chore: update colors names to tailwind variants

Addresses [`aibridge#54`](https://github.com/coder/aibridge/issues/54)

When querying against the values in the database for
`/api/experimental/aibridge/interceptions` we found strange behaviour
wherein there was interceptions that lacked prompting and other various
fields we want. Generally this was as a result of the data not actually
existing for these values (as they were inflight).

The simple solution to this was to hide them if they didn't exist. This
PR addresses that.

---------

Co-authored-by: Danny Kopping <danny@coder.com>

.github/.linkspector.yml

@@ -27,5 +27,7 @@ ignorePatterns:
   - pattern: "splunk.com"
   - pattern: "stackoverflow.com/questions"
   - pattern: "developer.hashicorp.com/terraform/language"
+  - pattern: "platform.openai.com/docs/api-reference"
+  - pattern: "api.openai.com"
 aliveStatusCodes:
   - 200

.github/actions/setup-go/action.yaml

@@ -4,7 +4,7 @@ description: |
 inputs:
   version:
     description: "The Go version to use."
-    default: "1.24.6"
+    default: "1.24.10"
   use-preinstalled-go:
     description: "Whether to use preinstalled Go."
     default: "false"

.github/actions/setup-sqlc/action.yaml

@@ -5,6 +5,13 @@ runs:
   using: "composite"
   steps:
     - name: Setup sqlc
-      uses: sqlc-dev/setup-sqlc@c0209b9199cd1cce6a14fc27cabcec491b651761 # v4.0.0
-      with:
-        sqlc-version: "1.27.0"
+      # uses: sqlc-dev/setup-sqlc@c0209b9199cd1cce6a14fc27cabcec491b651761 # v4.0.0
+      # with:
+      #   sqlc-version: "1.30.0"
+
+      # Switched to coder/sqlc fork to fix ambiguous column bug, see:
+      # - https://github.com/coder/sqlc/pull/1
+      # - https://github.com/sqlc-dev/sqlc/pull/4159
+      shell: bash
+      run: |
+        CGO_ENABLED=1 go install github.com/coder/sqlc/cmd/sqlc@aab4e865a51df0c43e1839f81a9d349b41d14f05

.github/actions/setup-tf/action.yaml

@@ -7,5 +7,5 @@ runs:
     - name: Install Terraform
       uses: hashicorp/setup-terraform@b9cd54a3c349d3f38e8881555d616ced269862dd # v3.1.2
       with:
-        terraform_version: 1.13.0
+        terraform_version: 1.13.4
         terraform_wrapper: false

.github/fly-wsproxies/sao-paulo-coder.toml

@@ -1,34 +0,0 @@
-app = "sao-paulo-coder"
-primary_region = "gru"
-
-[experimental]
-  entrypoint = ["/bin/sh", "-c", "CODER_DERP_SERVER_RELAY_URL=\"http://[${FLY_PRIVATE_IP}]:3000\" /opt/coder wsproxy server"]
-  auto_rollback = true
-
-[build]
-  image = "ghcr.io/coder/coder-preview:main"
-
-[env]
-  CODER_ACCESS_URL = "https://sao-paulo.fly.dev.coder.com"
-  CODER_HTTP_ADDRESS = "0.0.0.0:3000"
-  CODER_PRIMARY_ACCESS_URL = "https://dev.coder.com"
-  CODER_WILDCARD_ACCESS_URL = "*--apps.sao-paulo.fly.dev.coder.com"
-  CODER_VERBOSE = "true"
-
-[http_service]
-  internal_port = 3000
-  force_https = true
-  auto_stop_machines = true
-  auto_start_machines = true
-  min_machines_running = 0
-
-# Ref: https://fly.io/docs/reference/configuration/#http_service-concurrency
-[http_service.concurrency]
-  type = "requests"
-  soft_limit = 50
-  hard_limit = 100
-
-[[vm]]
-  cpu_kind = "shared"
-  cpus = 2
-  memory_mb = 512

.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@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         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@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -191,7 +191,7 @@ jobs:
 
       # Check for any typos
       - name: Check for typos
-        uses: crate-ci/typos@80c8a4945eec0f6d464eaf9e65ed98ef085283d1 # v1.38.1
+        uses: crate-ci/typos@626c4bedb751ce0b7f03262ca97ddda9a076ae1c # v1.39.2
         with:
           config: .github/workflows/typos.toml
 
@@ -230,12 +230,12 @@ jobs:
         shell: bash
 
   gen:
-    timeout-minutes: 8
+    timeout-minutes: 20
     runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
     if: ${{ !cancelled() }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -271,6 +271,7 @@ jobs:
           popd
 
       - name: make gen
+        timeout-minutes: 8
         run: |
           # Remove golden files to detect discrepancy in generated files.
           make clean/golden-files
@@ -288,10 +289,10 @@ jobs:
     needs: changes
     if: needs.changes.outputs.offlinedocs-only == 'false' || needs.changes.outputs.ci == 'true' || github.ref == 'refs/heads/main'
     runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
-    timeout-minutes: 7
+    timeout-minutes: 20
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -315,6 +316,7 @@ jobs:
         run: go install mvdan.cc/sh/v3/cmd/shfmt@v3.7.0
 
       - name: make fmt
+        timeout-minutes: 7
         run: |
           PATH="${PATH}:$(go env GOPATH)/bin" \
             make --output-sync -j -B fmt
@@ -341,7 +343,7 @@ jobs:
           - windows-2022
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -376,13 +378,6 @@ jobs:
         id: go-paths
         uses: ./.github/actions/setup-go-paths
 
-      - name: Download Go Build Cache
-        id: download-go-build-cache
-        uses: ./.github/actions/test-cache/download
-        with:
-          key-prefix: test-go-build-${{ runner.os }}-${{ runner.arch }}
-          cache-path: ${{ steps.go-paths.outputs.cached-dirs }}
-
       - name: Setup Go
         uses: ./.github/actions/setup-go
         with:
@@ -390,8 +385,7 @@ jobs:
           # download the toolchain configured in go.mod, so we don't
           # need to reinstall it. It's faster on Windows runners.
           use-preinstalled-go: ${{ runner.os == 'Windows' }}
-          # Cache is already downloaded above
-          use-cache: false
+          use-cache: true
 
       - name: Setup Terraform
         uses: ./.github/actions/setup-tf
@@ -505,12 +499,6 @@ jobs:
           name: failed-test-db-dump-${{matrix.os}}
           path: "**/*.test.sql"
 
-      - name: Upload Go Build Cache
-        uses: ./.github/actions/test-cache/upload
-        with:
-          cache-key: ${{ steps.download-go-build-cache.outputs.cache-key }}
-          cache-path: ${{ steps.go-paths.outputs.cached-dirs }}
-
       - name: Upload Test Cache
         uses: ./.github/actions/test-cache/upload
         with:
@@ -544,7 +532,7 @@ jobs:
     timeout-minutes: 25
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -593,7 +581,7 @@ jobs:
     timeout-minutes: 25
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -653,7 +641,7 @@ jobs:
     timeout-minutes: 20
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -680,7 +668,7 @@ jobs:
     timeout-minutes: 20
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -713,7 +701,7 @@ jobs:
     name: ${{ matrix.variant.name }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -768,6 +756,14 @@ jobs:
           path: ./site/test-results/**/*.webm
           retention-days: 7
 
+      - name: Upload debug log
+        if: always() && github.actor != 'dependabot[bot]' && runner.os == 'Linux' && !github.event.pull_request.head.repo.fork
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
+        with:
+          name: coderd-debug-logs${{ matrix.variant.premium && '-premium' || ''  }}
+          path: ./site/e2e/test-results/debug.log
+          retention-days: 7
+
       - name: Upload pprof dumps
         if: always() && github.actor != 'dependabot[bot]' && runner.os == 'Linux' && !github.event.pull_request.head.repo.fork
         uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
@@ -785,7 +781,7 @@ jobs:
     if: needs.changes.outputs.site == 'true' || needs.changes.outputs.ci == 'true'
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -806,7 +802,7 @@ jobs:
       # the check to pass. This is desired in PRs, but not in mainline.
       - name: Publish to Chromatic (non-mainline)
         if: github.ref != 'refs/heads/main' && github.repository_owner == 'coder'
-        uses: chromaui/action@bc2d84ad2b60813a67d995c5582d696104a19383 # v13.3.2
+        uses: chromaui/action@ac86f2ff0a458ffbce7b40698abd44c0fa34d4b6 # v13.3.3
         env:
           NODE_OPTIONS: "--max_old_space_size=4096"
           STORYBOOK: true
@@ -838,7 +834,7 @@ jobs:
       # infinitely "in progress" in mainline unless we re-review each build.
       - name: Publish to Chromatic (mainline)
         if: github.ref == 'refs/heads/main' && github.repository_owner == 'coder'
-        uses: chromaui/action@bc2d84ad2b60813a67d995c5582d696104a19383 # v13.3.2
+        uses: chromaui/action@ac86f2ff0a458ffbce7b40698abd44c0fa34d4b6 # v13.3.3
         env:
           NODE_OPTIONS: "--max_old_space_size=4096"
           STORYBOOK: true
@@ -866,7 +862,7 @@ jobs:
 
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -937,7 +933,7 @@ jobs:
     if: always()
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -1057,7 +1053,7 @@ jobs:
     runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -1112,7 +1108,7 @@ jobs:
       IMAGE: ghcr.io/coder/coder-preview:${{ steps.build-docker.outputs.tag }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -1509,7 +1505,7 @@ 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@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 

.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@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         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@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -92,7 +92,7 @@ jobs:
         uses: google-github-actions/setup-gcloud@aa5489c8933f4cc7a4f7d45035b3b1440c9c10db # v3.0.1
 
       - name: Set up Flux CLI
-        uses: fluxcd/flux2/action@4a15fa6a023259353ef750acf1c98fe88407d4d0 # v2.7.2
+        uses: fluxcd/flux2/action@b6e76ca2534f76dcb8dd94fb057cdfa923c3b641 # v2.7.3
         with:
           # Keep this and the github action up to date with the version of flux installed in dogfood cluster
           version: "2.7.0"
@@ -146,7 +146,7 @@ jobs:
     needs: deploy
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -163,12 +163,10 @@ jobs:
         run: |
           flyctl deploy --image "$IMAGE" --app paris-coder --config ./.github/fly-wsproxies/paris-coder.toml --env "CODER_PROXY_SESSION_TOKEN=$TOKEN_PARIS" --yes
           flyctl deploy --image "$IMAGE" --app sydney-coder --config ./.github/fly-wsproxies/sydney-coder.toml --env "CODER_PROXY_SESSION_TOKEN=$TOKEN_SYDNEY" --yes
-          flyctl deploy --image "$IMAGE" --app sao-paulo-coder --config ./.github/fly-wsproxies/sao-paulo-coder.toml --env "CODER_PROXY_SESSION_TOKEN=$TOKEN_SAO_PAULO" --yes
           flyctl deploy --image "$IMAGE" --app jnb-coder --config ./.github/fly-wsproxies/jnb-coder.toml --env "CODER_PROXY_SESSION_TOKEN=$TOKEN_JNB" --yes
         env:
           FLY_API_TOKEN: ${{ secrets.FLY_API_TOKEN }}
           IMAGE: ${{ inputs.image }}
           TOKEN_PARIS: ${{ secrets.FLY_PARIS_CODER_PROXY_SESSION_TOKEN }}
           TOKEN_SYDNEY: ${{ secrets.FLY_SYDNEY_CODER_PROXY_SESSION_TOKEN }}
-          TOKEN_SAO_PAULO: ${{ secrets.FLY_SAO_PAULO_CODER_PROXY_SESSION_TOKEN }}
           TOKEN_JNB: ${{ secrets.FLY_JNB_CODER_PROXY_SESSION_TOKEN }}

.github/workflows/doc-check.yaml

@@ -0,0 +1,205 @@
+# This workflow checks if a PR requires documentation updates.
+# It creates a Coder Task that uses AI to analyze the PR changes,
+# search existing docs, and comment with recommendations.
+#
+# Triggered by: Adding the "doc-check" label to a PR, or manual dispatch.
+
+name: AI Documentation Check
+
+on:
+  pull_request:
+    types:
+      - labeled
+  workflow_dispatch:
+    inputs:
+      pr_url:
+        description: "Pull Request URL to check"
+        required: true
+        type: string
+      template_preset:
+        description: "Template preset to use"
+        required: false
+        default: ""
+        type: string
+
+jobs:
+  doc-check:
+    name: Analyze PR for Documentation Updates Needed
+    runs-on: ubuntu-latest
+    if: |
+      (github.event.label.name == 'doc-check' || github.event_name == 'workflow_dispatch') &&
+      (github.event.pull_request.draft == false || github.event_name == 'workflow_dispatch')
+    timeout-minutes: 30
+    env:
+      CODER_URL: ${{ secrets.DOC_CHECK_CODER_URL }}
+      CODER_SESSION_TOKEN: ${{ secrets.DOC_CHECK_CODER_SESSION_TOKEN }}
+    permissions:
+      contents: read
+      pull-requests: write
+      actions: write
+
+    steps:
+      - name: Determine PR Context
+        id: determine-context
+        env:
+          GITHUB_ACTOR: ${{ github.actor }}
+          GITHUB_EVENT_NAME: ${{ github.event_name }}
+          GITHUB_EVENT_PR_HTML_URL: ${{ github.event.pull_request.html_url }}
+          GITHUB_EVENT_PR_NUMBER: ${{ github.event.pull_request.number }}
+          GITHUB_EVENT_SENDER_ID: ${{ github.event.sender.id }}
+          GITHUB_EVENT_SENDER_LOGIN: ${{ github.event.sender.login }}
+          INPUTS_PR_URL: ${{ inputs.pr_url }}
+          INPUTS_TEMPLATE_PRESET: ${{ inputs.template_preset || '' }}
+          GH_TOKEN: ${{ github.token }}
+        run: |
+          echo "Using template preset: ${INPUTS_TEMPLATE_PRESET}"
+          echo "template_preset=${INPUTS_TEMPLATE_PRESET}" >> "${GITHUB_OUTPUT}"
+
+          # For workflow_dispatch, use the provided PR URL
+          if [[ "${GITHUB_EVENT_NAME}" == "workflow_dispatch" ]]; then
+            if ! GITHUB_USER_ID=$(gh api "users/${GITHUB_ACTOR}" --jq '.id'); then
+              echo "::error::Failed to get GitHub user ID for actor ${GITHUB_ACTOR}"
+              exit 1
+            fi
+            echo "Using workflow_dispatch actor: ${GITHUB_ACTOR} (ID: ${GITHUB_USER_ID})"
+            echo "github_user_id=${GITHUB_USER_ID}" >> "${GITHUB_OUTPUT}"
+            echo "github_username=${GITHUB_ACTOR}" >> "${GITHUB_OUTPUT}"
+
+            echo "Using PR URL: ${INPUTS_PR_URL}"
+            # Convert /pull/ to /issues/ for create-task-action compatibility
+            ISSUE_URL="${INPUTS_PR_URL/\/pull\//\/issues\/}"
+            echo "pr_url=${ISSUE_URL}" >> "${GITHUB_OUTPUT}"
+
+            # Extract PR number from URL for later use
+            PR_NUMBER=$(echo "${INPUTS_PR_URL}" | grep -oP '(?<=pull/)\d+')
+            echo "pr_number=${PR_NUMBER}" >> "${GITHUB_OUTPUT}"
+
+          elif [[ "${GITHUB_EVENT_NAME}" == "pull_request" ]]; then
+            GITHUB_USER_ID=${GITHUB_EVENT_SENDER_ID}
+            echo "Using label adder: ${GITHUB_EVENT_SENDER_LOGIN} (ID: ${GITHUB_USER_ID})"
+            echo "github_user_id=${GITHUB_USER_ID}" >> "${GITHUB_OUTPUT}"
+            echo "github_username=${GITHUB_EVENT_SENDER_LOGIN}" >> "${GITHUB_OUTPUT}"
+
+            echo "Using PR URL: ${GITHUB_EVENT_PR_HTML_URL}"
+            # Convert /pull/ to /issues/ for create-task-action compatibility
+            ISSUE_URL="${GITHUB_EVENT_PR_HTML_URL/\/pull\//\/issues\/}"
+            echo "pr_url=${ISSUE_URL}" >> "${GITHUB_OUTPUT}"
+            echo "pr_number=${GITHUB_EVENT_PR_NUMBER}" >> "${GITHUB_OUTPUT}"
+
+          else
+            echo "::error::Unsupported event type: ${GITHUB_EVENT_NAME}"
+            exit 1
+          fi
+
+      - name: Extract changed files and build prompt
+        id: extract-context
+        env:
+          PR_URL: ${{ steps.determine-context.outputs.pr_url }}
+          PR_NUMBER: ${{ steps.determine-context.outputs.pr_number }}
+          GH_TOKEN: ${{ github.token }}
+        run: |
+          echo "Analyzing PR #${PR_NUMBER}"
+
+          # Build task prompt - using unquoted heredoc so variables expand
+          TASK_PROMPT=$(cat <<EOF
+          Review PR #${PR_NUMBER} and determine if documentation needs updating or creating.
+
+          PR URL: ${PR_URL}
+
+          WORKFLOW:
+            1. Setup (repo is pre-cloned at ~/coder)
+               cd ~/coder
+               git fetch origin pull/${PR_NUMBER}/head:pr-${PR_NUMBER}
+               git checkout pr-${PR_NUMBER}
+
+            2. Get PR info
+               Use GitHub MCP tools to get PR title, body, and diff
+               Or use: git diff main...pr-${PR_NUMBER}
+
+            3. Understand Changes
+               Read the diff and identify what changed
+               Ask: Is this user-facing? Does it change behavior? Is it a new feature?
+
+            4. Search for Related Docs
+               cat ~/coder/docs/manifest.json | jq '.routes[] | {title, path}' | head -50
+               grep -ri "relevant_term" ~/coder/docs/ --include="*.md"
+
+            5. Decide
+               NEEDS DOCS if: New feature, API change, CLI change, behavior change, user-visible
+               NO DOCS if: Internal refactor, test-only, already documented, non-user-facing, dependency updates
+               FIRST check: Did this PR already update docs? If yes and complete, say "No Changes Needed"
+
+            6. Comment on the PR using this format
+
+          COMMENT FORMAT:
+          ## 📚 Documentation Check
+
+          ### ✅ Updates Needed
+          - **[docs/path/file.md](github_link)** - Brief what needs changing
+
+          ### 📝 New Docs Needed
+          - **docs/suggested/location.md** - What should be documented
+
+          ### ✨ No Changes Needed
+          [Reason: Documents already updated in PR | Internal changes only | Test-only | No user-facing impact]
+
+          ---
+          *This comment was generated by an AI Agent through [Coder Tasks](https://coder.com/docs/ai-coder/tasks)*
+
+          DOCS STRUCTURE:
+            Read ~/coder/docs/manifest.json for the complete documentation structure.
+            Common areas include: reference/, admin/, user-guides/, ai-coder/, install/, tutorials/
+            But check manifest.json - it has everything.
+
+          EOF
+          )
+
+          # Output the prompt
+          {
+            echo "task_prompt<<EOFOUTPUT"
+            echo "${TASK_PROMPT}"
+            echo "EOFOUTPUT"
+          } >> "${GITHUB_OUTPUT}"
+
+      - name: Checkout create-task-action
+        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        with:
+          fetch-depth: 1
+          path: ./.github/actions/create-task-action
+          persist-credentials: false
+          ref: main
+          repository: coder/create-task-action
+
+      - name: Create Coder Task for Documentation Check
+        id: create_task
+        uses: ./.github/actions/create-task-action
+        with:
+          coder-url: ${{ secrets.DOC_CHECK_CODER_URL }}
+          coder-token: ${{ secrets.DOC_CHECK_CODER_SESSION_TOKEN }}
+          coder-organization: "default"
+          coder-template-name: coder
+          coder-template-preset: ${{ steps.determine-context.outputs.template_preset }}
+          coder-task-name-prefix: doc-check
+          coder-task-prompt: ${{ steps.extract-context.outputs.task_prompt }}
+          github-user-id: ${{ steps.determine-context.outputs.github_user_id }}
+          github-token: ${{ github.token }}
+          github-issue-url: ${{ steps.determine-context.outputs.pr_url }}
+          comment-on-issue: true
+
+      - name: Write outputs
+        env:
+          TASK_CREATED: ${{ steps.create_task.outputs.task-created }}
+          TASK_NAME: ${{ steps.create_task.outputs.task-name }}
+          TASK_URL: ${{ steps.create_task.outputs.task-url }}
+          PR_URL: ${{ steps.determine-context.outputs.pr_url }}
+        run: |
+          {
+            echo "## Documentation Check Task"
+            echo ""
+            echo "**PR:** ${PR_URL}"
+            echo "**Task created:** ${TASK_CREATED}"
+            echo "**Task name:** ${TASK_NAME}"
+            echo "**Task URL:** ${TASK_URL}"
+            echo ""
+            echo "The Coder task is analyzing the PR changes and will comment with documentation recommendations."
+          } >> "${GITHUB_STEP_SUMMARY}"

.github/workflows/docker-base.yaml

@@ -38,7 +38,7 @@ jobs:
     if: github.repository_owner == 'coder'
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 

.github/workflows/docs-ci.yaml

@@ -30,7 +30,7 @@ jobs:
       - name: Setup Node
         uses: ./.github/actions/setup-node
 
-      - uses: tj-actions/changed-files@dbf178ceecb9304128c8e0648591d71208c6e2c9 # v45.0.7
+      - uses: tj-actions/changed-files@70069877f29101175ed2b055d210fe8b1d54d7d7 # v45.0.7
         id: changed-files
         with:
           files: |

.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@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -40,7 +40,7 @@ jobs:
         with:
           # Pinning to 2.28 here, as Nix gets a "error: [json.exception.type_error.302] type must be array, but is string"
           # on version 2.29 and above.
-          nix_version: "2.28.4"
+          nix_version: "2.28.5"
 
       - uses: nix-community/cache-nix-action@135667ec418502fa5a3598af6fb9eb733888ce6a # v6.1.3
         with:
@@ -125,7 +125,7 @@ jobs:
       id-token: write
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 

.github/workflows/nightly-gauntlet.yaml

@@ -27,7 +27,7 @@ jobs:
           - windows-2022
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         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@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 

.github/workflows/pr-cleanup.yaml

@@ -19,7 +19,7 @@ jobs:
       packages: write
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         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@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -76,7 +76,7 @@ jobs:
     runs-on: "ubuntu-latest"
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         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@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         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@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         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@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 

.github/workflows/release-validation.yaml

@@ -14,7 +14,7 @@ jobs:
 
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 

.github/workflows/release.yaml

@@ -164,7 +164,7 @@ jobs:
       version: ${{ steps.version.outputs.version }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -785,7 +785,7 @@ jobs:
 
       - name: Send repository-dispatch event
         if: ${{ !inputs.dry_run }}
-        uses: peter-evans/repository-dispatch@5fc4efd1a4797ddb68ffd0714a238564e4cc0e6f # v4.0.0
+        uses: peter-evans/repository-dispatch@28959ce8df70de7be546dd1250a005dd32156697 # v4.0.1
         with:
           token: ${{ secrets.CDRCI_GITHUB_TOKEN }}
           repository: coder/packages
@@ -802,7 +802,7 @@ jobs:
       # TODO: skip this if it's not a new release (i.e. a backport). This is
       #       fine right now because it just makes a PR that we can close.
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -878,7 +878,7 @@ jobs:
 
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -971,7 +971,7 @@ jobs:
     if: ${{ !inputs.dry_run }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 

.github/workflows/scorecard.yml

@@ -20,7 +20,7 @@ jobs:
 
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         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@4e94bd11f71e507f7f87df81788dff88d1dacbfb # v3.29.5
+        uses: github/codeql-action/upload-sarif@014f16e7ab1402f30e7c3329d33797e7948572db # 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@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -40,7 +40,7 @@ jobs:
         uses: ./.github/actions/setup-go
 
       - name: Initialize CodeQL
-        uses: github/codeql-action/init@4e94bd11f71e507f7f87df81788dff88d1dacbfb # v3.29.5
+        uses: github/codeql-action/init@014f16e7ab1402f30e7c3329d33797e7948572db # v3.29.5
         with:
           languages: go, javascript
 
@@ -50,7 +50,7 @@ jobs:
           rm Makefile
 
       - name: Perform CodeQL Analysis
-        uses: github/codeql-action/analyze@4e94bd11f71e507f7f87df81788dff88d1dacbfb # v3.29.5
+        uses: github/codeql-action/analyze@014f16e7ab1402f30e7c3329d33797e7948572db # v3.29.5
 
       - name: Send Slack notification on failure
         if: ${{ failure() }}
@@ -69,7 +69,7 @@ jobs:
     runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -154,7 +154,7 @@ jobs:
           severity: "CRITICAL,HIGH"
 
       - name: Upload Trivy scan results to GitHub Security tab
-        uses: github/codeql-action/upload-sarif@4e94bd11f71e507f7f87df81788dff88d1dacbfb # v3.29.5
+        uses: github/codeql-action/upload-sarif@014f16e7ab1402f30e7c3329d33797e7948572db # v3.29.5
         with:
           sarif_file: trivy-results.sarif
           category: "Trivy"

.github/workflows/stale.yaml

@@ -18,7 +18,7 @@ jobs:
       pull-requests: write
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -96,7 +96,7 @@ jobs:
       contents: write
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
@@ -120,12 +120,12 @@ jobs:
       actions: write
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 
       - name: Delete PR Cleanup workflow runs
-        uses: Mattraks/delete-workflow-runs@ab482449ba468316e9a8801e092d0405715c5e6d # v2.1.0
+        uses: Mattraks/delete-workflow-runs@5bf9a1dac5c4d041c029f0a8370ddf0c5cb5aeb7 # v2.1.0
         with:
           token: ${{ github.token }}
           repository: ${{ github.repository }}
@@ -134,7 +134,7 @@ jobs:
           delete_workflow_pattern: pr-cleanup.yaml
 
       - name: Delete PR Deploy workflow skipped runs
-        uses: Mattraks/delete-workflow-runs@ab482449ba468316e9a8801e092d0405715c5e6d # v2.1.0
+        uses: Mattraks/delete-workflow-runs@5bf9a1dac5c4d041c029f0a8370ddf0c5cb5aeb7 # v2.1.0
         with:
           token: ${{ github.token }}
           repository: ${{ github.repository }}

.github/workflows/traiage.yaml

@@ -17,8 +17,8 @@ on:
         type: string
       template_preset:
         description: "Template preset to use"
-        required: true
-        default: "none"
+        required: false
+        default: ""
         type: string
       prefix:
         description: "Prefix for workspace name"
@@ -67,7 +67,7 @@ jobs:
           GITHUB_EVENT_USER_LOGIN: ${{ github.event.sender.login }}
           INPUTS_ISSUE_URL: ${{ inputs.issue_url }}
           INPUTS_TEMPLATE_NAME: ${{ inputs.template_name || 'coder' }}
-          INPUTS_TEMPLATE_PRESET: ${{ inputs.template_preset || 'none'}}
+          INPUTS_TEMPLATE_PRESET: ${{ inputs.template_preset || ''}}
           INPUTS_PREFIX: ${{ inputs.prefix || 'traiage' }}
           GH_TOKEN: ${{ github.token }}
         run: |
@@ -124,7 +124,7 @@ jobs:
             exit 1
           fi
 
-      - name: Extract context key from issue
+      - name: Extract context key and description from issue
         id: extract-context
         env:
           ISSUE_URL: ${{ steps.determine-inputs.outputs.issue_url }}
@@ -132,86 +132,59 @@ jobs:
         run: |
           issue_number="$(gh issue view "${ISSUE_URL}" --json number --jq '.number')"
           context_key="gh-${issue_number}"
-          echo "context_key=${context_key}" >> "${GITHUB_OUTPUT}"
-          echo "CONTEXT_KEY=${context_key}" >> "${GITHUB_ENV}"
 
-      - name: Download and install Coder binary
-        shell: bash
-        env:
-          CODER_URL: ${{ secrets.TRAIAGE_CODER_URL }}
-        run: |
-          if [ "${{ runner.arch }}" == "ARM64" ]; then
-            ARCH="arm64"
-          else
-            ARCH="amd64"
-          fi
-          mkdir -p "${HOME}/.local/bin"
-          curl -fsSL --compressed "$CODER_URL/bin/coder-linux-${ARCH}" -o "${HOME}/.local/bin/coder"
-          chmod +x "${HOME}/.local/bin/coder"
-          export PATH="$HOME/.local/bin:$PATH"
-          coder version
-          coder whoami
-          echo "$HOME/.local/bin" >> "${GITHUB_PATH}"
+          TASK_PROMPT=$(cat <<EOF
+          Fix ${ISSUE_URL}
 
-      - name: Get Coder username from GitHub actor
-        id: get-coder-username
-        env:
-          CODER_SESSION_TOKEN: ${{ secrets.TRAIAGE_CODER_SESSION_TOKEN }}
-          GH_TOKEN: ${{ github.token }}
-          GITHUB_USER_ID: ${{ steps.determine-inputs.outputs.github_user_id }}
-        run: |
-          user_json=$(
-            coder users list --github-user-id="${GITHUB_USER_ID}" --output=json
+            1. Use the gh CLI to read the issue description and comments.
+            2. Think carefully and try to understand the root cause. If the issue is unclear or not well defined, ask me to clarify and provide more information.
+            3. Write a proposed implementation plan to PLAN.md for me to review before starting implementation. Your plan should use TDD and only make the minimal changes necessary to fix the root cause.
+            4. When I approve your plan, start working on it. If you encounter issues with the plan, ask me for clarification and update the plan as required.
+            5. When you have finished implementation according to the plan, commit and push your changes, and create a PR using the gh CLI for me to review.
+
+          EOF
           )
-          coder_username=$(jq -r 'first | .username' <<< "$user_json")
-          [[ -z "${coder_username}" || "${coder_username}" == "null" ]] && echo "No Coder user with GitHub user ID ${GITHUB_USER_ID} found" && exit 1
-          echo "coder_username=${coder_username}" >> "${GITHUB_OUTPUT}"
+
+          echo "context_key=${context_key}" >> "${GITHUB_OUTPUT}"
+          {
+            echo "TASK_PROMPT<<EOF"
+            echo "${TASK_PROMPT}"
+            echo "EOF"
+          } >> "${GITHUB_OUTPUT}"
 
       - name: Checkout repository
         uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
         with:
+          fetch-depth: 1
+          path: ./.github/actions/create-task-action
           persist-credentials: false
-          fetch-depth: 0
+          ref: main
+          repository: coder/create-task-action
 
-      # TODO(Cian): this is a good use-case for 'recipes'
-      - name: Create Coder task
-        id: create-task
+      - name: Create Coder Task
+        id: create_task
+        uses: ./.github/actions/create-task-action
+        with:
+          coder-url: ${{ secrets.TRAIAGE_CODER_URL }}
+          coder-token: ${{ secrets.TRAIAGE_CODER_SESSION_TOKEN }}
+          coder-organization: "default"
+          coder-template-name: coder
+          coder-template-preset: ${{ steps.determine-inputs.outputs.template_preset }}
+          coder-task-name-prefix: gh-coder
+          coder-task-prompt: ${{ steps.extract-context.outputs.task_prompt }}
+          github-user-id: ${{ steps.determine-inputs.outputs.github_user_id }}
+          github-token: ${{ github.token }}
+          github-issue-url: ${{ steps.determine-inputs.outputs.issue_url }}
+          comment-on-issue: ${{ startsWith(steps.determine-inputs.outputs.issue_url, format('{0}/{1}', github.server_url, github.repository)) }}
+
+      - name: Write outputs
         env:
-          CODER_USERNAME: ${{ steps.get-coder-username.outputs.coder_username }}
-          CONTEXT_KEY: ${{ steps.extract-context.outputs.context_key }}
-          GH_TOKEN: ${{ github.token }}
-          GITHUB_REPOSITORY: ${{ github.repository }}
-          ISSUE_URL: ${{ steps.determine-inputs.outputs.issue_url }}
-          PREFIX: ${{ steps.determine-inputs.outputs.prefix }}
-          RUN_ID: ${{ github.run_id }}
-          TEMPLATE_NAME: ${{ steps.determine-inputs.outputs.template_name }}
-          TEMPLATE_PARAMETERS: ${{ secrets.TRAIAGE_TEMPLATE_PARAMETERS }}
-          TEMPLATE_PRESET: ${{ steps.determine-inputs.outputs.template_preset }}
+          TASK_CREATED: ${{ steps.create_task.outputs.task-created }}
+          TASK_NAME: ${{ steps.create_task.outputs.task-name }}
+          TASK_URL: ${{ steps.create_task.outputs.task-url }}
         run: |
-          # Fetch issue description using `gh` CLI
-          #shellcheck disable=SC2016 # The template string should not be subject to shell expansion
-          issue_description=$(gh issue view "${ISSUE_URL}" \
-            --json 'title,body,comments' \
-            --template '{{printf "%s\n\n%s\n\nComments:\n" .title .body}}{{range $k, $v := .comments}}  - {{index $v.author "login"}}: {{printf "%s\n" $v.body}}{{end}}')
-
-          # Write a prompt to PROMPT_FILE
-          PROMPT=$(cat <<EOF
-          Fix ${ISSUE_URL}
-
-          Analyze the below GitHub issue description, understand the root cause, and make appropriate changes to resolve the issue.
-          ---
-          ${issue_description}
-          EOF
-          )
-          export PROMPT
-
-          export TASK_NAME="${PREFIX}-${CONTEXT_KEY}-${RUN_ID}"
-          echo "Creating task: $TASK_NAME"
-          ./scripts/traiage.sh create
-          if [[ "${ISSUE_URL}" == "https://github.com/${GITHUB_REPOSITORY}"* ]]; then
-            gh issue comment "${ISSUE_URL}" --body "Task created: https://dev.coder.com/tasks/${CODER_USERNAME}/${TASK_NAME}" --create-if-none --edit-last
-          else
-            echo "Skipping comment on other repo."
-          fi
-          echo "TASK_NAME=${CODER_USERNAME}/${TASK_NAME}" >> "${GITHUB_OUTPUT}"
-          echo "TASK_NAME=${CODER_USERNAME}/${TASK_NAME}" >> "${GITHUB_ENV}"
+          {
+            echo "**Task created:** ${TASK_CREATED}"
+            echo "**Task name:**    ${TASK_NAME}"
+            echo "**Task URL**:     ${TASK_URL}"
+          } >> "${GITHUB_STEP_SUMMARY}"

.github/workflows/typos.toml

@@ -9,6 +9,7 @@ IST = "IST"
 MacOS = "macOS"
 AKS = "AKS"
 O_WRONLY = "O_WRONLY"
+AIBridge = "AI Bridge"
 
 [default.extend-words]
 AKS = "AKS"

.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@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
         with:
           egress-policy: audit
 

.gitignore

@@ -91,3 +91,6 @@ __debug_bin*
 **/.claude/settings.local.json
 
 /.env
+
+# Ignore plans written by AI agents.
+PLAN.md

Makefile

@@ -636,16 +636,17 @@ TAILNETTEST_MOCKS := \
 	tailnet/tailnettest/subscriptionmock.go
 
 AIBRIDGED_MOCKS := \
-	enterprise/x/aibridged/aibridgedmock/clientmock.go \
-	enterprise/x/aibridged/aibridgedmock/poolmock.go
+	enterprise/aibridged/aibridgedmock/clientmock.go \
+	enterprise/aibridged/aibridgedmock/poolmock.go
 
 GEN_FILES := \
 	tailnet/proto/tailnet.pb.go \
 	agent/proto/agent.pb.go \
+	agent/agentsocket/proto/agentsocket.pb.go \
 	provisionersdk/proto/provisioner.pb.go \
 	provisionerd/proto/provisionerd.pb.go \
 	vpn/vpn.pb.go \
-	enterprise/x/aibridged/proto/aibridged.pb.go \
+	enterprise/aibridged/proto/aibridged.pb.go \
 	$(DB_GEN_FILES) \
 	$(SITE_GEN_FILES) \
 	coderd/rbac/object_gen.go \
@@ -696,8 +697,9 @@ gen/mark-fresh:
 		agent/proto/agent.pb.go \
 		provisionersdk/proto/provisioner.pb.go \
 		provisionerd/proto/provisionerd.pb.go \
+		agent/agentsocket/proto/agentsocket.pb.go \
 		vpn/vpn.pb.go \
-		enterprise/x/aibridged/proto/aibridged.pb.go \
+		enterprise/aibridged/proto/aibridged.pb.go \
 		coderd/database/dump.sql \
 		$(DB_GEN_FILES) \
 		site/src/api/typesGenerated.ts \
@@ -768,8 +770,8 @@ codersdk/workspacesdk/agentconnmock/agentconnmock.go: codersdk/workspacesdk/agen
 	go generate ./codersdk/workspacesdk/agentconnmock/
 	touch "$@"
 
-$(AIBRIDGED_MOCKS): enterprise/x/aibridged/client.go enterprise/x/aibridged/pool.go
-	go generate ./enterprise/x/aibridged/aibridgedmock/
+$(AIBRIDGED_MOCKS): enterprise/aibridged/client.go enterprise/aibridged/pool.go
+	go generate ./enterprise/aibridged/aibridgedmock/
 	touch "$@"
 
 agent/agentcontainers/dcspec/dcspec_gen.go: \
@@ -800,6 +802,14 @@ agent/proto/agent.pb.go: agent/proto/agent.proto
 		--go-drpc_opt=paths=source_relative \
 		./agent/proto/agent.proto
 
+agent/agentsocket/proto/agentsocket.pb.go: agent/agentsocket/proto/agentsocket.proto
+	protoc \
+		--go_out=. \
+		--go_opt=paths=source_relative \
+		--go-drpc_out=. \
+		--go-drpc_opt=paths=source_relative \
+		./agent/agentsocket/proto/agentsocket.proto
+
 provisionersdk/proto/provisioner.pb.go: provisionersdk/proto/provisioner.proto
 	protoc \
 		--go_out=. \
@@ -822,13 +832,13 @@ vpn/vpn.pb.go: vpn/vpn.proto
 		--go_opt=paths=source_relative \
 		./vpn/vpn.proto
 
-enterprise/x/aibridged/proto/aibridged.pb.go: enterprise/x/aibridged/proto/aibridged.proto
+enterprise/aibridged/proto/aibridged.pb.go: enterprise/aibridged/proto/aibridged.proto
 	protoc \
 		--go_out=. \
 		--go_opt=paths=source_relative \
 		--go-drpc_out=. \
 		--go-drpc_opt=paths=source_relative \
-		./enterprise/x/aibridged/proto/aibridged.proto
+		./enterprise/aibridged/proto/aibridged.proto
 
 site/src/api/typesGenerated.ts: site/node_modules/.installed $(wildcard scripts/apitypings/*) $(shell find ./codersdk $(FIND_EXCLUSIONS) -type f -name '*.go')
 	# -C sets the directory for the go run command

agent/agentcontainers/api.go

@@ -682,8 +682,6 @@ func (api *API) updaterLoop() {
 			} else {
 				prevErr = nil
 			}
-		default:
-			api.logger.Debug(api.ctx, "updater loop ticker skipped, update in progress")
 		}
 
 		return nil // Always nil to keep the ticker going.

agent/agentsocket/proto/agentsocket.pb.go

@@ -0,0 +1,968 @@
+// Code generated by protoc-gen-go. DO NOT EDIT.
+// versions:
+// 	protoc-gen-go v1.30.0
+// 	protoc        v4.23.4
+// source: agent/agentsocket/proto/agentsocket.proto
+
+package proto
+
+import (
+	protoreflect "google.golang.org/protobuf/reflect/protoreflect"
+	protoimpl "google.golang.org/protobuf/runtime/protoimpl"
+	reflect "reflect"
+	sync "sync"
+)
+
+const (
+	// Verify that this generated code is sufficiently up-to-date.
+	_ = protoimpl.EnforceVersion(20 - protoimpl.MinVersion)
+	// Verify that runtime/protoimpl is sufficiently up-to-date.
+	_ = protoimpl.EnforceVersion(protoimpl.MaxVersion - 20)
+)
+
+type PingRequest struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+}
+
+func (x *PingRequest) Reset() {
+	*x = PingRequest{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[0]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *PingRequest) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*PingRequest) ProtoMessage() {}
+
+func (x *PingRequest) ProtoReflect() protoreflect.Message {
+	mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[0]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use PingRequest.ProtoReflect.Descriptor instead.
+func (*PingRequest) Descriptor() ([]byte, []int) {
+	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{0}
+}
+
+type PingResponse struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+}
+
+func (x *PingResponse) Reset() {
+	*x = PingResponse{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[1]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *PingResponse) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*PingResponse) ProtoMessage() {}
+
+func (x *PingResponse) ProtoReflect() protoreflect.Message {
+	mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[1]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use PingResponse.ProtoReflect.Descriptor instead.
+func (*PingResponse) Descriptor() ([]byte, []int) {
+	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{1}
+}
+
+type SyncStartRequest struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+
+	Unit string `protobuf:"bytes,1,opt,name=unit,proto3" json:"unit,omitempty"`
+}
+
+func (x *SyncStartRequest) Reset() {
+	*x = SyncStartRequest{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[2]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *SyncStartRequest) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*SyncStartRequest) ProtoMessage() {}
+
+func (x *SyncStartRequest) ProtoReflect() protoreflect.Message {
+	mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[2]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use SyncStartRequest.ProtoReflect.Descriptor instead.
+func (*SyncStartRequest) Descriptor() ([]byte, []int) {
+	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{2}
+}
+
+func (x *SyncStartRequest) GetUnit() string {
+	if x != nil {
+		return x.Unit
+	}
+	return ""
+}
+
+type SyncStartResponse struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+}
+
+func (x *SyncStartResponse) Reset() {
+	*x = SyncStartResponse{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[3]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *SyncStartResponse) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*SyncStartResponse) ProtoMessage() {}
+
+func (x *SyncStartResponse) ProtoReflect() protoreflect.Message {
+	mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[3]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use SyncStartResponse.ProtoReflect.Descriptor instead.
+func (*SyncStartResponse) Descriptor() ([]byte, []int) {
+	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{3}
+}
+
+type SyncWantRequest struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+
+	Unit      string `protobuf:"bytes,1,opt,name=unit,proto3" json:"unit,omitempty"`
+	DependsOn string `protobuf:"bytes,2,opt,name=depends_on,json=dependsOn,proto3" json:"depends_on,omitempty"`
+}
+
+func (x *SyncWantRequest) Reset() {
+	*x = SyncWantRequest{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[4]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *SyncWantRequest) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*SyncWantRequest) ProtoMessage() {}
+
+func (x *SyncWantRequest) ProtoReflect() protoreflect.Message {
+	mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[4]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use SyncWantRequest.ProtoReflect.Descriptor instead.
+func (*SyncWantRequest) Descriptor() ([]byte, []int) {
+	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{4}
+}
+
+func (x *SyncWantRequest) GetUnit() string {
+	if x != nil {
+		return x.Unit
+	}
+	return ""
+}
+
+func (x *SyncWantRequest) GetDependsOn() string {
+	if x != nil {
+		return x.DependsOn
+	}
+	return ""
+}
+
+type SyncWantResponse struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+}
+
+func (x *SyncWantResponse) Reset() {
+	*x = SyncWantResponse{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[5]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *SyncWantResponse) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*SyncWantResponse) ProtoMessage() {}
+
+func (x *SyncWantResponse) ProtoReflect() protoreflect.Message {
+	mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[5]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use SyncWantResponse.ProtoReflect.Descriptor instead.
+func (*SyncWantResponse) Descriptor() ([]byte, []int) {
+	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{5}
+}
+
+type SyncCompleteRequest struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+
+	Unit string `protobuf:"bytes,1,opt,name=unit,proto3" json:"unit,omitempty"`
+}
+
+func (x *SyncCompleteRequest) Reset() {
+	*x = SyncCompleteRequest{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[6]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *SyncCompleteRequest) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*SyncCompleteRequest) ProtoMessage() {}
+
+func (x *SyncCompleteRequest) ProtoReflect() protoreflect.Message {
+	mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[6]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use SyncCompleteRequest.ProtoReflect.Descriptor instead.
+func (*SyncCompleteRequest) Descriptor() ([]byte, []int) {
+	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{6}
+}
+
+func (x *SyncCompleteRequest) GetUnit() string {
+	if x != nil {
+		return x.Unit
+	}
+	return ""
+}
+
+type SyncCompleteResponse struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+}
+
+func (x *SyncCompleteResponse) Reset() {
+	*x = SyncCompleteResponse{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[7]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *SyncCompleteResponse) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*SyncCompleteResponse) ProtoMessage() {}
+
+func (x *SyncCompleteResponse) ProtoReflect() protoreflect.Message {
+	mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[7]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use SyncCompleteResponse.ProtoReflect.Descriptor instead.
+func (*SyncCompleteResponse) Descriptor() ([]byte, []int) {
+	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{7}
+}
+
+type SyncReadyRequest struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+
+	Unit string `protobuf:"bytes,1,opt,name=unit,proto3" json:"unit,omitempty"`
+}
+
+func (x *SyncReadyRequest) Reset() {
+	*x = SyncReadyRequest{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[8]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *SyncReadyRequest) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*SyncReadyRequest) ProtoMessage() {}
+
+func (x *SyncReadyRequest) ProtoReflect() protoreflect.Message {
+	mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[8]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use SyncReadyRequest.ProtoReflect.Descriptor instead.
+func (*SyncReadyRequest) Descriptor() ([]byte, []int) {
+	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{8}
+}
+
+func (x *SyncReadyRequest) GetUnit() string {
+	if x != nil {
+		return x.Unit
+	}
+	return ""
+}
+
+type SyncReadyResponse struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+
+	Ready bool `protobuf:"varint,1,opt,name=ready,proto3" json:"ready,omitempty"`
+}
+
+func (x *SyncReadyResponse) Reset() {
+	*x = SyncReadyResponse{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[9]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *SyncReadyResponse) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*SyncReadyResponse) ProtoMessage() {}
+
+func (x *SyncReadyResponse) ProtoReflect() protoreflect.Message {
+	mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[9]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use SyncReadyResponse.ProtoReflect.Descriptor instead.
+func (*SyncReadyResponse) Descriptor() ([]byte, []int) {
+	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{9}
+}
+
+func (x *SyncReadyResponse) GetReady() bool {
+	if x != nil {
+		return x.Ready
+	}
+	return false
+}
+
+type SyncStatusRequest struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+
+	Unit string `protobuf:"bytes,1,opt,name=unit,proto3" json:"unit,omitempty"`
+}
+
+func (x *SyncStatusRequest) Reset() {
+	*x = SyncStatusRequest{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[10]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *SyncStatusRequest) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*SyncStatusRequest) ProtoMessage() {}
+
+func (x *SyncStatusRequest) ProtoReflect() protoreflect.Message {
+	mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[10]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use SyncStatusRequest.ProtoReflect.Descriptor instead.
+func (*SyncStatusRequest) Descriptor() ([]byte, []int) {
+	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{10}
+}
+
+func (x *SyncStatusRequest) GetUnit() string {
+	if x != nil {
+		return x.Unit
+	}
+	return ""
+}
+
+type DependencyInfo struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+
+	Unit           string `protobuf:"bytes,1,opt,name=unit,proto3" json:"unit,omitempty"`
+	DependsOn      string `protobuf:"bytes,2,opt,name=depends_on,json=dependsOn,proto3" json:"depends_on,omitempty"`
+	RequiredStatus string `protobuf:"bytes,3,opt,name=required_status,json=requiredStatus,proto3" json:"required_status,omitempty"`
+	CurrentStatus  string `protobuf:"bytes,4,opt,name=current_status,json=currentStatus,proto3" json:"current_status,omitempty"`
+	IsSatisfied    bool   `protobuf:"varint,5,opt,name=is_satisfied,json=isSatisfied,proto3" json:"is_satisfied,omitempty"`
+}
+
+func (x *DependencyInfo) Reset() {
+	*x = DependencyInfo{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[11]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *DependencyInfo) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*DependencyInfo) ProtoMessage() {}
+
+func (x *DependencyInfo) ProtoReflect() protoreflect.Message {
+	mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[11]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use DependencyInfo.ProtoReflect.Descriptor instead.
+func (*DependencyInfo) Descriptor() ([]byte, []int) {
+	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{11}
+}
+
+func (x *DependencyInfo) GetUnit() string {
+	if x != nil {
+		return x.Unit
+	}
+	return ""
+}
+
+func (x *DependencyInfo) GetDependsOn() string {
+	if x != nil {
+		return x.DependsOn
+	}
+	return ""
+}
+
+func (x *DependencyInfo) GetRequiredStatus() string {
+	if x != nil {
+		return x.RequiredStatus
+	}
+	return ""
+}
+
+func (x *DependencyInfo) GetCurrentStatus() string {
+	if x != nil {
+		return x.CurrentStatus
+	}
+	return ""
+}
+
+func (x *DependencyInfo) GetIsSatisfied() bool {
+	if x != nil {
+		return x.IsSatisfied
+	}
+	return false
+}
+
+type SyncStatusResponse struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+
+	Status       string            `protobuf:"bytes,1,opt,name=status,proto3" json:"status,omitempty"`
+	IsReady      bool              `protobuf:"varint,2,opt,name=is_ready,json=isReady,proto3" json:"is_ready,omitempty"`
+	Dependencies []*DependencyInfo `protobuf:"bytes,3,rep,name=dependencies,proto3" json:"dependencies,omitempty"`
+}
+
+func (x *SyncStatusResponse) Reset() {
+	*x = SyncStatusResponse{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[12]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *SyncStatusResponse) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*SyncStatusResponse) ProtoMessage() {}
+
+func (x *SyncStatusResponse) ProtoReflect() protoreflect.Message {
+	mi := &file_agent_agentsocket_proto_agentsocket_proto_msgTypes[12]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use SyncStatusResponse.ProtoReflect.Descriptor instead.
+func (*SyncStatusResponse) Descriptor() ([]byte, []int) {
+	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{12}
+}
+
+func (x *SyncStatusResponse) GetStatus() string {
+	if x != nil {
+		return x.Status
+	}
+	return ""
+}
+
+func (x *SyncStatusResponse) GetIsReady() bool {
+	if x != nil {
+		return x.IsReady
+	}
+	return false
+}
+
+func (x *SyncStatusResponse) GetDependencies() []*DependencyInfo {
+	if x != nil {
+		return x.Dependencies
+	}
+	return nil
+}
+
+var File_agent_agentsocket_proto_agentsocket_proto protoreflect.FileDescriptor
+
+var file_agent_agentsocket_proto_agentsocket_proto_rawDesc = []byte{
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+}
+
+var (
+	file_agent_agentsocket_proto_agentsocket_proto_rawDescOnce sync.Once
+	file_agent_agentsocket_proto_agentsocket_proto_rawDescData = file_agent_agentsocket_proto_agentsocket_proto_rawDesc
+)
+
+func file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP() []byte {
+	file_agent_agentsocket_proto_agentsocket_proto_rawDescOnce.Do(func() {
+		file_agent_agentsocket_proto_agentsocket_proto_rawDescData = protoimpl.X.CompressGZIP(file_agent_agentsocket_proto_agentsocket_proto_rawDescData)
+	})
+	return file_agent_agentsocket_proto_agentsocket_proto_rawDescData
+}
+
+var file_agent_agentsocket_proto_agentsocket_proto_msgTypes = make([]protoimpl.MessageInfo, 13)
+var file_agent_agentsocket_proto_agentsocket_proto_goTypes = []interface{}{
+	(*PingRequest)(nil),          // 0: coder.agentsocket.v1.PingRequest
+	(*PingResponse)(nil),         // 1: coder.agentsocket.v1.PingResponse
+	(*SyncStartRequest)(nil),     // 2: coder.agentsocket.v1.SyncStartRequest
+	(*SyncStartResponse)(nil),    // 3: coder.agentsocket.v1.SyncStartResponse
+	(*SyncWantRequest)(nil),      // 4: coder.agentsocket.v1.SyncWantRequest
+	(*SyncWantResponse)(nil),     // 5: coder.agentsocket.v1.SyncWantResponse
+	(*SyncCompleteRequest)(nil),  // 6: coder.agentsocket.v1.SyncCompleteRequest
+	(*SyncCompleteResponse)(nil), // 7: coder.agentsocket.v1.SyncCompleteResponse
+	(*SyncReadyRequest)(nil),     // 8: coder.agentsocket.v1.SyncReadyRequest
+	(*SyncReadyResponse)(nil),    // 9: coder.agentsocket.v1.SyncReadyResponse
+	(*SyncStatusRequest)(nil),    // 10: coder.agentsocket.v1.SyncStatusRequest
+	(*DependencyInfo)(nil),       // 11: coder.agentsocket.v1.DependencyInfo
+	(*SyncStatusResponse)(nil),   // 12: coder.agentsocket.v1.SyncStatusResponse
+}
+var file_agent_agentsocket_proto_agentsocket_proto_depIdxs = []int32{
+	11, // 0: coder.agentsocket.v1.SyncStatusResponse.dependencies:type_name -> coder.agentsocket.v1.DependencyInfo
+	0,  // 1: coder.agentsocket.v1.AgentSocket.Ping:input_type -> coder.agentsocket.v1.PingRequest
+	2,  // 2: coder.agentsocket.v1.AgentSocket.SyncStart:input_type -> coder.agentsocket.v1.SyncStartRequest
+	4,  // 3: coder.agentsocket.v1.AgentSocket.SyncWant:input_type -> coder.agentsocket.v1.SyncWantRequest
+	6,  // 4: coder.agentsocket.v1.AgentSocket.SyncComplete:input_type -> coder.agentsocket.v1.SyncCompleteRequest
+	8,  // 5: coder.agentsocket.v1.AgentSocket.SyncReady:input_type -> coder.agentsocket.v1.SyncReadyRequest
+	10, // 6: coder.agentsocket.v1.AgentSocket.SyncStatus:input_type -> coder.agentsocket.v1.SyncStatusRequest
+	1,  // 7: coder.agentsocket.v1.AgentSocket.Ping:output_type -> coder.agentsocket.v1.PingResponse
+	3,  // 8: coder.agentsocket.v1.AgentSocket.SyncStart:output_type -> coder.agentsocket.v1.SyncStartResponse
+	5,  // 9: coder.agentsocket.v1.AgentSocket.SyncWant:output_type -> coder.agentsocket.v1.SyncWantResponse
+	7,  // 10: coder.agentsocket.v1.AgentSocket.SyncComplete:output_type -> coder.agentsocket.v1.SyncCompleteResponse
+	9,  // 11: coder.agentsocket.v1.AgentSocket.SyncReady:output_type -> coder.agentsocket.v1.SyncReadyResponse
+	12, // 12: coder.agentsocket.v1.AgentSocket.SyncStatus:output_type -> coder.agentsocket.v1.SyncStatusResponse
+	7,  // [7:13] is the sub-list for method output_type
+	1,  // [1:7] is the sub-list for method input_type
+	1,  // [1:1] is the sub-list for extension type_name
+	1,  // [1:1] is the sub-list for extension extendee
+	0,  // [0:1] is the sub-list for field type_name
+}
+
+func init() { file_agent_agentsocket_proto_agentsocket_proto_init() }
+func file_agent_agentsocket_proto_agentsocket_proto_init() {
+	if File_agent_agentsocket_proto_agentsocket_proto != nil {
+		return
+	}
+	if !protoimpl.UnsafeEnabled {
+		file_agent_agentsocket_proto_agentsocket_proto_msgTypes[0].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*PingRequest); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+		file_agent_agentsocket_proto_agentsocket_proto_msgTypes[1].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*PingResponse); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+		file_agent_agentsocket_proto_agentsocket_proto_msgTypes[2].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*SyncStartRequest); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+		file_agent_agentsocket_proto_agentsocket_proto_msgTypes[3].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*SyncStartResponse); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+		file_agent_agentsocket_proto_agentsocket_proto_msgTypes[4].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*SyncWantRequest); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+		file_agent_agentsocket_proto_agentsocket_proto_msgTypes[5].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*SyncWantResponse); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+		file_agent_agentsocket_proto_agentsocket_proto_msgTypes[6].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*SyncCompleteRequest); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+		file_agent_agentsocket_proto_agentsocket_proto_msgTypes[7].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*SyncCompleteResponse); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+		file_agent_agentsocket_proto_agentsocket_proto_msgTypes[8].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*SyncReadyRequest); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+		file_agent_agentsocket_proto_agentsocket_proto_msgTypes[9].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*SyncReadyResponse); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+		file_agent_agentsocket_proto_agentsocket_proto_msgTypes[10].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*SyncStatusRequest); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+		file_agent_agentsocket_proto_agentsocket_proto_msgTypes[11].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*DependencyInfo); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+		file_agent_agentsocket_proto_agentsocket_proto_msgTypes[12].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*SyncStatusResponse); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+	}
+	type x struct{}
+	out := protoimpl.TypeBuilder{
+		File: protoimpl.DescBuilder{
+			GoPackagePath: reflect.TypeOf(x{}).PkgPath(),
+			RawDescriptor: file_agent_agentsocket_proto_agentsocket_proto_rawDesc,
+			NumEnums:      0,
+			NumMessages:   13,
+			NumExtensions: 0,
+			NumServices:   1,
+		},
+		GoTypes:           file_agent_agentsocket_proto_agentsocket_proto_goTypes,
+		DependencyIndexes: file_agent_agentsocket_proto_agentsocket_proto_depIdxs,
+		MessageInfos:      file_agent_agentsocket_proto_agentsocket_proto_msgTypes,
+	}.Build()
+	File_agent_agentsocket_proto_agentsocket_proto = out.File
+	file_agent_agentsocket_proto_agentsocket_proto_rawDesc = nil
+	file_agent_agentsocket_proto_agentsocket_proto_goTypes = nil
+	file_agent_agentsocket_proto_agentsocket_proto_depIdxs = nil
+}

agent/agentsocket/proto/agentsocket.proto

@@ -0,0 +1,69 @@
+syntax = "proto3";
+option go_package = "github.com/coder/coder/v2/agent/agentsocket/proto";
+
+package coder.agentsocket.v1;
+
+message PingRequest {}
+
+message PingResponse {}
+
+message SyncStartRequest {
+  string unit = 1;
+}
+
+message SyncStartResponse {}
+
+message SyncWantRequest {
+  string unit = 1;
+  string depends_on = 2;
+}
+
+message SyncWantResponse {}
+
+message SyncCompleteRequest {
+  string unit = 1;
+}
+
+message SyncCompleteResponse {}
+
+message SyncReadyRequest {
+  string unit = 1;
+}
+
+message SyncReadyResponse {
+  bool ready = 1;
+}
+
+message SyncStatusRequest {
+  string unit = 1;
+}
+
+message DependencyInfo {
+  string unit = 1;
+  string depends_on = 2;
+  string required_status = 3;
+  string current_status = 4;
+  bool is_satisfied = 5;
+}
+
+message SyncStatusResponse {
+  string status = 1;
+  bool is_ready = 2;
+  repeated DependencyInfo dependencies = 3;
+}
+
+// AgentSocket provides direct access to the agent over local IPC.
+service AgentSocket {
+  // Ping the agent to check if it is alive.
+  rpc Ping(PingRequest) returns (PingResponse);
+  // Report the start of a unit.
+  rpc SyncStart(SyncStartRequest) returns (SyncStartResponse);
+  // Declare a dependency between units.
+  rpc SyncWant(SyncWantRequest) returns (SyncWantResponse);
+  // Report the completion of a unit.
+  rpc SyncComplete(SyncCompleteRequest) returns (SyncCompleteResponse);
+  // Request whether a unit is ready to be started. That is, all dependencies are satisfied.
+  rpc SyncReady(SyncReadyRequest) returns (SyncReadyResponse);
+  // Get the status of a unit and list its dependencies.
+  rpc SyncStatus(SyncStatusRequest) returns (SyncStatusResponse);
+}

agent/agentsocket/proto/agentsocket_drpc.pb.go

@@ -0,0 +1,311 @@
+// Code generated by protoc-gen-go-drpc. DO NOT EDIT.
+// protoc-gen-go-drpc version: v0.0.34
+// source: agent/agentsocket/proto/agentsocket.proto
+
+package proto
+
+import (
+	context "context"
+	errors "errors"
+	protojson "google.golang.org/protobuf/encoding/protojson"
+	proto "google.golang.org/protobuf/proto"
+	drpc "storj.io/drpc"
+	drpcerr "storj.io/drpc/drpcerr"
+)
+
+type drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto struct{}
+
+func (drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto) Marshal(msg drpc.Message) ([]byte, error) {
+	return proto.Marshal(msg.(proto.Message))
+}
+
+func (drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto) MarshalAppend(buf []byte, msg drpc.Message) ([]byte, error) {
+	return proto.MarshalOptions{}.MarshalAppend(buf, msg.(proto.Message))
+}
+
+func (drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto) Unmarshal(buf []byte, msg drpc.Message) error {
+	return proto.Unmarshal(buf, msg.(proto.Message))
+}
+
+func (drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto) JSONMarshal(msg drpc.Message) ([]byte, error) {
+	return protojson.Marshal(msg.(proto.Message))
+}
+
+func (drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto) JSONUnmarshal(buf []byte, msg drpc.Message) error {
+	return protojson.Unmarshal(buf, msg.(proto.Message))
+}
+
+type DRPCAgentSocketClient interface {
+	DRPCConn() drpc.Conn
+
+	Ping(ctx context.Context, in *PingRequest) (*PingResponse, error)
+	SyncStart(ctx context.Context, in *SyncStartRequest) (*SyncStartResponse, error)
+	SyncWant(ctx context.Context, in *SyncWantRequest) (*SyncWantResponse, error)
+	SyncComplete(ctx context.Context, in *SyncCompleteRequest) (*SyncCompleteResponse, error)
+	SyncReady(ctx context.Context, in *SyncReadyRequest) (*SyncReadyResponse, error)
+	SyncStatus(ctx context.Context, in *SyncStatusRequest) (*SyncStatusResponse, error)
+}
+
+type drpcAgentSocketClient struct {
+	cc drpc.Conn
+}
+
+func NewDRPCAgentSocketClient(cc drpc.Conn) DRPCAgentSocketClient {
+	return &drpcAgentSocketClient{cc}
+}
+
+func (c *drpcAgentSocketClient) DRPCConn() drpc.Conn { return c.cc }
+
+func (c *drpcAgentSocketClient) Ping(ctx context.Context, in *PingRequest) (*PingResponse, error) {
+	out := new(PingResponse)
+	err := c.cc.Invoke(ctx, "/coder.agentsocket.v1.AgentSocket/Ping", drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{}, in, out)
+	if err != nil {
+		return nil, err
+	}
+	return out, nil
+}
+
+func (c *drpcAgentSocketClient) SyncStart(ctx context.Context, in *SyncStartRequest) (*SyncStartResponse, error) {
+	out := new(SyncStartResponse)
+	err := c.cc.Invoke(ctx, "/coder.agentsocket.v1.AgentSocket/SyncStart", drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{}, in, out)
+	if err != nil {
+		return nil, err
+	}
+	return out, nil
+}
+
+func (c *drpcAgentSocketClient) SyncWant(ctx context.Context, in *SyncWantRequest) (*SyncWantResponse, error) {
+	out := new(SyncWantResponse)
+	err := c.cc.Invoke(ctx, "/coder.agentsocket.v1.AgentSocket/SyncWant", drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{}, in, out)
+	if err != nil {
+		return nil, err
+	}
+	return out, nil
+}
+
+func (c *drpcAgentSocketClient) SyncComplete(ctx context.Context, in *SyncCompleteRequest) (*SyncCompleteResponse, error) {
+	out := new(SyncCompleteResponse)
+	err := c.cc.Invoke(ctx, "/coder.agentsocket.v1.AgentSocket/SyncComplete", drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{}, in, out)
+	if err != nil {
+		return nil, err
+	}
+	return out, nil
+}
+
+func (c *drpcAgentSocketClient) SyncReady(ctx context.Context, in *SyncReadyRequest) (*SyncReadyResponse, error) {
+	out := new(SyncReadyResponse)
+	err := c.cc.Invoke(ctx, "/coder.agentsocket.v1.AgentSocket/SyncReady", drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{}, in, out)
+	if err != nil {
+		return nil, err
+	}
+	return out, nil
+}
+
+func (c *drpcAgentSocketClient) SyncStatus(ctx context.Context, in *SyncStatusRequest) (*SyncStatusResponse, error) {
+	out := new(SyncStatusResponse)
+	err := c.cc.Invoke(ctx, "/coder.agentsocket.v1.AgentSocket/SyncStatus", drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{}, in, out)
+	if err != nil {
+		return nil, err
+	}
+	return out, nil
+}
+
+type DRPCAgentSocketServer interface {
+	Ping(context.Context, *PingRequest) (*PingResponse, error)
+	SyncStart(context.Context, *SyncStartRequest) (*SyncStartResponse, error)
+	SyncWant(context.Context, *SyncWantRequest) (*SyncWantResponse, error)
+	SyncComplete(context.Context, *SyncCompleteRequest) (*SyncCompleteResponse, error)
+	SyncReady(context.Context, *SyncReadyRequest) (*SyncReadyResponse, error)
+	SyncStatus(context.Context, *SyncStatusRequest) (*SyncStatusResponse, error)
+}
+
+type DRPCAgentSocketUnimplementedServer struct{}
+
+func (s *DRPCAgentSocketUnimplementedServer) Ping(context.Context, *PingRequest) (*PingResponse, error) {
+	return nil, drpcerr.WithCode(errors.New("Unimplemented"), drpcerr.Unimplemented)
+}
+
+func (s *DRPCAgentSocketUnimplementedServer) SyncStart(context.Context, *SyncStartRequest) (*SyncStartResponse, error) {
+	return nil, drpcerr.WithCode(errors.New("Unimplemented"), drpcerr.Unimplemented)
+}
+
+func (s *DRPCAgentSocketUnimplementedServer) SyncWant(context.Context, *SyncWantRequest) (*SyncWantResponse, error) {
+	return nil, drpcerr.WithCode(errors.New("Unimplemented"), drpcerr.Unimplemented)
+}
+
+func (s *DRPCAgentSocketUnimplementedServer) SyncComplete(context.Context, *SyncCompleteRequest) (*SyncCompleteResponse, error) {
+	return nil, drpcerr.WithCode(errors.New("Unimplemented"), drpcerr.Unimplemented)
+}
+
+func (s *DRPCAgentSocketUnimplementedServer) SyncReady(context.Context, *SyncReadyRequest) (*SyncReadyResponse, error) {
+	return nil, drpcerr.WithCode(errors.New("Unimplemented"), drpcerr.Unimplemented)
+}
+
+func (s *DRPCAgentSocketUnimplementedServer) SyncStatus(context.Context, *SyncStatusRequest) (*SyncStatusResponse, error) {
+	return nil, drpcerr.WithCode(errors.New("Unimplemented"), drpcerr.Unimplemented)
+}
+
+type DRPCAgentSocketDescription struct{}
+
+func (DRPCAgentSocketDescription) NumMethods() int { return 6 }
+
+func (DRPCAgentSocketDescription) Method(n int) (string, drpc.Encoding, drpc.Receiver, interface{}, bool) {
+	switch n {
+	case 0:
+		return "/coder.agentsocket.v1.AgentSocket/Ping", drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{},
+			func(srv interface{}, ctx context.Context, in1, in2 interface{}) (drpc.Message, error) {
+				return srv.(DRPCAgentSocketServer).
+					Ping(
+						ctx,
+						in1.(*PingRequest),
+					)
+			}, DRPCAgentSocketServer.Ping, true
+	case 1:
+		return "/coder.agentsocket.v1.AgentSocket/SyncStart", drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{},
+			func(srv interface{}, ctx context.Context, in1, in2 interface{}) (drpc.Message, error) {
+				return srv.(DRPCAgentSocketServer).
+					SyncStart(
+						ctx,
+						in1.(*SyncStartRequest),
+					)
+			}, DRPCAgentSocketServer.SyncStart, true
+	case 2:
+		return "/coder.agentsocket.v1.AgentSocket/SyncWant", drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{},
+			func(srv interface{}, ctx context.Context, in1, in2 interface{}) (drpc.Message, error) {
+				return srv.(DRPCAgentSocketServer).
+					SyncWant(
+						ctx,
+						in1.(*SyncWantRequest),
+					)
+			}, DRPCAgentSocketServer.SyncWant, true
+	case 3:
+		return "/coder.agentsocket.v1.AgentSocket/SyncComplete", drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{},
+			func(srv interface{}, ctx context.Context, in1, in2 interface{}) (drpc.Message, error) {
+				return srv.(DRPCAgentSocketServer).
+					SyncComplete(
+						ctx,
+						in1.(*SyncCompleteRequest),
+					)
+			}, DRPCAgentSocketServer.SyncComplete, true
+	case 4:
+		return "/coder.agentsocket.v1.AgentSocket/SyncReady", drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{},
+			func(srv interface{}, ctx context.Context, in1, in2 interface{}) (drpc.Message, error) {
+				return srv.(DRPCAgentSocketServer).
+					SyncReady(
+						ctx,
+						in1.(*SyncReadyRequest),
+					)
+			}, DRPCAgentSocketServer.SyncReady, true
+	case 5:
+		return "/coder.agentsocket.v1.AgentSocket/SyncStatus", drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{},
+			func(srv interface{}, ctx context.Context, in1, in2 interface{}) (drpc.Message, error) {
+				return srv.(DRPCAgentSocketServer).
+					SyncStatus(
+						ctx,
+						in1.(*SyncStatusRequest),
+					)
+			}, DRPCAgentSocketServer.SyncStatus, true
+	default:
+		return "", nil, nil, nil, false
+	}
+}
+
+func DRPCRegisterAgentSocket(mux drpc.Mux, impl DRPCAgentSocketServer) error {
+	return mux.Register(impl, DRPCAgentSocketDescription{})
+}
+
+type DRPCAgentSocket_PingStream interface {
+	drpc.Stream
+	SendAndClose(*PingResponse) error
+}
+
+type drpcAgentSocket_PingStream struct {
+	drpc.Stream
+}
+
+func (x *drpcAgentSocket_PingStream) SendAndClose(m *PingResponse) error {
+	if err := x.MsgSend(m, drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{}); err != nil {
+		return err
+	}
+	return x.CloseSend()
+}
+
+type DRPCAgentSocket_SyncStartStream interface {
+	drpc.Stream
+	SendAndClose(*SyncStartResponse) error
+}
+
+type drpcAgentSocket_SyncStartStream struct {
+	drpc.Stream
+}
+
+func (x *drpcAgentSocket_SyncStartStream) SendAndClose(m *SyncStartResponse) error {
+	if err := x.MsgSend(m, drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{}); err != nil {
+		return err
+	}
+	return x.CloseSend()
+}
+
+type DRPCAgentSocket_SyncWantStream interface {
+	drpc.Stream
+	SendAndClose(*SyncWantResponse) error
+}
+
+type drpcAgentSocket_SyncWantStream struct {
+	drpc.Stream
+}
+
+func (x *drpcAgentSocket_SyncWantStream) SendAndClose(m *SyncWantResponse) error {
+	if err := x.MsgSend(m, drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{}); err != nil {
+		return err
+	}
+	return x.CloseSend()
+}
+
+type DRPCAgentSocket_SyncCompleteStream interface {
+	drpc.Stream
+	SendAndClose(*SyncCompleteResponse) error
+}
+
+type drpcAgentSocket_SyncCompleteStream struct {
+	drpc.Stream
+}
+
+func (x *drpcAgentSocket_SyncCompleteStream) SendAndClose(m *SyncCompleteResponse) error {
+	if err := x.MsgSend(m, drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{}); err != nil {
+		return err
+	}
+	return x.CloseSend()
+}
+
+type DRPCAgentSocket_SyncReadyStream interface {
+	drpc.Stream
+	SendAndClose(*SyncReadyResponse) error
+}
+
+type drpcAgentSocket_SyncReadyStream struct {
+	drpc.Stream
+}
+
+func (x *drpcAgentSocket_SyncReadyStream) SendAndClose(m *SyncReadyResponse) error {
+	if err := x.MsgSend(m, drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{}); err != nil {
+		return err
+	}
+	return x.CloseSend()
+}
+
+type DRPCAgentSocket_SyncStatusStream interface {
+	drpc.Stream
+	SendAndClose(*SyncStatusResponse) error
+}
+
+type drpcAgentSocket_SyncStatusStream struct {
+	drpc.Stream
+}
+
+func (x *drpcAgentSocket_SyncStatusStream) SendAndClose(m *SyncStatusResponse) error {
+	if err := x.MsgSend(m, drpcEncoding_File_agent_agentsocket_proto_agentsocket_proto{}); err != nil {
+		return err
+	}
+	return x.CloseSend()
+}

agent/agentsocket/proto/version.go

@@ -0,0 +1,17 @@
+package proto
+
+import "github.com/coder/coder/v2/apiversion"
+
+// Version history:
+//
+// API v1.0:
+//   - Initial release
+//   - Ping
+//   - Sync operations: SyncStart, SyncWant, SyncComplete, SyncWait, SyncStatus
+
+const (
+	CurrentMajor = 1
+	CurrentMinor = 0
+)
+
+var CurrentVersion = apiversion.New(CurrentMajor, CurrentMinor)

agent/agentsocket/server.go

@@ -0,0 +1,185 @@
+package agentsocket
+
+import (
+	"context"
+	"errors"
+	"net"
+	"sync"
+
+	"golang.org/x/xerrors"
+
+	"github.com/hashicorp/yamux"
+	"storj.io/drpc/drpcmux"
+	"storj.io/drpc/drpcserver"
+
+	"cdr.dev/slog"
+	"github.com/coder/coder/v2/agent/agentsocket/proto"
+	"github.com/coder/coder/v2/agent/unit"
+	"github.com/coder/coder/v2/codersdk/drpcsdk"
+)
+
+// Server provides access to the DRPCAgentSocketService via a Unix domain socket.
+// Do not invoke Server{} directly. Use NewServer() instead.
+type Server struct {
+	logger     slog.Logger
+	path       string
+	drpcServer *drpcserver.Server
+	service    *DRPCAgentSocketService
+
+	mu       sync.Mutex
+	listener net.Listener
+	ctx      context.Context
+	cancel   context.CancelFunc
+	wg       sync.WaitGroup
+}
+
+func NewServer(path string, logger slog.Logger) (*Server, error) {
+	logger = logger.Named("agentsocket-server")
+	server := &Server{
+		logger: logger,
+		path:   path,
+		service: &DRPCAgentSocketService{
+			logger:      logger,
+			unitManager: unit.NewManager(),
+		},
+	}
+
+	mux := drpcmux.New()
+	err := proto.DRPCRegisterAgentSocket(mux, server.service)
+	if err != nil {
+		return nil, xerrors.Errorf("failed to register drpc service: %w", err)
+	}
+
+	server.drpcServer = drpcserver.NewWithOptions(mux, drpcserver.Options{
+		Manager: drpcsdk.DefaultDRPCOptions(nil),
+		Log: func(err error) {
+			if errors.Is(err, context.Canceled) ||
+				errors.Is(err, context.DeadlineExceeded) {
+				return
+			}
+			logger.Debug(context.Background(), "drpc server error", slog.Error(err))
+		},
+	})
+
+	if server.path == "" {
+		var err error
+		server.path, err = getDefaultSocketPath()
+		if err != nil {
+			return nil, xerrors.Errorf("get default socket path: %w", err)
+		}
+	}
+
+	listener, err := createSocket(server.path)
+	if err != nil {
+		return nil, xerrors.Errorf("create socket: %w", err)
+	}
+
+	server.listener = listener
+
+	// This context is canceled by server.Close().
+	// canceling it will close all connections.
+	server.ctx, server.cancel = context.WithCancel(context.Background())
+
+	server.logger.Info(server.ctx, "agent socket server started", slog.F("path", server.path))
+
+	server.wg.Add(1)
+	go func() {
+		defer server.wg.Done()
+		server.acceptConnections()
+	}()
+
+	return server, nil
+}
+
+func (s *Server) Close() error {
+	s.mu.Lock()
+
+	if s.listener == nil {
+		s.mu.Unlock()
+		return nil
+	}
+
+	s.logger.Info(s.ctx, "stopping agent socket server")
+
+	s.cancel()
+
+	if err := s.listener.Close(); err != nil {
+		s.logger.Warn(s.ctx, "error closing socket listener", slog.Error(err))
+	}
+
+	s.listener = nil
+
+	s.mu.Unlock()
+
+	// Wait for all connections to finish
+	s.wg.Wait()
+
+	if err := cleanupSocket(s.path); err != nil {
+		s.logger.Warn(s.ctx, "error cleaning up socket file", slog.Error(err))
+	}
+
+	s.logger.Info(s.ctx, "agent socket server stopped")
+
+	return nil
+}
+
+func (s *Server) acceptConnections() {
+	// In an edge case, Close() might race with acceptConnections() and set s.listener to nil.
+	// Therefore, we grab a copy of the listener under a lock. We might still get a nil listener,
+	// but then we know close has already run and we can return early.
+	s.mu.Lock()
+	listener := s.listener
+	s.mu.Unlock()
+	if listener == nil {
+		return
+	}
+
+	for {
+		select {
+		case <-s.ctx.Done():
+			return
+		default:
+		}
+
+		conn, err := listener.Accept()
+		if err != nil {
+			s.logger.Warn(s.ctx, "error accepting connection", slog.Error(err))
+			continue
+		}
+
+		s.mu.Lock()
+		if s.listener == nil {
+			s.mu.Unlock()
+			_ = conn.Close()
+			return
+		}
+		s.wg.Add(1)
+		s.mu.Unlock()
+
+		go func() {
+			defer s.wg.Done()
+			s.handleConnection(conn)
+		}()
+	}
+}
+
+func (s *Server) handleConnection(conn net.Conn) {
+	defer conn.Close()
+
+	s.logger.Debug(s.ctx, "new connection accepted", slog.F("remote_addr", conn.RemoteAddr()))
+
+	config := yamux.DefaultConfig()
+	config.LogOutput = nil
+	config.Logger = slog.Stdlib(s.ctx, s.logger.Named("agentsocket-yamux"), slog.LevelInfo)
+	session, err := yamux.Server(conn, config)
+	if err != nil {
+		s.logger.Warn(s.ctx, "failed to create yamux session", slog.Error(err))
+		return
+	}
+	defer session.Close()
+
+	err = s.drpcServer.Serve(s.ctx, session)
+	if err != nil {
+		s.logger.Debug(s.ctx, "drpc server finished", slog.Error(err))
+	}
+}

agent/agentsocket/server_test.go

@@ -0,0 +1,52 @@
+package agentsocket_test
+
+import (
+	"path/filepath"
+	"runtime"
+	"testing"
+
+	"github.com/stretchr/testify/require"
+
+	"cdr.dev/slog"
+	"github.com/coder/coder/v2/agent/agentsocket"
+)
+
+func TestServer(t *testing.T) {
+	t.Parallel()
+
+	if runtime.GOOS == "windows" {
+		t.Skip("agentsocket is not supported on Windows")
+	}
+
+	t.Run("StartStop", func(t *testing.T) {
+		t.Parallel()
+
+		socketPath := filepath.Join(t.TempDir(), "test.sock")
+		logger := slog.Make().Leveled(slog.LevelDebug)
+		server, err := agentsocket.NewServer(socketPath, logger)
+		require.NoError(t, err)
+		require.NoError(t, server.Close())
+	})
+
+	t.Run("AlreadyStarted", func(t *testing.T) {
+		t.Parallel()
+
+		socketPath := filepath.Join(t.TempDir(), "test.sock")
+		logger := slog.Make().Leveled(slog.LevelDebug)
+		server1, err := agentsocket.NewServer(socketPath, logger)
+		require.NoError(t, err)
+		defer server1.Close()
+		_, err = agentsocket.NewServer(socketPath, logger)
+		require.ErrorContains(t, err, "create socket")
+	})
+
+	t.Run("AutoSocketPath", func(t *testing.T) {
+		t.Parallel()
+
+		socketPath := filepath.Join(t.TempDir(), "test.sock")
+		logger := slog.Make().Leveled(slog.LevelDebug)
+		server, err := agentsocket.NewServer(socketPath, logger)
+		require.NoError(t, err)
+		require.NoError(t, server.Close())
+	})
+}

agent/agentsocket/service.go

@@ -0,0 +1,142 @@
+package agentsocket
+
+import (
+	"context"
+	"errors"
+
+	"golang.org/x/xerrors"
+
+	"cdr.dev/slog"
+	"github.com/coder/coder/v2/agent/agentsocket/proto"
+	"github.com/coder/coder/v2/agent/unit"
+)
+
+var _ proto.DRPCAgentSocketServer = (*DRPCAgentSocketService)(nil)
+
+var ErrUnitManagerNotAvailable = xerrors.New("unit manager not available")
+
+type DRPCAgentSocketService struct {
+	unitManager *unit.Manager
+	logger      slog.Logger
+}
+
+func (*DRPCAgentSocketService) Ping(_ context.Context, _ *proto.PingRequest) (*proto.PingResponse, error) {
+	return &proto.PingResponse{}, nil
+}
+
+func (s *DRPCAgentSocketService) SyncStart(_ context.Context, req *proto.SyncStartRequest) (*proto.SyncStartResponse, error) {
+	if s.unitManager == nil {
+		return nil, xerrors.Errorf("SyncStart: %w", ErrUnitManagerNotAvailable)
+	}
+
+	unitID := unit.ID(req.Unit)
+
+	if err := s.unitManager.Register(unitID); err != nil {
+		if !errors.Is(err, unit.ErrUnitAlreadyRegistered) {
+			return nil, xerrors.Errorf("SyncStart: %w", err)
+		}
+	}
+
+	isReady, err := s.unitManager.IsReady(unitID)
+	if err != nil {
+		return nil, xerrors.Errorf("cannot check readiness: %w", err)
+	}
+	if !isReady {
+		return nil, xerrors.Errorf("cannot start unit %q: unit not ready", req.Unit)
+	}
+
+	err = s.unitManager.UpdateStatus(unitID, unit.StatusStarted)
+	if err != nil {
+		return nil, xerrors.Errorf("cannot start unit %q: %w", req.Unit, err)
+	}
+
+	return &proto.SyncStartResponse{}, nil
+}
+
+func (s *DRPCAgentSocketService) SyncWant(_ context.Context, req *proto.SyncWantRequest) (*proto.SyncWantResponse, error) {
+	if s.unitManager == nil {
+		return nil, xerrors.Errorf("cannot add dependency: %w", ErrUnitManagerNotAvailable)
+	}
+
+	unitID := unit.ID(req.Unit)
+	dependsOnID := unit.ID(req.DependsOn)
+
+	if err := s.unitManager.Register(unitID); err != nil && !errors.Is(err, unit.ErrUnitAlreadyRegistered) {
+		return nil, xerrors.Errorf("cannot add dependency: %w", err)
+	}
+
+	if err := s.unitManager.AddDependency(unitID, dependsOnID, unit.StatusComplete); err != nil {
+		return nil, xerrors.Errorf("cannot add dependency: %w", err)
+	}
+
+	return &proto.SyncWantResponse{}, nil
+}
+
+func (s *DRPCAgentSocketService) SyncComplete(_ context.Context, req *proto.SyncCompleteRequest) (*proto.SyncCompleteResponse, error) {
+	if s.unitManager == nil {
+		return nil, xerrors.Errorf("cannot complete unit: %w", ErrUnitManagerNotAvailable)
+	}
+
+	unitID := unit.ID(req.Unit)
+
+	if err := s.unitManager.UpdateStatus(unitID, unit.StatusComplete); err != nil {
+		return nil, xerrors.Errorf("cannot complete unit %q: %w", req.Unit, err)
+	}
+
+	return &proto.SyncCompleteResponse{}, nil
+}
+
+func (s *DRPCAgentSocketService) SyncReady(_ context.Context, req *proto.SyncReadyRequest) (*proto.SyncReadyResponse, error) {
+	if s.unitManager == nil {
+		return nil, xerrors.Errorf("cannot check readiness: %w", ErrUnitManagerNotAvailable)
+	}
+
+	unitID := unit.ID(req.Unit)
+	isReady, err := s.unitManager.IsReady(unitID)
+	if err != nil {
+		return nil, xerrors.Errorf("cannot check readiness: %w", err)
+	}
+
+	return &proto.SyncReadyResponse{
+		Ready: isReady,
+	}, nil
+}
+
+func (s *DRPCAgentSocketService) SyncStatus(_ context.Context, req *proto.SyncStatusRequest) (*proto.SyncStatusResponse, error) {
+	if s.unitManager == nil {
+		return nil, xerrors.Errorf("cannot get status for unit %q: %w", req.Unit, ErrUnitManagerNotAvailable)
+	}
+
+	unitID := unit.ID(req.Unit)
+
+	isReady, err := s.unitManager.IsReady(unitID)
+	if err != nil {
+		return nil, xerrors.Errorf("cannot check readiness: %w", err)
+	}
+
+	dependencies, err := s.unitManager.GetAllDependencies(unitID)
+	if err != nil {
+		return nil, xerrors.Errorf("failed to get dependencies: %w", err)
+	}
+
+	var depInfos []*proto.DependencyInfo
+	for _, dep := range dependencies {
+		depInfos = append(depInfos, &proto.DependencyInfo{
+			Unit:           string(dep.Unit),
+			DependsOn:      string(dep.DependsOn),
+			RequiredStatus: string(dep.RequiredStatus),
+			CurrentStatus:  string(dep.CurrentStatus),
+			IsSatisfied:    dep.IsSatisfied,
+		})
+	}
+
+	u, err := s.unitManager.Unit(unitID)
+	if err != nil {
+		return nil, xerrors.Errorf("cannot get status for unit %q: %w", req.Unit, err)
+	}
+	return &proto.SyncStatusResponse{
+		Status:       string(u.Status()),
+		IsReady:      isReady,
+		Dependencies: depInfos,
+	}, nil
+}

agent/agentsocket/service_test.go

@@ -0,0 +1,470 @@
+package agentsocket_test
+
+import (
+	"context"
+	"crypto/sha256"
+	"encoding/hex"
+	"fmt"
+	"net"
+	"os"
+	"path/filepath"
+	"runtime"
+	"testing"
+
+	"github.com/hashicorp/yamux"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	"cdr.dev/slog"
+	"github.com/coder/coder/v2/agent/agentsocket"
+	"github.com/coder/coder/v2/agent/agentsocket/proto"
+	"github.com/coder/coder/v2/agent/unit"
+	"github.com/coder/coder/v2/codersdk/drpcsdk"
+)
+
+// tempDirUnixSocket returns a temporary directory that can safely hold unix
+// sockets (probably).
+//
+// During tests on darwin we hit the max path length limit for unix sockets
+// pretty easily in the default location, so this function uses /tmp instead to
+// get shorter paths. To keep paths short, we use a hash of the test name
+// instead of the full test name.
+func tempDirUnixSocket(t *testing.T) string {
+	t.Helper()
+	if runtime.GOOS == "darwin" {
+		// Use a short hash of the test name to keep the path under 104 chars
+		hash := sha256.Sum256([]byte(t.Name()))
+		hashStr := hex.EncodeToString(hash[:])[:8] // Use first 8 chars of hash
+		dir, err := os.MkdirTemp("/tmp", fmt.Sprintf("c-%s-", hashStr))
+		require.NoError(t, err, "create temp dir for unix socket test")
+		t.Cleanup(func() {
+			err := os.RemoveAll(dir)
+			assert.NoError(t, err, "remove temp dir", dir)
+		})
+		return dir
+	}
+	return t.TempDir()
+}
+
+// newSocketClient creates a DRPC client connected to the Unix socket at the given path.
+func newSocketClient(t *testing.T, socketPath string) proto.DRPCAgentSocketClient {
+	t.Helper()
+
+	conn, err := net.Dial("unix", socketPath)
+	require.NoError(t, err)
+
+	config := yamux.DefaultConfig()
+	config.Logger = nil
+	session, err := yamux.Client(conn, config)
+	require.NoError(t, err)
+
+	client := proto.NewDRPCAgentSocketClient(drpcsdk.MultiplexedConn(session))
+
+	t.Cleanup(func() {
+		_ = session.Close()
+		_ = conn.Close()
+	})
+	return client
+}
+
+func TestDRPCAgentSocketService(t *testing.T) {
+	t.Parallel()
+
+	if runtime.GOOS == "windows" {
+		t.Skip("agentsocket is not supported on Windows")
+	}
+
+	t.Run("Ping", func(t *testing.T) {
+		t.Parallel()
+
+		socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+
+		server, err := agentsocket.NewServer(
+			socketPath,
+			slog.Make().Leveled(slog.LevelDebug),
+		)
+		require.NoError(t, err)
+		defer server.Close()
+
+		client := newSocketClient(t, socketPath)
+
+		_, err = client.Ping(context.Background(), &proto.PingRequest{})
+		require.NoError(t, err)
+	})
+
+	t.Run("SyncStart", func(t *testing.T) {
+		t.Parallel()
+
+		t.Run("NewUnit", func(t *testing.T) {
+			t.Parallel()
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+
+			server, err := agentsocket.NewServer(
+				socketPath,
+				slog.Make().Leveled(slog.LevelDebug),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(t, socketPath)
+
+			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+
+			status, err := client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+			require.Equal(t, "started", status.Status)
+		})
+
+		t.Run("UnitAlreadyStarted", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+
+			server, err := agentsocket.NewServer(
+				socketPath,
+				slog.Make().Leveled(slog.LevelDebug),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(t, socketPath)
+
+			// First Start
+			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+			status, err := client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+			require.Equal(t, "started", status.Status)
+
+			// Second Start
+			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
+				Unit: "test-unit",
+			})
+			require.ErrorContains(t, err, unit.ErrSameStatusAlreadySet.Error())
+
+			status, err = client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+			require.Equal(t, "started", status.Status)
+		})
+
+		t.Run("UnitAlreadyCompleted", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+
+			server, err := agentsocket.NewServer(
+				socketPath,
+				slog.Make().Leveled(slog.LevelDebug),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(t, socketPath)
+
+			// First start
+			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+
+			status, err := client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+			require.Equal(t, "started", status.Status)
+
+			// Complete the unit
+			_, err = client.SyncComplete(context.Background(), &proto.SyncCompleteRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+
+			status, err = client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+			require.Equal(t, "completed", status.Status)
+
+			// Second start
+			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+
+			status, err = client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+			require.Equal(t, "started", status.Status)
+		})
+
+		t.Run("UnitNotReady", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+
+			server, err := agentsocket.NewServer(
+				socketPath,
+				slog.Make().Leveled(slog.LevelDebug),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(t, socketPath)
+
+			_, err = client.SyncWant(context.Background(), &proto.SyncWantRequest{
+				Unit:      "test-unit",
+				DependsOn: "dependency-unit",
+			})
+			require.NoError(t, err)
+
+			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
+				Unit: "test-unit",
+			})
+			require.ErrorContains(t, err, "unit not ready")
+
+			status, err := client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+			require.Equal(t, string(unit.StatusPending), status.Status)
+			require.False(t, status.IsReady)
+		})
+	})
+
+	t.Run("SyncWant", func(t *testing.T) {
+		t.Parallel()
+
+		t.Run("NewUnits", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+
+			server, err := agentsocket.NewServer(
+				socketPath,
+				slog.Make().Leveled(slog.LevelDebug),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(t, socketPath)
+
+			// If dependency units are not registered, they are registered automatically
+			_, err = client.SyncWant(context.Background(), &proto.SyncWantRequest{
+				Unit:      "test-unit",
+				DependsOn: "dependency-unit",
+			})
+			require.NoError(t, err)
+
+			status, err := client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+			require.Len(t, status.Dependencies, 1)
+			require.Equal(t, "dependency-unit", status.Dependencies[0].DependsOn)
+			require.Equal(t, "completed", status.Dependencies[0].RequiredStatus)
+		})
+
+		t.Run("DependencyAlreadyRegistered", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+
+			server, err := agentsocket.NewServer(
+				socketPath,
+				slog.Make().Leveled(slog.LevelDebug),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(t, socketPath)
+
+			// Start the dependency unit
+			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
+				Unit: "dependency-unit",
+			})
+			require.NoError(t, err)
+
+			status, err := client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
+				Unit: "dependency-unit",
+			})
+			require.NoError(t, err)
+			require.Equal(t, "started", status.Status)
+
+			// Add the dependency after the dependency unit has already started
+			_, err = client.SyncWant(context.Background(), &proto.SyncWantRequest{
+				Unit:      "test-unit",
+				DependsOn: "dependency-unit",
+			})
+
+			// Dependencies can be added even if the dependency unit has already started
+			require.NoError(t, err)
+
+			// The dependency is now reflected in the test unit's status
+			status, err = client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+			require.Equal(t, "dependency-unit", status.Dependencies[0].DependsOn)
+			require.Equal(t, "completed", status.Dependencies[0].RequiredStatus)
+		})
+
+		t.Run("DependencyAddedAfterDependentStarted", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+
+			server, err := agentsocket.NewServer(
+				socketPath,
+				slog.Make().Leveled(slog.LevelDebug),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(t, socketPath)
+
+			// Start the dependent unit
+			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+
+			status, err := client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+			require.Equal(t, "started", status.Status)
+
+			// Add the dependency after the dependency unit has already started
+			_, err = client.SyncWant(context.Background(), &proto.SyncWantRequest{
+				Unit:      "test-unit",
+				DependsOn: "dependency-unit",
+			})
+
+			// Dependencies can be added even if the dependent unit has already started.
+			// The dependency applies the next time a unit is started. The current status is not updated.
+			// This is to allow flexible dependency management. It does mean that users of this API should
+			// take care to add dependencies before they start their dependent units.
+			require.NoError(t, err)
+
+			// The dependency is now reflected in the test unit's status
+			status, err = client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+			require.Equal(t, "dependency-unit", status.Dependencies[0].DependsOn)
+			require.Equal(t, "completed", status.Dependencies[0].RequiredStatus)
+		})
+	})
+
+	t.Run("SyncReady", func(t *testing.T) {
+		t.Parallel()
+
+		t.Run("UnregisteredUnit", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+
+			server, err := agentsocket.NewServer(
+				socketPath,
+				slog.Make().Leveled(slog.LevelDebug),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(t, socketPath)
+
+			response, err := client.SyncReady(context.Background(), &proto.SyncReadyRequest{
+				Unit: "unregistered-unit",
+			})
+			require.NoError(t, err)
+			require.False(t, response.Ready)
+		})
+
+		t.Run("UnitNotReady", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+
+			server, err := agentsocket.NewServer(
+				socketPath,
+				slog.Make().Leveled(slog.LevelDebug),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(t, socketPath)
+
+			// Register a unit with an unsatisfied dependency
+			_, err = client.SyncWant(context.Background(), &proto.SyncWantRequest{
+				Unit:      "test-unit",
+				DependsOn: "dependency-unit",
+			})
+			require.NoError(t, err)
+
+			// Check readiness - should be false because dependency is not satisfied
+			response, err := client.SyncReady(context.Background(), &proto.SyncReadyRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+			require.False(t, response.Ready)
+		})
+
+		t.Run("UnitReady", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+
+			server, err := agentsocket.NewServer(
+				socketPath,
+				slog.Make().Leveled(slog.LevelDebug),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(t, socketPath)
+
+			// Register a unit with no dependencies - should be ready immediately
+			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+
+			// Check readiness - should be true
+			_, err = client.SyncReady(context.Background(), &proto.SyncReadyRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+
+			// Also test a unit with satisfied dependencies
+			_, err = client.SyncWant(context.Background(), &proto.SyncWantRequest{
+				Unit:      "dependent-unit",
+				DependsOn: "test-unit",
+			})
+			require.NoError(t, err)
+
+			// Complete the dependency
+			_, err = client.SyncComplete(context.Background(), &proto.SyncCompleteRequest{
+				Unit: "test-unit",
+			})
+			require.NoError(t, err)
+
+			// Now dependent-unit should be ready
+			_, err = client.SyncReady(context.Background(), &proto.SyncReadyRequest{
+				Unit: "dependent-unit",
+			})
+			require.NoError(t, err)
+		})
+	})
+}

agent/agentsocket/socket_unix.go

@@ -0,0 +1,83 @@
+//go:build !windows
+
+package agentsocket
+
+import (
+	"crypto/rand"
+	"encoding/hex"
+	"net"
+	"os"
+	"path/filepath"
+	"time"
+
+	"golang.org/x/xerrors"
+)
+
+// createSocket creates a Unix domain socket listener
+func createSocket(path string) (net.Listener, error) {
+	if !isSocketAvailable(path) {
+		return nil, xerrors.Errorf("socket path %s is not available", path)
+	}
+
+	if err := os.Remove(path); err != nil && !os.IsNotExist(err) {
+		return nil, xerrors.Errorf("remove existing socket: %w", err)
+	}
+
+	// Create parent directory if it doesn't exist
+	parentDir := filepath.Dir(path)
+	if err := os.MkdirAll(parentDir, 0o700); err != nil {
+		return nil, xerrors.Errorf("create socket directory: %w", err)
+	}
+
+	listener, err := net.Listen("unix", path)
+	if err != nil {
+		return nil, xerrors.Errorf("listen on unix socket: %w", err)
+	}
+
+	if err := os.Chmod(path, 0o600); err != nil {
+		_ = listener.Close()
+		return nil, xerrors.Errorf("set socket permissions: %w", err)
+	}
+	return listener, nil
+}
+
+// getDefaultSocketPath returns the default socket path for Unix-like systems
+func getDefaultSocketPath() (string, error) {
+	randomBytes := make([]byte, 4)
+	if _, err := rand.Read(randomBytes); err != nil {
+		return "", xerrors.Errorf("generate random socket name: %w", err)
+	}
+	randomSuffix := hex.EncodeToString(randomBytes)
+
+	// Try XDG_RUNTIME_DIR first
+	if runtimeDir := os.Getenv("XDG_RUNTIME_DIR"); runtimeDir != "" {
+		return filepath.Join(runtimeDir, "coder-agent-"+randomSuffix+".sock"), nil
+	}
+
+	return filepath.Join("/tmp", "coder-agent-"+randomSuffix+".sock"), nil
+}
+
+// CleanupSocket removes the socket file
+func cleanupSocket(path string) error {
+	return os.Remove(path)
+}
+
+// isSocketAvailable checks if a socket path is available for use
+func isSocketAvailable(path string) bool {
+	// Check if file exists
+	if _, err := os.Stat(path); os.IsNotExist(err) {
+		return true
+	}
+
+	// Try to connect to see if it's actually listening
+	dialer := net.Dialer{Timeout: 10 * time.Second}
+	conn, err := dialer.Dial("unix", path)
+	if err != nil {
+		// If we can't connect, the socket is not in use
+		// Socket is available for use
+		return true
+	}
+	_ = conn.Close()
+	// Socket is in use
+	return false
+}

agent/agentsocket/socket_windows.go

@@ -0,0 +1,27 @@
+//go:build windows
+
+package agentsocket
+
+import (
+	"net"
+
+	"golang.org/x/xerrors"
+)
+
+// createSocket returns an error indicating that agentsocket is not supported on Windows.
+// This feature is unix-only in its current experimental state.
+func createSocket(_ string) (net.Listener, error) {
+	return nil, xerrors.New("agentsocket is not supported on Windows")
+}
+
+// getDefaultSocketPath returns an error indicating that agentsocket is not supported on Windows.
+// This feature is unix-only in its current experimental state.
+func getDefaultSocketPath() (string, error) {
+	return "", xerrors.New("agentsocket is not supported on Windows")
+}
+
+// cleanupSocket is a no-op on Windows since agentsocket is not supported.
+func cleanupSocket(_ string) error {
+	// No-op since agentsocket is not supported on Windows
+	return nil
+}

agent/files.go

@@ -250,7 +250,9 @@ func (a *agent) editFile(ctx context.Context, path string, edits []workspacesdk.
 		transforms[i] = replace.String(edit.Search, edit.Replace)
 	}
 
-	tmpfile, err := afero.TempFile(a.filesystem, "", filepath.Base(path))
+	// Create an adjacent file to ensure it will be on the same device and can be
+	// moved atomically.
+	tmpfile, err := afero.TempFile(a.filesystem, filepath.Dir(path), filepath.Base(path))
 	if err != nil {
 		return http.StatusInternalServerError, err
 	}

agent/unit/graph.go

@@ -58,7 +58,7 @@ func (g *Graph[EdgeType, VertexType]) AddEdge(from, to VertexType, edge EdgeType
 	toID := g.getOrCreateVertexID(to)
 
 	if g.canReach(to, from) {
-		return xerrors.Errorf("adding edge (%v -> %v) would create a cycle", from, to)
+		return xerrors.Errorf("adding edge (%v -> %v): %w", from, to, ErrCycleDetected)
 	}
 
 	g.gonumGraph.SetEdge(simple.Edge{F: simple.Node(fromID), T: simple.Node(toID)})

agent/unit/graph_test.go

@@ -148,8 +148,7 @@ func TestGraph(t *testing.T) {
 			graph := &testGraph{}
 			unit1 := &testGraphVertex{Name: "unit1"}
 			err := graph.AddEdge(unit1, unit1, testEdgeCompleted)
-			require.Error(t, err)
-			require.ErrorContains(t, err, fmt.Sprintf("adding edge (%v -> %v) would create a cycle", unit1, unit1))
+			require.ErrorIs(t, err, unit.ErrCycleDetected)
 
 			return graph
 		},
@@ -160,8 +159,7 @@ func TestGraph(t *testing.T) {
 			err := graph.AddEdge(unit1, unit2, testEdgeCompleted)
 			require.NoError(t, err)
 			err = graph.AddEdge(unit2, unit1, testEdgeStarted)
-			require.Error(t, err)
-			require.ErrorContains(t, err, fmt.Sprintf("adding edge (%v -> %v) would create a cycle", unit2, unit1))
+			require.ErrorIs(t, err, unit.ErrCycleDetected)
 
 			return graph
 		},
@@ -341,7 +339,7 @@ func TestGraphThreadSafety(t *testing.T) {
 		// Verify all attempts correctly returned cycle error
 		for i, err := range cycleErrors {
 			require.Error(t, err, "goroutine %d should have detected cycle", i)
-			require.Contains(t, err.Error(), "would create a cycle")
+			require.ErrorIs(t, err, unit.ErrCycleDetected)
 		}
 
 		// Verify graph remains valid (original chain intact)

agent/unit/manager.go

@@ -0,0 +1,280 @@
+package unit
+
+import (
+	"errors"
+	"sync"
+
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/coderd/util/slice"
+)
+
+var (
+	ErrUnitIDRequired           = xerrors.New("unit name is required")
+	ErrUnitNotFound             = xerrors.New("unit not found")
+	ErrUnitAlreadyRegistered    = xerrors.New("unit already registered")
+	ErrCannotUpdateOtherUnit    = xerrors.New("cannot update other unit's status")
+	ErrDependenciesNotSatisfied = xerrors.New("unit dependencies not satisfied")
+	ErrSameStatusAlreadySet     = xerrors.New("same status already set")
+	ErrCycleDetected            = xerrors.New("cycle detected")
+	ErrFailedToAddDependency    = xerrors.New("failed to add dependency")
+)
+
+// Status represents the status of a unit.
+type Status string
+
+// Status constants for dependency tracking.
+const (
+	StatusNotRegistered Status = ""
+	StatusPending       Status = "pending"
+	StatusStarted       Status = "started"
+	StatusComplete      Status = "completed"
+)
+
+// ID provides a type narrowed representation of the unique identifier of a unit.
+type ID string
+
+// Unit represents a point-in-time snapshot of a vertex in the dependency graph.
+// Units may depend on other units, or be depended on by other units. The unit struct
+// is not aware of updates made to the dependency graph after it is initialized and should
+// not be cached.
+type Unit struct {
+	id     ID
+	status Status
+	// ready is true if all dependencies are satisfied.
+	// It does not have an accessor method on Unit, because a unit cannot know whether it is ready.
+	// Only the Manager can calculate whether a unit is ready based on knowledge of the dependency graph.
+	// To discourage use of an outdated readiness value, only the Manager should set and return this field.
+	ready bool
+}
+
+func (u Unit) ID() ID {
+	return u.id
+}
+
+func (u Unit) Status() Status {
+	return u.status
+}
+
+// Dependency represents a dependency relationship between units.
+type Dependency struct {
+	Unit           ID
+	DependsOn      ID
+	RequiredStatus Status
+	CurrentStatus  Status
+	IsSatisfied    bool
+}
+
+// Manager provides reactive dependency tracking over a Graph.
+// It manages Unit registration, dependency relationships, and status updates
+// with automatic recalculation of readiness when dependencies are satisfied.
+type Manager struct {
+	mu sync.RWMutex
+
+	// The underlying graph that stores dependency relationships
+	graph *Graph[Status, ID]
+
+	// Store vertex instances for each unit to ensure consistent references
+	units map[ID]Unit
+}
+
+// NewManager creates a new Manager instance.
+func NewManager() *Manager {
+	return &Manager{
+		graph: &Graph[Status, ID]{},
+		units: make(map[ID]Unit),
+	}
+}
+
+// Register adds a unit to the manager if it is not already registered.
+// If a Unit is already registered (per the ID field), it is not updated.
+func (m *Manager) Register(id ID) error {
+	m.mu.Lock()
+	defer m.mu.Unlock()
+
+	if id == "" {
+		return xerrors.Errorf("registering unit %q: %w", id, ErrUnitIDRequired)
+	}
+
+	if m.registered(id) {
+		return xerrors.Errorf("registering unit %q: %w", id, ErrUnitAlreadyRegistered)
+	}
+
+	m.units[id] = Unit{
+		id:     id,
+		status: StatusPending,
+		ready:  true,
+	}
+
+	return nil
+}
+
+// registered checks if a unit is registered in the manager.
+func (m *Manager) registered(id ID) bool {
+	return m.units[id].status != StatusNotRegistered
+}
+
+// Unit fetches a unit from the manager. If the unit does not exist,
+// it returns the Unit zero-value as a placeholder unit, because
+// units may depend on other units that have not yet been created.
+func (m *Manager) Unit(id ID) (Unit, error) {
+	if id == "" {
+		return Unit{}, xerrors.Errorf("unit ID cannot be empty: %w", ErrUnitIDRequired)
+	}
+
+	m.mu.RLock()
+	defer m.mu.RUnlock()
+
+	return m.units[id], nil
+}
+
+func (m *Manager) IsReady(id ID) (bool, error) {
+	if id == "" {
+		return false, xerrors.Errorf("unit ID cannot be empty: %w", ErrUnitIDRequired)
+	}
+
+	m.mu.RLock()
+	defer m.mu.RUnlock()
+
+	if !m.registered(id) {
+		return false, nil
+	}
+
+	return m.units[id].ready, nil
+}
+
+// AddDependency adds a dependency relationship between units.
+// The unit depends on the dependsOn unit reaching the requiredStatus.
+func (m *Manager) AddDependency(unit ID, dependsOn ID, requiredStatus Status) error {
+	m.mu.Lock()
+	defer m.mu.Unlock()
+
+	switch {
+	case unit == "":
+		return xerrors.Errorf("dependent name cannot be empty: %w", ErrUnitIDRequired)
+	case dependsOn == "":
+		return xerrors.Errorf("dependency name cannot be empty: %w", ErrUnitIDRequired)
+	case !m.registered(unit):
+		return xerrors.Errorf("dependent unit %q must be registered first: %w", unit, ErrUnitNotFound)
+	}
+
+	// Add the dependency edge to the graph
+	// The edge goes from unit to dependsOn, representing the dependency
+	err := m.graph.AddEdge(unit, dependsOn, requiredStatus)
+	if err != nil {
+		return xerrors.Errorf("adding edge for unit %q: %w", unit, errors.Join(ErrFailedToAddDependency, err))
+	}
+
+	// Recalculate readiness for the unit since it now has a new dependency
+	m.recalculateReadinessUnsafe(unit)
+
+	return nil
+}
+
+// UpdateStatus updates a unit's status and recalculates readiness for affected dependents.
+func (m *Manager) UpdateStatus(unit ID, newStatus Status) error {
+	m.mu.Lock()
+	defer m.mu.Unlock()
+
+	switch {
+	case unit == "":
+		return xerrors.Errorf("updating status for unit %q: %w", unit, ErrUnitIDRequired)
+	case !m.registered(unit):
+		return xerrors.Errorf("unit %q must be registered first: %w", unit, ErrUnitNotFound)
+	}
+
+	u := m.units[unit]
+	if u.status == newStatus {
+		return xerrors.Errorf("checking status for unit %q: %w", unit, ErrSameStatusAlreadySet)
+	}
+
+	u.status = newStatus
+	m.units[unit] = u
+
+	// Get all units that depend on this one (reverse adjacent vertices)
+	dependents := m.graph.GetReverseAdjacentVertices(unit)
+
+	// Recalculate readiness for all dependents
+	for _, dependent := range dependents {
+		m.recalculateReadinessUnsafe(dependent.From)
+	}
+
+	return nil
+}
+
+// recalculateReadinessUnsafe recalculates the readiness state for a unit.
+// This method assumes the caller holds the write lock.
+func (m *Manager) recalculateReadinessUnsafe(unit ID) {
+	u := m.units[unit]
+	dependencies := m.graph.GetForwardAdjacentVertices(unit)
+
+	allSatisfied := true
+	for _, dependency := range dependencies {
+		requiredStatus := dependency.Edge
+		dependsOnUnit := m.units[dependency.To]
+		if dependsOnUnit.status != requiredStatus {
+			allSatisfied = false
+			break
+		}
+	}
+
+	u.ready = allSatisfied
+	m.units[unit] = u
+}
+
+// GetGraph returns the underlying graph for visualization and debugging.
+// This should be used carefully as it exposes the internal graph structure.
+func (m *Manager) GetGraph() *Graph[Status, ID] {
+	return m.graph
+}
+
+// GetAllDependencies returns all dependencies for a unit, both satisfied and unsatisfied.
+func (m *Manager) GetAllDependencies(unit ID) ([]Dependency, error) {
+	m.mu.RLock()
+	defer m.mu.RUnlock()
+
+	if unit == "" {
+		return nil, xerrors.Errorf("unit ID cannot be empty: %w", ErrUnitIDRequired)
+	}
+
+	if !m.registered(unit) {
+		return nil, xerrors.Errorf("checking registration for unit %q: %w", unit, ErrUnitNotFound)
+	}
+
+	dependencies := m.graph.GetForwardAdjacentVertices(unit)
+
+	var allDependencies []Dependency
+
+	for _, dependency := range dependencies {
+		dependsOnUnit := m.units[dependency.To]
+		requiredStatus := dependency.Edge
+		allDependencies = append(allDependencies, Dependency{
+			Unit:           unit,
+			DependsOn:      dependency.To,
+			RequiredStatus: requiredStatus,
+			CurrentStatus:  dependsOnUnit.status,
+			IsSatisfied:    dependsOnUnit.status == requiredStatus,
+		})
+	}
+
+	return allDependencies, nil
+}
+
+// GetUnmetDependencies returns a list of unsatisfied dependencies for a unit.
+func (m *Manager) GetUnmetDependencies(unit ID) ([]Dependency, error) {
+	allDependencies, err := m.GetAllDependencies(unit)
+	if err != nil {
+		return nil, err
+	}
+
+	var unmetDependencies []Dependency = slice.Filter(allDependencies, func(dependency Dependency) bool {
+		return !dependency.IsSatisfied
+	})
+
+	return unmetDependencies, nil
+}
+
+// ExportDOT exports the dependency graph to DOT format for visualization.
+func (m *Manager) ExportDOT(name string) (string, error) {
+	return m.graph.ToDOT(name)
+}

agent/unit/manager_test.go

@@ -0,0 +1,743 @@
+package unit_test
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/agent/unit"
+)
+
+const (
+	unitA unit.ID = "serviceA"
+	unitB unit.ID = "serviceB"
+	unitC unit.ID = "serviceC"
+	unitD unit.ID = "serviceD"
+)
+
+func TestManager_UnitValidation(t *testing.T) {
+	t.Parallel()
+
+	t.Run("Empty Unit Name", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		err := manager.Register("")
+		require.ErrorIs(t, err, unit.ErrUnitIDRequired)
+		err = manager.AddDependency("", unitA, unit.StatusStarted)
+		require.ErrorIs(t, err, unit.ErrUnitIDRequired)
+		err = manager.AddDependency(unitA, "", unit.StatusStarted)
+		require.ErrorIs(t, err, unit.ErrUnitIDRequired)
+		dependencies, err := manager.GetAllDependencies("")
+		require.ErrorIs(t, err, unit.ErrUnitIDRequired)
+		require.Len(t, dependencies, 0)
+		unmetDependencies, err := manager.GetUnmetDependencies("")
+		require.ErrorIs(t, err, unit.ErrUnitIDRequired)
+		require.Len(t, unmetDependencies, 0)
+		err = manager.UpdateStatus("", unit.StatusStarted)
+		require.ErrorIs(t, err, unit.ErrUnitIDRequired)
+		isReady, err := manager.IsReady("")
+		require.ErrorIs(t, err, unit.ErrUnitIDRequired)
+		require.False(t, isReady)
+		u, err := manager.Unit("")
+		require.ErrorIs(t, err, unit.ErrUnitIDRequired)
+		assert.Equal(t, unit.Unit{}, u)
+	})
+}
+
+func TestManager_Register(t *testing.T) {
+	t.Parallel()
+
+	t.Run("RegisterNewUnit", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Given: a unit is registered
+		err := manager.Register(unitA)
+		require.NoError(t, err)
+
+		// Then: the unit should be ready (no dependencies)
+		u, err := manager.Unit(unitA)
+		require.NoError(t, err)
+		assert.Equal(t, unitA, u.ID())
+		assert.Equal(t, unit.StatusPending, u.Status())
+		isReady, err := manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.True(t, isReady)
+	})
+
+	t.Run("RegisterDuplicateUnit", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Given: a unit is registered
+		err := manager.Register(unitA)
+		require.NoError(t, err)
+
+		// Newly registered units have StatusPending. We update the unit status to StatusStarted,
+		// so we can later assert that it is not overwritten back to StatusPending by the second
+		// register call
+		manager.UpdateStatus(unitA, unit.StatusStarted)
+
+		// When: the unit is registered again
+		err = manager.Register(unitA)
+
+		// Then: a descriptive error should be returned
+		require.ErrorIs(t, err, unit.ErrUnitAlreadyRegistered)
+
+		// Then: the unit status should not be overwritten
+		u, err := manager.Unit(unitA)
+		require.NoError(t, err)
+		assert.Equal(t, unit.StatusStarted, u.Status())
+		isReady, err := manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.True(t, isReady)
+	})
+
+	t.Run("RegisterMultipleUnits", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Given: multiple units are registered
+		unitIDs := []unit.ID{unitA, unitB, unitC}
+		for _, unit := range unitIDs {
+			err := manager.Register(unit)
+			require.NoError(t, err)
+		}
+
+		// Then: all units should be ready initially
+		for _, unitID := range unitIDs {
+			u, err := manager.Unit(unitID)
+			require.NoError(t, err)
+			assert.Equal(t, unit.StatusPending, u.Status())
+			isReady, err := manager.IsReady(unitID)
+			require.NoError(t, err)
+			assert.True(t, isReady)
+		}
+	})
+}
+
+func TestManager_AddDependency(t *testing.T) {
+	t.Parallel()
+
+	t.Run("AddDependencyBetweenRegisteredUnits", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Given: units A and B are registered
+		err := manager.Register(unitA)
+		require.NoError(t, err)
+		err = manager.Register(unitB)
+		require.NoError(t, err)
+
+		// Given: Unit A depends on Unit B being unit.StatusStarted
+		err = manager.AddDependency(unitA, unitB, unit.StatusStarted)
+		require.NoError(t, err)
+
+		// Then: Unit A should not be ready (depends on B)
+		u, err := manager.Unit(unitA)
+		require.NoError(t, err)
+		assert.Equal(t, unit.StatusPending, u.Status())
+		isReady, err := manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.False(t, isReady)
+
+		// Then: Unit B should still be ready (no dependencies)
+		u, err = manager.Unit(unitB)
+		require.NoError(t, err)
+		assert.Equal(t, unit.StatusPending, u.Status())
+		isReady, err = manager.IsReady(unitB)
+		require.NoError(t, err)
+		assert.True(t, isReady)
+
+		// When: Unit B is started
+		err = manager.UpdateStatus(unitB, unit.StatusStarted)
+		require.NoError(t, err)
+
+		// Then: Unit A should be ready, because its dependency is now in the desired state.
+		isReady, err = manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.True(t, isReady)
+
+		// When: Unit B is stopped
+		err = manager.UpdateStatus(unitB, unit.StatusPending)
+		require.NoError(t, err)
+
+		// Then: Unit A should no longer be ready, because its dependency is not in the desired state.
+		isReady, err = manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.False(t, isReady)
+	})
+
+	t.Run("AddDependencyByAnUnregisteredDependentUnit", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Given Unit B is registered
+		err := manager.Register(unitB)
+		require.NoError(t, err)
+
+		// Given Unit A depends on Unit B being started
+		err = manager.AddDependency(unitA, unitB, unit.StatusStarted)
+
+		// Then: a descriptive error communicates that the dependency cannot be added
+		// because the dependent unit must be registered first.
+		require.ErrorIs(t, err, unit.ErrUnitNotFound)
+	})
+
+	t.Run("AddDependencyOnAnUnregisteredUnit", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Given unit A is registered
+		err := manager.Register(unitA)
+		require.NoError(t, err)
+
+		// Given Unit B is not yet registered
+		// And Unit A depends on Unit B being started
+		err = manager.AddDependency(unitA, unitB, unit.StatusStarted)
+		require.NoError(t, err)
+
+		// Then: The dependency should be visible in Unit A's status
+		dependencies, err := manager.GetAllDependencies(unitA)
+		require.NoError(t, err)
+		require.Len(t, dependencies, 1)
+		assert.Equal(t, unitB, dependencies[0].DependsOn)
+		assert.Equal(t, unit.StatusStarted, dependencies[0].RequiredStatus)
+		assert.False(t, dependencies[0].IsSatisfied)
+
+		u, err := manager.Unit(unitB)
+		require.NoError(t, err)
+		assert.Equal(t, unit.StatusNotRegistered, u.Status())
+
+		// Then: Unit A should not be ready, because it depends on Unit B
+		isReady, err := manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.False(t, isReady)
+
+		// When: Unit B is registered
+		err = manager.Register(unitB)
+		require.NoError(t, err)
+
+		// Then: Unit A should still not be ready.
+		// Unit B is not registered, but it has not been started as required by the dependency.
+		isReady, err = manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.False(t, isReady)
+
+		// When: Unit B is started
+		err = manager.UpdateStatus(unitB, unit.StatusStarted)
+		require.NoError(t, err)
+
+		// Then: Unit A should be ready, because its dependency is now in the desired state.
+		isReady, err = manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.True(t, isReady)
+	})
+
+	t.Run("AddDependencyCreatesACyclicDependency", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Register units
+		err := manager.Register(unitA)
+		require.NoError(t, err)
+		err = manager.Register(unitB)
+		require.NoError(t, err)
+		err = manager.Register(unitC)
+		require.NoError(t, err)
+		err = manager.Register(unitD)
+		require.NoError(t, err)
+
+		// A depends on B
+		err = manager.AddDependency(unitA, unitB, unit.StatusStarted)
+		require.NoError(t, err)
+		// B depends on C
+		err = manager.AddDependency(unitB, unitC, unit.StatusStarted)
+		require.NoError(t, err)
+
+		// C depends on D
+		err = manager.AddDependency(unitC, unitD, unit.StatusStarted)
+		require.NoError(t, err)
+
+		// Try to make D depend on A (creates indirect cycle)
+		err = manager.AddDependency(unitD, unitA, unit.StatusStarted)
+		require.ErrorIs(t, err, unit.ErrCycleDetected)
+	})
+
+	t.Run("UpdatingADependency", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Given units A and B are registered
+		err := manager.Register(unitA)
+		require.NoError(t, err)
+		err = manager.Register(unitB)
+		require.NoError(t, err)
+
+		// Given Unit A depends on Unit B being unit.StatusStarted
+		err = manager.AddDependency(unitA, unitB, unit.StatusStarted)
+		require.NoError(t, err)
+
+		// When: The dependency is updated to unit.StatusComplete
+		err = manager.AddDependency(unitA, unitB, unit.StatusComplete)
+		require.NoError(t, err)
+
+		// Then: Unit A should only have one dependency, and it should be unit.StatusComplete
+		dependencies, err := manager.GetAllDependencies(unitA)
+		require.NoError(t, err)
+		require.Len(t, dependencies, 1)
+		assert.Equal(t, unit.StatusComplete, dependencies[0].RequiredStatus)
+	})
+}
+
+func TestManager_UpdateStatus(t *testing.T) {
+	t.Parallel()
+
+	t.Run("UpdateStatusTriggersReadinessRecalculation", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Given units A and B are registered
+		err := manager.Register(unitA)
+		require.NoError(t, err)
+		err = manager.Register(unitB)
+		require.NoError(t, err)
+
+		// Given Unit A depends on Unit B being unit.StatusStarted
+		err = manager.AddDependency(unitA, unitB, unit.StatusStarted)
+		require.NoError(t, err)
+
+		// Then: Unit A should not be ready (depends on B)
+		u, err := manager.Unit(unitA)
+		require.NoError(t, err)
+		assert.Equal(t, unit.StatusPending, u.Status())
+		isReady, err := manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.False(t, isReady)
+
+		// When: Unit B is started
+		err = manager.UpdateStatus(unitB, unit.StatusStarted)
+		require.NoError(t, err)
+
+		// Then: Unit A should be ready, because its dependency is now in the desired state.
+		u, err = manager.Unit(unitA)
+		require.NoError(t, err)
+		assert.Equal(t, unit.StatusPending, u.Status())
+		isReady, err = manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.True(t, isReady)
+	})
+
+	t.Run("UpdateStatusWithUnregisteredUnit", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Given Unit A is not registered
+		// When: Unit A is updated to unit.StatusStarted
+		err := manager.UpdateStatus(unitA, unit.StatusStarted)
+
+		// Then: a descriptive error communicates that the unit must be registered first.
+		require.ErrorIs(t, err, unit.ErrUnitNotFound)
+	})
+
+	t.Run("LinearChainDependencies", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Given units A, B, and C are registered
+		err := manager.Register(unitA)
+		require.NoError(t, err)
+		err = manager.Register(unitB)
+		require.NoError(t, err)
+		err = manager.Register(unitC)
+		require.NoError(t, err)
+
+		// Create chain: A depends on B being "started", B depends on C being "completed"
+		err = manager.AddDependency(unitA, unitB, unit.StatusStarted)
+		require.NoError(t, err)
+		err = manager.AddDependency(unitB, unitC, unit.StatusComplete)
+		require.NoError(t, err)
+
+		// Then: only Unit C should be ready (no dependencies)
+		u, err := manager.Unit(unitC)
+		require.NoError(t, err)
+		assert.Equal(t, unit.StatusPending, u.Status())
+		isReady, err := manager.IsReady(unitC)
+		require.NoError(t, err)
+		assert.True(t, isReady)
+
+		u, err = manager.Unit(unitB)
+		require.NoError(t, err)
+		assert.Equal(t, unit.StatusPending, u.Status())
+		isReady, err = manager.IsReady(unitB)
+		require.NoError(t, err)
+		assert.False(t, isReady)
+
+		u, err = manager.Unit(unitA)
+		require.NoError(t, err)
+		assert.Equal(t, unit.StatusPending, u.Status())
+		isReady, err = manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.False(t, isReady)
+
+		// When: Unit C is completed
+		err = manager.UpdateStatus(unitC, unit.StatusComplete)
+		require.NoError(t, err)
+
+		// Then: Unit B should be ready, because its dependency is now in the desired state.
+		u, err = manager.Unit(unitB)
+		require.NoError(t, err)
+		assert.Equal(t, unit.StatusPending, u.Status())
+		isReady, err = manager.IsReady(unitB)
+		require.NoError(t, err)
+		assert.True(t, isReady)
+
+		u, err = manager.Unit(unitA)
+		require.NoError(t, err)
+		assert.Equal(t, unit.StatusPending, u.Status())
+		isReady, err = manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.False(t, isReady)
+
+		u, err = manager.Unit(unitB)
+		require.NoError(t, err)
+		assert.Equal(t, unit.StatusPending, u.Status())
+		isReady, err = manager.IsReady(unitB)
+		require.NoError(t, err)
+		assert.True(t, isReady)
+
+		// When: Unit B is started
+		err = manager.UpdateStatus(unitB, unit.StatusStarted)
+		require.NoError(t, err)
+
+		// Then: Unit A should be ready, because its dependency is now in the desired state.
+		u, err = manager.Unit(unitA)
+		require.NoError(t, err)
+		assert.Equal(t, unit.StatusPending, u.Status())
+		isReady, err = manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.True(t, isReady)
+	})
+}
+
+func TestManager_GetUnmetDependencies(t *testing.T) {
+	t.Parallel()
+
+	t.Run("GetUnmetDependenciesForUnitWithNoDependencies", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Given: Unit A is registered
+		err := manager.Register(unitA)
+		require.NoError(t, err)
+
+		// Given: Unit A has no dependencies
+		// Then: Unit A should have no unmet dependencies
+		unmet, err := manager.GetUnmetDependencies(unitA)
+		require.NoError(t, err)
+		assert.Empty(t, unmet)
+	})
+
+	t.Run("GetUnmetDependenciesForUnitWithUnsatisfiedDependencies", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+		err := manager.Register(unitA)
+		require.NoError(t, err)
+		err = manager.Register(unitB)
+		require.NoError(t, err)
+
+		// Given: Unit A depends on Unit B being unit.StatusStarted
+		err = manager.AddDependency(unitA, unitB, unit.StatusStarted)
+		require.NoError(t, err)
+
+		unmet, err := manager.GetUnmetDependencies(unitA)
+		require.NoError(t, err)
+		require.Len(t, unmet, 1)
+
+		assert.Equal(t, unitA, unmet[0].Unit)
+		assert.Equal(t, unitB, unmet[0].DependsOn)
+		assert.Equal(t, unit.StatusStarted, unmet[0].RequiredStatus)
+		assert.False(t, unmet[0].IsSatisfied)
+	})
+
+	t.Run("GetUnmetDependenciesForUnitWithSatisfiedDependencies", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Given: Unit A and Unit B are registered
+		err := manager.Register(unitA)
+		require.NoError(t, err)
+		err = manager.Register(unitB)
+		require.NoError(t, err)
+
+		// Given: Unit A depends on Unit B being unit.StatusStarted
+		err = manager.AddDependency(unitA, unitB, unit.StatusStarted)
+		require.NoError(t, err)
+
+		// When: Unit B is started
+		err = manager.UpdateStatus(unitB, unit.StatusStarted)
+		require.NoError(t, err)
+
+		// Then: Unit A should have no unmet dependencies
+		unmet, err := manager.GetUnmetDependencies(unitA)
+		require.NoError(t, err)
+		assert.Empty(t, unmet)
+	})
+
+	t.Run("GetUnmetDependenciesForUnregisteredUnit", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// When: Unit A is requested
+		unmet, err := manager.GetUnmetDependencies(unitA)
+
+		// Then: a descriptive error communicates that the unit must be registered first.
+		require.ErrorIs(t, err, unit.ErrUnitNotFound)
+		assert.Nil(t, unmet)
+	})
+}
+
+func TestManager_MultipleDependencies(t *testing.T) {
+	t.Parallel()
+
+	t.Run("UnitWithMultipleDependencies", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Register all units
+		units := []unit.ID{unitA, unitB, unitC, unitD}
+		for _, unit := range units {
+			err := manager.Register(unit)
+			require.NoError(t, err)
+		}
+
+		// A depends on B being unit.StatusStarted AND C being "started"
+		err := manager.AddDependency(unitA, unitB, unit.StatusStarted)
+		require.NoError(t, err)
+		err = manager.AddDependency(unitA, unitC, unit.StatusStarted)
+		require.NoError(t, err)
+
+		// A should not be ready (depends on both B and C)
+		isReady, err := manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.False(t, isReady)
+
+		// Update B to unit.StatusStarted - A should still not be ready (needs C too)
+		err = manager.UpdateStatus(unitB, unit.StatusStarted)
+		require.NoError(t, err)
+
+		isReady, err = manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.False(t, isReady)
+
+		// Update C to "started" - A should now be ready
+		err = manager.UpdateStatus(unitC, unit.StatusStarted)
+		require.NoError(t, err)
+
+		isReady, err = manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.True(t, isReady)
+	})
+
+	t.Run("ComplexDependencyChain", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Register all units
+		units := []unit.ID{unitA, unitB, unitC, unitD}
+		for _, unit := range units {
+			err := manager.Register(unit)
+			require.NoError(t, err)
+		}
+
+		// Create complex dependency graph:
+		// A depends on B being unit.StatusStarted AND C being "started"
+		err := manager.AddDependency(unitA, unitB, unit.StatusStarted)
+		require.NoError(t, err)
+		err = manager.AddDependency(unitA, unitC, unit.StatusStarted)
+		require.NoError(t, err)
+		// B depends on D being "completed"
+		err = manager.AddDependency(unitB, unitD, unit.StatusComplete)
+		require.NoError(t, err)
+		// C depends on D being "completed"
+		err = manager.AddDependency(unitC, unitD, unit.StatusComplete)
+		require.NoError(t, err)
+
+		// Initially only D is ready
+		isReady, err := manager.IsReady(unitD)
+		require.NoError(t, err)
+		assert.True(t, isReady)
+		isReady, err = manager.IsReady(unitB)
+		require.NoError(t, err)
+		assert.False(t, isReady)
+		isReady, err = manager.IsReady(unitC)
+		require.NoError(t, err)
+		assert.False(t, isReady)
+		isReady, err = manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.False(t, isReady)
+
+		// Update D to "completed" - B and C should become ready
+		err = manager.UpdateStatus(unitD, unit.StatusComplete)
+		require.NoError(t, err)
+
+		isReady, err = manager.IsReady(unitB)
+		require.NoError(t, err)
+		assert.True(t, isReady)
+		isReady, err = manager.IsReady(unitC)
+		require.NoError(t, err)
+		assert.True(t, isReady)
+		isReady, err = manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.False(t, isReady)
+
+		// Update B to unit.StatusStarted - A should still not be ready (needs C)
+		err = manager.UpdateStatus(unitB, unit.StatusStarted)
+		require.NoError(t, err)
+
+		isReady, err = manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.False(t, isReady)
+
+		// Update C to "started" - A should now be ready
+		err = manager.UpdateStatus(unitC, unit.StatusStarted)
+		require.NoError(t, err)
+
+		isReady, err = manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.True(t, isReady)
+	})
+
+	t.Run("DifferentStatusTypes", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Register units
+		err := manager.Register(unitA)
+		require.NoError(t, err)
+		err = manager.Register(unitB)
+		require.NoError(t, err)
+		err = manager.Register(unitC)
+		require.NoError(t, err)
+
+		// Given: Unit A depends on Unit B being unit.StatusStarted
+		err = manager.AddDependency(unitA, unitB, unit.StatusStarted)
+		require.NoError(t, err)
+		// Given: Unit A depends on Unit C being "completed"
+		err = manager.AddDependency(unitA, unitC, unit.StatusComplete)
+		require.NoError(t, err)
+
+		// When: Unit B is started
+		err = manager.UpdateStatus(unitB, unit.StatusStarted)
+		require.NoError(t, err)
+
+		// Then: Unit A should not be ready, because only one of its dependencies is in the desired state.
+		// It still requires Unit C to be completed.
+		isReady, err := manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.False(t, isReady)
+
+		// When: Unit C is completed
+		err = manager.UpdateStatus(unitC, unit.StatusComplete)
+		require.NoError(t, err)
+
+		// Then: Unit A should be ready, because both of its dependencies are in the desired state.
+		isReady, err = manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.True(t, isReady)
+	})
+}
+
+func TestManager_IsReady(t *testing.T) {
+	t.Parallel()
+
+	t.Run("IsReadyWithUnregisteredUnit", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Given: a unit is not registered
+		u, err := manager.Unit(unitA)
+		require.NoError(t, err)
+		assert.Equal(t, unit.StatusNotRegistered, u.Status())
+		// Then: the unit is not ready
+		isReady, err := manager.IsReady(unitA)
+		require.NoError(t, err)
+		assert.False(t, isReady)
+	})
+}
+
+func TestManager_ToDOT(t *testing.T) {
+	t.Parallel()
+
+	t.Run("ExportSimpleGraph", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Register units
+		err := manager.Register(unitA)
+		require.NoError(t, err)
+		err = manager.Register(unitB)
+		require.NoError(t, err)
+
+		// Add dependency
+		err = manager.AddDependency(unitA, unitB, unit.StatusStarted)
+		require.NoError(t, err)
+
+		dot, err := manager.ExportDOT("test")
+		require.NoError(t, err)
+		assert.NotEmpty(t, dot)
+		assert.Contains(t, dot, "digraph")
+	})
+
+	t.Run("ExportComplexGraph", func(t *testing.T) {
+		t.Parallel()
+
+		manager := unit.NewManager()
+
+		// Register all units
+		units := []unit.ID{unitA, unitB, unitC, unitD}
+		for _, unit := range units {
+			err := manager.Register(unit)
+			require.NoError(t, err)
+		}
+
+		// Create complex dependency graph
+		// A depends on B and C, B depends on D, C depends on D
+		err := manager.AddDependency(unitA, unitB, unit.StatusStarted)
+		require.NoError(t, err)
+		err = manager.AddDependency(unitA, unitC, unit.StatusStarted)
+		require.NoError(t, err)
+		err = manager.AddDependency(unitB, unitD, unit.StatusComplete)
+		require.NoError(t, err)
+		err = manager.AddDependency(unitC, unitD, unit.StatusComplete)
+		require.NoError(t, err)
+
+		dot, err := manager.ExportDOT("complex")
+		require.NoError(t, err)
+		assert.NotEmpty(t, dot)
+		assert.Contains(t, dot, "digraph")
+	})
+}

cli/agent.go

@@ -11,6 +11,7 @@ import (
 	"os"
 	"path/filepath"
 	"runtime"
+	"slices"
 	"strconv"
 	"strings"
 	"time"
@@ -201,18 +202,15 @@ func workspaceAgent() *serpent.Command {
 			// Enable pprof handler
 			// This prevents the pprof import from being accidentally deleted.
 			_ = pprof.Handler
-			pprofSrvClose := ServeHandler(ctx, logger, nil, pprofAddress, "pprof")
-			defer pprofSrvClose()
-			if port, err := extractPort(pprofAddress); err == nil {
-				ignorePorts[port] = "pprof"
-			}
+			if pprofAddress != "" {
+				pprofSrvClose := ServeHandler(ctx, logger, nil, pprofAddress, "pprof")
+				defer pprofSrvClose()
 
-			if port, err := extractPort(prometheusAddress); err == nil {
-				ignorePorts[port] = "prometheus"
-			}
-
-			if port, err := extractPort(debugAddress); err == nil {
-				ignorePorts[port] = "debug"
+				if port, err := extractPort(pprofAddress); err == nil {
+					ignorePorts[port] = "pprof"
+				}
+			} else {
+				logger.Debug(ctx, "pprof address is empty, disabling pprof server")
 			}
 
 			executablePath, err := os.Executable()
@@ -276,6 +274,28 @@ func workspaceAgent() *serpent.Command {
 			for {
 				prometheusRegistry := prometheus.NewRegistry()
 
+				promHandler := agent.PrometheusMetricsHandler(prometheusRegistry, logger)
+				var serverClose []func()
+				if prometheusAddress != "" {
+					prometheusSrvClose := ServeHandler(ctx, logger, promHandler, prometheusAddress, "prometheus")
+					serverClose = append(serverClose, prometheusSrvClose)
+
+					if port, err := extractPort(prometheusAddress); err == nil {
+						ignorePorts[port] = "prometheus"
+					}
+				} else {
+					logger.Debug(ctx, "prometheus address is empty, disabling prometheus server")
+				}
+
+				if debugAddress != "" {
+					// ServerHandle depends on `agnt.HTTPDebug()`, but `agnt`
+					// depends on `ignorePorts`. Keep this if statement in sync
+					// with below.
+					if port, err := extractPort(debugAddress); err == nil {
+						ignorePorts[port] = "debug"
+					}
+				}
+
 				agnt := agent.New(agent.Options{
 					Client:        client,
 					Logger:        logger,
@@ -299,10 +319,15 @@ func workspaceAgent() *serpent.Command {
 					},
 				})
 
-				promHandler := agent.PrometheusMetricsHandler(prometheusRegistry, logger)
-				prometheusSrvClose := ServeHandler(ctx, logger, promHandler, prometheusAddress, "prometheus")
-
-				debugSrvClose := ServeHandler(ctx, logger, agnt.HTTPDebug(), debugAddress, "debug")
+				if debugAddress != "" {
+					// ServerHandle depends on `agnt.HTTPDebug()`, but `agnt`
+					// depends on `ignorePorts`. Keep this if statement in sync
+					// with above.
+					debugSrvClose := ServeHandler(ctx, logger, agnt.HTTPDebug(), debugAddress, "debug")
+					serverClose = append(serverClose, debugSrvClose)
+				} else {
+					logger.Debug(ctx, "debug address is empty, disabling debug server")
+				}
 
 				select {
 				case <-ctx.Done():
@@ -314,8 +339,11 @@ func workspaceAgent() *serpent.Command {
 				}
 
 				lastErr = agnt.Close()
-				debugSrvClose()
-				prometheusSrvClose()
+
+				slices.Reverse(serverClose)
+				for _, closeFunc := range serverClose {
+					closeFunc()
+				}
 
 				if mustExit {
 					break

cli/agent_test.go

@@ -178,6 +178,51 @@ func TestWorkspaceAgent(t *testing.T) {
 		require.Greater(t, atomic.LoadInt64(&called), int64(0), "expected coderd to be reached with custom headers")
 		require.Greater(t, atomic.LoadInt64(&derpCalled), int64(0), "expected /derp to be called with custom headers")
 	})
+
+	t.Run("DisabledServers", func(t *testing.T) {
+		t.Parallel()
+
+		client, db := coderdtest.NewWithDatabase(t, nil)
+		user := coderdtest.CreateFirstUser(t, client)
+		r := dbfake.WorkspaceBuild(t, db, database.WorkspaceTable{
+			OrganizationID: user.OrganizationID,
+			OwnerID:        user.UserID,
+		}).WithAgent().Do()
+
+		logDir := t.TempDir()
+		inv, _ := clitest.New(t,
+			"agent",
+			"--auth", "token",
+			"--agent-token", r.AgentToken,
+			"--agent-url", client.URL.String(),
+			"--log-dir", logDir,
+			"--pprof-address", "",
+			"--prometheus-address", "",
+			"--debug-address", "",
+		)
+
+		clitest.Start(t, inv)
+
+		// Verify the agent is connected and working.
+		resources := coderdtest.NewWorkspaceAgentWaiter(t, client, r.Workspace.ID).
+			MatchResources(matchAgentWithVersion).Wait()
+		require.Len(t, resources, 1)
+		require.Len(t, resources[0].Agents, 1)
+		require.NotEmpty(t, resources[0].Agents[0].Version)
+
+		// Verify the servers are not listening by checking the log for disabled
+		// messages.
+		require.Eventually(t, func() bool {
+			logContent, err := os.ReadFile(filepath.Join(logDir, "coder-agent.log"))
+			if err != nil {
+				return false
+			}
+			logStr := string(logContent)
+			return strings.Contains(logStr, "pprof address is empty, disabling pprof server") &&
+				strings.Contains(logStr, "prometheus address is empty, disabling prometheus server") &&
+				strings.Contains(logStr, "debug address is empty, disabling debug server")
+		}, testutil.WaitLong, testutil.IntervalMedium)
+	})
 }
 
 func matchAgentWithVersion(rs []codersdk.WorkspaceResource) bool {

cli/create.go

@@ -577,53 +577,57 @@ func prepWorkspaceBuild(inv *serpent.Invocation, client *codersdk.Client, args p
 		return nil, xerrors.Errorf("template version git auth: %w", err)
 	}
 
-	// Run a dry-run with the given parameters to check correctness
-	dryRun, err := client.CreateTemplateVersionDryRun(inv.Context(), templateVersion.ID, codersdk.CreateTemplateVersionDryRunRequest{
-		WorkspaceName:       args.NewWorkspaceName,
-		RichParameterValues: buildParameters,
-	})
-	if err != nil {
-		return nil, xerrors.Errorf("begin workspace dry-run: %w", err)
-	}
+	// Only perform dry-run for workspace creation and updates
+	// Skip for start and restart to avoid unnecessary delays
+	if args.Action == WorkspaceCreate || args.Action == WorkspaceUpdate {
+		// Run a dry-run with the given parameters to check correctness
+		dryRun, err := client.CreateTemplateVersionDryRun(inv.Context(), templateVersion.ID, codersdk.CreateTemplateVersionDryRunRequest{
+			WorkspaceName:       args.NewWorkspaceName,
+			RichParameterValues: buildParameters,
+		})
+		if err != nil {
+			return nil, xerrors.Errorf("begin workspace dry-run: %w", err)
+		}
 
-	matchedProvisioners, err := client.TemplateVersionDryRunMatchedProvisioners(inv.Context(), templateVersion.ID, dryRun.ID)
-	if err != nil {
-		return nil, xerrors.Errorf("get matched provisioners: %w", err)
-	}
-	cliutil.WarnMatchedProvisioners(inv.Stdout, &matchedProvisioners, dryRun)
-	_, _ = fmt.Fprintln(inv.Stdout, "Planning workspace...")
-	err = cliui.ProvisionerJob(inv.Context(), inv.Stdout, cliui.ProvisionerJobOptions{
-		Fetch: func() (codersdk.ProvisionerJob, error) {
-			return client.TemplateVersionDryRun(inv.Context(), templateVersion.ID, dryRun.ID)
-		},
-		Cancel: func() error {
-			return client.CancelTemplateVersionDryRun(inv.Context(), templateVersion.ID, dryRun.ID)
-		},
-		Logs: func() (<-chan codersdk.ProvisionerJobLog, io.Closer, error) {
-			return client.TemplateVersionDryRunLogsAfter(inv.Context(), templateVersion.ID, dryRun.ID, 0)
-		},
-		// Don't show log output for the dry-run unless there's an error.
-		Silent: true,
-	})
-	if err != nil {
-		// TODO (Dean): reprompt for parameter values if we deem it to
-		// be a validation error
-		return nil, xerrors.Errorf("dry-run workspace: %w", err)
-	}
+		matchedProvisioners, err := client.TemplateVersionDryRunMatchedProvisioners(inv.Context(), templateVersion.ID, dryRun.ID)
+		if err != nil {
+			return nil, xerrors.Errorf("get matched provisioners: %w", err)
+		}
+		cliutil.WarnMatchedProvisioners(inv.Stdout, &matchedProvisioners, dryRun)
+		_, _ = fmt.Fprintln(inv.Stdout, "Planning workspace...")
+		err = cliui.ProvisionerJob(inv.Context(), inv.Stdout, cliui.ProvisionerJobOptions{
+			Fetch: func() (codersdk.ProvisionerJob, error) {
+				return client.TemplateVersionDryRun(inv.Context(), templateVersion.ID, dryRun.ID)
+			},
+			Cancel: func() error {
+				return client.CancelTemplateVersionDryRun(inv.Context(), templateVersion.ID, dryRun.ID)
+			},
+			Logs: func() (<-chan codersdk.ProvisionerJobLog, io.Closer, error) {
+				return client.TemplateVersionDryRunLogsAfter(inv.Context(), templateVersion.ID, dryRun.ID, 0)
+			},
+			// Don't show log output for the dry-run unless there's an error.
+			Silent: true,
+		})
+		if err != nil {
+			// TODO (Dean): reprompt for parameter values if we deem it to
+			// be a validation error
+			return nil, xerrors.Errorf("dry-run workspace: %w", err)
+		}
 
-	resources, err := client.TemplateVersionDryRunResources(inv.Context(), templateVersion.ID, dryRun.ID)
-	if err != nil {
-		return nil, xerrors.Errorf("get workspace dry-run resources: %w", err)
-	}
+		resources, err := client.TemplateVersionDryRunResources(inv.Context(), templateVersion.ID, dryRun.ID)
+		if err != nil {
+			return nil, xerrors.Errorf("get workspace dry-run resources: %w", err)
+		}
 
-	err = cliui.WorkspaceResources(inv.Stdout, resources, cliui.WorkspaceResourcesOptions{
-		WorkspaceName: args.NewWorkspaceName,
-		// Since agents haven't connected yet, hiding this makes more sense.
-		HideAgentState: true,
-		Title:          "Workspace Preview",
-	})
-	if err != nil {
-		return nil, xerrors.Errorf("get resources: %w", err)
+		err = cliui.WorkspaceResources(inv.Stdout, resources, cliui.WorkspaceResourcesOptions{
+			WorkspaceName: args.NewWorkspaceName,
+			// Since agents haven't connected yet, hiding this makes more sense.
+			HideAgentState: true,
+			Title:          "Workspace Preview",
+		})
+		if err != nil {
+			return nil, xerrors.Errorf("get resources: %w", err)
+		}
 	}
 
 	return buildParameters, nil

cli/exp_scaletest.go

@@ -64,7 +64,9 @@ func (r *RootCmd) scaletestCmd() *serpent.Command {
 			r.scaletestWorkspaceTraffic(),
 			r.scaletestAutostart(),
 			r.scaletestNotifications(),
+			r.scaletestTaskStatus(),
 			r.scaletestSMTP(),
+			r.scaletestPrebuilds(),
 		},
 	}
 
@@ -384,6 +386,88 @@ func (s *scaletestPrometheusFlags) attach(opts *serpent.OptionSet) {
 	)
 }
 
+// workspaceTargetFlags holds common flags for targeting specific workspaces in scale tests.
+type workspaceTargetFlags struct {
+	template         string
+	targetWorkspaces string
+	useHostLogin     bool
+}
+
+// attach adds the workspace target flags to the given options set.
+func (f *workspaceTargetFlags) attach(opts *serpent.OptionSet) {
+	*opts = append(*opts,
+		serpent.Option{
+			Flag:          "template",
+			FlagShorthand: "t",
+			Env:           "CODER_SCALETEST_TEMPLATE",
+			Description:   "Name or ID of the template. Traffic generation will be limited to workspaces created from this template.",
+			Value:         serpent.StringOf(&f.template),
+		},
+		serpent.Option{
+			Flag:        "target-workspaces",
+			Env:         "CODER_SCALETEST_TARGET_WORKSPACES",
+			Description: "Target a specific range of workspaces in the format [START]:[END] (exclusive). Example: 0:10 will target the 10 first alphabetically sorted workspaces (0-9).",
+			Value:       serpent.StringOf(&f.targetWorkspaces),
+		},
+		serpent.Option{
+			Flag:        "use-host-login",
+			Env:         "CODER_SCALETEST_USE_HOST_LOGIN",
+			Default:     "false",
+			Description: "Connect as the currently logged in user.",
+			Value:       serpent.BoolOf(&f.useHostLogin),
+		},
+	)
+}
+
+// getTargetedWorkspaces retrieves the workspaces based on the template filter and target range. warnWriter is where to
+// write a warning message if any workspaces were skipped due to ownership mismatch.
+func (f *workspaceTargetFlags) getTargetedWorkspaces(ctx context.Context, client *codersdk.Client, organizationIDs []uuid.UUID, warnWriter io.Writer) ([]codersdk.Workspace, error) {
+	// Validate template if provided
+	if f.template != "" {
+		_, err := parseTemplate(ctx, client, organizationIDs, f.template)
+		if err != nil {
+			return nil, xerrors.Errorf("parse template: %w", err)
+		}
+	}
+
+	// Parse target range
+	targetStart, targetEnd, err := parseTargetRange("workspaces", f.targetWorkspaces)
+	if err != nil {
+		return nil, xerrors.Errorf("parse target workspaces: %w", err)
+	}
+
+	// Determine owner based on useHostLogin
+	var owner string
+	if f.useHostLogin {
+		owner = codersdk.Me
+	}
+
+	// Get workspaces
+	workspaces, numSkipped, err := getScaletestWorkspaces(ctx, client, owner, f.template)
+	if err != nil {
+		return nil, err
+	}
+	if numSkipped > 0 {
+		cliui.Warnf(warnWriter, "CODER_DISABLE_OWNER_WORKSPACE_ACCESS is set on the deployment.\n\t%d workspace(s) were skipped due to ownership mismatch.\n\tSet --use-host-login to only target workspaces you own.", numSkipped)
+	}
+
+	// Adjust targetEnd if not specified
+	if targetEnd == 0 {
+		targetEnd = len(workspaces)
+	}
+
+	// Validate range
+	if len(workspaces) == 0 {
+		return nil, xerrors.Errorf("no scaletest workspaces exist")
+	}
+	if targetEnd > len(workspaces) {
+		return nil, xerrors.Errorf("target workspace end %d is greater than the number of workspaces %d", targetEnd, len(workspaces))
+	}
+
+	// Return the sliced workspaces
+	return workspaces[targetStart:targetEnd], nil
+}
+
 func requireAdmin(ctx context.Context, client *codersdk.Client) (codersdk.User, error) {
 	me, err := client.User(ctx, codersdk.Me)
 	if err != nil {
@@ -1193,12 +1277,10 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *serpent.Command {
 		bytesPerTick      int64
 		ssh               bool
 		disableDirect     bool
-		useHostLogin      bool
 		app               string
-		template          string
-		targetWorkspaces  string
 		workspaceProxyURL string
 
+		targetFlags     = &workspaceTargetFlags{}
 		tracingFlags    = &scaletestTracingFlags{}
 		strategy        = &scaletestStrategyFlags{}
 		cleanupStrategy = newScaletestCleanupStrategy()
@@ -1243,15 +1325,9 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *serpent.Command {
 				},
 			}
 
-			if template != "" {
-				_, err := parseTemplate(ctx, client, me.OrganizationIDs, template)
-				if err != nil {
-					return xerrors.Errorf("parse template: %w", err)
-				}
-			}
-			targetWorkspaceStart, targetWorkspaceEnd, err := parseTargetRange("workspaces", targetWorkspaces)
+			workspaces, err := targetFlags.getTargetedWorkspaces(ctx, client, me.OrganizationIDs, inv.Stdout)
 			if err != nil {
-				return xerrors.Errorf("parse target workspaces: %w", err)
+				return err
 			}
 
 			appHost, err := client.AppHost(ctx)
@@ -1259,30 +1335,6 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *serpent.Command {
 				return xerrors.Errorf("get app host: %w", err)
 			}
 
-			var owner string
-			if useHostLogin {
-				owner = codersdk.Me
-			}
-
-			workspaces, numSkipped, err := getScaletestWorkspaces(inv.Context(), client, owner, template)
-			if err != nil {
-				return err
-			}
-			if numSkipped > 0 {
-				cliui.Warnf(inv.Stdout, "CODER_DISABLE_OWNER_WORKSPACE_ACCESS is set on the deployment.\n\t%d workspace(s) were skipped due to ownership mismatch.\n\tSet --use-host-login to only target workspaces you own.", numSkipped)
-			}
-
-			if targetWorkspaceEnd == 0 {
-				targetWorkspaceEnd = len(workspaces)
-			}
-
-			if len(workspaces) == 0 {
-				return xerrors.Errorf("no scaletest workspaces exist")
-			}
-			if targetWorkspaceEnd > len(workspaces) {
-				return xerrors.Errorf("target workspace end %d is greater than the number of workspaces %d", targetWorkspaceEnd, len(workspaces))
-			}
-
 			tracerProvider, closeTracing, tracingEnabled, err := tracingFlags.provider(ctx)
 			if err != nil {
 				return xerrors.Errorf("create tracer provider: %w", err)
@@ -1307,10 +1359,6 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *serpent.Command {
 
 			th := harness.NewTestHarness(strategy.toStrategy(), cleanupStrategy.toStrategy())
 			for idx, ws := range workspaces {
-				if idx < targetWorkspaceStart || idx >= targetWorkspaceEnd {
-					continue
-				}
-
 				var (
 					agent codersdk.WorkspaceAgent
 					name  = "workspace-traffic"
@@ -1415,19 +1463,6 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *serpent.Command {
 	}
 
 	cmd.Options = []serpent.Option{
-		{
-			Flag:          "template",
-			FlagShorthand: "t",
-			Env:           "CODER_SCALETEST_TEMPLATE",
-			Description:   "Name or ID of the template. Traffic generation will be limited to workspaces created from this template.",
-			Value:         serpent.StringOf(&template),
-		},
-		{
-			Flag:        "target-workspaces",
-			Env:         "CODER_SCALETEST_TARGET_WORKSPACES",
-			Description: "Target a specific range of workspaces in the format [START]:[END] (exclusive). Example: 0:10 will target the 10 first alphabetically sorted workspaces (0-9).",
-			Value:       serpent.StringOf(&targetWorkspaces),
-		},
 		{
 			Flag:        "bytes-per-tick",
 			Env:         "CODER_SCALETEST_WORKSPACE_TRAFFIC_BYTES_PER_TICK",
@@ -1463,13 +1498,6 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *serpent.Command {
 			Description: "Send WebSocket traffic to a workspace app (proxied via coderd), cannot be used with --ssh.",
 			Value:       serpent.StringOf(&app),
 		},
-		{
-			Flag:        "use-host-login",
-			Env:         "CODER_SCALETEST_USE_HOST_LOGIN",
-			Default:     "false",
-			Description: "Connect as the currently logged in user.",
-			Value:       serpent.BoolOf(&useHostLogin),
-		},
 		{
 			Flag:        "workspace-proxy-url",
 			Env:         "CODER_SCALETEST_WORKSPACE_PROXY_URL",
@@ -1479,6 +1507,7 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *serpent.Command {
 		},
 	}
 
+	targetFlags.attach(&cmd.Options)
 	tracingFlags.attach(&cmd.Options)
 	strategy.attach(&cmd.Options)
 	cleanupStrategy.attach(&cmd.Options)

cli/exp_scaletest_notifications.go

@@ -3,6 +3,7 @@
 package cli
 
 import (
+	"bytes"
 	"context"
 	"fmt"
 	"net/http"
@@ -29,12 +30,13 @@ import (
 
 func (r *RootCmd) scaletestNotifications() *serpent.Command {
 	var (
-		userCount           int64
-		ownerUserPercentage float64
-		notificationTimeout time.Duration
-		dialTimeout         time.Duration
-		noCleanup           bool
-		smtpAPIURL          string
+		userCount               int64
+		templateAdminPercentage float64
+		notificationTimeout     time.Duration
+		smtpRequestTimeout      time.Duration
+		dialTimeout             time.Duration
+		noCleanup               bool
+		smtpAPIURL              string
 
 		tracingFlags = &scaletestTracingFlags{}
 
@@ -77,24 +79,24 @@ func (r *RootCmd) scaletestNotifications() *serpent.Command {
 				return xerrors.Errorf("--user-count must be greater than 0")
 			}
 
-			if ownerUserPercentage < 0 || ownerUserPercentage > 100 {
-				return xerrors.Errorf("--owner-user-percentage must be between 0 and 100")
+			if templateAdminPercentage < 0 || templateAdminPercentage > 100 {
+				return xerrors.Errorf("--template-admin-percentage must be between 0 and 100")
 			}
 
 			if smtpAPIURL != "" && !strings.HasPrefix(smtpAPIURL, "http://") && !strings.HasPrefix(smtpAPIURL, "https://") {
 				return xerrors.Errorf("--smtp-api-url must start with http:// or https://")
 			}
 
-			ownerUserCount := int64(float64(userCount) * ownerUserPercentage / 100)
-			if ownerUserCount == 0 && ownerUserPercentage > 0 {
-				ownerUserCount = 1
+			templateAdminCount := int64(float64(userCount) * templateAdminPercentage / 100)
+			if templateAdminCount == 0 && templateAdminPercentage > 0 {
+				templateAdminCount = 1
 			}
-			regularUserCount := userCount - ownerUserCount
+			regularUserCount := userCount - templateAdminCount
 
 			_, _ = fmt.Fprintf(inv.Stderr, "Distribution plan:\n")
 			_, _ = fmt.Fprintf(inv.Stderr, "  Total users: %d\n", userCount)
-			_, _ = fmt.Fprintf(inv.Stderr, "  Owner users: %d (%.1f%%)\n", ownerUserCount, ownerUserPercentage)
-			_, _ = fmt.Fprintf(inv.Stderr, "  Regular users: %d (%.1f%%)\n", regularUserCount, 100.0-ownerUserPercentage)
+			_, _ = fmt.Fprintf(inv.Stderr, "  Template admins: %d (%.1f%%)\n", templateAdminCount, templateAdminPercentage)
+			_, _ = fmt.Fprintf(inv.Stderr, "  Regular users: %d (%.1f%%)\n", regularUserCount, 100.0-templateAdminPercentage)
 
 			outputs, err := output.parse()
 			if err != nil {
@@ -127,13 +129,12 @@ func (r *RootCmd) scaletestNotifications() *serpent.Command {
 			_, _ = fmt.Fprintln(inv.Stderr, "Creating users...")
 
 			dialBarrier := &sync.WaitGroup{}
-			ownerWatchBarrier := &sync.WaitGroup{}
+			templateAdminWatchBarrier := &sync.WaitGroup{}
 			dialBarrier.Add(int(userCount))
-			ownerWatchBarrier.Add(int(ownerUserCount))
+			templateAdminWatchBarrier.Add(int(templateAdminCount))
 
 			expectedNotificationIDs := map[uuid.UUID]struct{}{
-				notificationsLib.TemplateUserAccountCreated: {},
-				notificationsLib.TemplateUserAccountDeleted: {},
+				notificationsLib.TemplateTemplateDeleted: {},
 			}
 
 			triggerTimes := make(map[uuid.UUID]chan time.Time, len(expectedNotificationIDs))
@@ -141,20 +142,31 @@ func (r *RootCmd) scaletestNotifications() *serpent.Command {
 				triggerTimes[id] = make(chan time.Time, 1)
 			}
 
+			smtpHTTPTransport := &http.Transport{
+				MaxConnsPerHost:     512,
+				MaxIdleConnsPerHost: 512,
+				IdleConnTimeout:     60 * time.Second,
+			}
+			smtpHTTPClient := &http.Client{
+				Transport: smtpHTTPTransport,
+			}
+
 			configs := make([]notifications.Config, 0, userCount)
-			for range ownerUserCount {
+			for range templateAdminCount {
 				config := notifications.Config{
 					User: createusers.Config{
 						OrganizationID: me.OrganizationIDs[0],
 					},
-					Roles:                    []string{codersdk.RoleOwner},
+					Roles:                    []string{codersdk.RoleTemplateAdmin},
 					NotificationTimeout:      notificationTimeout,
 					DialTimeout:              dialTimeout,
 					DialBarrier:              dialBarrier,
-					ReceivingWatchBarrier:    ownerWatchBarrier,
+					ReceivingWatchBarrier:    templateAdminWatchBarrier,
 					ExpectedNotificationsIDs: expectedNotificationIDs,
 					Metrics:                  metrics,
 					SMTPApiURL:               smtpAPIURL,
+					SMTPRequestTimeout:       smtpRequestTimeout,
+					SMTPHttpClient:           smtpHTTPClient,
 				}
 				if err := config.Validate(); err != nil {
 					return xerrors.Errorf("validate config: %w", err)
@@ -170,9 +182,8 @@ func (r *RootCmd) scaletestNotifications() *serpent.Command {
 					NotificationTimeout:   notificationTimeout,
 					DialTimeout:           dialTimeout,
 					DialBarrier:           dialBarrier,
-					ReceivingWatchBarrier: ownerWatchBarrier,
+					ReceivingWatchBarrier: templateAdminWatchBarrier,
 					Metrics:               metrics,
-					SMTPApiURL:            smtpAPIURL,
 				}
 				if err := config.Validate(); err != nil {
 					return xerrors.Errorf("validate config: %w", err)
@@ -180,7 +191,7 @@ func (r *RootCmd) scaletestNotifications() *serpent.Command {
 				configs = append(configs, config)
 			}
 
-			go triggerUserNotifications(
+			go triggerNotifications(
 				ctx,
 				logger,
 				client,
@@ -261,23 +272,30 @@ func (r *RootCmd) scaletestNotifications() *serpent.Command {
 			Required:      true,
 		},
 		{
-			Flag:        "owner-user-percentage",
-			Env:         "CODER_SCALETEST_NOTIFICATION_OWNER_USER_PERCENTAGE",
+			Flag:        "template-admin-percentage",
+			Env:         "CODER_SCALETEST_NOTIFICATION_TEMPLATE_ADMIN_PERCENTAGE",
 			Default:     "20.0",
-			Description: "Percentage of users to assign Owner role to (0-100).",
-			Value:       serpent.Float64Of(&ownerUserPercentage),
+			Description: "Percentage of users to assign Template Admin role to (0-100).",
+			Value:       serpent.Float64Of(&templateAdminPercentage),
 		},
 		{
 			Flag:        "notification-timeout",
 			Env:         "CODER_SCALETEST_NOTIFICATION_TIMEOUT",
-			Default:     "5m",
+			Default:     "10m",
 			Description: "How long to wait for notifications after triggering.",
 			Value:       serpent.DurationOf(&notificationTimeout),
 		},
+		{
+			Flag:        "smtp-request-timeout",
+			Env:         "CODER_SCALETEST_SMTP_REQUEST_TIMEOUT",
+			Default:     "5m",
+			Description: "Timeout for SMTP requests.",
+			Value:       serpent.DurationOf(&smtpRequestTimeout),
+		},
 		{
 			Flag:        "dial-timeout",
 			Env:         "CODER_SCALETEST_DIAL_TIMEOUT",
-			Default:     "2m",
+			Default:     "10m",
 			Description: "Timeout for dialing the notification websocket endpoint.",
 			Value:       serpent.DurationOf(&dialTimeout),
 		},
@@ -379,9 +397,9 @@ func computeNotificationLatencies(
 	return nil
 }
 
-// triggerUserNotifications waits for all test users to connect,
-// then creates and deletes a test user to trigger notification events for testing.
-func triggerUserNotifications(
+// triggerNotifications waits for all test users to connect,
+// then creates and deletes a test template to trigger notification events for testing.
+func triggerNotifications(
 	ctx context.Context,
 	logger slog.Logger,
 	client *codersdk.Client,
@@ -414,34 +432,49 @@ func triggerUserNotifications(
 		return
 	}
 
-	const (
-		triggerUsername = "scaletest-trigger-user"
-		triggerEmail    = "scaletest-trigger@example.com"
-	)
+	logger.Info(ctx, "creating test template to test notifications")
 
-	logger.Info(ctx, "creating test user to test notifications",
-		slog.F("username", triggerUsername),
-		slog.F("email", triggerEmail),
-		slog.F("org_id", orgID))
+	// Upload empty template file.
+	file, err := client.Upload(ctx, codersdk.ContentTypeTar, bytes.NewReader([]byte{}))
+	if err != nil {
+		logger.Error(ctx, "upload test template", slog.Error(err))
+		return
+	}
+	logger.Info(ctx, "test template uploaded", slog.F("file_id", file.ID))
 
-	testUser, err := client.CreateUserWithOrgs(ctx, codersdk.CreateUserRequestWithOrgs{
-		OrganizationIDs: []uuid.UUID{orgID},
-		Username:        triggerUsername,
-		Email:           triggerEmail,
-		Password:        "test-password-123",
+	// Create template version.
+	version, err := client.CreateTemplateVersion(ctx, orgID, codersdk.CreateTemplateVersionRequest{
+		StorageMethod: codersdk.ProvisionerStorageMethodFile,
+		FileID:        file.ID,
+		Provisioner:   codersdk.ProvisionerTypeEcho,
 	})
 	if err != nil {
-		logger.Error(ctx, "create test user", slog.Error(err))
+		logger.Error(ctx, "create test template version", slog.Error(err))
 		return
 	}
-	expectedNotifications[notificationsLib.TemplateUserAccountCreated] <- time.Now()
+	logger.Info(ctx, "test template version created", slog.F("template_version_id", version.ID))
 
-	err = client.DeleteUser(ctx, testUser.ID)
+	// Create template.
+	testTemplate, err := client.CreateTemplate(ctx, orgID, codersdk.CreateTemplateRequest{
+		Name:        "scaletest-test-template",
+		Description: "scaletest-test-template",
+		VersionID:   version.ID,
+	})
 	if err != nil {
-		logger.Error(ctx, "delete test user", slog.Error(err))
+		logger.Error(ctx, "create test template", slog.Error(err))
 		return
 	}
-	expectedNotifications[notificationsLib.TemplateUserAccountDeleted] <- time.Now()
-	close(expectedNotifications[notificationsLib.TemplateUserAccountCreated])
-	close(expectedNotifications[notificationsLib.TemplateUserAccountDeleted])
+	logger.Info(ctx, "test template created", slog.F("template_id", testTemplate.ID))
+
+	// Delete template to trigger notification.
+	err = client.DeleteTemplate(ctx, testTemplate.ID)
+	if err != nil {
+		logger.Error(ctx, "delete test template", slog.Error(err))
+		return
+	}
+	logger.Info(ctx, "test template deleted", slog.F("template_id", testTemplate.ID))
+
+	// Record expected notification.
+	expectedNotifications[notificationsLib.TemplateTemplateDeleted] <- time.Now()
+	close(expectedNotifications[notificationsLib.TemplateTemplateDeleted])
 }

cli/exp_scaletest_prebuilds.go

@@ -0,0 +1,297 @@
+//go:build !slim
+
+package cli
+
+import (
+	"fmt"
+	"net/http"
+	"os/signal"
+	"strconv"
+	"sync"
+	"time"
+
+	"github.com/prometheus/client_golang/prometheus"
+	"github.com/prometheus/client_golang/prometheus/promhttp"
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/codersdk"
+	"github.com/coder/coder/v2/scaletest/harness"
+	"github.com/coder/coder/v2/scaletest/prebuilds"
+	"github.com/coder/quartz"
+	"github.com/coder/serpent"
+)
+
+func (r *RootCmd) scaletestPrebuilds() *serpent.Command {
+	var (
+		numTemplates              int64
+		numPresets                int64
+		numPresetPrebuilds        int64
+		templateVersionJobTimeout time.Duration
+		prebuildWorkspaceTimeout  time.Duration
+		noCleanup                 bool
+
+		tracingFlags    = &scaletestTracingFlags{}
+		timeoutStrategy = &timeoutFlags{}
+		cleanupStrategy = newScaletestCleanupStrategy()
+		output          = &scaletestOutputFlags{}
+		prometheusFlags = &scaletestPrometheusFlags{}
+	)
+
+	cmd := &serpent.Command{
+		Use:   "prebuilds",
+		Short: "Creates prebuild workspaces on the Coder server.",
+		Handler: func(inv *serpent.Invocation) error {
+			ctx := inv.Context()
+			client, err := r.InitClient(inv)
+			if err != nil {
+				return err
+			}
+
+			notifyCtx, stop := signal.NotifyContext(ctx, StopSignals...)
+			defer stop()
+			ctx = notifyCtx
+
+			me, err := requireAdmin(ctx, client)
+			if err != nil {
+				return err
+			}
+
+			client.HTTPClient = &http.Client{
+				Transport: &codersdk.HeaderTransport{
+					Transport: http.DefaultTransport,
+					Header: map[string][]string{
+						codersdk.BypassRatelimitHeader: {"true"},
+					},
+				},
+			}
+
+			if numTemplates <= 0 {
+				return xerrors.Errorf("--num-templates must be greater than 0")
+			}
+			if numPresets <= 0 {
+				return xerrors.Errorf("--num-presets must be greater than 0")
+			}
+			if numPresetPrebuilds <= 0 {
+				return xerrors.Errorf("--num-preset-prebuilds must be greater than 0")
+			}
+
+			outputs, err := output.parse()
+			if err != nil {
+				return xerrors.Errorf("parse output flags: %w", err)
+			}
+
+			tracerProvider, closeTracing, tracingEnabled, err := tracingFlags.provider(ctx)
+			if err != nil {
+				return xerrors.Errorf("create tracer provider: %w", err)
+			}
+			defer func() {
+				_, _ = fmt.Fprintln(inv.Stderr, "\nUploading traces...")
+				if err := closeTracing(ctx); err != nil {
+					_, _ = fmt.Fprintf(inv.Stderr, "\nError uploading traces: %+v\n", err)
+				}
+				_, _ = fmt.Fprintf(inv.Stderr, "Waiting %s for prometheus metrics to be scraped\n", prometheusFlags.Wait)
+				<-time.After(prometheusFlags.Wait)
+			}()
+			tracer := tracerProvider.Tracer(scaletestTracerName)
+
+			reg := prometheus.NewRegistry()
+			metrics := prebuilds.NewMetrics(reg)
+
+			logger := inv.Logger
+			prometheusSrvClose := ServeHandler(ctx, logger, promhttp.HandlerFor(reg, promhttp.HandlerOpts{}), prometheusFlags.Address, "prometheus")
+			defer prometheusSrvClose()
+
+			err = client.PutPrebuildsSettings(ctx, codersdk.PrebuildsSettings{
+				ReconciliationPaused: true,
+			})
+			if err != nil {
+				return xerrors.Errorf("pause prebuilds: %w", err)
+			}
+
+			setupBarrier := new(sync.WaitGroup)
+			setupBarrier.Add(int(numTemplates))
+			creationBarrier := new(sync.WaitGroup)
+			creationBarrier.Add(int(numTemplates))
+			deletionSetupBarrier := new(sync.WaitGroup)
+			deletionSetupBarrier.Add(1)
+			deletionBarrier := new(sync.WaitGroup)
+			deletionBarrier.Add(int(numTemplates))
+
+			th := harness.NewTestHarness(timeoutStrategy.wrapStrategy(harness.ConcurrentExecutionStrategy{}), cleanupStrategy.toStrategy())
+
+			for i := range numTemplates {
+				id := strconv.Itoa(int(i))
+				cfg := prebuilds.Config{
+					OrganizationID:            me.OrganizationIDs[0],
+					NumPresets:                int(numPresets),
+					NumPresetPrebuilds:        int(numPresetPrebuilds),
+					TemplateVersionJobTimeout: templateVersionJobTimeout,
+					PrebuildWorkspaceTimeout:  prebuildWorkspaceTimeout,
+					Metrics:                   metrics,
+					SetupBarrier:              setupBarrier,
+					CreationBarrier:           creationBarrier,
+					DeletionSetupBarrier:      deletionSetupBarrier,
+					DeletionBarrier:           deletionBarrier,
+					Clock:                     quartz.NewReal(),
+				}
+				err := cfg.Validate()
+				if err != nil {
+					return xerrors.Errorf("validate config: %w", err)
+				}
+
+				var runner harness.Runnable = prebuilds.NewRunner(client, cfg)
+				if tracingEnabled {
+					runner = &runnableTraceWrapper{
+						tracer:   tracer,
+						spanName: fmt.Sprintf("prebuilds/%s", id),
+						runner:   runner,
+					}
+				}
+
+				th.AddRun("prebuilds", id, runner)
+			}
+
+			_, _ = fmt.Fprintf(inv.Stderr, "Creating %d templates with %d presets and %d prebuilds per preset...\n",
+				numTemplates, numPresets, numPresetPrebuilds)
+			_, _ = fmt.Fprintf(inv.Stderr, "Total expected prebuilds: %d\n", numTemplates*numPresets*numPresetPrebuilds)
+
+			testCtx, testCancel := timeoutStrategy.toContext(ctx)
+			defer testCancel()
+
+			runErrCh := make(chan error, 1)
+			go func() {
+				runErrCh <- th.Run(testCtx)
+			}()
+
+			_, _ = fmt.Fprintln(inv.Stderr, "Waiting for all templates to be created...")
+			setupBarrier.Wait()
+			_, _ = fmt.Fprintln(inv.Stderr, "All templates created")
+
+			err = client.PutPrebuildsSettings(ctx, codersdk.PrebuildsSettings{
+				ReconciliationPaused: false,
+			})
+			if err != nil {
+				return xerrors.Errorf("resume prebuilds: %w", err)
+			}
+
+			_, _ = fmt.Fprintln(inv.Stderr, "Waiting for all prebuilds to be created...")
+			creationBarrier.Wait()
+			_, _ = fmt.Fprintln(inv.Stderr, "All prebuilds created")
+
+			err = client.PutPrebuildsSettings(ctx, codersdk.PrebuildsSettings{
+				ReconciliationPaused: true,
+			})
+			if err != nil {
+				return xerrors.Errorf("pause prebuilds before deletion: %w", err)
+			}
+
+			_, _ = fmt.Fprintln(inv.Stderr, "Prebuilds paused, signaling runners to prepare for deletion")
+			deletionSetupBarrier.Done()
+
+			_, _ = fmt.Fprintln(inv.Stderr, "Waiting for all templates to be updated with 0 prebuilds...")
+			deletionBarrier.Wait()
+			_, _ = fmt.Fprintln(inv.Stderr, "All templates updated")
+
+			err = client.PutPrebuildsSettings(ctx, codersdk.PrebuildsSettings{
+				ReconciliationPaused: false,
+			})
+			if err != nil {
+				return xerrors.Errorf("resume prebuilds for deletion: %w", err)
+			}
+
+			_, _ = fmt.Fprintln(inv.Stderr, "Waiting for all prebuilds to be deleted...")
+			err = <-runErrCh
+			if err != nil {
+				return xerrors.Errorf("run test harness (harness failure, not a test failure): %w", err)
+			}
+
+			// If the command was interrupted, skip cleanup & stats
+			if notifyCtx.Err() != nil {
+				return notifyCtx.Err()
+			}
+
+			res := th.Results()
+			for _, o := range outputs {
+				err = o.write(res, inv.Stdout)
+				if err != nil {
+					return xerrors.Errorf("write output %q to %q: %w", o.format, o.path, err)
+				}
+			}
+
+			if !noCleanup {
+				_, _ = fmt.Fprintln(inv.Stderr, "\nStarting cleanup (deleting templates)...")
+
+				cleanupCtx, cleanupCancel := cleanupStrategy.toContext(ctx)
+				defer cleanupCancel()
+
+				err = th.Cleanup(cleanupCtx)
+				if err != nil {
+					return xerrors.Errorf("cleanup tests: %w", err)
+				}
+
+				// If the cleanup was interrupted, skip stats
+				if notifyCtx.Err() != nil {
+					return notifyCtx.Err()
+				}
+			}
+
+			if res.TotalFail > 0 {
+				return xerrors.New("prebuild creation test failed, see above for more details")
+			}
+
+			return nil
+		},
+	}
+
+	cmd.Options = serpent.OptionSet{
+		{
+			Flag:        "num-templates",
+			Env:         "CODER_SCALETEST_PREBUILDS_NUM_TEMPLATES",
+			Default:     "1",
+			Description: "Number of templates to create for the test.",
+			Value:       serpent.Int64Of(&numTemplates),
+		},
+		{
+			Flag:        "num-presets",
+			Env:         "CODER_SCALETEST_PREBUILDS_NUM_PRESETS",
+			Default:     "1",
+			Description: "Number of presets per template.",
+			Value:       serpent.Int64Of(&numPresets),
+		},
+		{
+			Flag:        "num-preset-prebuilds",
+			Env:         "CODER_SCALETEST_PREBUILDS_NUM_PRESET_PREBUILDS",
+			Default:     "1",
+			Description: "Number of prebuilds per preset.",
+			Value:       serpent.Int64Of(&numPresetPrebuilds),
+		},
+		{
+			Flag:        "template-version-job-timeout",
+			Env:         "CODER_SCALETEST_PREBUILDS_TEMPLATE_VERSION_JOB_TIMEOUT",
+			Default:     "5m",
+			Description: "Timeout for template version provisioning jobs.",
+			Value:       serpent.DurationOf(&templateVersionJobTimeout),
+		},
+		{
+			Flag:        "prebuild-workspace-timeout",
+			Env:         "CODER_SCALETEST_PREBUILDS_WORKSPACE_TIMEOUT",
+			Default:     "10m",
+			Description: "Timeout for all prebuild workspaces to be created/deleted.",
+			Value:       serpent.DurationOf(&prebuildWorkspaceTimeout),
+		},
+		{
+			Flag:        "skip-cleanup",
+			Env:         "CODER_SCALETEST_PREBUILDS_SKIP_CLEANUP",
+			Description: "Skip cleanup (deletion test) and leave resources intact.",
+			Value:       serpent.BoolOf(&noCleanup),
+		},
+	}
+
+	tracingFlags.attach(&cmd.Options)
+	timeoutStrategy.attach(&cmd.Options)
+	cleanupStrategy.attach(&cmd.Options)
+	output.attach(&cmd.Options)
+	prometheusFlags.attach(&cmd.Options)
+
+	return cmd
+}

cli/exp_scaletest_taskstatus.go

@@ -0,0 +1,275 @@
+//go:build !slim
+
+package cli
+
+import (
+	"context"
+	"fmt"
+	"net/http"
+	"sync"
+	"time"
+
+	"github.com/google/uuid"
+	"github.com/prometheus/client_golang/prometheus"
+	"github.com/prometheus/client_golang/prometheus/promhttp"
+	"golang.org/x/xerrors"
+
+	"cdr.dev/slog"
+	"cdr.dev/slog/sloggers/sloghuman"
+	"github.com/coder/serpent"
+
+	"github.com/coder/coder/v2/codersdk"
+	"github.com/coder/coder/v2/scaletest/harness"
+	"github.com/coder/coder/v2/scaletest/taskstatus"
+)
+
+const (
+	taskStatusTestName = "task-status"
+)
+
+func (r *RootCmd) scaletestTaskStatus() *serpent.Command {
+	var (
+		count                int64
+		template             string
+		workspaceNamePrefix  string
+		appSlug              string
+		reportStatusPeriod   time.Duration
+		reportStatusDuration time.Duration
+		baselineDuration     time.Duration
+		tracingFlags         = &scaletestTracingFlags{}
+		prometheusFlags      = &scaletestPrometheusFlags{}
+		timeoutStrategy      = &timeoutFlags{}
+		cleanupStrategy      = newScaletestCleanupStrategy()
+		output               = &scaletestOutputFlags{}
+	)
+	orgContext := NewOrganizationContext()
+
+	cmd := &serpent.Command{
+		Use:   "task-status",
+		Short: "Generates load on the Coder server by simulating task status reporting",
+		Long: `This test creates external workspaces and simulates AI agents reporting task status.
+After all runners connect, it waits for the baseline duration before triggering status reporting.`,
+		Handler: func(inv *serpent.Invocation) error {
+			ctx := inv.Context()
+
+			outputs, err := output.parse()
+			if err != nil {
+				return xerrors.Errorf("could not parse --output flags: %w", err)
+			}
+
+			client, err := r.InitClient(inv)
+			if err != nil {
+				return err
+			}
+
+			org, err := orgContext.Selected(inv, client)
+			if err != nil {
+				return err
+			}
+
+			_, err = requireAdmin(ctx, client)
+			if err != nil {
+				return err
+			}
+
+			// Disable rate limits for this test
+			client.HTTPClient = &http.Client{
+				Transport: &codersdk.HeaderTransport{
+					Transport: http.DefaultTransport,
+					Header: map[string][]string{
+						codersdk.BypassRatelimitHeader: {"true"},
+					},
+				},
+			}
+
+			// Find the template
+			tpl, err := parseTemplate(ctx, client, []uuid.UUID{org.ID}, template)
+			if err != nil {
+				return xerrors.Errorf("parse template %q: %w", template, err)
+			}
+			templateID := tpl.ID
+
+			reg := prometheus.NewRegistry()
+			metrics := taskstatus.NewMetrics(reg)
+
+			logger := slog.Make(sloghuman.Sink(inv.Stdout)).Leveled(slog.LevelDebug)
+			prometheusSrvClose := ServeHandler(ctx, logger, promhttp.HandlerFor(reg, promhttp.HandlerOpts{}), prometheusFlags.Address, "prometheus")
+			defer prometheusSrvClose()
+
+			tracerProvider, closeTracing, tracingEnabled, err := tracingFlags.provider(ctx)
+			if err != nil {
+				return xerrors.Errorf("create tracer provider: %w", err)
+			}
+			defer func() {
+				// Allow time for traces to flush even if command context is
+				// canceled. This is a no-op if tracing is not enabled.
+				_, _ = fmt.Fprintln(inv.Stderr, "\nUploading traces...")
+				if err := closeTracing(ctx); err != nil {
+					_, _ = fmt.Fprintf(inv.Stderr, "\nError uploading traces: %+v\n", err)
+				}
+				// Wait for prometheus metrics to be scraped
+				_, _ = fmt.Fprintf(inv.Stderr, "Waiting %s for prometheus metrics to be scraped\n", prometheusFlags.Wait)
+				<-time.After(prometheusFlags.Wait)
+			}()
+			tracer := tracerProvider.Tracer(scaletestTracerName)
+
+			// Setup shared resources for coordination
+			connectedWaitGroup := &sync.WaitGroup{}
+			connectedWaitGroup.Add(int(count))
+			startReporting := make(chan struct{})
+
+			// Create the test harness
+			th := harness.NewTestHarness(
+				timeoutStrategy.wrapStrategy(harness.ConcurrentExecutionStrategy{}),
+				cleanupStrategy.toStrategy(),
+			)
+
+			// Create runners
+			for i := range count {
+				workspaceName := fmt.Sprintf("%s-%d", workspaceNamePrefix, i)
+				cfg := taskstatus.Config{
+					TemplateID:           templateID,
+					WorkspaceName:        workspaceName,
+					AppSlug:              appSlug,
+					ConnectedWaitGroup:   connectedWaitGroup,
+					StartReporting:       startReporting,
+					ReportStatusPeriod:   reportStatusPeriod,
+					ReportStatusDuration: reportStatusDuration,
+					Metrics:              metrics,
+					MetricLabelValues:    []string{},
+				}
+
+				if err := cfg.Validate(); err != nil {
+					return xerrors.Errorf("validate config for runner %d: %w", i, err)
+				}
+
+				var runner harness.Runnable = taskstatus.NewRunner(client, cfg)
+				if tracingEnabled {
+					runner = &runnableTraceWrapper{
+						tracer:   tracer,
+						spanName: fmt.Sprintf("%s/%d", taskStatusTestName, i),
+						runner:   runner,
+					}
+				}
+				th.AddRun(taskStatusTestName, workspaceName, runner)
+			}
+
+			// Start the test in a separate goroutine so we can coordinate timing
+			testCtx, testCancel := timeoutStrategy.toContext(ctx)
+			defer testCancel()
+			testDone := make(chan error)
+			go func() {
+				testDone <- th.Run(testCtx)
+			}()
+
+			// Wait for all runners to connect
+			logger.Info(ctx, "waiting for all runners to connect")
+			waitCtx, waitCancel := context.WithTimeout(ctx, 5*time.Minute)
+			defer waitCancel()
+
+			connectDone := make(chan struct{})
+			go func() {
+				connectedWaitGroup.Wait()
+				close(connectDone)
+			}()
+
+			select {
+			case <-waitCtx.Done():
+				return xerrors.Errorf("timeout waiting for runners to connect")
+			case <-connectDone:
+				logger.Info(ctx, "all runners connected")
+			}
+
+			// Wait for baseline duration
+			logger.Info(ctx, "waiting for baseline duration", slog.F("duration", baselineDuration))
+			select {
+			case <-ctx.Done():
+				return ctx.Err()
+			case <-time.After(baselineDuration):
+			}
+
+			// Trigger all runners to start reporting
+			logger.Info(ctx, "triggering runners to start reporting task status")
+			close(startReporting)
+
+			// Wait for the test to complete
+			err = <-testDone
+			if err != nil {
+				return xerrors.Errorf("run test harness: %w", err)
+			}
+
+			res := th.Results()
+			for _, o := range outputs {
+				err = o.write(res, inv.Stdout)
+				if err != nil {
+					return xerrors.Errorf("write output %q to %q: %w", o.format, o.path, err)
+				}
+			}
+
+			cleanupCtx, cleanupCancel := cleanupStrategy.toContext(ctx)
+			defer cleanupCancel()
+			err = th.Cleanup(cleanupCtx)
+			if err != nil {
+				return xerrors.Errorf("cleanup tests: %w", err)
+			}
+
+			if res.TotalFail > 0 {
+				return xerrors.New("load test failed, see above for more details")
+			}
+
+			return nil
+		},
+	}
+
+	cmd.Options = serpent.OptionSet{
+		{
+			Flag:        "count",
+			Description: "Number of concurrent runners to create.",
+			Default:     "10",
+			Value:       serpent.Int64Of(&count),
+		},
+		{
+			Flag:        "template",
+			Description: "Name or UUID of the template to use for the scale test. The template MUST include a coder_external_agent and a coder_app.",
+			Default:     "scaletest-task-status",
+			Value:       serpent.StringOf(&template),
+		},
+		{
+			Flag:        "workspace-name-prefix",
+			Description: "Prefix for workspace names (will be suffixed with index).",
+			Default:     "scaletest-task-status",
+			Value:       serpent.StringOf(&workspaceNamePrefix),
+		},
+		{
+			Flag:        "app-slug",
+			Description: "Slug of the app designated as the AI Agent.",
+			Default:     "ai-agent",
+			Value:       serpent.StringOf(&appSlug),
+		},
+		{
+			Flag:        "report-status-period",
+			Description: "Time between reporting task statuses.",
+			Default:     "10s",
+			Value:       serpent.DurationOf(&reportStatusPeriod),
+		},
+		{
+			Flag:        "report-status-duration",
+			Description: "Total time to report task statuses after baseline.",
+			Default:     "15m",
+			Value:       serpent.DurationOf(&reportStatusDuration),
+		},
+		{
+			Flag:        "baseline-duration",
+			Description: "Duration to wait after all runners connect before starting to report status.",
+			Default:     "10m",
+			Value:       serpent.DurationOf(&baselineDuration),
+		},
+	}
+	orgContext.AttachOptions(cmd)
+	output.attach(&cmd.Options)
+	tracingFlags.attach(&cmd.Options)
+	prometheusFlags.attach(&cmd.Options)
+	timeoutStrategy.attach(&cmd.Options)
+	cleanupStrategy.attach(&cmd.Options)
+	return cmd
+}

cli/exp_task_delete_test.go

@@ -56,19 +56,14 @@ func TestExpTaskDelete(t *testing.T) {
 				taskID := uuid.MustParse(id1)
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch {
-					case r.Method == http.MethodGet && r.URL.Path == "/api/experimental/tasks" && r.URL.Query().Get("q") == "owner:\"me\"":
+					case r.Method == http.MethodGet && r.URL.Path == "/api/experimental/tasks/me/exists":
 						c.nameResolves.Add(1)
-						httpapi.Write(r.Context(), w, http.StatusOK, struct {
-							Tasks []codersdk.Task `json:"tasks"`
-							Count int             `json:"count"`
-						}{
-							Tasks: []codersdk.Task{{
+						httpapi.Write(r.Context(), w, http.StatusOK,
+							codersdk.Task{
 								ID:        taskID,
 								Name:      "exists",
 								OwnerName: "me",
-							}},
-							Count: 1,
-						})
+							})
 					case r.Method == http.MethodDelete && r.URL.Path == "/api/experimental/tasks/me/"+id1:
 						c.deleteCalls.Add(1)
 						w.WriteHeader(http.StatusAccepted)
@@ -107,27 +102,21 @@ func TestExpTaskDelete(t *testing.T) {
 			name: "Multiple_YesFlag",
 			args: []string{"--yes", "first", id4},
 			buildHandler: func(c *testCounters) http.HandlerFunc {
-				firstID := uuid.MustParse(id3)
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch {
-					case r.Method == http.MethodGet && r.URL.Path == "/api/experimental/tasks" && r.URL.Query().Get("q") == "owner:\"me\"":
+					case r.Method == http.MethodGet && r.URL.Path == "/api/experimental/tasks/me/first":
 						c.nameResolves.Add(1)
-						httpapi.Write(r.Context(), w, http.StatusOK, struct {
-							Tasks []codersdk.Task `json:"tasks"`
-							Count int             `json:"count"`
-						}{
-							Tasks: []codersdk.Task{{
-								ID:        firstID,
-								Name:      "first",
-								OwnerName: "me",
-							}},
-							Count: 1,
+						httpapi.Write(r.Context(), w, http.StatusOK, codersdk.Task{
+							ID:        uuid.MustParse(id3),
+							Name:      "first",
+							OwnerName: "me",
 						})
 					case r.Method == http.MethodGet && r.URL.Path == "/api/experimental/tasks/me/"+id4:
+						c.nameResolves.Add(1)
 						httpapi.Write(r.Context(), w, http.StatusOK, codersdk.Task{
 							ID:        uuid.MustParse(id4),
 							OwnerName: "me",
-							Name:      "uuid-task-2",
+							Name:      "uuid-task-4",
 						})
 					case r.Method == http.MethodDelete && r.URL.Path == "/api/experimental/tasks/me/"+id3:
 						c.deleteCalls.Add(1)
@@ -141,7 +130,7 @@ func TestExpTaskDelete(t *testing.T) {
 				}
 			},
 			wantDeleteCalls:    2,
-			wantNameResolves:   1,
+			wantNameResolves:   2,
 			wantDeletedMessage: 2,
 		},
 		{
@@ -174,20 +163,14 @@ func TestExpTaskDelete(t *testing.T) {
 				taskID := uuid.MustParse(id5)
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch {
-					case r.Method == http.MethodGet && r.URL.Path == "/api/experimental/tasks" && r.URL.Query().Get("q") == "owner:\"me\"":
+					case r.Method == http.MethodGet && r.URL.Path == "/api/experimental/tasks/me/bad":
 						c.nameResolves.Add(1)
-						httpapi.Write(r.Context(), w, http.StatusOK, struct {
-							Tasks []codersdk.Task `json:"tasks"`
-							Count int             `json:"count"`
-						}{
-							Tasks: []codersdk.Task{{
-								ID:        taskID,
-								Name:      "bad",
-								OwnerName: "me",
-							}},
-							Count: 1,
+						httpapi.Write(r.Context(), w, http.StatusOK, codersdk.Task{
+							ID:        taskID,
+							Name:      "bad",
+							OwnerName: "me",
 						})
-					case r.Method == http.MethodDelete && r.URL.Path == "/api/experimental/tasks/me/"+id5:
+					case r.Method == http.MethodDelete && r.URL.Path == "/api/experimental/tasks/me/bad":
 						httpapi.InternalServerError(w, xerrors.New("boom"))
 					default:
 						httpapi.InternalServerError(w, xerrors.New("unwanted path: "+r.Method+" "+r.URL.Path))

cli/exp_task_list_test.go

@@ -2,7 +2,6 @@ package cli_test
 
 import (
 	"bytes"
-	"context"
 	"database/sql"
 	"encoding/json"
 	"io"
@@ -19,10 +18,7 @@ import (
 	"github.com/coder/coder/v2/cli/clitest"
 	"github.com/coder/coder/v2/coderd/coderdtest"
 	"github.com/coder/coder/v2/coderd/database"
-	"github.com/coder/coder/v2/coderd/database/dbauthz"
 	"github.com/coder/coder/v2/coderd/database/dbfake"
-	"github.com/coder/coder/v2/coderd/database/dbgen"
-	"github.com/coder/coder/v2/coderd/database/dbtime"
 	"github.com/coder/coder/v2/coderd/util/slice"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/pty/ptytest"
@@ -43,76 +39,22 @@ func makeAITask(t *testing.T, db database.Store, orgID, adminID, ownerID uuid.UU
 			},
 		}).Do()
 
-	ws := database.WorkspaceTable{
+	build := dbfake.WorkspaceBuild(t, db, database.WorkspaceTable{
 		OrganizationID: orgID,
 		OwnerID:        ownerID,
 		TemplateID:     tv.Template.ID,
-	}
-	build := dbfake.WorkspaceBuild(t, db, ws).
+	}).
 		Seed(database.WorkspaceBuild{
 			TemplateVersionID: tv.TemplateVersion.ID,
 			Transition:        transition,
-		}).WithAgent().Do()
-	dbgen.WorkspaceBuildParameters(t, db, []database.WorkspaceBuildParameter{
-		{
-			WorkspaceBuildID: build.Build.ID,
-			Name:             codersdk.AITaskPromptParameterName,
-			Value:            prompt,
-		},
-	})
-	agents, err := db.GetWorkspaceAgentsByWorkspaceAndBuildNumber(
-		dbauthz.AsSystemRestricted(context.Background()),
-		database.GetWorkspaceAgentsByWorkspaceAndBuildNumberParams{
-			WorkspaceID: build.Workspace.ID,
-			BuildNumber: build.Build.BuildNumber,
-		},
-	)
-	require.NoError(t, err)
-	require.NotEmpty(t, agents)
-	agentID := agents[0].ID
+		}).
+		WithAgent().
+		WithTask(database.TaskTable{
+			Prompt: prompt,
+		}, nil).
+		Do()
 
-	// Create a workspace app and set it as the sidebar app.
-	app := dbgen.WorkspaceApp(t, db, database.WorkspaceApp{
-		AgentID:     agentID,
-		Slug:        "task-sidebar",
-		DisplayName: "Task Sidebar",
-		External:    false,
-	})
-
-	// Update build flags to reference the sidebar app and HasAITask=true.
-	err = db.UpdateWorkspaceBuildFlagsByID(
-		dbauthz.AsSystemRestricted(context.Background()),
-		database.UpdateWorkspaceBuildFlagsByIDParams{
-			ID:               build.Build.ID,
-			HasAITask:        sql.NullBool{Bool: true, Valid: true},
-			HasExternalAgent: sql.NullBool{Bool: false, Valid: false},
-			SidebarAppID:     uuid.NullUUID{UUID: app.ID, Valid: true},
-			UpdatedAt:        build.Build.UpdatedAt,
-		},
-	)
-	require.NoError(t, err)
-
-	// Create a task record in the tasks table for the new data model.
-	task := dbgen.Task(t, db, database.TaskTable{
-		OrganizationID:     orgID,
-		OwnerID:            ownerID,
-		Name:               build.Workspace.Name,
-		WorkspaceID:        uuid.NullUUID{UUID: build.Workspace.ID, Valid: true},
-		TemplateVersionID:  tv.TemplateVersion.ID,
-		TemplateParameters: []byte("{}"),
-		Prompt:             prompt,
-		CreatedAt:          dbtime.Now(),
-	})
-
-	// Link the task to the workspace app.
-	dbgen.TaskWorkspaceApp(t, db, database.TaskWorkspaceApp{
-		TaskID:               task.ID,
-		WorkspaceBuildNumber: build.Build.BuildNumber,
-		WorkspaceAgentID:     uuid.NullUUID{UUID: agentID, Valid: true},
-		WorkspaceAppID:       uuid.NullUUID{UUID: app.ID, Valid: true},
-	})
-
-	return task
+	return build.Task
 }
 
 func TestExpTaskList(t *testing.T) {

cli/exp_task_status_test.go

@@ -36,17 +36,9 @@ func Test_TaskStatus(t *testing.T) {
 			hf: func(ctx context.Context, _ time.Time) func(w http.ResponseWriter, r *http.Request) {
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch r.URL.Path {
-					case "/api/experimental/tasks":
-						if r.URL.Query().Get("q") == "owner:\"me\"" {
-							httpapi.Write(ctx, w, http.StatusOK, struct {
-								Tasks []codersdk.Task `json:"tasks"`
-								Count int             `json:"count"`
-							}{
-								Tasks: []codersdk.Task{},
-								Count: 0,
-							})
-							return
-						}
+					case "/api/experimental/tasks/me/doesnotexist":
+						httpapi.ResourceNotFound(w)
+						return
 					default:
 						t.Errorf("unexpected path: %s", r.URL.Path)
 					}
@@ -60,35 +52,7 @@ func Test_TaskStatus(t *testing.T) {
 			hf: func(ctx context.Context, now time.Time) func(w http.ResponseWriter, r *http.Request) {
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch r.URL.Path {
-					case "/api/experimental/tasks":
-						if r.URL.Query().Get("q") == "owner:\"me\"" {
-							httpapi.Write(ctx, w, http.StatusOK, struct {
-								Tasks []codersdk.Task `json:"tasks"`
-								Count int             `json:"count"`
-							}{
-								Tasks: []codersdk.Task{{
-									ID:              uuid.MustParse("11111111-1111-1111-1111-111111111111"),
-									Name:            "exists",
-									OwnerName:       "me",
-									WorkspaceStatus: codersdk.WorkspaceStatusRunning,
-									CreatedAt:       now,
-									UpdatedAt:       now,
-									CurrentState: &codersdk.TaskStateEntry{
-										State:     codersdk.TaskStateWorking,
-										Timestamp: now,
-										Message:   "Thinking furiously...",
-									},
-									WorkspaceAgentHealth: &codersdk.WorkspaceAgentHealth{
-										Healthy: true,
-									},
-									WorkspaceAgentLifecycle: ptr.Ref(codersdk.WorkspaceAgentLifecycleReady),
-									Status:                  codersdk.TaskStatusActive,
-								}},
-								Count: 1,
-							})
-							return
-						}
-					case "/api/experimental/tasks/me/11111111-1111-1111-1111-111111111111":
+					case "/api/experimental/tasks/me/exists":
 						httpapi.Write(ctx, w, http.StatusOK, codersdk.Task{
 							ID:              uuid.MustParse("11111111-1111-1111-1111-111111111111"),
 							WorkspaceStatus: codersdk.WorkspaceStatusRunning,
@@ -124,30 +88,21 @@ func Test_TaskStatus(t *testing.T) {
 				var calls atomic.Int64
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch r.URL.Path {
-					case "/api/experimental/tasks":
-						if r.URL.Query().Get("q") == "owner:\"me\"" {
-							// Return initial task state for --watch test
-							httpapi.Write(ctx, w, http.StatusOK, struct {
-								Tasks []codersdk.Task `json:"tasks"`
-								Count int             `json:"count"`
-							}{
-								Tasks: []codersdk.Task{{
-									ID:              uuid.MustParse("11111111-1111-1111-1111-111111111111"),
-									Name:            "exists",
-									OwnerName:       "me",
-									WorkspaceStatus: codersdk.WorkspaceStatusPending,
-									CreatedAt:       now.Add(-5 * time.Second),
-									UpdatedAt:       now.Add(-5 * time.Second),
-									WorkspaceAgentHealth: &codersdk.WorkspaceAgentHealth{
-										Healthy: true,
-									},
-									WorkspaceAgentLifecycle: ptr.Ref(codersdk.WorkspaceAgentLifecycleReady),
-									Status:                  codersdk.TaskStatusPending,
-								}},
-								Count: 1,
-							})
-							return
-						}
+					case "/api/experimental/tasks/me/exists":
+						httpapi.Write(ctx, w, http.StatusOK, codersdk.Task{
+							ID:              uuid.MustParse("11111111-1111-1111-1111-111111111111"),
+							Name:            "exists",
+							OwnerName:       "me",
+							WorkspaceStatus: codersdk.WorkspaceStatusPending,
+							CreatedAt:       now.Add(-5 * time.Second),
+							UpdatedAt:       now.Add(-5 * time.Second),
+							WorkspaceAgentHealth: &codersdk.WorkspaceAgentHealth{
+								Healthy: true,
+							},
+							WorkspaceAgentLifecycle: ptr.Ref(codersdk.WorkspaceAgentLifecycleReady),
+							Status:                  codersdk.TaskStatusPending,
+						})
+						return
 					case "/api/experimental/tasks/me/11111111-1111-1111-1111-111111111111":
 						defer calls.Add(1)
 						switch calls.Load() {
@@ -263,40 +218,18 @@ func Test_TaskStatus(t *testing.T) {
 				ts := time.Date(2025, 8, 26, 12, 34, 56, 0, time.UTC)
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch r.URL.Path {
-					case "/api/experimental/tasks":
-						if r.URL.Query().Get("q") == "owner:\"me\"" {
-							httpapi.Write(ctx, w, http.StatusOK, struct {
-								Tasks []codersdk.Task `json:"tasks"`
-								Count int             `json:"count"`
-							}{
-								Tasks: []codersdk.Task{{
-									ID:              uuid.MustParse("11111111-1111-1111-1111-111111111111"),
-									Name:            "exists",
-									OwnerName:       "me",
-									WorkspaceStatus: codersdk.WorkspaceStatusRunning,
-									CreatedAt:       ts,
-									UpdatedAt:       ts,
-									CurrentState: &codersdk.TaskStateEntry{
-										State:     codersdk.TaskStateWorking,
-										Timestamp: ts.Add(time.Second),
-										Message:   "Thinking furiously...",
-									},
-									WorkspaceAgentHealth: &codersdk.WorkspaceAgentHealth{
-										Healthy: true,
-									},
-									WorkspaceAgentLifecycle: ptr.Ref(codersdk.WorkspaceAgentLifecycleReady),
-									Status:                  codersdk.TaskStatusActive,
-								}},
-								Count: 1,
-							})
-							return
-						}
-					case "/api/experimental/tasks/me/11111111-1111-1111-1111-111111111111":
+					case "/api/experimental/tasks/me/exists":
 						httpapi.Write(ctx, w, http.StatusOK, codersdk.Task{
-							ID:              uuid.MustParse("11111111-1111-1111-1111-111111111111"),
-							WorkspaceStatus: codersdk.WorkspaceStatusRunning,
-							CreatedAt:       ts,
-							UpdatedAt:       ts,
+							ID:        uuid.MustParse("11111111-1111-1111-1111-111111111111"),
+							Name:      "exists",
+							OwnerName: "me",
+							WorkspaceAgentHealth: &codersdk.WorkspaceAgentHealth{
+								Healthy: true,
+							},
+							WorkspaceAgentLifecycle: ptr.Ref(codersdk.WorkspaceAgentLifecycleReady),
+							WorkspaceStatus:         codersdk.WorkspaceStatusRunning,
+							CreatedAt:               ts,
+							UpdatedAt:               ts,
 							CurrentState: &codersdk.TaskStateEntry{
 								State:     codersdk.TaskStateWorking,
 								Timestamp: ts.Add(time.Second),

cli/exp_task_test.go

@@ -53,7 +53,6 @@ func Test_Tasks(t *testing.T) {
 		taskName     = strings.ReplaceAll(testutil.GetRandomName(t), "_", "-")
 	)
 
-	//nolint:paralleltest // The sub-tests of this test must be run sequentially.
 	for _, tc := range []struct {
 		name     string
 		cmdArgs  []string
@@ -135,16 +134,15 @@ func Test_Tasks(t *testing.T) {
 			},
 		},
 	} {
-		t.Run(tc.name, func(t *testing.T) {
-			var stdout strings.Builder
-			inv, root := clitest.New(t, tc.cmdArgs...)
-			inv.Stdout = &stdout
-			clitest.SetupConfig(t, userClient, root)
-			require.NoError(t, inv.WithContext(ctx).Run())
-			if tc.assertFn != nil {
-				tc.assertFn(stdout.String(), userClient)
-			}
-		})
+		t.Logf("test case: %q", tc.name)
+		var stdout strings.Builder
+		inv, root := clitest.New(t, tc.cmdArgs...)
+		inv.Stdout = &stdout
+		clitest.SetupConfig(t, userClient, root)
+		require.NoError(t, inv.WithContext(ctx).Run(), tc.name)
+		if tc.assertFn != nil {
+			tc.assertFn(stdout.String(), userClient)
+		}
 	}
 }
 
@@ -293,7 +291,6 @@ func createAITaskTemplate(t *testing.T, client *codersdk.Client, orgID uuid.UUID
 			{
 				Type: &proto.Response_Plan{
 					Plan: &proto.PlanComplete{
-						Parameters: []*proto.RichParameter{{Name: codersdk.AITaskPromptParameterName, Type: "string"}},
 						HasAiTasks: true,
 					},
 				},
@@ -328,9 +325,7 @@ func createAITaskTemplate(t *testing.T, client *codersdk.Client, orgID uuid.UUID
 						},
 						AiTasks: []*proto.AITask{
 							{
-								SidebarApp: &proto.AITaskSidebarApp{
-									Id: taskAppID.String(),
-								},
+								AppId: taskAppID.String(),
 							},
 						},
 					},

cli/keyring_test.go

@@ -0,0 +1,355 @@
+package cli_test
+
+import (
+	"bytes"
+	"net/url"
+	"os"
+	"path"
+	"runtime"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/cli"
+	"github.com/coder/coder/v2/cli/clitest"
+	"github.com/coder/coder/v2/coderd/coderdtest"
+	"github.com/coder/coder/v2/pty/ptytest"
+)
+
+// mockKeyring is a mock sessionstore.Backend implementation.
+type mockKeyring struct {
+	credentials map[string]string // service name -> credential
+}
+
+const mockServiceName = "mock-service-name"
+
+func newMockKeyring() *mockKeyring {
+	return &mockKeyring{credentials: make(map[string]string)}
+}
+
+func (m *mockKeyring) Read(_ *url.URL) (string, error) {
+	cred, ok := m.credentials[mockServiceName]
+	if !ok {
+		return "", os.ErrNotExist
+	}
+	return cred, nil
+}
+
+func (m *mockKeyring) Write(_ *url.URL, token string) error {
+	m.credentials[mockServiceName] = token
+	return nil
+}
+
+func (m *mockKeyring) Delete(_ *url.URL) error {
+	_, ok := m.credentials[mockServiceName]
+	if !ok {
+		return os.ErrNotExist
+	}
+	delete(m.credentials, mockServiceName)
+	return nil
+}
+
+func TestUseKeyring(t *testing.T) {
+	// Verify that the --use-keyring flag opts into using a keyring backend for
+	// storing session tokens instead of plain text files.
+	t.Parallel()
+
+	t.Run("Login", func(t *testing.T) {
+		t.Parallel()
+
+		// Create a test server
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+
+		// Create a pty for interactive prompts
+		pty := ptytest.New(t)
+
+		// Create CLI invocation with --use-keyring flag
+		inv, cfg := clitest.New(t,
+			"login",
+			"--force-tty",
+			"--use-keyring",
+			"--no-open",
+			client.URL.String(),
+		)
+		inv.Stdin = pty.Input()
+		inv.Stdout = pty.Output()
+
+		// Inject the mock backend before running the command
+		var root cli.RootCmd
+		cmd, err := root.Command(root.AGPL())
+		require.NoError(t, err)
+		mockBackend := newMockKeyring()
+		root.WithSessionStorageBackend(mockBackend)
+		inv.Command = cmd
+
+		// Run login in background
+		doneChan := make(chan struct{})
+		go func() {
+			defer close(doneChan)
+			err := inv.Run()
+			assert.NoError(t, err)
+		}()
+
+		// Provide the token when prompted
+		pty.ExpectMatch("Paste your token here:")
+		pty.WriteLine(client.SessionToken())
+		pty.ExpectMatch("Welcome to Coder")
+		<-doneChan
+
+		// Verify that session file was NOT created (using keyring instead)
+		sessionFile := path.Join(string(cfg), "session")
+		_, err = os.Stat(sessionFile)
+		require.True(t, os.IsNotExist(err), "session file should not exist when using keyring")
+
+		// Verify that the credential IS stored in mock keyring
+		cred, err := mockBackend.Read(nil)
+		require.NoError(t, err, "credential should be stored in mock keyring")
+		require.Equal(t, client.SessionToken(), cred, "stored token should match login token")
+	})
+
+	t.Run("Logout", func(t *testing.T) {
+		t.Parallel()
+
+		// Create a test server
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+
+		// Create a pty for interactive prompts
+		pty := ptytest.New(t)
+
+		// First, login with --use-keyring
+		loginInv, cfg := clitest.New(t,
+			"login",
+			"--force-tty",
+			"--use-keyring",
+			"--no-open",
+			client.URL.String(),
+		)
+		loginInv.Stdin = pty.Input()
+		loginInv.Stdout = pty.Output()
+
+		// Inject the mock backend
+		var loginRoot cli.RootCmd
+		loginCmd, err := loginRoot.Command(loginRoot.AGPL())
+		require.NoError(t, err)
+		mockBackend := newMockKeyring()
+		loginRoot.WithSessionStorageBackend(mockBackend)
+		loginInv.Command = loginCmd
+
+		doneChan := make(chan struct{})
+		go func() {
+			defer close(doneChan)
+			err := loginInv.Run()
+			assert.NoError(t, err)
+		}()
+
+		pty.ExpectMatch("Paste your token here:")
+		pty.WriteLine(client.SessionToken())
+		pty.ExpectMatch("Welcome to Coder")
+		<-doneChan
+
+		// Verify credential exists in mock keyring
+		cred, err := mockBackend.Read(nil)
+		require.NoError(t, err, "read credential should succeed before logout")
+		require.NotEmpty(t, cred, "credential should exist after logout")
+
+		// Now run logout with --use-keyring
+		logoutInv, _ := clitest.New(t,
+			"logout",
+			"--use-keyring",
+			"--yes",
+			"--global-config", string(cfg),
+		)
+
+		// Inject the same mock backend
+		var logoutRoot cli.RootCmd
+		logoutCmd, err := logoutRoot.Command(logoutRoot.AGPL())
+		require.NoError(t, err)
+		logoutRoot.WithSessionStorageBackend(mockBackend)
+		logoutInv.Command = logoutCmd
+
+		var logoutOut bytes.Buffer
+		logoutInv.Stdout = &logoutOut
+
+		err = logoutInv.Run()
+		require.NoError(t, err, "logout should succeed")
+
+		// Verify the credential was deleted from mock keyring
+		_, err = mockBackend.Read(nil)
+		require.ErrorIs(t, err, os.ErrNotExist, "credential should be deleted from keyring after logout")
+	})
+
+	t.Run("OmitFlag", func(t *testing.T) {
+		t.Parallel()
+
+		// Create a test server
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+
+		// Create a pty for interactive prompts
+		pty := ptytest.New(t)
+
+		// --use-keyring flag omitted (should use file-based storage)
+		inv, cfg := clitest.New(t,
+			"login",
+			"--force-tty",
+			"--no-open",
+			client.URL.String(),
+		)
+		inv.Stdin = pty.Input()
+		inv.Stdout = pty.Output()
+
+		doneChan := make(chan struct{})
+		go func() {
+			defer close(doneChan)
+			err := inv.Run()
+			assert.NoError(t, err)
+		}()
+
+		pty.ExpectMatch("Paste your token here:")
+		pty.WriteLine(client.SessionToken())
+		pty.ExpectMatch("Welcome to Coder")
+		<-doneChan
+
+		// Verify that session file WAS created (not using keyring)
+		sessionFile := path.Join(string(cfg), "session")
+		_, err := os.Stat(sessionFile)
+		require.NoError(t, err, "session file should exist when NOT using --use-keyring")
+
+		// Read and verify the token from file
+		content, err := os.ReadFile(sessionFile)
+		require.NoError(t, err, "should be able to read session file")
+		require.Equal(t, client.SessionToken(), string(content), "file should contain the session token")
+	})
+
+	t.Run("EnvironmentVariable", func(t *testing.T) {
+		t.Parallel()
+
+		// Create a test server
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+
+		// Create a pty for interactive prompts
+		pty := ptytest.New(t)
+
+		// Login using CODER_USE_KEYRING environment variable instead of flag
+		inv, cfg := clitest.New(t,
+			"login",
+			"--force-tty",
+			"--no-open",
+			client.URL.String(),
+		)
+		inv.Stdin = pty.Input()
+		inv.Stdout = pty.Output()
+		inv.Environ.Set("CODER_USE_KEYRING", "true")
+
+		// Inject the mock backend
+		var root cli.RootCmd
+		cmd, err := root.Command(root.AGPL())
+		require.NoError(t, err)
+		mockBackend := newMockKeyring()
+		root.WithSessionStorageBackend(mockBackend)
+		inv.Command = cmd
+
+		doneChan := make(chan struct{})
+		go func() {
+			defer close(doneChan)
+			err := inv.Run()
+			assert.NoError(t, err)
+		}()
+
+		pty.ExpectMatch("Paste your token here:")
+		pty.WriteLine(client.SessionToken())
+		pty.ExpectMatch("Welcome to Coder")
+		<-doneChan
+
+		// Verify that session file was NOT created (using keyring via env var)
+		sessionFile := path.Join(string(cfg), "session")
+		_, err = os.Stat(sessionFile)
+		require.True(t, os.IsNotExist(err), "session file should not exist when using keyring via env var")
+
+		// Verify credential is in mock keyring
+		cred, err := mockBackend.Read(nil)
+		require.NoError(t, err, "credential should be stored in keyring when CODER_USE_KEYRING=true")
+		require.NotEmpty(t, cred)
+	})
+}
+
+func TestUseKeyringUnsupportedOS(t *testing.T) {
+	// Verify that trying to use --use-keyring on an unsupported operating system produces
+	// a helpful error message.
+	t.Parallel()
+
+	// Only run this on an unsupported OS.
+	if runtime.GOOS == "windows" || runtime.GOOS == "darwin" {
+		t.Skipf("Skipping unsupported OS test on %s where keyring is supported", runtime.GOOS)
+	}
+
+	const expMessage = "keyring storage is not supported on this operating system; remove the --use-keyring flag"
+
+	t.Run("LoginWithUnsupportedKeyring", func(t *testing.T) {
+		t.Parallel()
+
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+
+		// Try to login with --use-keyring on an unsupported OS
+		inv, _ := clitest.New(t,
+			"login",
+			"--use-keyring",
+			client.URL.String(),
+		)
+
+		// The error should occur immediately, before any prompts
+		loginErr := inv.Run()
+
+		// Verify we got an error about unsupported OS
+		require.Error(t, loginErr)
+		require.Contains(t, loginErr.Error(), expMessage)
+	})
+
+	t.Run("LogoutWithUnsupportedKeyring", func(t *testing.T) {
+		t.Parallel()
+
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+		pty := ptytest.New(t)
+
+		// First login without keyring to create a session
+		loginInv, cfg := clitest.New(t,
+			"login",
+			"--force-tty",
+			"--no-open",
+			client.URL.String(),
+		)
+		loginInv.Stdin = pty.Input()
+		loginInv.Stdout = pty.Output()
+
+		doneChan := make(chan struct{})
+		go func() {
+			defer close(doneChan)
+			err := loginInv.Run()
+			assert.NoError(t, err)
+		}()
+
+		pty.ExpectMatch("Paste your token here:")
+		pty.WriteLine(client.SessionToken())
+		pty.ExpectMatch("Welcome to Coder")
+		<-doneChan
+
+		// Now try to logout with --use-keyring on an unsupported OS
+		logoutInv, _ := clitest.New(t,
+			"logout",
+			"--use-keyring",
+			"--yes",
+			"--global-config", string(cfg),
+		)
+
+		err := logoutInv.Run()
+		// Verify we got an error about unsupported OS
+		require.Error(t, err)
+		require.Contains(t, err.Error(), expMessage)
+	})
+}

cli/login.go

@@ -19,6 +19,7 @@ import (
 	"github.com/coder/pretty"
 
 	"github.com/coder/coder/v2/cli/cliui"
+	"github.com/coder/coder/v2/cli/sessionstore"
 	"github.com/coder/coder/v2/coderd/userpassword"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/serpent"
@@ -114,9 +115,11 @@ func (r *RootCmd) loginWithPassword(
 	}
 
 	sessionToken := resp.SessionToken
-	config := r.createConfig()
-	err = config.Session().Write(sessionToken)
+	err = r.ensureTokenBackend().Write(client.URL, sessionToken)
 	if err != nil {
+		if xerrors.Is(err, sessionstore.ErrNotImplemented) {
+			return errKeyringNotSupported
+		}
 		return xerrors.Errorf("write session token: %w", err)
 	}
 
@@ -149,11 +152,15 @@ func (r *RootCmd) login() *serpent.Command {
 		useTokenForSession bool
 	)
 	cmd := &serpent.Command{
-		Use:        "login [<url>]",
-		Short:      "Authenticate with Coder deployment",
+		Use:   "login [<url>]",
+		Short: "Authenticate with Coder deployment",
+		Long: "By default, the session token is stored in a plain text file. Use the " +
+			"--use-keyring flag or set CODER_USE_KEYRING=true to store the token in " +
+			"the operating system keyring instead.",
 		Middleware: serpent.RequireRangeArgs(0, 1),
 		Handler: func(inv *serpent.Invocation) error {
 			ctx := inv.Context()
+
 			rawURL := ""
 			var urlSource string
 
@@ -198,6 +205,15 @@ func (r *RootCmd) login() *serpent.Command {
 				return err
 			}
 
+			// Check keyring availability before prompting the user for a token to fail fast.
+			if r.useKeyring {
+				backend := r.ensureTokenBackend()
+				_, err := backend.Read(client.URL)
+				if err != nil && xerrors.Is(err, sessionstore.ErrNotImplemented) {
+					return errKeyringNotSupported
+				}
+			}
+
 			hasFirstUser, err := client.HasFirstUser(ctx)
 			if err != nil {
 				return xerrors.Errorf("Failed to check server %q for first user, is the URL correct and is coder accessible from your browser? Error - has initial user: %w", serverURL.String(), err)
@@ -394,8 +410,11 @@ func (r *RootCmd) login() *serpent.Command {
 			}
 
 			config := r.createConfig()
-			err = config.Session().Write(sessionToken)
+			err = r.ensureTokenBackend().Write(client.URL, sessionToken)
 			if err != nil {
+				if xerrors.Is(err, sessionstore.ErrNotImplemented) {
+					return errKeyringNotSupported
+				}
 				return xerrors.Errorf("write session token: %w", err)
 			}
 			err = config.URL().Write(serverURL.String())

cli/logout.go

@@ -8,6 +8,7 @@ import (
 	"golang.org/x/xerrors"
 
 	"github.com/coder/coder/v2/cli/cliui"
+	"github.com/coder/coder/v2/cli/sessionstore"
 	"github.com/coder/serpent"
 )
 
@@ -46,11 +47,15 @@ func (r *RootCmd) logout() *serpent.Command {
 				errors = append(errors, xerrors.Errorf("remove URL file: %w", err))
 			}
 
-			err = config.Session().Delete()
+			err = r.ensureTokenBackend().Delete(client.URL)
 			// Only throw error if the session configuration file is present,
 			// otherwise the user is already logged out, and we proceed
-			if err != nil && !os.IsNotExist(err) {
-				errors = append(errors, xerrors.Errorf("remove session file: %w", err))
+			if err != nil && !xerrors.Is(err, os.ErrNotExist) {
+				if xerrors.Is(err, sessionstore.ErrNotImplemented) {
+					errors = append(errors, errKeyringNotSupported)
+				} else {
+					errors = append(errors, xerrors.Errorf("remove session token: %w", err))
+				}
 			}
 
 			err = config.Organization().Delete()

cli/root.go

@@ -37,6 +37,7 @@ import (
 	"github.com/coder/coder/v2/cli/cliui"
 	"github.com/coder/coder/v2/cli/config"
 	"github.com/coder/coder/v2/cli/gitauth"
+	"github.com/coder/coder/v2/cli/sessionstore"
 	"github.com/coder/coder/v2/cli/telemetry"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/codersdk/agentsdk"
@@ -54,6 +55,8 @@ var (
 	// ErrSilent is a sentinel error that tells the command handler to just exit with a non-zero error, but not print
 	// anything.
 	ErrSilent = xerrors.New("silent error")
+
+	errKeyringNotSupported = xerrors.New("keyring storage is not supported on this operating system; remove the --use-keyring flag to use file-based storage")
 )
 
 const (
@@ -68,12 +71,14 @@ const (
 	varVerbose                 = "verbose"
 	varDisableDirect           = "disable-direct-connections"
 	varDisableNetworkTelemetry = "disable-network-telemetry"
+	varUseKeyring              = "use-keyring"
 
 	notLoggedInMessage = "You are not logged in. Try logging in using '%s login <url>'."
 
 	envNoVersionCheck   = "CODER_NO_VERSION_WARNING"
 	envNoFeatureWarning = "CODER_NO_FEATURE_WARNING"
 	envSessionToken     = "CODER_SESSION_TOKEN"
+	envUseKeyring       = "CODER_USE_KEYRING"
 	//nolint:gosec
 	envAgentToken = "CODER_AGENT_TOKEN"
 	//nolint:gosec
@@ -474,6 +479,15 @@ func (r *RootCmd) Command(subcommands []*serpent.Command) (*serpent.Command, err
 			Value:       serpent.BoolOf(&r.disableNetworkTelemetry),
 			Group:       globalGroup,
 		},
+		{
+			Flag: varUseKeyring,
+			Env:  envUseKeyring,
+			Description: "Store and retrieve session tokens using the operating system " +
+				"keyring. Currently only supported on Windows. By default, tokens are " +
+				"stored in plain text files.",
+			Value: serpent.BoolOf(&r.useKeyring),
+			Group: globalGroup,
+		},
 		{
 			Flag:        "debug-http",
 			Description: "Debug codersdk HTTP requests.",
@@ -508,6 +522,7 @@ func (r *RootCmd) Command(subcommands []*serpent.Command) (*serpent.Command, err
 type RootCmd struct {
 	clientURL     *url.URL
 	token         string
+	tokenBackend  sessionstore.Backend
 	globalConfig  string
 	header        []string
 	headerCommand string
@@ -522,6 +537,7 @@ type RootCmd struct {
 	disableNetworkTelemetry bool
 	noVersionCheck          bool
 	noFeatureWarning        bool
+	useKeyring              bool
 }
 
 // InitClient creates and configures a new client with authentication, telemetry,
@@ -549,14 +565,19 @@ func (r *RootCmd) InitClient(inv *serpent.Invocation) (*codersdk.Client, error)
 			return nil, err
 		}
 	}
-	// Read the token stored on disk.
 	if r.token == "" {
-		r.token, err = conf.Session().Read()
+		tok, err := r.ensureTokenBackend().Read(r.clientURL)
 		// Even if there isn't a token, we don't care.
 		// Some API routes can be unauthenticated.
-		if err != nil && !os.IsNotExist(err) {
+		if err != nil && !xerrors.Is(err, os.ErrNotExist) {
+			if xerrors.Is(err, sessionstore.ErrNotImplemented) {
+				return nil, errKeyringNotSupported
+			}
 			return nil, err
 		}
+		if tok != "" {
+			r.token = tok
+		}
 	}
 
 	// Configure HTTP client with transport wrappers
@@ -588,7 +609,6 @@ func (r *RootCmd) InitClient(inv *serpent.Invocation) (*codersdk.Client, error)
 // This allows commands to run without requiring authentication, but still use auth if available.
 func (r *RootCmd) TryInitClient(inv *serpent.Invocation) (*codersdk.Client, error) {
 	conf := r.createConfig()
-	var err error
 	// Read the client URL stored on disk.
 	if r.clientURL == nil || r.clientURL.String() == "" {
 		rawURL, err := conf.URL().Read()
@@ -605,14 +625,19 @@ func (r *RootCmd) TryInitClient(inv *serpent.Invocation) (*codersdk.Client, erro
 			}
 		}
 	}
-	// Read the token stored on disk.
 	if r.token == "" {
-		r.token, err = conf.Session().Read()
+		tok, err := r.ensureTokenBackend().Read(r.clientURL)
 		// Even if there isn't a token, we don't care.
 		// Some API routes can be unauthenticated.
-		if err != nil && !os.IsNotExist(err) {
+		if err != nil && !xerrors.Is(err, os.ErrNotExist) {
+			if xerrors.Is(err, sessionstore.ErrNotImplemented) {
+				return nil, errKeyringNotSupported
+			}
 			return nil, err
 		}
+		if tok != "" {
+			r.token = tok
+		}
 	}
 
 	// Only configure the client if we have a URL
@@ -688,6 +713,24 @@ func (r *RootCmd) createUnauthenticatedClient(ctx context.Context, serverURL *ur
 	return client, nil
 }
 
+// ensureTokenBackend returns the session token storage backend, creating it if necessary.
+// This must be called after flags are parsed so we can respect the value of the --use-keyring
+// flag.
+func (r *RootCmd) ensureTokenBackend() sessionstore.Backend {
+	if r.tokenBackend == nil {
+		if r.useKeyring {
+			r.tokenBackend = sessionstore.NewKeyring()
+		} else {
+			r.tokenBackend = sessionstore.NewFile(r.createConfig)
+		}
+	}
+	return r.tokenBackend
+}
+
+func (r *RootCmd) WithSessionStorageBackend(backend sessionstore.Backend) {
+	r.tokenBackend = backend
+}
+
 type AgentAuth struct {
 	// Agent Client config
 	agentToken     string

cli/server.go

@@ -1029,7 +1029,7 @@ 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, quartz.NewReal())
+			purger := dbpurge.New(ctx, logger.Named("dbpurge"), options.Database, options.DeploymentValues, quartz.NewReal())
 			defer purger.Close()
 
 			// Updates workspace usage
@@ -1476,6 +1476,7 @@ func newProvisionerDaemon(
 						Listener:      terraformServer,
 						Logger:        provisionerLogger,
 						WorkDirectory: workDir,
+						Experiments:   coderAPI.Experiments,
 					},
 					CachePath: tfDir,
 					Tracer:    tracer,
@@ -2142,21 +2143,33 @@ func startBuiltinPostgres(ctx context.Context, cfg config.Root, logger slog.Logg
 	}
 	stdlibLogger := slog.Stdlib(ctx, logger.Named("postgres"), slog.LevelDebug)
 
-	// If the port is not defined, an available port will be found dynamically.
+	// If the port is not defined, an available port will be found dynamically. This has
+	// implications in CI because here is no way to tell Postgres to use an ephemeral
+	// port, so to avoid flaky tests in CI we need to retry EmbeddedPostgres.Start in
+	// case of a race condition where the port we quickly listen on and close in
+	// embeddedPostgresURL() is not free by the time the embedded postgres starts up.
+	// The maximum retry attempts _should_ cover most cases where port conflicts occur
+	// in CI and cause flaky tests.
 	maxAttempts := 1
 	_, err = cfg.PostgresPort().Read()
+	// Important: if retryPortDiscovery is changed to not include testing.Testing(),
+	// the retry logic below also needs to be updated to ensure we don't delete an
+	// existing database
 	retryPortDiscovery := errors.Is(err, os.ErrNotExist) && testing.Testing()
 	if retryPortDiscovery {
-		// There is no way to tell Postgres to use an ephemeral port, so in order to avoid
-		// flaky tests in CI we need to retry EmbeddedPostgres.Start in case of a race
-		// condition where the port we quickly listen on and close in embeddedPostgresURL()
-		// is not free by the time the embedded postgres starts up. This maximum_should
-		// cover most cases where port conflicts occur in CI and cause flaky tests.
 		maxAttempts = 3
 	}
 
 	var startErr error
 	for attempt := 0; attempt < maxAttempts; attempt++ {
+		if retryPortDiscovery && attempt > 0 {
+			// Clean up the data and runtime directories and the port file from the
+			// previous failed attempt to ensure a clean slate for the next attempt.
+			_ = os.RemoveAll(filepath.Join(cfg.PostgresPath(), "data"))
+			_ = os.RemoveAll(filepath.Join(cfg.PostgresPath(), "runtime"))
+			_ = cfg.PostgresPort().Delete()
+		}
+
 		// Ensure a password and port have been generated.
 		connectionURL, err := embeddedPostgresURL(cfg)
 		if err != nil {
@@ -2203,11 +2216,6 @@ func startBuiltinPostgres(ctx context.Context, cfg config.Root, logger slog.Logg
 			slog.F("port", pgPort),
 			slog.Error(startErr),
 		)
-
-		if retryPortDiscovery {
-			// Since a retry is needed, we wipe the port stored here at the beginning of the loop.
-			_ = cfg.PostgresPort().Delete()
-		}
 	}
 
 	return "", nil, xerrors.Errorf("failed to start built-in PostgreSQL after %d attempts. "+

cli/sessionstore/sessionstore.go

@@ -0,0 +1,245 @@
+// Package sessionstore provides CLI session token storage mechanisms.
+// Operating system keyring storage is intended to have compatibility with other Coder
+// applications (e.g. Coder Desktop, Coder provider for JetBrains Toolbox, etc) so that
+// applications can read/write the same credential stored in the keyring.
+//
+// Note that we aren't using an existing Go package zalando/go-keyring here for a few
+// reasons. 1) It prescribes the format of the target credential name in the OS keyrings,
+// which makes our life difficult for compatibility with other Coder applications. 2)
+// It uses init functions that make it difficult to test with. As a result, the OS
+// keyring implementations may be adapted from zalando/go-keyring source (i.e. Windows).
+package sessionstore
+
+import (
+	"encoding/json"
+	"errors"
+	"net/url"
+	"os"
+	"strings"
+
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/cli/config"
+)
+
+// Backend is a storage backend for session tokens.
+type Backend interface {
+	// Read returns the session token for the given server URL or an error, if any. It
+	// will return os.ErrNotExist if no token exists for the given URL.
+	Read(serverURL *url.URL) (string, error)
+	// Write stores the session token for the given server URL.
+	Write(serverURL *url.URL, token string) error
+	// Delete removes the session token for the given server URL or an error, if any.
+	// It will return os.ErrNotExist error if no token exists to delete.
+	Delete(serverURL *url.URL) error
+}
+
+var (
+
+	// ErrSetDataTooBig is returned if `keyringProvider.Set` was called with too much data.
+	// On macOS: The combination of service, username & password should not exceed ~3000 bytes
+	// On Windows: The service is limited to 32KiB while the password is limited to 2560 bytes
+	ErrSetDataTooBig = xerrors.New("data passed to Set was too big")
+
+	// ErrNotImplemented represents when keyring usage is not implemented on the current
+	// operating system.
+	ErrNotImplemented = xerrors.New("not implemented")
+)
+
+const (
+	// defaultServiceName is the service name used in keyrings  for storing Coder CLI session
+	// tokens.
+	defaultServiceName = "coder-v2-credentials"
+)
+
+// keyringProvider represents an operating system keyring. The expectation
+// is these methods operate on the user/login keyring.
+type keyringProvider interface {
+	// Set stores the given credential for a service name in the operating system
+	// keyring.
+	Set(service, credential string) error
+	// Get retrieves the credential from the keyring. It must return os.ErrNotExist
+	// if the credential is not found.
+	Get(service string) ([]byte, error)
+	// Delete deletes the credential from the keyring. It must return os.ErrNotExist
+	// if the credential is not found.
+	Delete(service string) error
+}
+
+// credential represents a single credential entry.
+type credential struct {
+	CoderURL string `json:"coder_url"`
+	APIToken string `json:"api_token"`
+}
+
+// credentialsMap represents the JSON structure stored in the operating system keyring.
+// It supports storing multiple credentials for different server URLs.
+type credentialsMap map[string]credential
+
+// normalizeHost returns a normalized version of the URL host for use as a map key.
+func normalizeHost(u *url.URL) (string, error) {
+	if u == nil || u.Host == "" {
+		return "", xerrors.New("nil server URL")
+	}
+	return strings.TrimSpace(strings.ToLower(u.Host)), nil
+}
+
+// parseCredentialsJSON parses the JSON from the keyring into a credentialsMap.
+func parseCredentialsJSON(jsonData []byte) (credentialsMap, error) {
+	if len(jsonData) == 0 {
+		return make(credentialsMap), nil
+	}
+
+	var creds credentialsMap
+	if err := json.Unmarshal(jsonData, &creds); err != nil {
+		return nil, xerrors.Errorf("unmarshal credentials: %w", err)
+	}
+
+	return creds, nil
+}
+
+// Keyring is a Backend that exclusively stores the session token in the operating
+// system keyring. Happy path usage of this type should start with NewKeyring.
+// It stores a JSON object in the keyring that supports multiple credentials for
+// different server URLs, providing compatibility with Coder Desktop and other Coder
+// applications.
+type Keyring struct {
+	provider    keyringProvider
+	serviceName string
+}
+
+// NewKeyring creates a Keyring with the default service name for production use.
+func NewKeyring() Keyring {
+	return Keyring{
+		provider:    operatingSystemKeyring{},
+		serviceName: defaultServiceName,
+	}
+}
+
+// NewKeyringWithService creates a Keyring Backend that stores credentials under the
+// specified service name. This is primarily intended for testing to avoid conflicts
+// with production credentials and collisions between tests.
+func NewKeyringWithService(serviceName string) Keyring {
+	return Keyring{
+		provider:    operatingSystemKeyring{},
+		serviceName: serviceName,
+	}
+}
+
+func (o Keyring) Read(serverURL *url.URL) (string, error) {
+	host, err := normalizeHost(serverURL)
+	if err != nil {
+		return "", err
+	}
+
+	credJSON, err := o.provider.Get(o.serviceName)
+	if err != nil {
+		return "", err
+	}
+	if len(credJSON) == 0 {
+		return "", os.ErrNotExist
+	}
+
+	creds, err := parseCredentialsJSON(credJSON)
+	if err != nil {
+		return "", xerrors.Errorf("read: parse existing credentials: %w", err)
+	}
+
+	// Return the credential for the specified URL
+	cred, ok := creds[host]
+	if !ok {
+		return "", os.ErrNotExist
+	}
+	return cred.APIToken, nil
+}
+
+func (o Keyring) Write(serverURL *url.URL, token string) error {
+	host, err := normalizeHost(serverURL)
+	if err != nil {
+		return err
+	}
+
+	existingJSON, err := o.provider.Get(o.serviceName)
+	if err != nil && !errors.Is(err, os.ErrNotExist) {
+		return xerrors.Errorf("read existing credentials: %w", err)
+	}
+
+	creds, err := parseCredentialsJSON(existingJSON)
+	if err != nil {
+		return xerrors.Errorf("write: parse existing credentials: %w", err)
+	}
+
+	// Upsert the credential for this URL.
+	creds[host] = credential{
+		CoderURL: host,
+		APIToken: token,
+	}
+
+	credsJSON, err := json.Marshal(creds)
+	if err != nil {
+		return xerrors.Errorf("marshal credentials: %w", err)
+	}
+
+	err = o.provider.Set(o.serviceName, string(credsJSON))
+	if err != nil {
+		return xerrors.Errorf("write credentials to keyring: %w", err)
+	}
+	return nil
+}
+
+func (o Keyring) Delete(serverURL *url.URL) error {
+	host, err := normalizeHost(serverURL)
+	if err != nil {
+		return err
+	}
+
+	existingJSON, err := o.provider.Get(o.serviceName)
+	if err != nil {
+		return err
+	}
+
+	creds, err := parseCredentialsJSON(existingJSON)
+	if err != nil {
+		return xerrors.Errorf("failed to parse existing credentials: %w", err)
+	}
+
+	if _, ok := creds[host]; !ok {
+		return os.ErrNotExist
+	}
+
+	delete(creds, host)
+
+	// Delete the entire keyring entry when no credentials remain.
+	if len(creds) == 0 {
+		return o.provider.Delete(o.serviceName)
+	}
+
+	// Write back the updated credentials map.
+	credsJSON, err := json.Marshal(creds)
+	if err != nil {
+		return xerrors.Errorf("failed to marshal credentials: %w", err)
+	}
+
+	return o.provider.Set(o.serviceName, string(credsJSON))
+}
+
+// File is a Backend that exclusively stores the session token in a file on disk.
+type File struct {
+	config func() config.Root
+}
+
+func NewFile(f func() config.Root) *File {
+	return &File{config: f}
+}
+
+func (f *File) Read(_ *url.URL) (string, error) {
+	return f.config().Session().Read()
+}
+
+func (f *File) Write(_ *url.URL, token string) error {
+	return f.config().Session().Write(token)
+}
+
+func (f *File) Delete(_ *url.URL) error {
+	return f.config().Session().Delete()
+}

cli/sessionstore/sessionstore_darwin.go

@@ -0,0 +1,105 @@
+//go:build darwin
+
+package sessionstore
+
+import (
+	"encoding/base64"
+	"fmt"
+	"io"
+	"os"
+	"os/exec"
+	"regexp"
+	"strings"
+)
+
+const (
+	// fixedUsername is the fixed username used for all keychain entries.
+	// Since our interface only uses service names, we use a constant username.
+	fixedUsername = "coder-login-credentials"
+
+	execPathKeychain = "/usr/bin/security"
+	notFoundStr      = "could not be found"
+)
+
+// operatingSystemKeyring implements keyringProvider for macOS.
+// It is largely adapted from the zalando/go-keyring package.
+type operatingSystemKeyring struct{}
+
+func (operatingSystemKeyring) Set(service, credential string) error {
+	// if the added secret has multiple lines or some non ascii,
+	// macOS will hex encode it on return. To avoid getting garbage, we
+	// encode all passwords
+	password := base64.StdEncoding.EncodeToString([]byte(credential))
+
+	cmd := exec.Command(execPathKeychain, "-i")
+	stdIn, err := cmd.StdinPipe()
+	if err != nil {
+		return err
+	}
+
+	if err = cmd.Start(); err != nil {
+		return err
+	}
+
+	command := fmt.Sprintf("add-generic-password -U -s %s -a %s -w %s\n",
+		shellEscape(service),
+		shellEscape(fixedUsername),
+		shellEscape(password))
+	if len(command) > 4096 {
+		return ErrSetDataTooBig
+	}
+
+	if _, err := io.WriteString(stdIn, command); err != nil {
+		return err
+	}
+
+	if err = stdIn.Close(); err != nil {
+		return err
+	}
+
+	return cmd.Wait()
+}
+
+func (operatingSystemKeyring) Get(service string) ([]byte, error) {
+	out, err := exec.Command(
+		execPathKeychain,
+		"find-generic-password",
+		"-s", service,
+		"-wa", fixedUsername).CombinedOutput()
+	if err != nil {
+		if strings.Contains(string(out), notFoundStr) {
+			return nil, os.ErrNotExist
+		}
+		return nil, err
+	}
+
+	trimStr := strings.TrimSpace(string(out))
+	return base64.StdEncoding.DecodeString(trimStr)
+}
+
+func (operatingSystemKeyring) Delete(service string) error {
+	out, err := exec.Command(
+		execPathKeychain,
+		"delete-generic-password",
+		"-s", service,
+		"-a", fixedUsername).CombinedOutput()
+	if strings.Contains(string(out), notFoundStr) {
+		return os.ErrNotExist
+	}
+	return err
+}
+
+// shellEscape returns a shell-escaped version of the string s.
+// This is adapted from github.com/zalando/go-keyring/internal/shellescape.
+func shellEscape(s string) string {
+	if len(s) == 0 {
+		return "''"
+	}
+
+	pattern := regexp.MustCompile(`[^\w@%+=:,./-]`)
+	if pattern.MatchString(s) {
+		return "'" + strings.ReplaceAll(s, "'", "'\"'\"'") + "'"
+	}
+
+	return s
+}

cli/sessionstore/sessionstore_darwin_test.go

@@ -0,0 +1,34 @@
+//go:build darwin
+
+package sessionstore_test
+
+import (
+	"encoding/base64"
+	"os/exec"
+	"testing"
+)
+
+const (
+	execPathKeychain = "/usr/bin/security"
+	fixedUsername    = "coder-login-credentials"
+)
+
+func readRawKeychainCredential(t *testing.T, service string) []byte {
+	t.Helper()
+
+	out, err := exec.Command(
+		execPathKeychain,
+		"find-generic-password",
+		"-s", service,
+		"-wa", fixedUsername).CombinedOutput()
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	dst := make([]byte, base64.StdEncoding.DecodedLen(len(out)))
+	n, err := base64.StdEncoding.Decode(dst, out)
+	if err != nil {
+		t.Fatal(err)
+	}
+	return dst[:n]
+}

cli/sessionstore/sessionstore_internal_test.go

@@ -0,0 +1,121 @@
+package sessionstore
+
+import (
+	"encoding/json"
+	"net/url"
+	"testing"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestNormalizeHost(t *testing.T) {
+	t.Parallel()
+
+	tests := []struct {
+		name    string
+		url     *url.URL
+		want    string
+		wantErr bool
+	}{
+		{
+			name: "StandardHost",
+			url:  &url.URL{Host: "coder.example.com"},
+			want: "coder.example.com",
+		},
+		{
+			name: "HostWithPort",
+			url:  &url.URL{Host: "coder.example.com:8080"},
+			want: "coder.example.com:8080",
+		},
+		{
+			name: "UppercaseHost",
+			url:  &url.URL{Host: "CODER.EXAMPLE.COM"},
+			want: "coder.example.com",
+		},
+		{
+			name: "HostWithWhitespace",
+			url:  &url.URL{Host: "  coder.example.com  "},
+			want: "coder.example.com",
+		},
+		{
+			name:    "NilURL",
+			url:     nil,
+			want:    "",
+			wantErr: true,
+		},
+		{
+			name:    "EmptyHost",
+			url:     &url.URL{Host: ""},
+			want:    "",
+			wantErr: true,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			t.Parallel()
+			got, err := normalizeHost(tt.url)
+			if tt.wantErr {
+				require.Error(t, err)
+				return
+			}
+			require.NoError(t, err)
+			require.Equal(t, tt.want, got)
+		})
+	}
+}
+
+func TestParseCredentialsJSON(t *testing.T) {
+	t.Parallel()
+
+	t.Run("Empty", func(t *testing.T) {
+		t.Parallel()
+		creds, err := parseCredentialsJSON(nil)
+		require.NoError(t, err)
+		require.NotNil(t, creds)
+		require.Empty(t, creds)
+	})
+
+	t.Run("NewFormat", func(t *testing.T) {
+		t.Parallel()
+		jsonData := []byte(`{
+			"coder1.example.com": {"coder_url": "coder1.example.com", "api_token": "token1"},
+			"coder2.example.com": {"coder_url": "coder2.example.com", "api_token": "token2"}
+		}`)
+		creds, err := parseCredentialsJSON(jsonData)
+		require.NoError(t, err)
+		require.Len(t, creds, 2)
+		require.Equal(t, "token1", creds["coder1.example.com"].APIToken)
+		require.Equal(t, "token2", creds["coder2.example.com"].APIToken)
+	})
+
+	t.Run("InvalidJSON", func(t *testing.T) {
+		t.Parallel()
+		jsonData := []byte(`{invalid json}`)
+		_, err := parseCredentialsJSON(jsonData)
+		require.Error(t, err)
+	})
+}
+
+func TestCredentialsMap_RoundTrip(t *testing.T) {
+	t.Parallel()
+
+	creds := credentialsMap{
+		"coder1.example.com": {
+			CoderURL: "coder1.example.com",
+			APIToken: "token1",
+		},
+		"coder2.example.com:8080": {
+			CoderURL: "coder2.example.com:8080",
+			APIToken: "token2",
+		},
+	}
+
+	jsonData, err := json.Marshal(creds)
+	require.NoError(t, err)
+
+	parsed, err := parseCredentialsJSON(jsonData)
+	require.NoError(t, err)
+
+	require.Equal(t, creds, parsed)
+}

cli/sessionstore/sessionstore_other.go

@@ -0,0 +1,17 @@
+//go:build !windows && !darwin
+
+package sessionstore
+
+type operatingSystemKeyring struct{}
+
+func (operatingSystemKeyring) Set(_, _ string) error {
+	return ErrNotImplemented
+}
+
+func (operatingSystemKeyring) Get(_ string) ([]byte, error) {
+	return nil, ErrNotImplemented
+}
+
+func (operatingSystemKeyring) Delete(_ string) error {
+	return ErrNotImplemented
+}

cli/sessionstore/sessionstore_other_test.go

@@ -0,0 +1,10 @@
+//go:build !windows && !darwin
+
+package sessionstore_test
+
+import "testing"
+
+func readRawKeychainCredential(t *testing.T, _ string) []byte {
+	t.Fatal("not implemented")
+	return nil
+}

cli/sessionstore/sessionstore_test.go

@@ -0,0 +1,408 @@
+package sessionstore_test
+
+import (
+	"encoding/json"
+	"errors"
+	"fmt"
+	"net/url"
+	"os"
+	"path"
+	"runtime"
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/cli/config"
+	"github.com/coder/coder/v2/cli/sessionstore"
+)
+
+type storedCredentials map[string]struct {
+	CoderURL string `json:"coder_url"`
+	APIToken string `json:"api_token"`
+}
+
+// Generate a test service name for use with the OS keyring. It uses a combination
+// of the test name and a nanosecond timestamp to prevent collisions.
+func keyringTestServiceName(t *testing.T) string {
+	t.Helper()
+	return t.Name() + "_" + fmt.Sprintf("%v", time.Now().UnixNano())
+}
+
+func TestKeyring(t *testing.T) {
+	t.Parallel()
+
+	if runtime.GOOS != "windows" && runtime.GOOS != "darwin" {
+		t.Skip("linux is not supported yet")
+	}
+
+	// This test exercises use of the operating system keyring. As a result,
+	// the operating system keyring is expected to be available.
+
+	const (
+		testURL  = "http://127.0.0.1:1337"
+		testURL2 = "http://127.0.0.1:1338"
+	)
+
+	t.Run("ReadNonExistent", func(t *testing.T) {
+		t.Parallel()
+
+		backend := sessionstore.NewKeyringWithService(keyringTestServiceName(t))
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+		t.Cleanup(func() { _ = backend.Delete(srvURL) })
+
+		_, err = backend.Read(srvURL)
+		require.Error(t, err)
+		require.True(t, os.IsNotExist(err), "expected os.ErrNotExist when reading non-existent token")
+	})
+
+	t.Run("DeleteNonExistent", func(t *testing.T) {
+		t.Parallel()
+
+		backend := sessionstore.NewKeyringWithService(keyringTestServiceName(t))
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+		t.Cleanup(func() { _ = backend.Delete(srvURL) })
+
+		err = backend.Delete(srvURL)
+		require.Error(t, err)
+		require.True(t, errors.Is(err, os.ErrNotExist), "expected os.ErrNotExist when deleting non-existent token")
+	})
+
+	t.Run("WriteAndRead", func(t *testing.T) {
+		t.Parallel()
+
+		backend := sessionstore.NewKeyringWithService(keyringTestServiceName(t))
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+		t.Cleanup(func() { _ = backend.Delete(srvURL) })
+
+		dir := t.TempDir()
+		expSessionFile := path.Join(dir, "session")
+
+		const inputToken = "test-keyring-token-12345"
+		err = backend.Write(srvURL, inputToken)
+		require.NoError(t, err)
+
+		// Verify no session file was created (keyring stores in OS keyring, not file)
+		_, err = os.Stat(expSessionFile)
+		require.True(t, errors.Is(err, os.ErrNotExist), "expected session token file to not exist when using keyring")
+
+		token, err := backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, inputToken, token)
+
+		// Clean up
+		err = backend.Delete(srvURL)
+		require.NoError(t, err)
+	})
+
+	t.Run("WriteAndDelete", func(t *testing.T) {
+		t.Parallel()
+
+		backend := sessionstore.NewKeyringWithService(keyringTestServiceName(t))
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+		t.Cleanup(func() { _ = backend.Delete(srvURL) })
+
+		const inputToken = "test-keyring-token-67890"
+		err = backend.Write(srvURL, inputToken)
+		require.NoError(t, err)
+
+		token, err := backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, inputToken, token)
+
+		err = backend.Delete(srvURL)
+		require.NoError(t, err)
+
+		_, err = backend.Read(srvURL)
+		require.Error(t, err)
+		require.True(t, os.IsNotExist(err), "expected os.ErrNotExist after deleting token")
+	})
+
+	t.Run("OverwriteToken", func(t *testing.T) {
+		t.Parallel()
+
+		backend := sessionstore.NewKeyringWithService(keyringTestServiceName(t))
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+		t.Cleanup(func() { _ = backend.Delete(srvURL) })
+
+		// Write first token
+		const firstToken = "first-keyring-token"
+		err = backend.Write(srvURL, firstToken)
+		require.NoError(t, err)
+
+		token, err := backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, firstToken, token)
+
+		// Overwrite with second token
+		const secondToken = "second-keyring-token"
+		err = backend.Write(srvURL, secondToken)
+		require.NoError(t, err)
+
+		token, err = backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, secondToken, token)
+
+		// Clean up
+		err = backend.Delete(srvURL)
+		require.NoError(t, err)
+	})
+
+	t.Run("MultipleServers", func(t *testing.T) {
+		t.Parallel()
+
+		backend := sessionstore.NewKeyringWithService(keyringTestServiceName(t))
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+		srvURL2, err := url.Parse(testURL2)
+		require.NoError(t, err)
+
+		t.Cleanup(func() {
+			_ = backend.Delete(srvURL)
+			_ = backend.Delete(srvURL2)
+		})
+
+		// Write token for server 1
+		const token1 = "token-for-server-1"
+		err = backend.Write(srvURL, token1)
+		require.NoError(t, err)
+
+		// Write token for server 2 (should NOT overwrite server 1)
+		const token2 = "token-for-server-2"
+		err = backend.Write(srvURL2, token2)
+		require.NoError(t, err)
+
+		// Read server 1's credential
+		token, err := backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, token1, token)
+
+		// Read server 2's credential
+		token, err = backend.Read(srvURL2)
+		require.NoError(t, err)
+		require.Equal(t, token2, token)
+
+		// Delete server 1's credential
+		err = backend.Delete(srvURL)
+		require.NoError(t, err)
+
+		// Verify server 1's credential is gone
+		_, err = backend.Read(srvURL)
+		require.Error(t, err)
+		require.True(t, os.IsNotExist(err))
+
+		// Verify server 2's credential still exists
+		token, err = backend.Read(srvURL2)
+		require.NoError(t, err)
+		require.Equal(t, token2, token)
+
+		// Clean up remaining credentials
+		err = backend.Delete(srvURL2)
+		require.NoError(t, err)
+	})
+
+	t.Run("StorageFormat", func(t *testing.T) {
+		t.Parallel()
+		// The storage format must remain consistent to ensure we don't break
+		// compatibility with other Coder related applications that may read
+		// or decode the same credential.
+
+		const testURL1 = "http://127.0.0.1:1337"
+		srv1URL, err := url.Parse(testURL1)
+		require.NoError(t, err)
+
+		const testURL2 = "http://127.0.0.1:1338"
+		srv2URL, err := url.Parse(testURL2)
+		require.NoError(t, err)
+
+		serviceName := keyringTestServiceName(t)
+		backend := sessionstore.NewKeyringWithService(serviceName)
+		t.Cleanup(func() {
+			_ = backend.Delete(srv1URL)
+			_ = backend.Delete(srv2URL)
+		})
+
+		// Write token for server 1
+		const token1 = "token-server-1"
+		err = backend.Write(srv1URL, token1)
+		require.NoError(t, err)
+
+		// Write token for server 2 (should NOT overwrite server 1's token)
+		const token2 = "token-server-2"
+		err = backend.Write(srv2URL, token2)
+		require.NoError(t, err)
+
+		// Verify both credentials are stored in the raw format and can
+		// be extracted through the Backend API.
+		rawCredential := readRawKeychainCredential(t, serviceName)
+
+		storedCreds := make(storedCredentials)
+		err = json.Unmarshal(rawCredential, &storedCreds)
+		require.NoError(t, err, "unmarshalling stored credentials")
+
+		// Both credentials should exist
+		require.Len(t, storedCreds, 2)
+		require.Equal(t, token1, storedCreds[srv1URL.Host].APIToken)
+		require.Equal(t, token2, storedCreds[srv2URL.Host].APIToken)
+
+		// Read individual credentials
+		token, err := backend.Read(srv1URL)
+		require.NoError(t, err)
+		require.Equal(t, token1, token)
+
+		token, err = backend.Read(srv2URL)
+		require.NoError(t, err)
+		require.Equal(t, token2, token)
+
+		// Cleanup
+		err = backend.Delete(srv1URL)
+		require.NoError(t, err)
+		err = backend.Delete(srv2URL)
+		require.NoError(t, err)
+	})
+}
+
+func TestFile(t *testing.T) {
+	const (
+		testURL  = "http://127.0.0.1:1337"
+		testURL2 = "http://127.0.0.1:1338"
+	)
+
+	t.Parallel()
+
+	t.Run("ReadNonExistent", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		backend := sessionstore.NewFile(func() config.Root { return config.Root(dir) })
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+
+		_, err = backend.Read(srvURL)
+		require.Error(t, err)
+		require.True(t, os.IsNotExist(err))
+	})
+
+	t.Run("WriteAndRead", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		backend := sessionstore.NewFile(func() config.Root { return config.Root(dir) })
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+
+		// Write a token
+		const inputToken = "test-token-12345"
+		err = backend.Write(srvURL, inputToken)
+		require.NoError(t, err)
+
+		// Verify the session file was created
+		sessionFile := config.Root(dir).Session()
+		require.True(t, sessionFile.Exists())
+
+		// Read the token back
+		token, err := backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, inputToken, token)
+	})
+
+	t.Run("WriteAndDelete", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		backend := sessionstore.NewFile(func() config.Root { return config.Root(dir) })
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+
+		// Write a token
+		const inputToken = "test-token-67890"
+		err = backend.Write(srvURL, inputToken)
+		require.NoError(t, err)
+
+		// Verify the token was written
+		token, err := backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, inputToken, token)
+
+		// Delete the token
+		err = backend.Delete(srvURL)
+		require.NoError(t, err)
+
+		// Verify the token is gone
+		_, err = backend.Read(srvURL)
+		require.Error(t, err)
+		require.True(t, os.IsNotExist(err))
+	})
+
+	t.Run("DeleteNonExistent", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		backend := sessionstore.NewFile(func() config.Root { return config.Root(dir) })
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+
+		// Attempt to delete a non-existent token
+		err = backend.Delete(srvURL)
+		require.Error(t, err)
+		require.True(t, os.IsNotExist(err))
+	})
+
+	t.Run("OverwriteToken", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		backend := sessionstore.NewFile(func() config.Root { return config.Root(dir) })
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+
+		// Write first token
+		const firstToken = "first-token"
+		err = backend.Write(srvURL, firstToken)
+		require.NoError(t, err)
+
+		token, err := backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, firstToken, token)
+
+		// Overwrite with second token
+		const secondToken = "second-token"
+		err = backend.Write(srvURL, secondToken)
+		require.NoError(t, err)
+
+		token, err = backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, secondToken, token)
+	})
+
+	t.Run("WriteIgnoresURL", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		backend := sessionstore.NewFile(func() config.Root { return config.Root(dir) })
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+		srvURL2, err := url.Parse(testURL2)
+		require.NoError(t, err)
+
+		//nolint:gosec // Write with first URL test token
+		const firstToken = "token-for-url1"
+		err = backend.Write(srvURL, firstToken)
+		require.NoError(t, err)
+
+		//nolint:gosec // Write with second URL - should overwrite
+		const secondToken = "token-for-url2"
+		err = backend.Write(srvURL2, secondToken)
+		require.NoError(t, err)
+
+		// Should have the second token (File backend doesn't differentiate by URL)
+		token, err := backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, secondToken, token)
+	})
+}

cli/sessionstore/sessionstore_windows.go

@@ -0,0 +1,60 @@
+//go:build windows
+
+package sessionstore
+
+import (
+	"errors"
+	"os"
+	"syscall"
+
+	"github.com/danieljoos/wincred"
+)
+
+// operatingSystemKeyring implements keyringProvider and uses Windows Credential Manager.
+// It is largely adapted from the zalando/go-keyring package.
+type operatingSystemKeyring struct{}
+
+func (operatingSystemKeyring) Set(service, credential string) error {
+	// password may not exceed 2560 bytes (https://github.com/jaraco/keyring/issues/540#issuecomment-968329967)
+	if len(credential) > 2560 {
+		return ErrSetDataTooBig
+	}
+
+	// service may not exceed 512 bytes (might need more testing)
+	if len(service) >= 512 {
+		return ErrSetDataTooBig
+	}
+
+	// service may not exceed 32k but problems occur before that
+	// so we limit it to 30k
+	if len(service) > 1024*30 {
+		return ErrSetDataTooBig
+	}
+
+	cred := wincred.NewGenericCredential(service)
+	cred.CredentialBlob = []byte(credential)
+	cred.Persist = wincred.PersistLocalMachine
+	return cred.Write()
+}
+
+func (operatingSystemKeyring) Get(service string) ([]byte, error) {
+	cred, err := wincred.GetGenericCredential(service)
+	if err != nil {
+		if errors.Is(err, syscall.ERROR_NOT_FOUND) {
+			return nil, os.ErrNotExist
+		}
+		return nil, err
+	}
+	return cred.CredentialBlob, nil
+}
+
+func (operatingSystemKeyring) Delete(service string) error {
+	cred, err := wincred.GetGenericCredential(service)
+	if err != nil {
+		if errors.Is(err, syscall.ERROR_NOT_FOUND) {
+			return os.ErrNotExist
+		}
+		return err
+	}
+	return cred.Delete()
+}

cli/sessionstore/sessionstore_windows_test.go

@@ -0,0 +1,74 @@
+//go:build windows
+
+package sessionstore_test
+
+import (
+	"encoding/json"
+	"net/url"
+	"os"
+	"testing"
+
+	"github.com/danieljoos/wincred"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/cli/sessionstore"
+)
+
+func readRawKeychainCredential(t *testing.T, serviceName string) []byte {
+	t.Helper()
+
+	winCred, err := wincred.GetGenericCredential(serviceName)
+	if err != nil {
+		t.Fatal(err)
+	}
+	return winCred.CredentialBlob
+}
+
+func TestWindowsKeyring_WriteReadDelete(t *testing.T) {
+	t.Parallel()
+
+	const testURL = "http://127.0.0.1:1337"
+	srvURL, err := url.Parse(testURL)
+	require.NoError(t, err)
+
+	serviceName := keyringTestServiceName(t)
+	backend := sessionstore.NewKeyringWithService(serviceName)
+	t.Cleanup(func() { _ = backend.Delete(srvURL) })
+
+	// Verify no token exists initially
+	_, err = backend.Read(srvURL)
+	require.ErrorIs(t, err, os.ErrNotExist)
+
+	// Write a token
+	const inputToken = "test-token-12345"
+	err = backend.Write(srvURL, inputToken)
+	require.NoError(t, err)
+
+	// Verify the credential is stored in Windows Credential Manager with correct format
+	winCred, err := wincred.GetGenericCredential(serviceName)
+	require.NoError(t, err, "getting windows credential")
+
+	storedCreds := make(storedCredentials)
+	err = json.Unmarshal(winCred.CredentialBlob, &storedCreds)
+	require.NoError(t, err, "unmarshalling stored credentials")
+
+	// Verify the stored values
+	require.Len(t, storedCreds, 1)
+	cred, ok := storedCreds[srvURL.Host]
+	require.True(t, ok, "credential for URL should exist")
+	require.Equal(t, inputToken, cred.APIToken)
+	require.Equal(t, srvURL.Host, cred.CoderURL)
+
+	// Read the token back
+	token, err := backend.Read(srvURL)
+	require.NoError(t, err)
+	require.Equal(t, inputToken, token)
+
+	// Delete the token
+	err = backend.Delete(srvURL)
+	require.NoError(t, err)
+
+	// Verify token is deleted
+	_, err = backend.Read(srvURL)
+	require.ErrorIs(t, err, os.ErrNotExist)
+}

cli/testdata/coder_--help.golden

@@ -108,6 +108,11 @@ variables or flags.
       --url url, $CODER_URL
           URL to a deployment.
 
+      --use-keyring bool, $CODER_USE_KEYRING
+          Store and retrieve session tokens using the operating system keyring.
+          Currently only supported on Windows. By default, tokens are stored in
+          plain text files.
+
   -v, --verbose bool, $CODER_VERBOSE
           Enable verbose output.
 

cli/testdata/coder_list_--output_json.golden

@@ -90,6 +90,7 @@
     "allow_renames": false,
     "favorite": false,
     "next_start_at": "====[timestamp]=====",
-    "is_prebuild": false
+    "is_prebuild": false,
+    "task_id": null
   }
 ]

cli/testdata/coder_login_--help.golden

@@ -5,6 +5,10 @@ USAGE:
 
   Authenticate with Coder deployment
 
+  By default, the session token is stored in a plain text file. Use the
+  --use-keyring flag or set CODER_USE_KEYRING=true to store the token in the
+  operating system keyring instead.
+
 OPTIONS:
       --first-user-email string, $CODER_FIRST_USER_EMAIL
           Specifies an email address to use if creating the first user for the

cli/testdata/coder_provisioner_list_--output_json.golden

@@ -7,7 +7,7 @@
     "last_seen_at": "====[timestamp]=====",
     "name": "test-daemon",
     "version": "v0.0.0-devel",
-    "api_version": "1.11",
+    "api_version": "1.12",
     "provisioners": [
       "echo"
     ],

cli/testdata/coder_server_--help.golden

@@ -80,6 +80,50 @@ OPTIONS:
           Periodically check for new releases of Coder and inform the owner. The
           check is performed once per day.
 
+AI BRIDGE OPTIONS: 
+      --aibridge-anthropic-base-url string, $CODER_AIBRIDGE_ANTHROPIC_BASE_URL (default: https://api.anthropic.com/)
+          The base URL of the Anthropic API.
+
+      --aibridge-anthropic-key string, $CODER_AIBRIDGE_ANTHROPIC_KEY
+          The key to authenticate against the Anthropic API.
+
+      --aibridge-bedrock-access-key string, $CODER_AIBRIDGE_BEDROCK_ACCESS_KEY
+          The access key to authenticate against the AWS Bedrock API.
+
+      --aibridge-bedrock-access-key-secret string, $CODER_AIBRIDGE_BEDROCK_ACCESS_KEY_SECRET
+          The access key secret to use with the access key to authenticate
+          against the AWS Bedrock API.
+
+      --aibridge-bedrock-model string, $CODER_AIBRIDGE_BEDROCK_MODEL (default: global.anthropic.claude-sonnet-4-5-20250929-v1:0)
+          The model to use when making requests to the AWS Bedrock API.
+
+      --aibridge-bedrock-region string, $CODER_AIBRIDGE_BEDROCK_REGION
+          The AWS Bedrock API region.
+
+      --aibridge-bedrock-small-fastmodel string, $CODER_AIBRIDGE_BEDROCK_SMALL_FAST_MODEL (default: global.anthropic.claude-haiku-4-5-20251001-v1:0)
+          The small fast model to use when making requests to the AWS Bedrock
+          API. Claude Code uses Haiku-class models to perform background tasks.
+          See
+          https://docs.claude.com/en/docs/claude-code/settings#environment-variables.
+
+      --aibridge-retention duration, $CODER_AIBRIDGE_RETENTION (default: 60d)
+          Length of time to retain data such as interceptions and all related
+          records (token, prompt, tool use).
+
+      --aibridge-enabled bool, $CODER_AIBRIDGE_ENABLED (default: false)
+          Whether to start an in-memory aibridged instance.
+
+      --aibridge-inject-coder-mcp-tools bool, $CODER_AIBRIDGE_INJECT_CODER_MCP_TOOLS (default: false)
+          Whether to inject Coder's MCP tools into intercepted AI Bridge
+          requests (requires the "oauth2" and "mcp-server-http" experiments to
+          be enabled).
+
+      --aibridge-openai-base-url string, $CODER_AIBRIDGE_OPENAI_BASE_URL (default: https://api.openai.com/v1/)
+          The base URL of the OpenAI API.
+
+      --aibridge-openai-key string, $CODER_AIBRIDGE_OPENAI_KEY
+          The key to authenticate against the OpenAI API.
+
 CLIENT OPTIONS: 
 These options change the behavior of how clients interact with the Coder.
 Clients include the Coder CLI, Coder Desktop, IDE extensions, and the web UI.

cli/testdata/coder_tokens_create_--help.golden

@@ -10,7 +10,9 @@ OPTIONS:
           Repeatable allow-list entry (<type>:<uuid>, e.g. workspace:1234-...).
 
       --lifetime string, $CODER_TOKEN_LIFETIME
-          Specify a duration for the lifetime of the token.
+          Duration for the token lifetime. Supports standard Go duration units
+          (ns, us, ms, s, m, h) plus d (days) and y (years). Examples: 8h, 30d,
+          1y, 1d12h30m.
 
   -n, --name string, $CODER_TOKEN_NAME
           Specify a human-readable name.

cli/testdata/server-config.yaml.golden

@@ -714,8 +714,7 @@ workspace_prebuilds:
   # (default: 3, type: int)
   failure_hard_limit: 3
 aibridge:
-  # Whether to start an in-memory aibridged instance ("aibridge" experiment must be
-  # enabled, too).
+  # Whether to start an in-memory aibridged instance.
   # (default: false, type: bool)
   enabled: false
   # The base URL of the OpenAI API.
@@ -726,7 +725,33 @@ aibridge:
   openai_key: ""
   # The base URL of the Anthropic API.
   # (default: https://api.anthropic.com/, type: string)
-  base_url: https://api.anthropic.com/
+  anthropic_base_url: https://api.anthropic.com/
   # The key to authenticate against the Anthropic API.
   # (default: <unset>, type: string)
-  key: ""
+  anthropic_key: ""
+  # The AWS Bedrock API region.
+  # (default: <unset>, type: string)
+  bedrock_region: ""
+  # The access key to authenticate against the AWS Bedrock API.
+  # (default: <unset>, type: string)
+  bedrock_access_key: ""
+  # The access key secret to use with the access key to authenticate against the AWS
+  # Bedrock API.
+  # (default: <unset>, type: string)
+  bedrock_access_key_secret: ""
+  # The model to use when making requests to the AWS Bedrock API.
+  # (default: global.anthropic.claude-sonnet-4-5-20250929-v1:0, type: string)
+  bedrock_model: global.anthropic.claude-sonnet-4-5-20250929-v1:0
+  # The small fast model to use when making requests to the AWS Bedrock API. Claude
+  # Code uses Haiku-class models to perform background tasks. See
+  # https://docs.claude.com/en/docs/claude-code/settings#environment-variables.
+  # (default: global.anthropic.claude-haiku-4-5-20251001-v1:0, type: string)
+  bedrock_small_fast_model: global.anthropic.claude-haiku-4-5-20251001-v1:0
+  # Whether to inject Coder's MCP tools into intercepted AI Bridge requests
+  # (requires the "oauth2" and "mcp-server-http" experiments to be enabled).
+  # (default: false, type: bool)
+  inject_coder_mcp_tools: false
+  # Length of time to retain data such as interceptions and all related records
+  # (token, prompt, tool use).
+  # (default: 60d, type: duration)
+  retention: 1440h0m0s

cli/tokens.go

@@ -123,7 +123,7 @@ func (r *RootCmd) createToken() *serpent.Command {
 		{
 			Flag:        "lifetime",
 			Env:         "CODER_TOKEN_LIFETIME",
-			Description: "Specify a duration for the lifetime of the token.",
+			Description: "Duration for the token lifetime. Supports standard Go duration units (ns, us, ms, s, m, h) plus d (days) and y (years). Examples: 8h, 30d, 1y, 1d12h30m.",
 			Value:       serpent.StringOf(&tokenLifetime),
 		},
 		{

coderd/agentapi/api.go

@@ -239,6 +239,10 @@ func (a *API) Serve(ctx context.Context, l net.Listener) error {
 		return xerrors.Errorf("create agent API server: %w", err)
 	}
 
+	if err := a.ResourcesMonitoringAPI.InitMonitors(ctx); err != nil {
+		return xerrors.Errorf("initialize resource monitoring: %w", err)
+	}
+
 	return server.Serve(ctx, l)
 }
 

coderd/agentapi/resources_monitoring.go

@@ -5,6 +5,7 @@ import (
 	"database/sql"
 	"errors"
 	"fmt"
+	"sync"
 	"time"
 
 	"golang.org/x/xerrors"
@@ -33,42 +34,60 @@ type ResourcesMonitoringAPI struct {
 
 	Debounce time.Duration
 	Config   resourcesmonitor.Config
+
+	// Cache resource monitors on first call to avoid millions of DB queries per day.
+	memoryMonitor  database.WorkspaceAgentMemoryResourceMonitor
+	volumeMonitors []database.WorkspaceAgentVolumeResourceMonitor
+	monitorsLock   sync.RWMutex
 }
 
-func (a *ResourcesMonitoringAPI) GetResourcesMonitoringConfiguration(ctx context.Context, _ *proto.GetResourcesMonitoringConfigurationRequest) (*proto.GetResourcesMonitoringConfigurationResponse, error) {
-	memoryMonitor, memoryErr := a.Database.FetchMemoryResourceMonitorsByAgentID(ctx, a.AgentID)
-	if memoryErr != nil && !errors.Is(memoryErr, sql.ErrNoRows) {
-		return nil, xerrors.Errorf("failed to fetch memory resource monitor: %w", memoryErr)
+// InitMonitors fetches resource monitors from the database and caches them.
+// This must be called once after creating a ResourcesMonitoringAPI, the context should be
+// the agent per-RPC connection context. If fetching fails with a real error (not sql.ErrNoRows), the
+// connection should be torn down.
+func (a *ResourcesMonitoringAPI) InitMonitors(ctx context.Context) error {
+	memMon, err := a.Database.FetchMemoryResourceMonitorsByAgentID(ctx, a.AgentID)
+	if err != nil && !errors.Is(err, sql.ErrNoRows) {
+		return xerrors.Errorf("fetch memory resource monitor: %w", err)
+	}
+	// If sql.ErrNoRows, memoryMonitor stays as zero value (CreatedAt.IsZero() = true).
+	// Otherwise, store the fetched monitor.
+	if err == nil {
+		a.memoryMonitor = memMon
 	}
 
-	volumeMonitors, err := a.Database.FetchVolumesResourceMonitorsByAgentID(ctx, a.AgentID)
+	volMons, err := a.Database.FetchVolumesResourceMonitorsByAgentID(ctx, a.AgentID)
 	if err != nil {
-		return nil, xerrors.Errorf("failed to fetch volume resource monitors: %w", err)
+		return xerrors.Errorf("fetch volume resource monitors: %w", err)
 	}
+	// 0 length is valid, indicating none configured, since the volume monitors in the DB can be many.
+	a.volumeMonitors = volMons
 
+	return nil
+}
+
+func (a *ResourcesMonitoringAPI) GetResourcesMonitoringConfiguration(_ context.Context, _ *proto.GetResourcesMonitoringConfigurationRequest) (*proto.GetResourcesMonitoringConfigurationResponse, error) {
 	return &proto.GetResourcesMonitoringConfigurationResponse{
 		Config: &proto.GetResourcesMonitoringConfigurationResponse_Config{
 			CollectionIntervalSeconds: int32(a.Config.CollectionInterval.Seconds()),
 			NumDatapoints:             a.Config.NumDatapoints,
 		},
 		Memory: func() *proto.GetResourcesMonitoringConfigurationResponse_Memory {
-			if memoryErr != nil {
+			if a.memoryMonitor.CreatedAt.IsZero() {
 				return nil
 			}
-
 			return &proto.GetResourcesMonitoringConfigurationResponse_Memory{
-				Enabled: memoryMonitor.Enabled,
+				Enabled: a.memoryMonitor.Enabled,
 			}
 		}(),
 		Volumes: func() []*proto.GetResourcesMonitoringConfigurationResponse_Volume {
-			volumes := make([]*proto.GetResourcesMonitoringConfigurationResponse_Volume, 0, len(volumeMonitors))
-			for _, monitor := range volumeMonitors {
+			volumes := make([]*proto.GetResourcesMonitoringConfigurationResponse_Volume, 0, len(a.volumeMonitors))
+			for _, monitor := range a.volumeMonitors {
 				volumes = append(volumes, &proto.GetResourcesMonitoringConfigurationResponse_Volume{
 					Enabled: monitor.Enabled,
 					Path:    monitor.Path,
 				})
 			}
-
 			return volumes
 		}(),
 	}, nil
@@ -77,6 +96,10 @@ func (a *ResourcesMonitoringAPI) GetResourcesMonitoringConfiguration(ctx context
 func (a *ResourcesMonitoringAPI) PushResourcesMonitoringUsage(ctx context.Context, req *proto.PushResourcesMonitoringUsageRequest) (*proto.PushResourcesMonitoringUsageResponse, error) {
 	var err error
 
+	// Lock for the entire push operation since calls are sequential from the agent
+	a.monitorsLock.Lock()
+	defer a.monitorsLock.Unlock()
+
 	if memoryErr := a.monitorMemory(ctx, req.Datapoints); memoryErr != nil {
 		err = errors.Join(err, xerrors.Errorf("monitor memory: %w", memoryErr))
 	}
@@ -89,18 +112,7 @@ func (a *ResourcesMonitoringAPI) PushResourcesMonitoringUsage(ctx context.Contex
 }
 
 func (a *ResourcesMonitoringAPI) monitorMemory(ctx context.Context, datapoints []*proto.PushResourcesMonitoringUsageRequest_Datapoint) error {
-	monitor, err := a.Database.FetchMemoryResourceMonitorsByAgentID(ctx, a.AgentID)
-	if err != nil {
-		// It is valid for an agent to not have a memory monitor, so we
-		// do not want to treat it as an error.
-		if errors.Is(err, sql.ErrNoRows) {
-			return nil
-		}
-
-		return xerrors.Errorf("fetch memory resource monitor: %w", err)
-	}
-
-	if !monitor.Enabled {
+	if !a.memoryMonitor.Enabled {
 		return nil
 	}
 
@@ -109,15 +121,15 @@ func (a *ResourcesMonitoringAPI) monitorMemory(ctx context.Context, datapoints [
 		usageDatapoints = append(usageDatapoints, datapoint.Memory)
 	}
 
-	usageStates := resourcesmonitor.CalculateMemoryUsageStates(monitor, usageDatapoints)
+	usageStates := resourcesmonitor.CalculateMemoryUsageStates(a.memoryMonitor, usageDatapoints)
 
-	oldState := monitor.State
+	oldState := a.memoryMonitor.State
 	newState := resourcesmonitor.NextState(a.Config, oldState, usageStates)
 
-	debouncedUntil, shouldNotify := monitor.Debounce(a.Debounce, a.Clock.Now(), oldState, newState)
+	debouncedUntil, shouldNotify := a.memoryMonitor.Debounce(a.Debounce, a.Clock.Now(), oldState, newState)
 
 	//nolint:gocritic // We need to be able to update the resource monitor here.
-	err = a.Database.UpdateMemoryResourceMonitor(dbauthz.AsResourceMonitor(ctx), database.UpdateMemoryResourceMonitorParams{
+	err := a.Database.UpdateMemoryResourceMonitor(dbauthz.AsResourceMonitor(ctx), database.UpdateMemoryResourceMonitorParams{
 		AgentID:        a.AgentID,
 		State:          newState,
 		UpdatedAt:      dbtime.Time(a.Clock.Now()),
@@ -127,6 +139,11 @@ func (a *ResourcesMonitoringAPI) monitorMemory(ctx context.Context, datapoints [
 		return xerrors.Errorf("update workspace monitor: %w", err)
 	}
 
+	// Update cached state
+	a.memoryMonitor.State = newState
+	a.memoryMonitor.DebouncedUntil = dbtime.Time(debouncedUntil)
+	a.memoryMonitor.UpdatedAt = dbtime.Time(a.Clock.Now())
+
 	if !shouldNotify {
 		return nil
 	}
@@ -143,7 +160,7 @@ func (a *ResourcesMonitoringAPI) monitorMemory(ctx context.Context, datapoints [
 		notifications.TemplateWorkspaceOutOfMemory,
 		map[string]string{
 			"workspace": workspace.Name,
-			"threshold": fmt.Sprintf("%d%%", monitor.Threshold),
+			"threshold": fmt.Sprintf("%d%%", a.memoryMonitor.Threshold),
 		},
 		map[string]any{
 			// NOTE(DanielleMaywood):
@@ -169,14 +186,9 @@ func (a *ResourcesMonitoringAPI) monitorMemory(ctx context.Context, datapoints [
 }
 
 func (a *ResourcesMonitoringAPI) monitorVolumes(ctx context.Context, datapoints []*proto.PushResourcesMonitoringUsageRequest_Datapoint) error {
-	volumeMonitors, err := a.Database.FetchVolumesResourceMonitorsByAgentID(ctx, a.AgentID)
-	if err != nil {
-		return xerrors.Errorf("get or insert volume monitor: %w", err)
-	}
-
 	outOfDiskVolumes := make([]map[string]any, 0)
 
-	for _, monitor := range volumeMonitors {
+	for i, monitor := range a.volumeMonitors {
 		if !monitor.Enabled {
 			continue
 		}
@@ -219,6 +231,11 @@ func (a *ResourcesMonitoringAPI) monitorVolumes(ctx context.Context, datapoints
 		}); err != nil {
 			return xerrors.Errorf("update workspace monitor: %w", err)
 		}
+
+		// Update cached state
+		a.volumeMonitors[i].State = newState
+		a.volumeMonitors[i].DebouncedUntil = dbtime.Time(debouncedUntil)
+		a.volumeMonitors[i].UpdatedAt = dbtime.Time(a.Clock.Now())
 	}
 
 	if len(outOfDiskVolumes) == 0 {

coderd/agentapi/resources_monitoring_test.go

@@ -101,6 +101,9 @@ func TestMemoryResourceMonitorDebounce(t *testing.T) {
 		Threshold: 80,
 	})
 
+	// Initialize API to fetch and cache the monitors
+	require.NoError(t, api.InitMonitors(context.Background()))
+
 	// When: The monitor is given a state that will trigger NOK
 	_, err := api.PushResourcesMonitoringUsage(context.Background(), &agentproto.PushResourcesMonitoringUsageRequest{
 		Datapoints: []*agentproto.PushResourcesMonitoringUsageRequest_Datapoint{
@@ -304,6 +307,9 @@ func TestMemoryResourceMonitor(t *testing.T) {
 				Threshold: 80,
 			})
 
+			// Initialize API to fetch and cache the monitors
+			require.NoError(t, api.InitMonitors(context.Background()))
+
 			clock.Set(collectedAt)
 			_, err := api.PushResourcesMonitoringUsage(context.Background(), &agentproto.PushResourcesMonitoringUsageRequest{
 				Datapoints: datapoints,
@@ -337,6 +343,8 @@ func TestMemoryResourceMonitorMissingData(t *testing.T) {
 			State:     database.WorkspaceAgentMonitorStateOK,
 			Threshold: 80,
 		})
+		// Initialize API to fetch and cache the monitors
+		require.NoError(t, api.InitMonitors(context.Background()))
 
 		// When: A datapoint is missing, surrounded by two NOK datapoints.
 		_, err := api.PushResourcesMonitoringUsage(context.Background(), &agentproto.PushResourcesMonitoringUsageRequest{
@@ -387,6 +395,9 @@ func TestMemoryResourceMonitorMissingData(t *testing.T) {
 			Threshold: 80,
 		})
 
+		// Initialize API to fetch and cache the monitors
+		require.NoError(t, api.InitMonitors(context.Background()))
+
 		// When: A datapoint is missing, surrounded by two OK datapoints.
 		_, err := api.PushResourcesMonitoringUsage(context.Background(), &agentproto.PushResourcesMonitoringUsageRequest{
 			Datapoints: []*agentproto.PushResourcesMonitoringUsageRequest_Datapoint{
@@ -466,6 +477,9 @@ func TestVolumeResourceMonitorDebounce(t *testing.T) {
 		Threshold: 80,
 	})
 
+	// Initialize API to fetch and cache the monitors
+	require.NoError(t, api.InitMonitors(context.Background()))
+
 	// When:
 	//  - First monitor is in a NOK state
 	//  - Second monitor is in an OK state
@@ -742,6 +756,9 @@ func TestVolumeResourceMonitor(t *testing.T) {
 				Threshold: tt.thresholdPercent,
 			})
 
+			// Initialize API to fetch and cache the monitors
+			require.NoError(t, api.InitMonitors(context.Background()))
+
 			clock.Set(collectedAt)
 			_, err := api.PushResourcesMonitoringUsage(context.Background(), &agentproto.PushResourcesMonitoringUsageRequest{
 				Datapoints: datapoints,
@@ -780,6 +797,9 @@ func TestVolumeResourceMonitorMultiple(t *testing.T) {
 		Threshold: 80,
 	})
 
+	// Initialize API to fetch and cache the monitors
+	require.NoError(t, api.InitMonitors(context.Background()))
+
 	// When: both of them move to a NOK state
 	_, err := api.PushResourcesMonitoringUsage(context.Background(), &agentproto.PushResourcesMonitoringUsageRequest{
 		Datapoints: []*agentproto.PushResourcesMonitoringUsageRequest_Datapoint{
@@ -832,6 +852,9 @@ func TestVolumeResourceMonitorMissingData(t *testing.T) {
 			Threshold: 80,
 		})
 
+		// Initialize API to fetch and cache the monitors
+		require.NoError(t, api.InitMonitors(context.Background()))
+
 		// When: A datapoint is missing, surrounded by two NOK datapoints.
 		_, err := api.PushResourcesMonitoringUsage(context.Background(), &agentproto.PushResourcesMonitoringUsageRequest{
 			Datapoints: []*agentproto.PushResourcesMonitoringUsageRequest_Datapoint{
@@ -891,6 +914,9 @@ func TestVolumeResourceMonitorMissingData(t *testing.T) {
 			Threshold: 80,
 		})
 
+		// Initialize API to fetch and cache the monitors
+		require.NoError(t, api.InitMonitors(context.Background()))
+
 		// When: A datapoint is missing, surrounded by two OK datapoints.
 		_, err := api.PushResourcesMonitoringUsage(context.Background(), &agentproto.PushResourcesMonitoringUsageRequest{
 			Datapoints: []*agentproto.PushResourcesMonitoringUsageRequest_Datapoint{

coderd/aitasks.go

@@ -7,13 +7,13 @@ import (
 	"net/http"
 	"net/url"
 	"slices"
-	"strings"
 	"time"
 
 	"github.com/google/uuid"
 	"golang.org/x/xerrors"
 
 	"cdr.dev/slog"
+
 	"github.com/coder/coder/v2/coderd/audit"
 	"github.com/coder/coder/v2/coderd/database"
 	"github.com/coder/coder/v2/coderd/database/dbtime"
@@ -24,62 +24,13 @@ import (
 	"github.com/coder/coder/v2/coderd/rbac/policy"
 	"github.com/coder/coder/v2/coderd/searchquery"
 	"github.com/coder/coder/v2/coderd/taskname"
+	"github.com/coder/coder/v2/coderd/util/ptr"
+	"github.com/coder/coder/v2/coderd/util/slice"
 	"github.com/coder/coder/v2/codersdk"
 
 	aiagentapi "github.com/coder/agentapi-sdk-go"
 )
 
-// This endpoint is experimental and not guaranteed to be stable, so we're not
-// generating public-facing documentation for it.
-func (api *API) aiTasksPrompts(rw http.ResponseWriter, r *http.Request) {
-	ctx := r.Context()
-
-	buildIDsParam := r.URL.Query().Get("build_ids")
-	if buildIDsParam == "" {
-		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
-			Message: "build_ids query parameter is required",
-		})
-		return
-	}
-
-	// Parse build IDs
-	buildIDStrings := strings.Split(buildIDsParam, ",")
-	buildIDs := make([]uuid.UUID, 0, len(buildIDStrings))
-	for _, idStr := range buildIDStrings {
-		id, err := uuid.Parse(strings.TrimSpace(idStr))
-		if err != nil {
-			httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
-				Message: fmt.Sprintf("Invalid build ID format: %s", idStr),
-				Detail:  err.Error(),
-			})
-			return
-		}
-		buildIDs = append(buildIDs, id)
-	}
-
-	parameters, err := api.Database.GetWorkspaceBuildParametersByBuildIDs(ctx, buildIDs)
-	if err != nil {
-		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
-			Message: "Internal error fetching workspace build parameters.",
-			Detail:  err.Error(),
-		})
-		return
-	}
-
-	promptsByBuildID := make(map[string]string, len(parameters))
-	for _, param := range parameters {
-		if param.Name != codersdk.AITaskPromptParameterName {
-			continue
-		}
-		buildID := param.WorkspaceBuildID.String()
-		promptsByBuildID[buildID] = param.Value
-	}
-
-	httpapi.Write(ctx, rw, http.StatusOK, codersdk.AITasksPromptsResponse{
-		Prompts: promptsByBuildID,
-	})
-}
-
 // @Summary Create a new AI task
 // @Description: EXPERIMENTAL: this endpoint is experimental and not guaranteed to be stable.
 // @ID create-task
@@ -143,7 +94,7 @@ func (api *API) tasksCreate(rw http.ResponseWriter, r *http.Request) {
 
 	if !templateVersion.HasAITask.Valid || !templateVersion.HasAITask.Bool {
 		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
-			Message: fmt.Sprintf(`Template does not have required parameter %q`, codersdk.AITaskPromptParameterName),
+			Message: `Template does not have a valid "coder_ai_task" resource.`,
 		})
 		return
 	}
@@ -174,13 +125,31 @@ func (api *API) tasksCreate(rw http.ResponseWriter, r *http.Request) {
 		}
 	}
 
+	// Check if the template defines the AI Prompt parameter.
+	templateParams, err := api.Database.GetTemplateVersionParameters(ctx, req.TemplateVersionID)
+	if err != nil {
+		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
+			Message: "Internal error fetching template parameters.",
+			Detail:  err.Error(),
+		})
+		return
+	}
+
+	var richParams []codersdk.WorkspaceBuildParameter
+	if _, hasAIPromptParam := slice.Find(templateParams, func(param database.TemplateVersionParameter) bool {
+		return param.Name == codersdk.AITaskPromptParameterName
+	}); hasAIPromptParam {
+		// Only add the AI Prompt parameter if the template defines it.
+		richParams = []codersdk.WorkspaceBuildParameter{
+			{Name: codersdk.AITaskPromptParameterName, Value: req.Input},
+		}
+	}
+
 	createReq := codersdk.CreateWorkspaceRequest{
 		Name:                    taskName,
 		TemplateVersionID:       req.TemplateVersionID,
 		TemplateVersionPresetID: req.TemplateVersionPresetID,
-		RichParameterValues: []codersdk.WorkspaceBuildParameter{
-			{Name: codersdk.AITaskPromptParameterName, Value: req.Input},
-		},
+		RichParameterValues:     richParams,
 	}
 
 	var owner workspaceOwner
@@ -241,6 +210,7 @@ func (api *API) tasksCreate(rw http.ResponseWriter, r *http.Request) {
 			// Create task record in the database before creating the workspace so that
 			// we can request that the workspace be linked to it after creation.
 			dbTaskTable, err = tx.InsertTask(ctx, database.InsertTaskParams{
+				ID:                 uuid.New(),
 				OrganizationID:     templateVersion.OrganizationID,
 				OwnerID:            owner.ID,
 				Name:               taskName,
@@ -302,15 +272,21 @@ func (api *API) tasksCreate(rw http.ResponseWriter, r *http.Request) {
 func taskFromDBTaskAndWorkspace(dbTask database.Task, ws codersdk.Workspace) codersdk.Task {
 	var taskAgentLifecycle *codersdk.WorkspaceAgentLifecycle
 	var taskAgentHealth *codersdk.WorkspaceAgentHealth
+	var taskAppHealth *codersdk.WorkspaceAppHealth
 
-	// If we have an agent ID from the task, find the agent details in the
-	// workspace.
+	if dbTask.WorkspaceAgentLifecycleState.Valid {
+		taskAgentLifecycle = ptr.Ref(codersdk.WorkspaceAgentLifecycle(dbTask.WorkspaceAgentLifecycleState.WorkspaceAgentLifecycleState))
+	}
+	if dbTask.WorkspaceAppHealth.Valid {
+		taskAppHealth = ptr.Ref(codersdk.WorkspaceAppHealth(dbTask.WorkspaceAppHealth.WorkspaceAppHealth))
+	}
+
+	// If we have an agent ID from the task, find the agent health info
 	if dbTask.WorkspaceAgentID.Valid {
 	findTaskAgentLoop:
 		for _, resource := range ws.LatestBuild.Resources {
 			for _, agent := range resource.Agents {
 				if agent.ID == dbTask.WorkspaceAgentID.UUID {
-					taskAgentLifecycle = &agent.LifecycleState
 					taskAgentHealth = &agent.Health
 					break findTaskAgentLoop
 				}
@@ -318,28 +294,14 @@ func taskFromDBTaskAndWorkspace(dbTask database.Task, ws codersdk.Workspace) cod
 		}
 	}
 
-	// Ignore 'latest app status' if it is older than the latest build and the
-	// latest build is a 'start' transition. This ensures that you don't show a
-	// stale app status from a previous build. For stop transitions, there is
-	// still value in showing the latest app status.
-	var currentState *codersdk.TaskStateEntry
-	if ws.LatestAppStatus != nil {
-		if ws.LatestBuild.Transition != codersdk.WorkspaceTransitionStart || ws.LatestAppStatus.CreatedAt.After(ws.LatestBuild.CreatedAt) {
-			currentState = &codersdk.TaskStateEntry{
-				Timestamp: ws.LatestAppStatus.CreatedAt,
-				State:     codersdk.TaskState(ws.LatestAppStatus.State),
-				Message:   ws.LatestAppStatus.Message,
-				URI:       ws.LatestAppStatus.URI,
-			}
-		}
-	}
+	currentState := deriveTaskCurrentState(dbTask, ws, taskAgentLifecycle, taskAppHealth)
 
 	return codersdk.Task{
 		ID:                      dbTask.ID,
 		OrganizationID:          dbTask.OrganizationID,
 		OwnerID:                 dbTask.OwnerID,
-		OwnerName:               ws.OwnerName,
-		OwnerAvatarURL:          ws.OwnerAvatarURL,
+		OwnerName:               dbTask.OwnerUsername,
+		OwnerAvatarURL:          dbTask.OwnerAvatarUrl,
 		Name:                    dbTask.Name,
 		TemplateID:              ws.TemplateID,
 		TemplateVersionID:       dbTask.TemplateVersionID,
@@ -362,6 +324,73 @@ func taskFromDBTaskAndWorkspace(dbTask database.Task, ws codersdk.Workspace) cod
 	}
 }
 
+// deriveTaskCurrentState determines the current state of a task based on the
+// workspace's latest app status and initialization phase.
+// Returns nil if no valid state can be determined.
+func deriveTaskCurrentState(
+	dbTask database.Task,
+	ws codersdk.Workspace,
+	taskAgentLifecycle *codersdk.WorkspaceAgentLifecycle,
+	taskAppHealth *codersdk.WorkspaceAppHealth,
+) *codersdk.TaskStateEntry {
+	var currentState *codersdk.TaskStateEntry
+
+	// Ignore 'latest app status' if it is older than the latest build and the
+	// latest build is a 'start' transition. This ensures that you don't show a
+	// stale app status from a previous build. For stop transitions, there is
+	// still value in showing the latest app status.
+	if ws.LatestAppStatus != nil {
+		if ws.LatestBuild.Transition != codersdk.WorkspaceTransitionStart || ws.LatestAppStatus.CreatedAt.After(ws.LatestBuild.CreatedAt) {
+			currentState = &codersdk.TaskStateEntry{
+				Timestamp: ws.LatestAppStatus.CreatedAt,
+				State:     codersdk.TaskState(ws.LatestAppStatus.State),
+				Message:   ws.LatestAppStatus.Message,
+				URI:       ws.LatestAppStatus.URI,
+			}
+		}
+	}
+
+	// If no valid agent state was found for the current build and the task is initializing,
+	// provide a descriptive initialization message.
+	if currentState == nil && dbTask.Status == database.TaskStatusInitializing {
+		message := "Initializing workspace"
+
+		switch {
+		case ws.LatestBuild.Status == codersdk.WorkspaceStatusPending ||
+			ws.LatestBuild.Status == codersdk.WorkspaceStatusStarting:
+			message = fmt.Sprintf("Workspace is %s", ws.LatestBuild.Status)
+		case taskAgentLifecycle != nil:
+			switch {
+			case *taskAgentLifecycle == codersdk.WorkspaceAgentLifecycleCreated:
+				message = "Agent is connecting"
+			case *taskAgentLifecycle == codersdk.WorkspaceAgentLifecycleStarting:
+				message = "Agent is starting"
+			case *taskAgentLifecycle == codersdk.WorkspaceAgentLifecycleReady:
+				if taskAppHealth != nil && *taskAppHealth == codersdk.WorkspaceAppHealthInitializing {
+					message = "App is initializing"
+				} else {
+					// In case the workspace app is not initializing,
+					// the overall task status should be updated accordingly
+					message = "Initializing workspace applications"
+				}
+			default:
+				// In case the workspace agent is not initializing,
+				// the overall task status should be updated accordingly
+				message = "Initializing workspace agent"
+			}
+		}
+
+		currentState = &codersdk.TaskStateEntry{
+			Timestamp: ws.LatestBuild.CreatedAt,
+			State:     codersdk.TaskStateWorking,
+			Message:   message,
+			URI:       "",
+		}
+	}
+
+	return currentState
+}
+
 // @Summary List AI tasks
 // @Description: EXPERIMENTAL: this endpoint is experimental and not guaranteed to be stable.
 // @ID list-tasks

coderd/aitasks_internal_test.go

@@ -0,0 +1,223 @@
+package coderd
+
+import (
+	"testing"
+	"time"
+
+	"github.com/google/uuid"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/coderd/database"
+	"github.com/coder/coder/v2/coderd/util/ptr"
+	"github.com/coder/coder/v2/codersdk"
+)
+
+func TestDeriveTaskCurrentState_Unit(t *testing.T) {
+	t.Parallel()
+
+	now := time.Now()
+	tests := []struct {
+		name               string
+		task               database.Task
+		agentLifecycle     *codersdk.WorkspaceAgentLifecycle
+		appHealth          *codersdk.WorkspaceAppHealth
+		latestAppStatus    *codersdk.WorkspaceAppStatus
+		latestBuild        codersdk.WorkspaceBuild
+		expectCurrentState bool
+		expectedTimestamp  time.Time
+		expectedState      codersdk.TaskState
+		expectedMessage    string
+	}{
+		{
+			name: "NoAppStatus",
+			task: database.Task{
+				ID:     uuid.New(),
+				Status: database.TaskStatusActive,
+			},
+			agentLifecycle:  nil,
+			appHealth:       nil,
+			latestAppStatus: nil,
+			latestBuild: codersdk.WorkspaceBuild{
+				Transition: codersdk.WorkspaceTransitionStart,
+				CreatedAt:  now,
+			},
+			expectCurrentState: false,
+		},
+		{
+			name: "BuildStartTransition_AppStatus_NewerThanBuild",
+			task: database.Task{
+				ID:     uuid.New(),
+				Status: database.TaskStatusActive,
+			},
+			agentLifecycle: nil,
+			appHealth:      nil,
+			latestAppStatus: &codersdk.WorkspaceAppStatus{
+				State:     codersdk.WorkspaceAppStatusStateWorking,
+				Message:   "Task is working",
+				CreatedAt: now.Add(1 * time.Minute),
+			},
+			latestBuild: codersdk.WorkspaceBuild{
+				Transition: codersdk.WorkspaceTransitionStart,
+				CreatedAt:  now,
+			},
+			expectCurrentState: true,
+			expectedTimestamp:  now.Add(1 * time.Minute),
+			expectedState:      codersdk.TaskState(codersdk.WorkspaceAppStatusStateWorking),
+			expectedMessage:    "Task is working",
+		},
+		{
+			name: "BuildStartTransition_StaleAppStatus_OlderThanBuild",
+			task: database.Task{
+				ID:     uuid.New(),
+				Status: database.TaskStatusActive,
+			},
+			agentLifecycle: nil,
+			appHealth:      nil,
+			latestAppStatus: &codersdk.WorkspaceAppStatus{
+				State:     codersdk.WorkspaceAppStatusStateComplete,
+				Message:   "Previous task completed",
+				CreatedAt: now.Add(-1 * time.Minute),
+			},
+			latestBuild: codersdk.WorkspaceBuild{
+				Transition: codersdk.WorkspaceTransitionStart,
+				CreatedAt:  now,
+			},
+			expectCurrentState: false,
+		},
+		{
+			name: "BuildStopTransition",
+			task: database.Task{
+				ID:     uuid.New(),
+				Status: database.TaskStatusActive,
+			},
+			agentLifecycle: nil,
+			appHealth:      nil,
+			latestAppStatus: &codersdk.WorkspaceAppStatus{
+				State:     codersdk.WorkspaceAppStatusStateComplete,
+				Message:   "Task completed before stop",
+				CreatedAt: now.Add(-1 * time.Minute),
+			},
+			latestBuild: codersdk.WorkspaceBuild{
+				Transition: codersdk.WorkspaceTransitionStop,
+				CreatedAt:  now,
+			},
+			expectCurrentState: true,
+			expectedTimestamp:  now.Add(-1 * time.Minute),
+			expectedState:      codersdk.TaskState(codersdk.WorkspaceAppStatusStateComplete),
+			expectedMessage:    "Task completed before stop",
+		},
+		{
+			name: "TaskInitializing_WorkspacePending",
+			task: database.Task{
+				ID:     uuid.New(),
+				Status: database.TaskStatusInitializing,
+			},
+			agentLifecycle:  nil,
+			appHealth:       nil,
+			latestAppStatus: nil,
+			latestBuild: codersdk.WorkspaceBuild{
+				Status:    codersdk.WorkspaceStatusPending,
+				CreatedAt: now,
+			},
+			expectCurrentState: true,
+			expectedTimestamp:  now,
+			expectedState:      codersdk.TaskStateWorking,
+			expectedMessage:    "Workspace is pending",
+		},
+		{
+			name: "TaskInitializing_WorkspaceStarting",
+			task: database.Task{
+				ID:     uuid.New(),
+				Status: database.TaskStatusInitializing,
+			},
+			agentLifecycle:  nil,
+			appHealth:       nil,
+			latestAppStatus: nil,
+			latestBuild: codersdk.WorkspaceBuild{
+				Status:    codersdk.WorkspaceStatusStarting,
+				CreatedAt: now,
+			},
+			expectCurrentState: true,
+			expectedTimestamp:  now,
+			expectedState:      codersdk.TaskStateWorking,
+			expectedMessage:    "Workspace is starting",
+		},
+		{
+			name: "TaskInitializing_AgentConnecting",
+			task: database.Task{
+				ID:     uuid.New(),
+				Status: database.TaskStatusInitializing,
+			},
+			agentLifecycle:  ptr.Ref(codersdk.WorkspaceAgentLifecycleCreated),
+			appHealth:       nil,
+			latestAppStatus: nil,
+			latestBuild: codersdk.WorkspaceBuild{
+				Status:    codersdk.WorkspaceStatusRunning,
+				CreatedAt: now,
+			},
+			expectCurrentState: true,
+			expectedTimestamp:  now,
+			expectedState:      codersdk.TaskStateWorking,
+			expectedMessage:    "Agent is connecting",
+		},
+		{
+			name: "TaskInitializing_AgentStarting",
+			task: database.Task{
+				ID:     uuid.New(),
+				Status: database.TaskStatusInitializing,
+			},
+			agentLifecycle:  ptr.Ref(codersdk.WorkspaceAgentLifecycleStarting),
+			appHealth:       nil,
+			latestAppStatus: nil,
+			latestBuild: codersdk.WorkspaceBuild{
+				Status:    codersdk.WorkspaceStatusRunning,
+				CreatedAt: now,
+			},
+			expectCurrentState: true,
+			expectedTimestamp:  now,
+			expectedState:      codersdk.TaskStateWorking,
+			expectedMessage:    "Agent is starting",
+		},
+		{
+			name: "TaskInitializing_AppInitializing",
+			task: database.Task{
+				ID:     uuid.New(),
+				Status: database.TaskStatusInitializing,
+			},
+			agentLifecycle:  ptr.Ref(codersdk.WorkspaceAgentLifecycleReady),
+			appHealth:       ptr.Ref(codersdk.WorkspaceAppHealthInitializing),
+			latestAppStatus: nil,
+			latestBuild: codersdk.WorkspaceBuild{
+				Status:    codersdk.WorkspaceStatusRunning,
+				CreatedAt: now,
+			},
+			expectCurrentState: true,
+			expectedTimestamp:  now,
+			expectedState:      codersdk.TaskStateWorking,
+			expectedMessage:    "App is initializing",
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			t.Parallel()
+
+			ws := codersdk.Workspace{
+				LatestBuild:     tt.latestBuild,
+				LatestAppStatus: tt.latestAppStatus,
+			}
+
+			currentState := deriveTaskCurrentState(tt.task, ws, tt.agentLifecycle, tt.appHealth)
+
+			if tt.expectCurrentState {
+				require.NotNil(t, currentState)
+				assert.Equal(t, tt.expectedTimestamp.UTC(), currentState.Timestamp.UTC())
+				assert.Equal(t, tt.expectedState, currentState.State)
+				assert.Equal(t, tt.expectedMessage, currentState.Message)
+			} else {
+				assert.Nil(t, currentState)
+			}
+		})
+	}
+}

coderd/aitasks_test.go

@@ -7,10 +7,8 @@ import (
 	"io"
 	"net/http"
 	"net/http/httptest"
-	"strings"
 	"testing"
 	"time"
-	"unicode/utf8"
 
 	"github.com/google/uuid"
 	"github.com/stretchr/testify/assert"
@@ -35,128 +33,6 @@ import (
 	"github.com/coder/coder/v2/testutil"
 )
 
-func TestAITasksPrompts(t *testing.T) {
-	t.Parallel()
-
-	t.Run("EmptyBuildIDs", func(t *testing.T) {
-		t.Parallel()
-		client := coderdtest.New(t, &coderdtest.Options{})
-		_ = coderdtest.CreateFirstUser(t, client)
-		experimentalClient := codersdk.NewExperimentalClient(client)
-
-		ctx := testutil.Context(t, testutil.WaitShort)
-
-		// Test with empty build IDs
-		prompts, err := experimentalClient.AITaskPrompts(ctx, []uuid.UUID{})
-		require.NoError(t, err)
-		require.Empty(t, prompts.Prompts)
-	})
-
-	t.Run("MultipleBuilds", func(t *testing.T) {
-		t.Parallel()
-
-		adminClient := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
-		first := coderdtest.CreateFirstUser(t, adminClient)
-		memberClient, _ := coderdtest.CreateAnotherUser(t, adminClient, first.OrganizationID)
-
-		ctx := testutil.Context(t, testutil.WaitLong)
-
-		// Create a template with parameters
-		version := coderdtest.CreateTemplateVersion(t, adminClient, first.OrganizationID, &echo.Responses{
-			Parse: echo.ParseComplete,
-			ProvisionPlan: []*proto.Response{{
-				Type: &proto.Response_Plan{
-					Plan: &proto.PlanComplete{
-						Parameters: []*proto.RichParameter{
-							{
-								Name:         "param1",
-								Type:         "string",
-								DefaultValue: "default1",
-							},
-							{
-								Name:         codersdk.AITaskPromptParameterName,
-								Type:         "string",
-								DefaultValue: "default2",
-							},
-						},
-					},
-				},
-			}},
-			ProvisionApply: echo.ApplyComplete,
-		})
-		template := coderdtest.CreateTemplate(t, adminClient, first.OrganizationID, version.ID)
-		coderdtest.AwaitTemplateVersionJobCompleted(t, adminClient, version.ID)
-
-		// Create two workspaces with different parameters
-		workspace1 := coderdtest.CreateWorkspace(t, memberClient, template.ID, func(request *codersdk.CreateWorkspaceRequest) {
-			request.RichParameterValues = []codersdk.WorkspaceBuildParameter{
-				{Name: "param1", Value: "value1a"},
-				{Name: codersdk.AITaskPromptParameterName, Value: "value2a"},
-			}
-		})
-		coderdtest.AwaitWorkspaceBuildJobCompleted(t, memberClient, workspace1.LatestBuild.ID)
-
-		workspace2 := coderdtest.CreateWorkspace(t, memberClient, template.ID, func(request *codersdk.CreateWorkspaceRequest) {
-			request.RichParameterValues = []codersdk.WorkspaceBuildParameter{
-				{Name: "param1", Value: "value1b"},
-				{Name: codersdk.AITaskPromptParameterName, Value: "value2b"},
-			}
-		})
-		coderdtest.AwaitWorkspaceBuildJobCompleted(t, memberClient, workspace2.LatestBuild.ID)
-
-		workspace3 := coderdtest.CreateWorkspace(t, adminClient, template.ID, func(request *codersdk.CreateWorkspaceRequest) {
-			request.RichParameterValues = []codersdk.WorkspaceBuildParameter{
-				{Name: "param1", Value: "value1c"},
-				{Name: codersdk.AITaskPromptParameterName, Value: "value2c"},
-			}
-		})
-		coderdtest.AwaitWorkspaceBuildJobCompleted(t, adminClient, workspace3.LatestBuild.ID)
-		allBuildIDs := []uuid.UUID{workspace1.LatestBuild.ID, workspace2.LatestBuild.ID, workspace3.LatestBuild.ID}
-
-		experimentalMemberClient := codersdk.NewExperimentalClient(memberClient)
-		// Test parameters endpoint as member
-		prompts, err := experimentalMemberClient.AITaskPrompts(ctx, allBuildIDs)
-		require.NoError(t, err)
-		// we expect 2 prompts because the member client does not have access to workspace3
-		// since it was created by the admin client
-		require.Len(t, prompts.Prompts, 2)
-
-		// Check workspace1 parameters
-		build1Prompt := prompts.Prompts[workspace1.LatestBuild.ID.String()]
-		require.Equal(t, "value2a", build1Prompt)
-
-		// Check workspace2 parameters
-		build2Prompt := prompts.Prompts[workspace2.LatestBuild.ID.String()]
-		require.Equal(t, "value2b", build2Prompt)
-
-		experimentalAdminClient := codersdk.NewExperimentalClient(adminClient)
-		// Test parameters endpoint as admin
-		// we expect 3 prompts because the admin client has access to all workspaces
-		prompts, err = experimentalAdminClient.AITaskPrompts(ctx, allBuildIDs)
-		require.NoError(t, err)
-		require.Len(t, prompts.Prompts, 3)
-
-		// Check workspace3 parameters
-		build3Prompt := prompts.Prompts[workspace3.LatestBuild.ID.String()]
-		require.Equal(t, "value2c", build3Prompt)
-	})
-
-	t.Run("NonExistentBuildIDs", func(t *testing.T) {
-		t.Parallel()
-		client := coderdtest.New(t, &coderdtest.Options{})
-		_ = coderdtest.CreateFirstUser(t, client)
-
-		ctx := testutil.Context(t, testutil.WaitShort)
-
-		// Test with non-existent build IDs
-		nonExistentID := uuid.New()
-		experimentalClient := codersdk.NewExperimentalClient(client)
-		prompts, err := experimentalClient.AITaskPrompts(ctx, []uuid.UUID{nonExistentID})
-		require.NoError(t, err)
-		require.Empty(t, prompts.Prompts)
-	})
-}
-
 func TestTasks(t *testing.T) {
 	t.Parallel()
 
@@ -188,7 +64,6 @@ func TestTasks(t *testing.T) {
 				{
 					Type: &proto.Response_Plan{
 						Plan: &proto.PlanComplete{
-							Parameters: []*proto.RichParameter{{Name: codersdk.AITaskPromptParameterName, Type: "string"}},
 							HasAiTasks: true,
 						},
 					},
@@ -259,6 +134,9 @@ func TestTasks(t *testing.T) {
 		// Wait for the workspace to be built.
 		workspace, err := client.Workspace(ctx, task.WorkspaceID.UUID)
 		require.NoError(t, err)
+		if assert.True(t, workspace.TaskID.Valid, "task id should be set on workspace") {
+			assert.Equal(t, task.ID, workspace.TaskID.UUID, "workspace task id should match")
+		}
 		coderdtest.AwaitWorkspaceBuildJobCompleted(t, client, workspace.LatestBuild.ID)
 
 		// List tasks via experimental API and verify the prompt and status mapping.
@@ -279,12 +157,13 @@ func TestTasks(t *testing.T) {
 		t.Parallel()
 
 		var (
-			client, db = coderdtest.NewWithDatabase(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
-			ctx        = testutil.Context(t, testutil.WaitLong)
-			user       = coderdtest.CreateFirstUser(t, client)
-			template   = createAITemplate(t, client, user)
-			wantPrompt = "review my code"
-			exp        = codersdk.NewExperimentalClient(client)
+			client, db     = coderdtest.NewWithDatabase(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
+			ctx            = testutil.Context(t, testutil.WaitLong)
+			user           = coderdtest.CreateFirstUser(t, client)
+			anotherUser, _ = coderdtest.CreateAnotherUser(t, client, user.OrganizationID)
+			template       = createAITemplate(t, client, user)
+			wantPrompt     = "review my code"
+			exp            = codersdk.NewExperimentalClient(client)
 		)
 
 		task, err := exp.CreateTask(ctx, "me", codersdk.CreateTaskRequest{
@@ -297,6 +176,9 @@ func TestTasks(t *testing.T) {
 		// Get the workspace and wait for it to be ready.
 		ws, err := client.Workspace(ctx, task.WorkspaceID.UUID)
 		require.NoError(t, err)
+		if assert.True(t, ws.TaskID.Valid, "task id should be set on workspace") {
+			assert.Equal(t, task.ID, ws.TaskID.UUID, "workspace task id should match")
+		}
 		coderdtest.AwaitWorkspaceBuildJobCompleted(t, client, ws.LatestBuild.ID)
 		ws = coderdtest.MustWorkspace(t, client, task.WorkspaceID.UUID)
 		// Assert invariant: the workspace has exactly one resource with one agent with one app.
@@ -331,6 +213,24 @@ func TestTasks(t *testing.T) {
 		assert.Equal(t, taskAppID, updated.WorkspaceAppID.UUID, "workspace app id should match")
 		assert.NotEmpty(t, updated.WorkspaceStatus, "task status should not be empty")
 
+		// Fetch the task by name and verify the same result
+		byName, err := exp.TaskByOwnerAndName(ctx, codersdk.Me, task.Name)
+		require.NoError(t, err)
+		require.Equal(t, byName, updated)
+
+		// Another member user should not be able to fetch the task
+		otherClient := codersdk.NewExperimentalClient(anotherUser)
+		_, err = otherClient.TaskByID(ctx, task.ID)
+		require.Error(t, err, "fetching task should fail by ID for another member user")
+		var sdkErr *codersdk.Error
+		require.ErrorAs(t, err, &sdkErr)
+		require.Equal(t, http.StatusNotFound, sdkErr.StatusCode())
+		// Also test by name
+		_, err = otherClient.TaskByOwnerAndName(ctx, task.OwnerName, task.Name)
+		require.Error(t, err, "fetching task should fail by name for another member user")
+		require.ErrorAs(t, err, &sdkErr)
+		require.Equal(t, http.StatusNotFound, sdkErr.StatusCode())
+
 		// Stop the workspace
 		coderdtest.MustTransitionWorkspace(t, client, task.WorkspaceID.UUID, codersdk.WorkspaceTransitionStart, codersdk.WorkspaceTransitionStop)
 
@@ -340,14 +240,18 @@ func TestTasks(t *testing.T) {
 		assert.NotNil(t, updated.CurrentState, "current state should not be nil")
 		assert.Equal(t, "all done", updated.CurrentState.Message)
 		assert.Equal(t, codersdk.TaskStateComplete, updated.CurrentState.State)
+		previousCurrentState := updated.CurrentState
 
 		// Start the workspace again
 		coderdtest.MustTransitionWorkspace(t, client, task.WorkspaceID.UUID, codersdk.WorkspaceTransitionStop, codersdk.WorkspaceTransitionStart)
 
-		// Verify that the status from the previous build is no longer present
+		// Verify that the status from the previous build has been cleared
+		// and replaced by the agent initialization status.
 		updated, err = exp.TaskByID(ctx, task.ID)
 		require.NoError(t, err)
-		assert.Nil(t, updated.CurrentState, "current state should be nil")
+		assert.NotEqual(t, previousCurrentState, updated.CurrentState)
+		assert.Equal(t, codersdk.TaskStateWorking, updated.CurrentState.State)
+		assert.NotEqual(t, "all done", updated.CurrentState.Message)
 	})
 
 	t.Run("Delete", func(t *testing.T) {
@@ -371,6 +275,9 @@ func TestTasks(t *testing.T) {
 			require.True(t, task.WorkspaceID.Valid, "task should have a workspace ID")
 			ws, err := client.Workspace(ctx, task.WorkspaceID.UUID)
 			require.NoError(t, err)
+			if assert.True(t, ws.TaskID.Valid, "task id should be set on workspace") {
+				assert.Equal(t, task.ID, ws.TaskID.UUID, "workspace task id should match")
+			}
 			coderdtest.AwaitWorkspaceBuildJobCompleted(t, client, ws.LatestBuild.ID)
 
 			err = exp.DeleteTask(ctx, "me", task.ID)
@@ -417,6 +324,9 @@ func TestTasks(t *testing.T) {
 			coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
 			template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID)
 			ws := coderdtest.CreateWorkspace(t, client, template.ID)
+			if assert.False(t, ws.TaskID.Valid, "task id should not be set on non-task workspace") {
+				assert.Zero(t, ws.TaskID, "non-task workspace task id should be empty")
+			}
 			coderdtest.AwaitWorkspaceBuildJobCompleted(t, client, ws.LatestBuild.ID)
 
 			exp := codersdk.NewExperimentalClient(client)
@@ -466,10 +376,10 @@ func TestTasks(t *testing.T) {
 			}
 		})
 
-		t.Run("NoWorkspace", func(t *testing.T) {
+		t.Run("DeletedWorkspace", func(t *testing.T) {
 			t.Parallel()
 
-			client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
+			client, db := coderdtest.NewWithDatabase(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
 			user := coderdtest.CreateFirstUser(t, client)
 			template := createAITemplate(t, client, user)
 			ctx := testutil.Context(t, testutil.WaitLong)
@@ -483,14 +393,54 @@ func TestTasks(t *testing.T) {
 			ws, err := client.Workspace(ctx, task.WorkspaceID.UUID)
 			require.NoError(t, err)
 			coderdtest.AwaitWorkspaceBuildJobCompleted(t, client, ws.LatestBuild.ID)
-			// Delete the task workspace
-			coderdtest.MustTransitionWorkspace(t, client, ws.ID, codersdk.WorkspaceTransitionStart, codersdk.WorkspaceTransitionDelete)
-			// We should still be able to fetch the task after deleting its workspace
+
+			// Mark the workspace as deleted directly in the database, bypassing provisionerd.
+			require.NoError(t, db.UpdateWorkspaceDeletedByID(dbauthz.AsProvisionerd(ctx), database.UpdateWorkspaceDeletedByIDParams{
+				ID:      ws.ID,
+				Deleted: true,
+			}))
+			// We should still be able to fetch the task if its workspace was deleted.
+			// Provisionerdserver will attempt delete the related task when deleting a workspace.
+			// This test ensures that we can still handle the case where, for some reason, the
+			// task has not been marked as deleted, but the workspace has.
 			task, err = exp.TaskByID(ctx, task.ID)
-			require.NoError(t, err, "fetching a task should still work after deleting its related workspace")
+			require.NoError(t, err, "fetching a task should still work if its related workspace is deleted")
 			err = exp.DeleteTask(ctx, task.OwnerID.String(), task.ID)
 			require.NoError(t, err, "should be possible to delete a task with no workspace")
 		})
+
+		t.Run("DeletingTaskWorkspaceDeletesTask", func(t *testing.T) {
+			t.Parallel()
+
+			client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
+			user := coderdtest.CreateFirstUser(t, client)
+			template := createAITemplate(t, client, user)
+
+			ctx := testutil.Context(t, testutil.WaitLong)
+
+			exp := codersdk.NewExperimentalClient(client)
+			task, err := exp.CreateTask(ctx, "me", codersdk.CreateTaskRequest{
+				TemplateVersionID: template.ActiveVersionID,
+				Input:             "delete me",
+			})
+			require.NoError(t, err)
+			require.True(t, task.WorkspaceID.Valid, "task should have a workspace ID")
+			ws, err := client.Workspace(ctx, task.WorkspaceID.UUID)
+			require.NoError(t, err)
+			if assert.True(t, ws.TaskID.Valid, "task id should be set on workspace") {
+				assert.Equal(t, task.ID, ws.TaskID.UUID, "workspace task id should match")
+			}
+			coderdtest.AwaitWorkspaceBuildJobCompleted(t, client, ws.LatestBuild.ID)
+
+			// When; the task workspace is deleted
+			coderdtest.MustTransitionWorkspace(t, client, ws.ID, codersdk.WorkspaceTransitionStart, codersdk.WorkspaceTransitionDelete)
+			// Then: the task associated with the workspace is also deleted
+			_, err = exp.TaskByID(ctx, task.ID)
+			require.Error(t, err, "expected an error fetching the task")
+			var sdkErr *codersdk.Error
+			require.ErrorAs(t, err, &sdkErr, "expected a codersdk.Error")
+			require.Equal(t, http.StatusNotFound, sdkErr.StatusCode())
+		})
 	})
 
 	t.Run("Send", func(t *testing.T) {
@@ -728,7 +678,7 @@ func TestTasks(t *testing.T) {
 		coderdtest.AwaitWorkspaceBuildJobCompleted(t, client, ws.LatestBuild.ID)
 
 		// Fetch the task by ID via experimental API and verify fields.
-		task, err = exp.TaskByID(ctx, task.ID)
+		task, err = exp.TaskByIdentifier(ctx, task.ID.String())
 		require.NoError(t, err)
 		require.NotZero(t, task.WorkspaceBuildNumber)
 		require.True(t, task.WorkspaceAgentID.Valid)
@@ -805,6 +755,51 @@ func TestTasksCreate(t *testing.T) {
 		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
 		user := coderdtest.CreateFirstUser(t, client)
 
+		version := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, &echo.Responses{
+			Parse:          echo.ParseComplete,
+			ProvisionApply: echo.ApplyComplete,
+			ProvisionPlan: []*proto.Response{
+				{Type: &proto.Response_Plan{Plan: &proto.PlanComplete{
+					HasAiTasks: true,
+				}}},
+			},
+		})
+		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
+		template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID)
+
+		expClient := codersdk.NewExperimentalClient(client)
+
+		task, err := expClient.CreateTask(ctx, "me", codersdk.CreateTaskRequest{
+			TemplateVersionID: template.ActiveVersionID,
+			Input:             taskPrompt,
+		})
+		require.NoError(t, err)
+		require.True(t, task.WorkspaceID.Valid)
+
+		ws, err := client.Workspace(ctx, task.WorkspaceID.UUID)
+		require.NoError(t, err)
+		coderdtest.AwaitWorkspaceBuildJobCompleted(t, client, ws.LatestBuild.ID)
+
+		assert.NotEmpty(t, task.Name)
+		assert.Equal(t, template.ID, task.TemplateID)
+
+		parameters, err := client.WorkspaceBuildParameters(ctx, ws.LatestBuild.ID)
+		require.NoError(t, err)
+		require.Len(t, parameters, 0)
+	})
+
+	t.Run("OK AIPromptBackCompat", func(t *testing.T) {
+		t.Parallel()
+
+		var (
+			ctx = testutil.Context(t, testutil.WaitShort)
+
+			taskPrompt = "Some task prompt"
+		)
+
+		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
+		user := coderdtest.CreateFirstUser(t, client)
+
 		// Given: A template with an "AI Prompt" parameter
 		version := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, &echo.Responses{
 			Parse:          echo.ParseComplete,
@@ -884,7 +879,6 @@ func TestTasksCreate(t *testing.T) {
 						ProvisionApply: echo.ApplyComplete,
 						ProvisionPlan: []*proto.Response{
 							{Type: &proto.Response_Plan{Plan: &proto.PlanComplete{
-								Parameters: []*proto.RichParameter{{Name: codersdk.AITaskPromptParameterName, Type: "string"}},
 								HasAiTasks: true,
 							}}},
 						},
@@ -1000,7 +994,6 @@ func TestTasksCreate(t *testing.T) {
 			ProvisionApply: echo.ApplyComplete,
 			ProvisionPlan: []*proto.Response{
 				{Type: &proto.Response_Plan{Plan: &proto.PlanComplete{
-					Parameters: []*proto.RichParameter{{Name: codersdk.AITaskPromptParameterName, Type: "string"}},
 					HasAiTasks: true,
 				}}},
 			},
@@ -1060,7 +1053,6 @@ func TestTasksCreate(t *testing.T) {
 			ProvisionApply: echo.ApplyComplete,
 			ProvisionPlan: []*proto.Response{
 				{Type: &proto.Response_Plan{Plan: &proto.PlanComplete{
-					Parameters: []*proto.RichParameter{{Name: codersdk.AITaskPromptParameterName, Type: "string"}},
 					HasAiTasks: true,
 				}}},
 			},
@@ -1097,7 +1089,6 @@ func TestTasksCreate(t *testing.T) {
 			ProvisionApply: echo.ApplyComplete,
 			ProvisionPlan: []*proto.Response{
 				{Type: &proto.Response_Plan{Plan: &proto.PlanComplete{
-					Parameters: []*proto.RichParameter{{Name: codersdk.AITaskPromptParameterName, Type: "string"}},
 					HasAiTasks: true,
 				}}},
 			},
@@ -1150,7 +1141,6 @@ func TestTasksCreate(t *testing.T) {
 			ProvisionApply: echo.ApplyComplete,
 			ProvisionPlan: []*proto.Response{
 				{Type: &proto.Response_Plan{Plan: &proto.PlanComplete{
-					Parameters: []*proto.RichParameter{{Name: codersdk.AITaskPromptParameterName, Type: "string"}},
 					HasAiTasks: true,
 				}}},
 			},
@@ -1163,7 +1153,6 @@ func TestTasksCreate(t *testing.T) {
 			ProvisionApply: echo.ApplyComplete,
 			ProvisionPlan: []*proto.Response{
 				{Type: &proto.Response_Plan{Plan: &proto.PlanComplete{
-					Parameters: []*proto.RichParameter{{Name: codersdk.AITaskPromptParameterName, Type: "string"}},
 					HasAiTasks: true,
 				}}},
 			},
@@ -1200,6 +1189,7 @@ func TestTasksNotification(t *testing.T) {
 		isNotificationSent   bool
 		notificationTemplate uuid.UUID
 		taskPrompt           string
+		agentLifecycle       database.WorkspaceAgentLifecycleState
 	}{
 		// Should not send a notification when the agent app is not an AI task.
 		{
@@ -1247,6 +1237,7 @@ func TestTasksNotification(t *testing.T) {
 			isNotificationSent:   true,
 			notificationTemplate: notifications.TemplateTaskIdle,
 			taskPrompt:           "InitialTemplateTaskIdle",
+			agentLifecycle:       database.WorkspaceAgentLifecycleStateReady,
 		},
 		// Should send TemplateTaskWorking when the AI task transitions to 'Working' from 'Idle'.
 		{
@@ -1260,6 +1251,7 @@ func TestTasksNotification(t *testing.T) {
 			isNotificationSent:   true,
 			notificationTemplate: notifications.TemplateTaskWorking,
 			taskPrompt:           "TemplateTaskWorkingFromIdle",
+			agentLifecycle:       database.WorkspaceAgentLifecycleStateReady,
 		},
 		// Should send TemplateTaskIdle when the AI task transitions to 'Idle'.
 		{
@@ -1270,6 +1262,7 @@ func TestTasksNotification(t *testing.T) {
 			isNotificationSent:   true,
 			notificationTemplate: notifications.TemplateTaskIdle,
 			taskPrompt:           "TemplateTaskIdle",
+			agentLifecycle:       database.WorkspaceAgentLifecycleStateReady,
 		},
 		// Long task prompts should be truncated to 160 characters.
 		{
@@ -1280,6 +1273,7 @@ func TestTasksNotification(t *testing.T) {
 			isNotificationSent:   true,
 			notificationTemplate: notifications.TemplateTaskIdle,
 			taskPrompt:           "This is a very long task prompt that should be truncated to 160 characters. Lorem ipsum dolor sit amet, consectetur adipiscing elit. Sed do eiusmod tempor incididunt ut labore et dolore magna aliqua.",
+			agentLifecycle:       database.WorkspaceAgentLifecycleStateReady,
 		},
 		// Should send TemplateTaskCompleted when the AI task transitions to 'Complete'.
 		{
@@ -1290,6 +1284,7 @@ func TestTasksNotification(t *testing.T) {
 			isNotificationSent:   true,
 			notificationTemplate: notifications.TemplateTaskCompleted,
 			taskPrompt:           "TemplateTaskCompleted",
+			agentLifecycle:       database.WorkspaceAgentLifecycleStateReady,
 		},
 		// Should send TemplateTaskFailed when the AI task transitions to 'Failure'.
 		{
@@ -1300,6 +1295,7 @@ func TestTasksNotification(t *testing.T) {
 			isNotificationSent:   true,
 			notificationTemplate: notifications.TemplateTaskFailed,
 			taskPrompt:           "TemplateTaskFailed",
+			agentLifecycle:       database.WorkspaceAgentLifecycleStateReady,
 		},
 		// Should send TemplateTaskCompleted when the AI task transitions from 'Idle' to 'Complete'.
 		{
@@ -1310,6 +1306,7 @@ func TestTasksNotification(t *testing.T) {
 			isNotificationSent:   true,
 			notificationTemplate: notifications.TemplateTaskCompleted,
 			taskPrompt:           "TemplateTaskCompletedFromIdle",
+			agentLifecycle:       database.WorkspaceAgentLifecycleStateReady,
 		},
 		// Should send TemplateTaskFailed when the AI task transitions from 'Idle' to 'Failure'.
 		{
@@ -1320,6 +1317,7 @@ func TestTasksNotification(t *testing.T) {
 			isNotificationSent:   true,
 			notificationTemplate: notifications.TemplateTaskFailed,
 			taskPrompt:           "TemplateTaskFailedFromIdle",
+			agentLifecycle:       database.WorkspaceAgentLifecycleStateReady,
 		},
 		// Should NOT send notification when transitioning from 'Complete' to 'Complete' (no change).
 		{
@@ -1339,6 +1337,37 @@ func TestTasksNotification(t *testing.T) {
 			isNotificationSent: false,
 			taskPrompt:         "NoNotificationFailureToFailure",
 		},
+		// Should NOT send notification when agent is in 'starting' lifecycle state (agent startup).
+		{
+			name:               "AgentStarting_NoNotification",
+			latestAppStatuses:  nil,
+			newAppStatus:       codersdk.WorkspaceAppStatusStateIdle,
+			isAITask:           true,
+			isNotificationSent: false,
+			taskPrompt:         "AgentStarting_NoNotification",
+			agentLifecycle:     database.WorkspaceAgentLifecycleStateStarting,
+		},
+		// Should NOT send notification when agent is in 'created' lifecycle state (agent not started).
+		{
+			name:               "AgentCreated_NoNotification",
+			latestAppStatuses:  []codersdk.WorkspaceAppStatusState{codersdk.WorkspaceAppStatusStateWorking},
+			newAppStatus:       codersdk.WorkspaceAppStatusStateIdle,
+			isAITask:           true,
+			isNotificationSent: false,
+			taskPrompt:         "AgentCreated_NoNotification",
+			agentLifecycle:     database.WorkspaceAgentLifecycleStateCreated,
+		},
+		// Should send notification when agent is in 'ready' lifecycle state (agent fully started).
+		{
+			name:                 "AgentReady_SendNotification",
+			latestAppStatuses:    []codersdk.WorkspaceAppStatusState{codersdk.WorkspaceAppStatusStateWorking},
+			newAppStatus:         codersdk.WorkspaceAppStatusStateIdle,
+			isAITask:             true,
+			isNotificationSent:   true,
+			notificationTemplate: notifications.TemplateTaskIdle,
+			taskPrompt:           "AgentReady_SendNotification",
+			agentLifecycle:       database.WorkspaceAgentLifecycleStateReady,
+		},
 	} {
 		t.Run(tc.name, func(t *testing.T) {
 			t.Parallel()
@@ -1357,31 +1386,57 @@ func TestTasksNotification(t *testing.T) {
 			// Given: a workspace build with an agent containing an App
 			workspaceAgentAppID := uuid.New()
 			workspaceBuildID := uuid.New()
-			workspaceBuildSeed := database.WorkspaceBuild{
-				ID: workspaceBuildID,
-			}
-			if tc.isAITask {
-				workspaceBuildSeed = database.WorkspaceBuild{
-					ID: workspaceBuildID,
-					// AI Task configuration
-					HasAITask:          sql.NullBool{Bool: true, Valid: true},
-					AITaskSidebarAppID: uuid.NullUUID{UUID: workspaceAgentAppID, Valid: true},
-				}
-			}
-			workspaceBuild := dbfake.WorkspaceBuild(t, db, database.WorkspaceTable{
+			workspaceBuilder := dbfake.WorkspaceBuild(t, db, database.WorkspaceTable{
 				OrganizationID: ownerUser.OrganizationID,
 				OwnerID:        memberUser.ID,
-			}).Seed(workspaceBuildSeed).Params(database.WorkspaceBuildParameter{
-				WorkspaceBuildID: workspaceBuildID,
-				Name:             codersdk.AITaskPromptParameterName,
-				Value:            tc.taskPrompt,
-			}).WithAgent(func(agent []*proto.Agent) []*proto.Agent {
-				agent[0].Apps = []*proto.App{{
-					Id:   workspaceAgentAppID.String(),
-					Slug: "ccw",
-				}}
-				return agent
-			}).Do()
+			}).Seed(database.WorkspaceBuild{
+				ID: workspaceBuildID,
+			})
+			if tc.isAITask {
+				workspaceBuilder = workspaceBuilder.
+					WithTask(database.TaskTable{
+						Prompt: tc.taskPrompt,
+					}, &proto.App{
+						Id:   workspaceAgentAppID.String(),
+						Slug: "ccw",
+					})
+			} else {
+				workspaceBuilder = workspaceBuilder.
+					WithAgent(func(agent []*proto.Agent) []*proto.Agent {
+						agent[0].Apps = []*proto.App{{
+							Id:   workspaceAgentAppID.String(),
+							Slug: "ccw",
+						}}
+						return agent
+					})
+			}
+			workspaceBuild := workspaceBuilder.Do()
+
+			// Given: set the agent lifecycle state if specified
+			if tc.agentLifecycle != "" {
+				workspace := coderdtest.MustWorkspace(t, client, workspaceBuild.Workspace.ID)
+				agentID := workspace.LatestBuild.Resources[0].Agents[0].ID
+
+				var (
+					startedAt sql.NullTime
+					readyAt   sql.NullTime
+				)
+				if tc.agentLifecycle == database.WorkspaceAgentLifecycleStateReady {
+					startedAt = sql.NullTime{Time: dbtime.Now(), Valid: true}
+					readyAt = sql.NullTime{Time: dbtime.Now(), Valid: true}
+				} else if tc.agentLifecycle == database.WorkspaceAgentLifecycleStateStarting {
+					startedAt = sql.NullTime{Time: dbtime.Now(), Valid: true}
+				}
+
+				// nolint:gocritic // This is a system restricted operation for test setup.
+				err := db.UpdateWorkspaceAgentLifecycleStateByID(dbauthz.AsSystemRestricted(ctx), database.UpdateWorkspaceAgentLifecycleStateByIDParams{
+					ID:             agentID,
+					LifecycleState: tc.agentLifecycle,
+					StartedAt:      startedAt,
+					ReadyAt:        readyAt,
+				})
+				require.NoError(t, err)
+			}
 
 			// Given: the workspace agent app has previous statuses
 			agentClient := agentsdk.New(client.URL, agentsdk.WithFixedToken(workspaceBuild.AgentToken))
@@ -1422,13 +1477,7 @@ func TestTasksNotification(t *testing.T) {
 				require.Len(t, sent, 1)
 				require.Equal(t, memberUser.ID, sent[0].UserID)
 				require.Len(t, sent[0].Labels, 2)
-				// NOTE: len(string) is the number of bytes in the string, not the number of runes.
-				require.LessOrEqual(t, utf8.RuneCountInString(sent[0].Labels["task"]), 160)
-				if len(tc.taskPrompt) > 160 {
-					require.Contains(t, tc.taskPrompt, strings.TrimSuffix(sent[0].Labels["task"], "…"))
-				} else {
-					require.Equal(t, tc.taskPrompt, sent[0].Labels["task"])
-				}
+				require.Equal(t, workspaceBuild.Task.Name, sent[0].Labels["task"])
 				require.Equal(t, workspace.Name, sent[0].Labels["workspace"])
 			} else {
 				// Then: No notification is sent

coderd/apidoc/docs.go

@@ -85,7 +85,7 @@ const docTemplate = `{
                 }
             }
         },
-        "/api/experimental/aibridge/interceptions": {
+        "/aibridge/interceptions": {
             "get": {
                 "security": [
                     {
@@ -96,10 +96,10 @@ const docTemplate = `{
                     "application/json"
                 ],
                 "tags": [
-                    "AIBridge"
+                    "AI Bridge"
                 ],
-                "summary": "List AIBridge interceptions",
-                "operationId": "list-aibridge-interceptions",
+                "summary": "List AI Bridge interceptions",
+                "operationId": "list-ai-bridge-interceptions",
                 "parameters": [
                     {
                         "type": "string",
@@ -6002,6 +6002,41 @@ const docTemplate = `{
                 }
             }
         },
+        "/templates/{template}/prebuilds/invalidate": {
+            "post": {
+                "security": [
+                    {
+                        "CoderSessionToken": []
+                    }
+                ],
+                "produces": [
+                    "application/json"
+                ],
+                "tags": [
+                    "Enterprise"
+                ],
+                "summary": "Invalidate presets for template",
+                "operationId": "invalidate-presets-for-template",
+                "parameters": [
+                    {
+                        "type": "string",
+                        "format": "uuid",
+                        "description": "Template ID",
+                        "name": "template",
+                        "in": "path",
+                        "required": true
+                    }
+                ],
+                "responses": {
+                    "200": {
+                        "description": "OK",
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.InvalidatePresetsResponse"
+                        }
+                    }
+                }
+            }
+        },
         "/templates/{template}/versions": {
             "get": {
                 "security": [
@@ -11668,23 +11703,55 @@ const docTemplate = `{
                 }
             }
         },
+        "codersdk.AIBridgeBedrockConfig": {
+            "type": "object",
+            "properties": {
+                "access_key": {
+                    "type": "string"
+                },
+                "access_key_secret": {
+                    "type": "string"
+                },
+                "model": {
+                    "type": "string"
+                },
+                "region": {
+                    "type": "string"
+                },
+                "small_fast_model": {
+                    "type": "string"
+                }
+            }
+        },
         "codersdk.AIBridgeConfig": {
             "type": "object",
             "properties": {
                 "anthropic": {
                     "$ref": "#/definitions/codersdk.AIBridgeAnthropicConfig"
                 },
+                "bedrock": {
+                    "$ref": "#/definitions/codersdk.AIBridgeBedrockConfig"
+                },
                 "enabled": {
                     "type": "boolean"
                 },
+                "inject_coder_mcp_tools": {
+                    "type": "boolean"
+                },
                 "openai": {
                     "$ref": "#/definitions/codersdk.AIBridgeOpenAIConfig"
+                },
+                "retention": {
+                    "type": "integer"
                 }
             }
         },
         "codersdk.AIBridgeInterception": {
             "type": "object",
             "properties": {
+                "api_key_id": {
+                    "type": "string"
+                },
                 "ended_at": {
                     "type": "string",
                     "format": "date-time"
@@ -14294,15 +14361,15 @@ const docTemplate = `{
                 "oauth2",
                 "mcp-server-http",
                 "workspace-sharing",
-                "aibridge"
+                "terraform-directory-reuse"
             ],
             "x-enum-comments": {
-                "ExperimentAIBridge": "Enables AI Bridge functionality.",
                 "ExperimentAutoFillParameters": "This should not be taken out of experiments until we have redesigned the feature.",
                 "ExperimentExample": "This isn't used for anything.",
                 "ExperimentMCPServerHTTP": "Enables the MCP HTTP server functionality.",
                 "ExperimentNotifications": "Sends notifications via SMTP and webhooks following certain events.",
                 "ExperimentOAuth2": "Enables OAuth2 provider functionality.",
+                "ExperimentTerraformWorkspace": "Enables reuse of existing terraform directory for builds",
                 "ExperimentWebPush": "Enables web push notifications through the browser.",
                 "ExperimentWorkspaceSharing": "Enables updating workspace ACLs for sharing with users and groups.",
                 "ExperimentWorkspaceUsage": "Enables the new workspace usage tracking."
@@ -14316,7 +14383,7 @@ const docTemplate = `{
                 "ExperimentOAuth2",
                 "ExperimentMCPServerHTTP",
                 "ExperimentWorkspaceSharing",
-                "ExperimentAIBridge"
+                "ExperimentTerraformWorkspace"
             ]
         },
         "codersdk.ExternalAPIKeyScopes": {
@@ -14860,6 +14927,31 @@ const docTemplate = `{
                 "InsightsReportIntervalWeek"
             ]
         },
+        "codersdk.InvalidatePresetsResponse": {
+            "type": "object",
+            "properties": {
+                "invalidated": {
+                    "type": "array",
+                    "items": {
+                        "$ref": "#/definitions/codersdk.InvalidatedPreset"
+                    }
+                }
+            }
+        },
+        "codersdk.InvalidatedPreset": {
+            "type": "object",
+            "properties": {
+                "preset_name": {
+                    "type": "string"
+                },
+                "template_name": {
+                    "type": "string"
+                },
+                "template_version_name": {
+                    "type": "string"
+                }
+            }
+        },
         "codersdk.IssueReconnectingPTYSignedTokenRequest": {
             "type": "object",
             "required": [
@@ -15415,6 +15507,9 @@ const docTemplate = `{
                         "type": "string"
                     }
                 },
+                "revocation_endpoint": {
+                    "type": "string"
+                },
                 "scopes_supported": {
                     "type": "array",
                     "items": {
@@ -18106,6 +18201,9 @@ const docTemplate = `{
                 },
                 "use_classic_parameter_flow": {
                     "type": "boolean"
+                },
+                "use_terraform_workspace_cache": {
+                    "type": "boolean"
                 }
             }
         },
@@ -19034,6 +19132,10 @@ const docTemplate = `{
                 "use_classic_parameter_flow": {
                     "description": "UseClassicParameterFlow is a flag that switches the default behavior to use the classic\nparameter flow when creating a workspace. This only affects deployments with the experiment\n\"dynamic-parameters\" enabled. This setting will live for a period after the experiment is\nmade the default.\nAn \"opt-out\" is present in case the new feature breaks some existing templates.",
                     "type": "boolean"
+                },
+                "use_terraform_workspace_cache": {
+                    "description": "UseTerraformWorkspaceCache allows optionally specifying whether to use cached\nterraform directories for workspaces created from this template. This field\nonly applies when the correct experiment is enabled. This field is subject to\nbeing removed in the future.",
+                    "type": "boolean"
                 }
             }
         },
@@ -19692,6 +19794,14 @@ const docTemplate = `{
                     "description": "OwnerName is the username of the owner of the workspace.",
                     "type": "string"
                 },
+                "task_id": {
+                    "description": "TaskID, if set, indicates that the workspace is relevant to the given codersdk.Task.",
+                    "allOf": [
+                        {
+                            "$ref": "#/definitions/uuid.NullUUID"
+                        }
+                    ]
+                },
                 "template_active_version_id": {
                     "type": "string",
                     "format": "uuid"
@@ -20498,11 +20608,6 @@ const docTemplate = `{
         "codersdk.WorkspaceBuild": {
             "type": "object",
             "properties": {
-                "ai_task_sidebar_app_id": {
-                    "description": "Deprecated: This field has been replaced with ` + "`" + `TaskAppID` + "`" + `",
-                    "type": "string",
-                    "format": "uuid"
-                },
                 "build_number": {
                     "type": "integer"
                 },
@@ -20518,6 +20623,7 @@ const docTemplate = `{
                     "format": "date-time"
                 },
                 "has_ai_task": {
+                    "description": "Deprecated: This field has been deprecated in favor of Task WorkspaceID.",
                     "type": "boolean"
                 },
                 "has_external_agent": {
@@ -20581,10 +20687,6 @@ const docTemplate = `{
                         }
                     ]
                 },
-                "task_app_id": {
-                    "type": "string",
-                    "format": "uuid"
-                },
                 "template_version_id": {
                     "type": "string",
                     "format": "uuid"

coderd/apidoc/swagger.json

@@ -65,7 +65,7 @@
 				}
 			}
 		},
-		"/api/experimental/aibridge/interceptions": {
+		"/aibridge/interceptions": {
 			"get": {
 				"security": [
 					{
@@ -73,9 +73,9 @@
 					}
 				],
 				"produces": ["application/json"],
-				"tags": ["AIBridge"],
-				"summary": "List AIBridge interceptions",
-				"operationId": "list-aibridge-interceptions",
+				"tags": ["AI Bridge"],
+				"summary": "List AI Bridge interceptions",
+				"operationId": "list-ai-bridge-interceptions",
 				"parameters": [
 					{
 						"type": "string",
@@ -5309,6 +5309,37 @@
 				}
 			}
 		},
+		"/templates/{template}/prebuilds/invalidate": {
+			"post": {
+				"security": [
+					{
+						"CoderSessionToken": []
+					}
+				],
+				"produces": ["application/json"],
+				"tags": ["Enterprise"],
+				"summary": "Invalidate presets for template",
+				"operationId": "invalidate-presets-for-template",
+				"parameters": [
+					{
+						"type": "string",
+						"format": "uuid",
+						"description": "Template ID",
+						"name": "template",
+						"in": "path",
+						"required": true
+					}
+				],
+				"responses": {
+					"200": {
+						"description": "OK",
+						"schema": {
+							"$ref": "#/definitions/codersdk.InvalidatePresetsResponse"
+						}
+					}
+				}
+			}
+		},
 		"/templates/{template}/versions": {
 			"get": {
 				"security": [
@@ -10364,23 +10395,55 @@
 				}
 			}
 		},
+		"codersdk.AIBridgeBedrockConfig": {
+			"type": "object",
+			"properties": {
+				"access_key": {
+					"type": "string"
+				},
+				"access_key_secret": {
+					"type": "string"
+				},
+				"model": {
+					"type": "string"
+				},
+				"region": {
+					"type": "string"
+				},
+				"small_fast_model": {
+					"type": "string"
+				}
+			}
+		},
 		"codersdk.AIBridgeConfig": {
 			"type": "object",
 			"properties": {
 				"anthropic": {
 					"$ref": "#/definitions/codersdk.AIBridgeAnthropicConfig"
 				},
+				"bedrock": {
+					"$ref": "#/definitions/codersdk.AIBridgeBedrockConfig"
+				},
 				"enabled": {
 					"type": "boolean"
 				},
+				"inject_coder_mcp_tools": {
+					"type": "boolean"
+				},
 				"openai": {
 					"$ref": "#/definitions/codersdk.AIBridgeOpenAIConfig"
+				},
+				"retention": {
+					"type": "integer"
 				}
 			}
 		},
 		"codersdk.AIBridgeInterception": {
 			"type": "object",
 			"properties": {
+				"api_key_id": {
+					"type": "string"
+				},
 				"ended_at": {
 					"type": "string",
 					"format": "date-time"
@@ -12901,15 +12964,15 @@
 				"oauth2",
 				"mcp-server-http",
 				"workspace-sharing",
-				"aibridge"
+				"terraform-directory-reuse"
 			],
 			"x-enum-comments": {
-				"ExperimentAIBridge": "Enables AI Bridge functionality.",
 				"ExperimentAutoFillParameters": "This should not be taken out of experiments until we have redesigned the feature.",
 				"ExperimentExample": "This isn't used for anything.",
 				"ExperimentMCPServerHTTP": "Enables the MCP HTTP server functionality.",
 				"ExperimentNotifications": "Sends notifications via SMTP and webhooks following certain events.",
 				"ExperimentOAuth2": "Enables OAuth2 provider functionality.",
+				"ExperimentTerraformWorkspace": "Enables reuse of existing terraform directory for builds",
 				"ExperimentWebPush": "Enables web push notifications through the browser.",
 				"ExperimentWorkspaceSharing": "Enables updating workspace ACLs for sharing with users and groups.",
 				"ExperimentWorkspaceUsage": "Enables the new workspace usage tracking."
@@ -12923,7 +12986,7 @@
 				"ExperimentOAuth2",
 				"ExperimentMCPServerHTTP",
 				"ExperimentWorkspaceSharing",
-				"ExperimentAIBridge"
+				"ExperimentTerraformWorkspace"
 			]
 		},
 		"codersdk.ExternalAPIKeyScopes": {
@@ -13458,6 +13521,31 @@
 				"InsightsReportIntervalWeek"
 			]
 		},
+		"codersdk.InvalidatePresetsResponse": {
+			"type": "object",
+			"properties": {
+				"invalidated": {
+					"type": "array",
+					"items": {
+						"$ref": "#/definitions/codersdk.InvalidatedPreset"
+					}
+				}
+			}
+		},
+		"codersdk.InvalidatedPreset": {
+			"type": "object",
+			"properties": {
+				"preset_name": {
+					"type": "string"
+				},
+				"template_name": {
+					"type": "string"
+				},
+				"template_version_name": {
+					"type": "string"
+				}
+			}
+		},
 		"codersdk.IssueReconnectingPTYSignedTokenRequest": {
 			"type": "object",
 			"required": ["agentID", "url"],
@@ -13969,6 +14057,9 @@
 						"type": "string"
 					}
 				},
+				"revocation_endpoint": {
+					"type": "string"
+				},
 				"scopes_supported": {
 					"type": "array",
 					"items": {
@@ -16581,6 +16672,9 @@
 				},
 				"use_classic_parameter_flow": {
 					"type": "boolean"
+				},
+				"use_terraform_workspace_cache": {
+					"type": "boolean"
 				}
 			}
 		},
@@ -17465,6 +17559,10 @@
 				"use_classic_parameter_flow": {
 					"description": "UseClassicParameterFlow is a flag that switches the default behavior to use the classic\nparameter flow when creating a workspace. This only affects deployments with the experiment\n\"dynamic-parameters\" enabled. This setting will live for a period after the experiment is\nmade the default.\nAn \"opt-out\" is present in case the new feature breaks some existing templates.",
 					"type": "boolean"
+				},
+				"use_terraform_workspace_cache": {
+					"description": "UseTerraformWorkspaceCache allows optionally specifying whether to use cached\nterraform directories for workspaces created from this template. This field\nonly applies when the correct experiment is enabled. This field is subject to\nbeing removed in the future.",
+					"type": "boolean"
 				}
 			}
 		},
@@ -18078,6 +18176,14 @@
 					"description": "OwnerName is the username of the owner of the workspace.",
 					"type": "string"
 				},
+				"task_id": {
+					"description": "TaskID, if set, indicates that the workspace is relevant to the given codersdk.Task.",
+					"allOf": [
+						{
+							"$ref": "#/definitions/uuid.NullUUID"
+						}
+					]
+				},
 				"template_active_version_id": {
 					"type": "string",
 					"format": "uuid"
@@ -18832,11 +18938,6 @@
 		"codersdk.WorkspaceBuild": {
 			"type": "object",
 			"properties": {
-				"ai_task_sidebar_app_id": {
-					"description": "Deprecated: This field has been replaced with `TaskAppID`",
-					"type": "string",
-					"format": "uuid"
-				},
 				"build_number": {
 					"type": "integer"
 				},
@@ -18852,6 +18953,7 @@
 					"format": "date-time"
 				},
 				"has_ai_task": {
+					"description": "Deprecated: This field has been deprecated in favor of Task WorkspaceID.",
 					"type": "boolean"
 				},
 				"has_external_agent": {
@@ -18911,10 +19013,6 @@
 						}
 					]
 				},
-				"task_app_id": {
-					"type": "string",
-					"format": "uuid"
-				},
 				"template_version_id": {
 					"type": "string",
 					"format": "uuid"

coderd/audit.go

@@ -509,11 +509,11 @@ func (api *API) auditLogResourceLink(ctx context.Context, alog database.GetAudit
 		if err != nil {
 			return ""
 		}
-		workspace, err := api.Database.GetWorkspaceByID(ctx, task.WorkspaceID.UUID)
+		user, err := api.Database.GetUserByID(ctx, task.OwnerID)
 		if err != nil {
 			return ""
 		}
-		return fmt.Sprintf("/tasks/%s/%s", workspace.OwnerName, task.Name)
+		return fmt.Sprintf("/tasks/%s/%s", user.Username, task.ID)
 
 	default:
 		return ""

coderd/autobuild/lifecycle_executor_test.go

@@ -1764,3 +1764,175 @@ func TestExecutorAutostartSkipsWhenNoProvisionersAvailable(t *testing.T) {
 
 	assert.Len(t, stats.Transitions, 1, "should create builds when provisioners are available")
 }
+
+func TestExecutorTaskWorkspace(t *testing.T) {
+	t.Parallel()
+
+	createTaskTemplate := func(t *testing.T, client *codersdk.Client, orgID uuid.UUID, ctx context.Context, defaultTTL time.Duration) codersdk.Template {
+		t.Helper()
+
+		taskAppID := uuid.New()
+		version := coderdtest.CreateTemplateVersion(t, client, orgID, &echo.Responses{
+			Parse: echo.ParseComplete,
+			ProvisionPlan: []*proto.Response{
+				{
+					Type: &proto.Response_Plan{
+						Plan: &proto.PlanComplete{HasAiTasks: true},
+					},
+				},
+			},
+			ProvisionApply: []*proto.Response{
+				{
+					Type: &proto.Response_Apply{
+						Apply: &proto.ApplyComplete{
+							Resources: []*proto.Resource{
+								{
+									Agents: []*proto.Agent{
+										{
+											Id:   uuid.NewString(),
+											Name: "dev",
+											Auth: &proto.Agent_Token{
+												Token: uuid.NewString(),
+											},
+											Apps: []*proto.App{
+												{
+													Id:   taskAppID.String(),
+													Slug: "task-app",
+												},
+											},
+										},
+									},
+								},
+							},
+							AiTasks: []*proto.AITask{
+								{
+									AppId: taskAppID.String(),
+								},
+							},
+						},
+					},
+				},
+			},
+		})
+		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
+		template := coderdtest.CreateTemplate(t, client, orgID, version.ID)
+
+		if defaultTTL > 0 {
+			_, err := client.UpdateTemplateMeta(ctx, template.ID, codersdk.UpdateTemplateMeta{
+				DefaultTTLMillis: defaultTTL.Milliseconds(),
+			})
+			require.NoError(t, err)
+		}
+
+		return template
+	}
+
+	createTaskWorkspace := func(t *testing.T, client *codersdk.Client, template codersdk.Template, ctx context.Context, input string) codersdk.Workspace {
+		t.Helper()
+
+		exp := codersdk.NewExperimentalClient(client)
+		task, err := exp.CreateTask(ctx, "me", codersdk.CreateTaskRequest{
+			TemplateVersionID: template.ActiveVersionID,
+			Input:             input,
+		})
+		require.NoError(t, err)
+		require.True(t, task.WorkspaceID.Valid, "task should have a workspace")
+
+		workspace, err := client.Workspace(ctx, task.WorkspaceID.UUID)
+		require.NoError(t, err)
+		coderdtest.AwaitWorkspaceBuildJobCompleted(t, client, workspace.LatestBuild.ID)
+
+		return workspace
+	}
+
+	t.Run("Autostart", func(t *testing.T) {
+		t.Parallel()
+
+		var (
+			ctx        = testutil.Context(t, testutil.WaitShort)
+			sched      = mustSchedule(t, "CRON_TZ=UTC 0 * * * *")
+			tickCh     = make(chan time.Time)
+			statsCh    = make(chan autobuild.Stats)
+			client, db = coderdtest.NewWithDatabase(t, &coderdtest.Options{
+				AutobuildTicker:          tickCh,
+				IncludeProvisionerDaemon: true,
+				AutobuildStats:           statsCh,
+			})
+			admin = coderdtest.CreateFirstUser(t, client)
+		)
+
+		// Given: A task workspace
+		template := createTaskTemplate(t, client, admin.OrganizationID, ctx, 0)
+		workspace := createTaskWorkspace(t, client, template, ctx, "test task for autostart")
+
+		// Given: The task workspace has an autostart schedule
+		err := client.UpdateWorkspaceAutostart(ctx, workspace.ID, codersdk.UpdateWorkspaceAutostartRequest{
+			Schedule: ptr.Ref(sched.String()),
+		})
+		require.NoError(t, err)
+
+		// Given: That the workspace is in a stopped state.
+		workspace = coderdtest.MustTransitionWorkspace(t, client, workspace.ID, codersdk.WorkspaceTransitionStart, codersdk.WorkspaceTransitionStop)
+
+		p, err := coderdtest.GetProvisionerForTags(db, time.Now(), workspace.OrganizationID, map[string]string{})
+		require.NoError(t, err)
+
+		// When: the autobuild executor ticks after the scheduled time
+		go func() {
+			tickTime := sched.Next(workspace.LatestBuild.CreatedAt)
+			coderdtest.UpdateProvisionerLastSeenAt(t, db, p.ID, tickTime)
+			tickCh <- tickTime
+			close(tickCh)
+		}()
+
+		// Then: We expect to see a start transition
+		stats := <-statsCh
+		require.Len(t, stats.Transitions, 1, "lifecycle executor should transition the task workspace")
+		assert.Contains(t, stats.Transitions, workspace.ID, "task workspace should be in transitions")
+		assert.Equal(t, database.WorkspaceTransitionStart, stats.Transitions[workspace.ID], "should autostart the workspace")
+		require.Empty(t, stats.Errors, "should have no errors when managing task workspaces")
+	})
+
+	t.Run("Autostop", func(t *testing.T) {
+		t.Parallel()
+
+		var (
+			ctx        = testutil.Context(t, testutil.WaitShort)
+			tickCh     = make(chan time.Time)
+			statsCh    = make(chan autobuild.Stats)
+			client, db = coderdtest.NewWithDatabase(t, &coderdtest.Options{
+				AutobuildTicker:          tickCh,
+				IncludeProvisionerDaemon: true,
+				AutobuildStats:           statsCh,
+			})
+			admin = coderdtest.CreateFirstUser(t, client)
+		)
+
+		// Given: A task workspace with an 8 hour deadline
+		template := createTaskTemplate(t, client, admin.OrganizationID, ctx, 8*time.Hour)
+		workspace := createTaskWorkspace(t, client, template, ctx, "test task for autostop")
+
+		// Given: The workspace is currently running
+		workspace = coderdtest.MustWorkspace(t, client, workspace.ID)
+		require.Equal(t, codersdk.WorkspaceTransitionStart, workspace.LatestBuild.Transition)
+		require.NotZero(t, workspace.LatestBuild.Deadline, "workspace should have a deadline for autostop")
+
+		p, err := coderdtest.GetProvisionerForTags(db, time.Now(), workspace.OrganizationID, map[string]string{})
+		require.NoError(t, err)
+
+		// When: the autobuild executor ticks after the deadline
+		go func() {
+			tickTime := workspace.LatestBuild.Deadline.Time.Add(time.Minute)
+			coderdtest.UpdateProvisionerLastSeenAt(t, db, p.ID, tickTime)
+			tickCh <- tickTime
+			close(tickCh)
+		}()
+
+		// Then: We expect to see a stop transition
+		stats := <-statsCh
+		require.Len(t, stats.Transitions, 1, "lifecycle executor should transition the task workspace")
+		assert.Contains(t, stats.Transitions, workspace.ID, "task workspace should be in transitions")
+		assert.Equal(t, database.WorkspaceTransitionStop, stats.Transitions[workspace.ID], "should autostop the workspace")
+		require.Empty(t, stats.Errors, "should have no errors when managing task workspaces")
+	})
+}

coderd/coderd.go

@@ -610,6 +610,7 @@ func New(options *Options) *API {
 		dbRolluper: options.DatabaseRolluper,
 	}
 	api.WorkspaceAppsProvider = workspaceapps.NewDBTokenProvider(
+		ctx,
 		options.Logger.Named("workspaceapps"),
 		options.AccessURL,
 		options.Authorizer,
@@ -1021,10 +1022,7 @@ func New(options *Options) *API {
 			apiRateLimiter,
 			httpmw.ReportCLITelemetry(api.Logger, options.Telemetry),
 		)
-		r.Route("/aitasks", func(r chi.Router) {
-			r.Use(apiKeyMiddleware)
-			r.Get("/prompts", api.aiTasksPrompts)
-		})
+
 		r.Route("/tasks", func(r chi.Router) {
 			r.Use(apiKeyMiddleware)
 
@@ -2002,6 +2000,7 @@ func (api *API) CreateInMemoryTaggedProvisionerDaemon(dialCtx context.Context, n
 		api.NotificationsEnqueuer,
 		&api.PrebuildsReconciler,
 		api.ProvisionerdServerMetrics,
+		api.Experiments,
 	)
 	if err != nil {
 		return nil, err

coderd/coderdtest/coderdtest.go

@@ -1604,7 +1604,7 @@ func (nopcloser) Close() error { return nil }
 // SDKError coerces err into an SDK error.
 func SDKError(t testing.TB, err error) *codersdk.Error {
 	var cerr *codersdk.Error
-	require.True(t, errors.As(err, &cerr), "should be SDK error, got %w", err)
+	require.True(t, errors.As(err, &cerr), "should be SDK error, got %s", err)
 	return cerr
 }
 

coderd/database/check_constraint.go

@@ -6,15 +6,14 @@ type CheckConstraint string
 
 // CheckConstraint enums.
 const (
-	CheckAPIKeysAllowListNotEmpty                  CheckConstraint = "api_keys_allow_list_not_empty"                    // api_keys
-	CheckOneTimePasscodeSet                        CheckConstraint = "one_time_passcode_set"                            // users
-	CheckUsersUsernameMinLength                    CheckConstraint = "users_username_min_length"                        // users
-	CheckMaxProvisionerLogsLength                  CheckConstraint = "max_provisioner_logs_length"                      // provisioner_jobs
-	CheckMaxLogsLength                             CheckConstraint = "max_logs_length"                                  // workspace_agents
-	CheckSubsystemsNotNone                         CheckConstraint = "subsystems_not_none"                              // workspace_agents
-	CheckWorkspaceBuildsAiTaskSidebarAppIDRequired CheckConstraint = "workspace_builds_ai_task_sidebar_app_id_required" // workspace_builds
-	CheckWorkspaceBuildsDeadlineBelowMaxDeadline   CheckConstraint = "workspace_builds_deadline_below_max_deadline"     // workspace_builds
-	CheckTelemetryLockEventTypeConstraint          CheckConstraint = "telemetry_lock_event_type_constraint"             // telemetry_locks
-	CheckValidationMonotonicOrder                  CheckConstraint = "validation_monotonic_order"                       // template_version_parameters
-	CheckUsageEventTypeCheck                       CheckConstraint = "usage_event_type_check"                           // usage_events
+	CheckAPIKeysAllowListNotEmpty                CheckConstraint = "api_keys_allow_list_not_empty"                // api_keys
+	CheckOneTimePasscodeSet                      CheckConstraint = "one_time_passcode_set"                        // users
+	CheckUsersUsernameMinLength                  CheckConstraint = "users_username_min_length"                    // users
+	CheckMaxProvisionerLogsLength                CheckConstraint = "max_provisioner_logs_length"                  // provisioner_jobs
+	CheckMaxLogsLength                           CheckConstraint = "max_logs_length"                              // workspace_agents
+	CheckSubsystemsNotNone                       CheckConstraint = "subsystems_not_none"                          // workspace_agents
+	CheckWorkspaceBuildsDeadlineBelowMaxDeadline CheckConstraint = "workspace_builds_deadline_below_max_deadline" // workspace_builds
+	CheckTelemetryLockEventTypeConstraint        CheckConstraint = "telemetry_lock_event_type_constraint"         // telemetry_locks
+	CheckValidationMonotonicOrder                CheckConstraint = "validation_monotonic_order"                   // template_version_parameters
+	CheckUsageEventTypeCheck                     CheckConstraint = "usage_event_type_check"                       // usage_events
 )

coderd/database/db2sdk/db2sdk.go

@@ -974,6 +974,9 @@ func AIBridgeInterception(interception database.AIBridgeInterception, initiator
 		UserPrompts: sdkUserPrompts,
 		ToolUsages:  sdkToolUsages,
 	}
+	if interception.APIKeyID.Valid {
+		intc.APIKeyID = &interception.APIKeyID.String
+	}
 	if interception.EndedAt.Valid {
 		intc.EndedAt = &interception.EndedAt.Time
 	}
@@ -1018,6 +1021,18 @@ func AIBridgeToolUsage(usage database.AIBridgeToolUsage) codersdk.AIBridgeToolUs
 	}
 }
 
+func InvalidatedPresets(invalidatedPresets []database.UpdatePresetsLastInvalidatedAtRow) []codersdk.InvalidatedPreset {
+	var presets []codersdk.InvalidatedPreset
+	for _, p := range invalidatedPresets {
+		presets = append(presets, codersdk.InvalidatedPreset{
+			TemplateName:        p.TemplateName,
+			TemplateVersionName: p.TemplateVersionName,
+			PresetName:          p.TemplateVersionPresetName,
+		})
+	}
+	return presets
+}
+
 func jsonOrEmptyMap(rawMessage pqtype.NullRawMessage) map[string]any {
 	var m map[string]any
 	if !rawMessage.Valid {

coderd/database/dbauthz/dbauthz.go

@@ -219,8 +219,8 @@ var (
 					rbac.ResourceUser.Type:             {policy.ActionRead, policy.ActionReadPersonal, policy.ActionUpdatePersonal},
 					rbac.ResourceWorkspaceDormant.Type: {policy.ActionDelete, policy.ActionRead, policy.ActionUpdate, policy.ActionWorkspaceStop},
 					rbac.ResourceWorkspace.Type:        {policy.ActionDelete, policy.ActionRead, policy.ActionUpdate, policy.ActionWorkspaceStart, policy.ActionWorkspaceStop, policy.ActionCreateAgent},
-					// Provisionerd needs to read and update tasks associated with workspaces.
-					rbac.ResourceTask.Type:   {policy.ActionRead, policy.ActionUpdate},
+					// Provisionerd needs to read, update, and delete tasks associated with workspaces.
+					rbac.ResourceTask.Type:   {policy.ActionRead, policy.ActionUpdate, policy.ActionDelete},
 					rbac.ResourceApiKey.Type: {policy.WildcardSymbol},
 					// When org scoped provisioner credentials are implemented,
 					// this can be reduced to read a specific org.
@@ -254,6 +254,7 @@ var (
 					rbac.ResourceFile.Type:                {policy.ActionRead}, // Required to read terraform files
 					rbac.ResourceNotificationMessage.Type: {policy.ActionCreate, policy.ActionRead},
 					rbac.ResourceSystem.Type:              {policy.WildcardSymbol},
+					rbac.ResourceTask.Type:                {policy.ActionRead, policy.ActionUpdate},
 					rbac.ResourceTemplate.Type:            {policy.ActionRead, policy.ActionUpdate},
 					rbac.ResourceUser.Type:                {policy.ActionRead},
 					rbac.ResourceWorkspace.Type:           {policy.ActionDelete, policy.ActionRead, policy.ActionUpdate, policy.ActionWorkspaceStart, policy.ActionWorkspaceStop},
@@ -595,19 +596,19 @@ var (
 	// See aibridged package.
 	subjectAibridged = rbac.Subject{
 		Type:         rbac.SubjectAibridged,
-		FriendlyName: "AIBridge Daemon",
+		FriendlyName: "AI Bridge Daemon",
 		ID:           uuid.Nil.String(),
 		Roles: rbac.Roles([]rbac.Role{
 			{
 				Identifier:  rbac.RoleIdentifier{Name: "aibridged"},
-				DisplayName: "AIBridge Daemon",
+				DisplayName: "AI Bridge Daemon",
 				Site: rbac.Permissions(map[string][]policy.Action{
 					rbac.ResourceUser.Type: {
 						policy.ActionRead,         // Required to validate API key owner is active.
 						policy.ActionReadPersonal, // Required to read users' external auth links. // TODO: this is too broad; reduce scope to just external_auth_links by creating separate resource.
 					},
 					rbac.ResourceApiKey.Type:               {policy.ActionRead}, // Validate API keys.
-					rbac.ResourceAibridgeInterception.Type: {policy.ActionCreate, policy.ActionRead, policy.ActionUpdate},
+					rbac.ResourceAibridgeInterception.Type: {policy.ActionCreate, policy.ActionRead, policy.ActionUpdate, policy.ActionDelete},
 				}),
 				User:    []rbac.Permission{},
 				ByOrgID: map[string]rbac.OrgPermissions{},
@@ -1640,6 +1641,15 @@ func (q *querier) DeleteCustomRole(ctx context.Context, arg database.DeleteCusto
 	return q.db.DeleteCustomRole(ctx, arg)
 }
 
+func (q *querier) DeleteExpiredAPIKeys(ctx context.Context, arg database.DeleteExpiredAPIKeysParams) (int64, error) {
+	// Requires DELETE across all API keys.
+	if err := q.authorizeContext(ctx, policy.ActionDelete, rbac.ResourceApiKey); err != nil {
+		return 0, err
+	}
+
+	return q.db.DeleteExpiredAPIKeys(ctx, arg)
+}
+
 func (q *querier) DeleteExternalAuthLink(ctx context.Context, arg database.DeleteExternalAuthLinkParams) error {
 	return fetchAndExec(q.log, q.auth, policy.ActionUpdatePersonal, func(ctx context.Context, arg database.DeleteExternalAuthLinkParams) (database.ExternalAuthLink, error) {
 		//nolint:gosimple
@@ -1722,6 +1732,13 @@ func (q *querier) DeleteOAuth2ProviderAppTokensByAppAndUserID(ctx context.Contex
 	return q.db.DeleteOAuth2ProviderAppTokensByAppAndUserID(ctx, arg)
 }
 
+func (q *querier) DeleteOldAIBridgeRecords(ctx context.Context, beforeTime time.Time) (int32, error) {
+	if err := q.authorizeContext(ctx, policy.ActionDelete, rbac.ResourceAibridgeInterception); err != nil {
+		return -1, err
+	}
+	return q.db.DeleteOldAIBridgeRecords(ctx, beforeTime)
+}
+
 func (q *querier) DeleteOldAuditLogConnectionEvents(ctx context.Context, threshold database.DeleteOldAuditLogConnectionEventsParams) error {
 	// `ResourceSystem` is deprecated, but it doesn't make sense to add
 	// `policy.ActionDelete` to `ResourceAuditLog`, since this is the one and
@@ -2648,6 +2665,13 @@ func (q *querier) GetOrganizationsByUserID(ctx context.Context, userID database.
 	return fetchWithPostFilter(q.auth, policy.ActionRead, q.db.GetOrganizationsByUserID)(ctx, userID)
 }
 
+func (q *querier) GetOrganizationsWithPrebuildStatus(ctx context.Context, arg database.GetOrganizationsWithPrebuildStatusParams) ([]database.GetOrganizationsWithPrebuildStatusRow, error) {
+	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceOrganization.All()); err != nil {
+		return nil, err
+	}
+	return q.db.GetOrganizationsWithPrebuildStatus(ctx, arg)
+}
+
 func (q *querier) GetParameterSchemasByJobID(ctx context.Context, jobID uuid.UUID) ([]database.ParameterSchema, error) {
 	version, err := q.db.GetTemplateVersionByJobID(ctx, jobID)
 	if err != nil {
@@ -2981,6 +3005,10 @@ func (q *querier) GetTaskByID(ctx context.Context, id uuid.UUID) (database.Task,
 	return fetch(q.log, q.auth, q.db.GetTaskByID)(ctx, id)
 }
 
+func (q *querier) GetTaskByOwnerIDAndName(ctx context.Context, arg database.GetTaskByOwnerIDAndNameParams) (database.Task, error) {
+	return fetch(q.log, q.auth, q.db.GetTaskByOwnerIDAndName)(ctx, arg)
+}
+
 func (q *querier) GetTaskByWorkspaceID(ctx context.Context, workspaceID uuid.UUID) (database.Task, error) {
 	return fetch(q.log, q.auth, q.db.GetTaskByWorkspaceID)(ctx, workspaceID)
 }
@@ -4933,10 +4961,10 @@ func (q *querier) UpdateOrganizationDeletedByID(ctx context.Context, arg databas
 	return deleteQ(q.log, q.auth, q.db.GetOrganizationByID, deleteF)(ctx, arg.ID)
 }
 
-func (q *querier) UpdatePrebuildProvisionerJobWithCancel(ctx context.Context, arg database.UpdatePrebuildProvisionerJobWithCancelParams) ([]uuid.UUID, error) {
+func (q *querier) UpdatePrebuildProvisionerJobWithCancel(ctx context.Context, arg database.UpdatePrebuildProvisionerJobWithCancelParams) ([]database.UpdatePrebuildProvisionerJobWithCancelRow, error) {
 	// Prebuild operation for canceling pending prebuild jobs from non-active template versions
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourcePrebuiltWorkspace); err != nil {
-		return []uuid.UUID{}, err
+		return []database.UpdatePrebuildProvisionerJobWithCancelRow{}, err
 	}
 	return q.db.UpdatePrebuildProvisionerJobWithCancel(ctx, arg)
 }
@@ -4960,6 +4988,20 @@ func (q *querier) UpdatePresetPrebuildStatus(ctx context.Context, arg database.U
 	return q.db.UpdatePresetPrebuildStatus(ctx, arg)
 }
 
+func (q *querier) UpdatePresetsLastInvalidatedAt(ctx context.Context, arg database.UpdatePresetsLastInvalidatedAtParams) ([]database.UpdatePresetsLastInvalidatedAtRow, error) {
+	// Fetch template to check authorization
+	template, err := q.db.GetTemplateByID(ctx, arg.TemplateID)
+	if err != nil {
+		return nil, err
+	}
+
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, template); err != nil {
+		return nil, err
+	}
+
+	return q.db.UpdatePresetsLastInvalidatedAt(ctx, arg)
+}
+
 func (q *querier) UpdateProvisionerDaemonLastSeenAt(ctx context.Context, arg database.UpdateProvisionerDaemonLastSeenAtParams) error {
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceProvisionerDaemon); err != nil {
 		return err

coderd/database/dbauthz/dbauthz_test.go

@@ -216,6 +216,14 @@ func (s *MethodTestSuite) TestAPIKey() {
 		dbm.EXPECT().DeleteAPIKeyByID(gomock.Any(), key.ID).Return(nil).AnyTimes()
 		check.Args(key.ID).Asserts(key, policy.ActionDelete).Returns()
 	}))
+	s.Run("DeleteExpiredAPIKeys", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		args := database.DeleteExpiredAPIKeysParams{
+			Before:     time.Date(2025, 11, 21, 0, 0, 0, 0, time.UTC),
+			LimitCount: 1000,
+		}
+		dbm.EXPECT().DeleteExpiredAPIKeys(gomock.Any(), args).Return(int64(0), nil).AnyTimes()
+		check.Args(args).Asserts(rbac.ResourceApiKey, policy.ActionDelete).Returns(int64(0))
+	}))
 	s.Run("GetAPIKeyByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		key := testutil.Fake(s.T(), faker, database.APIKey{})
 		dbm.EXPECT().GetAPIKeyByID(gomock.Any(), key.ID).Return(key, nil).AnyTimes()
@@ -646,10 +654,13 @@ func (s *MethodTestSuite) TestProvisionerJob() {
 			PresetID: uuid.NullUUID{UUID: uuid.New(), Valid: true},
 			Now:      dbtime.Now(),
 		}
-		jobIDs := []uuid.UUID{uuid.New(), uuid.New()}
+		canceledJobs := []database.UpdatePrebuildProvisionerJobWithCancelRow{
+			{ID: uuid.New(), WorkspaceID: uuid.New(), TemplateID: uuid.New(), TemplateVersionPresetID: uuid.NullUUID{UUID: uuid.New(), Valid: true}},
+			{ID: uuid.New(), WorkspaceID: uuid.New(), TemplateID: uuid.New(), TemplateVersionPresetID: uuid.NullUUID{UUID: uuid.New(), Valid: true}},
+		}
 
-		dbm.EXPECT().UpdatePrebuildProvisionerJobWithCancel(gomock.Any(), arg).Return(jobIDs, nil).AnyTimes()
-		check.Args(arg).Asserts(rbac.ResourcePrebuiltWorkspace, policy.ActionUpdate).Returns(jobIDs)
+		dbm.EXPECT().UpdatePrebuildProvisionerJobWithCancel(gomock.Any(), arg).Return(canceledJobs, nil).AnyTimes()
+		check.Args(arg).Asserts(rbac.ResourcePrebuiltWorkspace, policy.ActionUpdate).Returns(canceledJobs)
 	}))
 	s.Run("GetProvisionerJobsByIDs", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		org := testutil.Fake(s.T(), faker, database.Organization{})
@@ -1312,6 +1323,13 @@ func (s *MethodTestSuite) TestTemplate() {
 		dbm.EXPECT().UpsertTemplateUsageStats(gomock.Any()).Return(nil).AnyTimes()
 		check.Asserts(rbac.ResourceSystem, policy.ActionUpdate)
 	}))
+	s.Run("UpdatePresetsLastInvalidatedAt", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		t1 := testutil.Fake(s.T(), faker, database.Template{})
+		arg := database.UpdatePresetsLastInvalidatedAtParams{LastInvalidatedAt: sql.NullTime{Valid: true, Time: dbtime.Now()}, TemplateID: t1.ID}
+		dbm.EXPECT().GetTemplateByID(gomock.Any(), t1.ID).Return(t1, nil).AnyTimes()
+		dbm.EXPECT().UpdatePresetsLastInvalidatedAt(gomock.Any(), arg).Return([]database.UpdatePresetsLastInvalidatedAtRow{}, nil).AnyTimes()
+		check.Args(arg).Asserts(t1, policy.ActionUpdate)
+	}))
 }
 
 func (s *MethodTestSuite) TestUser() {
@@ -2158,7 +2176,7 @@ func (s *MethodTestSuite) TestWorkspace() {
 		})
 		res := testutil.Fake(s.T(), faker, database.WorkspaceResource{JobID: b.JobID})
 		agt := testutil.Fake(s.T(), faker, database.WorkspaceAgent{ResourceID: res.ID})
-		app := testutil.Fake(s.T(), faker, database.WorkspaceApp{AgentID: agt.ID})
+		_ = testutil.Fake(s.T(), faker, database.WorkspaceApp{AgentID: agt.ID})
 
 		dbm.EXPECT().GetWorkspaceByID(gomock.Any(), w.ID).Return(w, nil).AnyTimes()
 		dbm.EXPECT().GetWorkspaceBuildByID(gomock.Any(), b.ID).Return(b, nil).AnyTimes()
@@ -2167,7 +2185,6 @@ func (s *MethodTestSuite) TestWorkspace() {
 			ID:               b.ID,
 			HasAITask:        sql.NullBool{Bool: true, Valid: true},
 			HasExternalAgent: sql.NullBool{Bool: true, Valid: true},
-			SidebarAppID:     uuid.NullUUID{UUID: app.ID, Valid: true},
 			UpdatedAt:        b.UpdatedAt,
 		}).Asserts(w, policy.ActionUpdate)
 	}))
@@ -2372,6 +2389,17 @@ func (s *MethodTestSuite) TestTasks() {
 		dbm.EXPECT().GetTaskByID(gomock.Any(), task.ID).Return(task, nil).AnyTimes()
 		check.Args(task.ID).Asserts(task, policy.ActionRead).Returns(task)
 	}))
+	s.Run("GetTaskByOwnerIDAndName", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		task := testutil.Fake(s.T(), faker, database.Task{})
+		dbm.EXPECT().GetTaskByOwnerIDAndName(gomock.Any(), database.GetTaskByOwnerIDAndNameParams{
+			OwnerID: task.OwnerID,
+			Name:    task.Name,
+		}).Return(task, nil).AnyTimes()
+		check.Args(database.GetTaskByOwnerIDAndNameParams{
+			OwnerID: task.OwnerID,
+			Name:    task.Name,
+		}).Asserts(task, policy.ActionRead).Returns(task)
+	}))
 	s.Run("DeleteTask", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		task := testutil.Fake(s.T(), faker, database.Task{})
 		arg := database.DeleteTaskParams{
@@ -3756,6 +3784,14 @@ func (s *MethodTestSuite) TestPrebuilds() {
 		dbm.EXPECT().GetPrebuildMetrics(gomock.Any()).Return([]database.GetPrebuildMetricsRow{}, nil).AnyTimes()
 		check.Args().Asserts(rbac.ResourceWorkspace.All(), policy.ActionRead)
 	}))
+	s.Run("GetOrganizationsWithPrebuildStatus", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		arg := database.GetOrganizationsWithPrebuildStatusParams{
+			UserID:    uuid.New(),
+			GroupName: "test",
+		}
+		dbm.EXPECT().GetOrganizationsWithPrebuildStatus(gomock.Any(), arg).Return([]database.GetOrganizationsWithPrebuildStatusRow{}, nil).AnyTimes()
+		check.Args(arg).Asserts(rbac.ResourceOrganization.All(), policy.ActionRead)
+	}))
 	s.Run("GetPrebuildsSettings", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
 		dbm.EXPECT().GetPrebuildsSettings(gomock.Any()).Return("{}", nil).AnyTimes()
 		check.Args().Asserts()
@@ -4626,6 +4662,12 @@ func (s *MethodTestSuite) TestAIBridge() {
 		db.EXPECT().UpdateAIBridgeInterceptionEnded(gomock.Any(), params).Return(intc, nil).AnyTimes()
 		check.Args(params).Asserts(intc, policy.ActionUpdate).Returns(intc)
 	}))
+
+	s.Run("DeleteOldAIBridgeRecords", s.Mocked(func(db *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		t := dbtime.Now()
+		db.EXPECT().DeleteOldAIBridgeRecords(gomock.Any(), t).Return(int32(0), nil).AnyTimes()
+		check.Args(t).Asserts(rbac.ResourceAibridgeInterception, policy.ActionDelete)
+	}))
 }
 
 func (s *MethodTestSuite) TestTelemetry() {

coderd/database/dbfake/dbfake.go

@@ -41,6 +41,7 @@ type WorkspaceResponse struct {
 	Build      database.WorkspaceBuild
 	AgentToken string
 	TemplateVersionResponse
+	Task database.Task
 }
 
 // WorkspaceBuildBuilder generates workspace builds and associated
@@ -57,6 +58,7 @@ type WorkspaceBuildBuilder struct {
 	agentToken string
 	jobStatus  database.ProvisionerJobStatus
 	taskAppID  uuid.UUID
+	taskSeed   database.TaskTable
 }
 
 // WorkspaceBuild generates a workspace build for the provided workspace.
@@ -115,25 +117,28 @@ func (b WorkspaceBuildBuilder) WithAgent(mutations ...func([]*sdkproto.Agent) []
 	return b
 }
 
-func (b WorkspaceBuildBuilder) WithTask(seed *sdkproto.App) WorkspaceBuildBuilder {
-	if seed == nil {
-		seed = &sdkproto.App{}
+func (b WorkspaceBuildBuilder) WithTask(taskSeed database.TaskTable, appSeed *sdkproto.App) WorkspaceBuildBuilder {
+	//nolint:revive // returns modified struct
+	b.taskSeed = taskSeed
+
+	if appSeed == nil {
+		appSeed = &sdkproto.App{}
 	}
 
 	var err error
 	//nolint: revive // returns modified struct
-	b.taskAppID, err = uuid.Parse(takeFirst(seed.Id, uuid.NewString()))
+	b.taskAppID, err = uuid.Parse(takeFirst(appSeed.Id, uuid.NewString()))
 	require.NoError(b.t, err)
 
 	return b.Params(database.WorkspaceBuildParameter{
 		Name:  codersdk.AITaskPromptParameterName,
-		Value: "list me",
+		Value: b.taskSeed.Prompt,
 	}).WithAgent(func(a []*sdkproto.Agent) []*sdkproto.Agent {
 		a[0].Apps = []*sdkproto.App{
 			{
 				Id:   b.taskAppID.String(),
-				Slug: takeFirst(seed.Slug, "task-app"),
-				Url:  takeFirst(seed.Url, ""),
+				Slug: takeFirst(appSeed.Slug, "task-app"),
+				Url:  takeFirst(appSeed.Url, ""),
 			},
 		}
 		return a
@@ -184,7 +189,6 @@ func (b WorkspaceBuildBuilder) doInTX() WorkspaceResponse {
 			Bool:  true,
 			Valid: true,
 		}
-		b.seed.AITaskSidebarAppID = uuid.NullUUID{UUID: b.taskAppID, Valid: true}
 	}
 
 	resp := WorkspaceResponse{
@@ -225,6 +229,37 @@ func (b WorkspaceBuildBuilder) doInTX() WorkspaceResponse {
 	b.seed.WorkspaceID = b.ws.ID
 	b.seed.InitiatorID = takeFirst(b.seed.InitiatorID, b.ws.OwnerID)
 
+	// If a task was requested, ensure it exists and is associated with this
+	// workspace.
+	if b.taskAppID != uuid.Nil {
+		b.logger.Debug(context.Background(), "creating or updating task", "task_id", b.taskSeed.ID)
+		b.taskSeed.OrganizationID = takeFirst(b.taskSeed.OrganizationID, b.ws.OrganizationID)
+		b.taskSeed.OwnerID = takeFirst(b.taskSeed.OwnerID, b.ws.OwnerID)
+		b.taskSeed.Name = takeFirst(b.taskSeed.Name, b.ws.Name)
+		b.taskSeed.WorkspaceID = uuid.NullUUID{UUID: takeFirst(b.taskSeed.WorkspaceID.UUID, b.ws.ID), Valid: true}
+		b.taskSeed.TemplateVersionID = takeFirst(b.taskSeed.TemplateVersionID, b.seed.TemplateVersionID)
+
+		// Try to fetch existing task and update its workspace ID.
+		if task, err := b.db.GetTaskByID(ownerCtx, b.taskSeed.ID); err == nil {
+			if !task.WorkspaceID.Valid {
+				b.logger.Info(context.Background(), "updating task workspace id", "task_id", b.taskSeed.ID, "workspace_id", b.ws.ID)
+				_, err = b.db.UpdateTaskWorkspaceID(ownerCtx, database.UpdateTaskWorkspaceIDParams{
+					ID:          b.taskSeed.ID,
+					WorkspaceID: uuid.NullUUID{UUID: b.ws.ID, Valid: true},
+				})
+				require.NoError(b.t, err, "update task workspace id")
+			} else if task.WorkspaceID.UUID != b.ws.ID {
+				require.Fail(b.t, "task already has a workspace id, mismatch", task.WorkspaceID.UUID, b.ws.ID)
+			}
+		} else if errors.Is(err, sql.ErrNoRows) {
+			task := dbgen.Task(b.t, b.db, b.taskSeed)
+			b.taskSeed.ID = task.ID
+			b.logger.Info(context.Background(), "created new task", "task_id", b.taskSeed.ID)
+		} else {
+			require.NoError(b.t, err, "get task by id")
+		}
+	}
+
 	// Create a provisioner job for the build!
 	payload, err := json.Marshal(provisionerdserver.WorkspaceProvisionJob{
 		WorkspaceBuildID: b.seed.ID,
@@ -326,17 +361,30 @@ func (b WorkspaceBuildBuilder) doInTX() WorkspaceResponse {
 			require.Fail(b.t, "task app not configured but workspace is a task workspace")
 		}
 
-		app := mustWorkspaceAppByWorkspaceAndBuildAndAppID(ownerCtx, b.t, b.db, resp.Workspace.ID, resp.Build.BuildNumber, b.taskAppID)
+		workspaceAgentID := uuid.NullUUID{}
+		workspaceAppID := uuid.NullUUID{}
+		// Workspace agent and app are only properly set upon job completion
+		if b.jobStatus != database.ProvisionerJobStatusPending && b.jobStatus != database.ProvisionerJobStatusRunning {
+			app := mustWorkspaceAppByWorkspaceAndBuildAndAppID(ownerCtx, b.t, b.db, resp.Workspace.ID, resp.Build.BuildNumber, b.taskAppID)
+			workspaceAgentID = uuid.NullUUID{UUID: app.AgentID, Valid: true}
+			workspaceAppID = uuid.NullUUID{UUID: app.ID, Valid: true}
+		}
+
 		_, err = b.db.UpsertTaskWorkspaceApp(ownerCtx, database.UpsertTaskWorkspaceAppParams{
 			TaskID:               task.ID,
 			WorkspaceBuildNumber: resp.Build.BuildNumber,
-			WorkspaceAgentID:     uuid.NullUUID{UUID: app.AgentID, Valid: true},
-			WorkspaceAppID:       uuid.NullUUID{UUID: app.ID, Valid: true},
+			WorkspaceAgentID:     workspaceAgentID,
+			WorkspaceAppID:       workspaceAppID,
 		})
 		require.NoError(b.t, err, "upsert task workspace app")
 		b.logger.Debug(context.Background(), "linked task to workspace build",
 			slog.F("task_id", task.ID),
 			slog.F("build_number", resp.Build.BuildNumber))
+
+		// Update task after linking.
+		task, err = b.db.GetTaskByID(ownerCtx, task.ID)
+		require.NoError(b.t, err, "get task by id")
+		resp.Task = task
 	}
 
 	for i := range b.params {
@@ -565,6 +613,7 @@ func (t TemplateVersionBuilder) Do() TemplateVersionResponse {
 			IsDefault:           false,
 			Description:         preset.Description,
 			Icon:                preset.Icon,
+			LastInvalidatedAt:   preset.LastInvalidatedAt,
 		})
 		t.logger.Debug(context.Background(), "added preset",
 			slog.F("preset_id", prst.ID),
@@ -582,6 +631,7 @@ func (t TemplateVersionBuilder) Do() TemplateVersionResponse {
 	}
 
 	payload, err := json.Marshal(provisionerdserver.TemplateVersionImportJob{
+		TemplateID:        t.seed.TemplateID,
 		TemplateVersionID: t.seed.ID,
 	})
 	require.NoError(t.t, err)

coderd/database/dbgen/dbgen.go

@@ -175,6 +175,13 @@ func APIKey(t testing.TB, db database.Store, seed database.APIKey, munge ...func
 		}
 	}
 
+	// It does not make sense for the created_at to be after the expires_at.
+	// So if expires is set, change the default created_at to be 24 hours before.
+	var createdAt time.Time
+	if !seed.ExpiresAt.IsZero() && seed.CreatedAt.IsZero() {
+		createdAt = seed.ExpiresAt.Add(-24 * time.Hour)
+	}
+
 	params := database.InsertAPIKeyParams{
 		ID: takeFirst(seed.ID, id),
 		// 0 defaults to 86400 at the db layer
@@ -184,7 +191,7 @@ func APIKey(t testing.TB, db database.Store, seed database.APIKey, munge ...func
 		UserID:          takeFirst(seed.UserID, uuid.New()),
 		LastUsed:        takeFirst(seed.LastUsed, dbtime.Now()),
 		ExpiresAt:       takeFirst(seed.ExpiresAt, dbtime.Now().Add(time.Hour)),
-		CreatedAt:       takeFirst(seed.CreatedAt, dbtime.Now()),
+		CreatedAt:       takeFirst(seed.CreatedAt, createdAt, dbtime.Now()),
 		UpdatedAt:       takeFirst(seed.UpdatedAt, dbtime.Now()),
 		LoginType:       takeFirst(seed.LoginType, database.LoginTypePassword),
 		Scopes:          takeFirstSlice([]database.APIKeyScope(seed.Scopes), []database.APIKeyScope{database.ApiKeyScopeCoderAll}),
@@ -451,7 +458,6 @@ func WorkspaceBuild(t testing.TB, db database.Store, orig database.WorkspaceBuil
 	buildID := takeFirst(orig.ID, uuid.New())
 	jobID := takeFirst(orig.JobID, uuid.New())
 	hasAITask := takeFirst(orig.HasAITask, sql.NullBool{})
-	sidebarAppID := takeFirst(orig.AITaskSidebarAppID, uuid.NullUUID{})
 	hasExternalAgent := takeFirst(orig.HasExternalAgent, sql.NullBool{})
 	var build database.WorkspaceBuild
 	err := db.InTx(func(db database.Store) error {
@@ -491,7 +497,6 @@ func WorkspaceBuild(t testing.TB, db database.Store, orig database.WorkspaceBuil
 				ID:               buildID,
 				HasAITask:        hasAITask,
 				HasExternalAgent: hasExternalAgent,
-				SidebarAppID:     sidebarAppID,
 				UpdatedAt:        dbtime.Now(),
 			}))
 		}
@@ -1430,6 +1435,7 @@ func Preset(t testing.TB, db database.Store, seed database.InsertPresetParams) d
 		IsDefault:           seed.IsDefault,
 		Description:         seed.Description,
 		Icon:                seed.Icon,
+		LastInvalidatedAt:   seed.LastInvalidatedAt,
 	})
 	require.NoError(t, err, "insert preset")
 	return preset
@@ -1498,6 +1504,7 @@ func ClaimPrebuild(
 func AIBridgeInterception(t testing.TB, db database.Store, seed database.InsertAIBridgeInterceptionParams, endedAt *time.Time) database.AIBridgeInterception {
 	interception, err := db.InsertAIBridgeInterception(genCtx, database.InsertAIBridgeInterceptionParams{
 		ID:          takeFirst(seed.ID, uuid.New()),
+		APIKeyID:    seed.APIKeyID,
 		InitiatorID: takeFirst(seed.InitiatorID, uuid.New()),
 		Provider:    takeFirst(seed.Provider, "provider"),
 		Model:       takeFirst(seed.Model, "model"),
@@ -1576,6 +1583,7 @@ func Task(t testing.TB, db database.Store, orig database.TaskTable) database.Tas
 	}
 
 	task, err := db.InsertTask(genCtx, database.InsertTaskParams{
+		ID:                 takeFirst(orig.ID, uuid.New()),
 		OrganizationID:     orig.OrganizationID,
 		OwnerID:            orig.OwnerID,
 		Name:               takeFirst(orig.Name, taskname.GenerateFallback()),

coderd/database/dbmetrics/querymetrics.go

@@ -312,6 +312,13 @@ func (m queryMetricsStore) DeleteCustomRole(ctx context.Context, arg database.De
 	return r0
 }
 
+func (m queryMetricsStore) DeleteExpiredAPIKeys(ctx context.Context, arg database.DeleteExpiredAPIKeysParams) (int64, error) {
+	start := time.Now()
+	r0, r1 := m.s.DeleteExpiredAPIKeys(ctx, arg)
+	m.queryLatencies.WithLabelValues("DeleteExpiredAPIKeys").Observe(time.Since(start).Seconds())
+	return r0, r1
+}
+
 func (m queryMetricsStore) DeleteExternalAuthLink(ctx context.Context, arg database.DeleteExternalAuthLinkParams) error {
 	start := time.Now()
 	r0 := m.s.DeleteExternalAuthLink(ctx, arg)
@@ -389,6 +396,13 @@ func (m queryMetricsStore) DeleteOAuth2ProviderAppTokensByAppAndUserID(ctx conte
 	return r0
 }
 
+func (m queryMetricsStore) DeleteOldAIBridgeRecords(ctx context.Context, beforeTime time.Time) (int32, error) {
+	start := time.Now()
+	r0, r1 := m.s.DeleteOldAIBridgeRecords(ctx, beforeTime)
+	m.queryLatencies.WithLabelValues("DeleteOldAIBridgeRecords").Observe(time.Since(start).Seconds())
+	return r0, r1
+}
+
 func (m queryMetricsStore) DeleteOldAuditLogConnectionEvents(ctx context.Context, threshold database.DeleteOldAuditLogConnectionEventsParams) error {
 	start := time.Now()
 	r0 := m.s.DeleteOldAuditLogConnectionEvents(ctx, threshold)
@@ -1243,6 +1257,13 @@ func (m queryMetricsStore) GetOrganizationsByUserID(ctx context.Context, userID
 	return organizations, err
 }
 
+func (m queryMetricsStore) GetOrganizationsWithPrebuildStatus(ctx context.Context, arg database.GetOrganizationsWithPrebuildStatusParams) ([]database.GetOrganizationsWithPrebuildStatusRow, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetOrganizationsWithPrebuildStatus(ctx, arg)
+	m.queryLatencies.WithLabelValues("GetOrganizationsWithPrebuildStatus").Observe(time.Since(start).Seconds())
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetParameterSchemasByJobID(ctx context.Context, jobID uuid.UUID) ([]database.ParameterSchema, error) {
 	start := time.Now()
 	schemas, err := m.s.GetParameterSchemasByJobID(ctx, jobID)
@@ -1523,6 +1544,13 @@ func (m queryMetricsStore) GetTaskByID(ctx context.Context, id uuid.UUID) (datab
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetTaskByOwnerIDAndName(ctx context.Context, arg database.GetTaskByOwnerIDAndNameParams) (database.Task, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetTaskByOwnerIDAndName(ctx, arg)
+	m.queryLatencies.WithLabelValues("GetTaskByOwnerIDAndName").Observe(time.Since(start).Seconds())
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetTaskByWorkspaceID(ctx context.Context, workspaceID uuid.UUID) (database.Task, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetTaskByWorkspaceID(ctx, workspaceID)
@@ -3042,7 +3070,7 @@ func (m queryMetricsStore) UpdateOrganizationDeletedByID(ctx context.Context, ar
 	return r0
 }
 
-func (m queryMetricsStore) UpdatePrebuildProvisionerJobWithCancel(ctx context.Context, arg database.UpdatePrebuildProvisionerJobWithCancelParams) ([]uuid.UUID, error) {
+func (m queryMetricsStore) UpdatePrebuildProvisionerJobWithCancel(ctx context.Context, arg database.UpdatePrebuildProvisionerJobWithCancelParams) ([]database.UpdatePrebuildProvisionerJobWithCancelRow, error) {
 	start := time.Now()
 	r0, r1 := m.s.UpdatePrebuildProvisionerJobWithCancel(ctx, arg)
 	m.queryLatencies.WithLabelValues("UpdatePrebuildProvisionerJobWithCancel").Observe(time.Since(start).Seconds())
@@ -3056,6 +3084,13 @@ func (m queryMetricsStore) UpdatePresetPrebuildStatus(ctx context.Context, arg d
 	return r0
 }
 
+func (m queryMetricsStore) UpdatePresetsLastInvalidatedAt(ctx context.Context, arg database.UpdatePresetsLastInvalidatedAtParams) ([]database.UpdatePresetsLastInvalidatedAtRow, error) {
+	start := time.Now()
+	r0, r1 := m.s.UpdatePresetsLastInvalidatedAt(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpdatePresetsLastInvalidatedAt").Observe(time.Since(start).Seconds())
+	return r0, r1
+}
+
 func (m queryMetricsStore) UpdateProvisionerDaemonLastSeenAt(ctx context.Context, arg database.UpdateProvisionerDaemonLastSeenAtParams) error {
 	start := time.Now()
 	r0 := m.s.UpdateProvisionerDaemonLastSeenAt(ctx, arg)

coderd/database/dbmock/dbmock.go

@@ -554,6 +554,21 @@ func (mr *MockStoreMockRecorder) DeleteCustomRole(ctx, arg any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteCustomRole", reflect.TypeOf((*MockStore)(nil).DeleteCustomRole), ctx, arg)
 }
 
+// DeleteExpiredAPIKeys mocks base method.
+func (m *MockStore) DeleteExpiredAPIKeys(ctx context.Context, arg database.DeleteExpiredAPIKeysParams) (int64, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "DeleteExpiredAPIKeys", ctx, arg)
+	ret0, _ := ret[0].(int64)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// DeleteExpiredAPIKeys indicates an expected call of DeleteExpiredAPIKeys.
+func (mr *MockStoreMockRecorder) DeleteExpiredAPIKeys(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteExpiredAPIKeys", reflect.TypeOf((*MockStore)(nil).DeleteExpiredAPIKeys), ctx, arg)
+}
+
 // DeleteExternalAuthLink mocks base method.
 func (m *MockStore) DeleteExternalAuthLink(ctx context.Context, arg database.DeleteExternalAuthLinkParams) error {
 	m.ctrl.T.Helper()
@@ -709,6 +724,21 @@ func (mr *MockStoreMockRecorder) DeleteOAuth2ProviderAppTokensByAppAndUserID(ctx
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteOAuth2ProviderAppTokensByAppAndUserID", reflect.TypeOf((*MockStore)(nil).DeleteOAuth2ProviderAppTokensByAppAndUserID), ctx, arg)
 }
 
+// DeleteOldAIBridgeRecords mocks base method.
+func (m *MockStore) DeleteOldAIBridgeRecords(ctx context.Context, beforeTime time.Time) (int32, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "DeleteOldAIBridgeRecords", ctx, beforeTime)
+	ret0, _ := ret[0].(int32)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// DeleteOldAIBridgeRecords indicates an expected call of DeleteOldAIBridgeRecords.
+func (mr *MockStoreMockRecorder) DeleteOldAIBridgeRecords(ctx, beforeTime any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteOldAIBridgeRecords", reflect.TypeOf((*MockStore)(nil).DeleteOldAIBridgeRecords), ctx, beforeTime)
+}
+
 // DeleteOldAuditLogConnectionEvents mocks base method.
 func (m *MockStore) DeleteOldAuditLogConnectionEvents(ctx context.Context, arg database.DeleteOldAuditLogConnectionEventsParams) error {
 	m.ctrl.T.Helper()
@@ -2622,6 +2652,21 @@ func (mr *MockStoreMockRecorder) GetOrganizationsByUserID(ctx, arg any) *gomock.
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetOrganizationsByUserID", reflect.TypeOf((*MockStore)(nil).GetOrganizationsByUserID), ctx, arg)
 }
 
+// GetOrganizationsWithPrebuildStatus mocks base method.
+func (m *MockStore) GetOrganizationsWithPrebuildStatus(ctx context.Context, arg database.GetOrganizationsWithPrebuildStatusParams) ([]database.GetOrganizationsWithPrebuildStatusRow, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetOrganizationsWithPrebuildStatus", ctx, arg)
+	ret0, _ := ret[0].([]database.GetOrganizationsWithPrebuildStatusRow)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetOrganizationsWithPrebuildStatus indicates an expected call of GetOrganizationsWithPrebuildStatus.
+func (mr *MockStoreMockRecorder) GetOrganizationsWithPrebuildStatus(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetOrganizationsWithPrebuildStatus", reflect.TypeOf((*MockStore)(nil).GetOrganizationsWithPrebuildStatus), ctx, arg)
+}
+
 // GetParameterSchemasByJobID mocks base method.
 func (m *MockStore) GetParameterSchemasByJobID(ctx context.Context, jobID uuid.UUID) ([]database.ParameterSchema, error) {
 	m.ctrl.T.Helper()
@@ -3222,6 +3267,21 @@ func (mr *MockStoreMockRecorder) GetTaskByID(ctx, id any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetTaskByID", reflect.TypeOf((*MockStore)(nil).GetTaskByID), ctx, id)
 }
 
+// GetTaskByOwnerIDAndName mocks base method.
+func (m *MockStore) GetTaskByOwnerIDAndName(ctx context.Context, arg database.GetTaskByOwnerIDAndNameParams) (database.Task, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetTaskByOwnerIDAndName", ctx, arg)
+	ret0, _ := ret[0].(database.Task)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetTaskByOwnerIDAndName indicates an expected call of GetTaskByOwnerIDAndName.
+func (mr *MockStoreMockRecorder) GetTaskByOwnerIDAndName(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetTaskByOwnerIDAndName", reflect.TypeOf((*MockStore)(nil).GetTaskByOwnerIDAndName), ctx, arg)
+}
+
 // GetTaskByWorkspaceID mocks base method.
 func (m *MockStore) GetTaskByWorkspaceID(ctx context.Context, workspaceID uuid.UUID) (database.Task, error) {
 	m.ctrl.T.Helper()
@@ -6540,10 +6600,10 @@ func (mr *MockStoreMockRecorder) UpdateOrganizationDeletedByID(ctx, arg any) *go
 }
 
 // UpdatePrebuildProvisionerJobWithCancel mocks base method.
-func (m *MockStore) UpdatePrebuildProvisionerJobWithCancel(ctx context.Context, arg database.UpdatePrebuildProvisionerJobWithCancelParams) ([]uuid.UUID, error) {
+func (m *MockStore) UpdatePrebuildProvisionerJobWithCancel(ctx context.Context, arg database.UpdatePrebuildProvisionerJobWithCancelParams) ([]database.UpdatePrebuildProvisionerJobWithCancelRow, error) {
 	m.ctrl.T.Helper()
 	ret := m.ctrl.Call(m, "UpdatePrebuildProvisionerJobWithCancel", ctx, arg)
-	ret0, _ := ret[0].([]uuid.UUID)
+	ret0, _ := ret[0].([]database.UpdatePrebuildProvisionerJobWithCancelRow)
 	ret1, _ := ret[1].(error)
 	return ret0, ret1
 }
@@ -6568,6 +6628,21 @@ func (mr *MockStoreMockRecorder) UpdatePresetPrebuildStatus(ctx, arg any) *gomoc
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdatePresetPrebuildStatus", reflect.TypeOf((*MockStore)(nil).UpdatePresetPrebuildStatus), ctx, arg)
 }
 
+// UpdatePresetsLastInvalidatedAt mocks base method.
+func (m *MockStore) UpdatePresetsLastInvalidatedAt(ctx context.Context, arg database.UpdatePresetsLastInvalidatedAtParams) ([]database.UpdatePresetsLastInvalidatedAtRow, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "UpdatePresetsLastInvalidatedAt", ctx, arg)
+	ret0, _ := ret[0].([]database.UpdatePresetsLastInvalidatedAtRow)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// UpdatePresetsLastInvalidatedAt indicates an expected call of UpdatePresetsLastInvalidatedAt.
+func (mr *MockStoreMockRecorder) UpdatePresetsLastInvalidatedAt(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdatePresetsLastInvalidatedAt", reflect.TypeOf((*MockStore)(nil).UpdatePresetsLastInvalidatedAt), ctx, arg)
+}
+
 // UpdateProvisionerDaemonLastSeenAt mocks base method.
 func (m *MockStore) UpdateProvisionerDaemonLastSeenAt(ctx context.Context, arg database.UpdateProvisionerDaemonLastSeenAtParams) error {
 	m.ctrl.T.Helper()

coderd/database/dbpurge/dbpurge.go

@@ -13,6 +13,7 @@ import (
 	"github.com/coder/coder/v2/coderd/database/dbauthz"
 	"github.com/coder/coder/v2/coderd/database/dbtime"
 	"github.com/coder/coder/v2/coderd/pproflabel"
+	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/quartz"
 )
 
@@ -36,7 +37,7 @@ const (
 // 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, clk quartz.Clock) io.Closer {
+func New(ctx context.Context, logger slog.Logger, db database.Store, vals *codersdk.DeploymentValues, clk quartz.Clock) io.Closer {
 	closed := make(chan struct{})
 
 	ctx, cancelFunc := context.WithCancel(ctx)
@@ -77,6 +78,19 @@ func New(ctx context.Context, logger slog.Logger, db database.Store, clk quartz.
 			if err := tx.ExpirePrebuildsAPIKeys(ctx, dbtime.Time(start)); err != nil {
 				return xerrors.Errorf("failed to expire prebuilds user api keys: %w", err)
 			}
+			expiredAPIKeys, err := tx.DeleteExpiredAPIKeys(ctx, database.DeleteExpiredAPIKeysParams{
+				// Leave expired keys for a week to allow the backend to know the difference
+				// between a 404 and an expired key. This purge code is just to bound the size of
+				// the table to something more reasonable.
+				Before: dbtime.Time(start.Add(time.Hour * 24 * 7 * -1)),
+				// There could be a lot of expired keys here, so set a limit to prevent this
+				// taking too long.
+				// This runs every 10 minutes, so it deletes ~1.5m keys per day at most.
+				LimitCount: 10000,
+			})
+			if err != nil {
+				return xerrors.Errorf("failed to delete expired api keys: %w", err)
+			}
 			deleteOldTelemetryLocksBefore := start.Add(-maxTelemetryHeartbeatAge)
 			if err := tx.DeleteOldTelemetryLocks(ctx, deleteOldTelemetryLocksBefore); err != nil {
 				return xerrors.Errorf("failed to delete old telemetry locks: %w", err)
@@ -90,7 +104,18 @@ func New(ctx context.Context, logger slog.Logger, db database.Store, clk quartz.
 				return xerrors.Errorf("failed to delete old audit log connection events: %w", err)
 			}
 
-			logger.Debug(ctx, "purged old database entries", slog.F("duration", clk.Since(start)))
+			deleteAIBridgeRecordsBefore := start.Add(-vals.AI.BridgeConfig.Retention.Value())
+			// nolint:gocritic // Needs to run as aibridge context.
+			purgedAIBridgeRecords, err := tx.DeleteOldAIBridgeRecords(dbauthz.AsAIBridged(ctx), deleteAIBridgeRecordsBefore)
+			if err != nil {
+				return xerrors.Errorf("failed to delete old aibridge records: %w", err)
+			}
+
+			logger.Debug(ctx, "purged old database entries",
+				slog.F("expired_api_keys", expiredAPIKeys),
+				slog.F("aibridge_records", purgedAIBridgeRecords),
+				slog.F("duration", clk.Since(start)),
+			)
 
 			return nil
 		}, database.DefaultTXOptions().WithID("db_purge")); err != nil {

coderd/database/dbpurge/dbpurge_test.go

@@ -33,6 +33,7 @@ import (
 	"github.com/coder/coder/v2/provisionersdk"
 	"github.com/coder/coder/v2/testutil"
 	"github.com/coder/quartz"
+	"github.com/coder/serpent"
 )
 
 func TestMain(m *testing.M) {
@@ -51,7 +52,7 @@ func TestPurge(t *testing.T) {
 	done := awaitDoTick(ctx, t, clk)
 	mDB := dbmock.NewMockStore(gomock.NewController(t))
 	mDB.EXPECT().InTx(gomock.Any(), database.DefaultTXOptions().WithID("db_purge")).Return(nil).Times(2)
-	purger := dbpurge.New(context.Background(), testutil.Logger(t), mDB, clk)
+	purger := dbpurge.New(context.Background(), testutil.Logger(t), mDB, &codersdk.DeploymentValues{}, clk)
 	<-done // wait for doTick() to run.
 	require.NoError(t, purger.Close())
 }
@@ -129,7 +130,7 @@ func TestDeleteOldWorkspaceAgentStats(t *testing.T) {
 	})
 
 	// when
-	closer := dbpurge.New(ctx, logger, db, clk)
+	closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk)
 	defer closer.Close()
 
 	// then
@@ -154,7 +155,7 @@ func TestDeleteOldWorkspaceAgentStats(t *testing.T) {
 
 	// Start a new purger to immediately trigger delete after rollup.
 	_ = closer.Close()
-	closer = dbpurge.New(ctx, logger, db, clk)
+	closer = dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk)
 	defer closer.Close()
 
 	// then
@@ -245,7 +246,7 @@ func TestDeleteOldWorkspaceAgentLogs(t *testing.T) {
 	// After dbpurge completes, the ticker is reset. Trap this call.
 
 	done := awaitDoTick(ctx, t, clk)
-	closer := dbpurge.New(ctx, logger, db, clk)
+	closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk)
 	defer closer.Close()
 	<-done // doTick() has now run.
 
@@ -466,7 +467,7 @@ func TestDeleteOldProvisionerDaemons(t *testing.T) {
 	require.NoError(t, err)
 
 	// when
-	closer := dbpurge.New(ctx, logger, db, clk)
+	closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk)
 	defer closer.Close()
 
 	// then
@@ -570,7 +571,7 @@ func TestDeleteOldAuditLogConnectionEvents(t *testing.T) {
 
 	// Run the purge
 	done := awaitDoTick(ctx, t, clk)
-	closer := dbpurge.New(ctx, logger, db, clk)
+	closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk)
 	defer closer.Close()
 	// Wait for tick
 	testutil.TryReceive(ctx, t, done)
@@ -733,7 +734,7 @@ func TestDeleteOldTelemetryHeartbeats(t *testing.T) {
 	require.NoError(t, err)
 
 	done := awaitDoTick(ctx, t, clk)
-	closer := dbpurge.New(ctx, logger, db, clk)
+	closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{}, clk)
 	defer closer.Close()
 	<-done // doTick() has now run.
 
@@ -757,3 +758,172 @@ func TestDeleteOldTelemetryHeartbeats(t *testing.T) {
 		return totalCount == 2 && oldCount == 0
 	}, testutil.WaitShort, testutil.IntervalFast, "it should delete old telemetry heartbeats")
 }
+
+func TestDeleteOldAIBridgeRecords(t *testing.T) {
+	t.Parallel()
+
+	ctx := testutil.Context(t, testutil.WaitShort)
+
+	clk := quartz.NewMock(t)
+	now := time.Date(2025, 1, 15, 7, 30, 0, 0, time.UTC)
+	retentionPeriod := 30 * 24 * time.Hour                                // 30 days
+	afterThreshold := now.Add(-retentionPeriod).Add(-24 * time.Hour)      // 31 days ago (older than threshold)
+	beforeThreshold := now.Add(-15 * 24 * time.Hour)                      // 15 days ago (newer than threshold)
+	closeBeforeThreshold := now.Add(-retentionPeriod).Add(24 * time.Hour) // 29 days ago
+	clk.Set(now).MustWait(ctx)
+
+	db, _ := dbtestutil.NewDB(t, dbtestutil.WithDumpOnFailure())
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+	user := dbgen.User(t, db, database.User{})
+
+	// Create old AI Bridge interception (should be deleted)
+	oldInterception := dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+		ID:          uuid.New(),
+		APIKeyID:    sql.NullString{},
+		InitiatorID: user.ID,
+		Provider:    "anthropic",
+		Model:       "claude-3-5-sonnet",
+		StartedAt:   afterThreshold,
+	}, &afterThreshold)
+
+	// Create old interception with related records (should all be deleted)
+	oldInterceptionWithRelated := dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+		ID:          uuid.New(),
+		APIKeyID:    sql.NullString{},
+		InitiatorID: user.ID,
+		Provider:    "openai",
+		Model:       "gpt-4",
+		StartedAt:   afterThreshold,
+	}, &afterThreshold)
+
+	_ = dbgen.AIBridgeTokenUsage(t, db, database.InsertAIBridgeTokenUsageParams{
+		ID:                 uuid.New(),
+		InterceptionID:     oldInterceptionWithRelated.ID,
+		ProviderResponseID: "resp-1",
+		InputTokens:        100,
+		OutputTokens:       50,
+		CreatedAt:          afterThreshold,
+	})
+
+	_ = dbgen.AIBridgeUserPrompt(t, db, database.InsertAIBridgeUserPromptParams{
+		ID:                 uuid.New(),
+		InterceptionID:     oldInterceptionWithRelated.ID,
+		ProviderResponseID: "resp-1",
+		Prompt:             "test prompt",
+		CreatedAt:          afterThreshold,
+	})
+
+	_ = dbgen.AIBridgeToolUsage(t, db, database.InsertAIBridgeToolUsageParams{
+		ID:                 uuid.New(),
+		InterceptionID:     oldInterceptionWithRelated.ID,
+		ProviderResponseID: "resp-1",
+		Tool:               "test-tool",
+		ServerUrl:          sql.NullString{String: "http://test", Valid: true},
+		Input:              "{}",
+		Injected:           true,
+		CreatedAt:          afterThreshold,
+	})
+
+	// Create recent AI Bridge interception (should be kept)
+	recentInterception := dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+		ID:          uuid.New(),
+		APIKeyID:    sql.NullString{},
+		InitiatorID: user.ID,
+		Provider:    "anthropic",
+		Model:       "claude-3-5-sonnet",
+		StartedAt:   beforeThreshold,
+	}, &beforeThreshold)
+
+	// Create interception close to threshold (should be kept)
+	nearThresholdInterception := dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+		ID:          uuid.New(),
+		APIKeyID:    sql.NullString{},
+		InitiatorID: user.ID,
+		Provider:    "anthropic",
+		Model:       "claude-3-5-sonnet",
+		StartedAt:   closeBeforeThreshold,
+	}, &closeBeforeThreshold)
+
+	_ = dbgen.AIBridgeTokenUsage(t, db, database.InsertAIBridgeTokenUsageParams{
+		ID:                 uuid.New(),
+		InterceptionID:     nearThresholdInterception.ID,
+		ProviderResponseID: "resp-1",
+		InputTokens:        100,
+		OutputTokens:       50,
+		CreatedAt:          closeBeforeThreshold,
+	})
+
+	_ = dbgen.AIBridgeUserPrompt(t, db, database.InsertAIBridgeUserPromptParams{
+		ID:                 uuid.New(),
+		InterceptionID:     nearThresholdInterception.ID,
+		ProviderResponseID: "resp-1",
+		Prompt:             "test prompt",
+		CreatedAt:          closeBeforeThreshold,
+	})
+
+	_ = dbgen.AIBridgeToolUsage(t, db, database.InsertAIBridgeToolUsageParams{
+		ID:                 uuid.New(),
+		InterceptionID:     nearThresholdInterception.ID,
+		ProviderResponseID: "resp-1",
+		Tool:               "test-tool",
+		ServerUrl:          sql.NullString{String: "http://test", Valid: true},
+		Input:              "{}",
+		Injected:           true,
+		CreatedAt:          closeBeforeThreshold,
+	})
+
+	// Run the purge with configured retention period
+	done := awaitDoTick(ctx, t, clk)
+	closer := dbpurge.New(ctx, logger, db, &codersdk.DeploymentValues{
+		AI: codersdk.AIConfig{
+			BridgeConfig: codersdk.AIBridgeConfig{
+				Retention: serpent.Duration(retentionPeriod),
+			},
+		},
+	}, clk)
+	defer closer.Close()
+	// Wait for tick
+	testutil.TryReceive(ctx, t, done)
+
+	// Verify results by querying all AI Bridge records
+	interceptions, err := db.GetAIBridgeInterceptions(ctx)
+	require.NoError(t, err)
+
+	// Extract interception IDs for comparison
+	interceptionIDs := make([]uuid.UUID, len(interceptions))
+	for i, interception := range interceptions {
+		interceptionIDs[i] = interception.ID
+	}
+
+	require.NotContains(t, interceptionIDs, oldInterception.ID, "old interception should be deleted")
+	require.NotContains(t, interceptionIDs, oldInterceptionWithRelated.ID, "old interception with related records should be deleted")
+
+	// Verify related records were also deleted
+	oldTokenUsages, err := db.GetAIBridgeTokenUsagesByInterceptionID(ctx, oldInterceptionWithRelated.ID)
+	require.NoError(t, err)
+	require.Empty(t, oldTokenUsages, "old token usages should be deleted")
+
+	oldUserPrompts, err := db.GetAIBridgeUserPromptsByInterceptionID(ctx, oldInterceptionWithRelated.ID)
+	require.NoError(t, err)
+	require.Empty(t, oldUserPrompts, "old user prompts should be deleted")
+
+	oldToolUsages, err := db.GetAIBridgeToolUsagesByInterceptionID(ctx, oldInterceptionWithRelated.ID)
+	require.NoError(t, err)
+	require.Empty(t, oldToolUsages, "old tool usages should be deleted")
+
+	require.Contains(t, interceptionIDs, recentInterception.ID, "recent interception should be kept")
+	require.Contains(t, interceptionIDs, nearThresholdInterception.ID, "near threshold interception should be kept")
+
+	// Verify related records were NOT deleted
+	newTokenUsages, err := db.GetAIBridgeTokenUsagesByInterceptionID(ctx, nearThresholdInterception.ID)
+	require.NoError(t, err)
+	require.Len(t, newTokenUsages, 1, "near threshold token usages should not be deleted")
+
+	newUserPrompts, err := db.GetAIBridgeUserPromptsByInterceptionID(ctx, nearThresholdInterception.ID)
+	require.NoError(t, err)
+	require.Len(t, newUserPrompts, 1, "near threshold user prompts should not be deleted")
+
+	newToolUsages, err := db.GetAIBridgeToolUsagesByInterceptionID(ctx, nearThresholdInterception.ID)
+	require.NoError(t, err)
+	require.Len(t, newToolUsages, 1, "near threshold tool usages should not be deleted")
+}

coderd/database/dump.sql

@@ -1056,7 +1056,8 @@ CREATE TABLE aibridge_interceptions (
     model text NOT NULL,
     started_at timestamp with time zone NOT NULL,
     metadata jsonb,
-    ended_at timestamp with time zone
+    ended_at timestamp with time zone,
+    api_key_id text
 );
 
 COMMENT ON TABLE aibridge_interceptions IS 'Audit log of requests intercepted by AI Bridge';
@@ -1828,6 +1829,15 @@ CREATE TABLE tasks (
     deleted_at timestamp with time zone
 );
 
+CREATE VIEW visible_users AS
+ SELECT users.id,
+    users.username,
+    users.name,
+    users.avatar_url
+   FROM users;
+
+COMMENT ON VIEW visible_users IS 'Visible fields of users are allowed to be joined with other tables for including context of other resources.';
+
 CREATE TABLE workspace_agents (
     id uuid NOT NULL,
     created_at timestamp with time zone NOT NULL,
@@ -1939,9 +1949,7 @@ CREATE TABLE workspace_builds (
     max_deadline timestamp with time zone DEFAULT '0001-01-01 00:00:00+00'::timestamp with time zone NOT NULL,
     template_version_preset_id uuid,
     has_ai_task boolean,
-    ai_task_sidebar_app_id uuid,
     has_external_agent boolean,
-    CONSTRAINT workspace_builds_ai_task_sidebar_app_id_required CHECK (((((has_ai_task IS NULL) OR (has_ai_task = false)) AND (ai_task_sidebar_app_id IS NULL)) OR ((has_ai_task = true) AND (ai_task_sidebar_app_id IS NOT NULL)))),
     CONSTRAINT workspace_builds_deadline_below_max_deadline CHECK ((((deadline <> '0001-01-01 00:00:00+00'::timestamp with time zone) AND (deadline <= max_deadline)) OR (max_deadline = '0001-01-01 00:00:00+00'::timestamp with time zone)))
 );
 
@@ -1957,29 +1965,26 @@ CREATE VIEW tasks_with_status AS
     tasks.created_at,
     tasks.deleted_at,
         CASE
-            WHEN ((tasks.workspace_id IS NULL) OR (latest_build.job_status IS NULL)) THEN 'pending'::task_status
-            WHEN (latest_build.job_status = 'failed'::provisioner_job_status) THEN 'error'::task_status
-            WHEN ((latest_build.transition = ANY (ARRAY['stop'::workspace_transition, 'delete'::workspace_transition])) AND (latest_build.job_status = 'succeeded'::provisioner_job_status)) THEN 'paused'::task_status
-            WHEN ((latest_build.transition = 'start'::workspace_transition) AND (latest_build.job_status = 'pending'::provisioner_job_status)) THEN 'initializing'::task_status
-            WHEN ((latest_build.transition = 'start'::workspace_transition) AND (latest_build.job_status = ANY (ARRAY['running'::provisioner_job_status, 'succeeded'::provisioner_job_status]))) THEN
-            CASE
-                WHEN agent_status."none" THEN 'initializing'::task_status
-                WHEN agent_status.connecting THEN 'initializing'::task_status
-                WHEN agent_status.connected THEN
-                CASE
-                    WHEN app_status.any_unhealthy THEN 'error'::task_status
-                    WHEN app_status.any_initializing THEN 'initializing'::task_status
-                    WHEN app_status.all_healthy_or_disabled THEN 'active'::task_status
-                    ELSE 'unknown'::task_status
-                END
-                ELSE 'unknown'::task_status
-            END
-            ELSE 'unknown'::task_status
+            WHEN (tasks.workspace_id IS NULL) THEN 'pending'::task_status
+            WHEN (build_status.status <> 'active'::task_status) THEN build_status.status
+            WHEN (agent_status.status <> 'active'::task_status) THEN agent_status.status
+            ELSE app_status.status
         END AS status,
+    jsonb_build_object('build', jsonb_build_object('transition', latest_build_raw.transition, 'job_status', latest_build_raw.job_status, 'computed', build_status.status), 'agent', jsonb_build_object('lifecycle_state', agent_raw.lifecycle_state, 'computed', agent_status.status), 'app', jsonb_build_object('health', app_raw.health, 'computed', app_status.status)) AS status_debug,
     task_app.workspace_build_number,
     task_app.workspace_agent_id,
-    task_app.workspace_app_id
-   FROM ((((tasks
+    task_app.workspace_app_id,
+    agent_raw.lifecycle_state AS workspace_agent_lifecycle_state,
+    app_raw.health AS workspace_app_health,
+    task_owner.owner_username,
+    task_owner.owner_name,
+    task_owner.owner_avatar_url
+   FROM ((((((((tasks
+     CROSS JOIN LATERAL ( SELECT vu.username AS owner_username,
+            vu.name AS owner_name,
+            vu.avatar_url AS owner_avatar_url
+           FROM visible_users vu
+          WHERE (vu.id = tasks.owner_id)) task_owner)
      LEFT JOIN LATERAL ( SELECT task_app_1.workspace_build_number,
             task_app_1.workspace_agent_id,
             task_app_1.workspace_app_id
@@ -1992,17 +1997,36 @@ CREATE VIEW tasks_with_status AS
             workspace_build.job_id
            FROM (workspace_builds workspace_build
              JOIN provisioner_jobs provisioner_job ON ((provisioner_job.id = workspace_build.job_id)))
-          WHERE ((workspace_build.workspace_id = tasks.workspace_id) AND (workspace_build.build_number = task_app.workspace_build_number))) latest_build ON (true))
-     CROSS JOIN LATERAL ( SELECT (count(*) = 0) AS "none",
-            bool_or((workspace_agent.lifecycle_state = ANY (ARRAY['created'::workspace_agent_lifecycle_state, 'starting'::workspace_agent_lifecycle_state]))) AS connecting,
-            bool_and((workspace_agent.lifecycle_state = 'ready'::workspace_agent_lifecycle_state)) AS connected
+          WHERE ((workspace_build.workspace_id = tasks.workspace_id) AND (workspace_build.build_number = task_app.workspace_build_number))) latest_build_raw ON (true))
+     LEFT JOIN LATERAL ( SELECT workspace_agent.lifecycle_state
            FROM workspace_agents workspace_agent
-          WHERE (workspace_agent.id = task_app.workspace_agent_id)) agent_status)
-     CROSS JOIN LATERAL ( SELECT bool_or((workspace_app.health = 'unhealthy'::workspace_app_health)) AS any_unhealthy,
-            bool_or((workspace_app.health = 'initializing'::workspace_app_health)) AS any_initializing,
-            bool_and((workspace_app.health = ANY (ARRAY['healthy'::workspace_app_health, 'disabled'::workspace_app_health]))) AS all_healthy_or_disabled
+          WHERE (workspace_agent.id = task_app.workspace_agent_id)) agent_raw ON (true))
+     LEFT JOIN LATERAL ( SELECT workspace_app.health
            FROM workspace_apps workspace_app
-          WHERE (workspace_app.id = task_app.workspace_app_id)) app_status)
+          WHERE (workspace_app.id = task_app.workspace_app_id)) app_raw ON (true))
+     CROSS JOIN LATERAL ( SELECT
+                CASE
+                    WHEN (latest_build_raw.job_status IS NULL) THEN 'pending'::task_status
+                    WHEN (latest_build_raw.job_status = ANY (ARRAY['failed'::provisioner_job_status, 'canceling'::provisioner_job_status, 'canceled'::provisioner_job_status])) THEN 'error'::task_status
+                    WHEN ((latest_build_raw.transition = ANY (ARRAY['stop'::workspace_transition, 'delete'::workspace_transition])) AND (latest_build_raw.job_status = 'succeeded'::provisioner_job_status)) THEN 'paused'::task_status
+                    WHEN ((latest_build_raw.transition = 'start'::workspace_transition) AND (latest_build_raw.job_status = 'pending'::provisioner_job_status)) THEN 'initializing'::task_status
+                    WHEN ((latest_build_raw.transition = 'start'::workspace_transition) AND (latest_build_raw.job_status = ANY (ARRAY['running'::provisioner_job_status, 'succeeded'::provisioner_job_status]))) THEN 'active'::task_status
+                    ELSE 'unknown'::task_status
+                END AS status) build_status)
+     CROSS JOIN LATERAL ( SELECT
+                CASE
+                    WHEN ((agent_raw.lifecycle_state IS NULL) OR (agent_raw.lifecycle_state = ANY (ARRAY['created'::workspace_agent_lifecycle_state, 'starting'::workspace_agent_lifecycle_state]))) THEN 'initializing'::task_status
+                    WHEN (agent_raw.lifecycle_state = ANY (ARRAY['ready'::workspace_agent_lifecycle_state, 'start_timeout'::workspace_agent_lifecycle_state, 'start_error'::workspace_agent_lifecycle_state])) THEN 'active'::task_status
+                    WHEN (agent_raw.lifecycle_state <> ALL (ARRAY['created'::workspace_agent_lifecycle_state, 'starting'::workspace_agent_lifecycle_state, 'ready'::workspace_agent_lifecycle_state, 'start_timeout'::workspace_agent_lifecycle_state, 'start_error'::workspace_agent_lifecycle_state])) THEN 'unknown'::task_status
+                    ELSE 'unknown'::task_status
+                END AS status) agent_status)
+     CROSS JOIN LATERAL ( SELECT
+                CASE
+                    WHEN (app_raw.health = 'initializing'::workspace_app_health) THEN 'initializing'::task_status
+                    WHEN (app_raw.health = 'unhealthy'::workspace_app_health) THEN 'error'::task_status
+                    WHEN (app_raw.health = ANY (ARRAY['healthy'::workspace_app_health, 'disabled'::workspace_app_health])) THEN 'active'::task_status
+                    ELSE 'unknown'::task_status
+                END AS status) app_status)
   WHERE (tasks.deleted_at IS NULL);
 
 CREATE TABLE telemetry_items (
@@ -2146,7 +2170,8 @@ CREATE TABLE template_version_presets (
     scheduling_timezone text DEFAULT ''::text NOT NULL,
     is_default boolean DEFAULT false NOT NULL,
     description character varying(128) DEFAULT ''::character varying NOT NULL,
-    icon character varying(256) DEFAULT ''::character varying NOT NULL
+    icon character varying(256) DEFAULT ''::character varying NOT NULL,
+    last_invalidated_at timestamp with time zone
 );
 
 COMMENT ON COLUMN template_version_presets.description IS 'Short text describing the preset (max 128 characters).';
@@ -2210,15 +2235,6 @@ COMMENT ON COLUMN template_versions.external_auth_providers IS 'IDs of External
 
 COMMENT ON COLUMN template_versions.message IS 'Message describing the changes in this version of the template, similar to a Git commit message. Like a commit message, this should be a short, high-level description of the changes in this version of the template. This message is immutable and should not be updated after the fact.';
 
-CREATE VIEW visible_users AS
- SELECT users.id,
-    users.username,
-    users.name,
-    users.avatar_url
-   FROM users;
-
-COMMENT ON VIEW visible_users IS 'Visible fields of users are allowed to be joined with other tables for including context of other resources.';
-
 CREATE VIEW template_version_with_user AS
  SELECT template_versions.id,
     template_versions.template_id,
@@ -2279,7 +2295,8 @@ CREATE TABLE templates (
     activity_bump bigint DEFAULT '3600000000000'::bigint NOT NULL,
     max_port_sharing_level app_sharing_level DEFAULT 'owner'::app_sharing_level NOT NULL,
     use_classic_parameter_flow boolean DEFAULT false NOT NULL,
-    cors_behavior cors_behavior DEFAULT 'simple'::cors_behavior NOT NULL
+    cors_behavior cors_behavior DEFAULT 'simple'::cors_behavior NOT NULL,
+    use_terraform_workspace_cache boolean DEFAULT false NOT NULL
 );
 
 COMMENT ON COLUMN templates.default_ttl IS 'The default duration for autostop for workspaces created from this template.';
@@ -2302,6 +2319,8 @@ COMMENT ON COLUMN templates.deprecated IS 'If set to a non empty string, the tem
 
 COMMENT ON COLUMN templates.use_classic_parameter_flow IS 'Determines whether to default to the dynamic parameter creation flow for this template or continue using the legacy classic parameter creation flow.This is a template wide setting, the template admin can revert to the classic flow if there are any issues. An escape hatch is required, as workspace creation is a core workflow and cannot break. This column will be removed when the dynamic parameter creation flow is stable.';
 
+COMMENT ON COLUMN templates.use_terraform_workspace_cache IS 'Determines whether to keep terraform directories cached between runs for workspaces created from this template. When enabled, this can significantly speed up the `terraform init` step at the cost of increased disk usage. This is an opt-in experience, as it prevents modules from being updated, and therefore is a behavioral difference from the default.';
+
 CREATE VIEW template_with_names AS
  SELECT templates.id,
     templates.created_at,
@@ -2333,6 +2352,7 @@ CREATE VIEW template_with_names AS
     templates.max_port_sharing_level,
     templates.use_classic_parameter_flow,
     templates.cors_behavior,
+    templates.use_terraform_workspace_cache,
     COALESCE(visible_users.avatar_url, ''::text) AS created_by_avatar_url,
     COALESCE(visible_users.username, ''::text) AS created_by_username,
     COALESCE(visible_users.name, ''::text) AS created_by_name,
@@ -2695,7 +2715,6 @@ CREATE VIEW workspace_build_with_user AS
     workspace_builds.max_deadline,
     workspace_builds.template_version_preset_id,
     workspace_builds.has_ai_task,
-    workspace_builds.ai_task_sidebar_app_id,
     workspace_builds.has_external_agent,
     COALESCE(visible_users.avatar_url, ''::text) AS initiator_by_avatar_url,
     COALESCE(visible_users.username, ''::text) AS initiator_by_username,
@@ -2914,11 +2933,13 @@ CREATE VIEW workspaces_expanded AS
     templates.name AS template_name,
     templates.display_name AS template_display_name,
     templates.icon AS template_icon,
-    templates.description AS template_description
-   FROM (((workspaces
+    templates.description AS template_description,
+    tasks.id AS task_id
+   FROM ((((workspaces
      JOIN visible_users ON ((workspaces.owner_id = visible_users.id)))
      JOIN organizations ON ((workspaces.organization_id = organizations.id)))
-     JOIN templates ON ((workspaces.template_id = templates.id)));
+     JOIN templates ON ((workspaces.template_id = templates.id)))
+     LEFT JOIN tasks ON ((workspaces.id = tasks.workspace_id)));
 
 COMMENT ON VIEW workspaces_expanded IS 'Joins in the display name information such as username, avatar, and organization name.';
 
@@ -3794,9 +3815,6 @@ ALTER TABLE ONLY workspace_apps
 ALTER TABLE ONLY workspace_build_parameters
     ADD CONSTRAINT workspace_build_parameters_workspace_build_id_fkey FOREIGN KEY (workspace_build_id) REFERENCES workspace_builds(id) ON DELETE CASCADE;
 
-ALTER TABLE ONLY workspace_builds
-    ADD CONSTRAINT workspace_builds_ai_task_sidebar_app_id_fkey FOREIGN KEY (ai_task_sidebar_app_id) REFERENCES workspace_apps(id);
-
 ALTER TABLE ONLY workspace_builds
     ADD CONSTRAINT workspace_builds_job_id_fkey FOREIGN KEY (job_id) REFERENCES provisioner_jobs(id) ON DELETE CASCADE;
 

coderd/database/foreign_key_constraint.go

@@ -94,7 +94,6 @@ const (
 	ForeignKeyWorkspaceAppStatusesWorkspaceID                     ForeignKeyConstraint = "workspace_app_statuses_workspace_id_fkey"                        // ALTER TABLE ONLY workspace_app_statuses ADD CONSTRAINT workspace_app_statuses_workspace_id_fkey FOREIGN KEY (workspace_id) REFERENCES workspaces(id);
 	ForeignKeyWorkspaceAppsAgentID                                ForeignKeyConstraint = "workspace_apps_agent_id_fkey"                                    // ALTER TABLE ONLY workspace_apps ADD CONSTRAINT workspace_apps_agent_id_fkey FOREIGN KEY (agent_id) REFERENCES workspace_agents(id) ON DELETE CASCADE;
 	ForeignKeyWorkspaceBuildParametersWorkspaceBuildID            ForeignKeyConstraint = "workspace_build_parameters_workspace_build_id_fkey"              // ALTER TABLE ONLY workspace_build_parameters ADD CONSTRAINT workspace_build_parameters_workspace_build_id_fkey FOREIGN KEY (workspace_build_id) REFERENCES workspace_builds(id) ON DELETE CASCADE;
-	ForeignKeyWorkspaceBuildsAiTaskSidebarAppID                   ForeignKeyConstraint = "workspace_builds_ai_task_sidebar_app_id_fkey"                    // ALTER TABLE ONLY workspace_builds ADD CONSTRAINT workspace_builds_ai_task_sidebar_app_id_fkey FOREIGN KEY (ai_task_sidebar_app_id) REFERENCES workspace_apps(id);
 	ForeignKeyWorkspaceBuildsJobID                                ForeignKeyConstraint = "workspace_builds_job_id_fkey"                                    // ALTER TABLE ONLY workspace_builds ADD CONSTRAINT workspace_builds_job_id_fkey FOREIGN KEY (job_id) REFERENCES provisioner_jobs(id) ON DELETE CASCADE;
 	ForeignKeyWorkspaceBuildsTemplateVersionID                    ForeignKeyConstraint = "workspace_builds_template_version_id_fkey"                       // ALTER TABLE ONLY workspace_builds ADD CONSTRAINT workspace_builds_template_version_id_fkey FOREIGN KEY (template_version_id) REFERENCES template_versions(id) ON DELETE CASCADE;
 	ForeignKeyWorkspaceBuildsTemplateVersionPresetID              ForeignKeyConstraint = "workspace_builds_template_version_preset_id_fkey"                // ALTER TABLE ONLY workspace_builds ADD CONSTRAINT workspace_builds_template_version_preset_id_fkey FOREIGN KEY (template_version_preset_id) REFERENCES template_version_presets(id) ON DELETE SET NULL;

coderd/database/migrations/000391_tasks_with_status_user_fields.down.sql

@@ -0,0 +1,74 @@
+-- Drop view from 000390_tasks_with_status_user_fields.up.sql.
+DROP VIEW IF EXISTS tasks_with_status;
+
+-- Restore from 000382_add_columns_to_tasks_with_status.up.sql.
+CREATE VIEW
+	tasks_with_status
+AS
+	SELECT
+		tasks.*,
+		CASE
+			WHEN tasks.workspace_id IS NULL OR latest_build.job_status IS NULL THEN 'pending'::task_status
+
+			WHEN latest_build.job_status = 'failed' THEN 'error'::task_status
+
+			WHEN latest_build.transition IN ('stop', 'delete')
+				AND latest_build.job_status = 'succeeded' THEN 'paused'::task_status
+
+			WHEN latest_build.transition = 'start'
+				AND latest_build.job_status = 'pending' THEN 'initializing'::task_status
+
+			WHEN latest_build.transition = 'start' AND latest_build.job_status IN ('running', 'succeeded') THEN
+				CASE
+					WHEN agent_status.none THEN 'initializing'::task_status
+					WHEN agent_status.connecting THEN 'initializing'::task_status
+					WHEN agent_status.connected THEN
+						CASE
+							WHEN app_status.any_unhealthy THEN 'error'::task_status
+							WHEN app_status.any_initializing THEN 'initializing'::task_status
+							WHEN app_status.all_healthy_or_disabled THEN 'active'::task_status
+							ELSE 'unknown'::task_status
+						END
+					ELSE 'unknown'::task_status
+				END
+
+			ELSE 'unknown'::task_status
+		END AS status,
+		task_app.*
+	FROM
+		tasks
+	LEFT JOIN LATERAL (
+		SELECT workspace_build_number, workspace_agent_id, workspace_app_id
+		FROM task_workspace_apps task_app
+		WHERE task_id = tasks.id
+		ORDER BY workspace_build_number DESC
+		LIMIT 1
+	) task_app ON TRUE
+	LEFT JOIN LATERAL (
+		SELECT
+			workspace_build.transition,
+			provisioner_job.job_status,
+			workspace_build.job_id
+		FROM workspace_builds workspace_build
+		JOIN provisioner_jobs provisioner_job ON provisioner_job.id = workspace_build.job_id
+		WHERE workspace_build.workspace_id = tasks.workspace_id
+			AND workspace_build.build_number = task_app.workspace_build_number
+	) latest_build ON TRUE
+	CROSS JOIN LATERAL (
+		SELECT
+			COUNT(*) = 0 AS none,
+			bool_or(workspace_agent.lifecycle_state IN ('created', 'starting')) AS connecting,
+			bool_and(workspace_agent.lifecycle_state = 'ready') AS connected
+		FROM workspace_agents workspace_agent
+		WHERE workspace_agent.id = task_app.workspace_agent_id
+	) agent_status
+	CROSS JOIN LATERAL (
+		SELECT
+			bool_or(workspace_app.health = 'unhealthy') AS any_unhealthy,
+			bool_or(workspace_app.health = 'initializing') AS any_initializing,
+			bool_and(workspace_app.health IN ('healthy', 'disabled')) AS all_healthy_or_disabled
+		FROM workspace_apps workspace_app
+		WHERE workspace_app.id = task_app.workspace_app_id
+	) app_status
+	WHERE
+		tasks.deleted_at IS NULL;

coderd/database/migrations/000391_tasks_with_status_user_fields.up.sql

@@ -0,0 +1,84 @@
+-- Drop view from 00037_add_columns_to_tasks_with_status.up.sql.
+DROP VIEW IF EXISTS tasks_with_status;
+
+-- Add owner_name, owner_avatar_url columns.
+CREATE VIEW
+	tasks_with_status
+AS
+	SELECT
+		tasks.*,
+		CASE
+			WHEN tasks.workspace_id IS NULL OR latest_build.job_status IS NULL THEN 'pending'::task_status
+
+			WHEN latest_build.job_status = 'failed' THEN 'error'::task_status
+
+			WHEN latest_build.transition IN ('stop', 'delete')
+				AND latest_build.job_status = 'succeeded' THEN 'paused'::task_status
+
+			WHEN latest_build.transition = 'start'
+				AND latest_build.job_status = 'pending' THEN 'initializing'::task_status
+
+			WHEN latest_build.transition = 'start' AND latest_build.job_status IN ('running', 'succeeded') THEN
+				CASE
+					WHEN agent_status.none THEN 'initializing'::task_status
+					WHEN agent_status.connecting THEN 'initializing'::task_status
+					WHEN agent_status.connected THEN
+						CASE
+							WHEN app_status.any_unhealthy THEN 'error'::task_status
+							WHEN app_status.any_initializing THEN 'initializing'::task_status
+							WHEN app_status.all_healthy_or_disabled THEN 'active'::task_status
+							ELSE 'unknown'::task_status
+						END
+					ELSE 'unknown'::task_status
+				END
+
+			ELSE 'unknown'::task_status
+		END AS status,
+		task_app.*,
+		task_owner.*
+	FROM
+		tasks
+	CROSS JOIN LATERAL (
+		SELECT
+			vu.username AS owner_username,
+			vu.name AS owner_name,
+			vu.avatar_url AS owner_avatar_url
+			FROM visible_users vu
+		WHERE vu.id = tasks.owner_id
+	) task_owner
+	LEFT JOIN LATERAL (
+		SELECT workspace_build_number, workspace_agent_id, workspace_app_id
+		FROM task_workspace_apps task_app
+		WHERE task_id = tasks.id
+		ORDER BY workspace_build_number DESC
+		LIMIT 1
+	) task_app ON TRUE
+	LEFT JOIN LATERAL (
+		SELECT
+			workspace_build.transition,
+			provisioner_job.job_status,
+			workspace_build.job_id
+		FROM workspace_builds workspace_build
+		JOIN provisioner_jobs provisioner_job ON provisioner_job.id = workspace_build.job_id
+		WHERE workspace_build.workspace_id = tasks.workspace_id
+			AND workspace_build.build_number = task_app.workspace_build_number
+	) latest_build ON TRUE
+	CROSS JOIN LATERAL (
+		SELECT
+			COUNT(*) = 0 AS none,
+			bool_or(workspace_agent.lifecycle_state IN ('created', 'starting')) AS connecting,
+			bool_and(workspace_agent.lifecycle_state = 'ready') AS connected
+		FROM workspace_agents workspace_agent
+		WHERE workspace_agent.id = task_app.workspace_agent_id
+	) agent_status
+	CROSS JOIN LATERAL (
+		SELECT
+			bool_or(workspace_app.health = 'unhealthy') AS any_unhealthy,
+			bool_or(workspace_app.health = 'initializing') AS any_initializing,
+			bool_and(workspace_app.health IN ('healthy', 'disabled')) AS all_healthy_or_disabled
+		FROM workspace_apps workspace_app
+		WHERE workspace_app.id = task_app.workspace_app_id
+	) app_status
+	WHERE
+		tasks.deleted_at IS NULL;
+