chore: switch agent gone response from 502 to 404 (backport #23090 ) (#23634 )

Backport of #23090 to `release/2.29`. When a user creates a workspace, opens the web terminal, then the workspace stops but the web terminal remains open, the web terminal will retry the connection. Coder would issue a HTTP 502 Bad Gateway response when this occurred because coderd could not connect to the workspace agent, however this is problematic as any load balancer sitting in front of Coder sees a 502 and thinks Coder is unhealthy. This PR changes the response to a HTTP 404 after internal discussion. Cherry-picked from merge commit c33812a430. The conflict in `coderd/workspaceapps/errors.go` was resolved by applying the status code change (502 → 404) while keeping the existing `RetryEnabled`/`DashboardURL` fields (the `Actions` refactor is not on this branch).
fix: prevent ui error when last org member is removed (#23017 )
2026-03-25 16:49:51 -04:00 · 2026-03-25 15:47:37 -04:00 · 2026-03-25 15:46:57 -04:00 · 2026-03-25 15:31:12 -04:00 · 2026-03-03 13:25:55 -05:00 · 2026-03-03 12:24:44 +01:00
368 changed files with 14156 additions and 10419 deletions
@@ -27,7 +27,7 @@ ignorePatterns:
  - pattern: "splunk.com"
  - pattern: "stackoverflow.com/questions"
  - pattern: "developer.hashicorp.com/terraform/language"
-  - pattern: "platform.openai.com/docs/api-reference"
+  - pattern: "platform.openai.com"
  - pattern: "api.openai.com"
 aliveStatusCodes:
  - 200
@@ -11,4 +11,4 @@ runs:
          go install storj.io/drpc/cmd/protoc-gen-go-drpc@v0.0.34
          go install golang.org/x/tools/cmd/goimports@v0.31.0
          go install github.com/mikefarah/yq/v4@v4.44.3
-          go install go.uber.org/mock/mockgen@v0.5.0
+          go install go.uber.org/mock/mockgen@v0.6.0
@@ -4,7 +4,7 @@ description: |
 inputs:
  version:
    description: "The Go version to use."
-    default: "1.24.10"
+    default: "1.25.6"
  use-preinstalled-go:
    description: "Whether to use preinstalled Go."
    default: "false"
@@ -7,5 +7,5 @@ runs:
    - name: Install Terraform
      uses: hashicorp/setup-terraform@b9cd54a3c349d3f38e8881555d616ced269862dd # v3.1.2
      with:
-        terraform_version: 1.13.4
+        terraform_version: 1.14.5
        terraform_wrapper: false
@@ -35,7 +35,7 @@ jobs:
      tailnet-integration: ${{ steps.filter.outputs.tailnet-integration }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        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@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -235,7 +235,7 @@ jobs:
    if: ${{ !cancelled() }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -292,7 +292,7 @@ jobs:
    timeout-minutes: 20
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -343,7 +343,7 @@ jobs:
          - windows-2022
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -532,7 +532,7 @@ jobs:
    timeout-minutes: 25
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -581,7 +581,7 @@ jobs:
    timeout-minutes: 25
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -641,7 +641,7 @@ jobs:
    timeout-minutes: 20
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -668,7 +668,7 @@ jobs:
    timeout-minutes: 20
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -701,7 +701,7 @@ jobs:
    name: ${{ matrix.variant.name }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -781,7 +781,7 @@ jobs:
    if: needs.changes.outputs.site == 'true' || needs.changes.outputs.ci == 'true'
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -862,7 +862,7 @@ jobs:

    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -933,7 +933,7 @@ jobs:
    if: always()
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -1053,7 +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@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -1108,7 +1108,7 @@ jobs:
      IMAGE: ghcr.io/coder/coder-preview:${{ steps.build-docker.outputs.tag }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -1505,7 +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@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -36,7 +36,7 @@ jobs:
      verdict: ${{ steps.check.outputs.verdict }} # DEPLOY or NOOP
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        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@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -146,7 +146,7 @@ jobs:
    needs: deploy
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -38,7 +38,7 @@ jobs:
    if: github.repository_owner == 'coder'
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -26,7 +26,7 @@ jobs:
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-4' || 'ubuntu-latest' }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -125,7 +125,7 @@ jobs:
      id-token: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -27,7 +27,7 @@ jobs:
          - windows-2022
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -15,7 +15,7 @@ jobs:
    runs-on: ubuntu-latest
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -19,7 +19,7 @@ jobs:
      packages: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        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@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -76,7 +76,7 @@ jobs:
    runs-on: "ubuntu-latest"
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -184,7 +184,7 @@ jobs:
      pull-requests: write # needed for commenting on PRs
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -228,7 +228,7 @@ jobs:
      CODER_IMAGE_TAG: ${{ needs.get_info.outputs.CODER_IMAGE_TAG }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -288,7 +288,7 @@ jobs:
      PR_HOSTNAME: "pr${{ needs.get_info.outputs.PR_NUMBER }}.${{ secrets.PR_DEPLOYMENTS_DOMAIN }}"
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

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

    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -164,7 +164,7 @@ jobs:
      version: ${{ steps.version.outputs.version }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -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@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

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

    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -971,7 +971,7 @@ jobs:
    if: ${{ !inputs.dry_run }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

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

    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -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@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -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@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -97,7 +97,7 @@ jobs:
      - name: Install yq
        run: go run github.com/mikefarah/yq/v4@v4.44.3
      - name: Install mockgen
-        run: go install go.uber.org/mock/mockgen@v0.5.0
+        run: go install go.uber.org/mock/mockgen@v0.6.0
      - name: Install protoc-gen-go
        run: go install google.golang.org/protobuf/cmd/protoc-gen-go@v1.30
      - name: Install protoc-gen-go-drpc
@@ -146,7 +146,7 @@ jobs:
          echo "image=$(cat "$image_job")" >> "$GITHUB_OUTPUT"

      - name: Run Trivy vulnerability scanner
-        uses: aquasecurity/trivy-action@b6643a29fecd7f34b3597bc6acb0a98b03d33ff8
+        uses: aquasecurity/trivy-action@c1824fd6edce30d7ab345a9989de00bbd46ef284 # v0.34.0
        with:
          image-ref: ${{ steps.build.outputs.image }}
          format: sarif
@@ -18,7 +18,7 @@ jobs:
      pull-requests: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -96,7 +96,7 @@ jobs:
      contents: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -120,7 +120,7 @@ jobs:
      actions: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -21,7 +21,7 @@ jobs:
      pull-requests: write # required to post PR review comments by the action
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
+        uses: step-security/harden-runner@58077d3c7e43986b6b15fba718e8ea69e387dfcc # v2.16.0
        with:
          egress-policy: audit

@@ -27,3 +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
@@ -69,6 +69,9 @@ MOST_GO_SRC_FILES := $(shell \
 # All the shell files in the repo, excluding ignored files.
 SHELL_SRC_FILES := $(shell find . $(FIND_EXCLUSIONS) -type f -name '*.sh')

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

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

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

 lint/site-icons:
@@ -608,7 +611,9 @@ lint/actions/actionlint:
 .PHONY: lint/actions/actionlint

 lint/actions/zizmor:
-	./scripts/zizmor.sh \
+	# Using a token will use trivy, which is no longer supported.
+	# So disable any use of a token for this target.
+	GH_TOKEN="" ./scripts/zizmor.sh \
 		--strict-collection \
 		--persona=regular \
 		.
@@ -619,6 +624,12 @@ lint/check-scopes: coderd/database/dump.sql
 	go run ./scripts/check-scopes
 .PHONY: lint/check-scopes

+# Verify migrations do not hardcode the public schema.
+lint/migrations:
+	./scripts/check_pg_schema.sh "Migrations" $(MIGRATION_FILES)
+	./scripts/check_pg_schema.sh "Fixtures" $(FIXTURE_FILES)
+.PHONY: lint/migrations
+
 # All files generated by the database should be added here, and this can be used
 # as a target for jobs that need to run after the database is generated.
 DB_GEN_FILES := \
@@ -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))
 	}
@@ -0,0 +1,149 @@
+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),
+	})
+	if err != nil {
+		return false, xerrors.Errorf("sync ready: %w", err)
+	}
+	return resp.Ready, nil
+}
+
+// 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"`
+}
@@ -7,8 +7,6 @@ import (
 	"sync"

 	"golang.org/x/xerrors"
-
-	"github.com/hashicorp/yamux"
 	"storj.io/drpc/drpcmux"
 	"storj.io/drpc/drpcserver"

@@ -33,11 +31,17 @@ type Server struct {
 	wg       sync.WaitGroup
 }

-func NewServer(path string, logger slog.Logger) (*Server, error) {
+// 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:   path,
+		path:   options.path,
 		service: &DRPCAgentSocketService{
 			logger:      logger,
 			unitManager: unit.NewManager(),
@@ -61,14 +65,6 @@ func NewServer(path string, logger slog.Logger) (*Server, error) {
 		},
 	})

-	if server.path == "" {
-		var err error
-		server.path, err = getDefaultSocketPath()
-		if err != nil {
-			return nil, xerrors.Errorf("get default socket path: %w", err)
-		}
-	}
-
 	listener, err := createSocket(server.path)
 	if err != nil {
 		return nil, xerrors.Errorf("create socket: %w", err)
@@ -91,6 +87,7 @@ func NewServer(path string, logger slog.Logger) (*Server, error) {
 	return server, nil
 }

+// Close stops the server and cleans up resources.
 func (s *Server) Close() error {
 	s.mu.Lock()

@@ -134,52 +131,8 @@ func (s *Server) acceptConnections() {
 		return
 	}

-	for {
-		select {
-		case <-s.ctx.Done():
-			return
-		default:
-		}
-
-		conn, err := listener.Accept()
-		if err != nil {
-			s.logger.Warn(s.ctx, "error accepting connection", slog.Error(err))
-			continue
-		}
-
-		s.mu.Lock()
-		if s.listener == nil {
-			s.mu.Unlock()
-			_ = conn.Close()
-			return
-		}
-		s.wg.Add(1)
-		s.mu.Unlock()
-
-		go func() {
-			defer s.wg.Done()
-			s.handleConnection(conn)
-		}()
-	}
-}
-
-func (s *Server) handleConnection(conn net.Conn) {
-	defer conn.Close()
-
-	s.logger.Debug(s.ctx, "new connection accepted", slog.F("remote_addr", conn.RemoteAddr()))
-
-	config := yamux.DefaultConfig()
-	config.LogOutput = nil
-	config.Logger = slog.Stdlib(s.ctx, s.logger.Named("agentsocket-yamux"), slog.LevelInfo)
-	session, err := yamux.Server(conn, config)
-	if err != nil {
-		s.logger.Warn(s.ctx, "failed to create yamux session", slog.Error(err))
-		return
-	}
-	defer session.Close()
-
-	err = s.drpcServer.Serve(s.ctx, session)
-	if err != nil {
-		s.logger.Debug(s.ctx, "drpc server finished", slog.Error(err))
+	err := s.drpcServer.Serve(s.ctx, listener)
+	if err != nil {
+		s.logger.Warn(s.ctx, "error serving drpc server", slog.Error(err))
 	}
 }
@@ -1,14 +1,24 @@
 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) {
@@ -23,7 +33,7 @@ func TestServer(t *testing.T) {

 		socketPath := filepath.Join(t.TempDir(), "test.sock")
 		logger := slog.Make().Leveled(slog.LevelDebug)
-		server, err := agentsocket.NewServer(socketPath, logger)
+		server, err := agentsocket.NewServer(logger, agentsocket.WithPath(socketPath))
 		require.NoError(t, err)
 		require.NoError(t, server.Close())
 	})
@@ -33,10 +43,10 @@ func TestServer(t *testing.T) {

 		socketPath := filepath.Join(t.TempDir(), "test.sock")
 		logger := slog.Make().Leveled(slog.LevelDebug)
-		server1, err := agentsocket.NewServer(socketPath, logger)
+		server1, err := agentsocket.NewServer(logger, agentsocket.WithPath(socketPath))
 		require.NoError(t, err)
 		defer server1.Close()
-		_, err = agentsocket.NewServer(socketPath, logger)
+		_, err = agentsocket.NewServer(logger, agentsocket.WithPath(socketPath))
 		require.ErrorContains(t, err, "create socket")
 	})

@@ -45,8 +55,84 @@ func TestServer(t *testing.T) {

 		socketPath := filepath.Join(t.TempDir(), "test.sock")
 		logger := slog.Make().Leveled(slog.LevelDebug)
-		server, err := agentsocket.NewServer(socketPath, logger)
+		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")
+}
@@ -15,15 +15,18 @@ 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)
@@ -53,6 +56,7 @@ func (s *DRPCAgentSocketService) SyncStart(_ context.Context, req *proto.SyncSta
 	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)
@@ -72,6 +76,7 @@ func (s *DRPCAgentSocketService) SyncWant(_ context.Context, req *proto.SyncWant
 	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)
@@ -86,6 +91,7 @@ func (s *DRPCAgentSocketService) SyncComplete(_ context.Context, req *proto.Sync
 	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)
@@ -102,6 +108,7 @@ func (s *DRPCAgentSocketService) SyncReady(_ context.Context, req *proto.SyncRea
 	}, 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)
@@ -115,8 +122,11 @@ func (s *DRPCAgentSocketService) SyncStatus(_ context.Context, req *proto.SyncSt
 	}

 	dependencies, err := s.unitManager.GetAllDependencies(unitID)
-	if err != nil {
-		return nil, xerrors.Errorf("failed to get dependencies: %w", err)
+	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
@@ -5,21 +5,18 @@ import (
 	"crypto/sha256"
 	"encoding/hex"
 	"fmt"
-	"net"
 	"os"
 	"path/filepath"
 	"runtime"
 	"testing"

-	"github.com/hashicorp/yamux"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"

 	"cdr.dev/slog"
 	"github.com/coder/coder/v2/agent/agentsocket"
-	"github.com/coder/coder/v2/agent/agentsocket/proto"
 	"github.com/coder/coder/v2/agent/unit"
-	"github.com/coder/coder/v2/codersdk/drpcsdk"
+	"github.com/coder/coder/v2/testutil"
 )

 // tempDirUnixSocket returns a temporary directory that can safely hold unix
@@ -47,23 +44,15 @@ func tempDirUnixSocket(t *testing.T) string {
 }

 // newSocketClient creates a DRPC client connected to the Unix socket at the given path.
-func newSocketClient(t *testing.T, socketPath string) proto.DRPCAgentSocketClient {
+func newSocketClient(ctx context.Context, t *testing.T, socketPath string) *agentsocket.Client {
 	t.Helper()

-	conn, err := net.Dial("unix", socketPath)
-	require.NoError(t, err)
-
-	config := yamux.DefaultConfig()
-	config.Logger = nil
-	session, err := yamux.Client(conn, config)
-	require.NoError(t, err)
-
-	client := proto.NewDRPCAgentSocketClient(drpcsdk.MultiplexedConn(session))
-
+	client, err := agentsocket.NewClient(ctx, agentsocket.WithPath(socketPath))
 	t.Cleanup(func() {
-		_ = session.Close()
-		_ = conn.Close()
+		_ = client.Close()
 	})
+	require.NoError(t, err)
+
 	return client
 }

@@ -78,17 +67,17 @@ func TestDRPCAgentSocketService(t *testing.T) {
 		t.Parallel()

 		socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
-
+		ctx := testutil.Context(t, testutil.WaitShort)
 		server, err := agentsocket.NewServer(
-			socketPath,
 			slog.Make().Leveled(slog.LevelDebug),
+			agentsocket.WithPath(socketPath),
 		)
 		require.NoError(t, err)
 		defer server.Close()

-		client := newSocketClient(t, socketPath)
+		client := newSocketClient(ctx, t, socketPath)

-		_, err = client.Ping(context.Background(), &proto.PingRequest{})
+		err = client.Ping(ctx)
 		require.NoError(t, err)
 	})

@@ -98,147 +87,116 @@ func TestDRPCAgentSocketService(t *testing.T) {
 		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(
-				socketPath,
 				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
 			)
 			require.NoError(t, err)
 			defer server.Close()

-			client := newSocketClient(t, socketPath)
+			client := newSocketClient(ctx, t, socketPath)

-			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
-				Unit: "test-unit",
-			})
+			err = client.SyncStart(ctx, "test-unit")
 			require.NoError(t, err)

-			status, err := client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
-				Unit: "test-unit",
-			})
+			status, err := client.SyncStatus(ctx, "test-unit")
 			require.NoError(t, err)
-			require.Equal(t, "started", status.Status)
+			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(
-				socketPath,
 				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
 			)
 			require.NoError(t, err)
 			defer server.Close()

-			client := newSocketClient(t, socketPath)
+			client := newSocketClient(ctx, t, socketPath)

 			// First Start
-			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
-				Unit: "test-unit",
-			})
+			err = client.SyncStart(ctx, "test-unit")
 			require.NoError(t, err)
-			status, err := client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
-				Unit: "test-unit",
-			})
+			status, err := client.SyncStatus(ctx, "test-unit")
 			require.NoError(t, err)
-			require.Equal(t, "started", status.Status)
+			require.Equal(t, unit.StatusStarted, status.Status)

 			// Second Start
-			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
-				Unit: "test-unit",
-			})
+			err = client.SyncStart(ctx, "test-unit")
 			require.ErrorContains(t, err, unit.ErrSameStatusAlreadySet.Error())

-			status, err = client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
-				Unit: "test-unit",
-			})
+			status, err = client.SyncStatus(ctx, "test-unit")
 			require.NoError(t, err)
-			require.Equal(t, "started", status.Status)
+			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(
-				socketPath,
 				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
 			)
 			require.NoError(t, err)
 			defer server.Close()

-			client := newSocketClient(t, socketPath)
+			client := newSocketClient(ctx, t, socketPath)

 			// First start
-			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
-				Unit: "test-unit",
-			})
+			err = client.SyncStart(ctx, "test-unit")
 			require.NoError(t, err)

-			status, err := client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
-				Unit: "test-unit",
-			})
+			status, err := client.SyncStatus(ctx, "test-unit")
 			require.NoError(t, err)
-			require.Equal(t, "started", status.Status)
+			require.Equal(t, unit.StatusStarted, status.Status)

 			// Complete the unit
-			_, err = client.SyncComplete(context.Background(), &proto.SyncCompleteRequest{
-				Unit: "test-unit",
-			})
+			err = client.SyncComplete(ctx, "test-unit")
 			require.NoError(t, err)

-			status, err = client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
-				Unit: "test-unit",
-			})
+			status, err = client.SyncStatus(ctx, "test-unit")
 			require.NoError(t, err)
-			require.Equal(t, "completed", status.Status)
+			require.Equal(t, unit.StatusComplete, status.Status)

 			// Second start
-			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
-				Unit: "test-unit",
-			})
+			err = client.SyncStart(ctx, "test-unit")
 			require.NoError(t, err)

-			status, err = client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
-				Unit: "test-unit",
-			})
+			status, err = client.SyncStatus(ctx, "test-unit")
 			require.NoError(t, err)
-			require.Equal(t, "started", status.Status)
+			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(
-				socketPath,
 				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
 			)
 			require.NoError(t, err)
 			defer server.Close()

-			client := newSocketClient(t, socketPath)
+			client := newSocketClient(ctx, t, socketPath)

-			_, err = client.SyncWant(context.Background(), &proto.SyncWantRequest{
-				Unit:      "test-unit",
-				DependsOn: "dependency-unit",
-			})
+			err = client.SyncWant(ctx, "test-unit", "dependency-unit")
 			require.NoError(t, err)

-			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
-				Unit: "test-unit",
-			})
+			err = client.SyncStart(ctx, "test-unit")
 			require.ErrorContains(t, err, "unit not ready")

-			status, err := client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
-				Unit: "test-unit",
-			})
+			status, err := client.SyncStatus(ctx, "test-unit")
 			require.NoError(t, err)
-			require.Equal(t, string(unit.StatusPending), status.Status)
+			require.Equal(t, unit.StatusPending, status.Status)
 			require.False(t, status.IsReady)
 		})
 	})
@@ -250,107 +208,86 @@ func TestDRPCAgentSocketService(t *testing.T) {
 			t.Parallel()

 			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
-
+			ctx := testutil.Context(t, testutil.WaitShort)
 			server, err := agentsocket.NewServer(
-				socketPath,
 				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
 			)
 			require.NoError(t, err)
 			defer server.Close()

-			client := newSocketClient(t, socketPath)
+			client := newSocketClient(ctx, t, socketPath)

 			// If dependency units are not registered, they are registered automatically
-			_, err = client.SyncWant(context.Background(), &proto.SyncWantRequest{
-				Unit:      "test-unit",
-				DependsOn: "dependency-unit",
-			})
+			err = client.SyncWant(ctx, "test-unit", "dependency-unit")
 			require.NoError(t, err)

-			status, err := client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
-				Unit: "test-unit",
-			})
+			status, err := client.SyncStatus(ctx, "test-unit")
 			require.NoError(t, err)
 			require.Len(t, status.Dependencies, 1)
-			require.Equal(t, "dependency-unit", status.Dependencies[0].DependsOn)
-			require.Equal(t, "completed", status.Dependencies[0].RequiredStatus)
+			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(
-				socketPath,
 				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
 			)
 			require.NoError(t, err)
 			defer server.Close()

-			client := newSocketClient(t, socketPath)
+			client := newSocketClient(ctx, t, socketPath)

 			// Start the dependency unit
-			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
-				Unit: "dependency-unit",
-			})
+			err = client.SyncStart(ctx, "dependency-unit")
 			require.NoError(t, err)

-			status, err := client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
-				Unit: "dependency-unit",
-			})
+			status, err := client.SyncStatus(ctx, "dependency-unit")
 			require.NoError(t, err)
-			require.Equal(t, "started", status.Status)
+			require.Equal(t, unit.StatusStarted, status.Status)

 			// Add the dependency after the dependency unit has already started
-			_, err = client.SyncWant(context.Background(), &proto.SyncWantRequest{
-				Unit:      "test-unit",
-				DependsOn: "dependency-unit",
-			})
+			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(context.Background(), &proto.SyncStatusRequest{
-				Unit: "test-unit",
-			})
+			status, err = client.SyncStatus(ctx, "test-unit")
 			require.NoError(t, err)
-			require.Equal(t, "dependency-unit", status.Dependencies[0].DependsOn)
-			require.Equal(t, "completed", status.Dependencies[0].RequiredStatus)
+			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(
-				socketPath,
 				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
 			)
 			require.NoError(t, err)
 			defer server.Close()

-			client := newSocketClient(t, socketPath)
+			client := newSocketClient(ctx, t, socketPath)

 			// Start the dependent unit
-			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
-				Unit: "test-unit",
-			})
+			err = client.SyncStart(ctx, "test-unit")
 			require.NoError(t, err)

-			status, err := client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
-				Unit: "test-unit",
-			})
+			status, err := client.SyncStatus(ctx, "test-unit")
 			require.NoError(t, err)
-			require.Equal(t, "started", status.Status)
+			require.Equal(t, unit.StatusStarted, status.Status)

 			// Add the dependency after the dependency unit has already started
-			_, err = client.SyncWant(context.Background(), &proto.SyncWantRequest{
-				Unit:      "test-unit",
-				DependsOn: "dependency-unit",
-			})
+			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.
@@ -359,12 +296,10 @@ func TestDRPCAgentSocketService(t *testing.T) {
 			require.NoError(t, err)

 			// The dependency is now reflected in the test unit's status
-			status, err = client.SyncStatus(context.Background(), &proto.SyncStatusRequest{
-				Unit: "test-unit",
-			})
+			status, err = client.SyncStatus(ctx, "test-unit")
 			require.NoError(t, err)
-			require.Equal(t, "dependency-unit", status.Dependencies[0].DependsOn)
-			require.Equal(t, "completed", status.Dependencies[0].RequiredStatus)
+			require.Equal(t, unit.ID("dependency-unit"), status.Dependencies[0].DependsOn)
+			require.Equal(t, unit.StatusComplete, status.Dependencies[0].RequiredStatus)
 		})
 	})

@@ -375,96 +310,80 @@ func TestDRPCAgentSocketService(t *testing.T) {
 			t.Parallel()

 			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
-
+			ctx := testutil.Context(t, testutil.WaitShort)
 			server, err := agentsocket.NewServer(
-				socketPath,
 				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
 			)
 			require.NoError(t, err)
 			defer server.Close()

-			client := newSocketClient(t, socketPath)
+			client := newSocketClient(ctx, t, socketPath)

-			response, err := client.SyncReady(context.Background(), &proto.SyncReadyRequest{
-				Unit: "unregistered-unit",
-			})
+			ready, err := client.SyncReady(ctx, "unregistered-unit")
 			require.NoError(t, err)
-			require.False(t, response.Ready)
+			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(
-				socketPath,
 				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
 			)
 			require.NoError(t, err)
 			defer server.Close()

-			client := newSocketClient(t, socketPath)
+			client := newSocketClient(ctx, t, socketPath)

 			// Register a unit with an unsatisfied dependency
-			_, err = client.SyncWant(context.Background(), &proto.SyncWantRequest{
-				Unit:      "test-unit",
-				DependsOn: "dependency-unit",
-			})
+			err = client.SyncWant(ctx, "test-unit", "dependency-unit")
 			require.NoError(t, err)

 			// Check readiness - should be false because dependency is not satisfied
-			response, err := client.SyncReady(context.Background(), &proto.SyncReadyRequest{
-				Unit: "test-unit",
-			})
+			ready, err := client.SyncReady(ctx, "test-unit")
 			require.NoError(t, err)
-			require.False(t, response.Ready)
+			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(
-				socketPath,
 				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
 			)
 			require.NoError(t, err)
 			defer server.Close()

-			client := newSocketClient(t, socketPath)
+			client := newSocketClient(ctx, t, socketPath)

 			// Register a unit with no dependencies - should be ready immediately
-			_, err = client.SyncStart(context.Background(), &proto.SyncStartRequest{
-				Unit: "test-unit",
-			})
+			err = client.SyncStart(ctx, "test-unit")
 			require.NoError(t, err)

 			// Check readiness - should be true
-			_, err = client.SyncReady(context.Background(), &proto.SyncReadyRequest{
-				Unit: "test-unit",
-			})
+			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(context.Background(), &proto.SyncWantRequest{
-				Unit:      "dependent-unit",
-				DependsOn: "test-unit",
-			})
+			err = client.SyncWant(ctx, "dependent-unit", "test-unit")
 			require.NoError(t, err)

 			// Complete the dependency
-			_, err = client.SyncComplete(context.Background(), &proto.SyncCompleteRequest{
-				Unit: "test-unit",
-			})
+			err = client.SyncComplete(ctx, "test-unit")
 			require.NoError(t, err)

 			// Now dependent-unit should be ready
-			_, err = client.SyncReady(context.Background(), &proto.SyncReadyRequest{
-				Unit: "dependent-unit",
-			})
+			ready, err = client.SyncReady(ctx, "dependent-unit")
 			require.NoError(t, err)
+			require.True(t, ready)
 		})
 	})
 }
@@ -3,8 +3,7 @@
 package agentsocket

 import (
-	"crypto/rand"
-	"encoding/hex"
+	"context"
 	"net"
 	"os"
 	"path/filepath"
@@ -13,8 +12,13 @@ import (
 	"golang.org/x/xerrors"
 )

-// createSocket creates a Unix domain socket listener
+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)
 	}
@@ -23,7 +27,6 @@ func createSocket(path string) (net.Listener, error) {
 		return nil, xerrors.Errorf("remove existing socket: %w", err)
 	}

-	// Create parent directory if it doesn't exist
 	parentDir := filepath.Dir(path)
 	if err := os.MkdirAll(parentDir, 0o700); err != nil {
 		return nil, xerrors.Errorf("create socket directory: %w", err)
@@ -41,43 +44,30 @@ func createSocket(path string) (net.Listener, error) {
 	return listener, nil
 }

-// getDefaultSocketPath returns the default socket path for Unix-like systems
-func getDefaultSocketPath() (string, error) {
-	randomBytes := make([]byte, 4)
-	if _, err := rand.Read(randomBytes); err != nil {
-		return "", xerrors.Errorf("generate random socket name: %w", err)
-	}
-	randomSuffix := hex.EncodeToString(randomBytes)
-
-	// Try XDG_RUNTIME_DIR first
-	if runtimeDir := os.Getenv("XDG_RUNTIME_DIR"); runtimeDir != "" {
-		return filepath.Join(runtimeDir, "coder-agent-"+randomSuffix+".sock"), nil
-	}
-
-	return filepath.Join("/tmp", "coder-agent-"+randomSuffix+".sock"), nil
-}
-
-// CleanupSocket removes the socket file
 func cleanupSocket(path string) error {
 	return os.Remove(path)
 }

-// isSocketAvailable checks if a socket path is available for use
 func isSocketAvailable(path string) bool {
-	// Check if file exists
 	if _, err := os.Stat(path); os.IsNotExist(err) {
 		return true
 	}

-	// Try to connect to see if it's actually listening
+	// Try to connect to see if it's actually listening.
 	dialer := net.Dialer{Timeout: 10 * time.Second}
 	conn, err := dialer.Dial("unix", path)
 	if err != nil {
-		// If we can't connect, the socket is not in use
-		// Socket is available for use
 		return true
 	}
 	_ = conn.Close()
-	// Socket is in use
 	return false
 }
+
+func dialSocket(ctx context.Context, path string) (net.Conn, error) {
+	if path == "" {
+		path = defaultSocketPath
+	}
+
+	dialer := net.Dialer{}
+	return dialer.DialContext(ctx, "unix", path)
+}
@@ -3,25 +3,20 @@
 package agentsocket

 import (
+	"context"
 	"net"

 	"golang.org/x/xerrors"
 )

-// createSocket returns an error indicating that agentsocket is not supported on Windows.
-// This feature is unix-only in its current experimental state.
 func createSocket(_ string) (net.Listener, error) {
 	return nil, xerrors.New("agentsocket is not supported on Windows")
 }

-// getDefaultSocketPath returns an error indicating that agentsocket is not supported on Windows.
-// This feature is unix-only in its current experimental state.
-func getDefaultSocketPath() (string, error) {
-	return "", xerrors.New("agentsocket is not supported on Windows")
-}
-
-// cleanupSocket is a no-op on Windows since agentsocket is not supported.
 func cleanupSocket(_ string) error {
-	// No-op since agentsocket is not supported on Windows
 	return nil
 }
+
+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,
 	})
 }
@@ -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.
@@ -4,6 +4,8 @@ import (
 	"os"

 	"github.com/hashicorp/go-reap"
+
+	"cdr.dev/slog"
 )

 type Option func(o *options)
@@ -34,8 +36,15 @@ func WithCatchSignals(sigs ...os.Signal) Option {
 	}
 }

+func WithLogger(logger slog.Logger) Option {
+	return func(o *options) {
+		o.Logger = logger
+	}
+}
+
 type options struct {
 	ExecArgs     []string
 	PIDs         reap.PidCh
 	CatchSignals []os.Signal
+	Logger       slog.Logger
 }
@@ -7,6 +7,6 @@ func IsInitProcess() bool {
 	return false
 }

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

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

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

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

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

 	require.Equal(t, <-usrSig, syscall.SIGUSR1)
@@ -3,12 +3,15 @@
 package reaper

 import (
+	"context"
 	"os"
 	"os/signal"
 	"syscall"

 	"github.com/hashicorp/go-reap"
 	"golang.org/x/xerrors"
+
+	"cdr.dev/slog"
 )

 // IsInitProcess returns true if the current process's PID is 1.
@@ -16,7 +19,7 @@ func IsInitProcess() bool {
 	return os.Getpid() == 1
 }

-func catchSignals(pid int, sigs []os.Signal) {
+func catchSignals(logger slog.Logger, pid int, sigs []os.Signal) {
 	if len(sigs) == 0 {
 		return
 	}
@@ -25,10 +28,19 @@ func catchSignals(pid int, sigs []os.Signal) {
 	signal.Notify(sc, sigs...)
 	defer signal.Stop(sc)

+	logger.Info(context.Background(), "reaper catching signals",
+		slog.F("signals", sigs),
+		slog.F("child_pid", pid),
+	)
+
 	for {
 		s := <-sc
 		sig, ok := s.(syscall.Signal)
 		if ok {
+			logger.Info(context.Background(), "reaper caught signal, killing child process",
+				slog.F("signal", sig.String()),
+				slog.F("child_pid", pid),
+			)
 			_ = syscall.Kill(pid, sig)
 		}
 	}
@@ -40,7 +52,10 @@ func catchSignals(pid int, sigs []os.Signal) {
 // the reaper and an exec.Command waiting for its process to complete.
 // The provided 'pids' channel may be nil if the caller does not care about the
 // reaped children PIDs.
-func ForkReap(opt ...Option) error {
+//
+// Returns the child's exit code (using 128+signal for signal termination)
+// and any error from Wait4.
+func ForkReap(opt ...Option) (int, error) {
 	opts := &options{
 		ExecArgs: os.Args,
 	}
@@ -53,7 +68,7 @@ func ForkReap(opt ...Option) error {

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

 	pattrs := &syscall.ProcAttr{
@@ -72,15 +87,28 @@ func ForkReap(opt ...Option) error {
 	//#nosec G204
 	pid, err := syscall.ForkExec(opts.ExecArgs[0], opts.ExecArgs, pattrs)
 	if err != nil {
-		return xerrors.Errorf("fork exec: %w", err)
+		return 1, xerrors.Errorf("fork exec: %w", err)
 	}

-	go catchSignals(pid, opts.CatchSignals)
+	go catchSignals(opts.Logger, pid, opts.CatchSignals)

 	var wstatus syscall.WaitStatus
 	_, err = syscall.Wait4(pid, &wstatus, 0, nil)
 	for xerrors.Is(err, syscall.EINTR) {
 		_, err = syscall.Wait4(pid, &wstatus, 0, nil)
 	}
-	return err
+
+	// Convert wait status to exit code using standard Unix conventions:
+	// - Normal exit: use the exit code
+	// - Signal termination: use 128 + signal number
+	var exitCode int
+	switch {
+	case wstatus.Exited():
+		exitCode = wstatus.ExitStatus()
+	case wstatus.Signaled():
+		exitCode = 128 + int(wstatus.Signal())
+	default:
+		exitCode = 1
+	}
+	return exitCode, err
 }
@@ -2,6 +2,7 @@ package unit

 import (
 	"errors"
+	"fmt"
 	"sync"

 	"golang.org/x/xerrors"
@@ -23,6 +24,15 @@ var (
 // 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 = ""
@@ -137,7 +147,7 @@ func (m *Manager) IsReady(id ID) (bool, error) {
 	defer m.mu.RUnlock()

 	if !m.registered(id) {
-		return false, nil
+		return true, nil
 	}

 	return m.units[id].ready, nil
@@ -684,7 +684,7 @@ func TestManager_IsReady(t *testing.T) {
 		// Then: the unit is not ready
 		isReady, err := manager.IsReady(unitA)
 		require.NoError(t, err)
-		assert.False(t, isReady)
+		assert.True(t, isReady)
 	})
 }

@@ -9,6 +9,7 @@ import (
 	"net/http/pprof"
 	"net/url"
 	"os"
+	"os/signal"
 	"path/filepath"
 	"runtime"
 	"slices"
@@ -57,6 +58,8 @@ func workspaceAgent() *serpent.Command {
 		devcontainers                  bool
 		devcontainerProjectDiscovery   bool
 		devcontainerDiscoveryAutostart bool
+		socketServerEnabled            bool
+		socketPath                     string
 	)
 	agentAuth := &AgentAuth{}
 	cmd := &serpent.Command{
@@ -128,40 +131,29 @@ func workspaceAgent() *serpent.Command {

 				sinks = append(sinks, sloghuman.Sink(logWriter))
 				logger := inv.Logger.AppendSinks(sinks...).Leveled(slog.LevelDebug)
+				logger = logger.Named("reaper")

 				logger.Info(ctx, "spawning reaper process")
 				// Do not start a reaper on the child process. It's important
 				// to do this else we fork bomb ourselves.
 				//nolint:gocritic
 				args := append(os.Args, "--no-reap")
-				err := reaper.ForkReap(
+				exitCode, err := reaper.ForkReap(
 					reaper.WithExecArgs(args...),
 					reaper.WithCatchSignals(StopSignals...),
+					reaper.WithLogger(logger),
 				)
 				if err != nil {
 					logger.Error(ctx, "agent process reaper unable to fork", slog.Error(err))
 					return xerrors.Errorf("fork reap: %w", err)
 				}

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

-			// Handle interrupt signals to allow for graceful shutdown,
-			// note that calling stopNotify disables the signal handler
-			// and the next interrupt will terminate the program (you
-			// probably want cancel instead).
-			//
-			// Note that we don't want to handle these signals in the
-			// process that runs as PID 1, that's why we do this after
-			// the reaper forked.
-			ctx, stopNotify := inv.SignalNotifyContext(ctx, StopSignals...)
-			defer stopNotify()
-
-			// DumpHandler does signal handling, so we call it after the
-			// reaper.
-			go DumpHandler(ctx, "agent")
-
 			logWriter := &clilog.LumberjackWriteCloseFixer{Writer: &lumberjack.Logger{
 				Filename: filepath.Join(logDir, "coder-agent.log"),
 				MaxSize:  5, // MB
@@ -174,6 +166,21 @@ func workspaceAgent() *serpent.Command {
 			sinks = append(sinks, sloghuman.Sink(logWriter))
 			logger := inv.Logger.AppendSinks(sinks...).Leveled(slog.LevelDebug)

+			// Handle interrupt signals to allow for graceful shutdown,
+			// note that calling stopNotify disables the signal handler
+			// and the next interrupt will terminate the program (you
+			// probably want cancel instead).
+			//
+			// Note that we also handle these signals in the
+			// process that runs as PID 1, mainly to forward it to the agent child
+			// so that it can shutdown gracefully.
+			ctx, stopNotify := logSignalNotifyContext(ctx, logger, StopSignals...)
+			defer stopNotify()
+
+			// DumpHandler does signal handling, so we call it after the
+			// reaper.
+			go DumpHandler(ctx, "agent")
+
 			version := buildinfo.Version()
 			logger.Info(ctx, "agent is starting now",
 				slog.F("url", agentAuth.agentURL),
@@ -317,6 +324,8 @@ func workspaceAgent() *serpent.Command {
 						agentcontainers.WithProjectDiscovery(devcontainerProjectDiscovery),
 						agentcontainers.WithDiscoveryAutostart(devcontainerDiscoveryAutostart),
 					},
+					SocketPath:          socketPath,
+					SocketServerEnabled: socketServerEnabled,
 				})

 				if debugAddress != "" {
@@ -477,6 +486,19 @@ 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
@@ -540,3 +562,26 @@ func urlPort(u string) (int, error) {
 	}
 	return -1, xerrors.Errorf("invalid port: %s", u)
 }
+
+// logSignalNotifyContext is like signal.NotifyContext but logs the received
+// signal before canceling the context.
+func logSignalNotifyContext(parent context.Context, logger slog.Logger, signals ...os.Signal) (context.Context, context.CancelFunc) {
+	ctx, cancel := context.WithCancelCause(parent)
+	c := make(chan os.Signal, 1)
+	signal.Notify(c, signals...)
+
+	go func() {
+		select {
+		case sig := <-c:
+			logger.Info(ctx, "agent received signal", slog.F("signal", sig.String()))
+			cancel(xerrors.Errorf("signal: %s", sig.String()))
+		case <-ctx.Done():
+			logger.Info(ctx, "ctx canceled, stopping signal handler")
+		}
+	}()
+
+	return ctx, func() {
+		cancel(context.Canceled)
+		signal.Stop(c)
+	}
+}
@@ -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.
@@ -2,62 +2,85 @@ 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"
 )

-// mockKeyring is a mock sessionstore.Backend implementation.
-type mockKeyring struct {
-	credentials map[string]string // service name -> credential
-}
-
-const mockServiceName = "mock-service-name"
-
-func newMockKeyring() *mockKeyring {
-	return &mockKeyring{credentials: make(map[string]string)}
-}
-
-func (m *mockKeyring) Read(_ *url.URL) (string, error) {
-	cred, ok := m.credentials[mockServiceName]
-	if !ok {
-		return "", os.ErrNotExist
+// 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 cred, nil
+	return fmt.Sprintf("%s_%v_%d", t.Name(), time.Now().UnixNano(), n)
 }

-func (m *mockKeyring) Write(_ *url.URL, token string) error {
-	m.credentials[mockServiceName] = token
-	return nil
+type keyringTestEnv struct {
+	serviceName string
+	keyring     sessionstore.Keyring
+	inv         *serpent.Invocation
+	cfg         config.Root
+	clientURL   *url.URL
 }

-func (m *mockKeyring) Delete(_ *url.URL) error {
-	_, ok := m.credentials[mockServiceName]
-	if !ok {
-		return os.ErrNotExist
-	}
-	delete(m.credentials, mockServiceName)
-	return nil
+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 opts into using a keyring backend for
-	// storing session tokens instead of plain text files.
+	// 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)
@@ -65,25 +88,16 @@ func TestUseKeyring(t *testing.T) {
 		// Create a pty for interactive prompts
 		pty := ptytest.New(t)

-		// Create CLI invocation with --use-keyring flag
-		inv, cfg := clitest.New(t,
+		// Create CLI invocation which defaults to using the keyring
+		env := setupKeyringTestEnv(t, client.URL.String(),
 			"login",
 			"--force-tty",
-			"--use-keyring",
 			"--no-open",
-			client.URL.String(),
-		)
+			client.URL.String())
+		inv := env.inv
 		inv.Stdin = pty.Input()
 		inv.Stdout = pty.Output()

-		// Inject the mock backend before running the command
-		var root cli.RootCmd
-		cmd, err := root.Command(root.AGPL())
-		require.NoError(t, err)
-		mockBackend := newMockKeyring()
-		root.WithSessionStorageBackend(mockBackend)
-		inv.Command = cmd
-
 		// Run login in background
 		doneChan := make(chan struct{})
 		go func() {
@@ -99,19 +113,23 @@ func TestUseKeyring(t *testing.T) {
 		<-doneChan

 		// Verify that session file was NOT created (using keyring instead)
-		sessionFile := path.Join(string(cfg), "session")
-		_, err = os.Stat(sessionFile)
+		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 mock keyring
-		cred, err := mockBackend.Read(nil)
-		require.NoError(t, err, "credential should be stored in mock 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)
@@ -119,25 +137,17 @@ func TestUseKeyring(t *testing.T) {
 		// Create a pty for interactive prompts
 		pty := ptytest.New(t)

-		// First, login with --use-keyring
-		loginInv, cfg := clitest.New(t,
+		// First, login with the keyring (default)
+		env := setupKeyringTestEnv(t, client.URL.String(),
 			"login",
 			"--force-tty",
-			"--use-keyring",
 			"--no-open",
 			client.URL.String(),
 		)
+		loginInv := env.inv
 		loginInv.Stdin = pty.Input()
 		loginInv.Stdout = pty.Output()

-		// Inject the mock backend
-		var loginRoot cli.RootCmd
-		loginCmd, err := loginRoot.Command(loginRoot.AGPL())
-		require.NoError(t, err)
-		mockBackend := newMockKeyring()
-		loginRoot.WithSessionStorageBackend(mockBackend)
-		loginInv.Command = loginCmd
-
 		doneChan := make(chan struct{})
 		go func() {
 			defer close(doneChan)
@@ -150,25 +160,23 @@ func TestUseKeyring(t *testing.T) {
 		pty.ExpectMatch("Welcome to Coder")
 		<-doneChan

-		// Verify credential exists in mock keyring
-		cred, err := mockBackend.Read(nil)
+		// 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 after logout")
+		require.NotEmpty(t, cred, "credential should exist before logout")

-		// Now run logout with --use-keyring
-		logoutInv, _ := clitest.New(t,
-			"logout",
-			"--use-keyring",
-			"--yes",
-			"--global-config", string(cfg),
-		)
-
-		// Inject the same mock backend
+		// Now logout using the same keyring service name
 		var logoutRoot cli.RootCmd
 		logoutCmd, err := logoutRoot.Command(logoutRoot.AGPL())
 		require.NoError(t, err)
-		logoutRoot.WithSessionStorageBackend(mockBackend)
-		logoutInv.Command = logoutCmd
+		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
@@ -176,14 +184,18 @@ func TestUseKeyring(t *testing.T) {
 		err = logoutInv.Run()
 		require.NoError(t, err, "logout should succeed")

-		// Verify the credential was deleted from mock keyring
-		_, err = mockBackend.Read(nil)
+		// 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("OmitFlag", func(t *testing.T) {
+	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)
@@ -191,13 +203,13 @@ func TestUseKeyring(t *testing.T) {
 		// Create a pty for interactive prompts
 		pty := ptytest.New(t)

-		// --use-keyring flag omitted (should use file-based storage)
-		inv, cfg := clitest.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()

@@ -214,9 +226,9 @@ func TestUseKeyring(t *testing.T) {
 		<-doneChan

 		// Verify that session file WAS created (not using keyring)
-		sessionFile := path.Join(string(cfg), "session")
+		sessionFile := path.Join(string(env.cfg), "session")
 		_, err := os.Stat(sessionFile)
-		require.NoError(t, err, "session file should exist when NOT using --use-keyring")
+		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)
@@ -234,24 +246,18 @@ func TestUseKeyring(t *testing.T) {
 		// Create a pty for interactive prompts
 		pty := ptytest.New(t)

-		// Login using CODER_USE_KEYRING environment variable instead of flag
-		inv, cfg := clitest.New(t,
+		// Login 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", "true")
-
-		// Inject the mock backend
-		var root cli.RootCmd
-		cmd, err := root.Command(root.AGPL())
-		require.NoError(t, err)
-		mockBackend := newMockKeyring()
-		root.WithSessionStorageBackend(mockBackend)
-		inv.Command = cmd
+		inv.Environ.Set("CODER_USE_KEYRING", "false")

 		doneChan := make(chan struct{})
 		go func() {
@@ -265,21 +271,64 @@ func TestUseKeyring(t *testing.T) {
 		pty.ExpectMatch("Welcome to Coder")
 		<-doneChan

-		// Verify that session file was NOT created (using keyring via env var)
-		sessionFile := path.Join(string(cfg), "session")
-		_, err = os.Stat(sessionFile)
-		require.True(t, os.IsNotExist(err), "session file should not exist when using keyring via env var")
+		// Verify 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")

-		// Verify credential is in mock keyring
-		cred, err := mockBackend.Read(nil)
-		require.NoError(t, err, "credential should be stored in keyring when CODER_USE_KEYRING=true")
-		require.NotEmpty(t, cred)
+		// 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 trying to use --use-keyring on an unsupported operating system produces
-	// a helpful error message.
+	// 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.
@@ -287,43 +336,60 @@ func TestUseKeyringUnsupportedOS(t *testing.T) {
 		t.Skipf("Skipping unsupported OS test on %s where keyring is supported", runtime.GOOS)
 	}

-	const expMessage = "keyring storage is not supported on this operating system; remove the --use-keyring flag"
-
-	t.Run("LoginWithUnsupportedKeyring", func(t *testing.T) {
-		t.Parallel()
-
-		client := coderdtest.New(t, nil)
-		coderdtest.CreateFirstUser(t, client)
-
-		// Try to login with --use-keyring on an unsupported OS
-		inv, _ := clitest.New(t,
-			"login",
-			"--use-keyring",
-			client.URL.String(),
-		)
-
-		// The error should occur immediately, before any prompts
-		loginErr := inv.Run()
-
-		// Verify we got an error about unsupported OS
-		require.Error(t, loginErr)
-		require.Contains(t, loginErr.Error(), expMessage)
-	})
-
-	t.Run("LogoutWithUnsupportedKeyring", func(t *testing.T) {
+	t.Run("LoginWithDefaultKeyring", func(t *testing.T) {
 		t.Parallel()

 		client := coderdtest.New(t, nil)
 		coderdtest.CreateFirstUser(t, client)
 		pty := ptytest.New(t)

-		// First login without keyring to create a session
-		loginInv, cfg := clitest.New(t,
+		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()

@@ -339,17 +405,22 @@ func TestUseKeyringUnsupportedOS(t *testing.T) {
 		pty.ExpectMatch("Welcome to Coder")
 		<-doneChan

-		// Now try to logout with --use-keyring on an unsupported OS
-		logoutInv, _ := clitest.New(t,
+		// 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",
-			"--use-keyring",
 			"--yes",
-			"--global-config", string(cfg),
+			"--global-config", string(env.cfg),
 		)

-		err := logoutInv.Run()
-		// Verify we got an error about unsupported OS
-		require.Error(t, err)
-		require.Contains(t, err.Error(), expMessage)
+		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")
 	})
 }
@@ -154,9 +154,9 @@ func (r *RootCmd) login() *serpent.Command {
 	cmd := &serpent.Command{
 		Use:   "login [<url>]",
 		Short: "Authenticate with Coder deployment",
-		Long: "By default, the session token is stored in a plain text file. Use the " +
-			"--use-keyring flag or set CODER_USE_KEYRING=true to store the token in " +
-			"the operating system keyring instead.",
+		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()
@@ -56,7 +56,7 @@ var (
 	// anything.
 	ErrSilent = xerrors.New("silent error")

-	errKeyringNotSupported = xerrors.New("keyring storage is not supported on this operating system; remove the --use-keyring flag to use file-based storage")
+	errKeyringNotSupported = xerrors.New("keyring storage is not supported on this operating system; omit --use-keyring to use file-based storage")
 )

 const (
@@ -104,6 +104,7 @@ func (r *RootCmd) CoreSubcommands() []*serpent.Command {
 		r.resetPassword(),
 		r.sharing(),
 		r.state(),
+		r.tasksCommand(),
 		r.templates(),
 		r.tokens(),
 		r.users(),
@@ -149,7 +150,7 @@ func (r *RootCmd) AGPLExperimental() []*serpent.Command {
 		r.mcpCommand(),
 		r.promptExample(),
 		r.rptyCommand(),
-		r.tasksCommand(),
+		r.syncCommand(),
 		r.boundary(),
 	}
 }
@@ -483,10 +484,12 @@ func (r *RootCmd) Command(subcommands []*serpent.Command) (*serpent.Command, err
 			Flag: varUseKeyring,
 			Env:  envUseKeyring,
 			Description: "Store and retrieve session tokens using the operating system " +
-				"keyring. Currently only supported on Windows. By default, tokens are " +
-				"stored in plain text files.",
-			Value: serpent.BoolOf(&r.useKeyring),
-			Group: globalGroup,
+				"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",
@@ -534,10 +537,12 @@ type RootCmd struct {
 	disableDirect bool
 	debugHTTP     bool

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

 // InitClient creates and configures a new client with authentication, telemetry,
@@ -718,8 +723,19 @@ func (r *RootCmd) createUnauthenticatedClient(ctx context.Context, serverURL *ur
 // flag.
 func (r *RootCmd) ensureTokenBackend() sessionstore.Backend {
 	if r.tokenBackend == nil {
-		if r.useKeyring {
-			r.tokenBackend = sessionstore.NewKeyring()
+		// 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)
 		}
@@ -727,8 +743,18 @@ func (r *RootCmd) ensureTokenBackend() sessionstore.Backend {
 	return r.tokenBackend
 }

-func (r *RootCmd) WithSessionStorageBackend(backend sessionstore.Backend) {
-	r.tokenBackend = backend
+// 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 {
@@ -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"},
+		},
 	))
 }

@@ -47,9 +47,9 @@ var (
 )

 const (
-	// defaultServiceName is the service name used in keyrings  for storing Coder CLI session
+	// DefaultServiceName is the service name used in keyrings for storing Coder CLI session
 	// tokens.
-	defaultServiceName = "coder-v2-credentials"
+	DefaultServiceName = "coder-v2-credentials"
 )

 // keyringProvider represents an operating system keyring. The expectation
@@ -108,17 +108,9 @@ type Keyring struct {
 	serviceName string
 }

-// NewKeyring creates a Keyring with the default service name for production use.
-func NewKeyring() Keyring {
-	return Keyring{
-		provider:    operatingSystemKeyring{},
-		serviceName: defaultServiceName,
-	}
-}
-
 // NewKeyringWithService creates a Keyring Backend that stores credentials under the
-// specified service name. This is primarily intended for testing to avoid conflicts
-// with production credentials and collisions between tests.
+// 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{},
@@ -87,6 +87,7 @@ func buildNumberOption(n *int64) serpent.Option {

 func (r *RootCmd) statePush() *serpent.Command {
 	var buildNumber int64
+	var noBuild bool
 	cmd := &serpent.Command{
 		Use:   "push <workspace> <file>",
 		Short: "Push a Terraform state file to a workspace.",
@@ -126,6 +127,16 @@ func (r *RootCmd) statePush() *serpent.Command {
 				return err
 			}

+			if noBuild {
+				// Update state directly without triggering a build.
+				err = client.UpdateWorkspaceBuildState(inv.Context(), build.ID, state)
+				if err != nil {
+					return err
+				}
+				_, _ = fmt.Fprintln(inv.Stdout, "State updated successfully.")
+				return nil
+			}
+
 			build, err = client.CreateWorkspaceBuild(inv.Context(), workspace.ID, codersdk.CreateWorkspaceBuildRequest{
 				TemplateVersionID: build.TemplateVersionID,
 				Transition:        build.Transition,
@@ -139,6 +150,12 @@ func (r *RootCmd) statePush() *serpent.Command {
 	}
 	cmd.Options = serpent.OptionSet{
 		buildNumberOption(&buildNumber),
+		{
+			Flag:          "no-build",
+			FlagShorthand: "n",
+			Description:   "Update the state without triggering a workspace build. Useful for state-only migrations.",
+			Value:         serpent.BoolOf(&noBuild),
+		},
 	}
 	return cmd
 }
@@ -2,6 +2,7 @@ package cli_test

 import (
 	"bytes"
+	"context"
 	"fmt"
 	"os"
 	"path/filepath"
@@ -10,6 +11,7 @@ import (
 	"testing"

 	"github.com/coder/coder/v2/coderd/database"
+	"github.com/coder/coder/v2/coderd/database/dbauthz"
 	"github.com/coder/coder/v2/coderd/database/dbfake"

 	"github.com/stretchr/testify/require"
@@ -158,4 +160,49 @@ func TestStatePush(t *testing.T) {
 		err := inv.Run()
 		require.NoError(t, err)
 	})
+
+	t.Run("NoBuild", func(t *testing.T) {
+		t.Parallel()
+		client, store := coderdtest.NewWithDatabase(t, nil)
+		owner := coderdtest.CreateFirstUser(t, client)
+		templateAdmin, taUser := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID, rbac.RoleTemplateAdmin())
+		initialState := []byte("initial state")
+		r := dbfake.WorkspaceBuild(t, store, database.WorkspaceTable{
+			OrganizationID: owner.OrganizationID,
+			OwnerID:        taUser.ID,
+		}).
+			Seed(database.WorkspaceBuild{ProvisionerState: initialState}).
+			Do()
+		wantState := []byte("updated state")
+		stateFile, err := os.CreateTemp(t.TempDir(), "")
+		require.NoError(t, err)
+		_, err = stateFile.Write(wantState)
+		require.NoError(t, err)
+		err = stateFile.Close()
+		require.NoError(t, err)
+
+		inv, root := clitest.New(t, "state", "push", "--no-build", r.Workspace.Name, stateFile.Name())
+		clitest.SetupConfig(t, templateAdmin, root)
+		var stdout bytes.Buffer
+		inv.Stdout = &stdout
+		err = inv.Run()
+		require.NoError(t, err)
+		require.Contains(t, stdout.String(), "State updated successfully")
+
+		// Verify the state was updated by pulling it.
+		inv, root = clitest.New(t, "state", "pull", r.Workspace.Name)
+		var gotState bytes.Buffer
+		inv.Stdout = &gotState
+		clitest.SetupConfig(t, templateAdmin, root)
+		err = inv.Run()
+		require.NoError(t, err)
+		require.Equal(t, wantState, bytes.TrimSpace(gotState.Bytes()))
+
+		// Verify no new build was created.
+		builds, err := store.GetWorkspaceBuildsByWorkspaceID(dbauthz.AsSystemRestricted(context.Background()), database.GetWorkspaceBuildsByWorkspaceIDParams{
+			WorkspaceID: r.Workspace.ID,
+		})
+		require.NoError(t, err)
+		require.Len(t, builds, 1, "expected only the initial build, no new build should be created")
+	})
 }
@@ -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
+}
@@ -0,0 +1,42 @@
+package cli
+
+import (
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/agent/agentsocket"
+	"github.com/coder/coder/v2/cli/cliui"
+	"github.com/coder/serpent"
+)
+
+func (*RootCmd) syncPing(socketPath *string) *serpent.Command {
+	cmd := &serpent.Command{
+		Use:   "ping",
+		Short: "Test agent socket connectivity and health",
+		Long:  "Test connectivity to the local Coder agent socket to verify the agent is running and responsive. Useful for troubleshooting startup issues or verifying the agent is accessible before running other sync commands.",
+		Handler: func(i *serpent.Invocation) error {
+			ctx := i.Context()
+
+			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()
+
+			err = client.Ping(ctx)
+			if err != nil {
+				return xerrors.Errorf("ping failed: %w", err)
+			}
+
+			cliui.Info(i.Stdout, "Success")
+
+			return nil
+		},
+	}
+
+	return cmd
+}
@@ -0,0 +1,101 @@
+package cli
+
+import (
+	"context"
+	"time"
+
+	"golang.org/x/xerrors"
+
+	"github.com/coder/serpent"
+
+	"github.com/coder/coder/v2/agent/agentsocket"
+	"github.com/coder/coder/v2/agent/unit"
+	"github.com/coder/coder/v2/cli/cliui"
+)
+
+const (
+	syncPollInterval = 1 * time.Second
+)
+
+func (*RootCmd) syncStart(socketPath *string) *serpent.Command {
+	var timeout time.Duration
+
+	cmd := &serpent.Command{
+		Use:   "start <unit>",
+		Short: "Wait until all unit dependencies are satisfied",
+		Long:  "Wait until all dependencies are satisfied, consider the unit to have started, then allow it to proceed. This command polls until dependencies are ready, then marks the unit as started.",
+		Handler: func(i *serpent.Invocation) error {
+			ctx := i.Context()
+
+			if len(i.Args) != 1 {
+				return xerrors.New("exactly one unit name is required")
+			}
+			unitName := unit.ID(i.Args[0])
+
+			if timeout > 0 {
+				var cancel context.CancelFunc
+				ctx, cancel = context.WithTimeout(ctx, timeout)
+				defer cancel()
+			}
+
+			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()
+
+			ready, err := client.SyncReady(ctx, unitName)
+			if err != nil {
+				return xerrors.Errorf("error checking dependencies: %w", err)
+			}
+
+			if !ready {
+				cliui.Infof(i.Stdout, "Waiting for dependencies of unit '%s' to be satisfied...", unitName)
+
+				ticker := time.NewTicker(syncPollInterval)
+				defer ticker.Stop()
+
+			pollLoop:
+				for {
+					select {
+					case <-ctx.Done():
+						if ctx.Err() == context.DeadlineExceeded {
+							return xerrors.Errorf("timeout waiting for dependencies of unit '%s'", unitName)
+						}
+						return ctx.Err()
+					case <-ticker.C:
+						ready, err := client.SyncReady(ctx, unitName)
+						if err != nil {
+							return xerrors.Errorf("error checking dependencies: %w", err)
+						}
+						if ready {
+							break pollLoop
+						}
+					}
+				}
+			}
+
+			if err := client.SyncStart(ctx, unitName); err != nil {
+				return xerrors.Errorf("start unit failed: %w", err)
+			}
+
+			cliui.Info(i.Stdout, "Success")
+
+			return nil
+		},
+	}
+
+	cmd.Options = append(cmd.Options, serpent.Option{
+		Flag:        "timeout",
+		Description: "Maximum time to wait for dependencies (e.g., 30s, 5m). 5m by default.",
+		Value:       serpent.DurationOf(&timeout),
+		Default:     "5m",
+	})
+
+	return cmd
+}
@@ -0,0 +1,88 @@
+package cli
+
+import (
+	"fmt"
+
+	"golang.org/x/xerrors"
+
+	"github.com/coder/serpent"
+
+	"github.com/coder/coder/v2/agent/agentsocket"
+	"github.com/coder/coder/v2/agent/unit"
+	"github.com/coder/coder/v2/cli/cliui"
+)
+
+func (*RootCmd) syncStatus(socketPath *string) *serpent.Command {
+	formatter := cliui.NewOutputFormatter(
+		cliui.ChangeFormatterData(
+			cliui.TableFormat(
+				[]agentsocket.DependencyInfo{},
+				[]string{
+					"depends on",
+					"required status",
+					"current status",
+					"satisfied",
+				},
+			),
+			func(data any) (any, error) {
+				resp, ok := data.(agentsocket.SyncStatusResponse)
+				if !ok {
+					return nil, xerrors.Errorf("expected agentsocket.SyncStatusResponse, got %T", data)
+				}
+				return resp.Dependencies, nil
+			}),
+		cliui.JSONFormat(),
+	)
+
+	cmd := &serpent.Command{
+		Use:   "status <unit>",
+		Short: "Show unit status and dependency state",
+		Long:  "Show the current status of a unit, whether it is ready to start, and lists its dependencies. Shows which dependencies are satisfied and which are still pending. Supports multiple output formats.",
+		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()
+
+			statusResp, err := client.SyncStatus(ctx, unit)
+			if err != nil {
+				return xerrors.Errorf("get status failed: %w", err)
+			}
+
+			var out string
+			header := fmt.Sprintf("Unit: %s\nStatus: %s\nReady: %t\n\nDependencies:\n", unit, statusResp.Status, statusResp.IsReady)
+			if formatter.FormatID() == "table" && len(statusResp.Dependencies) == 0 {
+				out = header + "No dependencies found"
+			} else {
+				out, err = formatter.Format(ctx, statusResp)
+				if err != nil {
+					return xerrors.Errorf("format status: %w", err)
+				}
+
+				if formatter.FormatID() == "table" {
+					out = header + out
+				}
+			}
+
+			_, _ = fmt.Fprintln(i.Stdout, out)
+
+			return nil
+		},
+	}
+
+	formatter.AttachOptions(&cmd.Options)
+	return cmd
+}
@@ -0,0 +1,330 @@
+//go:build !windows
+
+package cli_test
+
+import (
+	"bytes"
+	"context"
+	"os"
+	"path/filepath"
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/require"
+
+	"cdr.dev/slog"
+	"github.com/coder/coder/v2/agent/agentsocket"
+	"github.com/coder/coder/v2/cli/clitest"
+	"github.com/coder/coder/v2/testutil"
+)
+
+// setupSocketServer creates an agentsocket server at a temporary path for testing.
+// Returns the socket path and a cleanup function. The path should be passed to
+// sync commands via the --socket-path flag.
+func setupSocketServer(t *testing.T) (path string, cleanup func()) {
+	t.Helper()
+
+	// Use a temporary socket path for each test
+	socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+
+	// Create parent directory if needed
+	parentDir := filepath.Dir(socketPath)
+	err := os.MkdirAll(parentDir, 0o700)
+	require.NoError(t, err, "create socket directory")
+
+	server, err := agentsocket.NewServer(
+		slog.Make().Leveled(slog.LevelDebug),
+		agentsocket.WithPath(socketPath),
+	)
+	require.NoError(t, err, "create socket server")
+
+	// Return cleanup function
+	return socketPath, func() {
+		err := server.Close()
+		require.NoError(t, err, "close socket server")
+		_ = os.Remove(socketPath)
+	}
+}
+
+func TestSyncCommands_Golden(t *testing.T) {
+	t.Parallel()
+
+	t.Run("ping", func(t *testing.T) {
+		t.Parallel()
+		path, cleanup := setupSocketServer(t)
+		defer cleanup()
+
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		var outBuf bytes.Buffer
+		inv, _ := clitest.New(t, "exp", "sync", "ping", "--socket-path", path)
+		inv.Stdout = &outBuf
+		inv.Stderr = &outBuf
+
+		err := inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		clitest.TestGoldenFile(t, "TestSyncCommands_Golden/ping_success", outBuf.Bytes(), nil)
+	})
+
+	t.Run("start_no_dependencies", func(t *testing.T) {
+		t.Parallel()
+		path, cleanup := setupSocketServer(t)
+		defer cleanup()
+
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		var outBuf bytes.Buffer
+		inv, _ := clitest.New(t, "exp", "sync", "start", "test-unit", "--socket-path", path)
+		inv.Stdout = &outBuf
+		inv.Stderr = &outBuf
+
+		err := inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		clitest.TestGoldenFile(t, "TestSyncCommands_Golden/start_no_dependencies", outBuf.Bytes(), nil)
+	})
+
+	t.Run("start_with_dependencies", func(t *testing.T) {
+		t.Parallel()
+		path, cleanup := setupSocketServer(t)
+		defer cleanup()
+
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		// Set up dependency: test-unit depends on dep-unit
+		client, err := agentsocket.NewClient(ctx, agentsocket.WithPath(path))
+		require.NoError(t, err)
+
+		// Declare dependency
+		err = client.SyncWant(ctx, "test-unit", "dep-unit")
+		require.NoError(t, err)
+		client.Close()
+
+		// Start a goroutine to complete the dependency after a short delay
+		// This simulates the dependency being satisfied while start is waiting
+		// The delay ensures the "Waiting..." message appears in the output
+		done := make(chan error, 1)
+		go func() {
+			// Wait a moment to let the start command begin waiting and print the message
+			time.Sleep(100 * time.Millisecond)
+
+			compCtx := context.Background()
+			compClient, err := agentsocket.NewClient(compCtx, agentsocket.WithPath(path))
+			if err != nil {
+				done <- err
+				return
+			}
+			defer compClient.Close()
+
+			// Start and complete the dependency unit
+			err = compClient.SyncStart(compCtx, "dep-unit")
+			if err != nil {
+				done <- err
+				return
+			}
+			err = compClient.SyncComplete(compCtx, "dep-unit")
+			done <- err
+		}()
+
+		var outBuf bytes.Buffer
+		inv, _ := clitest.New(t, "exp", "sync", "start", "test-unit", "--socket-path", path)
+		inv.Stdout = &outBuf
+		inv.Stderr = &outBuf
+
+		// Run the start command - it should wait for the dependency
+		err = inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		// Ensure the completion goroutine finished
+		select {
+		case err := <-done:
+			require.NoError(t, err, "complete dependency")
+		case <-time.After(time.Second):
+			// Goroutine should have finished by now
+		}
+
+		clitest.TestGoldenFile(t, "TestSyncCommands_Golden/start_with_dependencies", outBuf.Bytes(), nil)
+	})
+
+	t.Run("want", func(t *testing.T) {
+		t.Parallel()
+		path, cleanup := setupSocketServer(t)
+		defer cleanup()
+
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		var outBuf bytes.Buffer
+		inv, _ := clitest.New(t, "exp", "sync", "want", "test-unit", "dep-unit", "--socket-path", path)
+		inv.Stdout = &outBuf
+		inv.Stderr = &outBuf
+
+		err := inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		clitest.TestGoldenFile(t, "TestSyncCommands_Golden/want_success", outBuf.Bytes(), nil)
+	})
+
+	t.Run("complete", func(t *testing.T) {
+		t.Parallel()
+		path, cleanup := setupSocketServer(t)
+		defer cleanup()
+
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		// First start the unit
+		client, err := agentsocket.NewClient(ctx, agentsocket.WithPath(path))
+		require.NoError(t, err)
+		err = client.SyncStart(ctx, "test-unit")
+		require.NoError(t, err)
+		client.Close()
+
+		var outBuf bytes.Buffer
+		inv, _ := clitest.New(t, "exp", "sync", "complete", "test-unit", "--socket-path", path)
+		inv.Stdout = &outBuf
+		inv.Stderr = &outBuf
+
+		err = inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		clitest.TestGoldenFile(t, "TestSyncCommands_Golden/complete_success", outBuf.Bytes(), nil)
+	})
+
+	t.Run("status_pending", func(t *testing.T) {
+		t.Parallel()
+		path, cleanup := setupSocketServer(t)
+		defer cleanup()
+
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		// Set up a unit with unsatisfied dependency
+		client, err := agentsocket.NewClient(ctx, agentsocket.WithPath(path))
+		require.NoError(t, err)
+		err = client.SyncWant(ctx, "test-unit", "dep-unit")
+		require.NoError(t, err)
+		client.Close()
+
+		var outBuf bytes.Buffer
+		inv, _ := clitest.New(t, "exp", "sync", "status", "test-unit", "--socket-path", path)
+		inv.Stdout = &outBuf
+		inv.Stderr = &outBuf
+
+		err = inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		clitest.TestGoldenFile(t, "TestSyncCommands_Golden/status_pending", outBuf.Bytes(), nil)
+	})
+
+	t.Run("status_started", func(t *testing.T) {
+		t.Parallel()
+		path, cleanup := setupSocketServer(t)
+		defer cleanup()
+
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		// Start a unit
+		client, err := agentsocket.NewClient(ctx, agentsocket.WithPath(path))
+		require.NoError(t, err)
+		err = client.SyncStart(ctx, "test-unit")
+		require.NoError(t, err)
+		client.Close()
+
+		var outBuf bytes.Buffer
+		inv, _ := clitest.New(t, "exp", "sync", "status", "test-unit", "--socket-path", path)
+		inv.Stdout = &outBuf
+		inv.Stderr = &outBuf
+
+		err = inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		clitest.TestGoldenFile(t, "TestSyncCommands_Golden/status_started", outBuf.Bytes(), nil)
+	})
+
+	t.Run("status_completed", func(t *testing.T) {
+		t.Parallel()
+		path, cleanup := setupSocketServer(t)
+		defer cleanup()
+
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		// Start and complete a unit
+		client, err := agentsocket.NewClient(ctx, agentsocket.WithPath(path))
+		require.NoError(t, err)
+		err = client.SyncStart(ctx, "test-unit")
+		require.NoError(t, err)
+		err = client.SyncComplete(ctx, "test-unit")
+		require.NoError(t, err)
+		client.Close()
+
+		var outBuf bytes.Buffer
+		inv, _ := clitest.New(t, "exp", "sync", "status", "test-unit", "--socket-path", path)
+		inv.Stdout = &outBuf
+		inv.Stderr = &outBuf
+
+		err = inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		clitest.TestGoldenFile(t, "TestSyncCommands_Golden/status_completed", outBuf.Bytes(), nil)
+	})
+
+	t.Run("status_with_dependencies", func(t *testing.T) {
+		t.Parallel()
+		path, cleanup := setupSocketServer(t)
+		defer cleanup()
+
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		// Set up a unit with dependencies, some satisfied, some not
+		client, err := agentsocket.NewClient(ctx, agentsocket.WithPath(path))
+		require.NoError(t, err)
+		err = client.SyncWant(ctx, "test-unit", "dep-1")
+		require.NoError(t, err)
+		err = client.SyncWant(ctx, "test-unit", "dep-2")
+		require.NoError(t, err)
+		// Complete dep-1, leave dep-2 incomplete
+		err = client.SyncStart(ctx, "dep-1")
+		require.NoError(t, err)
+		err = client.SyncComplete(ctx, "dep-1")
+		require.NoError(t, err)
+		client.Close()
+
+		var outBuf bytes.Buffer
+		inv, _ := clitest.New(t, "exp", "sync", "status", "test-unit", "--socket-path", path)
+		inv.Stdout = &outBuf
+		inv.Stderr = &outBuf
+
+		err = inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		clitest.TestGoldenFile(t, "TestSyncCommands_Golden/status_with_dependencies", outBuf.Bytes(), nil)
+	})
+
+	t.Run("status_json_format", func(t *testing.T) {
+		t.Parallel()
+		path, cleanup := setupSocketServer(t)
+		defer cleanup()
+
+		ctx := testutil.Context(t, testutil.WaitShort)
+
+		// Set up a unit with dependencies
+		client, err := agentsocket.NewClient(ctx, agentsocket.WithPath(path))
+		require.NoError(t, err)
+		err = client.SyncWant(ctx, "test-unit", "dep-unit")
+		require.NoError(t, err)
+		err = client.SyncStart(ctx, "dep-unit")
+		require.NoError(t, err)
+		err = client.SyncComplete(ctx, "dep-unit")
+		require.NoError(t, err)
+		client.Close()
+
+		var outBuf bytes.Buffer
+		inv, _ := clitest.New(t, "exp", "sync", "status", "test-unit", "--output", "json", "--socket-path", path)
+		inv.Stdout = &outBuf
+		inv.Stderr = &outBuf
+
+		err = inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		clitest.TestGoldenFile(t, "TestSyncCommands_Golden/status_json_format", outBuf.Bytes(), nil)
+	})
+}
@@ -0,0 +1,49 @@
+package cli
+
+import (
+	"golang.org/x/xerrors"
+
+	"github.com/coder/serpent"
+
+	"github.com/coder/coder/v2/agent/agentsocket"
+	"github.com/coder/coder/v2/agent/unit"
+	"github.com/coder/coder/v2/cli/cliui"
+)
+
+func (*RootCmd) syncWant(socketPath *string) *serpent.Command {
+	cmd := &serpent.Command{
+		Use:   "want <unit> <depends-on>",
+		Short: "Declare that a unit depends on another unit completing before it can start",
+		Long:  "Declare that a unit depends on another unit completing before it can start. The unit specified first will not start until the second has signaled that it has completed.",
+		Handler: func(i *serpent.Invocation) error {
+			ctx := i.Context()
+
+			if len(i.Args) != 2 {
+				return xerrors.New("exactly two arguments are required: unit and depends-on")
+			}
+			dependentUnit := unit.ID(i.Args[0])
+			dependsOn := unit.ID(i.Args[1])
+
+			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.SyncWant(ctx, dependentUnit, dependsOn); err != nil {
+				return xerrors.Errorf("declare dependency failed: %w", err)
+			}
+
+			cliui.Info(i.Stdout, "Success")
+
+			return nil
+		},
+	}
+
+	return cmd
+}
@@ -8,7 +8,7 @@ func (r *RootCmd) tasksCommand() *serpent.Command {
 	cmd := &serpent.Command{
 		Use:     "task",
 		Aliases: []string{"tasks"},
-		Short:   "Experimental task commands.",
+		Short:   "Manage tasks",
 		Handler: func(i *serpent.Invocation) error {
 			return i.Command.HelpHandler(i)
 		},
@@ -28,27 +28,27 @@ func (r *RootCmd) taskCreate() *serpent.Command {

 	cmd := &serpent.Command{
 		Use:   "create [input]",
-		Short: "Create an experimental task",
+		Short: "Create a task",
 		Long: FormatExamples(
 			Example{
 				Description: "Create a task with direct input",
-				Command:     "coder exp task create \"Add authentication to the user service\"",
+				Command:     "coder task create \"Add authentication to the user service\"",
 			},
 			Example{
 				Description: "Create a task with stdin input",
-				Command:     "echo \"Add authentication to the user service\" | coder exp task create",
+				Command:     "echo \"Add authentication to the user service\" | coder task create",
 			},
 			Example{
 				Description: "Create a task with a specific name",
-				Command:     "coder exp task create --name task1 \"Add authentication to the user service\"",
+				Command:     "coder task create --name task1 \"Add authentication to the user service\"",
 			},
 			Example{
 				Description: "Create a task from a specific template / preset",
-				Command:     "coder exp task create --template backend-dev --preset \"My Preset\" \"Add authentication to the user service\"",
+				Command:     "coder task create --template backend-dev --preset \"My Preset\" \"Add authentication to the user service\"",
 			},
 			Example{
 				Description: "Create a task for another user (requires appropriate permissions)",
-				Command:     "coder exp task create --owner user@example.com \"Add authentication to the user service\"",
+				Command:     "coder task create --owner user@example.com \"Add authentication to the user service\"",
 			},
 		),
 		Middleware: serpent.Chain(
@@ -111,8 +111,7 @@ func (r *RootCmd) taskCreate() *serpent.Command {
 			}

 			var (
-				ctx       = inv.Context()
-				expClient = codersdk.NewExperimentalClient(client)
+				ctx = inv.Context()

 				taskInput               string
 				templateVersionID       uuid.UUID
@@ -208,7 +207,7 @@ func (r *RootCmd) taskCreate() *serpent.Command {
 				templateVersionPresetID = preset.ID
 			}

-			task, err := expClient.CreateTask(ctx, ownerArg, codersdk.CreateTaskRequest{
+			task, err := client.CreateTask(ctx, ownerArg, codersdk.CreateTaskRequest{
 				Name:                    taskName,
 				TemplateVersionID:       templateVersionID,
 				TemplateVersionPresetID: templateVersionPresetID,
@@ -69,7 +69,7 @@ func TestTaskCreate(t *testing.T) {
 						ActiveVersionID: templateVersionID,
 					},
 				})
-			case fmt.Sprintf("/api/experimental/tasks/%s", username):
+			case fmt.Sprintf("/api/v2/tasks/%s", username):
 				var req codersdk.CreateTaskRequest
 				if !httpapi.Read(ctx, w, r, &req) {
 					return
@@ -329,7 +329,7 @@ func TestTaskCreate(t *testing.T) {
 				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", "create"}
+				args   = []string{"task", "create"}
 				sb     strings.Builder
 				err    error
 			)
@@ -17,19 +17,19 @@ import (
 func (r *RootCmd) taskDelete() *serpent.Command {
 	cmd := &serpent.Command{
 		Use:   "delete <task> [<task> ...]",
-		Short: "Delete experimental tasks",
+		Short: "Delete tasks",
 		Long: FormatExamples(
 			Example{
 				Description: "Delete a single task.",
-				Command:     "$ coder exp task delete task1",
+				Command:     "$ coder task delete task1",
 			},
 			Example{
 				Description: "Delete multiple tasks.",
-				Command:     "$ coder exp task delete task1 task2 task3",
+				Command:     "$ coder task delete task1 task2 task3",
 			},
 			Example{
 				Description: "Delete a task without confirmation.",
-				Command:     "$ coder exp task delete task4 --yes",
+				Command:     "$ coder task delete task4 --yes",
 			},
 		),
 		Middleware: serpent.Chain(
@@ -44,11 +44,10 @@ func (r *RootCmd) taskDelete() *serpent.Command {
 			if err != nil {
 				return err
 			}
-			exp := codersdk.NewExperimentalClient(client)

 			var tasks []codersdk.Task
 			for _, identifier := range inv.Args {
-				task, err := exp.TaskByIdentifier(ctx, identifier)
+				task, err := client.TaskByIdentifier(ctx, identifier)
 				if err != nil {
 					return xerrors.Errorf("resolve task %q: %w", identifier, err)
 				}
@@ -71,7 +70,7 @@ func (r *RootCmd) taskDelete() *serpent.Command {

 			for i, task := range tasks {
 				display := displayList[i]
-				if err := exp.DeleteTask(ctx, task.OwnerName, task.ID); err != nil {
+				if err := client.DeleteTask(ctx, task.OwnerName, task.ID); err != nil {
 					return xerrors.Errorf("delete task %q: %w", display, err)
 				}
 				_, _ = fmt.Fprintln(
@@ -56,7 +56,7 @@ func TestExpTaskDelete(t *testing.T) {
 				taskID := uuid.MustParse(id1)
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch {
-					case r.Method == http.MethodGet && r.URL.Path == "/api/experimental/tasks/me/exists":
+					case r.Method == http.MethodGet && r.URL.Path == "/api/v2/tasks/me/exists":
 						c.nameResolves.Add(1)
 						httpapi.Write(r.Context(), w, http.StatusOK,
 							codersdk.Task{
@@ -64,7 +64,7 @@ func TestExpTaskDelete(t *testing.T) {
 								Name:      "exists",
 								OwnerName: "me",
 							})
-					case r.Method == http.MethodDelete && r.URL.Path == "/api/experimental/tasks/me/"+id1:
+					case r.Method == http.MethodDelete && r.URL.Path == "/api/v2/tasks/me/"+id1:
 						c.deleteCalls.Add(1)
 						w.WriteHeader(http.StatusAccepted)
 					default:
@@ -82,13 +82,13 @@ func TestExpTaskDelete(t *testing.T) {
 			buildHandler: func(c *testCounters) http.HandlerFunc {
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch {
-					case r.Method == http.MethodGet && r.URL.Path == "/api/experimental/tasks/me/"+id2:
+					case r.Method == http.MethodGet && r.URL.Path == "/api/v2/tasks/me/"+id2:
 						httpapi.Write(r.Context(), w, http.StatusOK, codersdk.Task{
 							ID:        uuid.MustParse(id2),
 							OwnerName: "me",
 							Name:      "uuid-task",
 						})
-					case r.Method == http.MethodDelete && r.URL.Path == "/api/experimental/tasks/me/"+id2:
+					case r.Method == http.MethodDelete && r.URL.Path == "/api/v2/tasks/me/"+id2:
 						c.deleteCalls.Add(1)
 						w.WriteHeader(http.StatusAccepted)
 					default:
@@ -104,24 +104,24 @@ func TestExpTaskDelete(t *testing.T) {
 			buildHandler: func(c *testCounters) http.HandlerFunc {
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch {
-					case r.Method == http.MethodGet && r.URL.Path == "/api/experimental/tasks/me/first":
+					case r.Method == http.MethodGet && r.URL.Path == "/api/v2/tasks/me/first":
 						c.nameResolves.Add(1)
 						httpapi.Write(r.Context(), w, http.StatusOK, codersdk.Task{
 							ID:        uuid.MustParse(id3),
 							Name:      "first",
 							OwnerName: "me",
 						})
-					case r.Method == http.MethodGet && r.URL.Path == "/api/experimental/tasks/me/"+id4:
+					case r.Method == http.MethodGet && r.URL.Path == "/api/v2/tasks/me/"+id4:
 						c.nameResolves.Add(1)
 						httpapi.Write(r.Context(), w, http.StatusOK, codersdk.Task{
 							ID:        uuid.MustParse(id4),
 							OwnerName: "me",
 							Name:      "uuid-task-4",
 						})
-					case r.Method == http.MethodDelete && r.URL.Path == "/api/experimental/tasks/me/"+id3:
+					case r.Method == http.MethodDelete && r.URL.Path == "/api/v2/tasks/me/"+id3:
 						c.deleteCalls.Add(1)
 						w.WriteHeader(http.StatusAccepted)
-					case r.Method == http.MethodDelete && r.URL.Path == "/api/experimental/tasks/me/"+id4:
+					case r.Method == http.MethodDelete && r.URL.Path == "/api/v2/tasks/me/"+id4:
 						c.deleteCalls.Add(1)
 						w.WriteHeader(http.StatusAccepted)
 					default:
@@ -140,7 +140,7 @@ func TestExpTaskDelete(t *testing.T) {
 			buildHandler: func(_ *testCounters) http.HandlerFunc {
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch {
-					case r.Method == http.MethodGet && r.URL.Path == "/api/experimental/tasks" && r.URL.Query().Get("q") == "owner:\"me\"":
+					case r.Method == http.MethodGet && r.URL.Path == "/api/v2/tasks" && r.URL.Query().Get("q") == "owner:\"me\"":
 						httpapi.Write(r.Context(), w, http.StatusOK, struct {
 							Tasks []codersdk.Task `json:"tasks"`
 							Count int             `json:"count"`
@@ -163,14 +163,14 @@ func TestExpTaskDelete(t *testing.T) {
 				taskID := uuid.MustParse(id5)
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch {
-					case r.Method == http.MethodGet && r.URL.Path == "/api/experimental/tasks/me/bad":
+					case r.Method == http.MethodGet && r.URL.Path == "/api/v2/tasks/me/bad":
 						c.nameResolves.Add(1)
 						httpapi.Write(r.Context(), w, http.StatusOK, codersdk.Task{
 							ID:        taskID,
 							Name:      "bad",
 							OwnerName: "me",
 						})
-					case r.Method == http.MethodDelete && r.URL.Path == "/api/experimental/tasks/me/bad":
+					case r.Method == http.MethodDelete && r.URL.Path == "/api/v2/tasks/me/bad":
 						httpapi.InternalServerError(w, xerrors.New("boom"))
 					default:
 						httpapi.InternalServerError(w, xerrors.New("unwanted path: "+r.Method+" "+r.URL.Path))
@@ -193,7 +193,7 @@ func TestExpTaskDelete(t *testing.T) {

 			client := codersdk.New(testutil.MustURL(t, srv.URL))

-			args := append([]string{"exp", "task", "delete"}, tc.args...)
+			args := append([]string{"task", "delete"}, tc.args...)
 			inv, root := clitest.New(t, args...)
 			inv = inv.WithContext(ctx)
 			clitest.SetupConfig(t, client, root)
@@ -69,27 +69,27 @@ func (r *RootCmd) taskList() *serpent.Command {

 	cmd := &serpent.Command{
 		Use:   "list",
-		Short: "List experimental tasks",
+		Short: "List tasks",
 		Long: FormatExamples(
 			Example{
 				Description: "List tasks for the current user.",
-				Command:     "coder exp task list",
+				Command:     "coder task list",
 			},
 			Example{
 				Description: "List tasks for a specific user.",
-				Command:     "coder exp task list --user someone-else",
+				Command:     "coder task list --user someone-else",
 			},
 			Example{
 				Description: "List all tasks you can view.",
-				Command:     "coder exp task list --all",
+				Command:     "coder task list --all",
 			},
 			Example{
 				Description: "List all your running tasks.",
-				Command:     "coder exp task list --status running",
+				Command:     "coder task list --status running",
 			},
 			Example{
 				Description: "As above, but only show IDs.",
-				Command:     "coder exp task list --status running --quiet",
+				Command:     "coder task list --status running --quiet",
 			},
 		),
 		Aliases: []string{"ls"},
@@ -135,14 +135,13 @@ func (r *RootCmd) taskList() *serpent.Command {
 			}

 			ctx := inv.Context()
-			exp := codersdk.NewExperimentalClient(client)

 			targetUser := strings.TrimSpace(user)
 			if targetUser == "" && !all {
 				targetUser = codersdk.Me
 			}

-			tasks, err := exp.Tasks(ctx, &codersdk.TasksFilter{
+			tasks, err := client.Tasks(ctx, &codersdk.TasksFilter{
 				Owner:  targetUser,
 				Status: codersdk.TaskStatus(statusFilter),
 			})
@@ -69,7 +69,7 @@ func TestExpTaskList(t *testing.T) {
 		owner := coderdtest.CreateFirstUser(t, client)
 		memberClient, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)

-		inv, root := clitest.New(t, "exp", "task", "list")
+		inv, root := clitest.New(t, "task", "list")
 		clitest.SetupConfig(t, memberClient, root)

 		pty := ptytest.New(t).Attach(inv)
@@ -93,7 +93,7 @@ func TestExpTaskList(t *testing.T) {
 		wantPrompt := "build me a web app"
 		task := makeAITask(t, db, owner.OrganizationID, owner.UserID, memberUser.ID, database.WorkspaceTransitionStart, wantPrompt)

-		inv, root := clitest.New(t, "exp", "task", "list", "--column", "id,name,status,initial prompt")
+		inv, root := clitest.New(t, "task", "list", "--column", "id,name,status,initial prompt")
 		clitest.SetupConfig(t, memberClient, root)

 		pty := ptytest.New(t).Attach(inv)
@@ -122,7 +122,7 @@ func TestExpTaskList(t *testing.T) {
 		pausedTask := makeAITask(t, db, owner.OrganizationID, owner.UserID, memberUser.ID, database.WorkspaceTransitionStop, "stop me please")

 		// Use JSON output to reliably validate filtering.
-		inv, root := clitest.New(t, "exp", "task", "list", "--status=paused", "--output=json")
+		inv, root := clitest.New(t, "task", "list", "--status=paused", "--output=json")
 		clitest.SetupConfig(t, memberClient, root)

 		ctx := testutil.Context(t, testutil.WaitShort)
@@ -153,7 +153,7 @@ func TestExpTaskList(t *testing.T) {
 		_ = makeAITask(t, db, owner.OrganizationID, owner.UserID, memberUser.ID, database.WorkspaceTransitionStart, "other-task")
 		task := makeAITask(t, db, owner.OrganizationID, owner.UserID, owner.UserID, database.WorkspaceTransitionStart, "me-task")

-		inv, root := clitest.New(t, "exp", "task", "list", "--user", "me")
+		inv, root := clitest.New(t, "task", "list", "--user", "me")
 		//nolint:gocritic // Owner client is intended here smoke test the member task not showing up.
 		clitest.SetupConfig(t, client, root)

@@ -180,7 +180,7 @@ func TestExpTaskList(t *testing.T) {
 		task2 := makeAITask(t, db, owner.OrganizationID, owner.UserID, memberUser.ID, database.WorkspaceTransitionStop, "stop me please")

 		// Given: We add the `--quiet` flag
-		inv, root := clitest.New(t, "exp", "task", "list", "--quiet")
+		inv, root := clitest.New(t, "task", "list", "--quiet")
 		clitest.SetupConfig(t, memberClient, root)

 		ctx := testutil.Context(t, testutil.WaitShort)
@@ -224,7 +224,7 @@ func TestExpTaskList_OwnerCanListOthers(t *testing.T) {
 		t.Parallel()

 		// As the owner, list only member A tasks.
-		inv, root := clitest.New(t, "exp", "task", "list", "--user", memberAUser.Username, "--output=json")
+		inv, root := clitest.New(t, "task", "list", "--user", memberAUser.Username, "--output=json")
 		//nolint:gocritic // Owner client is intended here to allow member tasks to be listed.
 		clitest.SetupConfig(t, ownerClient, root)

@@ -252,7 +252,7 @@ func TestExpTaskList_OwnerCanListOthers(t *testing.T) {

 		// As the owner, list all tasks to verify both member tasks are present.
 		// Use JSON output to reliably validate filtering.
-		inv, root := clitest.New(t, "exp", "task", "list", "--all", "--output=json")
+		inv, root := clitest.New(t, "task", "list", "--all", "--output=json")
 		//nolint:gocritic // Owner client is intended here to allow all tasks to be listed.
 		clitest.SetupConfig(t, ownerClient, root)

@@ -28,7 +28,7 @@ func (r *RootCmd) taskLogs() *serpent.Command {
 		Long: FormatExamples(
 			Example{
 				Description: "Show logs for a given task.",
-				Command:     "coder exp task logs task1",
+				Command:     "coder task logs task1",
 			}),
 		Middleware: serpent.Chain(
 			serpent.RequireNArgs(1),
@@ -41,16 +41,15 @@ func (r *RootCmd) taskLogs() *serpent.Command {

 			var (
 				ctx        = inv.Context()
-				exp        = codersdk.NewExperimentalClient(client)
 				identifier = inv.Args[0]
 			)

-			task, err := exp.TaskByIdentifier(ctx, identifier)
+			task, err := client.TaskByIdentifier(ctx, identifier)
 			if err != nil {
 				return xerrors.Errorf("resolve task %q: %w", identifier, err)
 			}

-			logs, err := exp.TaskLogs(ctx, codersdk.Me, task.ID)
+			logs, err := client.TaskLogs(ctx, codersdk.Me, task.ID)
 			if err != nil {
 				return xerrors.Errorf("get task logs: %w", err)
 			}
@@ -46,7 +46,7 @@ func Test_TaskLogs(t *testing.T) {
 		userClient := client // user already has access to their own workspace

 		var stdout strings.Builder
-		inv, root := clitest.New(t, "exp", "task", "logs", task.Name, "--output", "json")
+		inv, root := clitest.New(t, "task", "logs", task.Name, "--output", "json")
 		inv.Stdout = &stdout
 		clitest.SetupConfig(t, userClient, root)

@@ -72,7 +72,7 @@ func Test_TaskLogs(t *testing.T) {
 		userClient := client

 		var stdout strings.Builder
-		inv, root := clitest.New(t, "exp", "task", "logs", task.ID.String(), "--output", "json")
+		inv, root := clitest.New(t, "task", "logs", task.ID.String(), "--output", "json")
 		inv.Stdout = &stdout
 		clitest.SetupConfig(t, userClient, root)

@@ -98,7 +98,7 @@ func Test_TaskLogs(t *testing.T) {
 		userClient := client

 		var stdout strings.Builder
-		inv, root := clitest.New(t, "exp", "task", "logs", task.ID.String())
+		inv, root := clitest.New(t, "task", "logs", task.ID.String())
 		inv.Stdout = &stdout
 		clitest.SetupConfig(t, userClient, root)

@@ -121,7 +121,7 @@ func Test_TaskLogs(t *testing.T) {
 		userClient, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)

 		var stdout strings.Builder
-		inv, root := clitest.New(t, "exp", "task", "logs", "doesnotexist")
+		inv, root := clitest.New(t, "task", "logs", "doesnotexist")
 		inv.Stdout = &stdout
 		clitest.SetupConfig(t, userClient, root)

@@ -139,7 +139,7 @@ func Test_TaskLogs(t *testing.T) {
 		userClient, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)

 		var stdout strings.Builder
-		inv, root := clitest.New(t, "exp", "task", "logs", uuid.Nil.String())
+		inv, root := clitest.New(t, "task", "logs", uuid.Nil.String())
 		inv.Stdout = &stdout
 		clitest.SetupConfig(t, userClient, root)

@@ -155,7 +155,7 @@ func Test_TaskLogs(t *testing.T) {
 		client, task := setupCLITaskTest(ctx, t, fakeAgentAPITaskLogsErr(assert.AnError))
 		userClient := client

-		inv, root := clitest.New(t, "exp", "task", "logs", task.ID.String())
+		inv, root := clitest.New(t, "task", "logs", task.ID.String())
 		clitest.SetupConfig(t, userClient, root)

 		err := inv.WithContext(ctx).Run()
@@ -17,10 +17,10 @@ func (r *RootCmd) taskSend() *serpent.Command {
 		Short: "Send input to a task",
 		Long: FormatExamples(Example{
 			Description: "Send direct input to a task.",
-			Command:     "coder exp task send task1 \"Please also add unit tests\"",
+			Command:     "coder task send task1 \"Please also add unit tests\"",
 		}, Example{
 			Description: "Send input from stdin to a task.",
-			Command:     "echo \"Please also add unit tests\" | coder exp task send task1 --stdin",
+			Command:     "echo \"Please also add unit tests\" | coder task send task1 --stdin",
 		}),
 		Middleware: serpent.RequireRangeArgs(1, 2),
 		Options: serpent.OptionSet{
@@ -39,7 +39,6 @@ func (r *RootCmd) taskSend() *serpent.Command {

 			var (
 				ctx        = inv.Context()
-				exp        = codersdk.NewExperimentalClient(client)
 				identifier = inv.Args[0]

 				taskInput string
@@ -60,12 +59,12 @@ func (r *RootCmd) taskSend() *serpent.Command {
 				taskInput = inv.Args[1]
 			}

-			task, err := exp.TaskByIdentifier(ctx, identifier)
+			task, err := client.TaskByIdentifier(ctx, identifier)
 			if err != nil {
 				return xerrors.Errorf("resolve task: %w", err)
 			}

-			if err = exp.TaskSend(ctx, codersdk.Me, task.ID, codersdk.TaskSendRequest{Input: taskInput}); err != nil {
+			if err = client.TaskSend(ctx, codersdk.Me, task.ID, codersdk.TaskSendRequest{Input: taskInput}); err != nil {
 				return xerrors.Errorf("send input to task: %w", err)
 			}

@@ -30,7 +30,7 @@ func Test_TaskSend(t *testing.T) {
 		userClient := client

 		var stdout strings.Builder
-		inv, root := clitest.New(t, "exp", "task", "send", task.Name, "carry on with the task")
+		inv, root := clitest.New(t, "task", "send", task.Name, "carry on with the task")
 		inv.Stdout = &stdout
 		clitest.SetupConfig(t, userClient, root)

@@ -46,7 +46,7 @@ func Test_TaskSend(t *testing.T) {
 		userClient := client

 		var stdout strings.Builder
-		inv, root := clitest.New(t, "exp", "task", "send", task.ID.String(), "carry on with the task")
+		inv, root := clitest.New(t, "task", "send", task.ID.String(), "carry on with the task")
 		inv.Stdout = &stdout
 		clitest.SetupConfig(t, userClient, root)

@@ -62,7 +62,7 @@ func Test_TaskSend(t *testing.T) {
 		userClient := client

 		var stdout strings.Builder
-		inv, root := clitest.New(t, "exp", "task", "send", task.Name, "--stdin")
+		inv, root := clitest.New(t, "task", "send", task.Name, "--stdin")
 		inv.Stdout = &stdout
 		inv.Stdin = strings.NewReader("carry on with the task")
 		clitest.SetupConfig(t, userClient, root)
@@ -80,7 +80,7 @@ func Test_TaskSend(t *testing.T) {
 		userClient, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)

 		var stdout strings.Builder
-		inv, root := clitest.New(t, "exp", "task", "send", "doesnotexist", "some task input")
+		inv, root := clitest.New(t, "task", "send", "doesnotexist", "some task input")
 		inv.Stdout = &stdout
 		clitest.SetupConfig(t, userClient, root)

@@ -98,7 +98,7 @@ func Test_TaskSend(t *testing.T) {
 		userClient, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)

 		var stdout strings.Builder
-		inv, root := clitest.New(t, "exp", "task", "send", uuid.Nil.String(), "some task input")
+		inv, root := clitest.New(t, "task", "send", uuid.Nil.String(), "some task input")
 		inv.Stdout = &stdout
 		clitest.SetupConfig(t, userClient, root)

@@ -114,7 +114,7 @@ func Test_TaskSend(t *testing.T) {
 		userClient, task := setupCLITaskTest(ctx, t, fakeAgentAPITaskSendErr(t, assert.AnError))

 		var stdout strings.Builder
-		inv, root := clitest.New(t, "exp", "task", "send", task.Name, "some task input")
+		inv, root := clitest.New(t, "task", "send", task.Name, "some task input")
 		inv.Stdout = &stdout
 		clitest.SetupConfig(t, userClient, root)

@@ -47,11 +47,11 @@ func (r *RootCmd) taskStatus() *serpent.Command {
 		Long: FormatExamples(
 			Example{
 				Description: "Show the status of a given task.",
-				Command:     "coder exp task status task1",
+				Command:     "coder task status task1",
 			},
 			Example{
 				Description: "Watch the status of a given task until it completes (idle or stopped).",
-				Command:     "coder exp task status task1 --watch",
+				Command:     "coder task status task1 --watch",
 			},
 		),
 		Use:     "status",
@@ -83,10 +83,9 @@ func (r *RootCmd) taskStatus() *serpent.Command {
 			}

 			ctx := i.Context()
-			exp := codersdk.NewExperimentalClient(client)
 			identifier := i.Args[0]

-			task, err := exp.TaskByIdentifier(ctx, identifier)
+			task, err := client.TaskByIdentifier(ctx, identifier)
 			if err != nil {
 				return err
 			}
@@ -107,7 +106,7 @@ func (r *RootCmd) taskStatus() *serpent.Command {
 			// TODO: implement streaming updates instead of polling
 			lastStatusRow := tsr
 			for range t.C {
-				task, err := exp.TaskByID(ctx, task.ID)
+				task, err := client.TaskByID(ctx, task.ID)
 				if err != nil {
 					return err
 				}
@@ -36,7 +36,7 @@ func Test_TaskStatus(t *testing.T) {
 			hf: func(ctx context.Context, _ time.Time) func(w http.ResponseWriter, r *http.Request) {
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch r.URL.Path {
-					case "/api/experimental/tasks/me/doesnotexist":
+					case "/api/v2/tasks/me/doesnotexist":
 						httpapi.ResourceNotFound(w)
 						return
 					default:
@@ -52,7 +52,7 @@ func Test_TaskStatus(t *testing.T) {
 			hf: func(ctx context.Context, now time.Time) func(w http.ResponseWriter, r *http.Request) {
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch r.URL.Path {
-					case "/api/experimental/tasks/me/exists":
+					case "/api/v2/tasks/me/exists":
 						httpapi.Write(ctx, w, http.StatusOK, codersdk.Task{
 							ID:              uuid.MustParse("11111111-1111-1111-1111-111111111111"),
 							WorkspaceStatus: codersdk.WorkspaceStatusRunning,
@@ -88,7 +88,7 @@ func Test_TaskStatus(t *testing.T) {
 				var calls atomic.Int64
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch r.URL.Path {
-					case "/api/experimental/tasks/me/exists":
+					case "/api/v2/tasks/me/exists":
 						httpapi.Write(ctx, w, http.StatusOK, codersdk.Task{
 							ID:              uuid.MustParse("11111111-1111-1111-1111-111111111111"),
 							Name:            "exists",
@@ -103,7 +103,7 @@ func Test_TaskStatus(t *testing.T) {
 							Status:                  codersdk.TaskStatusPending,
 						})
 						return
-					case "/api/experimental/tasks/me/11111111-1111-1111-1111-111111111111":
+					case "/api/v2/tasks/me/11111111-1111-1111-1111-111111111111":
 						defer calls.Add(1)
 						switch calls.Load() {
 						case 0:
@@ -189,6 +189,7 @@ func Test_TaskStatus(t *testing.T) {
  "owner_id": "00000000-0000-0000-0000-000000000000",
  "owner_name": "me",
  "name": "exists",
+  "display_name": "Task exists",
  "template_id": "00000000-0000-0000-0000-000000000000",
  "template_version_id": "00000000-0000-0000-0000-000000000000",
  "template_name": "",
@@ -218,11 +219,12 @@ func Test_TaskStatus(t *testing.T) {
 				ts := time.Date(2025, 8, 26, 12, 34, 56, 0, time.UTC)
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch r.URL.Path {
-					case "/api/experimental/tasks/me/exists":
+					case "/api/v2/tasks/me/exists":
 						httpapi.Write(ctx, w, http.StatusOK, codersdk.Task{
-							ID:        uuid.MustParse("11111111-1111-1111-1111-111111111111"),
-							Name:      "exists",
-							OwnerName: "me",
+							ID:          uuid.MustParse("11111111-1111-1111-1111-111111111111"),
+							Name:        "exists",
+							DisplayName: "Task exists",
+							OwnerName:   "me",
 							WorkspaceAgentHealth: &codersdk.WorkspaceAgentHealth{
 								Healthy: true,
 							},
@@ -254,7 +256,7 @@ func Test_TaskStatus(t *testing.T) {
 				srv    = httptest.NewServer(http.HandlerFunc(tc.hf(ctx, now)))
 				client = codersdk.New(testutil.MustURL(t, srv.URL))
 				sb     = strings.Builder{}
-				args   = []string{"exp", "task", "status", "--watch-interval", testutil.IntervalFast.String()}
+				args   = []string{"task", "status", "--watch-interval", testutil.IntervalFast.String()}
 			)

 			t.Cleanup(srv.Close)
@@ -60,14 +60,14 @@ func Test_Tasks(t *testing.T) {
 	}{
 		{
 			name:    "create task",
-			cmdArgs: []string{"exp", "task", "create", "test task input for " + t.Name(), "--name", taskName, "--template", taskTpl.Name},
+			cmdArgs: []string{"task", "create", "test task input for " + t.Name(), "--name", taskName, "--template", taskTpl.Name},
 			assertFn: func(stdout string, userClient *codersdk.Client) {
 				require.Contains(t, stdout, taskName, "task name should be in output")
 			},
 		},
 		{
 			name:    "list tasks after create",
-			cmdArgs: []string{"exp", "task", "list", "--output", "json"},
+			cmdArgs: []string{"task", "list", "--output", "json"},
 			assertFn: func(stdout string, userClient *codersdk.Client) {
 				var tasks []codersdk.Task
 				err := json.NewDecoder(strings.NewReader(stdout)).Decode(&tasks)
@@ -88,7 +88,7 @@ func Test_Tasks(t *testing.T) {
 		},
 		{
 			name:    "get task status after create",
-			cmdArgs: []string{"exp", "task", "status", taskName, "--output", "json"},
+			cmdArgs: []string{"task", "status", taskName, "--output", "json"},
 			assertFn: func(stdout string, userClient *codersdk.Client) {
 				var task codersdk.Task
 				require.NoError(t, json.NewDecoder(strings.NewReader(stdout)).Decode(&task), "should unmarshal task status")
@@ -98,12 +98,12 @@ func Test_Tasks(t *testing.T) {
 		},
 		{
 			name:    "send task message",
-			cmdArgs: []string{"exp", "task", "send", taskName, "hello"},
+			cmdArgs: []string{"task", "send", taskName, "hello"},
 			// Assertions for this happen in the fake agent API handler.
 		},
 		{
 			name:    "read task logs",
-			cmdArgs: []string{"exp", "task", "logs", taskName, "--output", "json"},
+			cmdArgs: []string{"task", "logs", taskName, "--output", "json"},
 			assertFn: func(stdout string, userClient *codersdk.Client) {
 				var logs []codersdk.TaskLogEntry
 				require.NoError(t, json.NewDecoder(strings.NewReader(stdout)).Decode(&logs), "should unmarshal task logs")
@@ -118,12 +118,11 @@ func Test_Tasks(t *testing.T) {
 		},
 		{
 			name:    "delete task",
-			cmdArgs: []string{"exp", "task", "delete", taskName, "--yes"},
+			cmdArgs: []string{"task", "delete", taskName, "--yes"},
 			assertFn: func(stdout string, userClient *codersdk.Client) {
 				// The task should eventually no longer show up in the list of tasks
 				testutil.Eventually(ctx, t, func(ctx context.Context) bool {
-					expClient := codersdk.NewExperimentalClient(userClient)
-					tasks, err := expClient.Tasks(ctx, &codersdk.TasksFilter{})
+					tasks, err := userClient.Tasks(ctx, &codersdk.TasksFilter{})
 					if !assert.NoError(t, err) {
 						return false
 					}
@@ -248,8 +247,7 @@ func setupCLITaskTest(ctx context.Context, t *testing.T, agentAPIHandlers map[st
 	template := createAITaskTemplate(t, client, owner.OrganizationID, withSidebarURL(fakeAPI.URL()), withAgentToken(authToken))

 	wantPrompt := "test prompt"
-	exp := codersdk.NewExperimentalClient(userClient)
-	task, err := exp.CreateTask(ctx, codersdk.Me, codersdk.CreateTaskRequest{
+	task, err := userClient.CreateTask(ctx, codersdk.Me, codersdk.CreateTaskRequest{
 		TemplateVersionID: template.ActiveVersionID,
 		Input:             wantPrompt,
 		Name:              "test-task",
@@ -0,0 +1 @@
+Success
@@ -0,0 +1 @@
+Success
@@ -0,0 +1 @@
+Success
@@ -0,0 +1,2 @@
+Waiting for dependencies of unit 'test-unit' to be satisfied...
+Success
@@ -0,0 +1,6 @@
+Unit: test-unit
+Status: completed
+Ready: true
+
+Dependencies:
+No dependencies found
@@ -0,0 +1,13 @@
+{
+  "unit_name": "test-unit",
+  "status": "pending",
+  "is_ready": true,
+  "dependencies": [
+    {
+      "depends_on": "dep-unit",
+      "required_status": "completed",
+      "current_status": "completed",
+      "is_satisfied": true
+    }
+  ]
+}
@@ -0,0 +1,7 @@
+Unit: test-unit
+Status: pending
+Ready: false
+
+Dependencies:
+DEPENDS ON  REQUIRED STATUS  CURRENT STATUS  SATISFIED  
+dep-unit    completed        not registered  false      
@@ -0,0 +1,6 @@
+Unit: test-unit
+Status: started
+Ready: true
+
+Dependencies:
+No dependencies found
@@ -0,0 +1,8 @@
+Unit: test-unit
+Status: pending
+Ready: false
+
+Dependencies:
+DEPENDS ON  REQUIRED STATUS  CURRENT STATUS  SATISFIED  
+dep-1       completed        completed       true       
+dep-2       completed        not registered  false      
@@ -0,0 +1 @@
+Success
@@ -53,6 +53,7 @@ SUBCOMMANDS:
    stop              Stop a workspace
    support           Commands for troubleshooting issues with a Coder
                      deployment.
+    task              Manage tasks
    templates         Manage templates
    tokens            Manage personal access tokens
    unfavorite        Remove a workspace from your favorites
@@ -108,10 +109,12 @@ variables or flags.
      --url url, $CODER_URL
          URL to a deployment.

-      --use-keyring bool, $CODER_USE_KEYRING
+      --use-keyring bool, $CODER_USE_KEYRING (default: true)
          Store and retrieve session tokens using the operating system keyring.
-          Currently only supported on Windows. By default, tokens are stored in
-          plain text files.
+          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.

  -v, --verbose bool, $CODER_VERBOSE
          Enable verbose output.
@@ -67,6 +67,12 @@ OPTIONS:
      --script-data-dir string, $CODER_AGENT_SCRIPT_DATA_DIR (default: /tmp)
          Specify the location for storing script data.

+      --socket-path string, $CODER_AGENT_SOCKET_PATH
+          Specify the path for the agent socket.
+
+      --socket-server-enabled bool, $CODER_AGENT_SOCKET_SERVER_ENABLED (default: false)
+          Enable the agent socket server.
+
      --ssh-max-timeout duration, $CODER_AGENT_SSH_MAX_TIMEOUT (default: 72h)
          Specify the max timeout for a SSH connection, it is advisable to set
          it to a minimum of 60s, but no more than 72h.
@@ -0,0 +1,27 @@
+coder v0.0.0-devel
+
+USAGE:
+  coder exp sync [flags]
+
+  Manage unit dependencies for coordinated startup
+
+  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.
+
+SUBCOMMANDS:
+    complete    Mark a unit as complete
+    ping        Test agent socket connectivity and health
+    start       Wait until all unit dependencies are satisfied
+    status      Show unit status and dependency state
+    want        Declare that a unit depends on another unit completing before it
+                can start
+
+OPTIONS:
+      --socket-path string, $CODER_AGENT_SOCKET_PATH
+          Specify the path for the agent socket.
+
+———
+Run `coder --help` for a list of global options.
@@ -0,0 +1,12 @@
+coder v0.0.0-devel
+
+USAGE:
+  coder exp sync complete <unit>
+
+  Mark a unit as complete
+
+  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.
+
+———
+Run `coder --help` for a list of global options.
@@ -0,0 +1,13 @@
+coder v0.0.0-devel
+
+USAGE:
+  coder exp sync ping
+
+  Test agent socket connectivity and health
+
+  Test connectivity to the local Coder agent socket to verify the agent is
+  running and responsive. Useful for troubleshooting startup issues or verifying
+  the agent is accessible before running other sync commands.
+
+———
+Run `coder --help` for a list of global options.
@@ -0,0 +1,17 @@
+coder v0.0.0-devel
+
+USAGE:
+  coder exp sync start [flags] <unit>
+
+  Wait until all unit dependencies are satisfied
+
+  Wait until all dependencies are satisfied, consider the unit to have started,
+  then allow it to proceed. This command polls until dependencies are ready,
+  then marks the unit as started.
+
+OPTIONS:
+      --timeout duration (default: 5m)
+          Maximum time to wait for dependencies (e.g., 30s, 5m). 5m by default.
+
+———
+Run `coder --help` for a list of global options.
@@ -0,0 +1,20 @@
+coder v0.0.0-devel
+
+USAGE:
+  coder exp sync status [flags] <unit>
+
+  Show unit status and dependency state
+
+  Show the current status of a unit, whether it is ready to start, and lists its
+  dependencies. Shows which dependencies are satisfied and which are still
+  pending. Supports multiple output formats.
+
+OPTIONS:
+  -c, --column [depends on|required status|current status|satisfied] (default: depends on,required status,current status,satisfied)
+          Columns to display in table output.
+
+  -o, --output table|json (default: table)
+          Output format.
+
+———
+Run `coder --help` for a list of global options.
@@ -0,0 +1,13 @@
+coder v0.0.0-devel
+
+USAGE:
+  coder exp sync want <unit> <depends-on>
+
+  Declare that a unit depends on another unit completing before it can start
+
+  Declare that a unit depends on another unit completing before it can start.
+  The unit specified first will not start until the second has signaled that it
+  has completed.
+
+———
+Run `coder --help` for a list of global options.
@@ -5,9 +5,9 @@ USAGE:

  Authenticate with Coder deployment

-  By default, the session token is stored in a plain text file. Use the
-  --use-keyring flag or set CODER_USE_KEYRING=true to store the token in the
-  operating system keyring instead.
+  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.

 OPTIONS:
      --first-user-email string, $CODER_FIRST_USER_EMAIL
@@ -9,5 +9,9 @@ OPTIONS:
  -b, --build int
          Specify a workspace build to target by name. Defaults to latest.

+  -n, --no-build bool
+          Update the state without triggering a workspace build. Useful for
+          state-only migrations.
+
 ———
 Run `coder --help` for a list of global options.
@@ -0,0 +1,19 @@
+coder v0.0.0-devel
+
+USAGE:
+  coder task
+
+  Manage tasks
+
+  Aliases: tasks
+
+SUBCOMMANDS:
+    create    Create a task
+    delete    Delete tasks
+    list      List tasks
+    logs      Show a task's logs
+    send      Send input to a task
+    status    Show the status of a task.
+
+———
+Run `coder --help` for a list of global options.
@@ -0,0 +1,51 @@
+coder v0.0.0-devel
+
+USAGE:
+  coder task create [flags] [input]
+
+  Create a task
+
+    - Create a task with direct input:
+  
+       $ coder task create "Add authentication to the user service"
+  
+    - Create a task with stdin input:
+  
+       $ echo "Add authentication to the user service" | coder task create
+  
+    - Create a task with a specific name:
+  
+       $ coder task create --name task1 "Add authentication to the user service"
+  
+    - Create a task from a specific template / preset:
+  
+       $ coder task create --template backend-dev --preset "My Preset" "Add
+  authentication to the user service"
+  
+    - Create a task for another user (requires appropriate permissions):
+  
+       $ coder task create --owner user@example.com "Add authentication to the
+  user service"
+
+OPTIONS:
+  -O, --org string, $CODER_ORGANIZATION
+          Select which organization (uuid or name) to use.
+
+      --name string
+          Specify the name of the task. If you do not specify one, a name will
+          be generated for you.
+
+      --owner string (default: me)
+          Specify the owner of the task. Defaults to the current user.
+
+      --preset string, $CODER_TASK_PRESET_NAME (default: none)
+  -q, --quiet bool
+          Only display the created task's ID.
+
+      --stdin bool
+          Reads from stdin for the task input.
+
+      --template string, $CODER_TASK_TEMPLATE_NAME
+      --template-version string, $CODER_TASK_TEMPLATE_VERSION
+———
+Run `coder --help` for a list of global options.
@@ -0,0 +1,27 @@
+coder v0.0.0-devel
+
+USAGE:
+  coder task delete [flags] <task> [<task> ...]
+
+  Delete tasks
+
+  Aliases: rm
+
+    - Delete a single task.:
+  
+       $ $ coder task delete task1
+  
+    - Delete multiple tasks.:
+  
+       $ $ coder task delete task1 task2 task3
+  
+    - Delete a task without confirmation.:
+  
+       $ $ coder task delete task4 --yes
+
+OPTIONS:
+  -y, --yes bool
+          Bypass prompts.
+
+———
+Run `coder --help` for a list of global options.
@@ -0,0 +1,50 @@
+coder v0.0.0-devel
+
+USAGE:
+  coder task list [flags]
+
+  List tasks
+
+  Aliases: ls
+
+    - List tasks for the current user.:
+  
+       $ coder task list
+  
+    - List tasks for a specific user.:
+  
+       $ coder task list --user someone-else
+  
+    - List all tasks you can view.:
+  
+       $ coder task list --all
+  
+    - List all your running tasks.:
+  
+       $ coder task list --status running
+  
+    - As above, but only show IDs.:
+  
+       $ coder task list --status running --quiet
+
+OPTIONS:
+  -a, --all bool (default: false)
+          List tasks for all users you can view.
+
+  -c, --column [id|organization id|owner id|owner name|owner avatar url|name|display name|template id|template version id|template name|template display name|template icon|workspace id|workspace name|workspace status|workspace build number|workspace agent id|workspace agent lifecycle|workspace agent health|workspace app id|initial prompt|status|state|message|created at|updated at|state changed] (default: name,status,state,state changed,message)
+          Columns to display in table output.
+
+  -o, --output table|json (default: table)
+          Output format.
+
+  -q, --quiet bool (default: false)
+          Only display task IDs.
+
+      --status pending|initializing|active|paused|error|unknown
+          Filter by task status.
+
+      --user string
+          List tasks for the specified user (username, "me").
+
+———
+Run `coder --help` for a list of global options.
@@ -0,0 +1,20 @@
+coder v0.0.0-devel
+
+USAGE:
+  coder task logs [flags] <task>
+
+  Show a task's logs
+
+    - Show logs for a given task.:
+  
+       $ coder task logs task1
+
+OPTIONS:
+  -c, --column [id|content|type|time] (default: type,content)
+          Columns to display in table output.
+
+  -o, --output table|json (default: table)
+          Output format.
+
+———
+Run `coder --help` for a list of global options.
@@ -0,0 +1,21 @@
+coder v0.0.0-devel
+
+USAGE:
+  coder task send [flags] <task> [<input> | --stdin]
+
+  Send input to a task
+
+    - Send direct input to a task.:
+  
+       $ coder task send task1 "Please also add unit tests"
+  
+    - Send input from stdin to a task.:
+  
+       $ echo "Please also add unit tests" | coder task send task1 --stdin
+
+OPTIONS:
+      --stdin bool
+          Reads the input from stdin.
+
+———
+Run `coder --help` for a list of global options.
@@ -0,0 +1,30 @@
+coder v0.0.0-devel
+
+USAGE:
+  coder task status [flags]
+
+  Show the status of a task.
+
+  Aliases: stat
+
+    - Show the status of a given task.:
+  
+       $ coder task status task1
+  
+    - Watch the status of a given task until it completes (idle or stopped).:
+  
+       $ coder task status task1 --watch
+
+OPTIONS:
+  -c, --column [id|organization id|owner id|owner name|owner avatar url|name|display name|template id|template version id|template name|template display name|template icon|workspace id|workspace name|workspace status|workspace build number|workspace agent id|workspace agent lifecycle|workspace agent health|workspace app id|initial prompt|status|state|message|created at|updated at|state changed|healthy] (default: state changed,status,healthy,state,message)
+          Columns to display in table output.
+
+  -o, --output table|json (default: table)
+          Output format.
+
+      --watch bool (default: false)
+          Watch the task status output. This will stream updates to the terminal
+          until the underlying workspace is stopped.
+
+———
+Run `coder --help` for a list of global options.
@@ -36,6 +36,8 @@ import (
 	"github.com/coder/quartz"
 )

+const workspaceCacheRefreshInterval = 5 * time.Minute
+
 // API implements the DRPC agent API interface from agent/proto. This struct is
 // instantiated once per agent connection and kept alive for the duration of the
 // session.
@@ -54,6 +56,8 @@ type API struct {
 	*SubAgentAPI
 	*tailnet.DRPCService

+	cachedWorkspaceFields *CachedWorkspaceFields
+
 	mu sync.Mutex
 }

@@ -65,7 +69,7 @@ type Options struct {
 	WorkspaceID    uuid.UUID
 	OrganizationID uuid.UUID

-	Ctx                               context.Context
+	AuthenticatedCtx                  context.Context
 	Log                               slog.Logger
 	Clock                             quartz.Clock
 	Database                          database.Store
@@ -92,7 +96,7 @@ type Options struct {
 	UpdateAgentMetricsFn func(ctx context.Context, labels prometheusmetrics.AgentMetricLabels, metrics []*agentproto.Stats_Metric)
 }

-func New(opts Options) *API {
+func New(opts Options, workspace database.Workspace) *API {
 	if opts.Clock == nil {
 		opts.Clock = quartz.NewReal()
 	}
@@ -114,6 +118,13 @@ func New(opts Options) *API {
 		WorkspaceID:              opts.WorkspaceID,
 	}

+	// Don't cache details for prebuilds, though the cached fields will eventually be updated
+	// by the refresh routine once the prebuild workspace is claimed.
+	api.cachedWorkspaceFields = &CachedWorkspaceFields{}
+	if !workspace.IsPrebuild() {
+		api.cachedWorkspaceFields.UpdateValues(workspace)
+	}
+
 	api.AnnouncementBannerAPI = &AnnouncementBannerAPI{
 		appearanceFetcher: opts.AppearanceFetcher,
 	}
@@ -139,6 +150,7 @@ func New(opts Options) *API {

 	api.StatsAPI = &StatsAPI{
 		AgentFn:                   api.agent,
+		Workspace:                 api.cachedWorkspaceFields,
 		Database:                  opts.Database,
 		Log:                       opts.Log,
 		StatsReporter:             opts.StatsReporter,
@@ -162,10 +174,11 @@ func New(opts Options) *API {
 	}

 	api.MetadataAPI = &MetadataAPI{
-		AgentFn:  api.agent,
-		Database: opts.Database,
-		Pubsub:   opts.Pubsub,
-		Log:      opts.Log,
+		AgentFn:   api.agent,
+		Workspace: api.cachedWorkspaceFields,
+		Database:  opts.Database,
+		Pubsub:    opts.Pubsub,
+		Log:       opts.Log,
 	}

 	api.LogsAPI = &LogsAPI{
@@ -205,6 +218,10 @@ func New(opts Options) *API {
 		Database:       opts.Database,
 	}

+	// Start background cache refresh loop to handle workspace changes
+	// like prebuild claims where owner_id and other fields may be modified in the DB.
+	go api.startCacheRefreshLoop(opts.AuthenticatedCtx)
+
 	return api
 }

@@ -254,6 +271,56 @@ func (a *API) agent(ctx context.Context) (database.WorkspaceAgent, error) {
 	return agent, nil
 }

+// refreshCachedWorkspace periodically updates the cached workspace fields.
+// This ensures that changes like prebuild claims (which modify owner_id, name, etc.)
+// are eventually reflected in the cache without requiring agent reconnection.
+func (a *API) refreshCachedWorkspace(ctx context.Context) {
+	ws, err := a.opts.Database.GetWorkspaceByID(ctx, a.opts.WorkspaceID)
+	if err != nil {
+		a.opts.Log.Warn(ctx, "failed to refresh cached workspace fields", slog.Error(err))
+		a.cachedWorkspaceFields.Clear()
+		return
+	}
+
+	if ws.IsPrebuild() {
+		return
+	}
+
+	// If we still have the same values, skip the update and logging calls.
+	if a.cachedWorkspaceFields.identity.Equal(database.WorkspaceIdentityFromWorkspace(ws)) {
+		return
+	}
+	// Update fields that can change during workspace lifecycle (e.g., AutostartSchedule)
+	a.cachedWorkspaceFields.UpdateValues(ws)
+
+	a.opts.Log.Debug(ctx, "refreshed cached workspace fields",
+		slog.F("workspace_id", ws.ID),
+		slog.F("owner_id", ws.OwnerID),
+		slog.F("name", ws.Name))
+}
+
+// startCacheRefreshLoop runs a background goroutine that periodically refreshes
+// the cached workspace fields. This is primarily needed to handle prebuild claims
+// where the owner_id and other fields change while the agent connection persists.
+func (a *API) startCacheRefreshLoop(ctx context.Context) {
+	// Refresh every 5 minutes. This provides a reasonable balance between:
+	// - Keeping cache fresh for prebuild claims and other workspace updates
+	// - Minimizing unnecessary database queries
+	ticker := a.opts.Clock.TickerFunc(ctx, workspaceCacheRefreshInterval, func() error {
+		a.refreshCachedWorkspace(ctx)
+		return nil
+	}, "cache_refresh")
+
+	// We need to wait on the ticker exiting.
+	_ = ticker.Wait()
+
+	a.opts.Log.Debug(ctx, "cache refresh loop exited, invalidating the workspace cache on agent API",
+		slog.F("workspace_id", a.cachedWorkspaceFields.identity.ID),
+		slog.F("owner_id", a.cachedWorkspaceFields.identity.OwnerUsername),
+		slog.F("name", a.cachedWorkspaceFields.identity.Name))
+	a.cachedWorkspaceFields.Clear()
+}
+
 func (a *API) publishWorkspaceUpdate(ctx context.Context, agent *database.WorkspaceAgent, kind wspubsub.WorkspaceEventKind) error {
 	a.opts.PublishWorkspaceUpdateFn(ctx, a.opts.OwnerID, wspubsub.WorkspaceEvent{
 		Kind:        kind,
@@ -0,0 +1,52 @@
+package agentapi
+
+import (
+	"sync"
+
+	"github.com/coder/coder/v2/coderd/database"
+)
+
+// CachedWorkspaceFields contains workspace data that is safe to cache for the
+// duration of an agent connection. These fields are used to reduce database calls
+// in high-frequency operations like stats reporting and metadata updates.
+// Prebuild workspaces should not be cached using this struct within the API struct,
+// however some of these fields for a workspace can be updated live so there is a
+// routine in the API for refreshing the workspace on a timed interval.
+//
+// IMPORTANT: ACL fields (GroupACL, UserACL) are NOT cached because they can be
+// modified in the database and we must use fresh data for authorization checks.
+type CachedWorkspaceFields struct {
+	lock sync.RWMutex
+
+	identity database.WorkspaceIdentity
+}
+
+func (cws *CachedWorkspaceFields) Clear() {
+	cws.lock.Lock()
+	defer cws.lock.Unlock()
+	cws.identity = database.WorkspaceIdentity{}
+}
+
+func (cws *CachedWorkspaceFields) UpdateValues(ws database.Workspace) {
+	cws.lock.Lock()
+	defer cws.lock.Unlock()
+	cws.identity.ID = ws.ID
+	cws.identity.OwnerID = ws.OwnerID
+	cws.identity.OrganizationID = ws.OrganizationID
+	cws.identity.TemplateID = ws.TemplateID
+	cws.identity.Name = ws.Name
+	cws.identity.OwnerUsername = ws.OwnerUsername
+	cws.identity.TemplateName = ws.TemplateName
+	cws.identity.AutostartSchedule = ws.AutostartSchedule
+}
+
+// Returns the Workspace, true, unless the workspace has not been cached (nuked or was a prebuild).
+func (cws *CachedWorkspaceFields) AsWorkspaceIdentity() (database.WorkspaceIdentity, bool) {
+	cws.lock.RLock()
+	defer cws.lock.RUnlock()
+	// Should we be more explicit about all fields being set to be valid?
+	if cws.identity.Equal(database.WorkspaceIdentity{}) {
+		return database.WorkspaceIdentity{}, false
+	}
+	return cws.identity, true
+}
@@ -0,0 +1,97 @@
+package agentapi_test
+
+import (
+	"testing"
+
+	"github.com/google/uuid"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/coderd/agentapi"
+	"github.com/coder/coder/v2/coderd/database"
+)
+
+func TestCacheClear(t *testing.T) {
+	t.Parallel()
+
+	var (
+		user = database.User{
+			ID:       uuid.New(),
+			Username: "bill",
+		}
+		template = database.Template{
+			ID:   uuid.New(),
+			Name: "tpl",
+		}
+		workspace = database.Workspace{
+			ID:            uuid.New(),
+			OwnerID:       user.ID,
+			OwnerUsername: user.Username,
+			TemplateID:    template.ID,
+			Name:          "xyz",
+			TemplateName:  template.Name,
+		}
+		workspaceAsCacheFields = agentapi.CachedWorkspaceFields{}
+	)
+
+	workspaceAsCacheFields.UpdateValues(database.Workspace{
+		ID:                workspace.ID,
+		OwnerID:           workspace.OwnerID,
+		OwnerUsername:     workspace.OwnerUsername,
+		TemplateID:        workspace.TemplateID,
+		Name:              workspace.Name,
+		TemplateName:      workspace.TemplateName,
+		AutostartSchedule: workspace.AutostartSchedule,
+	},
+	)
+
+	emptyCws := agentapi.CachedWorkspaceFields{}
+	workspaceAsCacheFields.Clear()
+	wsi, ok := workspaceAsCacheFields.AsWorkspaceIdentity()
+	require.False(t, ok)
+	ecwsi, ok := emptyCws.AsWorkspaceIdentity()
+	require.False(t, ok)
+	require.True(t, ecwsi.Equal(wsi))
+}
+
+func TestCacheUpdate(t *testing.T) {
+	t.Parallel()
+
+	var (
+		user = database.User{
+			ID:       uuid.New(),
+			Username: "bill",
+		}
+		template = database.Template{
+			ID:   uuid.New(),
+			Name: "tpl",
+		}
+		workspace = database.Workspace{
+			ID:            uuid.New(),
+			OwnerID:       user.ID,
+			OwnerUsername: user.Username,
+			TemplateID:    template.ID,
+			Name:          "xyz",
+			TemplateName:  template.Name,
+		}
+		workspaceAsCacheFields = agentapi.CachedWorkspaceFields{}
+	)
+
+	workspaceAsCacheFields.UpdateValues(database.Workspace{
+		ID:                workspace.ID,
+		OwnerID:           workspace.OwnerID,
+		OwnerUsername:     workspace.OwnerUsername,
+		TemplateID:        workspace.TemplateID,
+		Name:              workspace.Name,
+		TemplateName:      workspace.TemplateName,
+		AutostartSchedule: workspace.AutostartSchedule,
+	},
+	)
+
+	cws := agentapi.CachedWorkspaceFields{}
+	cws.UpdateValues(workspace)
+	wsi, ok := workspaceAsCacheFields.AsWorkspaceIdentity()
+	require.True(t, ok)
+	cwsi, ok := cws.AsWorkspaceIdentity()
+	require.True(t, ok)
+	require.True(t, wsi.Equal(cwsi))
+}
@@ -12,15 +12,17 @@ import (
 	"cdr.dev/slog"
 	agentproto "github.com/coder/coder/v2/agent/proto"
 	"github.com/coder/coder/v2/coderd/database"
+	"github.com/coder/coder/v2/coderd/database/dbauthz"
 	"github.com/coder/coder/v2/coderd/database/dbtime"
 	"github.com/coder/coder/v2/coderd/database/pubsub"
 )

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

 	TimeNowFn func() time.Time // defaults to dbtime.Now()
 }
@@ -107,7 +109,19 @@ func (a *MetadataAPI) BatchUpdateMetadata(ctx context.Context, req *agentproto.B
 		)
 	}

-	err = a.Database.UpdateWorkspaceAgentMetadata(ctx, dbUpdate)
+	// Inject RBAC object into context for dbauthz fast path, avoid having to
+	// call GetWorkspaceByAgentID on every metadata update.
+	rbacCtx := ctx
+	if dbws, ok := a.Workspace.AsWorkspaceIdentity(); ok {
+		rbacCtx, err = dbauthz.WithWorkspaceRBAC(ctx, dbws.RBACObject())
+		if err != nil {
+			// Don't error level log here, will exit the function. We want to fall back to GetWorkspaceByAgentID.
+			//nolint:gocritic
+			a.Log.Debug(ctx, "Cached workspace was present but RBAC object was invalid", slog.F("err", err))
+		}
+	}
+
+	err = a.Database.UpdateWorkspaceAgentMetadata(rbacCtx, dbUpdate)
 	if err != nil {
 		return nil, xerrors.Errorf("update workspace agent metadata in database: %w", err)
 	}
@@ -2,12 +2,14 @@ package agentapi_test

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

 	"github.com/google/uuid"
+	"github.com/prometheus/client_golang/prometheus"
 	"github.com/stretchr/testify/require"
 	"go.uber.org/mock/gomock"
 	"google.golang.org/protobuf/types/known/timestamppb"
@@ -15,10 +17,14 @@ import (
 	agentproto "github.com/coder/coder/v2/agent/proto"
 	"github.com/coder/coder/v2/coderd/agentapi"
 	"github.com/coder/coder/v2/coderd/database"
+	"github.com/coder/coder/v2/coderd/database/dbauthz"
 	"github.com/coder/coder/v2/coderd/database/dbmock"
 	"github.com/coder/coder/v2/coderd/database/dbtime"
 	"github.com/coder/coder/v2/coderd/database/pubsub"
+	"github.com/coder/coder/v2/coderd/rbac"
+	"github.com/coder/coder/v2/coderd/rbac/policy"
 	"github.com/coder/coder/v2/testutil"
+	"github.com/coder/quartz"
 )

 type fakePublisher struct {
@@ -84,9 +90,10 @@ func TestBatchUpdateMetadata(t *testing.T) {
 			AgentFn: func(context.Context) (database.WorkspaceAgent, error) {
 				return agent, nil
 			},
-			Database: dbM,
-			Pubsub:   pub,
-			Log:      testutil.Logger(t),
+			Workspace: &agentapi.CachedWorkspaceFields{},
+			Database:  dbM,
+			Pubsub:    pub,
+			Log:       testutil.Logger(t),
 			TimeNowFn: func() time.Time {
 				return now
 			},
@@ -169,9 +176,10 @@ func TestBatchUpdateMetadata(t *testing.T) {
 			AgentFn: func(context.Context) (database.WorkspaceAgent, error) {
 				return agent, nil
 			},
-			Database: dbM,
-			Pubsub:   pub,
-			Log:      testutil.Logger(t),
+			Workspace: &agentapi.CachedWorkspaceFields{},
+			Database:  dbM,
+			Pubsub:    pub,
+			Log:       testutil.Logger(t),
 			TimeNowFn: func() time.Time {
 				return now
 			},
@@ -238,9 +246,10 @@ func TestBatchUpdateMetadata(t *testing.T) {
 			AgentFn: func(context.Context) (database.WorkspaceAgent, error) {
 				return agent, nil
 			},
-			Database: dbM,
-			Pubsub:   pub,
-			Log:      testutil.Logger(t),
+			Workspace: &agentapi.CachedWorkspaceFields{},
+			Database:  dbM,
+			Pubsub:    pub,
+			Log:       testutil.Logger(t),
 			TimeNowFn: func() time.Time {
 				return now
 			},
@@ -272,4 +281,421 @@ func TestBatchUpdateMetadata(t *testing.T) {
 			Keys: []string{req.Metadata[0].Key, req.Metadata[1].Key, req.Metadata[2].Key},
 		}, gotEvent)
 	})
+
+	// Test RBAC fast path with valid RBAC object - should NOT call GetWorkspaceByAgentID
+	// This test verifies that when a valid RBAC object is present in context, the dbauthz layer
+	// uses the fast path and skips the GetWorkspaceByAgentID database call.
+	t.Run("WorkspaceCached_SkipsDBCall", func(t *testing.T) {
+		t.Parallel()
+
+		var (
+			ctrl = gomock.NewController(t)
+			dbM  = dbmock.NewMockStore(ctrl)
+			pub  = &fakePublisher{}
+			now  = dbtime.Now()
+			// Set up consistent IDs that represent a valid workspace->agent relationship
+			workspaceID = uuid.MustParse("12345678-1234-1234-1234-123456789012")
+			ownerID     = uuid.MustParse("87654321-4321-4321-4321-210987654321")
+			orgID       = uuid.MustParse("11111111-1111-1111-1111-111111111111")
+			agentID     = uuid.MustParse("aaaaaaaa-aaaa-aaaa-aaaa-aaaaaaaaaaaa")
+		)
+
+		agent := database.WorkspaceAgent{
+			ID: agentID,
+			// In a real scenario, this agent would belong to a resource in the workspace above
+		}
+
+		req := &agentproto.BatchUpdateMetadataRequest{
+			Metadata: []*agentproto.Metadata{
+				{
+					Key: "test_key",
+					Result: &agentproto.WorkspaceAgentMetadata_Result{
+						CollectedAt: timestamppb.New(now.Add(-time.Second)),
+						Age:         1,
+						Value:       "test_value",
+					},
+				},
+			},
+		}
+
+		// Expect UpdateWorkspaceAgentMetadata to be called
+		dbM.EXPECT().UpdateWorkspaceAgentMetadata(gomock.Any(), database.UpdateWorkspaceAgentMetadataParams{
+			WorkspaceAgentID: agent.ID,
+			Key:              []string{"test_key"},
+			Value:            []string{"test_value"},
+			Error:            []string{""},
+			CollectedAt:      []time.Time{now},
+		}).Return(nil)
+
+		// DO NOT expect GetWorkspaceByAgentID - the fast path should skip this call
+		// If GetWorkspaceByAgentID is called, the test will fail with "unexpected call"
+
+		// dbauthz will call Wrappers() to check for wrapped databases
+		dbM.EXPECT().Wrappers().Return([]string{}).AnyTimes()
+
+		// Set up dbauthz to test the actual authorization layer
+		auth := rbac.NewStrictCachingAuthorizer(prometheus.NewRegistry())
+		accessControlStore := &atomic.Pointer[dbauthz.AccessControlStore]{}
+		var acs dbauthz.AccessControlStore = dbauthz.AGPLTemplateAccessControlStore{}
+		accessControlStore.Store(&acs)
+
+		api := &agentapi.MetadataAPI{
+			AgentFn: func(_ context.Context) (database.WorkspaceAgent, error) {
+				return agent, nil
+			},
+			Workspace: &agentapi.CachedWorkspaceFields{},
+			Database:  dbauthz.New(dbM, auth, testutil.Logger(t), accessControlStore),
+			Pubsub:    pub,
+			Log:       testutil.Logger(t),
+			TimeNowFn: func() time.Time {
+				return now
+			},
+		}
+
+		api.Workspace.UpdateValues(database.Workspace{
+			ID:             workspaceID,
+			OwnerID:        ownerID,
+			OrganizationID: orgID,
+		})
+
+		// Create context with system actor so authorization passes
+		ctx := dbauthz.AsSystemRestricted(context.Background())
+		resp, err := api.BatchUpdateMetadata(ctx, req)
+		require.NoError(t, err)
+		require.NotNil(t, resp)
+	})
+	// Test RBAC slow path - invalid RBAC object should fall back to GetWorkspaceByAgentID
+	// This test verifies that when the RBAC object has invalid IDs (nil UUIDs), the dbauthz layer
+	// falls back to the slow path and calls GetWorkspaceByAgentID.
+	t.Run("InvalidWorkspaceCached_RequiresDBCall", func(t *testing.T) {
+		t.Parallel()
+
+		var (
+			ctrl        = gomock.NewController(t)
+			dbM         = dbmock.NewMockStore(ctrl)
+			pub         = &fakePublisher{}
+			now         = dbtime.Now()
+			workspaceID = uuid.MustParse("12345678-1234-1234-1234-123456789012")
+			ownerID     = uuid.MustParse("87654321-4321-4321-4321-210987654321")
+			orgID       = uuid.MustParse("11111111-1111-1111-1111-111111111111")
+			agentID     = uuid.MustParse("bbbbbbbb-bbbb-bbbb-bbbb-bbbbbbbbbbbb")
+		)
+
+		agent := database.WorkspaceAgent{
+			ID: agentID,
+		}
+
+		req := &agentproto.BatchUpdateMetadataRequest{
+			Metadata: []*agentproto.Metadata{
+				{
+					Key: "test_key",
+					Result: &agentproto.WorkspaceAgentMetadata_Result{
+						CollectedAt: timestamppb.New(now.Add(-time.Second)),
+						Age:         1,
+						Value:       "test_value",
+					},
+				},
+			},
+		}
+
+		// EXPECT GetWorkspaceByAgentID to be called because the RBAC fast path validation fails
+		dbM.EXPECT().GetWorkspaceByAgentID(gomock.Any(), agentID).Return(database.Workspace{
+			ID:             workspaceID,
+			OwnerID:        ownerID,
+			OrganizationID: orgID,
+		}, nil)
+
+		// Expect UpdateWorkspaceAgentMetadata to be called after authorization
+		dbM.EXPECT().UpdateWorkspaceAgentMetadata(gomock.Any(), database.UpdateWorkspaceAgentMetadataParams{
+			WorkspaceAgentID: agent.ID,
+			Key:              []string{"test_key"},
+			Value:            []string{"test_value"},
+			Error:            []string{""},
+			CollectedAt:      []time.Time{now},
+		}).Return(nil)
+
+		// dbauthz will call Wrappers() to check for wrapped databases
+		dbM.EXPECT().Wrappers().Return([]string{}).AnyTimes()
+
+		// Set up dbauthz to test the actual authorization layer
+		auth := rbac.NewStrictCachingAuthorizer(prometheus.NewRegistry())
+		accessControlStore := &atomic.Pointer[dbauthz.AccessControlStore]{}
+		var acs dbauthz.AccessControlStore = dbauthz.AGPLTemplateAccessControlStore{}
+		accessControlStore.Store(&acs)
+
+		api := &agentapi.MetadataAPI{
+			AgentFn: func(_ context.Context) (database.WorkspaceAgent, error) {
+				return agent, nil
+			},
+
+			Workspace: &agentapi.CachedWorkspaceFields{},
+			Database:  dbauthz.New(dbM, auth, testutil.Logger(t), accessControlStore),
+			Pubsub:    pub,
+			Log:       testutil.Logger(t),
+			TimeNowFn: func() time.Time {
+				return now
+			},
+		}
+
+		// Create an invalid RBAC object with nil UUIDs for owner/org
+		// This will fail dbauthz fast path validation and trigger GetWorkspaceByAgentID
+		api.Workspace.UpdateValues(database.Workspace{
+			ID:             uuid.MustParse("cccccccc-cccc-cccc-cccc-cccccccccccc"),
+			OwnerID:        uuid.Nil, // Invalid: fails dbauthz fast path validation
+			OrganizationID: uuid.Nil, // Invalid: fails dbauthz fast path validation
+		})
+
+		// Create context with system actor so authorization passes
+		ctx := dbauthz.AsSystemRestricted(context.Background())
+		resp, err := api.BatchUpdateMetadata(ctx, req)
+		require.NoError(t, err)
+		require.NotNil(t, resp)
+	})
+	// Test RBAC slow path - no RBAC object in context
+	// This test verifies that when no RBAC object is present in context, the dbauthz layer
+	// falls back to the slow path and calls GetWorkspaceByAgentID.
+	t.Run("WorkspaceNotCached_RequiresDBCall", func(t *testing.T) {
+		t.Parallel()
+
+		var (
+			ctrl        = gomock.NewController(t)
+			dbM         = dbmock.NewMockStore(ctrl)
+			pub         = &fakePublisher{}
+			now         = dbtime.Now()
+			workspaceID = uuid.MustParse("12345678-1234-1234-1234-123456789012")
+			ownerID     = uuid.MustParse("87654321-4321-4321-4321-210987654321")
+			orgID       = uuid.MustParse("11111111-1111-1111-1111-111111111111")
+			agentID     = uuid.MustParse("dddddddd-dddd-dddd-dddd-dddddddddddd")
+		)
+
+		agent := database.WorkspaceAgent{
+			ID: agentID,
+		}
+
+		req := &agentproto.BatchUpdateMetadataRequest{
+			Metadata: []*agentproto.Metadata{
+				{
+					Key: "test_key",
+					Result: &agentproto.WorkspaceAgentMetadata_Result{
+						CollectedAt: timestamppb.New(now.Add(-time.Second)),
+						Age:         1,
+						Value:       "test_value",
+					},
+				},
+			},
+		}
+
+		// EXPECT GetWorkspaceByAgentID to be called because no RBAC object is in context
+		dbM.EXPECT().GetWorkspaceByAgentID(gomock.Any(), agentID).Return(database.Workspace{
+			ID:             workspaceID,
+			OwnerID:        ownerID,
+			OrganizationID: orgID,
+		}, nil)
+
+		// Expect UpdateWorkspaceAgentMetadata to be called after authorization
+		dbM.EXPECT().UpdateWorkspaceAgentMetadata(gomock.Any(), database.UpdateWorkspaceAgentMetadataParams{
+			WorkspaceAgentID: agent.ID,
+			Key:              []string{"test_key"},
+			Value:            []string{"test_value"},
+			Error:            []string{""},
+			CollectedAt:      []time.Time{now},
+		}).Return(nil)
+
+		// dbauthz will call Wrappers() to check for wrapped databases
+		dbM.EXPECT().Wrappers().Return([]string{}).AnyTimes()
+
+		// Set up dbauthz to test the actual authorization layer
+		auth := rbac.NewStrictCachingAuthorizer(prometheus.NewRegistry())
+		accessControlStore := &atomic.Pointer[dbauthz.AccessControlStore]{}
+		var acs dbauthz.AccessControlStore = dbauthz.AGPLTemplateAccessControlStore{}
+		accessControlStore.Store(&acs)
+
+		api := &agentapi.MetadataAPI{
+			AgentFn: func(_ context.Context) (database.WorkspaceAgent, error) {
+				return agent, nil
+			},
+			Workspace: &agentapi.CachedWorkspaceFields{},
+			Database:  dbauthz.New(dbM, auth, testutil.Logger(t), accessControlStore),
+			Pubsub:    pub,
+			Log:       testutil.Logger(t),
+			TimeNowFn: func() time.Time {
+				return now
+			},
+		}
+
+		// Create context with system actor so authorization passes
+		ctx := dbauthz.AsSystemRestricted(context.Background())
+		resp, err := api.BatchUpdateMetadata(ctx, req)
+		require.NoError(t, err)
+		require.NotNil(t, resp)
+	})
+
+	// Test cache refresh - AutostartSchedule updated
+	// This test verifies that the cache refresh mechanism actually calls GetWorkspaceByID
+	// and updates the cached workspace fields when the workspace is modified (e.g., autostart schedule changes).
+	t.Run("CacheRefreshed_AutostartScheduleUpdated", func(t *testing.T) {
+		t.Parallel()
+
+		var (
+			ctrl       = gomock.NewController(t)
+			dbM        = dbmock.NewMockStore(ctrl)
+			pub        = &fakePublisher{}
+			now        = dbtime.Now()
+			mClock     = quartz.NewMock(t)
+			tickerTrap = mClock.Trap().TickerFunc("cache_refresh")
+
+			workspaceID = uuid.MustParse("12345678-1234-1234-1234-123456789012")
+			ownerID     = uuid.MustParse("87654321-4321-4321-4321-210987654321")
+			orgID       = uuid.MustParse("11111111-1111-1111-1111-111111111111")
+			templateID  = uuid.MustParse("aaaabbbb-cccc-dddd-eeee-ffffffff0000")
+			agentID     = uuid.MustParse("ffffffff-ffff-ffff-ffff-ffffffffffff")
+		)
+
+		agent := database.WorkspaceAgent{
+			ID: agentID,
+		}
+
+		// Initial workspace - has Monday-Friday 9am autostart
+		initialWorkspace := database.Workspace{
+			ID:                workspaceID,
+			OwnerID:           ownerID,
+			OrganizationID:    orgID,
+			TemplateID:        templateID,
+			Name:              "my-workspace",
+			OwnerUsername:     "testuser",
+			TemplateName:      "test-template",
+			AutostartSchedule: sql.NullString{Valid: true, String: "CRON_TZ=UTC 0 9 * * 1-5"},
+		}
+
+		// Updated workspace - user changed autostart to 5pm and renamed workspace
+		updatedWorkspace := database.Workspace{
+			ID:                workspaceID,
+			OwnerID:           ownerID,
+			OrganizationID:    orgID,
+			TemplateID:        templateID,
+			Name:              "my-workspace-renamed", // Changed!
+			OwnerUsername:     "testuser",
+			TemplateName:      "test-template",
+			AutostartSchedule: sql.NullString{Valid: true, String: "CRON_TZ=UTC 0 17 * * 1-5"}, // Changed!
+			DormantAt:         sql.NullTime{},
+		}
+
+		req := &agentproto.BatchUpdateMetadataRequest{
+			Metadata: []*agentproto.Metadata{
+				{
+					Key: "test_key",
+					Result: &agentproto.WorkspaceAgentMetadata_Result{
+						CollectedAt: timestamppb.New(now.Add(-time.Second)),
+						Age:         1,
+						Value:       "test_value",
+					},
+				},
+			},
+		}
+
+		// EXPECT GetWorkspaceByID to be called during cache refresh
+		// This is the key assertion - proves the refresh mechanism is working
+		dbM.EXPECT().GetWorkspaceByID(gomock.Any(), workspaceID).Return(updatedWorkspace, nil)
+
+		// API needs to fetch the agent when calling metadata update
+		dbM.EXPECT().GetWorkspaceAgentByID(gomock.Any(), agentID).Return(agent, nil)
+
+		// After refresh, metadata update should work with updated cache
+		dbM.EXPECT().UpdateWorkspaceAgentMetadata(gomock.Any(), gomock.Any()).DoAndReturn(
+			func(ctx context.Context, params database.UpdateWorkspaceAgentMetadataParams) error {
+				require.Equal(t, agent.ID, params.WorkspaceAgentID)
+				require.Equal(t, []string{"test_key"}, params.Key)
+				require.Equal(t, []string{"test_value"}, params.Value)
+				require.Equal(t, []string{""}, params.Error)
+				require.Len(t, params.CollectedAt, 1)
+				return nil
+			},
+		).AnyTimes()
+
+		// May call GetWorkspaceByAgentID if slow path is used before refresh
+		dbM.EXPECT().GetWorkspaceByAgentID(gomock.Any(), agentID).Return(updatedWorkspace, nil).AnyTimes()
+
+		// dbauthz will call Wrappers()
+		dbM.EXPECT().Wrappers().Return([]string{}).AnyTimes()
+
+		// Set up dbauthz
+		auth := rbac.NewStrictCachingAuthorizer(prometheus.NewRegistry())
+		accessControlStore := &atomic.Pointer[dbauthz.AccessControlStore]{}
+		var acs dbauthz.AccessControlStore = dbauthz.AGPLTemplateAccessControlStore{}
+		accessControlStore.Store(&acs)
+
+		ctx, cancel := context.WithCancel(context.Background())
+		defer cancel()
+
+		// Create roles with workspace permissions
+		userRoles := rbac.Roles([]rbac.Role{
+			{
+				Identifier: rbac.RoleMember(),
+				User: []rbac.Permission{
+					{
+						Negate:       false,
+						ResourceType: rbac.ResourceWorkspace.Type,
+						Action:       policy.WildcardSymbol,
+					},
+				},
+				ByOrgID: map[string]rbac.OrgPermissions{
+					orgID.String(): {
+						Member: []rbac.Permission{
+							{
+								Negate:       false,
+								ResourceType: rbac.ResourceWorkspace.Type,
+								Action:       policy.WildcardSymbol,
+							},
+						},
+					},
+				},
+			},
+		})
+
+		agentScope := rbac.WorkspaceAgentScope(rbac.WorkspaceAgentScopeParams{
+			WorkspaceID: workspaceID,
+			OwnerID:     ownerID,
+			TemplateID:  templateID,
+			VersionID:   uuid.New(),
+		})
+
+		ctxWithActor := dbauthz.As(ctx, rbac.Subject{
+			Type:         rbac.SubjectTypeUser,
+			FriendlyName: "testuser",
+			Email:        "testuser@example.com",
+			ID:           ownerID.String(),
+			Roles:        userRoles,
+			Groups:       []string{orgID.String()},
+			Scope:        agentScope,
+		}.WithCachedASTValue())
+
+		// Create full API with cached workspace fields (initial state)
+		api := agentapi.New(agentapi.Options{
+			AuthenticatedCtx: ctxWithActor,
+			AgentID:          agentID,
+			WorkspaceID:      workspaceID,
+			OwnerID:          ownerID,
+			OrganizationID:   orgID,
+			Database:         dbauthz.New(dbM, auth, testutil.Logger(t), accessControlStore),
+			Log:              testutil.Logger(t),
+			Clock:            mClock,
+			Pubsub:           pub,
+		}, initialWorkspace) // Cache is initialized with 9am schedule and "my-workspace" name
+
+		// Wait for ticker to be set up and release it so it can fire
+		tickerTrap.MustWait(ctx).MustRelease(ctx)
+		tickerTrap.Close()
+
+		// Advance clock to trigger cache refresh and wait for it to complete
+		_, aw := mClock.AdvanceNext()
+		aw.MustWait(ctx)
+
+		// At this point, GetWorkspaceByID should have been called and cache updated
+		// The cache now has the 5pm schedule and "my-workspace-renamed" name
+
+		// Now call metadata update to verify the refreshed cache works
+		resp, err := api.MetadataAPI.BatchUpdateMetadata(ctxWithActor, req)
+		require.NoError(t, err)
+		require.NotNil(t, resp)
+	})
 }
--- a/Show More
+++ b/Show More