWorkspace returns a mapping of workspace ID to
@@ -398,12 +389,26 @@ func (api *API) postChats(rw http.ResponseWriter, r *http.Request) {
 		return
 	}
 
+	// Cap the raw request body to prevent excessive memory use
+	// from large dynamic tool schemas.
+	r.Body = http.MaxBytesReader(rw, r.Body, int64(2*maxSystemPromptLenBytes))
+
 	var req codersdk.CreateChatRequest
 	if !httpapi.Read(ctx, rw, r, &req) {
 		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
@@ -478,15 +483,60 @@ func (api *API) postChats(rw http.ResponseWriter, r *http.Request) {
 		return
 	}
 
+	if len(req.UnsafeDynamicTools) > 250 {
+		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
+			Message: "Too many dynamic tools.",
+			Detail:  "Maximum 250 dynamic tools per chat.",
+		})
+		return
+	}
+
+	// Validate that dynamic tool names are non-empty and unique
+	// within the list. Name collision with built-in tools is
+	// checked at chatloop time when the full tool set is known.
+	if len(req.UnsafeDynamicTools) > 0 {
+		seenNames := make(map[string]struct{}, len(req.UnsafeDynamicTools))
+		for _, dt := range req.UnsafeDynamicTools {
+			if dt.Name == "" {
+				httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
+					Message: "Dynamic tool name must not be empty.",
+				})
+				return
+			}
+			if _, exists := seenNames[dt.Name]; exists {
+				httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
+					Message: "Duplicate dynamic tool name.",
+					Detail:  fmt.Sprintf("Tool %q appears more than once.", dt.Name),
+				})
+				return
+			}
+			seenNames[dt.Name] = struct{}{}
+		}
+	}
+
+	var dynamicToolsJSON json.RawMessage
+	if len(req.UnsafeDynamicTools) > 0 {
+		var err error
+		dynamicToolsJSON, err = json.Marshal(req.UnsafeDynamicTools)
+		if err != nil {
+			httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
+				Message: "Failed to marshal dynamic tools.",
+				Detail:  err.Error(),
+			})
+			return
+		}
+	}
+
 	chat, err := api.chatDaemon.CreateChat(ctx, chatd.CreateOptions{
 		OwnerID:            apiKey.UserID,
 		WorkspaceID:        workspaceSelection.WorkspaceID,
 		Title:              title,
 		ModelConfigID:      modelConfigID,
-		SystemPrompt:       api.resolvedChatSystemPrompt(ctx),
+		SystemPrompt:       req.SystemPrompt,
 		InitialUserContent: contentBlocks,
 		MCPServerIDs:       mcpServerIDs,
 		Labels:             labels,
+		DynamicTools:       dynamicToolsJSON,
 	})
 	if err != nil {
 		if maybeWriteLimitErr(ctx, rw, err) {
@@ -514,7 +564,32 @@ 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 +792,7 @@ 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 +1366,11 @@ 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 +1860,7 @@ 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 +1899,20 @@ 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 +1920,7 @@ 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 +1942,9 @@ 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 +1954,13 @@ 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 +1994,7 @@ 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 +2033,20 @@ 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.
@@ -2051,6 +2167,7 @@ func (api *API) streamChat(rw http.ResponseWriter, r *http.Request) {
 	ctx := r.Context()
 	chat := httpmw.ChatParam(r)
 	chatID := chat.ID
+	logger := api.Logger.Named("chat_streamer").With(slog.F("chat_id", chatID))
 
 	if api.chatDaemon == nil {
 		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
@@ -2073,7 +2190,22 @@ func (api *API) streamChat(rw http.ResponseWriter, r *http.Request) {
 		}
 	}
 
-	sendEvent, senderClosed, err := httpapi.OneWayWebSocketEventSender(api.Logger)(rw, r)
+	// Subscribe before accepting the WebSocket so that failures
+	// can still be reported as normal HTTP errors.
+	snapshot, events, cancelSub, ok := api.chatDaemon.Subscribe(ctx, chatID, r.Header, afterMessageID)
+	// Subscribe only fails today when the receiver is nil, which
+	// the chatDaemon == nil guard above already catches. This is
+	// defensive against future Subscribe failure modes.
+	if !ok {
+		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
+			Message: "Chat streaming is not available.",
+			Detail:  "Chat stream state is not configured.",
+		})
+		return
+	}
+	defer cancelSub()
+
+	conn, err := websocket.Accept(rw, r, nil)
 	if err != nil {
 		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
 			Message: "Failed to open chat stream.",
@@ -2081,41 +2213,30 @@ func (api *API) streamChat(rw http.ResponseWriter, r *http.Request) {
 		})
 		return
 	}
-	snapshot, events, cancel, ok := api.chatDaemon.Subscribe(ctx, chatID, r.Header, afterMessageID)
-	if !ok {
-		if err := sendEvent(codersdk.ServerSentEvent{
-			Type: codersdk.ServerSentEventTypeError,
-			Data: codersdk.Response{
-				Message: "Chat streaming is not available.",
-				Detail:  "Chat stream state is not configured.",
-			},
-		}); err != nil {
-			api.Logger.Debug(ctx, "failed to send chat stream unavailable event", slog.Error(err))
-		}
-		// Ensure the WebSocket is closed so senderClosed
-		// completes and the handler can return.
-		<-senderClosed
-		return
-	}
-	defer func() {
-		<-senderClosed
-	}()
+
+	ctx, cancel := context.WithCancel(ctx)
 	defer cancel()
 
+	_ = conn.CloseRead(context.Background())
+
+	ctx, wsNetConn := codersdk.WebsocketNetConn(ctx, conn, websocket.MessageText)
+	defer wsNetConn.Close()
+
+	go httpapi.HeartbeatClose(ctx, logger, cancel, conn)
+
 	// Mark the chat as read when the stream connects and again
 	// when it disconnects so we avoid per-message API calls while
 	// messages are actively streaming.
 	api.markChatAsRead(ctx, chatID)
 	defer api.markChatAsRead(context.WithoutCancel(ctx), chatID)
 
+	encoder := json.NewEncoder(wsNetConn)
+
 	sendChatStreamBatch := func(batch []codersdk.ChatStreamEvent) error {
 		if len(batch) == 0 {
 			return nil
 		}
-		return sendEvent(codersdk.ServerSentEvent{
-			Type: codersdk.ServerSentEventTypeData,
-			Data: batch,
-		})
+		return encoder.Encode(batch)
 	}
 
 	drainChatStreamBatch := func(
@@ -2148,7 +2269,7 @@ func (api *API) streamChat(rw http.ResponseWriter, r *http.Request) {
 			end = len(snapshot)
 		}
 		if err := sendChatStreamBatch(snapshot[start:end]); err != nil {
-			api.Logger.Debug(ctx, "failed to send chat stream snapshot", slog.Error(err))
+			logger.Debug(ctx, "failed to send chat stream snapshot", slog.Error(err))
 			return
 		}
 	}
@@ -2157,8 +2278,6 @@ func (api *API) streamChat(rw http.ResponseWriter, r *http.Request) {
 		select {
 		case <-ctx.Done():
 			return
-		case <-senderClosed:
-			return
 		case firstEvent, ok := <-events:
 			if !ok {
 				return
@@ -2168,7 +2287,7 @@ func (api *API) streamChat(rw http.ResponseWriter, r *http.Request) {
 				chatStreamBatchSize,
 			)
 			if err := sendChatStreamBatch(batch); err != nil {
-				api.Logger.Debug(ctx, "failed to send chat stream event", slog.Error(err))
+				logger.Debug(ctx, "failed to send chat stream event", slog.Error(err))
 				return
 			}
 			if streamClosed {
@@ -2183,6 +2302,7 @@ func (api *API) interruptChat(rw http.ResponseWriter, r *http.Request) {
 	ctx := r.Context()
 	chat := httpmw.ChatParam(r)
 	chatID := chat.ID
+	logger := api.Logger.Named("chat_interrupt").With(slog.F("chat_id", chatID))
 
 	if api.chatDaemon != nil {
 		chat = api.chatDaemon.InterruptChat(ctx, chat)
@@ -2196,8 +2316,7 @@ func (api *API) interruptChat(rw http.ResponseWriter, r *http.Request) {
 			LastError:   sql.NullString{},
 		})
 		if updateErr != nil {
-			api.Logger.Error(ctx, "failed to mark chat as waiting",
-				slog.F("chat_id", chatID), slog.Error(updateErr))
+			logger.Error(ctx, "failed to mark chat as waiting", slog.Error(updateErr))
 			httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
 				Message: "Failed to interrupt chat.",
 				Detail:  updateErr.Error(),
@@ -2207,7 +2326,7 @@ 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 +2370,7 @@ 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.
@@ -2869,6 +2988,8 @@ const (
 	maxChatFileSize = 10 << 20
 	// maxChatFileName is the maximum length of an uploaded file name.
 	maxChatFileName = 255
+	// chatFilesNamespace is the object store namespace for chat files.
+	chatFilesNamespace = "chatfiles"
 )
 
 // allowedChatFileMIMETypes lists the content types accepted for chat
@@ -3107,6 +3228,70 @@ func (api *API) putChatWorkspaceTTL(rw http.ResponseWriter, r *http.Request) {
 	rw.WriteHeader(http.StatusNoContent)
 }
 
+// @Summary Get chat retention days
+// @ID get-chat-retention-days
+// @Security CoderSessionToken
+// @Tags Chats
+// @Produce json
+// @Success 200 {object} codersdk.ChatRetentionDaysResponse
+// @Router /experimental/chats/config/retention-days [get]
+// @x-apidocgen {"skip": true}
+//
+//nolint:revive // get-return: revive assumes get* must be a getter, but this is an HTTP handler.
+func (api *API) getChatRetentionDays(rw http.ResponseWriter, r *http.Request) {
+	ctx := r.Context()
+	retentionDays, err := api.Database.GetChatRetentionDays(ctx)
+	if err != nil {
+		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
+			Message: "Failed to get chat retention days.",
+			Detail:  err.Error(),
+		})
+		return
+	}
+	httpapi.Write(ctx, rw, http.StatusOK, codersdk.ChatRetentionDaysResponse{
+		RetentionDays: retentionDays,
+	})
+}
+
+// Keep in sync with retentionDaysMaximum in
+// site/src/pages/AgentsPage/AgentSettingsBehaviorPageView.tsx.
+const retentionDaysMaximum = 3650 // ~10 years
+
+// @Summary Update chat retention days
+// @ID update-chat-retention-days
+// @Security CoderSessionToken
+// @Tags Chats
+// @Accept json
+// @Param request body codersdk.UpdateChatRetentionDaysRequest true "Request body"
+// @Success 204
+// @Router /experimental/chats/config/retention-days [put]
+// @x-apidocgen {"skip": true}
+func (api *API) putChatRetentionDays(rw http.ResponseWriter, r *http.Request) {
+	ctx := r.Context()
+	if !api.Authorize(r, policy.ActionUpdate, rbac.ResourceDeploymentConfig) {
+		httpapi.Forbidden(rw)
+		return
+	}
+	var req codersdk.UpdateChatRetentionDaysRequest
+	if !httpapi.Read(ctx, rw, r, &req) {
+		return
+	}
+	if req.RetentionDays < 0 || req.RetentionDays > retentionDaysMaximum {
+		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
+			Message: fmt.Sprintf("Retention days must be between 0 and %d.", retentionDaysMaximum),
+		})
+		return
+	}
+	if err := api.Database.UpsertChatRetentionDays(ctx, req.RetentionDays); err != nil {
+		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
+			Message: "Failed to update chat retention days.",
+			Detail:  err.Error(),
+		})
+		return
+	}
+	rw.WriteHeader(http.StatusNoContent)
+}
+
 // EXPERIMENTAL: this endpoint is experimental and is subject to change.
 //
 //nolint:revive // get-return: revive assumes get* must be a getter, but this is an HTTP handler.
@@ -3476,35 +3661,6 @@ 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)
@@ -3630,12 +3786,21 @@ func (api *API) postChatFile(rw http.ResponseWriter, r *http.Request) {
 		}
 	}
 
+	key := uuid.New().String()
+	if err := api.ObjectStore.Write(ctx, chatFilesNamespace, key, data); err != nil {
+		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
+			Message: "Failed to save chat file.",
+			Detail:  err.Error(),
+		})
+		return
+	}
+
 	chatFile, err := api.Database.InsertChatFile(ctx, database.InsertChatFileParams{
 		OwnerID:        apiKey.UserID,
 		OrganizationID: orgID,
 		Name:           filename,
 		Mimetype:       detected,
-		Data:           data,
+		ObjectStoreKey: key,
 	})
 	if err != nil {
 		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
@@ -3682,6 +3847,27 @@ func (api *API) chatFileByID(rw http.ResponseWriter, r *http.Request) {
 		rw.Header().Set("Content-Disposition", "inline")
 	}
 	rw.Header().Set("Cache-Control", "private, max-age=31536000, immutable")
+
+	// Serve from object store, falling back to the database BYTEA
+	// column for files that predate the migration.
+	if chatFile.ObjectStoreKey.Valid && chatFile.ObjectStoreKey.String != "" {
+		rc, info, err := api.ObjectStore.Read(ctx, chatFilesNamespace, chatFile.ObjectStoreKey.String)
+		if err != nil {
+			httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
+				Message: "Failed to read chat file from storage.",
+				Detail:  err.Error(),
+			})
+			return
+		}
+		defer rc.Close()
+		rw.Header().Set("Content-Length", strconv.FormatInt(info.Size, 10))
+		rw.WriteHeader(http.StatusOK)
+		if _, err := io.Copy(rw, rc); err != nil {
+			api.Logger.Debug(ctx, "failed to stream chat file response", slog.Error(err))
+		}
+		return
+	}
+
 	rw.Header().Set("Content-Length", strconv.Itoa(len(chatFile.Data)))
 	rw.WriteHeader(http.StatusOK)
 	if _, err := rw.Write(chatFile.Data); err != nil {
@@ -3692,6 +3878,7 @@ 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 +3889,15 @@ 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 +3905,7 @@ 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 +3914,7 @@ 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 +3925,23 @@ 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),
 				}
@@ -3768,7 +3959,7 @@ func createChatInputFromParts(
 			}
 			textParts = append(textParts, sb.String())
 		default:
-			return nil, "", &codersdk.Response{
+			return nil, "", nil, &codersdk.Response{
 				Message: "Invalid input part.",
 				Detail: fmt.Sprintf(
 					"%s[%d].type %q is not supported.",
@@ -3783,13 +3974,13 @@ 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 {
@@ -3824,6 +4015,70 @@ 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 == "" {
@@ -3840,6 +4095,7 @@ func convertChatCostModelBreakdown(model database.GetChatCostPerModelRow) coders
 		TotalOutputTokens:        model.TotalOutputTokens,
 		TotalCacheReadTokens:     model.TotalCacheReadTokens,
 		TotalCacheCreationTokens: model.TotalCacheCreationTokens,
+		TotalRuntimeMs:           model.TotalRuntimeMs,
 	}
 }
 
@@ -3853,6 +4109,7 @@ func convertChatCostChatBreakdown(chat database.GetChatCostPerChatRow) codersdk.
 		TotalOutputTokens:        chat.TotalOutputTokens,
 		TotalCacheReadTokens:     chat.TotalCacheReadTokens,
 		TotalCacheCreationTokens: chat.TotalCacheCreationTokens,
+		TotalRuntimeMs:           chat.TotalRuntimeMs,
 	}
 }
 
@@ -3869,6 +4126,7 @@ func convertChatCostUserRollup(user database.GetChatCostPerUserRow) codersdk.Cha
 		TotalOutputTokens:        user.TotalOutputTokens,
 		TotalCacheReadTokens:     user.TotalCacheReadTokens,
 		TotalCacheCreationTokens: user.TotalCacheCreationTokens,
+		TotalRuntimeMs:           user.TotalRuntimeMs,
 	}
 }
 
@@ -5568,3 +5826,77 @@ func (api *API) prInsights(rw http.ResponseWriter, r *http.Request) {
 		RecentPRs:  prEntries,
 	})
 }
+
+// EXPERIMENTAL: this endpoint is experimental and is subject to change.
+//
+//nolint:revive // HTTP handler writes to ResponseWriter.
+func (api *API) postChatToolResults(rw http.ResponseWriter, r *http.Request) {
+	ctx := r.Context()
+	chat := httpmw.ChatParam(r)
+	apiKey := httpmw.APIKey(r)
+
+	// Cap the raw request body to prevent excessive memory use.
+	r.Body = http.MaxBytesReader(rw, r.Body, int64(2*maxSystemPromptLenBytes))
+	var req codersdk.SubmitToolResultsRequest
+
+	if !httpapi.Read(ctx, rw, r, &req) {
+		return
+	}
+
+	if len(req.Results) == 0 {
+		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
+			Message: "At least one tool result is required.",
+		})
+		return
+	}
+
+	// Fast-path check outside the transaction. The authoritative
+	// check happens inside SubmitToolResults under a row lock.
+	if chat.Status != database.ChatStatusRequiresAction {
+		httpapi.Write(ctx, rw, http.StatusConflict, codersdk.Response{
+			Message: "Chat is not waiting for tool results.",
+			Detail:  fmt.Sprintf("Chat status is %q, expected %q.", chat.Status, database.ChatStatusRequiresAction),
+		})
+		return
+	}
+
+	var dynamicTools json.RawMessage
+	if chat.DynamicTools.Valid {
+		dynamicTools = chat.DynamicTools.RawMessage
+	}
+
+	err := api.chatDaemon.SubmitToolResults(ctx, chatd.SubmitToolResultsOptions{
+		ChatID:        chat.ID,
+		UserID:        apiKey.UserID,
+		ModelConfigID: chat.LastModelConfigID,
+		Results:       req.Results,
+		DynamicTools:  dynamicTools,
+	})
+	if err != nil {
+		var validationErr *chatd.ToolResultValidationError
+		var conflictErr *chatd.ToolResultStatusConflictError
+		switch {
+		case errors.As(err, &conflictErr):
+			httpapi.Write(ctx, rw, http.StatusConflict, codersdk.Response{
+				Message: "Chat is not waiting for tool results.",
+				Detail:  err.Error(),
+			})
+		case errors.As(err, &validationErr):
+			httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
+				Message: validationErr.Message,
+				Detail:  validationErr.Detail,
+			})
+		default:
+			api.Logger.Error(ctx, "tool results submission failed",
+				slog.F("chat_id", chat.ID),
+				slog.Error(err),
+			)
+			httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
+				Message: "Internal error submitting tool results.",
+			})
+		}
+		return
+	}
+
+	rw.WriteHeader(http.StatusNoContent)
+}

coderd/export_test.go

@@ -0,0 +1,4 @@
+package coderd
+
+// InsertAgentChatTestModelConfig exposes insertAgentChatTestModelConfig for external tests.
+var InsertAgentChatTestModelConfig = insertAgentChatTestModelConfig

coderd/members_test.go

@@ -148,7 +148,7 @@ func TestGetOrgMembersFilter(t *testing.T) {
 	setupCtx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
 	defer cancel()
 
-	coderdtest.UsersFilter(setupCtx, t, client, api.Database, nil, func(testCtx context.Context, req codersdk.UsersRequest) []codersdk.ReducedUser {
+	coderdtest.UsersFilter(setupCtx, t, client, api.Database, nil, nil, func(testCtx context.Context, req codersdk.UsersRequest) []codersdk.ReducedUser {
 		res, err := client.OrganizationMembersPaginated(testCtx, first.OrganizationID, req)
 		require.NoError(t, err)
 		reduced := make([]codersdk.ReducedUser, len(res.Members))