chore: update react to apply patch for CVE-2025-55182 (not vulnerable)

fix: remove a sensitive field from an agent log line (#20968 ) (#21063 )
This PR removes a log field that could expose sensitive information in agent logs for workspaces that pass such information to the agent via its manifest. (cherry picked from commit 1d726c81bb) Co-authored-by: Sas Swart <sas.swart.cdk@gmail.com>
2025-12-08 19:34:38 +01:00 · 2025-12-02 11:33:50 -06:00 · 2025-12-01 14:16:30 -06:00 · 2025-12-01 14:09:54 -06:00 · 2025-12-01 14:08:50 -06:00 · 2025-12-01 14:08:01 -06:00
924 changed files with 54496 additions and 18597 deletions
@@ -91,6 +91,9 @@

 ## Systematic Debugging Approach

+YOU MUST ALWAYS find the root cause of any issue you are debugging
+YOU MUST NEVER fix a symptom or add a workaround instead of finding a root cause, even if it is faster.
+
 ### Multi-Issue Problem Solving

 When facing multiple failing tests or complex integration issues:
@@ -98,16 +101,21 @@ When facing multiple failing tests or complex integration issues:
 1. **Identify Root Causes**:
   - Run failing tests individually to isolate issues
   - Use LSP tools to trace through call chains
-   - Check both compilation and runtime errors
+   - Read Error Messages Carefully: Check both compilation and runtime errors
+   - Reproduce Consistently: Ensure you can reliably reproduce the issue before investigating
+   - Check Recent Changes: What changed that could have caused this? Git diff, recent commits, etc.
+   - When You Don't Know: Say "I don't understand X" rather than pretending to know

 2. **Fix in Logical Order**:
   - Address compilation issues first (imports, syntax)
   - Fix authorization and RBAC issues next
   - Resolve business logic and validation issues
   - Handle edge cases and race conditions last
+   - IF your first fix doesn't work, STOP and re-analyze rather than adding more fixes

 3. **Verification Strategy**:
-   - Test each fix individually before moving to next issue
+   - Always Test each fix individually before moving to next issue
+   - Verify Before Continuing: Did your test work? If not, form new hypothesis - don't add more fixes
   - Use `make lint` and `make gen` after database changes
   - Verify RFC compliance with actual specifications
   - Run comprehensive test suites before considering complete
@@ -40,11 +40,15 @@
 - Use proper error types
 - Pattern: `xerrors.Errorf("failed to X: %w", err)`

-### Naming Conventions
+## Naming Conventions

- Use clear, descriptive names
- Abbreviate only when obvious
+- Names MUST tell what code does, not how it's implemented or its history
 - Follow Go and TypeScript naming conventions
+- When changing code, never document the old behavior or the behavior change
+- NEVER use implementation details in names (e.g., "ZodValidator", "MCPWrapper", "JSONParser")
+- NEVER use temporal/historical context in names (e.g., "LegacyHandler", "UnifiedTool", "ImprovedInterface", "EnhancedParser")
+- NEVER use pattern names unless they add clarity (e.g., prefer "Tool" over "ToolFactory")
+- Abbreviate only when obvious

 ### Comments

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

@@ -181,7 +181,7 @@ jobs:
          echo "LINT_CACHE_DIR=$dir" >> "$GITHUB_ENV"

      - name: golangci-lint cache
-        uses: actions/cache@0400d5f644dc74513175e3cd8d07132dd4860809 # v4.2.4
+        uses: actions/cache@0057852bfaa89a56745cba8c7296529d2fc39830 # v4.3.0
        with:
          path: |
            ${{ env.LINT_CACHE_DIR }}
@@ -191,7 +191,7 @@ jobs:

      # Check for any typos
      - name: Check for typos
-        uses: crate-ci/typos@85f62a8a84f939ae994ab3763f01a0296d61a7ee # v1.36.2
+        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
@@ -500,17 +494,11 @@ jobs:
          make test

      - name: Upload failed test db dumps
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
        with:
          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

@@ -762,15 +750,23 @@ jobs:

      - name: Upload Playwright Failed Tests
        if: always() && github.actor != 'dependabot[bot]' && runner.os == 'Linux' && !github.event.pull_request.head.repo.fork
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
        with:
          name: failed-test-videos${{ matrix.variant.premium && '-premium' || '' }}
          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${{ matrix.variant.premium && '-premium' || ''  }}
+          path: ./site/e2e/test-results/debug.log
+          retention-days: 7
+
      - name: Upload pprof dumps
        if: always() && github.actor != 'dependabot[bot]' && runner.os == 'Linux' && !github.event.pull_request.head.repo.fork
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
        with:
          name: debug-pprof-dumps${{ matrix.variant.premium && '-premium' || ''  }}
          path: ./site/test-results/**/debug-pprof-*.txt
@@ -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@20c7e42e1b2f6becd5d188df9acb02f3e2f51519 # v13.2.0
+        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@20c7e42e1b2f6becd5d188df9acb02f3e2f51519 # v13.2.0
+        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

@@ -1036,7 +1032,7 @@ jobs:

      - name: Upload build artifacts
        if: ${{ github.repository_owner == 'coder' && (github.ref == 'refs/heads/main' || startsWith(github.ref, 'refs/heads/release/')) }}
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
        with:
          name: dylibs
          path: |
@@ -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

@@ -1123,7 +1119,7 @@ jobs:
          persist-credentials: false

      - name: GHCR Login
-        uses: docker/login-action@184bdaa0721073962dff0199f1fb9940f07167d1 # v3.5.0
+        uses: docker/login-action@5e57cd118135c172c3672efd75eb46360885c0ef # v3.6.0
        with:
          registry: ghcr.io
          username: ${{ github.actor }}
@@ -1201,7 +1197,7 @@ jobs:
        uses: google-github-actions/setup-gcloud@aa5489c8933f4cc7a4f7d45035b3b1440c9c10db # v3.0.1

      - name: Download dylibs
-        uses: actions/download-artifact@634f93cb2916e3fdff6788551b99b062d0335ce0 # v5.0.0
+        uses: actions/download-artifact@018cc2cf5baa6db3ef3c5f8a56943fffe632ef53 # v6.0.0
        with:
          name: dylibs
          path: ./build
@@ -1468,7 +1464,7 @@ jobs:

      - name: Upload build artifacts
        if: github.ref == 'refs/heads/main'
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
        with:
          name: coder
          path: |
@@ -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

@@ -1537,7 +1533,7 @@ jobs:
    steps:
      - name: Send Slack notification
        run: |
-          ESCAPED_PROMPT=$(printf "%s" "<@U08TJ4YNCA3> $BLINK_CI_FAILURE_PROMPT" | jq -Rsa .)
+          ESCAPED_PROMPT=$(printf "%s" "<@U09LQ75AHKR> $BLINK_CI_FAILURE_PROMPT" | jq -Rsa .)
          curl -X POST -H 'Content-type: application/json' \
          --data '{
            "blocks": [
@@ -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

@@ -76,7 +76,7 @@ jobs:
          persist-credentials: false

      - name: GHCR Login
-        uses: docker/login-action@184bdaa0721073962dff0199f1fb9940f07167d1 # v3.5.0
+        uses: docker/login-action@5e57cd118135c172c3672efd75eb46360885c0ef # v3.6.0
        with:
          registry: ghcr.io
          username: ${{ github.actor }}
@@ -92,7 +92,7 @@ jobs:
        uses: google-github-actions/setup-gcloud@aa5489c8933f4cc7a4f7d45035b3b1440c9c10db # v3.0.1

      - name: Set up Flux CLI
-        uses: fluxcd/flux2/action@6bf37f6a560fd84982d67f853162e4b3c2235edb # v2.6.4
+        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 }}
@@ -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}"
@@ -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

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

      - name: Docker login
-        uses: docker/login-action@184bdaa0721073962dff0199f1fb9940f07167d1 # v3.5.0
+        uses: docker/login-action@5e57cd118135c172c3672efd75eb46360885c0ef # v3.6.0
        with:
          registry: ghcr.io
          username: ${{ github.actor }}
@@ -30,7 +30,7 @@ jobs:
      - name: Setup Node
        uses: ./.github/actions/setup-node

-      - uses: tj-actions/changed-files@4563c729c555b4141fac99c80f699f571219b836 # v45.0.7
+      - uses: tj-actions/changed-files@70069877f29101175ed2b055d210fe8b1d54d7d7 # v45.0.7
        id: changed-files
        with:
          files: |
@@ -26,7 +26,7 @@ jobs:
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-4' || 'ubuntu-latest' }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

@@ -36,11 +36,11 @@ jobs:
          persist-credentials: false

      - name: Setup Nix
-        uses: nixbuild/nix-quick-install-action@1f095fee853b33114486cfdeae62fa099cda35a9 # v33
+        uses: nixbuild/nix-quick-install-action@2c9db80fb984ceb1bcaa77cdda3fdf8cfba92035 # v34
        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:
@@ -82,7 +82,7 @@ jobs:

      - name: Login to DockerHub
        if: github.ref == 'refs/heads/main'
-        uses: docker/login-action@184bdaa0721073962dff0199f1fb9940f07167d1 # v3.5.0
+        uses: docker/login-action@5e57cd118135c172c3672efd75eb46360885c0ef # v3.6.0
        with:
          username: ${{ secrets.DOCKERHUB_USERNAME }}
          password: ${{ secrets.DOCKERHUB_PASSWORD }}
@@ -125,7 +125,7 @@ jobs:
      id-token: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

@@ -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

@@ -170,7 +170,7 @@ jobs:
    steps:
      - name: Send Slack notification
        run: |
-          ESCAPED_PROMPT=$(printf "%s" "<@U08TJ4YNCA3> $BLINK_CI_FAILURE_PROMPT" | jq -Rsa .)
+          ESCAPED_PROMPT=$(printf "%s" "<@U09LQ75AHKR> $BLINK_CI_FAILURE_PROMPT" | jq -Rsa .)
          curl -X POST -H 'Content-type: application/json' \
          --data '{
            "blocks": [
@@ -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

@@ -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

@@ -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

@@ -184,12 +184,12 @@ 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

      - name: Find Comment
-        uses: peter-evans/find-comment@3eae4d37986fb5a8592848f6a574fdf654e61f9e # v3.1.0
+        uses: peter-evans/find-comment@b30e6a3c0ed37e7c023ccd3f1db5c6c0b0c23aad # v4.0.0
        id: fc
        with:
          issue-number: ${{ needs.get_info.outputs.PR_NUMBER }}
@@ -199,7 +199,7 @@ jobs:

      - name: Comment on PR
        id: comment_id
-        uses: peter-evans/create-or-update-comment@71345be0265236311c031f5c7866368bd1eff043 # v4.0.0
+        uses: peter-evans/create-or-update-comment@e8674b075228eee787fea43ef493e45ece1004c9 # v5.0.0
        with:
          comment-id: ${{ steps.fc.outputs.comment-id }}
          issue-number: ${{ needs.get_info.outputs.PR_NUMBER }}
@@ -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

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

      - name: GHCR Login
-        uses: docker/login-action@184bdaa0721073962dff0199f1fb9940f07167d1 # v3.5.0
+        uses: docker/login-action@5e57cd118135c172c3672efd75eb46360885c0ef # v3.6.0
        with:
          registry: ghcr.io
          username: ${{ github.actor }}
@@ -288,7 +288,7 @@ jobs:
      PR_HOSTNAME: "pr${{ needs.get_info.outputs.PR_NUMBER }}.${{ secrets.PR_DEPLOYMENTS_DOMAIN }}"
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

@@ -491,7 +491,7 @@ jobs:
          PASSWORD: ${{ steps.setup_deployment.outputs.password }}

      - name: Find Comment
-        uses: peter-evans/find-comment@3eae4d37986fb5a8592848f6a574fdf654e61f9e # v3.1.0
+        uses: peter-evans/find-comment@b30e6a3c0ed37e7c023ccd3f1db5c6c0b0c23aad # v4.0.0
        id: fc
        with:
          issue-number: ${{ env.PR_NUMBER }}
@@ -500,7 +500,7 @@ jobs:
          direction: last

      - name: Comment on PR
-        uses: peter-evans/create-or-update-comment@71345be0265236311c031f5c7866368bd1eff043 # v4.0.0
+        uses: peter-evans/create-or-update-comment@e8674b075228eee787fea43ef493e45ece1004c9 # v5.0.0
        env:
          STATUS: ${{ needs.get_info.outputs.NEW == 'true' && 'Created' || 'Updated' }}
        with:
@@ -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

@@ -131,7 +131,7 @@ jobs:
          AC_CERTIFICATE_PASSWORD_FILE: /tmp/apple_cert_password.txt

      - name: Upload build artifacts
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
        with:
          name: dylibs
          path: |
@@ -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

@@ -239,7 +239,7 @@ jobs:
          cat "$CODER_RELEASE_NOTES_FILE"

      - name: Docker Login
-        uses: docker/login-action@184bdaa0721073962dff0199f1fb9940f07167d1 # v3.5.0
+        uses: docker/login-action@5e57cd118135c172c3672efd75eb46360885c0ef # v3.6.0
        with:
          registry: ghcr.io
          username: ${{ github.actor }}
@@ -327,7 +327,7 @@ jobs:
        uses: google-github-actions/setup-gcloud@aa5489c8933f4cc7a4f7d45035b3b1440c9c10db # v3.0.1

      - name: Download dylibs
-        uses: actions/download-artifact@634f93cb2916e3fdff6788551b99b062d0335ce0 # v5.0.0
+        uses: actions/download-artifact@018cc2cf5baa6db3ef3c5f8a56943fffe632ef53 # v6.0.0
        with:
          name: dylibs
          path: ./build
@@ -761,7 +761,7 @@ jobs:

      - name: Upload artifacts to actions (if dry-run)
        if: ${{ inputs.dry_run }}
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
        with:
          name: release-artifacts
          path: |
@@ -777,7 +777,7 @@ jobs:

      - name: Upload latest sbom artifact to actions (if dry-run)
        if: inputs.dry_run && steps.build_docker.outputs.created_latest_tag == 'true'
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
        with:
          name: latest-sbom-artifact
          path: ./coder_latest_sbom.spdx.json
@@ -785,7 +785,7 @@ jobs:

      - name: Send repository-dispatch event
        if: ${{ !inputs.dry_run }}
-        uses: peter-evans/repository-dispatch@ff45666b9427631e3450c54a1bcbee4d9ff4d7c0 # v3.0.0
+        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

@@ -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

@@ -30,7 +30,7 @@ jobs:
          persist-credentials: false

      - name: "Run analysis"
-        uses: ossf/scorecard-action@05b42c624433fc40578a4040d5cf5e36ddca8cde # v2.4.2
+        uses: ossf/scorecard-action@4eaacf0543bb3f2c246792bd56e8cdeffafb205a # v2.4.3
        with:
          results_file: results.sarif
          results_format: sarif
@@ -39,7 +39,7 @@ jobs:

      # Upload the results as artifacts.
      - name: "Upload artifact"
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
        with:
          name: SARIF file
          path: results.sarif
@@ -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@192325c86100d080feab897ff886c34abd4c83a3 # v3.29.5
+        uses: github/codeql-action/upload-sarif@014f16e7ab1402f30e7c3329d33797e7948572db # v3.29.5
        with:
          sarif_file: results.sarif
@@ -27,7 +27,7 @@ jobs:
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@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@192325c86100d080feab897ff886c34abd4c83a3 # 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@192325c86100d080feab897ff886c34abd4c83a3 # 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

@@ -154,13 +154,13 @@ jobs:
          severity: "CRITICAL,HIGH"

      - name: Upload Trivy scan results to GitHub Security tab
-        uses: github/codeql-action/upload-sarif@192325c86100d080feab897ff886c34abd4c83a3 # v3.29.5
+        uses: github/codeql-action/upload-sarif@014f16e7ab1402f30e7c3329d33797e7948572db # v3.29.5
        with:
          sarif_file: trivy-results.sarif
          category: "Trivy"

      - name: Upload Trivy scan results as an artifact
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
        with:
          name: trivy
          path: trivy-results.sarif
@@ -18,12 +18,12 @@ 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

      - name: stale
-        uses: actions/stale@3a9db7e6a41a89f618792c92c0e97cc736e1b13f # v10.0.0
+        uses: actions/stale@5f858e3efba33a5ca4407a664cc011ad407f2008 # v10.1.0
        with:
          stale-issue-label: "stale"
          stale-pr-label: "stale"
@@ -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@39f0bbed25d76b34de5594dceab824811479e5de # v2.0.6
+        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@39f0bbed25d76b34de5594dceab824811479e5de # v2.0.6
+        uses: Mattraks/delete-workflow-runs@5bf9a1dac5c4d041c029f0a8370ddf0c5cb5aeb7 # v2.1.0
        with:
          token: ${{ github.token }}
          repository: ${{ github.repository }}
@@ -13,12 +13,12 @@ on:
      template_name:
        description: "Coder template to use for workspace"
        required: true
-        default: "traiage"
+        default: "coder"
        type: string
      template_preset:
        description: "Template preset to use"
-        required: true
-        default: "Default"
+        required: false
+        default: ""
        type: string
      prefix:
        description: "Prefix for workspace name"
@@ -66,8 +66,8 @@ jobs:
          GITHUB_EVENT_USER_ID: ${{ github.event.sender.id }}
          GITHUB_EVENT_USER_LOGIN: ${{ github.event.sender.login }}
          INPUTS_ISSUE_URL: ${{ inputs.issue_url }}
-          INPUTS_TEMPLATE_NAME: ${{ inputs.template_name || 'traiage' }}
-          INPUTS_TEMPLATE_PRESET: ${{ inputs.template_preset || 'Default'}}
+          INPUTS_TEMPLATE_NAME: ${{ inputs.template_name || 'coder' }}
+          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}"
-
-      - 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="${GITHUB_USER_ID}" --output=json
-          )
-          coder_username=$(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}"
-
-      - name: Checkout repository
-        uses: actions/checkout@v4
-        with:
-          persist-credentials: false
-          fetch-depth: 0
-
-      # TODO(Cian): this is a good use-case for 'recipes'
-      - name: Create Coder task
-        id: create-task
-        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: ${{ steps.determine-inputs.outputs.template_preset }}
-        run: |
-          # Fetch issue description using `gh` CLI
-          #shellcheck disable=SC2016 # The template string should not be subject to shell expansion
-          issue_description=$(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
+          TASK_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}
+            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
          )
-          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 "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
+          ref: main
+          repository: coder/create-task-action
+
+      - 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:
+          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: |
+          {
+            echo "**Task created:** ${TASK_CREATED}"
+            echo "**Task name:**    ${TASK_NAME}"
+            echo "**Task URL**:     ${TASK_URL}"
+          } >> "${GITHUB_STEP_SUMMARY}"
@@ -9,6 +9,7 @@ IST = "IST"
 MacOS = "macOS"
 AKS = "AKS"
 O_WRONLY = "O_WRONLY"
+AIBridge = "AI Bridge"

 [default.extend-words]
 AKS = "AKS"
@@ -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

@@ -31,7 +31,7 @@ jobs:
          persist-credentials: false

      - name: Check Markdown links
-        uses: umbrelladocs/action-linkspector@874d01cae9fd488e3077b08952093235bd626977 # v1.3.7
+        uses: umbrelladocs/action-linkspector@652f85bc57bb1e7d4327260decc10aa68f7694c3 # v1.4.0
        id: markdown-link-check
        # checks all markdown files from /docs including all subfolders
        with:
@@ -12,6 +12,9 @@ node_modules/
 vendor/
 yarn-error.log

+# Test output files
+test-output/
+
 # VSCode settings.
 **/.vscode/*
 # Allow VSCode recommendations and default settings in project root.
@@ -86,3 +89,8 @@ result
 __debug_bin*

 **/.claude/settings.local.json
+
+/.env
+
+# Ignore plans written by AI agents.
+PLAN.md
@@ -169,6 +169,16 @@ linters-settings:
      - name: var-declaration
      - name: var-naming
      - name: waitgroup-by-value
+  usetesting:
+    # Only os-setenv is enabled because we migrated to usetesting from another linter that
+    # only covered os-setenv.
+    os-setenv: true
+    os-create-temp: false
+    os-mkdir-temp: false
+    os-temp-dir: false
+    os-chdir: false
+    context-background: false
+    context-todo: false

  # irrelevant as of Go v1.22: https://go.dev/blog/loopvar-preview
  govet:
@@ -252,7 +262,6 @@ linters:
    # - wastedassign

    - staticcheck
-    - tenv
    # In Go, it's possible for a package to test it's internal functionality
    # without testing any exported functions. This is enabled to promote
    # decomposing a package before testing it's internals. A function caller
@@ -265,4 +274,5 @@ linters:
    - typecheck
    - unconvert
    - unused
+    - usetesting
    - dupl
@@ -1,11 +1,41 @@
 # Coder Development Guidelines

+You are an experienced, pragmatic software engineer. You don't over-engineer a solution when a simple one is possible.
+Rule #1: If you want exception to ANY rule, YOU MUST STOP and get explicit permission first. BREAKING THE LETTER OR SPIRIT OF THE RULES IS FAILURE.
+
+## Foundational rules
+
+- Doing it right is better than doing it fast. You are not in a rush. NEVER skip steps or take shortcuts.
+- Tedious, systematic work is often the correct solution. Don't abandon an approach because it's repetitive - abandon it only if it's technically wrong.
+- Honesty is a core value.
+
+## Our relationship
+
+- Act as a critical peer reviewer. Your job is to disagree with me when I'm wrong, not to please me. Prioritize accuracy and reasoning over agreement.
+- YOU MUST speak up immediately when you don't know something or we're in over our heads
+- YOU MUST call out bad ideas, unreasonable expectations, and mistakes - I depend on this
+- NEVER be agreeable just to be nice - I NEED your HONEST technical judgment
+- NEVER write the phrase "You're absolutely right!"  You are not a sycophant. We're working together because I value your opinion. Do not agree with me unless you can justify it with evidence or reasoning.
+- YOU MUST ALWAYS STOP and ask for clarification rather than making assumptions.
+- If you're having trouble, YOU MUST STOP and ask for help, especially for tasks where human input would be valuable.
+- When you disagree with my approach, YOU MUST push back. Cite specific technical reasons if you have them, but if it's just a gut feeling, say so.
+- If you're uncomfortable pushing back out loud, just say "Houston, we have a problem". I'll know what you mean
+- We discuss architectutral decisions (framework changes, major refactoring, system design) together before implementation. Routine fixes and clear implementations don't need discussion.
+
+## Proactiveness
+
+When asked to do something, just do it - including obvious follow-up actions needed to complete the task properly.
+Only pause to ask for confirmation when:
+
+- Multiple valid approaches exist and the choice matters
+- The action would delete or significantly restructure existing code
+- You genuinely don't understand what's being asked
+- Your partner asked a question (answer the question, don't jump to implementation)
+
@.claude/docs/WORKFLOWS.md
-@.cursorrules
-@README.md
@package.json

-## 🚀 Essential Commands
+## Essential Commands

 | Task              | Command                  | Notes                            |
 |-------------------|--------------------------|----------------------------------|
@@ -21,22 +51,13 @@
 | **Format**        | `make fmt`               | Auto-format code                 |
 | **Clean**         | `make clean`             | Clean build artifacts            |

-### Frontend Commands (site directory)
-
- `pnpm build` - Build frontend
- `pnpm dev` - Run development server
- `pnpm check` - Run code checks
- `pnpm format` - Format frontend code
- `pnpm lint` - Lint frontend code
- `pnpm test` - Run frontend tests
-
 ### Documentation Commands

 - `pnpm run format-docs` - Format markdown tables in docs
 - `pnpm run lint-docs` - Lint and fix markdown files
 - `pnpm run storybook` - Run Storybook (from site directory)

-## 🔧 Critical Patterns
+## Critical Patterns

 ### Database Changes (ALWAYS FOLLOW)

@@ -78,7 +99,7 @@ app, err := api.Database.GetOAuth2ProviderAppByClientID(dbauthz.AsSystemRestrict
 app, err := api.Database.GetOAuth2ProviderAppByClientID(ctx, clientID)
 ```

-## 📋 Quick Reference
+## Quick Reference

 ### Full workflows available in imported WORKFLOWS.md

@@ -88,14 +109,14 @@ app, err := api.Database.GetOAuth2ProviderAppByClientID(ctx, clientID)
 - [ ] Check if feature touches database - you'll need migrations
 - [ ] Check if feature touches audit logs - update `enterprise/audit/table.go`

-## 🏗️ Architecture
+## Architecture

 - **coderd**: Main API service
 - **provisionerd**: Infrastructure provisioning
 - **Agents**: Workspace services (SSH, port forwarding)
 - **Database**: PostgreSQL with `dbauthz` authorization

-## 🧪 Testing
+## Testing

 ### Race Condition Prevention

@@ -112,21 +133,21 @@ app, err := api.Database.GetOAuth2ProviderAppByClientID(ctx, clientID)
 NEVER use `time.Sleep` to mitigate timing issues. If an issue
 seems like it should use `time.Sleep`, read through https://github.com/coder/quartz and specifically the [README](https://github.com/coder/quartz/blob/main/README.md) to better understand how to handle timing issues.

-## 🎯 Code Style
+## Code Style

 ### Detailed guidelines in imported WORKFLOWS.md

 - Follow [Uber Go Style Guide](https://github.com/uber-go/guide/blob/master/style.md)
 - Commit format: `type(scope): message`

-## 📚 Detailed Development Guides
+## Detailed Development Guides

@.claude/docs/OAUTH2.md
@.claude/docs/TESTING.md
@.claude/docs/TROUBLESHOOTING.md
@.claude/docs/DATABASE.md

-## 🚨 Common Pitfalls
+## Common Pitfalls

 1. **Audit table errors** → Update `enterprise/audit/table.go`
 2. **OAuth2 errors** → Return RFC-compliant format
@@ -18,18 +18,6 @@ coderd/rbac/ @Emyrk
 scripts/apitypings/ @Emyrk
 scripts/gensite/ @aslilac

-site/ @aslilac @Parkreiner
-site/src/hooks/ @Parkreiner
-# These rules intentionally do not specify any owners. More specific rules
-# override less specific rules, so these files are "ignored" by the site/ rule.
-site/e2e/google/protobuf/timestampGenerated.ts
-site/e2e/provisionerGenerated.ts
-site/src/api/countriesGenerated.ts
-site/src/api/rbacresourcesGenerated.ts
-site/src/api/typesGenerated.ts
-site/src/testHelpers/entities.ts
-site/CLAUDE.md
-
 # The blood and guts of the autostop algorithm, which is quite complex and
 # requires elite ball knowledge of most of the scheduling code to make changes
 # without inadvertently affecting other parts of the codebase.
@@ -39,3 +27,5 @@ coderd/schedule/autostop.go @deansheather @DanielleMaywood
 # well as guidance from revenue.
 coderd/usage/ @deansheather @spikecurtis
 enterprise/coderd/usage/ @deansheather @spikecurtis
+
+.github/ 	@jdomeracki-coder
@@ -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 \
@@ -676,6 +677,7 @@ gen/db: $(DB_GEN_FILES)
 .PHONY: gen/db

 gen/golden-files: \
+	agent/unit/testdata/.gen-golden \
 	cli/testdata/.gen-golden \
 	coderd/.gen-golden \
 	coderd/notifications/.gen-golden \
@@ -695,8 +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 \
 		$(DB_GEN_FILES) \
 		site/src/api/typesGenerated.ts \
@@ -767,8 +770,8 @@ codersdk/workspacesdk/agentconnmock/agentconnmock.go: codersdk/workspacesdk/agen
 	go generate ./codersdk/workspacesdk/agentconnmock/
 	touch "$@"

-$(AIBRIDGED_MOCKS): enterprise/x/aibridged/client.go enterprise/x/aibridged/pool.go
-	go generate ./enterprise/x/aibridged/aibridgedmock/
+$(AIBRIDGED_MOCKS): enterprise/aibridged/client.go enterprise/aibridged/pool.go
+	go generate ./enterprise/aibridged/aibridgedmock/
 	touch "$@"

 agent/agentcontainers/dcspec/dcspec_gen.go: \
@@ -799,6 +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=. \
@@ -821,13 +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
@@ -952,6 +963,10 @@ clean/golden-files:
 		-type f -name '*.golden' -delete
 .PHONY: clean/golden-files

+agent/unit/testdata/.gen-golden: $(wildcard agent/unit/testdata/*.golden) $(GO_SRC_FILES) $(wildcard agent/unit/*_test.go)
+	TZ=UTC go test ./agent/unit -run="TestGraph" -update
+	touch "$@"
+
 cli/testdata/.gen-golden: $(wildcard cli/testdata/*.golden) $(wildcard cli/*.tpl) $(GO_SRC_FILES) $(wildcard cli/*_test.go)
 	TZ=UTC go test ./cli -run="Test(CommandHelp|ServerYAML|ErrorExamples|.*Golden)" -update
 	touch "$@"
@@ -1177,3 +1192,8 @@ endif

 dogfood/coder/nix.hash: flake.nix flake.lock
 	sha256sum flake.nix flake.lock >./dogfood/coder/nix.hash
+
+# Count the number of test databases created per test package.
+count-test-databases:
+	PGPASSWORD=postgres psql -h localhost -U postgres -d coder_testing -P pager=off -c 'SELECT test_package, count(*) as count from test_databases GROUP BY test_package ORDER BY count DESC'
+.PHONY: count-test-databases
@@ -8,6 +8,7 @@ import (
 	"fmt"
 	"hash/fnv"
 	"io"
+	"maps"
 	"net"
 	"net/http"
 	"net/netip"
@@ -40,6 +41,7 @@ import (
 	"github.com/coder/coder/v2/agent/agentcontainers"
 	"github.com/coder/coder/v2/agent/agentexec"
 	"github.com/coder/coder/v2/agent/agentscripts"
+	"github.com/coder/coder/v2/agent/agentsocket"
 	"github.com/coder/coder/v2/agent/agentssh"
 	"github.com/coder/coder/v2/agent/proto"
 	"github.com/coder/coder/v2/agent/proto/resourcesmonitor"
@@ -70,16 +72,21 @@ const (
 )

 type Options struct {
-	Filesystem                   afero.Fs
-	LogDir                       string
-	TempDir                      string
-	ScriptDataDir                string
-	Client                       Client
-	ReconnectingPTYTimeout       time.Duration
-	EnvironmentVariables         map[string]string
-	Logger                       slog.Logger
-	IgnorePorts                  map[int]string
-	PortCacheDuration            time.Duration
+	Filesystem             afero.Fs
+	LogDir                 string
+	TempDir                string
+	ScriptDataDir          string
+	Client                 Client
+	ReconnectingPTYTimeout time.Duration
+	EnvironmentVariables   map[string]string
+	Logger                 slog.Logger
+	// IgnorePorts tells the api handler which ports to ignore when
+	// listing all listening ports. This is helpful to hide ports that
+	// are used by the agent, that the user does not care about.
+	IgnorePorts map[int]string
+	// ListeningPortsGetter is used to get the list of listening ports. Only
+	// tests should set this. If unset, a default that queries the OS will be used.
+	ListeningPortsGetter         ListeningPortsGetter
 	SSHMaxTimeout                time.Duration
 	TailnetListenPort            uint16
 	Subsystems                   []codersdk.AgentSubsystem
@@ -91,6 +98,8 @@ type Options struct {
 	Devcontainers                bool
 	DevcontainerAPIOptions       []agentcontainers.Option // Enable Devcontainers for these to be effective.
 	Clock                        quartz.Clock
+	SocketServerEnabled          bool
+	SocketPath                   string // Path for the agent socket server socket
 }

 type Client interface {
@@ -137,9 +146,7 @@ func New(options Options) Agent {
 	if options.ServiceBannerRefreshInterval == 0 {
 		options.ServiceBannerRefreshInterval = 2 * time.Minute
 	}
-	if options.PortCacheDuration == 0 {
-		options.PortCacheDuration = 1 * time.Second
-	}
+
 	if options.Clock == nil {
 		options.Clock = quartz.NewReal()
 	}
@@ -153,30 +160,38 @@ func New(options Options) Agent {
 		options.Execer = agentexec.DefaultExecer
 	}

+	if options.ListeningPortsGetter == nil {
+		options.ListeningPortsGetter = &osListeningPortsGetter{
+			cacheDuration: 1 * time.Second,
+		}
+	}
+
 	hardCtx, hardCancel := context.WithCancel(context.Background())
 	gracefulCtx, gracefulCancel := context.WithCancel(hardCtx)
 	a := &agent{
-		clock:                              options.Clock,
-		tailnetListenPort:                  options.TailnetListenPort,
-		reconnectingPTYTimeout:             options.ReconnectingPTYTimeout,
-		logger:                             options.Logger,
-		gracefulCtx:                        gracefulCtx,
-		gracefulCancel:                     gracefulCancel,
-		hardCtx:                            hardCtx,
-		hardCancel:                         hardCancel,
-		coordDisconnected:                  make(chan struct{}),
-		environmentVariables:               options.EnvironmentVariables,
-		client:                             options.Client,
-		filesystem:                         options.Filesystem,
-		logDir:                             options.LogDir,
-		tempDir:                            options.TempDir,
-		scriptDataDir:                      options.ScriptDataDir,
-		lifecycleUpdate:                    make(chan struct{}, 1),
-		lifecycleReported:                  make(chan codersdk.WorkspaceAgentLifecycle, 1),
-		lifecycleStates:                    []agentsdk.PostLifecycleRequest{{State: codersdk.WorkspaceAgentLifecycleCreated}},
-		reportConnectionsUpdate:            make(chan struct{}, 1),
-		ignorePorts:                        options.IgnorePorts,
-		portCacheDuration:                  options.PortCacheDuration,
+		clock:                   options.Clock,
+		tailnetListenPort:       options.TailnetListenPort,
+		reconnectingPTYTimeout:  options.ReconnectingPTYTimeout,
+		logger:                  options.Logger,
+		gracefulCtx:             gracefulCtx,
+		gracefulCancel:          gracefulCancel,
+		hardCtx:                 hardCtx,
+		hardCancel:              hardCancel,
+		coordDisconnected:       make(chan struct{}),
+		environmentVariables:    options.EnvironmentVariables,
+		client:                  options.Client,
+		filesystem:              options.Filesystem,
+		logDir:                  options.LogDir,
+		tempDir:                 options.TempDir,
+		scriptDataDir:           options.ScriptDataDir,
+		lifecycleUpdate:         make(chan struct{}, 1),
+		lifecycleReported:       make(chan codersdk.WorkspaceAgentLifecycle, 1),
+		lifecycleStates:         []agentsdk.PostLifecycleRequest{{State: codersdk.WorkspaceAgentLifecycleCreated}},
+		reportConnectionsUpdate: make(chan struct{}, 1),
+		listeningPortsHandler: listeningPortsHandler{
+			getter:      options.ListeningPortsGetter,
+			ignorePorts: maps.Clone(options.IgnorePorts),
+		},
 		reportMetadataInterval:             options.ReportMetadataInterval,
 		announcementBannersRefreshInterval: options.ServiceBannerRefreshInterval,
 		sshMaxTimeout:                      options.SSHMaxTimeout,
@@ -190,6 +205,8 @@ func New(options Options) Agent {

 		devcontainers:       options.Devcontainers,
 		containerAPIOptions: options.DevcontainerAPIOptions,
+		socketPath:          options.SocketPath,
+		socketServerEnabled: options.SocketServerEnabled,
 	}
 	// Initially, we have a closed channel, reflecting the fact that we are not initially connected.
 	// Each time we connect we replace the channel (while holding the closeMutex) with a new one
@@ -202,20 +219,16 @@ func New(options Options) Agent {
 }

 type agent struct {
-	clock             quartz.Clock
-	logger            slog.Logger
-	client            Client
-	tailnetListenPort uint16
-	filesystem        afero.Fs
-	logDir            string
-	tempDir           string
-	scriptDataDir     string
-	// ignorePorts tells the api handler which ports to ignore when
-	// listing all listening ports. This is helpful to hide ports that
-	// are used by the agent, that the user does not care about.
-	ignorePorts       map[int]string
-	portCacheDuration time.Duration
-	subsystems        []codersdk.AgentSubsystem
+	clock                 quartz.Clock
+	logger                slog.Logger
+	client                Client
+	tailnetListenPort     uint16
+	filesystem            afero.Fs
+	logDir                string
+	tempDir               string
+	scriptDataDir         string
+	listeningPortsHandler listeningPortsHandler
+	subsystems            []codersdk.AgentSubsystem

 	reconnectingPTYTimeout time.Duration
 	reconnectingPTYServer  *reconnectingpty.Server
@@ -271,6 +284,10 @@ type agent struct {
 	devcontainers       bool
 	containerAPIOptions []agentcontainers.Option
 	containerAPI        *agentcontainers.API
+
+	socketServerEnabled bool
+	socketPath          string
+	socketServer        *agentsocket.Server
 }

 func (a *agent) TailnetConn() *tailnet.Conn {
@@ -350,9 +367,32 @@ func (a *agent) init() {
 			s.ExperimentalContainers = a.devcontainers
 		},
 	)
+
+	a.initSocketServer()
+
 	go a.runLoop()
 }

+// initSocketServer initializes server that allows direct communication with a workspace agent using IPC.
+func (a *agent) initSocketServer() {
+	if !a.socketServerEnabled {
+		a.logger.Info(a.hardCtx, "socket server is disabled")
+		return
+	}
+
+	server, err := agentsocket.NewServer(
+		a.logger.Named("socket"),
+		agentsocket.WithPath(a.socketPath),
+	)
+	if err != nil {
+		a.logger.Warn(a.hardCtx, "failed to create socket server", slog.Error(err), slog.F("path", a.socketPath))
+		return
+	}
+
+	a.socketServer = server
+	a.logger.Debug(a.hardCtx, "socket server started", slog.F("path", a.socketPath))
+}
+
 // runLoop attempts to start the agent in a retry loop.
 // Coder may be offline temporarily, a connection issue
 // may be happening, but regardless after the intermittent
@@ -1087,7 +1127,7 @@ func (a *agent) handleManifest(manifestOK *checkpoint) func(ctx context.Context,
 		if err != nil {
 			return xerrors.Errorf("fetch metadata: %w", err)
 		}
-		a.logger.Info(ctx, "fetched manifest", slog.F("manifest", mp))
+		a.logger.Info(ctx, "fetched manifest")
 		manifest, err := agentsdk.ManifestFromProto(mp)
 		if err != nil {
 			a.logger.Critical(ctx, "failed to convert manifest", slog.F("manifest", mp), slog.Error(err))
@@ -1920,6 +1960,7 @@ func (a *agent) Close() error {
 			lifecycleState = codersdk.WorkspaceAgentLifecycleShutdownError
 		}
 	}
+
 	a.setLifecycle(lifecycleState)

 	err = a.scriptRunner.Close()
@@ -1927,6 +1968,12 @@ func (a *agent) Close() error {
 		a.logger.Error(a.hardCtx, "script runner close", slog.Error(err))
 	}

+	if a.socketServer != nil {
+		if err := a.socketServer.Close(); err != nil {
+			a.logger.Error(a.hardCtx, "socket server close", slog.Error(err))
+		}
+	}
+
 	if err := a.containerAPI.Close(); err != nil {
 		a.logger.Error(a.hardCtx, "container API close", slog.Error(err))
 	}
@@ -3462,11 +3462,7 @@ func TestAgent_Metrics_SSH(t *testing.T) {
 	registry := prometheus.NewRegistry()

 	//nolint:dogsled
-	conn, _, _, _, _ := setupAgent(t, agentsdk.Manifest{
-		// Make sure we always get a DERP connection for
-		// currently_reachable_peers.
-		DisableDirectConnections: true,
-	}, 0, func(_ *agenttest.Client, o *agent.Options) {
+	conn, _, _, _, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, o *agent.Options) {
 		o.PrometheusRegistry = registry
 	})

@@ -3481,16 +3477,31 @@ func TestAgent_Metrics_SSH(t *testing.T) {
 	err = session.Shell()
 	require.NoError(t, err)

-	expected := []*proto.Stats_Metric{
+	expected := []struct {
+		Name    string
+		Type    proto.Stats_Metric_Type
+		CheckFn func(float64) error
+		Labels  []*proto.Stats_Metric_Label
+	}{
 		{
-			Name:  "agent_reconnecting_pty_connections_total",
-			Type:  proto.Stats_Metric_COUNTER,
-			Value: 0,
+			Name: "agent_reconnecting_pty_connections_total",
+			Type: proto.Stats_Metric_COUNTER,
+			CheckFn: func(v float64) error {
+				if v == 0 {
+					return nil
+				}
+				return xerrors.Errorf("expected 0, got %f", v)
+			},
 		},
 		{
-			Name:  "agent_sessions_total",
-			Type:  proto.Stats_Metric_COUNTER,
-			Value: 1,
+			Name: "agent_sessions_total",
+			Type: proto.Stats_Metric_COUNTER,
+			CheckFn: func(v float64) error {
+				if v == 1 {
+					return nil
+				}
+				return xerrors.Errorf("expected 1, got %f", v)
+			},
 			Labels: []*proto.Stats_Metric_Label{
 				{
 					Name:  "magic_type",
@@ -3503,24 +3514,44 @@ func TestAgent_Metrics_SSH(t *testing.T) {
 			},
 		},
 		{
-			Name:  "agent_ssh_server_failed_connections_total",
-			Type:  proto.Stats_Metric_COUNTER,
-			Value: 0,
+			Name: "agent_ssh_server_failed_connections_total",
+			Type: proto.Stats_Metric_COUNTER,
+			CheckFn: func(v float64) error {
+				if v == 0 {
+					return nil
+				}
+				return xerrors.Errorf("expected 0, got %f", v)
+			},
 		},
 		{
-			Name:  "agent_ssh_server_sftp_connections_total",
-			Type:  proto.Stats_Metric_COUNTER,
-			Value: 0,
+			Name: "agent_ssh_server_sftp_connections_total",
+			Type: proto.Stats_Metric_COUNTER,
+			CheckFn: func(v float64) error {
+				if v == 0 {
+					return nil
+				}
+				return xerrors.Errorf("expected 0, got %f", v)
+			},
 		},
 		{
-			Name:  "agent_ssh_server_sftp_server_errors_total",
-			Type:  proto.Stats_Metric_COUNTER,
-			Value: 0,
+			Name: "agent_ssh_server_sftp_server_errors_total",
+			Type: proto.Stats_Metric_COUNTER,
+			CheckFn: func(v float64) error {
+				if v == 0 {
+					return nil
+				}
+				return xerrors.Errorf("expected 0, got %f", v)
+			},
 		},
 		{
-			Name:  "coderd_agentstats_currently_reachable_peers",
-			Type:  proto.Stats_Metric_GAUGE,
-			Value: 1,
+			Name: "coderd_agentstats_currently_reachable_peers",
+			Type: proto.Stats_Metric_GAUGE,
+			CheckFn: func(float64) error {
+				// We can't reliably ping a peer here, and networking is out of
+				// scope of this test, so we just test that the metric exists
+				// with the correct labels.
+				return nil
+			},
 			Labels: []*proto.Stats_Metric_Label{
 				{
 					Name:  "connection_type",
@@ -3529,9 +3560,11 @@ func TestAgent_Metrics_SSH(t *testing.T) {
 			},
 		},
 		{
-			Name:  "coderd_agentstats_currently_reachable_peers",
-			Type:  proto.Stats_Metric_GAUGE,
-			Value: 0,
+			Name: "coderd_agentstats_currently_reachable_peers",
+			Type: proto.Stats_Metric_GAUGE,
+			CheckFn: func(float64) error {
+				return nil
+			},
 			Labels: []*proto.Stats_Metric_Label{
 				{
 					Name:  "connection_type",
@@ -3540,9 +3573,20 @@ func TestAgent_Metrics_SSH(t *testing.T) {
 			},
 		},
 		{
-			Name:  "coderd_agentstats_startup_script_seconds",
-			Type:  proto.Stats_Metric_GAUGE,
-			Value: 1,
+			Name: "coderd_agentstats_startup_script_seconds",
+			Type: proto.Stats_Metric_GAUGE,
+			CheckFn: func(f float64) error {
+				if f >= 0 {
+					return nil
+				}
+				return xerrors.Errorf("expected >= 0, got %f", f)
+			},
+			Labels: []*proto.Stats_Metric_Label{
+				{
+					Name:  "success",
+					Value: "true",
+				},
+			},
 		},
 	}

@@ -3564,11 +3608,10 @@ func TestAgent_Metrics_SSH(t *testing.T) {
 		for _, m := range mf.GetMetric() {
 			assert.Equal(t, expected[i].Name, mf.GetName())
 			assert.Equal(t, expected[i].Type.String(), mf.GetType().String())
-			// Value is max expected
 			if expected[i].Type == proto.Stats_Metric_GAUGE {
-				assert.GreaterOrEqualf(t, expected[i].Value, m.GetGauge().GetValue(), "expected %s to be greater than or equal to %f, got %f", expected[i].Name, expected[i].Value, m.GetGauge().GetValue())
+				assert.NoError(t, expected[i].CheckFn(m.GetGauge().GetValue()), "check fn for %s failed", expected[i].Name)
 			} else if expected[i].Type == proto.Stats_Metric_COUNTER {
-				assert.GreaterOrEqualf(t, expected[i].Value, m.GetCounter().GetValue(), "expected %s to be greater than or equal to %f, got %f", expected[i].Name, expected[i].Value, m.GetCounter().GetValue())
+				assert.NoError(t, expected[i].CheckFn(m.GetCounter().GetValue()), "check fn for %s failed", expected[i].Name)
 			}
 			for j, lbl := range expected[i].Labels {
 				assert.Equal(t, m.GetLabel()[j], &promgo.LabelPair{
@@ -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.
@@ -0,0 +1,146 @@
+package agentsocket
+
+import (
+	"context"
+
+	"golang.org/x/xerrors"
+	"storj.io/drpc"
+	"storj.io/drpc/drpcconn"
+
+	"github.com/coder/coder/v2/agent/agentsocket/proto"
+	"github.com/coder/coder/v2/agent/unit"
+)
+
+// Option represents a configuration option for NewClient.
+type Option func(*options)
+
+type options struct {
+	path string
+}
+
+// WithPath sets the socket path. If not provided or empty, the client will
+// auto-discover the default socket path.
+func WithPath(path string) Option {
+	return func(opts *options) {
+		if path == "" {
+			return
+		}
+		opts.path = path
+	}
+}
+
+// Client provides a client for communicating with the workspace agentsocket API.
+type Client struct {
+	client proto.DRPCAgentSocketClient
+	conn   drpc.Conn
+}
+
+// NewClient creates a new socket client and opens a connection to the socket.
+// If path is not provided via WithPath or is empty, it will auto-discover the
+// default socket path.
+func NewClient(ctx context.Context, opts ...Option) (*Client, error) {
+	options := &options{}
+	for _, opt := range opts {
+		opt(options)
+	}
+
+	conn, err := dialSocket(ctx, options.path)
+	if err != nil {
+		return nil, xerrors.Errorf("connect to socket: %w", err)
+	}
+
+	drpcConn := drpcconn.New(conn)
+	client := proto.NewDRPCAgentSocketClient(drpcConn)
+
+	return &Client{
+		client: client,
+		conn:   drpcConn,
+	}, nil
+}
+
+// Close closes the socket connection.
+func (c *Client) Close() error {
+	return c.conn.Close()
+}
+
+// Ping sends a ping request to the agent.
+func (c *Client) Ping(ctx context.Context) error {
+	_, err := c.client.Ping(ctx, &proto.PingRequest{})
+	return err
+}
+
+// SyncStart starts a unit in the dependency graph.
+func (c *Client) SyncStart(ctx context.Context, unitName unit.ID) error {
+	_, err := c.client.SyncStart(ctx, &proto.SyncStartRequest{
+		Unit: string(unitName),
+	})
+	return err
+}
+
+// SyncWant declares a dependency between units.
+func (c *Client) SyncWant(ctx context.Context, unitName, dependsOn unit.ID) error {
+	_, err := c.client.SyncWant(ctx, &proto.SyncWantRequest{
+		Unit:      string(unitName),
+		DependsOn: string(dependsOn),
+	})
+	return err
+}
+
+// SyncComplete marks a unit as complete in the dependency graph.
+func (c *Client) SyncComplete(ctx context.Context, unitName unit.ID) error {
+	_, err := c.client.SyncComplete(ctx, &proto.SyncCompleteRequest{
+		Unit: string(unitName),
+	})
+	return err
+}
+
+// SyncReady requests whether a unit is ready to be started. That is, all dependencies are satisfied.
+func (c *Client) SyncReady(ctx context.Context, unitName unit.ID) (bool, error) {
+	resp, err := c.client.SyncReady(ctx, &proto.SyncReadyRequest{
+		Unit: string(unitName),
+	})
+	return resp.Ready, err
+}
+
+// SyncStatus gets the status of a unit and its dependencies.
+func (c *Client) SyncStatus(ctx context.Context, unitName unit.ID) (SyncStatusResponse, error) {
+	resp, err := c.client.SyncStatus(ctx, &proto.SyncStatusRequest{
+		Unit: string(unitName),
+	})
+	if err != nil {
+		return SyncStatusResponse{}, err
+	}
+
+	var dependencies []DependencyInfo
+	for _, dep := range resp.Dependencies {
+		dependencies = append(dependencies, DependencyInfo{
+			DependsOn:      unit.ID(dep.DependsOn),
+			RequiredStatus: unit.Status(dep.RequiredStatus),
+			CurrentStatus:  unit.Status(dep.CurrentStatus),
+			IsSatisfied:    dep.IsSatisfied,
+		})
+	}
+
+	return SyncStatusResponse{
+		UnitName:     unitName,
+		Status:       unit.Status(resp.Status),
+		IsReady:      resp.IsReady,
+		Dependencies: dependencies,
+	}, nil
+}
+
+// SyncStatusResponse contains the status information for a unit.
+type SyncStatusResponse struct {
+	UnitName     unit.ID          `table:"unit,default_sort" json:"unit_name"`
+	Status       unit.Status      `table:"status" json:"status"`
+	IsReady      bool             `table:"ready" json:"is_ready"`
+	Dependencies []DependencyInfo `table:"dependencies" json:"dependencies"`
+}
+
+// DependencyInfo contains information about a unit dependency.
+type DependencyInfo struct {
+	DependsOn      unit.ID     `table:"depends on,default_sort" json:"depends_on"`
+	RequiredStatus unit.Status `table:"required status" json:"required_status"`
+	CurrentStatus  unit.Status `table:"current status" json:"current_status"`
+	IsSatisfied    bool        `table:"satisfied" json:"is_satisfied"`
+}
@@ -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
+}
@@ -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);
+}
@@ -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()
+}
@@ -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)
@@ -0,0 +1,138 @@
+package agentsocket
+
+import (
+	"context"
+	"errors"
+	"net"
+	"sync"
+
+	"golang.org/x/xerrors"
+	"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
+}
+
+// NewServer creates a new agent socket server.
+func NewServer(logger slog.Logger, opts ...Option) (*Server, error) {
+	options := &options{}
+	for _, opt := range opts {
+		opt(options)
+	}
+
+	logger = logger.Named("agentsocket-server")
+	server := &Server{
+		logger: logger,
+		path:   options.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))
+		},
+	})
+
+	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
+}
+
+// Close stops the server and cleans up resources.
+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
+	}
+
+	err := s.drpcServer.Serve(s.ctx, listener)
+	if err != nil {
+		s.logger.Warn(s.ctx, "error serving drpc server", slog.Error(err))
+	}
+}
@@ -0,0 +1,138 @@
+package agentsocket_test
+
+import (
+	"context"
+	"path/filepath"
+	"runtime"
+	"testing"
+
+	"github.com/google/uuid"
+	"github.com/spf13/afero"
+	"github.com/stretchr/testify/require"
+
+	"cdr.dev/slog"
+	"github.com/coder/coder/v2/agent"
+	"github.com/coder/coder/v2/agent/agentsocket"
+	"github.com/coder/coder/v2/agent/agenttest"
+	agentproto "github.com/coder/coder/v2/agent/proto"
+	"github.com/coder/coder/v2/codersdk/agentsdk"
+	"github.com/coder/coder/v2/tailnet"
+	"github.com/coder/coder/v2/tailnet/tailnettest"
+	"github.com/coder/coder/v2/testutil"
+)
+
+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(logger, agentsocket.WithPath(socketPath))
+		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(logger, agentsocket.WithPath(socketPath))
+		require.NoError(t, err)
+		defer server1.Close()
+		_, err = agentsocket.NewServer(logger, agentsocket.WithPath(socketPath))
+		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(logger, agentsocket.WithPath(socketPath))
+		require.NoError(t, err)
+		require.NoError(t, server.Close())
+	})
+}
+
+func TestServerWindowsNotSupported(t *testing.T) {
+	t.Parallel()
+
+	if runtime.GOOS != "windows" {
+		t.Skip("this test only runs on Windows")
+	}
+
+	t.Run("NewServer", func(t *testing.T) {
+		t.Parallel()
+
+		socketPath := filepath.Join(t.TempDir(), "test.sock")
+		logger := slog.Make().Leveled(slog.LevelDebug)
+		_, err := agentsocket.NewServer(logger, agentsocket.WithPath(socketPath))
+		require.ErrorContains(t, err, "agentsocket is not supported on Windows")
+	})
+
+	t.Run("NewClient", func(t *testing.T) {
+		t.Parallel()
+
+		_, err := agentsocket.NewClient(context.Background(), agentsocket.WithPath("test.sock"))
+		require.ErrorContains(t, err, "agentsocket is not supported on Windows")
+	})
+}
+
+func TestAgentInitializesOnWindowsWithoutSocketServer(t *testing.T) {
+	t.Parallel()
+
+	if runtime.GOOS != "windows" {
+		t.Skip("this test only runs on Windows")
+	}
+
+	ctx := testutil.Context(t, testutil.WaitShort)
+	logger := testutil.Logger(t).Named("agent")
+
+	derpMap, _ := tailnettest.RunDERPAndSTUN(t)
+
+	coordinator := tailnet.NewCoordinator(logger)
+	t.Cleanup(func() {
+		_ = coordinator.Close()
+	})
+
+	statsCh := make(chan *agentproto.Stats, 50)
+	agentID := uuid.New()
+	manifest := agentsdk.Manifest{
+		AgentID:       agentID,
+		AgentName:     "test-agent",
+		WorkspaceName: "test-workspace",
+		OwnerName:     "test-user",
+		WorkspaceID:   uuid.New(),
+		DERPMap:       derpMap,
+	}
+
+	client := agenttest.NewClient(t, logger.Named("agenttest"), agentID, manifest, statsCh, coordinator)
+	t.Cleanup(client.Close)
+
+	options := agent.Options{
+		Client:                 client,
+		Filesystem:             afero.NewMemMapFs(),
+		Logger:                 logger.Named("agent"),
+		ReconnectingPTYTimeout: testutil.WaitShort,
+		EnvironmentVariables:   map[string]string{},
+		SocketPath:             "",
+	}
+
+	agnt := agent.New(options)
+	t.Cleanup(func() {
+		_ = agnt.Close()
+	})
+
+	startup := testutil.TryReceive(ctx, t, client.GetStartup())
+	require.NotNil(t, startup, "agent should send startup message")
+
+	err := agnt.Close()
+	require.NoError(t, err, "agent should close cleanly")
+}
@@ -0,0 +1,152 @@
+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")
+
+// DRPCAgentSocketService implements the DRPC agent socket service.
+type DRPCAgentSocketService struct {
+	unitManager *unit.Manager
+	logger      slog.Logger
+}
+
+// Ping responds to a ping request to check if the service is alive.
+func (*DRPCAgentSocketService) Ping(_ context.Context, _ *proto.PingRequest) (*proto.PingResponse, error) {
+	return &proto.PingResponse{}, nil
+}
+
+// SyncStart starts a unit in the dependency graph.
+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
+}
+
+// SyncWant declares a dependency between units.
+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
+}
+
+// SyncComplete marks a unit as complete in the dependency graph.
+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
+}
+
+// SyncReady checks whether a unit is ready to be started. That is, all dependencies are satisfied.
+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
+}
+
+// SyncStatus gets the status of a unit and lists its dependencies.
+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)
+	switch {
+	case errors.Is(err, unit.ErrUnitNotFound):
+		dependencies = []unit.Dependency{}
+	case err != nil:
+		return nil, xerrors.Errorf("cannot 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
+}
@@ -0,0 +1,389 @@
+package agentsocket_test
+
+import (
+	"context"
+	"crypto/sha256"
+	"encoding/hex"
+	"fmt"
+	"os"
+	"path/filepath"
+	"runtime"
+	"testing"
+
+	"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/unit"
+	"github.com/coder/coder/v2/testutil"
+)
+
+// 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(ctx context.Context, t *testing.T, socketPath string) *agentsocket.Client {
+	t.Helper()
+
+	client, err := agentsocket.NewClient(ctx, agentsocket.WithPath(socketPath))
+	t.Cleanup(func() {
+		_ = client.Close()
+	})
+	require.NoError(t, err)
+
+	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")
+		ctx := testutil.Context(t, testutil.WaitShort)
+		server, err := agentsocket.NewServer(
+			slog.Make().Leveled(slog.LevelDebug),
+			agentsocket.WithPath(socketPath),
+		)
+		require.NoError(t, err)
+		defer server.Close()
+
+		client := newSocketClient(ctx, t, socketPath)
+
+		err = client.Ping(ctx)
+		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")
+			ctx := testutil.Context(t, testutil.WaitShort)
+			server, err := agentsocket.NewServer(
+				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(ctx, t, socketPath)
+
+			err = client.SyncStart(ctx, "test-unit")
+			require.NoError(t, err)
+
+			status, err := client.SyncStatus(ctx, "test-unit")
+			require.NoError(t, err)
+			require.Equal(t, unit.StatusStarted, status.Status)
+		})
+
+		t.Run("UnitAlreadyStarted", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+			ctx := testutil.Context(t, testutil.WaitShort)
+			server, err := agentsocket.NewServer(
+				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(ctx, t, socketPath)
+
+			// First Start
+			err = client.SyncStart(ctx, "test-unit")
+			require.NoError(t, err)
+			status, err := client.SyncStatus(ctx, "test-unit")
+			require.NoError(t, err)
+			require.Equal(t, unit.StatusStarted, status.Status)
+
+			// Second Start
+			err = client.SyncStart(ctx, "test-unit")
+			require.ErrorContains(t, err, unit.ErrSameStatusAlreadySet.Error())
+
+			status, err = client.SyncStatus(ctx, "test-unit")
+			require.NoError(t, err)
+			require.Equal(t, unit.StatusStarted, status.Status)
+		})
+
+		t.Run("UnitAlreadyCompleted", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+			ctx := testutil.Context(t, testutil.WaitShort)
+			server, err := agentsocket.NewServer(
+				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(ctx, t, socketPath)
+
+			// First start
+			err = client.SyncStart(ctx, "test-unit")
+			require.NoError(t, err)
+
+			status, err := client.SyncStatus(ctx, "test-unit")
+			require.NoError(t, err)
+			require.Equal(t, unit.StatusStarted, status.Status)
+
+			// Complete the unit
+			err = client.SyncComplete(ctx, "test-unit")
+			require.NoError(t, err)
+
+			status, err = client.SyncStatus(ctx, "test-unit")
+			require.NoError(t, err)
+			require.Equal(t, unit.StatusComplete, status.Status)
+
+			// Second start
+			err = client.SyncStart(ctx, "test-unit")
+			require.NoError(t, err)
+
+			status, err = client.SyncStatus(ctx, "test-unit")
+			require.NoError(t, err)
+			require.Equal(t, unit.StatusStarted, status.Status)
+		})
+
+		t.Run("UnitNotReady", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+			ctx := testutil.Context(t, testutil.WaitShort)
+			server, err := agentsocket.NewServer(
+				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(ctx, t, socketPath)
+
+			err = client.SyncWant(ctx, "test-unit", "dependency-unit")
+			require.NoError(t, err)
+
+			err = client.SyncStart(ctx, "test-unit")
+			require.ErrorContains(t, err, "unit not ready")
+
+			status, err := client.SyncStatus(ctx, "test-unit")
+			require.NoError(t, err)
+			require.Equal(t, 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")
+			ctx := testutil.Context(t, testutil.WaitShort)
+			server, err := agentsocket.NewServer(
+				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(ctx, t, socketPath)
+
+			// If dependency units are not registered, they are registered automatically
+			err = client.SyncWant(ctx, "test-unit", "dependency-unit")
+			require.NoError(t, err)
+
+			status, err := client.SyncStatus(ctx, "test-unit")
+			require.NoError(t, err)
+			require.Len(t, status.Dependencies, 1)
+			require.Equal(t, unit.ID("dependency-unit"), status.Dependencies[0].DependsOn)
+			require.Equal(t, unit.StatusComplete, status.Dependencies[0].RequiredStatus)
+		})
+
+		t.Run("DependencyAlreadyRegistered", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+			ctx := testutil.Context(t, testutil.WaitShort)
+			server, err := agentsocket.NewServer(
+				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(ctx, t, socketPath)
+
+			// Start the dependency unit
+			err = client.SyncStart(ctx, "dependency-unit")
+			require.NoError(t, err)
+
+			status, err := client.SyncStatus(ctx, "dependency-unit")
+			require.NoError(t, err)
+			require.Equal(t, unit.StatusStarted, status.Status)
+
+			// Add the dependency after the dependency unit has already started
+			err = client.SyncWant(ctx, "test-unit", "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(ctx, "test-unit")
+			require.NoError(t, err)
+			require.Equal(t, unit.ID("dependency-unit"), status.Dependencies[0].DependsOn)
+			require.Equal(t, unit.StatusComplete, status.Dependencies[0].RequiredStatus)
+		})
+
+		t.Run("DependencyAddedAfterDependentStarted", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+			ctx := testutil.Context(t, testutil.WaitShort)
+			server, err := agentsocket.NewServer(
+				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(ctx, t, socketPath)
+
+			// Start the dependent unit
+			err = client.SyncStart(ctx, "test-unit")
+			require.NoError(t, err)
+
+			status, err := client.SyncStatus(ctx, "test-unit")
+			require.NoError(t, err)
+			require.Equal(t, unit.StatusStarted, status.Status)
+
+			// Add the dependency after the dependency unit has already started
+			err = client.SyncWant(ctx, "test-unit", "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(ctx, "test-unit")
+			require.NoError(t, err)
+			require.Equal(t, unit.ID("dependency-unit"), status.Dependencies[0].DependsOn)
+			require.Equal(t, unit.StatusComplete, 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")
+			ctx := testutil.Context(t, testutil.WaitShort)
+			server, err := agentsocket.NewServer(
+				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(ctx, t, socketPath)
+
+			ready, err := client.SyncReady(ctx, "unregistered-unit")
+			require.NoError(t, err)
+			require.True(t, ready)
+		})
+
+		t.Run("UnitNotReady", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+			ctx := testutil.Context(t, testutil.WaitShort)
+			server, err := agentsocket.NewServer(
+				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(ctx, t, socketPath)
+
+			// Register a unit with an unsatisfied dependency
+			err = client.SyncWant(ctx, "test-unit", "dependency-unit")
+			require.NoError(t, err)
+
+			// Check readiness - should be false because dependency is not satisfied
+			ready, err := client.SyncReady(ctx, "test-unit")
+			require.NoError(t, err)
+			require.False(t, ready)
+		})
+
+		t.Run("UnitReady", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+			ctx := testutil.Context(t, testutil.WaitShort)
+			server, err := agentsocket.NewServer(
+				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(ctx, t, socketPath)
+
+			// Register a unit with no dependencies - should be ready immediately
+			err = client.SyncStart(ctx, "test-unit")
+			require.NoError(t, err)
+
+			// Check readiness - should be true
+			ready, err := client.SyncReady(ctx, "test-unit")
+			require.NoError(t, err)
+			require.True(t, ready)
+
+			// Also test a unit with satisfied dependencies
+			err = client.SyncWant(ctx, "dependent-unit", "test-unit")
+			require.NoError(t, err)
+
+			// Complete the dependency
+			err = client.SyncComplete(ctx, "test-unit")
+			require.NoError(t, err)
+
+			// Now dependent-unit should be ready
+			ready, err = client.SyncReady(ctx, "dependent-unit")
+			require.NoError(t, err)
+			require.True(t, ready)
+		})
+	})
+}
@@ -0,0 +1,73 @@
+//go:build !windows
+
+package agentsocket
+
+import (
+	"context"
+	"net"
+	"os"
+	"path/filepath"
+	"time"
+
+	"golang.org/x/xerrors"
+)
+
+const defaultSocketPath = "/tmp/coder-agent.sock"
+
+func createSocket(path string) (net.Listener, error) {
+	if path == "" {
+		path = defaultSocketPath
+	}
+
+	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)
+	}
+
+	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
+}
+
+func cleanupSocket(path string) error {
+	return os.Remove(path)
+}
+
+func isSocketAvailable(path string) bool {
+	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 {
+		return true
+	}
+	_ = conn.Close()
+	return false
+}
+
+func dialSocket(ctx context.Context, path string) (net.Conn, error) {
+	if path == "" {
+		path = defaultSocketPath
+	}
+
+	dialer := net.Dialer{}
+	return dialer.DialContext(ctx, "unix", path)
+}
@@ -0,0 +1,22 @@
+//go:build windows
+
+package agentsocket
+
+import (
+	"context"
+	"net"
+
+	"golang.org/x/xerrors"
+)
+
+func createSocket(_ string) (net.Listener, error) {
+	return nil, xerrors.New("agentsocket is not supported on Windows")
+}
+
+func cleanupSocket(_ string) error {
+	return nil
+}
+
+func dialSocket(_ context.Context, _ string) (net.Conn, error) {
+	return nil, xerrors.New("agentsocket is not supported on Windows")
+}
@@ -2,41 +2,31 @@ package agent

 import (
 	"net/http"
-	"sync"
-	"time"

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

 	"github.com/coder/coder/v2/coderd/httpapi"
+	"github.com/coder/coder/v2/coderd/httpmw/loggermw"
+	"github.com/coder/coder/v2/coderd/tracing"
 	"github.com/coder/coder/v2/codersdk"
+	"github.com/coder/coder/v2/codersdk/workspacesdk"
+	"github.com/coder/coder/v2/httpmw"
 )

 func (a *agent) apiHandler() http.Handler {
 	r := chi.NewRouter()
+	r.Use(
+		httpmw.Recover(a.logger),
+		tracing.StatusWriterMiddleware,
+		loggermw.Logger(a.logger),
+	)
 	r.Get("/", func(rw http.ResponseWriter, r *http.Request) {
 		httpapi.Write(r.Context(), rw, http.StatusOK, codersdk.Response{
 			Message: "Hello from the agent!",
 		})
 	})

-	// Make a copy to ensure the map is not modified after the handler is
-	// created.
-	cpy := make(map[int]string)
-	for k, b := range a.ignorePorts {
-		cpy[k] = b
-	}
-
-	cacheDuration := 1 * time.Second
-	if a.portCacheDuration > 0 {
-		cacheDuration = a.portCacheDuration
-	}
-
-	lp := &listeningPortsHandler{
-		ignorePorts:   cpy,
-		cacheDuration: cacheDuration,
-	}
-
 	if a.devcontainers {
 		r.Mount("/api/v0/containers", a.containerAPI.Routes())
 	} else if manifest := a.manifest.Load(); manifest != nil && manifest.ParentID != uuid.Nil {
@@ -57,7 +47,7 @@ func (a *agent) apiHandler() http.Handler {

 	promHandler := PrometheusMetricsHandler(a.prometheusRegistry, a.logger)

-	r.Get("/api/v0/listening-ports", lp.handler)
+	r.Get("/api/v0/listening-ports", a.listeningPortsHandler.handler)
 	r.Get("/api/v0/netcheck", a.HandleNetcheck)
 	r.Post("/api/v0/list-directory", a.HandleLS)
 	r.Get("/api/v0/read-file", a.HandleReadFile)
@@ -72,22 +62,21 @@ func (a *agent) apiHandler() http.Handler {
 	return r
 }

-type listeningPortsHandler struct {
-	ignorePorts   map[int]string
-	cacheDuration time.Duration
+type ListeningPortsGetter interface {
+	GetListeningPorts() ([]codersdk.WorkspaceAgentListeningPort, error)
+}

-	//nolint: unused  // used on some but not all platforms
-	mut sync.Mutex
-	//nolint: unused  // used on some but not all platforms
-	ports []codersdk.WorkspaceAgentListeningPort
-	//nolint: unused  // used on some but not all platforms
-	mtime time.Time
+type listeningPortsHandler struct {
+	// In production code, this is set to an osListeningPortsGetter, but it can be overridden for
+	// testing.
+	getter      ListeningPortsGetter
+	ignorePorts map[int]string
 }

 // handler returns a list of listening ports. This is tested by coderd's
 // TestWorkspaceAgentListeningPorts test.
 func (lp *listeningPortsHandler) handler(rw http.ResponseWriter, r *http.Request) {
-	ports, err := lp.getListeningPorts()
+	ports, err := lp.getter.GetListeningPorts()
 	if err != nil {
 		httpapi.Write(r.Context(), rw, http.StatusInternalServerError, codersdk.Response{
 			Message: "Could not scan for listening ports.",
@@ -96,7 +85,20 @@ func (lp *listeningPortsHandler) handler(rw http.ResponseWriter, r *http.Request
 		return
 	}

+	filteredPorts := make([]codersdk.WorkspaceAgentListeningPort, 0, len(ports))
+	for _, port := range ports {
+		if port.Port < workspacesdk.AgentMinimumListeningPort {
+			continue
+		}
+
+		// Ignore ports that we've been told to ignore.
+		if _, ok := lp.ignorePorts[int(port.Port)]; ok {
+			continue
+		}
+		filteredPorts = append(filteredPorts, port)
+	}
+
 	httpapi.Write(r.Context(), rw, http.StatusOK, codersdk.WorkspaceAgentListeningPortsResponse{
-		Ports: ports,
+		Ports: filteredPorts,
 	})
 }
@@ -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
 	}
@@ -3,16 +3,23 @@
 package agent

 import (
+	"sync"
 	"time"

 	"github.com/cakturk/go-netstat/netstat"
 	"golang.org/x/xerrors"

 	"github.com/coder/coder/v2/codersdk"
-	"github.com/coder/coder/v2/codersdk/workspacesdk"
 )

-func (lp *listeningPortsHandler) getListeningPorts() ([]codersdk.WorkspaceAgentListeningPort, error) {
+type osListeningPortsGetter struct {
+	cacheDuration time.Duration
+	mut           sync.Mutex
+	ports         []codersdk.WorkspaceAgentListeningPort
+	mtime         time.Time
+}
+
+func (lp *osListeningPortsGetter) GetListeningPorts() ([]codersdk.WorkspaceAgentListeningPort, error) {
 	lp.mut.Lock()
 	defer lp.mut.Unlock()

@@ -33,12 +40,7 @@ func (lp *listeningPortsHandler) getListeningPorts() ([]codersdk.WorkspaceAgentL
 	seen := make(map[uint16]struct{}, len(tabs))
 	ports := []codersdk.WorkspaceAgentListeningPort{}
 	for _, tab := range tabs {
-		if tab.LocalAddr == nil || tab.LocalAddr.Port < workspacesdk.AgentMinimumListeningPort {
-			continue
-		}
-
-		// Ignore ports that we've been told to ignore.
-		if _, ok := lp.ignorePorts[int(tab.LocalAddr.Port)]; ok {
+		if tab.LocalAddr == nil {
 			continue
 		}

@@ -0,0 +1,45 @@
+//go:build linux || (windows && amd64)
+
+package agent
+
+import (
+	"net"
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestOSListeningPortsGetter(t *testing.T) {
+	t.Parallel()
+
+	uut := &osListeningPortsGetter{
+		cacheDuration: 1 * time.Hour,
+	}
+
+	l, err := net.Listen("tcp", "localhost:0")
+	require.NoError(t, err)
+	defer l.Close()
+
+	ports, err := uut.GetListeningPorts()
+	require.NoError(t, err)
+	found := false
+	for _, port := range ports {
+		// #nosec G115 - Safe conversion as TCP port numbers are within uint16 range (0-65535)
+		if port.Port == uint16(l.Addr().(*net.TCPAddr).Port) {
+			found = true
+			break
+		}
+	}
+	require.True(t, found)
+
+	// check that we cache the ports
+	err = l.Close()
+	require.NoError(t, err)
+	portsNew, err := uut.GetListeningPorts()
+	require.NoError(t, err)
+	require.Equal(t, ports, portsNew)
+
+	// note that it's unsafe to try to assert that a port does not exist in the response
+	// because the OS may reallocate the port very quickly.
+}
@@ -2,9 +2,17 @@

 package agent

-import "github.com/coder/coder/v2/codersdk"
+import (
+	"time"

-func (*listeningPortsHandler) getListeningPorts() ([]codersdk.WorkspaceAgentListeningPort, error) {
+	"github.com/coder/coder/v2/codersdk"
+)
+
+type osListeningPortsGetter struct {
+	cacheDuration time.Duration
+}
+
+func (*osListeningPortsGetter) GetListeningPorts() ([]codersdk.WorkspaceAgentListeningPort, error) {
 	// Can't scan for ports on non-linux or non-windows_amd64 systems at the
 	// moment. The UI will not show any "no ports found" message to the user, so
 	// the user won't suspect a thing.
@@ -0,0 +1,174 @@
+package unit
+
+import (
+	"fmt"
+	"sync"
+
+	"golang.org/x/xerrors"
+	"gonum.org/v1/gonum/graph/encoding/dot"
+	"gonum.org/v1/gonum/graph/simple"
+	"gonum.org/v1/gonum/graph/topo"
+)
+
+// Graph provides a bidirectional interface over gonum's directed graph implementation.
+// While the underlying gonum graph is directed, we overlay bidirectional semantics
+// by distinguishing between forward and reverse edges. Wanting and being wanted by
+// other units are related but different concepts that have different graph traversal
+// implications when Units update their status.
+//
+// The graph stores edge types to represent different relationships between units,
+// allowing for domain-specific semantics beyond simple connectivity.
+type Graph[EdgeType, VertexType comparable] struct {
+	mu sync.RWMutex
+	// The underlying gonum graph. It stores vertices and edges without knowing about the types of the vertices and edges.
+	gonumGraph *simple.DirectedGraph
+	// Maps vertices to their IDs so that a gonum vertex ID can be used to lookup the vertex type.
+	vertexToID map[VertexType]int64
+	// Maps vertex IDs to their types so that a vertex type can be used to lookup the gonum vertex ID.
+	idToVertex map[int64]VertexType
+	// The next ID to assign to a vertex.
+	nextID int64
+	// Store edge types by "fromID->toID" key. This is used to lookup the edge type for a given edge.
+	edgeTypes map[string]EdgeType
+}
+
+// Edge is a convenience type for representing an edge in the graph.
+// It encapsulates the from and to vertices and the edge type itself.
+type Edge[EdgeType, VertexType comparable] struct {
+	From VertexType
+	To   VertexType
+	Edge EdgeType
+}
+
+// AddEdge adds an edge to the graph. It initializes the graph and metadata on first use,
+// checks for cycles, and adds the edge to the gonum graph.
+func (g *Graph[EdgeType, VertexType]) AddEdge(from, to VertexType, edge EdgeType) error {
+	g.mu.Lock()
+	defer g.mu.Unlock()
+
+	if g.gonumGraph == nil {
+		g.gonumGraph = simple.NewDirectedGraph()
+		g.vertexToID = make(map[VertexType]int64)
+		g.idToVertex = make(map[int64]VertexType)
+		g.edgeTypes = make(map[string]EdgeType)
+		g.nextID = 1
+	}
+
+	fromID := g.getOrCreateVertexID(from)
+	toID := g.getOrCreateVertexID(to)
+
+	if g.canReach(to, from) {
+		return xerrors.Errorf("adding edge (%v -> %v): %w", from, to, ErrCycleDetected)
+	}
+
+	g.gonumGraph.SetEdge(simple.Edge{F: simple.Node(fromID), T: simple.Node(toID)})
+
+	edgeKey := fmt.Sprintf("%d->%d", fromID, toID)
+	g.edgeTypes[edgeKey] = edge
+
+	return nil
+}
+
+// GetForwardAdjacentVertices returns all the edges that originate from the given vertex.
+func (g *Graph[EdgeType, VertexType]) GetForwardAdjacentVertices(from VertexType) []Edge[EdgeType, VertexType] {
+	g.mu.RLock()
+	defer g.mu.RUnlock()
+
+	fromID, exists := g.vertexToID[from]
+	if !exists {
+		return []Edge[EdgeType, VertexType]{}
+	}
+
+	edges := []Edge[EdgeType, VertexType]{}
+	toNodes := g.gonumGraph.From(fromID)
+	for toNodes.Next() {
+		toID := toNodes.Node().ID()
+		to := g.idToVertex[toID]
+
+		// Get the edge type
+		edgeKey := fmt.Sprintf("%d->%d", fromID, toID)
+		edgeType := g.edgeTypes[edgeKey]
+
+		edges = append(edges, Edge[EdgeType, VertexType]{From: from, To: to, Edge: edgeType})
+	}
+
+	return edges
+}
+
+// GetReverseAdjacentVertices returns all the edges that terminate at the given vertex.
+func (g *Graph[EdgeType, VertexType]) GetReverseAdjacentVertices(to VertexType) []Edge[EdgeType, VertexType] {
+	g.mu.RLock()
+	defer g.mu.RUnlock()
+
+	toID, exists := g.vertexToID[to]
+	if !exists {
+		return []Edge[EdgeType, VertexType]{}
+	}
+
+	edges := []Edge[EdgeType, VertexType]{}
+	fromNodes := g.gonumGraph.To(toID)
+	for fromNodes.Next() {
+		fromID := fromNodes.Node().ID()
+		from := g.idToVertex[fromID]
+
+		// Get the edge type
+		edgeKey := fmt.Sprintf("%d->%d", fromID, toID)
+		edgeType := g.edgeTypes[edgeKey]
+
+		edges = append(edges, Edge[EdgeType, VertexType]{From: from, To: to, Edge: edgeType})
+	}
+
+	return edges
+}
+
+// getOrCreateVertexID returns the ID for a vertex, creating it if it doesn't exist.
+func (g *Graph[EdgeType, VertexType]) getOrCreateVertexID(vertex VertexType) int64 {
+	if id, exists := g.vertexToID[vertex]; exists {
+		return id
+	}
+
+	id := g.nextID
+	g.nextID++
+	g.vertexToID[vertex] = id
+	g.idToVertex[id] = vertex
+
+	// Add the node to the gonum graph
+	g.gonumGraph.AddNode(simple.Node(id))
+
+	return id
+}
+
+// canReach checks if there is a path from the start vertex to the end vertex.
+func (g *Graph[EdgeType, VertexType]) canReach(start, end VertexType) bool {
+	if start == end {
+		return true
+	}
+
+	startID, startExists := g.vertexToID[start]
+	endID, endExists := g.vertexToID[end]
+
+	if !startExists || !endExists {
+		return false
+	}
+
+	// Use gonum's built-in path existence check
+	return topo.PathExistsIn(g.gonumGraph, simple.Node(startID), simple.Node(endID))
+}
+
+// ToDOT exports the graph to DOT format for visualization
+func (g *Graph[EdgeType, VertexType]) ToDOT(name string) (string, error) {
+	g.mu.RLock()
+	defer g.mu.RUnlock()
+
+	if g.gonumGraph == nil {
+		return "", xerrors.New("graph is not initialized")
+	}
+
+	// Marshal the graph to DOT format
+	dotBytes, err := dot.Marshal(g.gonumGraph, name, "", "  ")
+	if err != nil {
+		return "", xerrors.Errorf("failed to marshal graph to DOT: %w", err)
+	}
+
+	return string(dotBytes), nil
+}
@@ -0,0 +1,452 @@
+// Package unit_test provides tests for the unit package.
+//
+// DOT Graph Testing:
+// The graph tests use golden files for DOT representation verification.
+// To update the golden files:
+// make gen/golden-files
+//
+// The golden files contain the expected DOT representation and can be easily
+// inspected, version controlled, and updated when the graph structure changes.
+package unit_test
+
+import (
+	"bytes"
+	"flag"
+	"fmt"
+	"os"
+	"path/filepath"
+	"sync"
+	"testing"
+
+	"github.com/google/go-cmp/cmp"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/agent/unit"
+	"github.com/coder/coder/v2/cryptorand"
+)
+
+type testGraphEdge string
+
+const (
+	testEdgeStarted   testGraphEdge = "started"
+	testEdgeCompleted testGraphEdge = "completed"
+)
+
+type testGraphVertex struct {
+	Name string
+}
+
+type (
+	testGraph = unit.Graph[testGraphEdge, *testGraphVertex]
+	testEdge  = unit.Edge[testGraphEdge, *testGraphVertex]
+)
+
+// randInt generates a random integer in the range [0, limit).
+func randInt(limit int) int {
+	if limit <= 0 {
+		return 0
+	}
+	n, err := cryptorand.Int63n(int64(limit))
+	if err != nil {
+		return 0
+	}
+	return int(n)
+}
+
+// UpdateGoldenFiles indicates golden files should be updated.
+// To update the golden files:
+// make gen/golden-files
+var UpdateGoldenFiles = flag.Bool("update", false, "update .golden files")
+
+// assertDOTGraph requires that the graph's DOT representation matches the golden file
+func assertDOTGraph(t *testing.T, graph *testGraph, goldenName string) {
+	t.Helper()
+
+	dot, err := graph.ToDOT(goldenName)
+	require.NoError(t, err)
+
+	goldenFile := filepath.Join("testdata", goldenName+".golden")
+	if *UpdateGoldenFiles {
+		t.Logf("update golden file for: %q: %s", goldenName, goldenFile)
+		err := os.MkdirAll(filepath.Dir(goldenFile), 0o755)
+		require.NoError(t, err, "want no error creating golden file directory")
+		err = os.WriteFile(goldenFile, []byte(dot), 0o600)
+		require.NoError(t, err, "update golden file")
+	}
+
+	expected, err := os.ReadFile(goldenFile)
+	require.NoError(t, err, "read golden file, run \"make gen/golden-files\" and commit the changes")
+
+	// Normalize line endings for cross-platform compatibility
+	expected = normalizeLineEndings(expected)
+	normalizedDot := normalizeLineEndings([]byte(dot))
+
+	assert.Empty(t, cmp.Diff(string(expected), string(normalizedDot)), "golden file mismatch (-want +got): %s, run \"make gen/golden-files\", verify and commit the changes", goldenFile)
+}
+
+// normalizeLineEndings ensures that all line endings are normalized to \n.
+// Required for Windows compatibility.
+func normalizeLineEndings(content []byte) []byte {
+	content = bytes.ReplaceAll(content, []byte("\r\n"), []byte("\n"))
+	content = bytes.ReplaceAll(content, []byte("\r"), []byte("\n"))
+	return content
+}
+
+func TestGraph(t *testing.T) {
+	t.Parallel()
+
+	testFuncs := map[string]func(t *testing.T) *unit.Graph[testGraphEdge, *testGraphVertex]{
+		"ForwardAndReverseEdges": func(t *testing.T) *unit.Graph[testGraphEdge, *testGraphVertex] {
+			graph := &unit.Graph[testGraphEdge, *testGraphVertex]{}
+			unit1 := &testGraphVertex{Name: "unit1"}
+			unit2 := &testGraphVertex{Name: "unit2"}
+			unit3 := &testGraphVertex{Name: "unit3"}
+			err := graph.AddEdge(unit1, unit2, testEdgeCompleted)
+			require.NoError(t, err)
+			err = graph.AddEdge(unit1, unit3, testEdgeStarted)
+			require.NoError(t, err)
+
+			// Check for forward edge
+			vertices := graph.GetForwardAdjacentVertices(unit1)
+			require.Len(t, vertices, 2)
+			// Unit 1 depends on the completion of Unit2
+			require.Contains(t, vertices, testEdge{
+				From: unit1,
+				To:   unit2,
+				Edge: testEdgeCompleted,
+			})
+			// Unit 1 depends on the start of Unit3
+			require.Contains(t, vertices, testEdge{
+				From: unit1,
+				To:   unit3,
+				Edge: testEdgeStarted,
+			})
+
+			// Check for reverse edges
+			unit2ReverseEdges := graph.GetReverseAdjacentVertices(unit2)
+			require.Len(t, unit2ReverseEdges, 1)
+			// Unit 2 must be completed before Unit 1 can start
+			require.Contains(t, unit2ReverseEdges, testEdge{
+				From: unit1,
+				To:   unit2,
+				Edge: testEdgeCompleted,
+			})
+
+			unit3ReverseEdges := graph.GetReverseAdjacentVertices(unit3)
+			require.Len(t, unit3ReverseEdges, 1)
+			// Unit 3 must be started before Unit 1 can complete
+			require.Contains(t, unit3ReverseEdges, testEdge{
+				From: unit1,
+				To:   unit3,
+				Edge: testEdgeStarted,
+			})
+
+			return graph
+		},
+		"SelfReference": func(t *testing.T) *testGraph {
+			graph := &testGraph{}
+			unit1 := &testGraphVertex{Name: "unit1"}
+			err := graph.AddEdge(unit1, unit1, testEdgeCompleted)
+			require.ErrorIs(t, err, unit.ErrCycleDetected)
+
+			return graph
+		},
+		"Cycle": func(t *testing.T) *testGraph {
+			graph := &testGraph{}
+			unit1 := &testGraphVertex{Name: "unit1"}
+			unit2 := &testGraphVertex{Name: "unit2"}
+			err := graph.AddEdge(unit1, unit2, testEdgeCompleted)
+			require.NoError(t, err)
+			err = graph.AddEdge(unit2, unit1, testEdgeStarted)
+			require.ErrorIs(t, err, unit.ErrCycleDetected)
+
+			return graph
+		},
+		"MultipleDependenciesSameStatus": func(t *testing.T) *testGraph {
+			graph := &testGraph{}
+			unit1 := &testGraphVertex{Name: "unit1"}
+			unit2 := &testGraphVertex{Name: "unit2"}
+			unit3 := &testGraphVertex{Name: "unit3"}
+			unit4 := &testGraphVertex{Name: "unit4"}
+
+			// Unit1 depends on completion of both unit2 and unit3 (same status type)
+			err := graph.AddEdge(unit1, unit2, testEdgeCompleted)
+			require.NoError(t, err)
+			err = graph.AddEdge(unit1, unit3, testEdgeCompleted)
+			require.NoError(t, err)
+
+			// Unit1 also depends on starting of unit4 (different status type)
+			err = graph.AddEdge(unit1, unit4, testEdgeStarted)
+			require.NoError(t, err)
+
+			// Check that unit1 has 3 forward dependencies
+			forwardEdges := graph.GetForwardAdjacentVertices(unit1)
+			require.Len(t, forwardEdges, 3)
+
+			// Verify all expected dependencies exist
+			expectedDependencies := []testEdge{
+				{From: unit1, To: unit2, Edge: testEdgeCompleted},
+				{From: unit1, To: unit3, Edge: testEdgeCompleted},
+				{From: unit1, To: unit4, Edge: testEdgeStarted},
+			}
+
+			for _, expected := range expectedDependencies {
+				require.Contains(t, forwardEdges, expected)
+			}
+
+			// Check reverse dependencies
+			unit2ReverseEdges := graph.GetReverseAdjacentVertices(unit2)
+			require.Len(t, unit2ReverseEdges, 1)
+			require.Contains(t, unit2ReverseEdges, testEdge{
+				From: unit1, To: unit2, Edge: testEdgeCompleted,
+			})
+
+			unit3ReverseEdges := graph.GetReverseAdjacentVertices(unit3)
+			require.Len(t, unit3ReverseEdges, 1)
+			require.Contains(t, unit3ReverseEdges, testEdge{
+				From: unit1, To: unit3, Edge: testEdgeCompleted,
+			})
+
+			unit4ReverseEdges := graph.GetReverseAdjacentVertices(unit4)
+			require.Len(t, unit4ReverseEdges, 1)
+			require.Contains(t, unit4ReverseEdges, testEdge{
+				From: unit1, To: unit4, Edge: testEdgeStarted,
+			})
+
+			return graph
+		},
+	}
+
+	for testName, testFunc := range testFuncs {
+		var graph *testGraph
+		t.Run(testName, func(t *testing.T) {
+			t.Parallel()
+			graph = testFunc(t)
+			assertDOTGraph(t, graph, testName)
+		})
+	}
+}
+
+func TestGraphThreadSafety(t *testing.T) {
+	t.Parallel()
+
+	t.Run("ConcurrentReadWrite", func(t *testing.T) {
+		t.Parallel()
+
+		graph := &testGraph{}
+		var wg sync.WaitGroup
+		const numWriters = 50
+		const numReaders = 100
+		const operationsPerWriter = 1000
+		const operationsPerReader = 2000
+
+		barrier := make(chan struct{})
+		// Launch writers
+		for i := 0; i < numWriters; i++ {
+			wg.Add(1)
+			go func(writerID int) {
+				defer wg.Done()
+				<-barrier
+				for j := 0; j < operationsPerWriter; j++ {
+					from := &testGraphVertex{Name: fmt.Sprintf("writer-%d-%d", writerID, j)}
+					to := &testGraphVertex{Name: fmt.Sprintf("writer-%d-%d", writerID, j+1)}
+					graph.AddEdge(from, to, testEdgeCompleted)
+				}
+			}(i)
+		}
+
+		// Launch readers
+		readerResults := make([]struct {
+			panicked  bool
+			readCount int
+		}, numReaders)
+
+		for i := 0; i < numReaders; i++ {
+			wg.Add(1)
+			go func(readerID int) {
+				defer wg.Done()
+				<-barrier
+				defer func() {
+					if r := recover(); r != nil {
+						readerResults[readerID].panicked = true
+					}
+				}()
+
+				readCount := 0
+				for j := 0; j < operationsPerReader; j++ {
+					// Create a test vertex and read
+					testUnit := &testGraphVertex{Name: fmt.Sprintf("test-reader-%d-%d", readerID, j)}
+					forwardEdges := graph.GetForwardAdjacentVertices(testUnit)
+					reverseEdges := graph.GetReverseAdjacentVertices(testUnit)
+
+					// Just verify no panics (results may be nil for non-existent vertices)
+					_ = forwardEdges
+					_ = reverseEdges
+					readCount++
+				}
+				readerResults[readerID].readCount = readCount
+			}(i)
+		}
+
+		close(barrier)
+		wg.Wait()
+
+		// Verify no panics occurred in readers
+		for i, result := range readerResults {
+			require.False(t, result.panicked, "reader %d panicked", i)
+			require.Equal(t, operationsPerReader, result.readCount, "reader %d should have performed expected reads", i)
+		}
+	})
+
+	t.Run("ConcurrentCycleDetection", func(t *testing.T) {
+		t.Parallel()
+
+		graph := &testGraph{}
+
+		// Pre-create chain: A→B→C→D
+		unitA := &testGraphVertex{Name: "A"}
+		unitB := &testGraphVertex{Name: "B"}
+		unitC := &testGraphVertex{Name: "C"}
+		unitD := &testGraphVertex{Name: "D"}
+
+		err := graph.AddEdge(unitA, unitB, testEdgeCompleted)
+		require.NoError(t, err)
+		err = graph.AddEdge(unitB, unitC, testEdgeCompleted)
+		require.NoError(t, err)
+		err = graph.AddEdge(unitC, unitD, testEdgeCompleted)
+		require.NoError(t, err)
+
+		barrier := make(chan struct{})
+		var wg sync.WaitGroup
+		const numGoroutines = 50
+		cycleErrors := make([]error, numGoroutines)
+
+		// Launch goroutines trying to add D→A (creates cycle)
+		for i := 0; i < numGoroutines; i++ {
+			wg.Add(1)
+			go func(goroutineID int) {
+				defer wg.Done()
+				<-barrier
+				err := graph.AddEdge(unitD, unitA, testEdgeCompleted)
+				cycleErrors[goroutineID] = err
+			}(i)
+		}
+
+		close(barrier)
+		wg.Wait()
+
+		// Verify all attempts correctly returned cycle error
+		for i, err := range cycleErrors {
+			require.Error(t, err, "goroutine %d should have detected cycle", i)
+			require.ErrorIs(t, err, unit.ErrCycleDetected)
+		}
+
+		// Verify graph remains valid (original chain intact)
+		dot, err := graph.ToDOT("test")
+		require.NoError(t, err)
+		require.NotEmpty(t, dot)
+	})
+
+	t.Run("ConcurrentToDOT", func(t *testing.T) {
+		t.Parallel()
+
+		graph := &testGraph{}
+
+		// Pre-populate graph
+		for i := 0; i < 20; i++ {
+			from := &testGraphVertex{Name: fmt.Sprintf("dot-unit-%d", i)}
+			to := &testGraphVertex{Name: fmt.Sprintf("dot-unit-%d", i+1)}
+			err := graph.AddEdge(from, to, testEdgeCompleted)
+			require.NoError(t, err)
+		}
+
+		barrier := make(chan struct{})
+		var wg sync.WaitGroup
+		const numReaders = 100
+		const numWriters = 20
+		dotResults := make([]string, numReaders)
+
+		// Launch readers calling ToDOT
+		dotErrors := make([]error, numReaders)
+		for i := 0; i < numReaders; i++ {
+			wg.Add(1)
+			go func(readerID int) {
+				defer wg.Done()
+				<-barrier
+				dot, err := graph.ToDOT(fmt.Sprintf("test-%d", readerID))
+				dotErrors[readerID] = err
+				if err == nil {
+					dotResults[readerID] = dot
+				}
+			}(i)
+		}
+
+		// Launch writers adding edges
+		for i := 0; i < numWriters; i++ {
+			wg.Add(1)
+			go func(writerID int) {
+				defer wg.Done()
+				<-barrier
+				from := &testGraphVertex{Name: fmt.Sprintf("writer-dot-%d", writerID)}
+				to := &testGraphVertex{Name: fmt.Sprintf("writer-dot-target-%d", writerID)}
+				graph.AddEdge(from, to, testEdgeCompleted)
+			}(i)
+		}
+
+		close(barrier)
+		wg.Wait()
+
+		// Verify no errors occurred during DOT generation
+		for i, err := range dotErrors {
+			require.NoError(t, err, "DOT generation error at index %d", i)
+		}
+
+		// Verify all DOT results are valid
+		for i, dot := range dotResults {
+			require.NotEmpty(t, dot, "DOT result %d should not be empty", i)
+		}
+	})
+}
+
+func BenchmarkGraph_ConcurrentMixedOperations(b *testing.B) {
+	graph := &testGraph{}
+	var wg sync.WaitGroup
+	const numGoroutines = 200
+
+	b.ResetTimer()
+	for i := 0; i < b.N; i++ {
+		// Launch goroutines performing random operations
+		for j := 0; j < numGoroutines; j++ {
+			wg.Add(1)
+			go func(goroutineID int) {
+				defer wg.Done()
+				operationCount := 0
+
+				for operationCount < 50 {
+					operation := float32(randInt(100)) / 100.0
+
+					if operation < 0.6 { // 60% reads
+						// Read operation
+						testUnit := &testGraphVertex{Name: fmt.Sprintf("bench-read-%d-%d", goroutineID, operationCount)}
+						forwardEdges := graph.GetForwardAdjacentVertices(testUnit)
+						reverseEdges := graph.GetReverseAdjacentVertices(testUnit)
+
+						// Just verify no panics (results may be nil for non-existent vertices)
+						_ = forwardEdges
+						_ = reverseEdges
+					} else { // 40% writes
+						// Write operation
+						from := &testGraphVertex{Name: fmt.Sprintf("bench-write-%d-%d", goroutineID, operationCount)}
+						to := &testGraphVertex{Name: fmt.Sprintf("bench-write-target-%d-%d", goroutineID, operationCount)}
+						graph.AddEdge(from, to, testEdgeCompleted)
+					}
+
+					operationCount++
+				}
+			}(j)
+		}
+
+		wg.Wait()
+	}
+}
@@ -0,0 +1,290 @@
+package unit
+
+import (
+	"errors"
+	"fmt"
+	"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
+
+var _ fmt.Stringer = Status("")
+
+func (s Status) String() string {
+	if s == StatusNotRegistered {
+		return "not registered"
+	}
+	return string(s)
+}
+
+// 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 true, 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)
+}
@@ -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.True(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")
+	})
+}
@@ -0,0 +1,8 @@
+strict digraph Cycle {
+  // Node definitions.
+  1;
+  2;
+
+  // Edge definitions.
+  1 -> 2;
+}
@@ -0,0 +1,10 @@
+strict digraph ForwardAndReverseEdges {
+  // Node definitions.
+  1;
+  2;
+  3;
+
+  // Edge definitions.
+  1 -> 2;
+  1 -> 3;
+}
@@ -0,0 +1,12 @@
+strict digraph MultipleDependenciesSameStatus {
+  // Node definitions.
+  1;
+  2;
+  3;
+  4;
+
+  // Edge definitions.
+  1 -> 2;
+  1 -> 3;
+  1 -> 4;
+}
@@ -0,0 +1,4 @@
+strict digraph SelfReference {
+  // Node definitions.
+  1;
+}
@@ -11,6 +11,7 @@ import (
 	"os"
 	"path/filepath"
 	"runtime"
+	"slices"
 	"strconv"
 	"strings"
 	"time"
@@ -56,6 +57,8 @@ func workspaceAgent() *serpent.Command {
 		devcontainers                  bool
 		devcontainerProjectDiscovery   bool
 		devcontainerDiscoveryAutostart bool
+		socketServerEnabled            bool
+		socketPath                     string
 	)
 	agentAuth := &AgentAuth{}
 	cmd := &serpent.Command{
@@ -201,18 +204,15 @@ 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 +276,28 @@ 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,
@@ -297,12 +319,19 @@ func workspaceAgent() *serpent.Command {
 						agentcontainers.WithProjectDiscovery(devcontainerProjectDiscovery),
 						agentcontainers.WithDiscoveryAutostart(devcontainerDiscoveryAutostart),
 					},
+					SocketPath:          socketPath,
+					SocketServerEnabled: socketServerEnabled,
 				})

-				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 +343,11 @@ func workspaceAgent() *serpent.Command {
 				}

 				lastErr = agnt.Close()
-				debugSrvClose()
-				prometheusSrvClose()
+
+				slices.Reverse(serverClose)
+				for _, closeFunc := range serverClose {
+					closeFunc()
+				}

 				if mustExit {
 					break
@@ -449,6 +481,19 @@ func workspaceAgent() *serpent.Command {
 			Description: "Allow the agent to autostart devcontainer projects it discovers based on their configuration.",
 			Value:       serpent.BoolOf(&devcontainerDiscoveryAutostart),
 		},
+		{
+			Flag:        "socket-server-enabled",
+			Default:     "false",
+			Env:         "CODER_AGENT_SOCKET_SERVER_ENABLED",
+			Description: "Enable the agent socket server.",
+			Value:       serpent.BoolOf(&socketServerEnabled),
+		},
+		{
+			Flag:        "socket-path",
+			Env:         "CODER_AGENT_SOCKET_PATH",
+			Description: "Specify the path for the agent socket.",
+			Value:       serpent.StringOf(&socketPath),
+		},
 	}
 	agentAuth.AttachOptions(cmd, false)
 	return cmd
@@ -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 {
@@ -0,0 +1,78 @@
+package cli
+
+import (
+	"encoding/csv"
+	"strings"
+
+	"github.com/spf13/pflag"
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/codersdk"
+)
+
+var (
+	_ pflag.SliceValue = &AllowListFlag{}
+	_ pflag.Value      = &AllowListFlag{}
+)
+
+// AllowListFlag implements pflag.SliceValue for codersdk.APIAllowListTarget entries.
+type AllowListFlag []codersdk.APIAllowListTarget
+
+func AllowListFlagOf(al *[]codersdk.APIAllowListTarget) *AllowListFlag {
+	return (*AllowListFlag)(al)
+}
+
+func (a AllowListFlag) String() string {
+	return strings.Join(a.GetSlice(), ",")
+}
+
+func (a AllowListFlag) Value() []codersdk.APIAllowListTarget {
+	return []codersdk.APIAllowListTarget(a)
+}
+
+func (AllowListFlag) Type() string { return "allow-list" }
+
+func (a *AllowListFlag) Set(set string) error {
+	values, err := csv.NewReader(strings.NewReader(set)).Read()
+	if err != nil {
+		return xerrors.Errorf("parse allow list entries as csv: %w", err)
+	}
+	for _, v := range values {
+		if err := a.Append(v); err != nil {
+			return err
+		}
+	}
+	return nil
+}
+
+func (a *AllowListFlag) Append(value string) error {
+	value = strings.TrimSpace(value)
+	if value == "" {
+		return xerrors.New("allow list entry cannot be empty")
+	}
+	var target codersdk.APIAllowListTarget
+	if err := target.UnmarshalText([]byte(value)); err != nil {
+		return err
+	}
+
+	*a = append(*a, target)
+	return nil
+}
+
+func (a *AllowListFlag) Replace(items []string) error {
+	*a = []codersdk.APIAllowListTarget{}
+	for _, item := range items {
+		if err := a.Append(item); err != nil {
+			return err
+		}
+	}
+	return nil
+}
+
+func (a *AllowListFlag) GetSlice() []string {
+	out := make([]string, len(*a))
+	for i, entry := range *a {
+		out[i] = entry.String()
+	}
+	return out
+}
@@ -28,7 +28,9 @@ import (
 )

 // New creates a CLI instance with a configuration pointed to a
-// temporary testing directory.
+// temporary testing directory. The invocation is set up to use a
+// global config directory for the given testing.TB, and keyring
+// usage disabled.
 func New(t testing.TB, args ...string) (*serpent.Invocation, config.Root) {
 	var root cli.RootCmd

@@ -59,6 +61,15 @@ func NewWithCommand(
 	t testing.TB, cmd *serpent.Command, args ...string,
 ) (*serpent.Invocation, config.Root) {
 	configDir := config.Root(t.TempDir())
+	// Keyring usage is disabled here when --global-config is set because many existing
+	// tests expect the session token to be stored on disk and is not properly instrumented
+	// for parallel testing against the actual operating system keyring.
+	invArgs := append([]string{"--global-config", string(configDir)}, args...)
+	return setupInvocation(t, cmd, invArgs...), configDir
+}
+
+func setupInvocation(t testing.TB, cmd *serpent.Command, args ...string,
+) *serpent.Invocation {
 	// I really would like to fail test on error logs, but realistically, turning on by default
 	// in all our CLI tests is going to create a lot of flaky noise.
 	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true}).
@@ -66,16 +77,21 @@ func NewWithCommand(
 		Named("cli")
 	i := &serpent.Invocation{
 		Command: cmd,
-		Args:    append([]string{"--global-config", string(configDir)}, args...),
+		Args:    args,
 		Stdin:   io.LimitReader(nil, 0),
 		Stdout:  (&logWriter{prefix: "stdout", log: logger}),
 		Stderr:  (&logWriter{prefix: "stderr", log: logger}),
 		Logger:  logger,
 	}
 	t.Logf("invoking command: %s %s", cmd.Name(), strings.Join(i.Args, " "))
+	return i
+}

-	// These can be overridden by the test.
-	return i, configDir
+func NewWithDefaultKeyringCommand(t testing.TB, cmd *serpent.Command, args ...string,
+) (*serpent.Invocation, config.Root) {
+	configDir := config.Root(t.TempDir())
+	invArgs := append([]string{"--global-config", string(configDir)}, args...)
+	return setupInvocation(t, cmd, invArgs...), configDir
 }

 // SetupConfig applies the URL and SessionToken of the client to the config.
@@ -53,6 +53,9 @@ func Agent(ctx context.Context, writer io.Writer, agentID uuid.UUID, opts AgentO
 		t := time.NewTimer(0)
 		defer t.Stop()

+		startTime := time.Now()
+		baseInterval := opts.FetchInterval
+
 		for {
 			select {
 			case <-ctx.Done():
@@ -68,7 +71,11 @@ func Agent(ctx context.Context, writer io.Writer, agentID uuid.UUID, opts AgentO
 					return
 				}
 				fetchedAgent <- fetchAgent{agent: agent}
-				t.Reset(opts.FetchInterval)
+
+				// Adjust the interval based on how long we've been waiting.
+				elapsed := time.Since(startTime)
+				currentInterval := GetProgressiveInterval(baseInterval, elapsed)
+				t.Reset(currentInterval)
 			}
 		}
 	}()
@@ -293,6 +300,24 @@ func safeDuration(sw *stageWriter, a, b *time.Time) time.Duration {
 	return a.Sub(*b)
 }

+// GetProgressiveInterval returns an interval that increases over time.
+// The interval starts at baseInterval and increases to
+// a maximum of baseInterval * 16 over time.
+func GetProgressiveInterval(baseInterval time.Duration, elapsed time.Duration) time.Duration {
+	switch {
+	case elapsed < 60*time.Second:
+		return baseInterval // 500ms for first 60 seconds
+	case elapsed < 2*time.Minute:
+		return baseInterval * 2 // 1s for next 1 minute
+	case elapsed < 5*time.Minute:
+		return baseInterval * 4 // 2s for next 3 minutes
+	case elapsed < 10*time.Minute:
+		return baseInterval * 8 // 4s for next 5 minutes
+	default:
+		return baseInterval * 16 // 8s after 10 minutes
+	}
+}
+
 type closeFunc func() error

 func (c closeFunc) Close() error {
@@ -866,3 +866,31 @@ func TestConnDiagnostics(t *testing.T) {
 		})
 	}
 }
+
+func TestGetProgressiveInterval(t *testing.T) {
+	t.Parallel()
+
+	baseInterval := 500 * time.Millisecond
+
+	testCases := []struct {
+		name     string
+		elapsed  time.Duration
+		expected time.Duration
+	}{
+		{"first_minute", 30 * time.Second, baseInterval},
+		{"second_minute", 90 * time.Second, baseInterval * 2},
+		{"third_to_fifth_minute", 3 * time.Minute, baseInterval * 4},
+		{"sixth_to_tenth_minute", 7 * time.Minute, baseInterval * 8},
+		{"after_ten_minutes", 15 * time.Minute, baseInterval * 16},
+		{"boundary_first_minute", 59 * time.Second, baseInterval},
+		{"boundary_second_minute", 61 * time.Second, baseInterval * 2},
+	}
+
+	for _, tc := range testCases {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+			result := cliui.GetProgressiveInterval(baseInterval, tc.elapsed)
+			require.Equal(t, tc.expected, result)
+		})
+	}
+}
@@ -296,22 +296,23 @@ func renderTable(out any, sort string, headers table.Row, filterColumns []string
 // returned. If the table tag is malformed, an error is returned.
 //
 // The returned name is transformed from "snake_case" to "normal text".
-func parseTableStructTag(field reflect.StructField) (name string, defaultSort, noSortOpt, recursive, skipParentName bool, err error) {
+func parseTableStructTag(field reflect.StructField) (name string, defaultSort, noSortOpt, recursive, skipParentName, emptyNil bool, err error) {
 	tags, err := structtag.Parse(string(field.Tag))
 	if err != nil {
-		return "", false, false, false, false, xerrors.Errorf("parse struct field tag %q: %w", string(field.Tag), err)
+		return "", false, false, false, false, false, xerrors.Errorf("parse struct field tag %q: %w", string(field.Tag), err)
 	}

 	tag, err := tags.Get("table")
 	if err != nil || tag.Name == "-" {
 		// tags.Get only returns an error if the tag is not found.
-		return "", false, false, false, false, nil
+		return "", false, false, false, false, false, nil
 	}

 	defaultSortOpt := false
 	noSortOpt = false
 	recursiveOpt := false
 	skipParentNameOpt := false
+	emptyNilOpt := false
 	for _, opt := range tag.Options {
 		switch opt {
 		case "default_sort":
@@ -326,12 +327,14 @@ func parseTableStructTag(field reflect.StructField) (name string, defaultSort, n
 			// make sure the child name is unique across all nested structs in the parent.
 			recursiveOpt = true
 			skipParentNameOpt = true
+		case "empty_nil":
+			emptyNilOpt = true
 		default:
-			return "", false, false, false, false, xerrors.Errorf("unknown option %q in struct field tag", opt)
+			return "", false, false, false, false, false, xerrors.Errorf("unknown option %q in struct field tag", opt)
 		}
 	}

-	return strings.ReplaceAll(tag.Name, "_", " "), defaultSortOpt, noSortOpt, recursiveOpt, skipParentNameOpt, nil
+	return strings.ReplaceAll(tag.Name, "_", " "), defaultSortOpt, noSortOpt, recursiveOpt, skipParentNameOpt, emptyNilOpt, nil
 }

 func isStructOrStructPointer(t reflect.Type) bool {
@@ -358,7 +361,7 @@ func typeToTableHeaders(t reflect.Type, requireDefault bool) ([]string, string,
 	noSortOpt := false
 	for i := 0; i < t.NumField(); i++ {
 		field := t.Field(i)
-		name, defaultSort, noSort, recursive, skip, err := parseTableStructTag(field)
+		name, defaultSort, noSort, recursive, skip, _, err := parseTableStructTag(field)
 		if err != nil {
 			return nil, "", xerrors.Errorf("parse struct tags for field %q in type %q: %w", field.Name, t.String(), err)
 		}
@@ -435,7 +438,7 @@ func valueToTableMap(val reflect.Value) (map[string]any, error) {
 	for i := 0; i < val.NumField(); i++ {
 		field := val.Type().Field(i)
 		fieldVal := val.Field(i)
-		name, _, _, recursive, skip, err := parseTableStructTag(field)
+		name, _, _, recursive, skip, emptyNil, err := parseTableStructTag(field)
 		if err != nil {
 			return nil, xerrors.Errorf("parse struct tags for field %q in type %T: %w", field.Name, val, err)
 		}
@@ -443,8 +446,14 @@ func valueToTableMap(val reflect.Value) (map[string]any, error) {
 			continue
 		}

-		// Recurse if it's a struct.
 		fieldType := field.Type
+
+		// If empty_nil is set and this is a nil pointer, use a zero value.
+		if emptyNil && fieldVal.Kind() == reflect.Pointer && fieldVal.IsNil() {
+			fieldVal = reflect.New(fieldType.Elem())
+		}
+
+		// Recurse if it's a struct.
 		if recursive {
 			if !isStructOrStructPointer(fieldType) {
 				return nil, xerrors.Errorf("field %q in type %q is marked as recursive but does not contain a struct or a pointer to a struct", field.Name, fieldType.String())
@@ -467,7 +476,7 @@ func valueToTableMap(val reflect.Value) (map[string]any, error) {
 		}

 		// Otherwise, we just use the field value.
-		row[name] = val.Field(i).Interface()
+		row[name] = fieldVal.Interface()
 	}

 	return row, nil
@@ -400,6 +400,78 @@ foo   <nil>      10  [a, b, c]  foo1               11  foo2        12         fo
 			})
 		})
 	})
+
+	t.Run("EmptyNil", func(t *testing.T) {
+		t.Parallel()
+
+		type emptyNilTest struct {
+			Name           string  `table:"name,default_sort"`
+			EmptyOnNil     *string `table:"empty_on_nil,empty_nil"`
+			NormalBehavior *string `table:"normal_behavior"`
+		}
+
+		value := "value"
+		in := []emptyNilTest{
+			{
+				Name:           "has_value",
+				EmptyOnNil:     &value,
+				NormalBehavior: &value,
+			},
+			{
+				Name:           "has_nil",
+				EmptyOnNil:     nil,
+				NormalBehavior: nil,
+			},
+		}
+
+		expected := `
+NAME       EMPTY ON NIL  NORMAL BEHAVIOR
+has_nil                  <nil>
+has_value  value         value
+		`
+
+		out, err := cliui.DisplayTable(in, "", nil)
+		log.Println("rendered table:\n" + out)
+		require.NoError(t, err)
+		compareTables(t, expected, out)
+	})
+
+	t.Run("EmptyNilWithRecursiveInline", func(t *testing.T) {
+		t.Parallel()
+
+		type nestedData struct {
+			Name string `table:"name"`
+		}
+
+		type inlineTest struct {
+			Nested *nestedData `table:"ignored,recursive_inline,empty_nil"`
+			Count  int         `table:"count,default_sort"`
+		}
+
+		in := []inlineTest{
+			{
+				Nested: &nestedData{
+					Name: "alice",
+				},
+				Count: 1,
+			},
+			{
+				Nested: nil,
+				Count:  2,
+			},
+		}
+
+		expected := `
+NAME   COUNT
+alice  1
+       2
+		`
+
+		out, err := cliui.DisplayTable(in, "", nil)
+		log.Println("rendered table:\n" + out)
+		require.NoError(t, err)
+		compareTables(t, expected, out)
+	})
 }

 // compareTables normalizes the incoming table lines
@@ -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
@@ -185,9 +185,6 @@ func TestDelete(t *testing.T) {

 	t.Run("WarnNoProvisioners", func(t *testing.T) {
 		t.Parallel()
-		if !dbtestutil.WillUsePostgres() {
-			t.Skip("this test requires postgres")
-		}

 		store, ps, db := dbtestutil.NewDBWithSQLDB(t)
 		client, closeDaemon := coderdtest.NewWithProvisionerCloser(t, &coderdtest.Options{
@@ -228,9 +225,6 @@ func TestDelete(t *testing.T) {

 	t.Run("Prebuilt workspace delete permissions", func(t *testing.T) {
 		t.Parallel()
-		if !dbtestutil.WillUsePostgres() {
-			t.Skip("this test requires postgres")
-		}

 		// Setup
 		db, pb := dbtestutil.NewDB(t, dbtestutil.WithDumpOnFailure())
@@ -29,7 +29,6 @@ import (

 	"github.com/coder/coder/v2/cli/cliui"
 	"github.com/coder/coder/v2/coderd/httpapi"
-	notificationsLib "github.com/coder/coder/v2/coderd/notifications"
 	"github.com/coder/coder/v2/coderd/tracing"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/codersdk/workspacesdk"
@@ -40,7 +39,6 @@ import (
 	"github.com/coder/coder/v2/scaletest/dashboard"
 	"github.com/coder/coder/v2/scaletest/harness"
 	"github.com/coder/coder/v2/scaletest/loadtestutil"
-	"github.com/coder/coder/v2/scaletest/notifications"
 	"github.com/coder/coder/v2/scaletest/reconnectingpty"
 	"github.com/coder/coder/v2/scaletest/workspacebuild"
 	"github.com/coder/coder/v2/scaletest/workspacetraffic"
@@ -66,6 +64,9 @@ func (r *RootCmd) scaletestCmd() *serpent.Command {
 			r.scaletestWorkspaceTraffic(),
 			r.scaletestAutostart(),
 			r.scaletestNotifications(),
+			r.scaletestTaskStatus(),
+			r.scaletestSMTP(),
+			r.scaletestPrebuilds(),
 		},
 	}

@@ -385,6 +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 {
@@ -1194,12 +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()
@@ -1244,15 +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)
@@ -1260,30 +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)
@@ -1308,10 +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"
@@ -1416,19 +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",
@@ -1464,13 +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",
@@ -1480,6 +1507,7 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *serpent.Command {
 		},
 	}

+	targetFlags.attach(&cmd.Options)
 	tracingFlags.attach(&cmd.Options)
 	strategy.attach(&cmd.Options)
 	cleanupStrategy.attach(&cmd.Options)
@@ -1921,259 +1949,6 @@ func (r *RootCmd) scaletestAutostart() *serpent.Command {
 	return cmd
 }

-func (r *RootCmd) scaletestNotifications() *serpent.Command {
-	var (
-		userCount           int64
-		ownerUserPercentage float64
-		notificationTimeout time.Duration
-		dialTimeout         time.Duration
-		noCleanup           bool
-
-		tracingFlags = &scaletestTracingFlags{}
-
-		// This test requires unlimited concurrency.
-		timeoutStrategy = &timeoutFlags{}
-		cleanupStrategy = newScaletestCleanupStrategy()
-		output          = &scaletestOutputFlags{}
-		prometheusFlags = &scaletestPrometheusFlags{}
-	)
-
-	cmd := &serpent.Command{
-		Use:   "notifications",
-		Short: "Simulate notification delivery by creating many users listening to notifications.",
-		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 userCount <= 0 {
-				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")
-			}
-
-			ownerUserCount := int64(float64(userCount) * ownerUserPercentage / 100)
-			if ownerUserCount == 0 && ownerUserPercentage > 0 {
-				ownerUserCount = 1
-			}
-			regularUserCount := userCount - ownerUserCount
-
-			_, _ = 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)
-
-			outputs, err := output.parse()
-			if err != nil {
-				return xerrors.Errorf("could not parse --output flags")
-			}
-
-			tracerProvider, closeTracing, tracingEnabled, err := tracingFlags.provider(ctx)
-			if err != nil {
-				return xerrors.Errorf("create tracer provider: %w", err)
-			}
-			tracer := tracerProvider.Tracer(scaletestTracerName)
-
-			reg := prometheus.NewRegistry()
-			metrics := notifications.NewMetrics(reg)
-
-			logger := inv.Logger
-			prometheusSrvClose := ServeHandler(ctx, logger, promhttp.HandlerFor(reg, promhttp.HandlerOpts{}), prometheusFlags.Address, "prometheus")
-			defer prometheusSrvClose()
-
-			defer func() {
-				_, _ = 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)
-			}()
-
-			_, _ = fmt.Fprintln(inv.Stderr, "Creating users...")
-
-			dialBarrier := &sync.WaitGroup{}
-			ownerWatchBarrier := &sync.WaitGroup{}
-			dialBarrier.Add(int(userCount))
-			ownerWatchBarrier.Add(int(ownerUserCount))
-
-			expectedNotifications := map[uuid.UUID]chan time.Time{
-				notificationsLib.TemplateUserAccountCreated: make(chan time.Time, 1),
-				notificationsLib.TemplateUserAccountDeleted: make(chan time.Time, 1),
-			}
-
-			configs := make([]notifications.Config, 0, userCount)
-			for range ownerUserCount {
-				config := notifications.Config{
-					User: createusers.Config{
-						OrganizationID: me.OrganizationIDs[0],
-					},
-					Roles:                 []string{codersdk.RoleOwner},
-					NotificationTimeout:   notificationTimeout,
-					DialTimeout:           dialTimeout,
-					DialBarrier:           dialBarrier,
-					ReceivingWatchBarrier: ownerWatchBarrier,
-					ExpectedNotifications: expectedNotifications,
-					Metrics:               metrics,
-				}
-				if err := config.Validate(); err != nil {
-					return xerrors.Errorf("validate config: %w", err)
-				}
-				configs = append(configs, config)
-			}
-			for range regularUserCount {
-				config := notifications.Config{
-					User: createusers.Config{
-						OrganizationID: me.OrganizationIDs[0],
-					},
-					Roles:                 []string{},
-					NotificationTimeout:   notificationTimeout,
-					DialTimeout:           dialTimeout,
-					DialBarrier:           dialBarrier,
-					ReceivingWatchBarrier: ownerWatchBarrier,
-					Metrics:               metrics,
-				}
-				if err := config.Validate(); err != nil {
-					return xerrors.Errorf("validate config: %w", err)
-				}
-				configs = append(configs, config)
-			}
-
-			go triggerUserNotifications(
-				ctx,
-				logger,
-				client,
-				me.OrganizationIDs[0],
-				dialBarrier,
-				dialTimeout,
-				expectedNotifications,
-			)
-
-			th := harness.NewTestHarness(timeoutStrategy.wrapStrategy(harness.ConcurrentExecutionStrategy{}), cleanupStrategy.toStrategy())
-
-			for i, config := range configs {
-				id := strconv.Itoa(i)
-				name := fmt.Sprintf("notifications-%s", id)
-				var runner harness.Runnable = notifications.NewRunner(client, config)
-				if tracingEnabled {
-					runner = &runnableTraceWrapper{
-						tracer:   tracer,
-						spanName: name,
-						runner:   runner,
-					}
-				}
-
-				th.AddRun(name, id, runner)
-			}
-
-			_, _ = fmt.Fprintln(inv.Stderr, "Running notification delivery scaletest...")
-			testCtx, testCancel := timeoutStrategy.toContext(ctx)
-			defer testCancel()
-			err = th.Run(testCtx)
-			if err != nil {
-				return xerrors.Errorf("run test harness (harness failure, not a test failure): %w", err)
-			}
-
-			// If the command was interrupted, skip stats.
-			if notifyCtx.Err() != nil {
-				return notifyCtx.Err()
-			}
-
-			res := th.Results()
-			for _, o := range outputs {
-				err = o.write(res, inv.Stdout)
-				if err != nil {
-					return xerrors.Errorf("write output %q to %q: %w", o.format, o.path, err)
-				}
-			}
-
-			if !noCleanup {
-				_, _ = fmt.Fprintln(inv.Stderr, "\nCleaning up...")
-				cleanupCtx, cleanupCancel := cleanupStrategy.toContext(ctx)
-				defer cleanupCancel()
-				err = th.Cleanup(cleanupCtx)
-				if err != nil {
-					return xerrors.Errorf("cleanup tests: %w", err)
-				}
-			}
-
-			if res.TotalFail > 0 {
-				return xerrors.New("load test failed, see above for more details")
-			}
-
-			return nil
-		},
-	}
-
-	cmd.Options = serpent.OptionSet{
-		{
-			Flag:          "user-count",
-			FlagShorthand: "c",
-			Env:           "CODER_SCALETEST_NOTIFICATION_USER_COUNT",
-			Description:   "Required: Total number of users to create.",
-			Value:         serpent.Int64Of(&userCount),
-			Required:      true,
-		},
-		{
-			Flag:        "owner-user-percentage",
-			Env:         "CODER_SCALETEST_NOTIFICATION_OWNER_USER_PERCENTAGE",
-			Default:     "20.0",
-			Description: "Percentage of users to assign Owner role to (0-100).",
-			Value:       serpent.Float64Of(&ownerUserPercentage),
-		},
-		{
-			Flag:        "notification-timeout",
-			Env:         "CODER_SCALETEST_NOTIFICATION_TIMEOUT",
-			Default:     "5m",
-			Description: "How long to wait for notifications after triggering.",
-			Value:       serpent.DurationOf(&notificationTimeout),
-		},
-		{
-			Flag:        "dial-timeout",
-			Env:         "CODER_SCALETEST_DIAL_TIMEOUT",
-			Default:     "2m",
-			Description: "Timeout for dialing the notification websocket endpoint.",
-			Value:       serpent.DurationOf(&dialTimeout),
-		},
-		{
-			Flag:        "no-cleanup",
-			Env:         "CODER_SCALETEST_NO_CLEANUP",
-			Description: "Do not clean up resources after the test completes.",
-			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
-}
-
 type runnableTraceWrapper struct {
 	tracer   trace.Tracer
 	spanName string
@@ -2183,8 +1958,9 @@ type runnableTraceWrapper struct {
 }

 var (
-	_ harness.Runnable  = &runnableTraceWrapper{}
-	_ harness.Cleanable = &runnableTraceWrapper{}
+	_ harness.Runnable    = &runnableTraceWrapper{}
+	_ harness.Cleanable   = &runnableTraceWrapper{}
+	_ harness.Collectable = &runnableTraceWrapper{}
 )

 func (r *runnableTraceWrapper) Run(ctx context.Context, id string, logs io.Writer) error {
@@ -2226,6 +2002,14 @@ func (r *runnableTraceWrapper) Cleanup(ctx context.Context, id string, logs io.W
 	return c.Cleanup(ctx, id, logs)
 }

+func (r *runnableTraceWrapper) GetMetrics() map[string]any {
+	c, ok := r.runner.(harness.Collectable)
+	if !ok {
+		return nil
+	}
+	return c.GetMetrics()
+}
+
 func getScaletestWorkspaces(ctx context.Context, client *codersdk.Client, owner, template string) ([]codersdk.Workspace, int, error) {
 	var (
 		pageNumber = 0
@@ -2374,73 +2158,6 @@ func parseTargetRange(name, targets string) (start, end int, err error) {
 	return start, end, nil
 }

-// triggerUserNotifications waits for all test users to connect,
-// then creates and deletes a test user to trigger notification events for testing.
-func triggerUserNotifications(
-	ctx context.Context,
-	logger slog.Logger,
-	client *codersdk.Client,
-	orgID uuid.UUID,
-	dialBarrier *sync.WaitGroup,
-	dialTimeout time.Duration,
-	expectedNotifications map[uuid.UUID]chan time.Time,
-) {
-	logger.Info(ctx, "waiting for all users to connect")
-
-	// Wait for all users to connect
-	waitCtx, cancel := context.WithTimeout(ctx, dialTimeout+30*time.Second)
-	defer cancel()
-
-	done := make(chan struct{})
-	go func() {
-		dialBarrier.Wait()
-		close(done)
-	}()
-
-	select {
-	case <-done:
-		logger.Info(ctx, "all users connected")
-	case <-waitCtx.Done():
-		if waitCtx.Err() == context.DeadlineExceeded {
-			logger.Error(ctx, "timeout waiting for users to connect")
-		} else {
-			logger.Info(ctx, "context canceled while waiting for users")
-		}
-		return
-	}
-
-	const (
-		triggerUsername = "scaletest-trigger-user"
-		triggerEmail    = "scaletest-trigger@example.com"
-	)
-
-	logger.Info(ctx, "creating test user to test notifications",
-		slog.F("username", triggerUsername),
-		slog.F("email", triggerEmail),
-		slog.F("org_id", orgID))
-
-	testUser, err := client.CreateUserWithOrgs(ctx, codersdk.CreateUserRequestWithOrgs{
-		OrganizationIDs: []uuid.UUID{orgID},
-		Username:        triggerUsername,
-		Email:           triggerEmail,
-		Password:        "test-password-123",
-	})
-	if err != nil {
-		logger.Error(ctx, "create test user", slog.Error(err))
-		return
-	}
-	expectedNotifications[notificationsLib.TemplateUserAccountCreated] <- time.Now()
-
-	err = client.DeleteUser(ctx, testUser.ID)
-	if err != nil {
-		logger.Error(ctx, "delete test user", slog.Error(err))
-		return
-	}
-	expectedNotifications[notificationsLib.TemplateUserAccountDeleted] <- time.Now()
-	close(expectedNotifications[notificationsLib.TemplateUserAccountCreated])
-	close(expectedNotifications[notificationsLib.TemplateUserAccountDeleted])
-}
-
 func createWorkspaceAppConfig(client *codersdk.Client, appHost, app string, workspace codersdk.Workspace, agent codersdk.WorkspaceAgent) (workspacetraffic.AppConfig, error) {
 	if app == "" {
 		return workspacetraffic.AppConfig{}, nil
@@ -4,16 +4,20 @@ package cli

 import (
 	"fmt"
+	"net/http"
+	"time"

 	"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/dynamicparameters"
 	"github.com/coder/coder/v2/scaletest/harness"
-	"github.com/coder/serpent"
 )

 const (
@@ -21,8 +25,15 @@ const (
 )

 func (r *RootCmd) scaletestDynamicParameters() *serpent.Command {
-	var templateName string
-	var numEvals int64
+	var (
+		templateName    string
+		provisionerTags []string
+		numEvals        int64
+		tracingFlags    = &scaletestTracingFlags{}
+		prometheusFlags = &scaletestPrometheusFlags{}
+		// This test requires unlimited concurrency
+		timeoutStrategy = &timeoutFlags{}
+	)
 	orgContext := NewOrganizationContext()
 	output := &scaletestOutputFlags{}

@@ -46,20 +57,63 @@ func (r *RootCmd) scaletestDynamicParameters() *serpent.Command {
 				return xerrors.Errorf("template cannot be empty")
 			}

+			tags, err := ParseProvisionerTags(provisionerTags)
+			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
+			}
+
+			client.HTTPClient = &http.Client{
+				Transport: &codersdk.HeaderTransport{
+					Transport: http.DefaultTransport,
+					Header: map[string][]string{
+						codersdk.BypassRatelimitHeader: {"true"},
+					},
+				},
+			}
+
+			reg := prometheus.NewRegistry()
+			metrics := dynamicparameters.NewMetrics(reg, "concurrent_evaluations")
+
 			logger := slog.Make(sloghuman.Sink(inv.Stdout)).Leveled(slog.LevelDebug)
-			partitions, err := dynamicparameters.SetupPartitions(ctx, client, org.ID, templateName, numEvals, logger)
+			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)
+
+			partitions, err := dynamicparameters.SetupPartitions(ctx, client, org.ID, templateName, tags, numEvals, logger)
 			if err != nil {
 				return xerrors.Errorf("setup dynamic parameters partitions: %w", err)
 			}

-			th := harness.NewTestHarness(harness.ConcurrentExecutionStrategy{}, harness.ConcurrentExecutionStrategy{})
-			reg := prometheus.NewRegistry()
-			metrics := dynamicparameters.NewMetrics(reg, "concurrent_evaluations")
+			th := harness.NewTestHarness(
+				timeoutStrategy.wrapStrategy(harness.ConcurrentExecutionStrategy{}),
+				// there is no cleanup since it's just a connection that we sever.
+				nil)

 			for i, part := range partitions {
 				for j := range part.ConcurrentEvaluations {
@@ -68,12 +122,21 @@ func (r *RootCmd) scaletestDynamicParameters() *serpent.Command {
 						Metrics:           metrics,
 						MetricLabelValues: []string{fmt.Sprintf("%d", part.ConcurrentEvaluations)},
 					}
-					runner := dynamicparameters.NewRunner(client, cfg)
+					var runner harness.Runnable = dynamicparameters.NewRunner(client, cfg)
+					if tracingEnabled {
+						runner = &runnableTraceWrapper{
+							tracer:   tracer,
+							spanName: fmt.Sprintf("%s/%d/%d", dynamicParametersTestName, i, j),
+							runner:   runner,
+						}
+					}
 					th.AddRun(dynamicParametersTestName, fmt.Sprintf("%d/%d", j, i), runner)
 				}
 			}

-			err = th.Run(ctx)
+			testCtx, testCancel := timeoutStrategy.toContext(ctx)
+			defer testCancel()
+			err = th.Run(testCtx)
 			if err != nil {
 				return xerrors.Errorf("run test harness: %w", err)
 			}
@@ -103,8 +166,16 @@ func (r *RootCmd) scaletestDynamicParameters() *serpent.Command {
 			Default:     "100",
 			Value:       serpent.Int64Of(&numEvals),
 		},
+		{
+			Flag:        "provisioner-tag",
+			Description: "Specify a set of tags to target provisioner daemons.",
+			Value:       serpent.StringArrayOf(&provisionerTags),
+		},
 	}
 	orgContext.AttachOptions(cmd)
 	output.attach(&cmd.Options)
+	tracingFlags.attach(&cmd.Options)
+	prometheusFlags.attach(&cmd.Options)
+	timeoutStrategy.attach(&cmd.Options)
 	return cmd
 }
@@ -0,0 +1,480 @@
+//go:build !slim
+
+package cli
+
+import (
+	"bytes"
+	"context"
+	"fmt"
+	"net/http"
+	"os/signal"
+	"strconv"
+	"strings"
+	"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"
+
+	notificationsLib "github.com/coder/coder/v2/coderd/notifications"
+	"github.com/coder/coder/v2/codersdk"
+	"github.com/coder/coder/v2/scaletest/createusers"
+	"github.com/coder/coder/v2/scaletest/harness"
+	"github.com/coder/coder/v2/scaletest/notifications"
+	"github.com/coder/serpent"
+)
+
+func (r *RootCmd) scaletestNotifications() *serpent.Command {
+	var (
+		userCount               int64
+		templateAdminPercentage float64
+		notificationTimeout     time.Duration
+		smtpRequestTimeout      time.Duration
+		dialTimeout             time.Duration
+		noCleanup               bool
+		smtpAPIURL              string
+
+		tracingFlags = &scaletestTracingFlags{}
+
+		// This test requires unlimited concurrency.
+		timeoutStrategy = &timeoutFlags{}
+		cleanupStrategy = newScaletestCleanupStrategy()
+		output          = &scaletestOutputFlags{}
+		prometheusFlags = &scaletestPrometheusFlags{}
+	)
+
+	cmd := &serpent.Command{
+		Use:   "notifications",
+		Short: "Simulate notification delivery by creating many users listening to notifications.",
+		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 userCount <= 0 {
+				return xerrors.Errorf("--user-count must be greater than 0")
+			}
+
+			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://")
+			}
+
+			templateAdminCount := int64(float64(userCount) * templateAdminPercentage / 100)
+			if templateAdminCount == 0 && templateAdminPercentage > 0 {
+				templateAdminCount = 1
+			}
+			regularUserCount := userCount - templateAdminCount
+
+			_, _ = fmt.Fprintf(inv.Stderr, "Distribution plan:\n")
+			_, _ = fmt.Fprintf(inv.Stderr, "  Total users: %d\n", userCount)
+			_, _ = 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 {
+				return xerrors.Errorf("could not parse --output flags")
+			}
+
+			tracerProvider, closeTracing, tracingEnabled, err := tracingFlags.provider(ctx)
+			if err != nil {
+				return xerrors.Errorf("create tracer provider: %w", err)
+			}
+			tracer := tracerProvider.Tracer(scaletestTracerName)
+
+			reg := prometheus.NewRegistry()
+			metrics := notifications.NewMetrics(reg)
+
+			logger := inv.Logger
+			prometheusSrvClose := ServeHandler(ctx, logger, promhttp.HandlerFor(reg, promhttp.HandlerOpts{}), prometheusFlags.Address, "prometheus")
+			defer prometheusSrvClose()
+
+			defer func() {
+				_, _ = 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)
+			}()
+
+			_, _ = fmt.Fprintln(inv.Stderr, "Creating users...")
+
+			dialBarrier := &sync.WaitGroup{}
+			templateAdminWatchBarrier := &sync.WaitGroup{}
+			dialBarrier.Add(int(userCount))
+			templateAdminWatchBarrier.Add(int(templateAdminCount))
+
+			expectedNotificationIDs := map[uuid.UUID]struct{}{
+				notificationsLib.TemplateTemplateDeleted: {},
+			}
+
+			triggerTimes := make(map[uuid.UUID]chan time.Time, len(expectedNotificationIDs))
+			for id := range expectedNotificationIDs {
+				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 templateAdminCount {
+				config := notifications.Config{
+					User: createusers.Config{
+						OrganizationID: me.OrganizationIDs[0],
+					},
+					Roles:                    []string{codersdk.RoleTemplateAdmin},
+					NotificationTimeout:      notificationTimeout,
+					DialTimeout:              dialTimeout,
+					DialBarrier:              dialBarrier,
+					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)
+				}
+				configs = append(configs, config)
+			}
+			for range regularUserCount {
+				config := notifications.Config{
+					User: createusers.Config{
+						OrganizationID: me.OrganizationIDs[0],
+					},
+					Roles:                 []string{},
+					NotificationTimeout:   notificationTimeout,
+					DialTimeout:           dialTimeout,
+					DialBarrier:           dialBarrier,
+					ReceivingWatchBarrier: templateAdminWatchBarrier,
+					Metrics:               metrics,
+				}
+				if err := config.Validate(); err != nil {
+					return xerrors.Errorf("validate config: %w", err)
+				}
+				configs = append(configs, config)
+			}
+
+			go triggerNotifications(
+				ctx,
+				logger,
+				client,
+				me.OrganizationIDs[0],
+				dialBarrier,
+				dialTimeout,
+				triggerTimes,
+			)
+
+			th := harness.NewTestHarness(timeoutStrategy.wrapStrategy(harness.ConcurrentExecutionStrategy{}), cleanupStrategy.toStrategy())
+
+			for i, config := range configs {
+				id := strconv.Itoa(i)
+				name := fmt.Sprintf("notifications-%s", id)
+				var runner harness.Runnable = notifications.NewRunner(client, config)
+				if tracingEnabled {
+					runner = &runnableTraceWrapper{
+						tracer:   tracer,
+						spanName: name,
+						runner:   runner,
+					}
+				}
+
+				th.AddRun(name, id, runner)
+			}
+
+			_, _ = fmt.Fprintln(inv.Stderr, "Running notification delivery scaletest...")
+			testCtx, testCancel := timeoutStrategy.toContext(ctx)
+			defer testCancel()
+			err = th.Run(testCtx)
+			if err != nil {
+				return xerrors.Errorf("run test harness (harness failure, not a test failure): %w", err)
+			}
+
+			// If the command was interrupted, skip stats.
+			if notifyCtx.Err() != nil {
+				return notifyCtx.Err()
+			}
+
+			res := th.Results()
+
+			if err := computeNotificationLatencies(ctx, logger, triggerTimes, res, metrics); err != nil {
+				return xerrors.Errorf("compute notification latencies: %w", err)
+			}
+
+			for _, o := range outputs {
+				err = o.write(res, inv.Stdout)
+				if err != nil {
+					return xerrors.Errorf("write output %q to %q: %w", o.format, o.path, err)
+				}
+			}
+
+			if !noCleanup {
+				_, _ = fmt.Fprintln(inv.Stderr, "\nCleaning up...")
+				cleanupCtx, cleanupCancel := cleanupStrategy.toContext(ctx)
+				defer cleanupCancel()
+				err = th.Cleanup(cleanupCtx)
+				if err != nil {
+					return xerrors.Errorf("cleanup tests: %w", err)
+				}
+			}
+
+			if res.TotalFail > 0 {
+				return xerrors.New("load test failed, see above for more details")
+			}
+
+			return nil
+		},
+	}
+
+	cmd.Options = serpent.OptionSet{
+		{
+			Flag:          "user-count",
+			FlagShorthand: "c",
+			Env:           "CODER_SCALETEST_NOTIFICATION_USER_COUNT",
+			Description:   "Required: Total number of users to create.",
+			Value:         serpent.Int64Of(&userCount),
+			Required:      true,
+		},
+		{
+			Flag:        "template-admin-percentage",
+			Env:         "CODER_SCALETEST_NOTIFICATION_TEMPLATE_ADMIN_PERCENTAGE",
+			Default:     "20.0",
+			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:     "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:     "10m",
+			Description: "Timeout for dialing the notification websocket endpoint.",
+			Value:       serpent.DurationOf(&dialTimeout),
+		},
+		{
+			Flag:        "no-cleanup",
+			Env:         "CODER_SCALETEST_NO_CLEANUP",
+			Description: "Do not clean up resources after the test completes.",
+			Value:       serpent.BoolOf(&noCleanup),
+		},
+		{
+			Flag:        "smtp-api-url",
+			Env:         "CODER_SCALETEST_SMTP_API_URL",
+			Description: "SMTP mock HTTP API address.",
+			Value:       serpent.StringOf(&smtpAPIURL),
+		},
+	}
+
+	tracingFlags.attach(&cmd.Options)
+	timeoutStrategy.attach(&cmd.Options)
+	cleanupStrategy.attach(&cmd.Options)
+	output.attach(&cmd.Options)
+	prometheusFlags.attach(&cmd.Options)
+	return cmd
+}
+
+func computeNotificationLatencies(
+	ctx context.Context,
+	logger slog.Logger,
+	expectedNotifications map[uuid.UUID]chan time.Time,
+	results harness.Results,
+	metrics *notifications.Metrics,
+) error {
+	triggerTimes := make(map[uuid.UUID]time.Time)
+	for notificationID, triggerTimeChan := range expectedNotifications {
+		select {
+		case triggerTime := <-triggerTimeChan:
+			triggerTimes[notificationID] = triggerTime
+			logger.Info(ctx, "received trigger time",
+				slog.F("notification_id", notificationID),
+				slog.F("trigger_time", triggerTime))
+		default:
+			logger.Warn(ctx, "no trigger time received for notification",
+				slog.F("notification_id", notificationID))
+		}
+	}
+
+	if len(triggerTimes) == 0 {
+		logger.Warn(ctx, "no trigger times available, skipping latency computation")
+		return nil
+	}
+
+	var totalLatencies int
+	for runID, runResult := range results.Runs {
+		if runResult.Error != nil {
+			logger.Debug(ctx, "skipping failed run for latency computation",
+				slog.F("run_id", runID))
+			continue
+		}
+
+		if runResult.Metrics == nil {
+			continue
+		}
+
+		// Process websocket notifications.
+		if wsReceiptTimes, ok := runResult.Metrics[notifications.WebsocketNotificationReceiptTimeMetric].(map[uuid.UUID]time.Time); ok {
+			for notificationID, receiptTime := range wsReceiptTimes {
+				if triggerTime, ok := triggerTimes[notificationID]; ok {
+					latency := receiptTime.Sub(triggerTime)
+					metrics.RecordLatency(latency, notificationID.String(), notifications.NotificationTypeWebsocket)
+					totalLatencies++
+					logger.Debug(ctx, "computed websocket latency",
+						slog.F("run_id", runID),
+						slog.F("notification_id", notificationID),
+						slog.F("latency", latency))
+				}
+			}
+		}
+
+		// Process SMTP notifications
+		if smtpReceiptTimes, ok := runResult.Metrics[notifications.SMTPNotificationReceiptTimeMetric].(map[uuid.UUID]time.Time); ok {
+			for notificationID, receiptTime := range smtpReceiptTimes {
+				if triggerTime, ok := triggerTimes[notificationID]; ok {
+					latency := receiptTime.Sub(triggerTime)
+					metrics.RecordLatency(latency, notificationID.String(), notifications.NotificationTypeSMTP)
+					totalLatencies++
+					logger.Debug(ctx, "computed SMTP latency",
+						slog.F("run_id", runID),
+						slog.F("notification_id", notificationID),
+						slog.F("latency", latency))
+				}
+			}
+		}
+	}
+
+	logger.Info(ctx, "finished computing notification latencies",
+		slog.F("total_runs", results.TotalRuns),
+		slog.F("total_latencies_computed", totalLatencies))
+
+	return nil
+}
+
+// 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,
+	orgID uuid.UUID,
+	dialBarrier *sync.WaitGroup,
+	dialTimeout time.Duration,
+	expectedNotifications map[uuid.UUID]chan time.Time,
+) {
+	logger.Info(ctx, "waiting for all users to connect")
+
+	// Wait for all users to connect
+	waitCtx, cancel := context.WithTimeout(ctx, dialTimeout+30*time.Second)
+	defer cancel()
+
+	done := make(chan struct{})
+	go func() {
+		dialBarrier.Wait()
+		close(done)
+	}()
+
+	select {
+	case <-done:
+		logger.Info(ctx, "all users connected")
+	case <-waitCtx.Done():
+		if waitCtx.Err() == context.DeadlineExceeded {
+			logger.Error(ctx, "timeout waiting for users to connect")
+		} else {
+			logger.Info(ctx, "context canceled while waiting for users")
+		}
+		return
+	}
+
+	logger.Info(ctx, "creating test template to test notifications")
+
+	// 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))
+
+	// 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 template version", slog.Error(err))
+		return
+	}
+	logger.Info(ctx, "test template version created", slog.F("template_version_id", version.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, "create test template", slog.Error(err))
+		return
+	}
+	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])
+}
@@ -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
+}
@@ -0,0 +1,112 @@
+//go:build !slim
+
+package cli
+
+import (
+	"fmt"
+	"os/signal"
+	"time"
+
+	"golang.org/x/xerrors"
+
+	"cdr.dev/slog"
+	"cdr.dev/slog/sloggers/sloghuman"
+	"github.com/coder/coder/v2/scaletest/smtpmock"
+	"github.com/coder/serpent"
+)
+
+func (*RootCmd) scaletestSMTP() *serpent.Command {
+	var (
+		hostAddress  string
+		smtpPort     int64
+		apiPort      int64
+		purgeAtCount int64
+	)
+	cmd := &serpent.Command{
+		Use:   "smtp",
+		Short: "Start a mock SMTP server for testing",
+		Long: `Start a mock SMTP server with an HTTP API server that can be used to purge
+messages and get messages by email.`,
+		Handler: func(inv *serpent.Invocation) error {
+			ctx := inv.Context()
+			notifyCtx, stop := signal.NotifyContext(ctx, StopSignals...)
+			defer stop()
+			ctx = notifyCtx
+
+			logger := slog.Make(sloghuman.Sink(inv.Stderr)).Leveled(slog.LevelInfo)
+			config := smtpmock.Config{
+				HostAddress: hostAddress,
+				SMTPPort:    int(smtpPort),
+				APIPort:     int(apiPort),
+				Logger:      logger,
+			}
+			srv := new(smtpmock.Server)
+
+			if err := srv.Start(ctx, config); err != nil {
+				return xerrors.Errorf("start mock SMTP server: %w", err)
+			}
+			defer func() {
+				_ = srv.Stop()
+			}()
+
+			_, _ = fmt.Fprintf(inv.Stdout, "Mock SMTP server started on %s\n", srv.SMTPAddress())
+			_, _ = fmt.Fprintf(inv.Stdout, "HTTP API server started on %s\n", srv.APIAddress())
+			if purgeAtCount > 0 {
+				_, _ = fmt.Fprintf(inv.Stdout, "  Auto-purge when message count reaches %d\n", purgeAtCount)
+			}
+
+			ticker := time.NewTicker(10 * time.Second)
+			defer ticker.Stop()
+
+			for {
+				select {
+				case <-ctx.Done():
+					_, _ = fmt.Fprintf(inv.Stdout, "\nTotal messages received since last purge: %d\n", srv.MessageCount())
+					return nil
+				case <-ticker.C:
+					count := srv.MessageCount()
+					if count > 0 {
+						_, _ = fmt.Fprintf(inv.Stdout, "Messages received: %d\n", count)
+					}
+
+					if purgeAtCount > 0 && int64(count) >= purgeAtCount {
+						_, _ = fmt.Fprintf(inv.Stdout, "Message count (%d) reached threshold (%d). Purging...\n", count, purgeAtCount)
+						srv.Purge()
+						continue
+					}
+				}
+			}
+		},
+	}
+
+	cmd.Options = []serpent.Option{
+		{
+			Flag:        "host-address",
+			Env:         "CODER_SCALETEST_SMTP_HOST_ADDRESS",
+			Default:     "localhost",
+			Description: "Host address to bind the mock SMTP and API servers.",
+			Value:       serpent.StringOf(&hostAddress),
+		},
+		{
+			Flag:        "smtp-port",
+			Env:         "CODER_SCALETEST_SMTP_PORT",
+			Description: "Port for the mock SMTP server. Uses a random port if not specified.",
+			Value:       serpent.Int64Of(&smtpPort),
+		},
+		{
+			Flag:        "api-port",
+			Env:         "CODER_SCALETEST_SMTP_API_PORT",
+			Description: "Port for the HTTP API server. Uses a random port if not specified.",
+			Value:       serpent.Int64Of(&apiPort),
+		},
+		{
+			Flag:        "purge-at-count",
+			Env:         "CODER_SCALETEST_SMTP_PURGE_AT_COUNT",
+			Default:     "100000",
+			Description: "Maximum number of messages to keep before auto-purging. Set to 0 to disable.",
+			Value:       serpent.Int64Of(&purgeAtCount),
+		},
+	}
+
+	return cmd
+}
@@ -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
+}
@@ -1,111 +0,0 @@
-package cli
-
-import (
-	"fmt"
-	"strings"
-	"time"
-
-	"github.com/google/uuid"
-	"golang.org/x/xerrors"
-
-	"github.com/coder/pretty"
-
-	"github.com/coder/coder/v2/cli/cliui"
-	"github.com/coder/coder/v2/codersdk"
-	"github.com/coder/serpent"
-)
-
-func (r *RootCmd) taskDelete() *serpent.Command {
-	cmd := &serpent.Command{
-		Use:   "delete <task> [<task> ...]",
-		Short: "Delete experimental tasks",
-		Long: FormatExamples(
-			Example{
-				Description: "Delete a single task.",
-				Command:     "$ coder exp task delete task1",
-			},
-			Example{
-				Description: "Delete multiple tasks.",
-				Command:     "$ coder exp task delete task1 task2 task3",
-			},
-			Example{
-				Description: "Delete a task without confirmation.",
-				Command:     "$ coder exp task delete task4 --yes",
-			},
-		),
-		Middleware: serpent.Chain(
-			serpent.RequireRangeArgs(1, -1),
-		),
-		Options: serpent.OptionSet{
-			cliui.SkipPromptOption(),
-		},
-		Handler: func(inv *serpent.Invocation) error {
-			ctx := inv.Context()
-			client, err := r.InitClient(inv)
-			if err != nil {
-				return err
-			}
-			exp := codersdk.NewExperimentalClient(client)
-
-			type toDelete struct {
-				ID      uuid.UUID
-				Owner   string
-				Display string
-			}
-
-			var items []toDelete
-			for _, identifier := range inv.Args {
-				identifier = strings.TrimSpace(identifier)
-				if identifier == "" {
-					return xerrors.New("task identifier cannot be empty or whitespace")
-				}
-
-				// Check task identifier, try UUID first.
-				if id, err := uuid.Parse(identifier); err == nil {
-					task, err := exp.TaskByID(ctx, id)
-					if err != nil {
-						return xerrors.Errorf("resolve task %q: %w", identifier, err)
-					}
-					display := fmt.Sprintf("%s/%s", task.OwnerName, task.Name)
-					items = append(items, toDelete{ID: id, Display: display, Owner: task.OwnerName})
-					continue
-				}
-
-				// Non-UUID, treat as a workspace identifier (name or owner/name).
-				ws, err := namedWorkspace(ctx, client, identifier)
-				if err != nil {
-					return xerrors.Errorf("resolve task %q: %w", identifier, err)
-				}
-				display := ws.FullName()
-				items = append(items, toDelete{ID: ws.ID, Display: display, Owner: ws.OwnerName})
-			}
-
-			// Confirm deletion of the tasks.
-			var displayList []string
-			for _, it := range items {
-				displayList = append(displayList, it.Display)
-			}
-			_, err = cliui.Prompt(inv, cliui.PromptOptions{
-				Text:      fmt.Sprintf("Delete these tasks: %s?", pretty.Sprint(cliui.DefaultStyles.Code, strings.Join(displayList, ", "))),
-				IsConfirm: true,
-				Default:   cliui.ConfirmNo,
-			})
-			if err != nil {
-				return err
-			}
-
-			for _, item := range items {
-				if err := exp.DeleteTask(ctx, item.Owner, item.ID); err != nil {
-					return xerrors.Errorf("delete task %q: %w", item.Display, err)
-				}
-				_, _ = fmt.Fprintln(
-					inv.Stdout, "Deleted task "+pretty.Sprint(cliui.DefaultStyles.Keyword, item.Display)+" at "+cliui.Timestamp(time.Now()),
-				)
-			}
-
-			return nil
-		},
-	}
-
-	return cmd
-}
@@ -1,200 +0,0 @@
-package cli_test
-
-import (
-	"context"
-	"encoding/json"
-	"fmt"
-	"net/http"
-	"net/http/httptest"
-	"strings"
-	"testing"
-	"time"
-
-	"github.com/google/uuid"
-	"github.com/stretchr/testify/assert"
-	"github.com/stretchr/testify/require"
-
-	"github.com/coder/coder/v2/cli/clitest"
-	"github.com/coder/coder/v2/coderd/httpapi"
-	"github.com/coder/coder/v2/codersdk"
-	"github.com/coder/coder/v2/testutil"
-)
-
-func Test_TaskLogs(t *testing.T) {
-	t.Parallel()
-
-	var (
-		clock = time.Date(2025, 8, 26, 12, 34, 56, 0, time.UTC)
-
-		taskID   = uuid.MustParse("11111111-1111-1111-1111-111111111111")
-		taskName = "task-workspace"
-
-		taskLogs = []codersdk.TaskLogEntry{
-			{
-				ID:      0,
-				Content: "What is 1 + 1?",
-				Type:    codersdk.TaskLogTypeInput,
-				Time:    clock,
-			},
-			{
-				ID:      1,
-				Content: "2",
-				Type:    codersdk.TaskLogTypeOutput,
-				Time:    clock.Add(1 * time.Second),
-			},
-		}
-	)
-
-	tests := []struct {
-		args        []string
-		expectTable string
-		expectLogs  []codersdk.TaskLogEntry
-		expectError string
-		handler     func(t *testing.T, ctx context.Context) http.HandlerFunc
-	}{
-		{
-			args:       []string{taskName, "--output", "json"},
-			expectLogs: taskLogs,
-			handler: func(t *testing.T, ctx context.Context) http.HandlerFunc {
-				return func(w http.ResponseWriter, r *http.Request) {
-					switch r.URL.Path {
-					case fmt.Sprintf("/api/v2/users/me/workspace/%s", taskName):
-						httpapi.Write(ctx, w, http.StatusOK, codersdk.Workspace{
-							ID: taskID,
-						})
-					case fmt.Sprintf("/api/experimental/tasks/me/%s/logs", taskID.String()):
-						httpapi.Write(ctx, w, http.StatusOK, codersdk.TaskLogsResponse{
-							Logs: taskLogs,
-						})
-					default:
-						t.Errorf("unexpected path: %s", r.URL.Path)
-					}
-				}
-			},
-		},
-		{
-			args:       []string{taskID.String(), "--output", "json"},
-			expectLogs: taskLogs,
-			handler: func(t *testing.T, ctx context.Context) http.HandlerFunc {
-				return func(w http.ResponseWriter, r *http.Request) {
-					switch r.URL.Path {
-					case fmt.Sprintf("/api/experimental/tasks/me/%s/logs", taskID.String()):
-						httpapi.Write(ctx, w, http.StatusOK, codersdk.TaskLogsResponse{
-							Logs: taskLogs,
-						})
-					default:
-						t.Errorf("unexpected path: %s", r.URL.Path)
-					}
-				}
-			},
-		},
-		{
-			args: []string{taskID.String()},
-			expectTable: `
-TYPE    CONTENT
-input   What is 1 + 1?
-output  2`,
-			handler: func(t *testing.T, ctx context.Context) http.HandlerFunc {
-				return func(w http.ResponseWriter, r *http.Request) {
-					switch r.URL.Path {
-					case fmt.Sprintf("/api/experimental/tasks/me/%s/logs", taskID.String()):
-						httpapi.Write(ctx, w, http.StatusOK, codersdk.TaskLogsResponse{
-							Logs: taskLogs,
-						})
-					default:
-						t.Errorf("unexpected path: %s", r.URL.Path)
-					}
-				}
-			},
-		},
-		{
-			args:        []string{"doesnotexist"},
-			expectError: httpapi.ResourceNotFoundResponse.Message,
-			handler: func(t *testing.T, ctx context.Context) http.HandlerFunc {
-				return func(w http.ResponseWriter, r *http.Request) {
-					switch r.URL.Path {
-					case "/api/v2/users/me/workspace/doesnotexist":
-						httpapi.ResourceNotFound(w)
-					default:
-						t.Errorf("unexpected path: %s", r.URL.Path)
-					}
-				}
-			},
-		},
-		{
-			args:        []string{uuid.Nil.String()}, // uuid does not exist
-			expectError: httpapi.ResourceNotFoundResponse.Message,
-			handler: func(t *testing.T, ctx context.Context) http.HandlerFunc {
-				return func(w http.ResponseWriter, r *http.Request) {
-					switch r.URL.Path {
-					case fmt.Sprintf("/api/experimental/tasks/me/%s/logs", uuid.Nil.String()):
-						httpapi.ResourceNotFound(w)
-					default:
-						t.Errorf("unexpected path: %s", r.URL.Path)
-					}
-				}
-			},
-		},
-		{
-			args:        []string{"err-fetching-logs"},
-			expectError: assert.AnError.Error(),
-			handler: func(t *testing.T, ctx context.Context) http.HandlerFunc {
-				return func(w http.ResponseWriter, r *http.Request) {
-					switch r.URL.Path {
-					case "/api/v2/users/me/workspace/err-fetching-logs":
-						httpapi.Write(ctx, w, http.StatusOK, codersdk.Workspace{
-							ID: taskID,
-						})
-					case fmt.Sprintf("/api/experimental/tasks/me/%s/logs", taskID.String()):
-						httpapi.InternalServerError(w, assert.AnError)
-					default:
-						t.Errorf("unexpected path: %s", r.URL.Path)
-					}
-				}
-			},
-		},
-	}
-
-	for _, tt := range tests {
-		t.Run(strings.Join(tt.args, ","), func(t *testing.T) {
-			t.Parallel()
-
-			var (
-				ctx    = testutil.Context(t, testutil.WaitShort)
-				srv    = httptest.NewServer(tt.handler(t, ctx))
-				client = codersdk.New(testutil.MustURL(t, srv.URL))
-				args   = []string{"exp", "task", "logs"}
-				stdout strings.Builder
-				err    error
-			)
-
-			t.Cleanup(srv.Close)
-
-			inv, root := clitest.New(t, append(args, tt.args...)...)
-			inv.Stdout = &stdout
-			inv.Stderr = &stdout
-			clitest.SetupConfig(t, client, root)
-
-			err = inv.WithContext(ctx).Run()
-			if tt.expectError == "" {
-				assert.NoError(t, err)
-			} else {
-				assert.ErrorContains(t, err, tt.expectError)
-			}
-
-			if tt.expectTable != "" {
-				if diff := tableDiff(tt.expectTable, stdout.String()); diff != "" {
-					t.Errorf("unexpected output diff (-want +got):\n%s", diff)
-				}
-			}
-
-			if tt.expectLogs != nil {
-				var logs []codersdk.TaskLogEntry
-				err = json.NewDecoder(strings.NewReader(stdout.String())).Decode(&logs)
-				require.NoError(t, err)
-
-				assert.Equal(t, tt.expectLogs, logs)
-			}
-		})
-	}
-}
@@ -1,173 +0,0 @@
-package cli_test
-
-import (
-	"context"
-	"fmt"
-	"net/http"
-	"net/http/httptest"
-	"strings"
-	"testing"
-
-	"github.com/google/uuid"
-	"github.com/stretchr/testify/assert"
-
-	"github.com/coder/coder/v2/cli/clitest"
-	"github.com/coder/coder/v2/coderd/httpapi"
-	"github.com/coder/coder/v2/codersdk"
-	"github.com/coder/coder/v2/testutil"
-)
-
-func Test_TaskSend(t *testing.T) {
-	t.Parallel()
-
-	var (
-		taskName = "task-workspace"
-		taskID   = uuid.MustParse("11111111-1111-1111-1111-111111111111")
-	)
-
-	tests := []struct {
-		args        []string
-		stdin       string
-		expectError string
-		handler     func(t *testing.T, ctx context.Context) http.HandlerFunc
-	}{
-		{
-			args: []string{taskName, "carry on with the task"},
-			handler: func(t *testing.T, ctx context.Context) http.HandlerFunc {
-				return func(w http.ResponseWriter, r *http.Request) {
-					switch r.URL.Path {
-					case fmt.Sprintf("/api/v2/users/me/workspace/%s", taskName):
-						httpapi.Write(ctx, w, http.StatusOK, codersdk.Workspace{
-							ID: taskID,
-						})
-					case fmt.Sprintf("/api/experimental/tasks/me/%s/send", taskID.String()):
-						var req codersdk.TaskSendRequest
-						if !httpapi.Read(ctx, w, r, &req) {
-							return
-						}
-
-						assert.Equal(t, "carry on with the task", req.Input)
-
-						httpapi.Write(ctx, w, http.StatusNoContent, nil)
-					default:
-						t.Errorf("unexpected path: %s", r.URL.Path)
-					}
-				}
-			},
-		},
-		{
-			args: []string{taskID.String(), "carry on with the task"},
-			handler: func(t *testing.T, ctx context.Context) http.HandlerFunc {
-				return func(w http.ResponseWriter, r *http.Request) {
-					switch r.URL.Path {
-					case fmt.Sprintf("/api/experimental/tasks/me/%s/send", taskID.String()):
-						var req codersdk.TaskSendRequest
-						if !httpapi.Read(ctx, w, r, &req) {
-							return
-						}
-
-						assert.Equal(t, "carry on with the task", req.Input)
-
-						httpapi.Write(ctx, w, http.StatusNoContent, nil)
-					default:
-						t.Errorf("unexpected path: %s", r.URL.Path)
-					}
-				}
-			},
-		},
-		{
-			args:  []string{taskName, "--stdin"},
-			stdin: "carry on with the task",
-			handler: func(t *testing.T, ctx context.Context) http.HandlerFunc {
-				return func(w http.ResponseWriter, r *http.Request) {
-					switch r.URL.Path {
-					case fmt.Sprintf("/api/v2/users/me/workspace/%s", taskName):
-						httpapi.Write(ctx, w, http.StatusOK, codersdk.Workspace{
-							ID: taskID,
-						})
-					case fmt.Sprintf("/api/experimental/tasks/me/%s/send", taskID.String()):
-						var req codersdk.TaskSendRequest
-						if !httpapi.Read(ctx, w, r, &req) {
-							return
-						}
-
-						assert.Equal(t, "carry on with the task", req.Input)
-
-						httpapi.Write(ctx, w, http.StatusNoContent, nil)
-					default:
-						t.Errorf("unexpected path: %s", r.URL.Path)
-					}
-				}
-			},
-		},
-		{
-			args:        []string{"doesnotexist", "some task input"},
-			expectError: httpapi.ResourceNotFoundResponse.Message,
-			handler: func(t *testing.T, ctx context.Context) http.HandlerFunc {
-				return func(w http.ResponseWriter, r *http.Request) {
-					switch r.URL.Path {
-					case "/api/v2/users/me/workspace/doesnotexist":
-						httpapi.ResourceNotFound(w)
-					default:
-						t.Errorf("unexpected path: %s", r.URL.Path)
-					}
-				}
-			},
-		},
-		{
-			args:        []string{uuid.Nil.String(), "some task input"},
-			expectError: httpapi.ResourceNotFoundResponse.Message,
-			handler: func(t *testing.T, ctx context.Context) http.HandlerFunc {
-				return func(w http.ResponseWriter, r *http.Request) {
-					switch r.URL.Path {
-					case fmt.Sprintf("/api/experimental/tasks/me/%s/send", uuid.Nil.String()):
-						httpapi.ResourceNotFound(w)
-					default:
-						t.Errorf("unexpected path: %s", r.URL.Path)
-					}
-				}
-			},
-		},
-		{
-			args:        []string{uuid.Nil.String(), "some task input"},
-			expectError: assert.AnError.Error(),
-			handler: func(t *testing.T, ctx context.Context) http.HandlerFunc {
-				return func(w http.ResponseWriter, r *http.Request) {
-					switch r.URL.Path {
-					case fmt.Sprintf("/api/experimental/tasks/me/%s/send", uuid.Nil.String()):
-						httpapi.InternalServerError(w, assert.AnError)
-					default:
-						t.Errorf("unexpected path: %s", r.URL.Path)
-					}
-				}
-			},
-		},
-	}
-
-	for _, tt := range tests {
-		t.Run(strings.Join(tt.args, ","), func(t *testing.T) {
-			t.Parallel()
-
-			var (
-				ctx    = testutil.Context(t, testutil.WaitShort)
-				srv    = httptest.NewServer(tt.handler(t, ctx))
-				client = codersdk.New(testutil.MustURL(t, srv.URL))
-				args   = []string{"exp", "task", "send"}
-				err    error
-			)
-
-			t.Cleanup(srv.Close)
-
-			inv, root := clitest.New(t, append(args, tt.args...)...)
-			inv.Stdin = strings.NewReader(tt.stdin)
-			clitest.SetupConfig(t, client, root)
-
-			err = inv.WithContext(ctx).Run()
-			if tt.expectError == "" {
-				assert.NoError(t, err)
-			} else {
-				assert.ErrorContains(t, err, tt.expectError)
-			}
-		})
-	}
-}
@@ -0,0 +1,426 @@
+package cli_test
+
+import (
+	"bytes"
+	"crypto/rand"
+	"encoding/binary"
+	"fmt"
+	"net/url"
+	"os"
+	"path"
+	"runtime"
+	"testing"
+	"time"
+
+	"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/cli/config"
+	"github.com/coder/coder/v2/cli/sessionstore"
+	"github.com/coder/coder/v2/coderd/coderdtest"
+	"github.com/coder/coder/v2/pty/ptytest"
+	"github.com/coder/serpent"
+)
+
+// keyringTestServiceName generates a unique service name for keyring tests
+// using the test name and a nanosecond timestamp to prevent collisions.
+func keyringTestServiceName(t *testing.T) string {
+	t.Helper()
+	var n uint32
+	err := binary.Read(rand.Reader, binary.BigEndian, &n)
+	if err != nil {
+		t.Fatal(err)
+	}
+	return fmt.Sprintf("%s_%v_%d", t.Name(), time.Now().UnixNano(), n)
+}
+
+type keyringTestEnv struct {
+	serviceName string
+	keyring     sessionstore.Keyring
+	inv         *serpent.Invocation
+	cfg         config.Root
+	clientURL   *url.URL
+}
+
+func setupKeyringTestEnv(t *testing.T, clientURL string, args ...string) keyringTestEnv {
+	t.Helper()
+
+	var root cli.RootCmd
+
+	cmd, err := root.Command(root.AGPL())
+	require.NoError(t, err)
+
+	serviceName := keyringTestServiceName(t)
+	root.WithKeyringServiceName(serviceName)
+	root.UseKeyringWithGlobalConfig()
+
+	inv, cfg := clitest.NewWithDefaultKeyringCommand(t, cmd, args...)
+
+	parsedURL, err := url.Parse(clientURL)
+	require.NoError(t, err)
+
+	backend := sessionstore.NewKeyringWithService(serviceName)
+	t.Cleanup(func() {
+		_ = backend.Delete(parsedURL)
+	})
+
+	return keyringTestEnv{serviceName, backend, inv, cfg, parsedURL}
+}
+
+func TestUseKeyring(t *testing.T) {
+	// Verify that the --use-keyring flag default 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()
+
+		if runtime.GOOS != "windows" && runtime.GOOS != "darwin" {
+			t.Skip("keyring is not supported on this OS")
+		}
+
+		// 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 which defaults to using the keyring
+		env := setupKeyringTestEnv(t, client.URL.String(),
+			"login",
+			"--force-tty",
+			"--no-open",
+			client.URL.String())
+		inv := env.inv
+		inv.Stdin = pty.Input()
+		inv.Stdout = pty.Output()
+
+		// 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(env.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 OS keyring
+		cred, err := env.keyring.Read(env.clientURL)
+		require.NoError(t, err, "credential should be stored in OS keyring")
+		require.Equal(t, client.SessionToken(), cred, "stored token should match login token")
+	})
+
+	t.Run("Logout", func(t *testing.T) {
+		t.Parallel()
+
+		if runtime.GOOS != "windows" && runtime.GOOS != "darwin" {
+			t.Skip("keyring is not supported on this OS")
+		}
+
+		// 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 the keyring (default)
+		env := setupKeyringTestEnv(t, client.URL.String(),
+			"login",
+			"--force-tty",
+			"--no-open",
+			client.URL.String(),
+		)
+		loginInv := env.inv
+		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
+
+		// Verify credential exists in OS keyring
+		cred, err := env.keyring.Read(env.clientURL)
+		require.NoError(t, err, "read credential should succeed before logout")
+		require.NotEmpty(t, cred, "credential should exist before logout")
+
+		// Now logout using the same keyring service name
+		var logoutRoot cli.RootCmd
+		logoutCmd, err := logoutRoot.Command(logoutRoot.AGPL())
+		require.NoError(t, err)
+		logoutRoot.WithKeyringServiceName(env.serviceName)
+		logoutRoot.UseKeyringWithGlobalConfig()
+
+		logoutInv, _ := clitest.NewWithDefaultKeyringCommand(t, logoutCmd,
+			"logout",
+			"--yes",
+			"--global-config", string(env.cfg),
+		)
+
+		var logoutOut bytes.Buffer
+		logoutInv.Stdout = &logoutOut
+
+		err = logoutInv.Run()
+		require.NoError(t, err, "logout should succeed")
+
+		// Verify the credential was deleted from OS keyring
+		_, err = env.keyring.Read(env.clientURL)
+		require.ErrorIs(t, err, os.ErrNotExist, "credential should be deleted from keyring after logout")
+	})
+
+	t.Run("DefaultFileStorage", func(t *testing.T) {
+		t.Parallel()
+
+		if runtime.GOOS != "linux" {
+			t.Skip("file storage is the default for Linux")
+		}
+
+		// Create a test server
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+
+		// Create a pty for interactive prompts
+		pty := ptytest.New(t)
+
+		env := setupKeyringTestEnv(t, client.URL.String(),
+			"login",
+			"--force-tty",
+			"--no-open",
+			client.URL.String(),
+		)
+		inv := env.inv
+		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(env.cfg), "session")
+		_, err := os.Stat(sessionFile)
+		require.NoError(t, err, "session file should exist when NOT using --use-keyring on Linux")
+
+		// 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 set to disable keyring usage,
+		// which should have the same behavior on all platforms.
+		env := setupKeyringTestEnv(t, client.URL.String(),
+			"login",
+			"--force-tty",
+			"--no-open",
+			client.URL.String(),
+		)
+		inv := env.inv
+		inv.Stdin = pty.Input()
+		inv.Stdout = pty.Output()
+		inv.Environ.Set("CODER_USE_KEYRING", "false")
+
+		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(env.cfg), "session")
+		_, err := os.Stat(sessionFile)
+		require.NoError(t, err, "session file should exist when CODER_USE_KEYRING set to false")
+
+		// 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("DisableKeyringWithFlag", func(t *testing.T) {
+		t.Parallel()
+
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+		pty := ptytest.New(t)
+
+		// Login with --use-keyring=false to explicitly disable keyring usage, which
+		// should have the same behavior on all platforms.
+		env := setupKeyringTestEnv(t, client.URL.String(),
+			"login",
+			"--use-keyring=false",
+			"--force-tty",
+			"--no-open",
+			client.URL.String(),
+		)
+		inv := env.inv
+		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(env.cfg), "session")
+		_, err := os.Stat(sessionFile)
+		require.NoError(t, err, "session file should exist when --use-keyring=false is specified")
+
+		// 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")
+	})
+}
+
+func TestUseKeyringUnsupportedOS(t *testing.T) {
+	// Verify that on unsupported operating systems, file-based storage is used
+	// automatically even when --use-keyring is set to true (the default).
+	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)
+	}
+
+	t.Run("LoginWithDefaultKeyring", func(t *testing.T) {
+		t.Parallel()
+
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+		pty := ptytest.New(t)
+
+		env := setupKeyringTestEnv(t, client.URL.String(),
+			"login",
+			"--force-tty",
+			"--no-open",
+			client.URL.String(),
+		)
+		inv := env.inv
+		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 (automatic fallback to file storage)
+		sessionFile := path.Join(string(env.cfg), "session")
+		_, err := os.Stat(sessionFile)
+		require.NoError(t, err, "session file should exist due to automatic fallback to file storage")
+
+		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("LogoutWithDefaultKeyring", func(t *testing.T) {
+		t.Parallel()
+
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+		pty := ptytest.New(t)
+
+		// First login to create a session (will use file storage due to automatic fallback)
+		env := setupKeyringTestEnv(t, client.URL.String(),
+			"login",
+			"--force-tty",
+			"--no-open",
+			client.URL.String(),
+		)
+		loginInv := env.inv
+		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
+
+		// Verify session file exists
+		sessionFile := path.Join(string(env.cfg), "session")
+		_, err := os.Stat(sessionFile)
+		require.NoError(t, err, "session file should exist before logout")
+
+		// Now logout - should succeed and delete the file
+		logoutEnv := setupKeyringTestEnv(t, client.URL.String(),
+			"logout",
+			"--yes",
+			"--global-config", string(env.cfg),
+		)
+
+		err = logoutEnv.inv.Run()
+		require.NoError(t, err, "logout should succeed with automatic file storage fallback")
+
+		_, err = os.Stat(sessionFile)
+		require.True(t, os.IsNotExist(err), "session file should be deleted after logout")
+	})
+}
@@ -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 the operating system keyring on " +
+			"macOS and Windows and a plain text file on Linux. Use the --use-keyring flag " +
+			"or CODER_USE_KEYRING environment variable to change the storage mechanism.",
 		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())
@@ -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()
@@ -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; omit --use-keyring 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
@@ -99,6 +104,7 @@ func (r *RootCmd) CoreSubcommands() []*serpent.Command {
 		r.resetPassword(),
 		r.sharing(),
 		r.state(),
+		r.tasksCommand(),
 		r.templates(),
 		r.tokens(),
 		r.users(),
@@ -144,7 +150,7 @@ func (r *RootCmd) AGPLExperimental() []*serpent.Command {
 		r.mcpCommand(),
 		r.promptExample(),
 		r.rptyCommand(),
-		r.tasksCommand(),
+		r.syncCommand(),
 		r.boundary(),
 	}
 }
@@ -474,6 +480,17 @@ 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. This flag is ignored and file-based storage is used when " +
+				"--global-config is set or keyring usage is not supported on the current " +
+				"platform. Set to false to force file-based storage on supported platforms.",
+			Default: "true",
+			Value:   serpent.BoolOf(&r.useKeyring),
+			Group:   globalGroup,
+		},
 		{
 			Flag:        "debug-http",
 			Description: "Debug codersdk HTTP requests.",
@@ -508,6 +525,7 @@ 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
@@ -519,9 +537,12 @@ type RootCmd struct {
 	disableDirect bool
 	debugHTTP     bool

-	disableNetworkTelemetry bool
-	noVersionCheck          bool
-	noFeatureWarning        bool
+	disableNetworkTelemetry    bool
+	noVersionCheck             bool
+	noFeatureWarning           bool
+	useKeyring                 bool
+	keyringServiceName         string
+	useKeyringWithGlobalConfig bool
 }

 // InitClient creates and configures a new client with authentication, telemetry,
@@ -549,14 +570,19 @@ 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 +614,6 @@ 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 +630,19 @@ 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 +718,45 @@ 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 {
+		// Checking for the --global-config directory being set is a bit wonky but necessary
+		// to allow extensions that invoke the CLI with this flag (e.g. VS code) to continue
+		// working without modification. In the future we should modify these extensions to
+		// either access the credential in the keyring (like Coder Desktop) or some other
+		// approach that doesn't rely on the session token being stored on disk.
+		assumeExtensionInUse := r.globalConfig != config.DefaultDir() && !r.useKeyringWithGlobalConfig
+		keyringSupported := runtime.GOOS == "windows" || runtime.GOOS == "darwin"
+		if r.useKeyring && !assumeExtensionInUse && keyringSupported {
+			serviceName := sessionstore.DefaultServiceName
+			if r.keyringServiceName != "" {
+				serviceName = r.keyringServiceName
+			}
+			r.tokenBackend = sessionstore.NewKeyringWithService(serviceName)
+		} else {
+			r.tokenBackend = sessionstore.NewFile(r.createConfig)
+		}
+	}
+	return r.tokenBackend
+}
+
+// WithKeyringServiceName sets a custom keyring service name for testing purposes.
+// This allows tests to use isolated keyring storage while still exercising the
+// genuine storage backend selection logic in ensureTokenBackend().
+func (r *RootCmd) WithKeyringServiceName(serviceName string) {
+	r.keyringServiceName = serviceName
+}
+
+// UseKeyringWithGlobalConfig enables the use of the keyring storage backend
+// when the --global-config directory is set. This is only intended as an override
+// for tests, which require specifying the global config directory for test isolation.
+func (r *RootCmd) UseKeyringWithGlobalConfig() {
+	r.useKeyringWithGlobalConfig = true
+}
+
 type AgentAuth struct {
 	// Agent Client config
 	agentToken     string
@@ -72,6 +72,31 @@ func TestCommandHelp(t *testing.T) {
 			Name: "coder provisioner jobs list --output json",
 			Cmd:  []string{"provisioner", "jobs", "list", "--output", "json"},
 		},
+		// TODO (SasSwart): Remove these once the sync commands are promoted out of experimental.
+		clitest.CommandHelpCase{
+			Name: "coder exp sync --help",
+			Cmd:  []string{"exp", "sync", "--help"},
+		},
+		clitest.CommandHelpCase{
+			Name: "coder exp sync ping --help",
+			Cmd:  []string{"exp", "sync", "ping", "--help"},
+		},
+		clitest.CommandHelpCase{
+			Name: "coder exp sync start --help",
+			Cmd:  []string{"exp", "sync", "start", "--help"},
+		},
+		clitest.CommandHelpCase{
+			Name: "coder exp sync want --help",
+			Cmd:  []string{"exp", "sync", "want", "--help"},
+		},
+		clitest.CommandHelpCase{
+			Name: "coder exp sync complete --help",
+			Cmd:  []string{"exp", "sync", "complete", "--help"},
+		},
+		clitest.CommandHelpCase{
+			Name: "coder exp sync status --help",
+			Cmd:  []string{"exp", "sync", "status", "--help"},
+		},
 	))
 }

@@ -176,6 +176,22 @@ func (r *RootCmd) scheduleStart() *serpent.Command {
 				}

 				schedStr = ptr.Ref(sched.String())
+
+				// Check if the template has autostart requirements that may conflict
+				// with the user's schedule.
+				template, err := client.Template(inv.Context(), workspace.TemplateID)
+				if err != nil {
+					return xerrors.Errorf("get template: %w", err)
+				}
+
+				if len(template.AutostartRequirement.DaysOfWeek) > 0 {
+					_, _ = fmt.Fprintf(
+						inv.Stderr,
+						"Warning: your workspace template restricts autostart to the following days: %s.\n"+
+							"Your workspace may only autostart on these days.\n",
+						strings.Join(template.AutostartRequirement.DaysOfWeek, ", "),
+					)
+				}
 			}

 			err = client.UpdateWorkspaceAutostart(inv.Context(), workspace.ID, codersdk.UpdateWorkspaceAutostartRequest{
@@ -373,3 +373,67 @@ func TestScheduleOverride(t *testing.T) {
 		})
 	}
 }
+
+//nolint:paralleltest // t.Setenv
+func TestScheduleStart_TemplateAutostartRequirement(t *testing.T) {
+	t.Setenv("TZ", "UTC")
+	loc, err := tz.TimezoneIANA()
+	require.NoError(t, err)
+	require.Equal(t, "UTC", loc.String())
+
+	client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
+	user := coderdtest.CreateFirstUser(t, client)
+
+	version := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, nil)
+	coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
+	template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID)
+
+	// Update template to have autostart requirement
+	// Note: In AGPL, this will be ignored and all days will be allowed (enterprise feature).
+	template, err = client.UpdateTemplateMeta(context.Background(), template.ID, codersdk.UpdateTemplateMeta{
+		AutostartRequirement: &codersdk.TemplateAutostartRequirement{
+			DaysOfWeek: []string{"monday", "wednesday", "friday"},
+		},
+	})
+	require.NoError(t, err)
+
+	// Verify the template - in AGPL, AutostartRequirement will have all days (enterprise feature)
+	template, err = client.Template(context.Background(), template.ID)
+	require.NoError(t, err)
+	require.NotEmpty(t, template.AutostartRequirement.DaysOfWeek, "template should have autostart requirement days")
+
+	workspace := coderdtest.CreateWorkspace(t, client, template.ID)
+	coderdtest.AwaitWorkspaceBuildJobCompleted(t, client, workspace.LatestBuild.ID)
+
+	t.Run("ShowsWarning", func(t *testing.T) {
+		// When: user sets autostart schedule
+		inv, root := clitest.New(t,
+			"schedule", "start", workspace.Name, "9:30AM", "Mon-Fri",
+		)
+		clitest.SetupConfig(t, client, root)
+		pty := ptytest.New(t).Attach(inv)
+		require.NoError(t, inv.Run())
+
+		// Then: warning should be shown
+		// In AGPL, this will show all days (enterprise feature defaults to all days allowed)
+		pty.ExpectMatch("Warning")
+		pty.ExpectMatch("may only autostart")
+	})
+
+	t.Run("NoWarningWhenManual", func(t *testing.T) {
+		// When: user sets manual schedule
+		inv, root := clitest.New(t,
+			"schedule", "start", workspace.Name, "manual",
+		)
+		clitest.SetupConfig(t, client, root)
+
+		var stderrBuf bytes.Buffer
+		inv.Stderr = &stderrBuf
+
+		require.NoError(t, inv.Run())
+
+		// Then: no warning should be shown on stderr
+		stderrOutput := stderrBuf.String()
+		require.NotContains(t, stderrOutput, "Warning")
+	})
+}
@@ -29,6 +29,7 @@ import (
 	"strings"
 	"sync"
 	"sync/atomic"
+	"testing"
 	"time"

 	"github.com/charmbracelet/lipgloss"
@@ -1028,7 +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
@@ -1377,6 +1378,7 @@ func IsLocalURL(ctx context.Context, u *url.URL) (bool, error) {
 }

 func shutdownWithTimeout(shutdown func(context.Context) error, timeout time.Duration) error {
+	// nolint:gocritic // The magic number is parameterized.
 	ctx, cancel := context.WithTimeout(context.Background(), timeout)
 	defer cancel()
 	return shutdown(ctx)
@@ -1474,6 +1476,7 @@ func newProvisionerDaemon(
 						Listener:      terraformServer,
 						Logger:        provisionerLogger,
 						WorkDirectory: workDir,
+						Experiments:   coderAPI.Experiments,
 					},
 					CachePath: tfDir,
 					Tracer:    tracer,
@@ -2134,50 +2137,90 @@ func startBuiltinPostgres(ctx context.Context, cfg config.Root, logger slog.Logg
 		return "", nil, xerrors.New("The built-in PostgreSQL cannot run as the root user. Create a non-root user and run again!")
 	}

-	// Ensure a password and port have been generated!
-	connectionURL, err := embeddedPostgresURL(cfg)
-	if err != nil {
-		return "", nil, err
-	}
-	pgPassword, err := cfg.PostgresPassword().Read()
-	if err != nil {
-		return "", nil, xerrors.Errorf("read postgres password: %w", err)
-	}
-	pgPortRaw, err := cfg.PostgresPort().Read()
-	if err != nil {
-		return "", nil, xerrors.Errorf("read postgres port: %w", err)
-	}
-	pgPort, err := strconv.ParseUint(pgPortRaw, 10, 16)
-	if err != nil {
-		return "", nil, xerrors.Errorf("parse postgres port: %w", err)
-	}
-
 	cachePath := filepath.Join(cfg.PostgresPath(), "cache")
 	if customCacheDir != "" {
 		cachePath = filepath.Join(customCacheDir, "postgres")
 	}
 	stdlibLogger := slog.Stdlib(ctx, logger.Named("postgres"), slog.LevelDebug)
-	ep := embeddedpostgres.NewDatabase(
-		embeddedpostgres.DefaultConfig().
-			Version(embeddedpostgres.V13).
-			BinariesPath(filepath.Join(cfg.PostgresPath(), "bin")).
-			// Default BinaryRepositoryURL repo1.maven.org is flaky.
-			BinaryRepositoryURL("https://repo.maven.apache.org/maven2").
-			DataPath(filepath.Join(cfg.PostgresPath(), "data")).
-			RuntimePath(filepath.Join(cfg.PostgresPath(), "runtime")).
-			CachePath(cachePath).
-			Username("coder").
-			Password(pgPassword).
-			Database("coder").
-			Encoding("UTF8").
-			Port(uint32(pgPort)).
-			Logger(stdlibLogger.Writer()),
-	)
-	err = ep.Start()
-	if err != nil {
-		return "", nil, xerrors.Errorf("Failed to start built-in PostgreSQL. Optionally, specify an external deployment with `--postgres-url`: %w", err)
+
+	// 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 {
+		maxAttempts = 3
 	}
-	return connectionURL, ep.Stop, nil
+
+	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 {
+			return "", nil, err
+		}
+		pgPassword, err := cfg.PostgresPassword().Read()
+		if err != nil {
+			return "", nil, xerrors.Errorf("read postgres password: %w", err)
+		}
+		pgPortRaw, err := cfg.PostgresPort().Read()
+		if err != nil {
+			return "", nil, xerrors.Errorf("read postgres port: %w", err)
+		}
+		pgPort, err := strconv.ParseUint(pgPortRaw, 10, 16)
+		if err != nil {
+			return "", nil, xerrors.Errorf("parse postgres port: %w", err)
+		}
+
+		ep := embeddedpostgres.NewDatabase(
+			embeddedpostgres.DefaultConfig().
+				Version(embeddedpostgres.V13).
+				BinariesPath(filepath.Join(cfg.PostgresPath(), "bin")).
+				// Default BinaryRepositoryURL repo1.maven.org is flaky.
+				BinaryRepositoryURL("https://repo.maven.apache.org/maven2").
+				DataPath(filepath.Join(cfg.PostgresPath(), "data")).
+				RuntimePath(filepath.Join(cfg.PostgresPath(), "runtime")).
+				CachePath(cachePath).
+				Username("coder").
+				Password(pgPassword).
+				Database("coder").
+				Encoding("UTF8").
+				Port(uint32(pgPort)).
+				Logger(stdlibLogger.Writer()),
+		)
+
+		startErr = ep.Start()
+		if startErr == nil {
+			return connectionURL, ep.Stop, nil
+		}
+
+		logger.Warn(ctx, "failed to start embedded postgres",
+			slog.F("attempt", attempt+1),
+			slog.F("max_attempts", maxAttempts),
+			slog.F("port", pgPort),
+			slog.Error(startErr),
+		)
+	}
+
+	return "", nil, xerrors.Errorf("failed to start built-in PostgreSQL after %d attempts. "+
+		"Optionally, specify an external deployment. See https://coder.com/docs/tutorials/external-database "+
+		"for more details: %w", maxAttempts, startErr)
 }

 func ConfigureHTTPClient(ctx context.Context, clientCertFile, clientKeyFile string, tlsClientCAFile string) (context.Context, *http.Client, error) {
@@ -2286,7 +2329,7 @@ func ConnectToPostgres(ctx context.Context, logger slog.Logger, driver string, d
 	var err error
 	var sqlDB *sql.DB
 	dbNeedsClosing := true
-	// Try to connect for 30 seconds.
+	// nolint:gocritic // Try to connect for 30 seconds.
 	ctx, cancel := context.WithTimeout(ctx, 30*time.Second)
 	defer cancel()

@@ -2382,6 +2425,7 @@ func ConnectToPostgres(ctx context.Context, logger slog.Logger, driver string, d
 }

 func pingPostgres(ctx context.Context, db *sql.DB) error {
+	// nolint:gocritic // This is a reasonable magic number for a ping timeout.
 	ctx, cancel := context.WithTimeout(ctx, 5*time.Second)
 	defer cancel()
 	return db.PingContext(ctx)
@@ -17,9 +17,6 @@ import (

 func TestRegenerateVapidKeypair(t *testing.T) {
 	t.Parallel()
-	if !dbtestutil.WillUsePostgres() {
-		t.Skip("this test is only supported on postgres")
-	}

 	t.Run("NoExistingVAPIDKeys", func(t *testing.T) {
 		t.Parallel()
@@ -348,9 +348,6 @@ func TestServer(t *testing.T) {

 		runGitHubProviderTest := func(t *testing.T, tc testCase) {
 			t.Parallel()
-			if !dbtestutil.WillUsePostgres() {
-				t.Skip("test requires postgres")
-			}

 			ctx, cancelFunc := context.WithCancel(testutil.Context(t, testutil.WaitLong))
 			defer cancelFunc()
@@ -2142,10 +2139,6 @@ func TestServerYAMLConfig(t *testing.T) {
 func TestConnectToPostgres(t *testing.T) {
 	t.Parallel()

-	if !dbtestutil.WillUsePostgres() {
-		t.Skip("this test does not make sense without postgres")
-	}
-
 	t.Run("Migrate", func(t *testing.T) {
 		t.Parallel()

@@ -2256,10 +2249,6 @@ type runServerOpts struct {
 func TestServer_TelemetryDisabled_FinalReport(t *testing.T) {
 	t.Parallel()

-	if !dbtestutil.WillUsePostgres() {
-		t.Skip("this test requires postgres")
-	}
-
 	telemetryServerURL, deployment, snapshot := mockTelemetryServer(t)
 	dbConnURL, err := dbtestutil.Open(t)
 	require.NoError(t, err)
@@ -0,0 +1,237 @@
+// 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
+}
+
+// NewKeyringWithService creates a Keyring Backend that stores credentials under the
+// specified service name. Generally, DefaultServiceName should be provided as the service
+// name except in tests which may need parameterization to avoid conflicting keyring use.
+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()
+}
@@ -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
+}
@@ -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]
+}
@@ -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)
+}
@@ -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
+}
@@ -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
+}
@@ -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)
+	})
+}
@@ -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()
+}
@@ -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)
+}
@@ -54,6 +54,7 @@ func TestSharingShare(t *testing.T) {
 			MinimalUser: codersdk.MinimalUser{
 				ID:        toShareWithUser.ID,
 				Username:  toShareWithUser.Username,
+				Name:      toShareWithUser.Name,
 				AvatarURL: toShareWithUser.AvatarURL,
 			},
 			Role: codersdk.WorkspaceRole("use"),
@@ -103,6 +104,7 @@ func TestSharingShare(t *testing.T) {
 			MinimalUser: codersdk.MinimalUser{
 				ID:        toShareWithUser1.ID,
 				Username:  toShareWithUser1.Username,
+				Name:      toShareWithUser1.Name,
 				AvatarURL: toShareWithUser1.AvatarURL,
 			},
 			Role: codersdk.WorkspaceRoleUse,
@@ -111,6 +113,7 @@ func TestSharingShare(t *testing.T) {
 			MinimalUser: codersdk.MinimalUser{
 				ID:        toShareWithUser2.ID,
 				Username:  toShareWithUser2.Username,
+				Name:      toShareWithUser2.Name,
 				AvatarURL: toShareWithUser2.AvatarURL,
 			},
 			Role: codersdk.WorkspaceRoleUse,
@@ -155,6 +158,7 @@ func TestSharingShare(t *testing.T) {
 			MinimalUser: codersdk.MinimalUser{
 				ID:        toShareWithUser.ID,
 				Username:  toShareWithUser.Username,
+				Name:      toShareWithUser.Name,
 				AvatarURL: toShareWithUser.AvatarURL,
 			},
 			Role: codersdk.WorkspaceRoleAdmin,
@@ -109,6 +109,51 @@ func (r *RootCmd) ssh() *serpent.Command {
 				}
 			},
 		),
+		CompletionHandler: func(inv *serpent.Invocation) []string {
+			client, err := r.InitClient(inv)
+			if err != nil {
+				return []string{}
+			}
+
+			res, err := client.Workspaces(inv.Context(), codersdk.WorkspaceFilter{
+				Owner: codersdk.Me,
+			})
+			if err != nil {
+				return []string{}
+			}
+
+			var mu sync.Mutex
+			var completions []string
+			var wg sync.WaitGroup
+			for _, ws := range res.Workspaces {
+				wg.Add(1)
+				go func() {
+					defer wg.Done()
+					resources, err := client.TemplateVersionResources(inv.Context(), ws.LatestBuild.TemplateVersionID)
+					if err != nil {
+						return
+					}
+					var agents []codersdk.WorkspaceAgent
+					for _, resource := range resources {
+						agents = append(agents, resource.Agents...)
+					}
+
+					mu.Lock()
+					defer mu.Unlock()
+					if len(agents) == 1 {
+						completions = append(completions, ws.Name)
+					} else {
+						for _, agent := range agents {
+							completions = append(completions, fmt.Sprintf("%s.%s", ws.Name, agent.Name))
+						}
+					}
+				}()
+			}
+			wg.Wait()
+
+			slices.Sort(completions)
+			return completions
+		},
 		Handler: func(inv *serpent.Invocation) (retErr error) {
 			client, err := r.InitClient(inv)
 			if err != nil {
@@ -906,6 +951,8 @@ func GetWorkspaceAndAgent(ctx context.Context, inv *serpent.Invocation, client *
 					return codersdk.Workspace{}, codersdk.WorkspaceAgent{}, nil, xerrors.Errorf("start workspace with active template version: %w", err)
 				}
 				_, _ = fmt.Fprintln(inv.Stdout, "Unable to start the workspace with template version from last build. Your workspace has been updated to the current active template version.")
+			default:
+				return codersdk.Workspace{}, codersdk.WorkspaceAgent{}, nil, xerrors.Errorf("start workspace with current template version: %w", err)
 			}
 		} else if err != nil {
 			return codersdk.Workspace{}, codersdk.WorkspaceAgent{}, nil, xerrors.Errorf("start workspace with current template version: %w", err)
@@ -2447,3 +2447,99 @@ func tempDirUnixSocket(t *testing.T) string {

 	return t.TempDir()
 }
+
+func TestSSH_Completion(t *testing.T) {
+	t.Parallel()
+
+	t.Run("SingleAgent", func(t *testing.T) {
+		t.Parallel()
+
+		client, workspace, agentToken := setupWorkspaceForAgent(t)
+		_ = agenttest.New(t, client.URL, agentToken)
+		coderdtest.AwaitWorkspaceAgents(t, client, workspace.ID)
+
+		var stdout bytes.Buffer
+		inv, root := clitest.New(t, "ssh", "")
+		inv.Stdout = &stdout
+		inv.Environ.Set("COMPLETION_MODE", "1")
+		clitest.SetupConfig(t, client, root)
+
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitMedium)
+		defer cancel()
+
+		err := inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		// For single-agent workspaces, the only completion should be the
+		// bare workspace name.
+		output := stdout.String()
+		t.Logf("Completion output: %q", output)
+		require.Contains(t, output, workspace.Name)
+	})
+
+	t.Run("MultiAgent", func(t *testing.T) {
+		t.Parallel()
+
+		client, store := coderdtest.NewWithDatabase(t, nil)
+		first := coderdtest.CreateFirstUser(t, client)
+		userClient, user := coderdtest.CreateAnotherUserMutators(t, client, first.OrganizationID, nil, func(r *codersdk.CreateUserRequestWithOrgs) {
+			r.Username = "multiuser"
+		})
+
+		r := dbfake.WorkspaceBuild(t, store, database.WorkspaceTable{
+			Name:           "multiworkspace",
+			OrganizationID: first.OrganizationID,
+			OwnerID:        user.ID,
+		}).WithAgent(func(agents []*proto.Agent) []*proto.Agent {
+			return []*proto.Agent{
+				{
+					Name: "agent1",
+					Auth: &proto.Agent_Token{},
+				},
+				{
+					Name: "agent2",
+					Auth: &proto.Agent_Token{},
+				},
+			}
+		}).Do()
+
+		var stdout bytes.Buffer
+		inv, root := clitest.New(t, "ssh", "")
+		inv.Stdout = &stdout
+		inv.Environ.Set("COMPLETION_MODE", "1")
+		clitest.SetupConfig(t, userClient, root)
+
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitMedium)
+		defer cancel()
+
+		err := inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		// For multi-agent workspaces, completions should include the
+		// workspace.agent format but NOT the bare workspace name.
+		output := stdout.String()
+		t.Logf("Completion output: %q", output)
+		lines := strings.Split(strings.TrimSpace(output), "\n")
+		require.NotContains(t, lines, r.Workspace.Name)
+		require.Contains(t, output, r.Workspace.Name+".agent1")
+		require.Contains(t, output, r.Workspace.Name+".agent2")
+	})
+
+	t.Run("NetworkError", func(t *testing.T) {
+		t.Parallel()
+
+		var stdout bytes.Buffer
+		inv, _ := clitest.New(t, "ssh", "")
+		inv.Stdout = &stdout
+		inv.Environ.Set("COMPLETION_MODE", "1")
+
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
+		defer cancel()
+
+		err := inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		output := stdout.String()
+		require.Empty(t, output)
+	})
+}
@@ -0,0 +1,35 @@
+package cli
+
+import (
+	"github.com/coder/serpent"
+)
+
+func (r *RootCmd) syncCommand() *serpent.Command {
+	var socketPath string
+
+	cmd := &serpent.Command{
+		Use:   "sync",
+		Short: "Manage unit dependencies for coordinated startup",
+		Long:  "Commands for orchestrating unit startup order in workspaces. Units are most commonly coder scripts. Use these commands to declare dependencies between units, coordinate their startup sequence, and ensure units start only after their dependencies are ready. This helps prevent race conditions and startup failures.",
+		Handler: func(i *serpent.Invocation) error {
+			return i.Command.HelpHandler(i)
+		},
+		Children: []*serpent.Command{
+			r.syncPing(&socketPath),
+			r.syncStart(&socketPath),
+			r.syncWant(&socketPath),
+			r.syncComplete(&socketPath),
+			r.syncStatus(&socketPath),
+		},
+		Options: serpent.OptionSet{
+			{
+				Flag:        "socket-path",
+				Env:         "CODER_AGENT_SOCKET_PATH",
+				Description: "Specify the path for the agent socket.",
+				Value:       serpent.StringOf(&socketPath),
+			},
+		},
+	}
+
+	return cmd
+}
@@ -0,0 +1,47 @@
+package cli
+
+import (
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/agent/agentsocket"
+	"github.com/coder/coder/v2/agent/unit"
+	"github.com/coder/coder/v2/cli/cliui"
+	"github.com/coder/serpent"
+)
+
+func (*RootCmd) syncComplete(socketPath *string) *serpent.Command {
+	cmd := &serpent.Command{
+		Use:   "complete <unit>",
+		Short: "Mark a unit as complete",
+		Long:  "Mark a unit as complete. Indicating to other units that it has completed its work. This allows units that depend on it to proceed with their startup.",
+		Handler: func(i *serpent.Invocation) error {
+			ctx := i.Context()
+
+			if len(i.Args) != 1 {
+				return xerrors.New("exactly one unit name is required")
+			}
+			unit := unit.ID(i.Args[0])
+
+			opts := []agentsocket.Option{}
+			if *socketPath != "" {
+				opts = append(opts, agentsocket.WithPath(*socketPath))
+			}
+
+			client, err := agentsocket.NewClient(ctx, opts...)
+			if err != nil {
+				return xerrors.Errorf("connect to agent socket: %w", err)
+			}
+			defer client.Close()
+
+			if err := client.SyncComplete(ctx, unit); err != nil {
+				return xerrors.Errorf("complete unit failed: %w", err)
+			}
+
+			cliui.Info(i.Stdout, "Success")
+
+			return nil
+		},
+	}
+
+	return cmd
+}
--- a/Show More
+++ b/Show More