feat: add POC for aibridge HTTP proxy

feat: add retention config for workspace_agent_logs (#21039 )
Replace hardcoded 7-day retention for workspace agent logs with configurable retention from deployment settings. Defaults to 7d to preserve existing behavior. Depends on #21038 Updates #20743
2025-12-02 20:18:02 +00:00 · 2025-12-02 16:01:33 +00:00 · 2025-12-02 15:47:36 +00:00 · 2025-12-02 15:41:38 +00:00 · 2025-12-02 16:18:07 +01:00 · 2025-12-02 16:50:09 +02:00
809 changed files with 41411 additions and 17994 deletions
@@ -0,0 +1,126 @@
+# Coder Architecture
+
+This document provides an overview of Coder's architecture and core systems.
+
+## What is Coder?
+
+Coder is a platform for creating, managing, and using remote development environments (also known as Cloud Development Environments or CDEs). It leverages Terraform to define and provision these environments, which are referred to as "workspaces" within the project. The system is designed to be extensible, secure, and provide developers with a seamless remote development experience.
+
+## Core Architecture
+
+The heart of Coder is a control plane that orchestrates the creation and management of workspaces. This control plane interacts with separate Provisioner processes over gRPC to handle workspace builds. The Provisioners consume workspace definitions and use Terraform to create the actual infrastructure.
+
+The CLI package serves dual purposes - it can be used to launch the control plane itself and also provides client functionality for users to interact with an existing control plane instance. All user-facing frontend code is developed in TypeScript using React and lives in the `site/` directory.
+
+The database layer uses PostgreSQL with SQLC for generating type-safe database code. Database migrations are carefully managed to ensure both forward and backward compatibility through paired `.up.sql` and `.down.sql` files.
+
+## API Design
+
+Coder's API architecture combines REST and gRPC approaches. The REST API is defined in `coderd/coderd.go` and uses Chi for HTTP routing. This provides the primary interface for the frontend and external integrations.
+
+Internal communication with Provisioners occurs over gRPC, with service definitions maintained in `.proto` files. This separation allows for efficient binary communication with the components responsible for infrastructure management while providing a standard REST interface for human-facing applications.
+
+## Network Architecture
+
+Coder implements a secure networking layer based on Tailscale's Wireguard implementation. The `tailnet` package provides connectivity between workspace agents and clients through DERP (Designated Encrypted Relay for Packets) servers when direct connections aren't possible. This creates a secure overlay network allowing access to workspaces regardless of network topology, firewalls, or NAT configurations.
+
+### Tailnet and DERP System
+
+The networking system has three key components:
+
+1. **Tailnet**: An overlay network implemented in the `tailnet` package that provides secure, end-to-end encrypted connections between clients, the Coder server, and workspace agents.
+
+2. **DERP Servers**: These relay traffic when direct connections aren't possible. Coder provides several options:
+   - A built-in DERP server that runs on the Coder control plane
+   - Integration with Tailscale's global DERP infrastructure
+   - Support for custom DERP servers for lower latency or offline deployments
+
+3. **Direct Connections**: When possible, the system establishes peer-to-peer connections between clients and workspaces using STUN for NAT traversal. This requires both endpoints to send UDP traffic on ephemeral ports.
+
+### Workspace Proxies
+
+Workspace proxies (in the Enterprise edition) provide regional relay points for browser-based connections, reducing latency for geo-distributed teams. Key characteristics:
+
+- Deployed as independent servers that authenticate with the Coder control plane
+- Relay connections for SSH, workspace apps, port forwarding, and web terminals
+- Do not make direct database connections
+- Managed through the `coder wsproxy` commands
+- Implemented primarily in the `enterprise/wsproxy/` package
+
+## Agent System
+
+The workspace agent runs within each provisioned workspace and provides core functionality including:
+
+- SSH access to workspaces via the `agentssh` package
+- Port forwarding
+- Terminal connectivity via the `pty` package for pseudo-terminal support
+- Application serving
+- Healthcheck monitoring
+- Resource usage reporting
+
+Agents communicate with the control plane using the tailnet system and authenticate using secure tokens.
+
+## Workspace Applications
+
+Workspace applications (or "apps") provide browser-based access to services running within workspaces. The system supports:
+
+- HTTP(S) and WebSocket connections
+- Path-based or subdomain-based access URLs
+- Health checks to monitor application availability
+- Different sharing levels (owner-only, authenticated users, or public)
+- Custom icons and display settings
+
+The implementation is primarily in the `coderd/workspaceapps/` directory with components for URL generation, proxying connections, and managing application state.
+
+## Implementation Details
+
+The project structure separates frontend and backend concerns. React components and pages are organized in the `site/src/` directory, with Jest used for testing. The backend is primarily written in Go, with a strong emphasis on error handling patterns and test coverage.
+
+Database interactions are carefully managed through migrations in `coderd/database/migrations/` and queries in `coderd/database/queries/`. All new queries require proper database authorization (dbauthz) implementation to ensure that only users with appropriate permissions can access specific resources.
+
+## Authorization System
+
+The database authorization (dbauthz) system enforces fine-grained access control across all database operations. It uses role-based access control (RBAC) to validate user permissions before executing database operations. The `dbauthz` package wraps the database store and performs authorization checks before returning data. All database operations must pass through this layer to ensure security.
+
+## Testing Framework
+
+The codebase has a comprehensive testing approach with several key components:
+
+1. **Parallel Testing**: All tests must use `t.Parallel()` to run concurrently, which improves test suite performance and helps identify race conditions.
+
+2. **coderdtest Package**: This package in `coderd/coderdtest/` provides utilities for creating test instances of the Coder server, setting up test users and workspaces, and mocking external components.
+
+3. **Integration Tests**: Tests often span multiple components to verify system behavior, such as template creation, workspace provisioning, and agent connectivity.
+
+4. **Enterprise Testing**: Enterprise features have dedicated test utilities in the `coderdenttest` package.
+
+## Open Source and Enterprise Components
+
+The repository contains both open source and enterprise components:
+
+- Enterprise code lives primarily in the `enterprise/` directory
+- Enterprise features focus on governance, scalability (high availability), and advanced deployment options like workspace proxies
+- The boundary between open source and enterprise is managed through a licensing system
+- The same core codebase supports both editions, with enterprise features conditionally enabled
+
+## Development Philosophy
+
+Coder emphasizes clear error handling, with specific patterns required:
+
+- Concise error messages that avoid phrases like "failed to"
+- Wrapping errors with `%w` to maintain error chains
+- Using sentinel errors with the "err" prefix (e.g., `errNotFound`)
+
+All tests should run in parallel using `t.Parallel()` to ensure efficient testing and expose potential race conditions. The codebase is rigorously linted with golangci-lint to maintain consistent code quality.
+
+Git contributions follow a standard format with commit messages structured as `type: <message>`, where type is one of `feat`, `fix`, or `chore`.
+
+## Development Workflow
+
+Development can be initiated using `scripts/develop.sh` to start the application after making changes. Database schema updates should be performed through the migration system using `create_migration.sh <name>` to generate migration files, with each `.up.sql` migration paired with a corresponding `.down.sql` that properly reverts all changes.
+
+If the development database gets into a bad state, it can be completely reset by removing the PostgreSQL data directory with `rm -rf .coderv2/postgres`. This will destroy all data in the development database, requiring you to recreate any test users, templates, or workspaces after restarting the application.
+
+Code generation for the database layer uses `coderd/database/generate.sh`, and developers should refer to `sqlc.yaml` for the appropriate style and patterns to follow when creating new queries or tables.
+
+The focus should always be on maintaining security through proper database authorization, clean error handling, and comprehensive test coverage to ensure the platform remains robust and reliable.
@@ -1,124 +0,0 @@
-# Cursor Rules
-
-This project is called "Coder" - an application for managing remote development environments.
-
-Coder provides a platform for creating, managing, and using remote development environments (also known as Cloud Development Environments or CDEs). It leverages Terraform to define and provision these environments, which are referred to as "workspaces" within the project. The system is designed to be extensible, secure, and provide developers with a seamless remote development experience.
-
-## Core Architecture
-
-The heart of Coder is a control plane that orchestrates the creation and management of workspaces. This control plane interacts with separate Provisioner processes over gRPC to handle workspace builds. The Provisioners consume workspace definitions and use Terraform to create the actual infrastructure.
-
-The CLI package serves dual purposes - it can be used to launch the control plane itself and also provides client functionality for users to interact with an existing control plane instance. All user-facing frontend code is developed in TypeScript using React and lives in the `site/` directory.
-
-The database layer uses PostgreSQL with SQLC for generating type-safe database code. Database migrations are carefully managed to ensure both forward and backward compatibility through paired `.up.sql` and `.down.sql` files.
-
-## API Design
-
-Coder's API architecture combines REST and gRPC approaches. The REST API is defined in `coderd/coderd.go` and uses Chi for HTTP routing. This provides the primary interface for the frontend and external integrations.
-
-Internal communication with Provisioners occurs over gRPC, with service definitions maintained in `.proto` files. This separation allows for efficient binary communication with the components responsible for infrastructure management while providing a standard REST interface for human-facing applications.
-
-## Network Architecture
-
-Coder implements a secure networking layer based on Tailscale's Wireguard implementation. The `tailnet` package provides connectivity between workspace agents and clients through DERP (Designated Encrypted Relay for Packets) servers when direct connections aren't possible. This creates a secure overlay network allowing access to workspaces regardless of network topology, firewalls, or NAT configurations.
-
-### Tailnet and DERP System
-
-The networking system has three key components:
-
-1. **Tailnet**: An overlay network implemented in the `tailnet` package that provides secure, end-to-end encrypted connections between clients, the Coder server, and workspace agents.
-
-2. **DERP Servers**: These relay traffic when direct connections aren't possible. Coder provides several options:
-   - A built-in DERP server that runs on the Coder control plane
-   - Integration with Tailscale's global DERP infrastructure
-   - Support for custom DERP servers for lower latency or offline deployments
-
-3. **Direct Connections**: When possible, the system establishes peer-to-peer connections between clients and workspaces using STUN for NAT traversal. This requires both endpoints to send UDP traffic on ephemeral ports.
-
-### Workspace Proxies
-
-Workspace proxies (in the Enterprise edition) provide regional relay points for browser-based connections, reducing latency for geo-distributed teams. Key characteristics:
-
- Deployed as independent servers that authenticate with the Coder control plane
- Relay connections for SSH, workspace apps, port forwarding, and web terminals
- Do not make direct database connections
- Managed through the `coder wsproxy` commands
- Implemented primarily in the `enterprise/wsproxy/` package
-
-## Agent System
-
-The workspace agent runs within each provisioned workspace and provides core functionality including:
-
- SSH access to workspaces via the `agentssh` package
- Port forwarding
- Terminal connectivity via the `pty` package for pseudo-terminal support
- Application serving
- Healthcheck monitoring
- Resource usage reporting
-
-Agents communicate with the control plane using the tailnet system and authenticate using secure tokens.
-
-## Workspace Applications
-
-Workspace applications (or "apps") provide browser-based access to services running within workspaces. The system supports:
-
- HTTP(S) and WebSocket connections
- Path-based or subdomain-based access URLs
- Health checks to monitor application availability
- Different sharing levels (owner-only, authenticated users, or public)
- Custom icons and display settings
-
-The implementation is primarily in the `coderd/workspaceapps/` directory with components for URL generation, proxying connections, and managing application state.
-
-## Implementation Details
-
-The project structure separates frontend and backend concerns. React components and pages are organized in the `site/src/` directory, with Jest used for testing. The backend is primarily written in Go, with a strong emphasis on error handling patterns and test coverage.
-
-Database interactions are carefully managed through migrations in `coderd/database/migrations/` and queries in `coderd/database/queries/`. All new queries require proper database authorization (dbauthz) implementation to ensure that only users with appropriate permissions can access specific resources.
-
-## Authorization System
-
-The database authorization (dbauthz) system enforces fine-grained access control across all database operations. It uses role-based access control (RBAC) to validate user permissions before executing database operations. The `dbauthz` package wraps the database store and performs authorization checks before returning data. All database operations must pass through this layer to ensure security.
-
-## Testing Framework
-
-The codebase has a comprehensive testing approach with several key components:
-
-1. **Parallel Testing**: All tests must use `t.Parallel()` to run concurrently, which improves test suite performance and helps identify race conditions.
-
-2. **coderdtest Package**: This package in `coderd/coderdtest/` provides utilities for creating test instances of the Coder server, setting up test users and workspaces, and mocking external components.
-
-3. **Integration Tests**: Tests often span multiple components to verify system behavior, such as template creation, workspace provisioning, and agent connectivity.
-
-4. **Enterprise Testing**: Enterprise features have dedicated test utilities in the `coderdenttest` package.
-
-## Open Source and Enterprise Components
-
-The repository contains both open source and enterprise components:
-
- Enterprise code lives primarily in the `enterprise/` directory
- Enterprise features focus on governance, scalability (high availability), and advanced deployment options like workspace proxies
- The boundary between open source and enterprise is managed through a licensing system
- The same core codebase supports both editions, with enterprise features conditionally enabled
-
-## Development Philosophy
-
-Coder emphasizes clear error handling, with specific patterns required:
-
- Concise error messages that avoid phrases like "failed to"
- Wrapping errors with `%w` to maintain error chains
- Using sentinel errors with the "err" prefix (e.g., `errNotFound`)
-
-All tests should run in parallel using `t.Parallel()` to ensure efficient testing and expose potential race conditions. The codebase is rigorously linted with golangci-lint to maintain consistent code quality.
-
-Git contributions follow a standard format with commit messages structured as `type: <message>`, where type is one of `feat`, `fix`, or `chore`.
-
-## Development Workflow
-
-Development can be initiated using `scripts/develop.sh` to start the application after making changes. Database schema updates should be performed through the migration system using `create_migration.sh <name>` to generate migration files, with each `.up.sql` migration paired with a corresponding `.down.sql` that properly reverts all changes.
-
-If the development database gets into a bad state, it can be completely reset by removing the PostgreSQL data directory with `rm -rf .coderv2/postgres`. This will destroy all data in the development database, requiring you to recreate any test users, templates, or workspaces after restarting the application.
-
-Code generation for the database layer uses `coderd/database/generate.sh`, and developers should refer to `sqlc.yaml` for the appropriate style and patterns to follow when creating new queries or tables.
-
-The focus should always be on maintaining security through proper database authorization, clean error handling, and comprehensive test coverage to ensure the platform remains robust and reliable.
@@ -0,0 +1 @@
+AGENTS.md
@@ -27,5 +27,7 @@ ignorePatterns:
  - pattern: "splunk.com"
  - pattern: "stackoverflow.com/questions"
  - pattern: "developer.hashicorp.com/terraform/language"
+  - pattern: "platform.openai.com"
+  - pattern: "api.openai.com"
 aliveStatusCodes:
  - 200
@@ -4,7 +4,7 @@ description: |
 inputs:
  version:
    description: "The Go version to use."
-    default: "1.24.6"
+    default: "1.24.10"
  use-preinstalled-go:
    description: "Whether to use preinstalled Go."
    default: "false"
@@ -5,6 +5,13 @@ runs:
  using: "composite"
  steps:
    - name: Setup sqlc
-      uses: sqlc-dev/setup-sqlc@c0209b9199cd1cce6a14fc27cabcec491b651761 # v4.0.0
-      with:
-        sqlc-version: "1.27.0"
+      # uses: sqlc-dev/setup-sqlc@c0209b9199cd1cce6a14fc27cabcec491b651761 # v4.0.0
+      # with:
+      #   sqlc-version: "1.30.0"
+
+      # Switched to coder/sqlc fork to fix ambiguous column bug, see:
+      # - https://github.com/coder/sqlc/pull/1
+      # - https://github.com/sqlc-dev/sqlc/pull/4159
+      shell: bash
+      run: |
+        CGO_ENABLED=1 go install github.com/coder/sqlc/cmd/sqlc@aab4e865a51df0c43e1839f81a9d349b41d14f05
@@ -7,5 +7,5 @@ runs:
    - name: Install Terraform
      uses: hashicorp/setup-terraform@b9cd54a3c349d3f38e8881555d616ced269862dd # v3.1.2
      with:
-        terraform_version: 1.13.0
+        terraform_version: 1.13.4
        terraform_wrapper: false
@@ -119,9 +119,9 @@ updates:
    commit-message:
      prefix: "chore"
    groups:
-      coder:
+      coder-modules:
        patterns:
-          - "registry.coder.com/coder/*/coder"
+          - "coder/*/coder"
    labels: []
    ignore:
      - dependency-name: "*"
@@ -1,34 +0,0 @@
-app = "sao-paulo-coder"
-primary_region = "gru"
-
-[experimental]
-  entrypoint = ["/bin/sh", "-c", "CODER_DERP_SERVER_RELAY_URL=\"http://[${FLY_PRIVATE_IP}]:3000\" /opt/coder wsproxy server"]
-  auto_rollback = true
-
-[build]
-  image = "ghcr.io/coder/coder-preview:main"
-
-[env]
-  CODER_ACCESS_URL = "https://sao-paulo.fly.dev.coder.com"
-  CODER_HTTP_ADDRESS = "0.0.0.0:3000"
-  CODER_PRIMARY_ACCESS_URL = "https://dev.coder.com"
-  CODER_WILDCARD_ACCESS_URL = "*--apps.sao-paulo.fly.dev.coder.com"
-  CODER_VERBOSE = "true"
-
-[http_service]
-  internal_port = 3000
-  force_https = true
-  auto_stop_machines = true
-  auto_start_machines = true
-  min_machines_running = 0
-
-# Ref: https://fly.io/docs/reference/configuration/#http_service-concurrency
-[http_service.concurrency]
-  type = "requests"
-  soft_limit = 50
-  hard_limit = 100
-
-[[vm]]
-  cpu_kind = "shared"
-  cpus = 2
-  memory_mb = 512
@@ -35,12 +35,12 @@ jobs:
      tailnet-integration: ${{ steps.filter.outputs.tailnet-integration }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -124,7 +124,7 @@ jobs:
  #   runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
  #   steps:
  #     - name: Checkout
-  #       uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+  #       uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
  #       with:
  #         fetch-depth: 1
  #         # See: https://github.com/stefanzweifel/git-auto-commit-action?tab=readme-ov-file#commits-made-by-this-action-do-not-trigger-new-workflow-runs
@@ -157,12 +157,12 @@ jobs:
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -191,7 +191,7 @@ jobs:

      # Check for any typos
      - name: Check for typos
-        uses: crate-ci/typos@80c8a4945eec0f6d464eaf9e65ed98ef085283d1 # v1.38.1
+        uses: crate-ci/typos@2d0ce569feab1f8752f1dde43cc2f2aa53236e06 # v1.40.0
        with:
          config: .github/workflows/typos.toml

@@ -230,17 +230,17 @@ jobs:
        shell: bash

  gen:
-    timeout-minutes: 8
+    timeout-minutes: 20
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
    if: ${{ !cancelled() }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -271,6 +271,7 @@ jobs:
          popd

      - name: make gen
+        timeout-minutes: 8
        run: |
          # Remove golden files to detect discrepancy in generated files.
          make clean/golden-files
@@ -288,15 +289,15 @@ jobs:
    needs: changes
    if: needs.changes.outputs.offlinedocs-only == 'false' || needs.changes.outputs.ci == 'true' || github.ref == 'refs/heads/main'
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
-    timeout-minutes: 7
+    timeout-minutes: 20
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -315,6 +316,7 @@ jobs:
        run: go install mvdan.cc/sh/v3/cmd/shfmt@v3.7.0

      - name: make fmt
+        timeout-minutes: 7
        run: |
          PATH="${PATH}:$(go env GOPATH)/bin" \
            make --output-sync -j -B fmt
@@ -341,7 +343,7 @@ jobs:
          - windows-2022
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

@@ -367,7 +369,7 @@ jobs:
        uses: coder/setup-ramdisk-action@e1100847ab2d7bcd9d14bcda8f2d1b0f07b36f1b # v0.1.0

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -376,13 +378,6 @@ jobs:
        id: go-paths
        uses: ./.github/actions/setup-go-paths

-      - name: Download Go Build Cache
-        id: download-go-build-cache
-        uses: ./.github/actions/test-cache/download
-        with:
-          key-prefix: test-go-build-${{ runner.os }}-${{ runner.arch }}
-          cache-path: ${{ steps.go-paths.outputs.cached-dirs }}
-
      - name: Setup Go
        uses: ./.github/actions/setup-go
        with:
@@ -390,8 +385,7 @@ jobs:
          # download the toolchain configured in go.mod, so we don't
          # need to reinstall it. It's faster on Windows runners.
          use-preinstalled-go: ${{ runner.os == 'Windows' }}
-          # Cache is already downloaded above
-          use-cache: false
+          use-cache: true

      - name: Setup Terraform
        uses: ./.github/actions/setup-tf
@@ -500,17 +494,11 @@ jobs:
          make test

      - name: Upload failed test db dumps
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
        with:
          name: failed-test-db-dump-${{matrix.os}}
          path: "**/*.test.sql"

-      - name: Upload Go Build Cache
-        uses: ./.github/actions/test-cache/upload
-        with:
-          cache-key: ${{ steps.download-go-build-cache.outputs.cache-key }}
-          cache-path: ${{ steps.go-paths.outputs.cached-dirs }}
-
      - name: Upload Test Cache
        uses: ./.github/actions/test-cache/upload
        with:
@@ -544,12 +532,12 @@ jobs:
    timeout-minutes: 25
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -593,12 +581,12 @@ jobs:
    timeout-minutes: 25
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -653,12 +641,12 @@ jobs:
    timeout-minutes: 20
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -680,12 +668,12 @@ jobs:
    timeout-minutes: 20
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -713,12 +701,12 @@ jobs:
    name: ${{ matrix.variant.name }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -762,15 +750,23 @@ jobs:

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

+      - name: Upload debug log
+        if: always() && github.actor != 'dependabot[bot]' && runner.os == 'Linux' && !github.event.pull_request.head.repo.fork
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
+        with:
+          name: coderd-debug-logs${{ matrix.variant.premium && '-premium' || ''  }}
+          path: ./site/e2e/test-results/debug.log
+          retention-days: 7
+
      - name: Upload pprof dumps
        if: always() && github.actor != 'dependabot[bot]' && runner.os == 'Linux' && !github.event.pull_request.head.repo.fork
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
        with:
          name: debug-pprof-dumps${{ matrix.variant.premium && '-premium' || ''  }}
          path: ./site/test-results/**/debug-pprof-*.txt
@@ -785,12 +781,12 @@ jobs:
    if: needs.changes.outputs.site == 'true' || needs.changes.outputs.ci == 'true'
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          # 👇 Ensures Chromatic can read your full git history
          fetch-depth: 0
@@ -806,7 +802,7 @@ jobs:
      # the check to pass. This is desired in PRs, but not in mainline.
      - name: Publish to Chromatic (non-mainline)
        if: github.ref != 'refs/heads/main' && github.repository_owner == 'coder'
-        uses: chromaui/action@4ffe736a2a8262ea28067ff05a13b635ba31ec05 # v13.3.0
+        uses: chromaui/action@4c20b95e9d3209ecfdf9cd6aace6bbde71ba1694 # v13.3.4
        env:
          NODE_OPTIONS: "--max_old_space_size=4096"
          STORYBOOK: true
@@ -838,7 +834,7 @@ jobs:
      # infinitely "in progress" in mainline unless we re-review each build.
      - name: Publish to Chromatic (mainline)
        if: github.ref == 'refs/heads/main' && github.repository_owner == 'coder'
-        uses: chromaui/action@4ffe736a2a8262ea28067ff05a13b635ba31ec05 # v13.3.0
+        uses: chromaui/action@4c20b95e9d3209ecfdf9cd6aace6bbde71ba1694 # v13.3.4
        env:
          NODE_OPTIONS: "--max_old_space_size=4096"
          STORYBOOK: true
@@ -866,12 +862,12 @@ jobs:

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

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          # 0 is required here for version.sh to work.
          fetch-depth: 0
@@ -937,7 +933,7 @@ jobs:
    if: always()
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

@@ -975,7 +971,7 @@ jobs:
    steps:
      # Harden Runner doesn't work on macOS
      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -1036,7 +1032,7 @@ jobs:

      - name: Upload build artifacts
        if: ${{ github.repository_owner == 'coder' && (github.ref == 'refs/heads/main' || startsWith(github.ref, 'refs/heads/release/')) }}
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
        with:
          name: dylibs
          path: |
@@ -1057,12 +1053,12 @@ jobs:
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -1112,12 +1108,12 @@ jobs:
      IMAGE: ghcr.io/coder/coder-preview:${{ steps.build-docker.outputs.tag }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -1201,7 +1197,7 @@ jobs:
        uses: google-github-actions/setup-gcloud@aa5489c8933f4cc7a4f7d45035b3b1440c9c10db # v3.0.1

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

      - name: Upload build artifacts
        if: github.ref == 'refs/heads/main'
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
        with:
          name: coder
          path: |
@@ -1509,12 +1505,12 @@ jobs:
    if: needs.changes.outputs.db == 'true' || needs.changes.outputs.ci == 'true' || github.ref == 'refs/heads/main'
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -28,6 +28,7 @@ jobs:
          github-token: "${{ secrets.GITHUB_TOKEN }}"

      - name: Approve the PR
+        if: steps.metadata.outputs.package-ecosystem != 'github-actions'
        run: |
          echo "Approving $PR_URL"
          gh pr review --approve "$PR_URL"
@@ -36,6 +37,7 @@ jobs:
          GH_TOKEN: ${{secrets.GITHUB_TOKEN}}

      - name: Enable auto-merge
+        if: steps.metadata.outputs.package-ecosystem != 'github-actions'
        run: |
          echo "Enabling auto-merge for $PR_URL"
          gh pr merge --auto --squash "$PR_URL"
@@ -45,6 +47,11 @@ jobs:

      - name: Send Slack notification
        run: |
+          if [ "$PACKAGE_ECOSYSTEM" = "github-actions" ]; then
+            STATUS_TEXT=":pr-opened: Dependabot opened PR #${PR_NUMBER} (GitHub Actions changes are not auto-merged)"
+          else
+            STATUS_TEXT=":pr-merged: Auto merge enabled for Dependabot PR #${PR_NUMBER}"
+          fi
          curl -X POST -H 'Content-type: application/json' \
          --data '{
            "username": "dependabot",
@@ -54,7 +61,7 @@ jobs:
                "type": "header",
                "text": {
                  "type": "plain_text",
-                  "text": ":pr-merged: Auto merge enabled for Dependabot PR #'"${PR_NUMBER}"'",
+                  "text": "'"${STATUS_TEXT}"'",
                  "emoji": true
                }
              },
@@ -84,6 +91,7 @@ jobs:
          }' "${{ secrets.DEPENDABOT_PRS_SLACK_WEBHOOK }}"
        env:
          SLACK_WEBHOOK: ${{ secrets.DEPENDABOT_PRS_SLACK_WEBHOOK }}
+          PACKAGE_ECOSYSTEM: ${{ steps.metadata.outputs.package-ecosystem }}
          PR_NUMBER: ${{ github.event.pull_request.number }}
          PR_TITLE: ${{ github.event.pull_request.title }}
          PR_URL: ${{ github.event.pull_request.html_url }}
@@ -36,12 +36,12 @@ jobs:
      verdict: ${{ steps.check.outputs.verdict }} # DEPLOY or NOOP
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -65,12 +65,12 @@ jobs:
      packages: write # to retag image as dogfood
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -92,7 +92,7 @@ jobs:
        uses: google-github-actions/setup-gcloud@aa5489c8933f4cc7a4f7d45035b3b1440c9c10db # v3.0.1

      - name: Set up Flux CLI
-        uses: fluxcd/flux2/action@4a15fa6a023259353ef750acf1c98fe88407d4d0 # v2.7.2
+        uses: fluxcd/flux2/action@8454b02a32e48d775b9f563cb51fdcb1787b5b93 # v2.7.5
        with:
          # Keep this and the github action up to date with the version of flux installed in dogfood cluster
          version: "2.7.0"
@@ -146,12 +146,12 @@ jobs:
    needs: deploy
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -163,12 +163,10 @@ jobs:
        run: |
          flyctl deploy --image "$IMAGE" --app paris-coder --config ./.github/fly-wsproxies/paris-coder.toml --env "CODER_PROXY_SESSION_TOKEN=$TOKEN_PARIS" --yes
          flyctl deploy --image "$IMAGE" --app sydney-coder --config ./.github/fly-wsproxies/sydney-coder.toml --env "CODER_PROXY_SESSION_TOKEN=$TOKEN_SYDNEY" --yes
-          flyctl deploy --image "$IMAGE" --app sao-paulo-coder --config ./.github/fly-wsproxies/sao-paulo-coder.toml --env "CODER_PROXY_SESSION_TOKEN=$TOKEN_SAO_PAULO" --yes
          flyctl deploy --image "$IMAGE" --app jnb-coder --config ./.github/fly-wsproxies/jnb-coder.toml --env "CODER_PROXY_SESSION_TOKEN=$TOKEN_JNB" --yes
        env:
          FLY_API_TOKEN: ${{ secrets.FLY_API_TOKEN }}
          IMAGE: ${{ inputs.image }}
          TOKEN_PARIS: ${{ secrets.FLY_PARIS_CODER_PROXY_SESSION_TOKEN }}
          TOKEN_SYDNEY: ${{ secrets.FLY_SYDNEY_CODER_PROXY_SESSION_TOKEN }}
-          TOKEN_SAO_PAULO: ${{ secrets.FLY_SAO_PAULO_CODER_PROXY_SESSION_TOKEN }}
          TOKEN_JNB: ${{ secrets.FLY_JNB_CODER_PROXY_SESSION_TOKEN }}
@@ -0,0 +1,205 @@
+# This workflow checks if a PR requires documentation updates.
+# It creates a Coder Task that uses AI to analyze the PR changes,
+# search existing docs, and comment with recommendations.
+#
+# Triggered by: Adding the "doc-check" label to a PR, or manual dispatch.
+
+name: AI Documentation Check
+
+on:
+  pull_request:
+    types:
+      - labeled
+  workflow_dispatch:
+    inputs:
+      pr_url:
+        description: "Pull Request URL to check"
+        required: true
+        type: string
+      template_preset:
+        description: "Template preset to use"
+        required: false
+        default: ""
+        type: string
+
+jobs:
+  doc-check:
+    name: Analyze PR for Documentation Updates Needed
+    runs-on: ubuntu-latest
+    if: |
+      (github.event.label.name == 'doc-check' || github.event_name == 'workflow_dispatch') &&
+      (github.event.pull_request.draft == false || github.event_name == 'workflow_dispatch')
+    timeout-minutes: 30
+    env:
+      CODER_URL: ${{ secrets.DOC_CHECK_CODER_URL }}
+      CODER_SESSION_TOKEN: ${{ secrets.DOC_CHECK_CODER_SESSION_TOKEN }}
+    permissions:
+      contents: read
+      pull-requests: write
+      actions: write
+
+    steps:
+      - name: Determine PR Context
+        id: determine-context
+        env:
+          GITHUB_ACTOR: ${{ github.actor }}
+          GITHUB_EVENT_NAME: ${{ github.event_name }}
+          GITHUB_EVENT_PR_HTML_URL: ${{ github.event.pull_request.html_url }}
+          GITHUB_EVENT_PR_NUMBER: ${{ github.event.pull_request.number }}
+          GITHUB_EVENT_SENDER_ID: ${{ github.event.sender.id }}
+          GITHUB_EVENT_SENDER_LOGIN: ${{ github.event.sender.login }}
+          INPUTS_PR_URL: ${{ inputs.pr_url }}
+          INPUTS_TEMPLATE_PRESET: ${{ inputs.template_preset || '' }}
+          GH_TOKEN: ${{ github.token }}
+        run: |
+          echo "Using template preset: ${INPUTS_TEMPLATE_PRESET}"
+          echo "template_preset=${INPUTS_TEMPLATE_PRESET}" >> "${GITHUB_OUTPUT}"
+
+          # For workflow_dispatch, use the provided PR URL
+          if [[ "${GITHUB_EVENT_NAME}" == "workflow_dispatch" ]]; then
+            if ! GITHUB_USER_ID=$(gh api "users/${GITHUB_ACTOR}" --jq '.id'); then
+              echo "::error::Failed to get GitHub user ID for actor ${GITHUB_ACTOR}"
+              exit 1
+            fi
+            echo "Using workflow_dispatch actor: ${GITHUB_ACTOR} (ID: ${GITHUB_USER_ID})"
+            echo "github_user_id=${GITHUB_USER_ID}" >> "${GITHUB_OUTPUT}"
+            echo "github_username=${GITHUB_ACTOR}" >> "${GITHUB_OUTPUT}"
+
+            echo "Using PR URL: ${INPUTS_PR_URL}"
+            # Convert /pull/ to /issues/ for create-task-action compatibility
+            ISSUE_URL="${INPUTS_PR_URL/\/pull\//\/issues\/}"
+            echo "pr_url=${ISSUE_URL}" >> "${GITHUB_OUTPUT}"
+
+            # Extract PR number from URL for later use
+            PR_NUMBER=$(echo "${INPUTS_PR_URL}" | grep -oP '(?<=pull/)\d+')
+            echo "pr_number=${PR_NUMBER}" >> "${GITHUB_OUTPUT}"
+
+          elif [[ "${GITHUB_EVENT_NAME}" == "pull_request" ]]; then
+            GITHUB_USER_ID=${GITHUB_EVENT_SENDER_ID}
+            echo "Using label adder: ${GITHUB_EVENT_SENDER_LOGIN} (ID: ${GITHUB_USER_ID})"
+            echo "github_user_id=${GITHUB_USER_ID}" >> "${GITHUB_OUTPUT}"
+            echo "github_username=${GITHUB_EVENT_SENDER_LOGIN}" >> "${GITHUB_OUTPUT}"
+
+            echo "Using PR URL: ${GITHUB_EVENT_PR_HTML_URL}"
+            # Convert /pull/ to /issues/ for create-task-action compatibility
+            ISSUE_URL="${GITHUB_EVENT_PR_HTML_URL/\/pull\//\/issues\/}"
+            echo "pr_url=${ISSUE_URL}" >> "${GITHUB_OUTPUT}"
+            echo "pr_number=${GITHUB_EVENT_PR_NUMBER}" >> "${GITHUB_OUTPUT}"
+
+          else
+            echo "::error::Unsupported event type: ${GITHUB_EVENT_NAME}"
+            exit 1
+          fi
+
+      - name: Extract changed files and build prompt
+        id: extract-context
+        env:
+          PR_URL: ${{ steps.determine-context.outputs.pr_url }}
+          PR_NUMBER: ${{ steps.determine-context.outputs.pr_number }}
+          GH_TOKEN: ${{ github.token }}
+        run: |
+          echo "Analyzing PR #${PR_NUMBER}"
+
+          # Build task prompt - using unquoted heredoc so variables expand
+          TASK_PROMPT=$(cat <<EOF
+          Review PR #${PR_NUMBER} and determine if documentation needs updating or creating.
+
+          PR URL: ${PR_URL}
+
+          WORKFLOW:
+            1. Setup (repo is pre-cloned at ~/coder)
+               cd ~/coder
+               git fetch origin pull/${PR_NUMBER}/head:pr-${PR_NUMBER}
+               git checkout pr-${PR_NUMBER}
+
+            2. Get PR info
+               Use GitHub MCP tools to get PR title, body, and diff
+               Or use: git diff main...pr-${PR_NUMBER}
+
+            3. Understand Changes
+               Read the diff and identify what changed
+               Ask: Is this user-facing? Does it change behavior? Is it a new feature?
+
+            4. Search for Related Docs
+               cat ~/coder/docs/manifest.json | jq '.routes[] | {title, path}' | head -50
+               grep -ri "relevant_term" ~/coder/docs/ --include="*.md"
+
+            5. Decide
+               NEEDS DOCS if: New feature, API change, CLI change, behavior change, user-visible
+               NO DOCS if: Internal refactor, test-only, already documented, non-user-facing, dependency updates
+               FIRST check: Did this PR already update docs? If yes and complete, say "No Changes Needed"
+
+            6. Comment on the PR using this format
+
+          COMMENT FORMAT:
+          ## 📚 Documentation Check
+
+          ### ✅ Updates Needed
+          - **[docs/path/file.md](github_link)** - Brief what needs changing
+
+          ### 📝 New Docs Needed
+          - **docs/suggested/location.md** - What should be documented
+
+          ### ✨ No Changes Needed
+          [Reason: Documents already updated in PR | Internal changes only | Test-only | No user-facing impact]
+
+          ---
+          *This comment was generated by an AI Agent through [Coder Tasks](https://coder.com/docs/ai-coder/tasks)*
+
+          DOCS STRUCTURE:
+            Read ~/coder/docs/manifest.json for the complete documentation structure.
+            Common areas include: reference/, admin/, user-guides/, ai-coder/, install/, tutorials/
+            But check manifest.json - it has everything.
+
+          EOF
+          )
+
+          # Output the prompt
+          {
+            echo "task_prompt<<EOFOUTPUT"
+            echo "${TASK_PROMPT}"
+            echo "EOFOUTPUT"
+          } >> "${GITHUB_OUTPUT}"
+
+      - name: Checkout create-task-action
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
+        with:
+          fetch-depth: 1
+          path: ./.github/actions/create-task-action
+          persist-credentials: false
+          ref: main
+          repository: coder/create-task-action
+
+      - name: Create Coder Task for Documentation Check
+        id: create_task
+        uses: ./.github/actions/create-task-action
+        with:
+          coder-url: ${{ secrets.DOC_CHECK_CODER_URL }}
+          coder-token: ${{ secrets.DOC_CHECK_CODER_SESSION_TOKEN }}
+          coder-organization: "default"
+          coder-template-name: coder
+          coder-template-preset: ${{ steps.determine-context.outputs.template_preset }}
+          coder-task-name-prefix: doc-check
+          coder-task-prompt: ${{ steps.extract-context.outputs.task_prompt }}
+          github-user-id: ${{ steps.determine-context.outputs.github_user_id }}
+          github-token: ${{ github.token }}
+          github-issue-url: ${{ steps.determine-context.outputs.pr_url }}
+          comment-on-issue: true
+
+      - name: Write outputs
+        env:
+          TASK_CREATED: ${{ steps.create_task.outputs.task-created }}
+          TASK_NAME: ${{ steps.create_task.outputs.task-name }}
+          TASK_URL: ${{ steps.create_task.outputs.task-url }}
+          PR_URL: ${{ steps.determine-context.outputs.pr_url }}
+        run: |
+          {
+            echo "## Documentation Check Task"
+            echo ""
+            echo "**PR:** ${PR_URL}"
+            echo "**Task created:** ${TASK_CREATED}"
+            echo "**Task name:** ${TASK_NAME}"
+            echo "**Task URL:** ${TASK_URL}"
+            echo ""
+            echo "The Coder task is analyzing the PR changes and will comment with documentation recommendations."
+          } >> "${GITHUB_STEP_SUMMARY}"
@@ -38,12 +38,12 @@ jobs:
    if: github.repository_owner == 'coder'
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          persist-credentials: false

@@ -23,14 +23,14 @@ jobs:
    runs-on: ubuntu-latest
    steps:
      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          persist-credentials: false

      - name: Setup Node
        uses: ./.github/actions/setup-node

-      - uses: tj-actions/changed-files@d03a93c0dbfac6d6dd6a0d8a5e7daff992b07449 # v45.0.7
+      - uses: tj-actions/changed-files@abdd2f68ea150cee8f236d4a9fb4e0f2491abf1b # v45.0.7
        id: changed-files
        with:
          files: |
@@ -26,21 +26,21 @@ jobs:
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-4' || 'ubuntu-latest' }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          persist-credentials: false

      - name: Setup Nix
-        uses: nixbuild/nix-quick-install-action@1f095fee853b33114486cfdeae62fa099cda35a9 # v33
+        uses: nixbuild/nix-quick-install-action@2c9db80fb984ceb1bcaa77cdda3fdf8cfba92035 # v34
        with:
          # Pinning to 2.28 here, as Nix gets a "error: [json.exception.type_error.302] type must be array, but is string"
          # on version 2.29 and above.
-          nix_version: "2.28.4"
+          nix_version: "2.28.5"

      - uses: nix-community/cache-nix-action@135667ec418502fa5a3598af6fb9eb733888ce6a # v6.1.3
        with:
@@ -125,12 +125,12 @@ jobs:
      id-token: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          persist-credentials: false

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

@@ -53,7 +53,7 @@ jobs:
        uses: coder/setup-ramdisk-action@e1100847ab2d7bcd9d14bcda8f2d1b0f07b36f1b # v0.1.0

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -15,7 +15,7 @@ jobs:
    runs-on: ubuntu-latest
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

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

@@ -39,12 +39,12 @@ jobs:
      PR_OPEN: ${{ steps.check_pr.outputs.pr_open }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          persist-credentials: false

@@ -76,12 +76,12 @@ jobs:
    runs-on: "ubuntu-latest"
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -184,7 +184,7 @@ jobs:
      pull-requests: write # needed for commenting on PRs
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

@@ -228,12 +228,12 @@ jobs:
      CODER_IMAGE_TAG: ${{ needs.get_info.outputs.CODER_IMAGE_TAG }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -288,7 +288,7 @@ jobs:
      PR_HOSTNAME: "pr${{ needs.get_info.outputs.PR_NUMBER }}.${{ secrets.PR_DEPLOYMENTS_DOMAIN }}"
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

@@ -337,7 +337,7 @@ jobs:
          kubectl create namespace "pr${PR_NUMBER}"

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          persist-credentials: false

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

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

@@ -65,7 +65,7 @@ jobs:
    steps:
      # Harden Runner doesn't work on macOS.
      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -131,7 +131,7 @@ jobs:
          AC_CERTIFICATE_PASSWORD_FILE: /tmp/apple_cert_password.txt

      - name: Upload build artifacts
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
        with:
          name: dylibs
          path: |
@@ -164,12 +164,12 @@ jobs:
      version: ${{ steps.version.outputs.version }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -327,7 +327,7 @@ jobs:
        uses: google-github-actions/setup-gcloud@aa5489c8933f4cc7a4f7d45035b3b1440c9c10db # v3.0.1

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

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

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

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

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

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

@@ -888,7 +888,7 @@ jobs:
          GH_TOKEN: ${{ secrets.CDRCI_GITHUB_TOKEN }}

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -971,12 +971,12 @@ jobs:
    if: ${{ !inputs.dry_run }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 1
          persist-credentials: false
@@ -20,12 +20,12 @@ jobs:

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

      - name: "Checkout code"
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          persist-credentials: false

@@ -39,7 +39,7 @@ jobs:

      # Upload the results as artifacts.
      - name: "Upload artifact"
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
        with:
          name: SARIF file
          path: results.sarif
@@ -47,6 +47,6 @@ jobs:

      # Upload the results to GitHub's code scanning dashboard.
      - name: "Upload to code-scanning"
-        uses: github/codeql-action/upload-sarif@16140ae1a102900babc80a33c44059580f687047 # v3.29.5
+        uses: github/codeql-action/upload-sarif@fe4161a26a8629af62121b670040955b330f9af2 # v3.29.5
        with:
          sarif_file: results.sarif
@@ -27,12 +27,12 @@ jobs:
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          persist-credentials: false

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

      - name: Initialize CodeQL
-        uses: github/codeql-action/init@16140ae1a102900babc80a33c44059580f687047 # v3.29.5
+        uses: github/codeql-action/init@fe4161a26a8629af62121b670040955b330f9af2 # v3.29.5
        with:
          languages: go, javascript

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

      - name: Perform CodeQL Analysis
-        uses: github/codeql-action/analyze@16140ae1a102900babc80a33c44059580f687047 # v3.29.5
+        uses: github/codeql-action/analyze@fe4161a26a8629af62121b670040955b330f9af2 # v3.29.5

      - name: Send Slack notification on failure
        if: ${{ failure() }}
@@ -69,12 +69,12 @@ jobs:
    runs-on: ${{ github.repository_owner == 'coder' && 'depot-ubuntu-22.04-8' || 'ubuntu-latest' }}
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          fetch-depth: 0
          persist-credentials: false
@@ -154,13 +154,13 @@ jobs:
          severity: "CRITICAL,HIGH"

      - name: Upload Trivy scan results to GitHub Security tab
-        uses: github/codeql-action/upload-sarif@16140ae1a102900babc80a33c44059580f687047 # v3.29.5
+        uses: github/codeql-action/upload-sarif@fe4161a26a8629af62121b670040955b330f9af2 # v3.29.5
        with:
          sarif_file: trivy-results.sarif
          category: "Trivy"

      - name: Upload Trivy scan results as an artifact
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
        with:
          name: trivy
          path: trivy-results.sarif
@@ -18,7 +18,7 @@ jobs:
      pull-requests: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

@@ -96,12 +96,12 @@ jobs:
      contents: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout repository
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          persist-credentials: false
      - name: Run delete-old-branches-action
@@ -120,12 +120,12 @@ jobs:
      actions: write
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Delete PR Cleanup workflow runs
-        uses: Mattraks/delete-workflow-runs@39f0bbed25d76b34de5594dceab824811479e5de # v2.0.6
+        uses: Mattraks/delete-workflow-runs@5bf9a1dac5c4d041c029f0a8370ddf0c5cb5aeb7 # v2.1.0
        with:
          token: ${{ github.token }}
          repository: ${{ github.repository }}
@@ -134,7 +134,7 @@ jobs:
          delete_workflow_pattern: pr-cleanup.yaml

      - name: Delete PR Deploy workflow skipped runs
-        uses: Mattraks/delete-workflow-runs@39f0bbed25d76b34de5594dceab824811479e5de # v2.0.6
+        uses: Mattraks/delete-workflow-runs@5bf9a1dac5c4d041c029f0a8370ddf0c5cb5aeb7 # v2.1.0
        with:
          token: ${{ github.token }}
          repository: ${{ github.repository }}
@@ -17,8 +17,8 @@ on:
        type: string
      template_preset:
        description: "Template preset to use"
-        required: true
-        default: "none"
+        required: false
+        default: ""
        type: string
      prefix:
        description: "Prefix for workspace name"
@@ -67,7 +67,7 @@ jobs:
          GITHUB_EVENT_USER_LOGIN: ${{ github.event.sender.login }}
          INPUTS_ISSUE_URL: ${{ inputs.issue_url }}
          INPUTS_TEMPLATE_NAME: ${{ inputs.template_name || 'coder' }}
-          INPUTS_TEMPLATE_PRESET: ${{ inputs.template_preset || 'none'}}
+          INPUTS_TEMPLATE_PRESET: ${{ inputs.template_preset || ''}}
          INPUTS_PREFIX: ${{ inputs.prefix || 'traiage' }}
          GH_TOKEN: ${{ github.token }}
        run: |
@@ -124,7 +124,7 @@ jobs:
            exit 1
          fi

-      - name: Extract context key from issue
+      - name: Extract context key and description from issue
        id: extract-context
        env:
          ISSUE_URL: ${{ steps.determine-inputs.outputs.issue_url }}
@@ -132,86 +132,59 @@ jobs:
        run: |
          issue_number="$(gh issue view "${ISSUE_URL}" --json number --jq '.number')"
          context_key="gh-${issue_number}"
-          echo "context_key=${context_key}" >> "${GITHUB_OUTPUT}"
-          echo "CONTEXT_KEY=${context_key}" >> "${GITHUB_ENV}"

-      - name: Download and install Coder binary
-        shell: bash
-        env:
-          CODER_URL: ${{ secrets.TRAIAGE_CODER_URL }}
-        run: |
-          if [ "${{ runner.arch }}" == "ARM64" ]; then
-            ARCH="arm64"
-          else
-            ARCH="amd64"
-          fi
-          mkdir -p "${HOME}/.local/bin"
-          curl -fsSL --compressed "$CODER_URL/bin/coder-linux-${ARCH}" -o "${HOME}/.local/bin/coder"
-          chmod +x "${HOME}/.local/bin/coder"
-          export PATH="$HOME/.local/bin:$PATH"
-          coder version
-          coder whoami
-          echo "$HOME/.local/bin" >> "${GITHUB_PATH}"
-
-      - name: Get Coder username from GitHub actor
-        id: get-coder-username
-        env:
-          CODER_SESSION_TOKEN: ${{ secrets.TRAIAGE_CODER_SESSION_TOKEN }}
-          GH_TOKEN: ${{ github.token }}
-          GITHUB_USER_ID: ${{ steps.determine-inputs.outputs.github_user_id }}
-        run: |
-          user_json=$(
-            coder users list --github-user-id="${GITHUB_USER_ID}" --output=json
-          )
-          coder_username=$(jq -r 'first | .username' <<< "$user_json")
-          [[ -z "${coder_username}" || "${coder_username}" == "null" ]] && echo "No Coder user with GitHub user ID ${GITHUB_USER_ID} found" && exit 1
-          echo "coder_username=${coder_username}" >> "${GITHUB_OUTPUT}"
-
-      - name: Checkout repository
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
-        with:
-          persist-credentials: false
-          fetch-depth: 0
-
-      # TODO(Cian): this is a good use-case for 'recipes'
-      - name: Create Coder task
-        id: create-task
-        env:
-          CODER_USERNAME: ${{ steps.get-coder-username.outputs.coder_username }}
-          CONTEXT_KEY: ${{ steps.extract-context.outputs.context_key }}
-          GH_TOKEN: ${{ github.token }}
-          GITHUB_REPOSITORY: ${{ github.repository }}
-          ISSUE_URL: ${{ steps.determine-inputs.outputs.issue_url }}
-          PREFIX: ${{ steps.determine-inputs.outputs.prefix }}
-          RUN_ID: ${{ github.run_id }}
-          TEMPLATE_NAME: ${{ steps.determine-inputs.outputs.template_name }}
-          TEMPLATE_PARAMETERS: ${{ secrets.TRAIAGE_TEMPLATE_PARAMETERS }}
-          TEMPLATE_PRESET: ${{ steps.determine-inputs.outputs.template_preset }}
-        run: |
-          # Fetch issue description using `gh` CLI
-          #shellcheck disable=SC2016 # The template string should not be subject to shell expansion
-          issue_description=$(gh issue view "${ISSUE_URL}" \
-            --json 'title,body,comments' \
-            --template '{{printf "%s\n\n%s\n\nComments:\n" .title .body}}{{range $k, $v := .comments}}  - {{index $v.author "login"}}: {{printf "%s\n" $v.body}}{{end}}')
-
-          # Write a prompt to PROMPT_FILE
-          PROMPT=$(cat <<EOF
+          TASK_PROMPT=$(cat <<EOF
          Fix ${ISSUE_URL}

-          Analyze the below GitHub issue description, understand the root cause, and make appropriate changes to resolve the issue.
-          ---
-          ${issue_description}
+            1. Use the gh CLI to read the issue description and comments.
+            2. Think carefully and try to understand the root cause. If the issue is unclear or not well defined, ask me to clarify and provide more information.
+            3. Write a proposed implementation plan to PLAN.md for me to review before starting implementation. Your plan should use TDD and only make the minimal changes necessary to fix the root cause.
+            4. When I approve your plan, start working on it. If you encounter issues with the plan, ask me for clarification and update the plan as required.
+            5. When you have finished implementation according to the plan, commit and push your changes, and create a PR using the gh CLI for me to review.
+
          EOF
          )
-          export PROMPT

-          export TASK_NAME="${PREFIX}-${CONTEXT_KEY}-${RUN_ID}"
-          echo "Creating task: $TASK_NAME"
-          ./scripts/traiage.sh create
-          if [[ "${ISSUE_URL}" == "https://github.com/${GITHUB_REPOSITORY}"* ]]; then
-            gh issue comment "${ISSUE_URL}" --body "Task created: https://dev.coder.com/tasks/${CODER_USERNAME}/${TASK_NAME}" --create-if-none --edit-last
-          else
-            echo "Skipping comment on other repo."
-          fi
-          echo "TASK_NAME=${CODER_USERNAME}/${TASK_NAME}" >> "${GITHUB_OUTPUT}"
-          echo "TASK_NAME=${CODER_USERNAME}/${TASK_NAME}" >> "${GITHUB_ENV}"
+          echo "context_key=${context_key}" >> "${GITHUB_OUTPUT}"
+          {
+            echo "TASK_PROMPT<<EOF"
+            echo "${TASK_PROMPT}"
+            echo "EOF"
+          } >> "${GITHUB_OUTPUT}"
+
+      - name: Checkout repository
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
+        with:
+          fetch-depth: 1
+          path: ./.github/actions/create-task-action
+          persist-credentials: false
+          ref: main
+          repository: coder/create-task-action
+
+      - name: Create Coder Task
+        id: create_task
+        uses: ./.github/actions/create-task-action
+        with:
+          coder-url: ${{ secrets.TRAIAGE_CODER_URL }}
+          coder-token: ${{ secrets.TRAIAGE_CODER_SESSION_TOKEN }}
+          coder-organization: "default"
+          coder-template-name: coder
+          coder-template-preset: ${{ steps.determine-inputs.outputs.template_preset }}
+          coder-task-name-prefix: gh-coder
+          coder-task-prompt: ${{ steps.extract-context.outputs.task_prompt }}
+          github-user-id: ${{ steps.determine-inputs.outputs.github_user_id }}
+          github-token: ${{ github.token }}
+          github-issue-url: ${{ steps.determine-inputs.outputs.issue_url }}
+          comment-on-issue: ${{ startsWith(steps.determine-inputs.outputs.issue_url, format('{0}/{1}', github.server_url, github.repository)) }}
+
+      - name: Write outputs
+        env:
+          TASK_CREATED: ${{ steps.create_task.outputs.task-created }}
+          TASK_NAME: ${{ steps.create_task.outputs.task-name }}
+          TASK_URL: ${{ steps.create_task.outputs.task-url }}
+        run: |
+          {
+            echo "**Task created:** ${TASK_CREATED}"
+            echo "**Task name:**    ${TASK_NAME}"
+            echo "**Task URL**:     ${TASK_URL}"
+          } >> "${GITHUB_STEP_SUMMARY}"
@@ -9,6 +9,7 @@ IST = "IST"
 MacOS = "macOS"
 AKS = "AKS"
 O_WRONLY = "O_WRONLY"
+AIBridge = "AI Bridge"

 [default.extend-words]
 AKS = "AKS"
@@ -21,12 +21,12 @@ jobs:
      pull-requests: write # required to post PR review comments by the action
    steps:
      - name: Harden Runner
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@95d9a5deda9de15063e7595e9719c11c38c90ae2 # v2.13.2
        with:
          egress-policy: audit

      - name: Checkout
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
        with:
          persist-credentials: false

@@ -89,3 +89,11 @@ result
 __debug_bin*

 **/.claude/settings.local.json
+
+# Local agent configuration
+AGENTS.local.md
+
+/.env
+
+# Ignore plans written by AI agents.
+PLAN.md
@@ -140,13 +140,53 @@ seems like it should use `time.Sleep`, read through https://github.com/coder/qua
 - Follow [Uber Go Style Guide](https://github.com/uber-go/guide/blob/master/style.md)
 - Commit format: `type(scope): message`

+### Writing Comments
+
+Code comments should be clear, well-formatted, and add meaningful context.
+
+**Proper sentence structure**: Comments are sentences and should end with
+periods or other appropriate punctuation. This improves readability and
+maintains professional code standards.
+
+**Explain why, not what**: Good comments explain the reasoning behind code
+rather than describing what the code does. The code itself should be
+self-documenting through clear naming and structure. Focus your comments on
+non-obvious decisions, edge cases, or business logic that isn't immediately
+apparent from reading the implementation.
+
+**Line length and wrapping**: Keep comment lines to 80 characters wide
+(including the comment prefix like `//` or `#`). When a comment spans multiple
+lines, wrap it naturally at word boundaries rather than writing one sentence
+per line. This creates more readable, paragraph-like blocks of documentation.
+
+```go
+// Good: Explains the rationale with proper sentence structure.
+// We need a custom timeout here because workspace builds can take several
+// minutes on slow networks, and the default 30s timeout causes false
+// failures during initial template imports.
+ctx, cancel := context.WithTimeout(ctx, 5*time.Minute)
+
+// Bad: Describes what the code does without punctuation or wrapping
+// Set a custom timeout
+// Workspace builds can take a long time
+// Default timeout is too short
+ctx, cancel := context.WithTimeout(ctx, 5*time.Minute)
+```
+
 ## Detailed Development Guides

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

+## Local Configuration
+
+These files may be gitignored, read manually if not auto-loaded.
+
+@AGENTS.local.md
+
 ## Common Pitfalls

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

-site/ @aslilac @Parkreiner
-site/src/hooks/ @Parkreiner
-# These rules intentionally do not specify any owners. More specific rules
-# override less specific rules, so these files are "ignored" by the site/ rule.
-site/e2e/google/protobuf/timestampGenerated.ts
-site/e2e/provisionerGenerated.ts
-site/src/api/countriesGenerated.ts
-site/src/api/rbacresourcesGenerated.ts
-site/src/api/typesGenerated.ts
-site/src/testHelpers/entities.ts
-site/CLAUDE.md
-
 # The blood and guts of the autostop algorithm, which is quite complex and
 # requires elite ball knowledge of most of the scheduling code to make changes
 # without inadvertently affecting other parts of the codebase.
@@ -39,3 +27,5 @@ coderd/schedule/autostop.go @deansheather @DanielleMaywood
 # well as guidance from revenue.
 coderd/usage/ @deansheather @spikecurtis
 enterprise/coderd/usage/ @deansheather @spikecurtis
+
+.github/ 	@jdomeracki-coder
@@ -636,8 +636,8 @@ TAILNETTEST_MOCKS := \
 	tailnet/tailnettest/subscriptionmock.go

 AIBRIDGED_MOCKS := \
-	enterprise/x/aibridged/aibridgedmock/clientmock.go \
-	enterprise/x/aibridged/aibridgedmock/poolmock.go
+	enterprise/aibridged/aibridgedmock/clientmock.go \
+	enterprise/aibridged/aibridgedmock/poolmock.go

 GEN_FILES := \
 	tailnet/proto/tailnet.pb.go \
@@ -646,7 +646,7 @@ GEN_FILES := \
 	provisionersdk/proto/provisioner.pb.go \
 	provisionerd/proto/provisionerd.pb.go \
 	vpn/vpn.pb.go \
-	enterprise/x/aibridged/proto/aibridged.pb.go \
+	enterprise/aibridged/proto/aibridged.pb.go \
 	$(DB_GEN_FILES) \
 	$(SITE_GEN_FILES) \
 	coderd/rbac/object_gen.go \
@@ -697,8 +697,9 @@ gen/mark-fresh:
 		agent/proto/agent.pb.go \
 		provisionersdk/proto/provisioner.pb.go \
 		provisionerd/proto/provisionerd.pb.go \
+		agent/agentsocket/proto/agentsocket.pb.go \
 		vpn/vpn.pb.go \
-		enterprise/x/aibridged/proto/aibridged.pb.go \
+		enterprise/aibridged/proto/aibridged.pb.go \
 		coderd/database/dump.sql \
 		$(DB_GEN_FILES) \
 		site/src/api/typesGenerated.ts \
@@ -769,8 +770,8 @@ codersdk/workspacesdk/agentconnmock/agentconnmock.go: codersdk/workspacesdk/agen
 	go generate ./codersdk/workspacesdk/agentconnmock/
 	touch "$@"

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

 agent/agentcontainers/dcspec/dcspec_gen.go: \
@@ -831,13 +832,13 @@ vpn/vpn.pb.go: vpn/vpn.proto
 		--go_opt=paths=source_relative \
 		./vpn/vpn.proto

-enterprise/x/aibridged/proto/aibridged.pb.go: enterprise/x/aibridged/proto/aibridged.proto
+enterprise/aibridged/proto/aibridged.pb.go: enterprise/aibridged/proto/aibridged.proto
 	protoc \
 		--go_out=. \
 		--go_opt=paths=source_relative \
 		--go-drpc_out=. \
 		--go-drpc_opt=paths=source_relative \
-		./enterprise/x/aibridged/proto/aibridged.proto
+		./enterprise/aibridged/proto/aibridged.proto

 site/src/api/typesGenerated.ts: site/node_modules/.installed $(wildcard scripts/apitypings/*) $(shell find ./codersdk $(FIND_EXCLUSIONS) -type f -name '*.go')
 	# -C sets the directory for the go run command
@@ -1191,3 +1192,8 @@ endif

 dogfood/coder/nix.hash: flake.nix flake.lock
 	sha256sum flake.nix flake.lock >./dogfood/coder/nix.hash
+
+# Count the number of test databases created per test package.
+count-test-databases:
+	PGPASSWORD=postgres psql -h localhost -U postgres -d coder_testing -P pager=off -c 'SELECT test_package, count(*) as count from test_databases GROUP BY test_package ORDER BY count DESC'
+.PHONY: count-test-databases
@@ -8,6 +8,7 @@ import (
 	"fmt"
 	"hash/fnv"
 	"io"
+	"maps"
 	"net"
 	"net/http"
 	"net/netip"
@@ -71,16 +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
@@ -92,7 +98,8 @@ type Options struct {
 	Devcontainers                bool
 	DevcontainerAPIOptions       []agentcontainers.Option // Enable Devcontainers for these to be effective.
 	Clock                        quartz.Clock
-	SocketPath                   string // Path for the agent socket server
+	SocketServerEnabled          bool
+	SocketPath                   string // Path for the agent socket server socket
 }

 type Client interface {
@@ -139,9 +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()
 	}
@@ -155,30 +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,
@@ -193,6 +206,7 @@ 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
@@ -205,20 +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
@@ -275,8 +285,9 @@ type agent struct {
 	containerAPIOptions []agentcontainers.Option
 	containerAPI        *agentcontainers.API

-	socketPath   string
-	socketServer *agentsocket.Server
+	socketServerEnabled bool
+	socketPath          string
+	socketServer        *agentsocket.Server
 }

 func (a *agent) TailnetConn() *tailnet.Conn {
@@ -364,20 +375,17 @@ func (a *agent) init() {

 // initSocketServer initializes server that allows direct communication with a workspace agent using IPC.
 func (a *agent) initSocketServer() {
-	if a.socketPath == "" {
-		a.logger.Info(a.hardCtx, "socket server disabled (no path configured)")
+	if !a.socketServerEnabled {
+		a.logger.Info(a.hardCtx, "socket server is disabled")
 		return
 	}

-	server, err := agentsocket.NewServer(a.socketPath, a.logger.Named("socket"))
+	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))
-		return
-	}
-
-	err = server.Start()
-	if err != nil {
-		a.logger.Warn(a.hardCtx, "failed to start socket server", slog.Error(err))
+		a.logger.Warn(a.hardCtx, "failed to create socket server", slog.Error(err), slog.F("path", a.socketPath))
 		return
 	}

@@ -1119,7 +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))
@@ -1953,12 +1961,6 @@ func (a *agent) Close() error {
 		}
 	}

-	if a.socketServer != nil {
-		if err := a.socketServer.Stop(); err != nil {
-			a.logger.Error(a.hardCtx, "socket server close", slog.Error(err))
-		}
-	}
-
 	a.setLifecycle(lifecycleState)

 	err = a.scriptRunner.Close()
@@ -1966,6 +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))
 	}
@@ -682,8 +682,6 @@ func (api *API) updaterLoop() {
 			} else {
 				prevErr = nil
 			}
-		default:
-			api.logger.Debug(api.ctx, "updater loop ticker skipped, update in progress")
 		}

 		return nil // Always nil to keep the ticker going.
@@ -1041,6 +1039,10 @@ func (api *API) processUpdatedContainersLocked(ctx context.Context, updated code
 					logger.Error(ctx, "inject subagent into container failed", slog.Error(err))
 					dc.Error = err.Error()
 				} else {
+					// TODO(mafredri): Preserve the error from devcontainer
+					// up if it was a lifecycle script error. Currently
+					// this results in a brief flicker for the user if
+					// injection is fast, as the error is shown then erased.
 					dc.Error = ""
 				}
 			}
@@ -1349,27 +1351,41 @@ func (api *API) CreateDevcontainer(workspaceFolder, configPath string, opts ...D
 	upOptions := []DevcontainerCLIUpOptions{WithUpOutput(infoW, errW)}
 	upOptions = append(upOptions, opts...)

-	_, err := api.dccli.Up(ctx, dc.WorkspaceFolder, configPath, upOptions...)
-	if err != nil {
+	containerID, upErr := api.dccli.Up(ctx, dc.WorkspaceFolder, configPath, upOptions...)
+	if upErr != nil {
 		// No need to log if the API is closing (context canceled), as this
 		// is expected behavior when the API is shutting down.
-		if !errors.Is(err, context.Canceled) {
-			logger.Error(ctx, "devcontainer creation failed", slog.Error(err))
+		if !errors.Is(upErr, context.Canceled) {
+			logger.Error(ctx, "devcontainer creation failed", slog.Error(upErr))
 		}

-		api.mu.Lock()
-		dc = api.knownDevcontainers[dc.WorkspaceFolder]
-		dc.Status = codersdk.WorkspaceAgentDevcontainerStatusError
-		dc.Error = err.Error()
-		api.knownDevcontainers[dc.WorkspaceFolder] = dc
-		api.recreateErrorTimes[dc.WorkspaceFolder] = api.clock.Now("agentcontainers", "recreate", "errorTimes")
-		api.mu.Unlock()
+		// If we don't have a container ID, the error is fatal, so we
+		// should mark the devcontainer as errored and return.
+		if containerID == "" {
+			api.mu.Lock()
+			dc = api.knownDevcontainers[dc.WorkspaceFolder]
+			dc.Status = codersdk.WorkspaceAgentDevcontainerStatusError
+			dc.Error = upErr.Error()
+			api.knownDevcontainers[dc.WorkspaceFolder] = dc
+			api.recreateErrorTimes[dc.WorkspaceFolder] = api.clock.Now("agentcontainers", "recreate", "errorTimes")
+			api.broadcastUpdatesLocked()
+			api.mu.Unlock()

-		return xerrors.Errorf("start devcontainer: %w", err)
+			return xerrors.Errorf("start devcontainer: %w", upErr)
+		}
+
+		// If we have a container ID, it means the container was created
+		// but a lifecycle script (e.g. postCreateCommand) failed. In this
+		// case, we still want to refresh containers to pick up the new
+		// container, inject the agent, and allow the user to debug the
+		// issue. We store the error to surface it to the user.
+		logger.Warn(ctx, "devcontainer created with errors (e.g. lifecycle script failure), container is available",
+			slog.F("container_id", containerID),
+		)
+	} else {
+		logger.Info(ctx, "devcontainer created successfully")
 	}

-	logger.Info(ctx, "devcontainer created successfully")
-
 	api.mu.Lock()
 	dc = api.knownDevcontainers[dc.WorkspaceFolder]
 	// Update the devcontainer status to Running or Stopped based on the
@@ -1378,13 +1394,18 @@ func (api *API) CreateDevcontainer(workspaceFolder, configPath string, opts ...D
 	// to minimize the time between API consistency, we guess the status
 	// based on the container state.
 	dc.Status = codersdk.WorkspaceAgentDevcontainerStatusStopped
-	if dc.Container != nil {
-		if dc.Container.Running {
-			dc.Status = codersdk.WorkspaceAgentDevcontainerStatusRunning
-		}
+	if dc.Container != nil && dc.Container.Running {
+		dc.Status = codersdk.WorkspaceAgentDevcontainerStatusRunning
 	}
 	dc.Dirty = false
-	dc.Error = ""
+	if upErr != nil {
+		// If there was a lifecycle script error but we have a container ID,
+		// the container is running so we should set the status to Running.
+		dc.Status = codersdk.WorkspaceAgentDevcontainerStatusRunning
+		dc.Error = upErr.Error()
+	} else {
+		dc.Error = ""
+	}
 	api.recreateSuccessTimes[dc.WorkspaceFolder] = api.clock.Now("agentcontainers", "recreate", "successTimes")
 	api.knownDevcontainers[dc.WorkspaceFolder] = dc
 	api.broadcastUpdatesLocked()
@@ -234,6 +234,8 @@ func (w *fakeWatcher) sendEventWaitNextCalled(ctx context.Context, event fsnotif
 // fakeSubAgentClient implements SubAgentClient for testing purposes.
 type fakeSubAgentClient struct {
 	logger slog.Logger
+
+	mu     sync.Mutex // Protects following.
 	agents map[uuid.UUID]agentcontainers.SubAgent

 	listErrC   chan error // If set, send to return error, close to return nil.
@@ -254,6 +256,8 @@ func (m *fakeSubAgentClient) List(ctx context.Context) ([]agentcontainers.SubAge
 			}
 		}
 	}
+	m.mu.Lock()
+	defer m.mu.Unlock()
 	var agents []agentcontainers.SubAgent
 	for _, agent := range m.agents {
 		agents = append(agents, agent)
@@ -283,6 +287,9 @@ func (m *fakeSubAgentClient) Create(ctx context.Context, agent agentcontainers.S
 		return agentcontainers.SubAgent{}, xerrors.New("operating system must be set")
 	}

+	m.mu.Lock()
+	defer m.mu.Unlock()
+
 	for _, a := range m.agents {
 		if a.Name == agent.Name {
 			return agentcontainers.SubAgent{}, &pq.Error{
@@ -314,6 +321,8 @@ func (m *fakeSubAgentClient) Delete(ctx context.Context, id uuid.UUID) error {
 			}
 		}
 	}
+	m.mu.Lock()
+	defer m.mu.Unlock()
 	if m.agents == nil {
 		m.agents = make(map[uuid.UUID]agentcontainers.SubAgent)
 	}
@@ -2070,6 +2079,122 @@ func TestAPI(t *testing.T) {
 			require.Equal(t, "", response.Devcontainers[0].Error)
 		})

+		// This test verifies that when devcontainer up fails due to a
+		// lifecycle script error (such as postCreateCommand failing) but the
+		// container was successfully created, we still proceed with the
+		// devcontainer. The container should be available for use and the
+		// agent should be injected.
+		t.Run("DuringUpWithContainerID", func(t *testing.T) {
+			t.Parallel()
+
+			var (
+				ctx    = testutil.Context(t, testutil.WaitMedium)
+				logger = slogtest.Make(t, &slogtest.Options{IgnoreErrors: true}).Leveled(slog.LevelDebug)
+				mClock = quartz.NewMock(t)
+
+				testContainer = codersdk.WorkspaceAgentContainer{
+					ID:           "test-container-id",
+					FriendlyName: "test-container",
+					Image:        "test-image",
+					Running:      true,
+					CreatedAt:    time.Now(),
+					Labels: map[string]string{
+						agentcontainers.DevcontainerLocalFolderLabel: "/workspaces/project",
+						agentcontainers.DevcontainerConfigFileLabel:  "/workspaces/project/.devcontainer/devcontainer.json",
+					},
+				}
+				fCCLI = &fakeContainerCLI{
+					containers: codersdk.WorkspaceAgentListContainersResponse{
+						Containers: []codersdk.WorkspaceAgentContainer{testContainer},
+					},
+					arch: "amd64",
+				}
+				fDCCLI = &fakeDevcontainerCLI{
+					upID:   testContainer.ID,
+					upErrC: make(chan func() error, 1),
+				}
+				fSAC = &fakeSubAgentClient{
+					logger: logger.Named("fakeSubAgentClient"),
+				}
+
+				testDevcontainer = codersdk.WorkspaceAgentDevcontainer{
+					ID:              uuid.New(),
+					Name:            "test-devcontainer",
+					WorkspaceFolder: "/workspaces/project",
+					ConfigPath:      "/workspaces/project/.devcontainer/devcontainer.json",
+					Status:          codersdk.WorkspaceAgentDevcontainerStatusStopped,
+				}
+			)
+
+			mClock.Set(time.Now()).MustWait(ctx)
+			tickerTrap := mClock.Trap().TickerFunc("updaterLoop")
+			nowRecreateSuccessTrap := mClock.Trap().Now("recreate", "successTimes")
+
+			api := agentcontainers.NewAPI(logger,
+				agentcontainers.WithClock(mClock),
+				agentcontainers.WithContainerCLI(fCCLI),
+				agentcontainers.WithDevcontainerCLI(fDCCLI),
+				agentcontainers.WithDevcontainers(
+					[]codersdk.WorkspaceAgentDevcontainer{testDevcontainer},
+					[]codersdk.WorkspaceAgentScript{{ID: testDevcontainer.ID, LogSourceID: uuid.New()}},
+				),
+				agentcontainers.WithSubAgentClient(fSAC),
+				agentcontainers.WithSubAgentURL("test-subagent-url"),
+				agentcontainers.WithWatcher(watcher.NewNoop()),
+			)
+			api.Start()
+			defer func() {
+				close(fDCCLI.upErrC)
+				api.Close()
+			}()
+
+			r := chi.NewRouter()
+			r.Mount("/", api.Routes())
+
+			tickerTrap.MustWait(ctx).MustRelease(ctx)
+			tickerTrap.Close()
+
+			// Send a recreate request to trigger devcontainer up.
+			req := httptest.NewRequest(http.MethodPost, "/devcontainers/"+testDevcontainer.ID.String()+"/recreate", nil)
+			rec := httptest.NewRecorder()
+			r.ServeHTTP(rec, req)
+			require.Equal(t, http.StatusAccepted, rec.Code)
+
+			// Simulate a lifecycle script failure. The devcontainer CLI
+			// will return an error but also provide a container ID since
+			// the container was created before the script failed.
+			simulatedError := xerrors.New("postCreateCommand failed with exit code 1")
+			testutil.RequireSend(ctx, t, fDCCLI.upErrC, func() error { return simulatedError })
+
+			// Wait for the recreate operation to complete. We expect it to
+			// record a success time because the container was created.
+			nowRecreateSuccessTrap.MustWait(ctx).MustRelease(ctx)
+			nowRecreateSuccessTrap.Close()
+
+			// Advance the clock to run the devcontainer state update routine.
+			_, aw := mClock.AdvanceNext()
+			aw.MustWait(ctx)
+
+			req = httptest.NewRequest(http.MethodGet, "/", nil)
+			rec = httptest.NewRecorder()
+			r.ServeHTTP(rec, req)
+			require.Equal(t, http.StatusOK, rec.Code)
+
+			var response codersdk.WorkspaceAgentListContainersResponse
+			err := json.NewDecoder(rec.Body).Decode(&response)
+			require.NoError(t, err)
+
+			// Verify that the devcontainer is running and has the container
+			// associated with it despite the lifecycle script error. The
+			// error may be cleared during refresh if agent injection
+			// succeeds, but the important thing is that the container is
+			// available for use.
+			require.Len(t, response.Devcontainers, 1)
+			assert.Equal(t, codersdk.WorkspaceAgentDevcontainerStatusRunning, response.Devcontainers[0].Status)
+			require.NotNil(t, response.Devcontainers[0].Container)
+			assert.Equal(t, testContainer.ID, response.Devcontainers[0].Container.ID)
+		})
+
 		t.Run("DuringInjection", func(t *testing.T) {
 			t.Parallel()

@@ -263,11 +263,14 @@ func (d *devcontainerCLI) Up(ctx context.Context, workspaceFolder, configPath st
 	}

 	if err := cmd.Run(); err != nil {
-		_, err2 := parseDevcontainerCLILastLine[devcontainerCLIResult](ctx, logger, stdoutBuf.Bytes())
+		result, err2 := parseDevcontainerCLILastLine[devcontainerCLIResult](ctx, logger, stdoutBuf.Bytes())
 		if err2 != nil {
 			err = errors.Join(err, err2)
 		}
-		return "", err
+		// Return the container ID if available, even if there was an error.
+		// This can happen if the container was created successfully but a
+		// lifecycle script (e.g. postCreateCommand) failed.
+		return result.ContainerID, err
 	}

 	result, err := parseDevcontainerCLILastLine[devcontainerCLIResult](ctx, logger, stdoutBuf.Bytes())
@@ -275,6 +278,13 @@ func (d *devcontainerCLI) Up(ctx context.Context, workspaceFolder, configPath st
 		return "", err
 	}

+	// Check if the result indicates an error (e.g. lifecycle script failure)
+	// but still has a container ID, allowing the caller to potentially
+	// continue with the container that was created.
+	if err := result.Err(); err != nil {
+		return result.ContainerID, err
+	}
+
 	return result.ContainerID, nil
 }

@@ -394,7 +404,10 @@ func parseDevcontainerCLILastLine[T any](ctx context.Context, logger slog.Logger
 type devcontainerCLIResult struct {
 	Outcome string `json:"outcome"` // "error", "success".

-	// The following fields are set if outcome is success.
+	// The following fields are typically set if outcome is success, but
+	// ContainerID may also be present when outcome is error if the
+	// container was created but a lifecycle script (e.g. postCreateCommand)
+	// failed.
 	ContainerID           string `json:"containerId"`
 	RemoteUser            string `json:"remoteUser"`
 	RemoteWorkspaceFolder string `json:"remoteWorkspaceFolder"`
@@ -404,18 +417,6 @@ type devcontainerCLIResult struct {
 	Description string `json:"description"`
 }

-func (r *devcontainerCLIResult) UnmarshalJSON(data []byte) error {
-	type wrapperResult devcontainerCLIResult
-
-	var wrappedResult wrapperResult
-	if err := json.Unmarshal(data, &wrappedResult); err != nil {
-		return err
-	}
-
-	*r = devcontainerCLIResult(wrappedResult)
-	return r.Err()
-}
-
 func (r devcontainerCLIResult) Err() error {
 	if r.Outcome == "success" {
 		return nil
@@ -42,56 +42,63 @@ func TestDevcontainerCLI_ArgsAndParsing(t *testing.T) {
 		t.Parallel()

 		tests := []struct {
-			name      string
-			logFile   string
-			workspace string
-			config    string
-			opts      []agentcontainers.DevcontainerCLIUpOptions
-			wantArgs  string
-			wantError bool
+			name            string
+			logFile         string
+			workspace       string
+			config          string
+			opts            []agentcontainers.DevcontainerCLIUpOptions
+			wantArgs        string
+			wantError       bool
+			wantContainerID bool // If true, expect a container ID even when wantError is true.
 		}{
 			{
-				name:      "success",
-				logFile:   "up.log",
-				workspace: "/test/workspace",
-				wantArgs:  "up --log-format json --workspace-folder /test/workspace",
-				wantError: false,
+				name:            "success",
+				logFile:         "up.log",
+				workspace:       "/test/workspace",
+				wantArgs:        "up --log-format json --workspace-folder /test/workspace",
+				wantError:       false,
+				wantContainerID: true,
 			},
 			{
-				name:      "success with config",
-				logFile:   "up.log",
-				workspace: "/test/workspace",
-				config:    "/test/config.json",
-				wantArgs:  "up --log-format json --workspace-folder /test/workspace --config /test/config.json",
-				wantError: false,
+				name:            "success with config",
+				logFile:         "up.log",
+				workspace:       "/test/workspace",
+				config:          "/test/config.json",
+				wantArgs:        "up --log-format json --workspace-folder /test/workspace --config /test/config.json",
+				wantError:       false,
+				wantContainerID: true,
 			},
 			{
-				name:      "already exists",
-				logFile:   "up-already-exists.log",
-				workspace: "/test/workspace",
-				wantArgs:  "up --log-format json --workspace-folder /test/workspace",
-				wantError: false,
+				name:            "already exists",
+				logFile:         "up-already-exists.log",
+				workspace:       "/test/workspace",
+				wantArgs:        "up --log-format json --workspace-folder /test/workspace",
+				wantError:       false,
+				wantContainerID: true,
 			},
 			{
-				name:      "docker error",
-				logFile:   "up-error-docker.log",
-				workspace: "/test/workspace",
-				wantArgs:  "up --log-format json --workspace-folder /test/workspace",
-				wantError: true,
+				name:            "docker error",
+				logFile:         "up-error-docker.log",
+				workspace:       "/test/workspace",
+				wantArgs:        "up --log-format json --workspace-folder /test/workspace",
+				wantError:       true,
+				wantContainerID: false,
 			},
 			{
-				name:      "bad outcome",
-				logFile:   "up-error-bad-outcome.log",
-				workspace: "/test/workspace",
-				wantArgs:  "up --log-format json --workspace-folder /test/workspace",
-				wantError: true,
+				name:            "bad outcome",
+				logFile:         "up-error-bad-outcome.log",
+				workspace:       "/test/workspace",
+				wantArgs:        "up --log-format json --workspace-folder /test/workspace",
+				wantError:       true,
+				wantContainerID: false,
 			},
 			{
-				name:      "does not exist",
-				logFile:   "up-error-does-not-exist.log",
-				workspace: "/test/workspace",
-				wantArgs:  "up --log-format json --workspace-folder /test/workspace",
-				wantError: true,
+				name:            "does not exist",
+				logFile:         "up-error-does-not-exist.log",
+				workspace:       "/test/workspace",
+				wantArgs:        "up --log-format json --workspace-folder /test/workspace",
+				wantError:       true,
+				wantContainerID: false,
 			},
 			{
 				name:      "with remove existing container",
@@ -100,8 +107,21 @@ func TestDevcontainerCLI_ArgsAndParsing(t *testing.T) {
 				opts: []agentcontainers.DevcontainerCLIUpOptions{
 					agentcontainers.WithRemoveExistingContainer(),
 				},
-				wantArgs:  "up --log-format json --workspace-folder /test/workspace --remove-existing-container",
-				wantError: false,
+				wantArgs:        "up --log-format json --workspace-folder /test/workspace --remove-existing-container",
+				wantError:       false,
+				wantContainerID: true,
+			},
+			{
+				// This test verifies that when a lifecycle script like
+				// postCreateCommand fails, the CLI returns both an error
+				// and a container ID. The caller can then proceed with
+				// agent injection into the created container.
+				name:            "lifecycle script failure with container",
+				logFile:         "up-error-lifecycle-script.log",
+				workspace:       "/test/workspace",
+				wantArgs:        "up --log-format json --workspace-folder /test/workspace",
+				wantError:       true,
+				wantContainerID: true,
 			},
 		}

@@ -122,10 +142,13 @@ func TestDevcontainerCLI_ArgsAndParsing(t *testing.T) {
 				containerID, err := dccli.Up(ctx, tt.workspace, tt.config, tt.opts...)
 				if tt.wantError {
 					assert.Error(t, err, "want error")
-					assert.Empty(t, containerID, "expected empty container ID")
 				} else {
 					assert.NoError(t, err, "want no error")
+				}
+				if tt.wantContainerID {
 					assert.NotEmpty(t, containerID, "expected non-empty container ID")
+				} else {
+					assert.Empty(t, containerID, "expected empty container ID")
 				}
 			})
 		}
@@ -0,0 +1,146 @@
+package agentsocket
+
+import (
+	"context"
+
+	"golang.org/x/xerrors"
+	"storj.io/drpc"
+	"storj.io/drpc/drpcconn"
+
+	"github.com/coder/coder/v2/agent/agentsocket/proto"
+	"github.com/coder/coder/v2/agent/unit"
+)
+
+// Option represents a configuration option for NewClient.
+type Option func(*options)
+
+type options struct {
+	path string
+}
+
+// WithPath sets the socket path. If not provided or empty, the client will
+// auto-discover the default socket path.
+func WithPath(path string) Option {
+	return func(opts *options) {
+		if path == "" {
+			return
+		}
+		opts.path = path
+	}
+}
+
+// Client provides a client for communicating with the workspace agentsocket API.
+type Client struct {
+	client proto.DRPCAgentSocketClient
+	conn   drpc.Conn
+}
+
+// NewClient creates a new socket client and opens a connection to the socket.
+// If path is not provided via WithPath or is empty, it will auto-discover the
+// default socket path.
+func NewClient(ctx context.Context, opts ...Option) (*Client, error) {
+	options := &options{}
+	for _, opt := range opts {
+		opt(options)
+	}
+
+	conn, err := dialSocket(ctx, options.path)
+	if err != nil {
+		return nil, xerrors.Errorf("connect to socket: %w", err)
+	}
+
+	drpcConn := drpcconn.New(conn)
+	client := proto.NewDRPCAgentSocketClient(drpcConn)
+
+	return &Client{
+		client: client,
+		conn:   drpcConn,
+	}, nil
+}
+
+// Close closes the socket connection.
+func (c *Client) Close() error {
+	return c.conn.Close()
+}
+
+// Ping sends a ping request to the agent.
+func (c *Client) Ping(ctx context.Context) error {
+	_, err := c.client.Ping(ctx, &proto.PingRequest{})
+	return err
+}
+
+// SyncStart starts a unit in the dependency graph.
+func (c *Client) SyncStart(ctx context.Context, unitName unit.ID) error {
+	_, err := c.client.SyncStart(ctx, &proto.SyncStartRequest{
+		Unit: string(unitName),
+	})
+	return err
+}
+
+// SyncWant declares a dependency between units.
+func (c *Client) SyncWant(ctx context.Context, unitName, dependsOn unit.ID) error {
+	_, err := c.client.SyncWant(ctx, &proto.SyncWantRequest{
+		Unit:      string(unitName),
+		DependsOn: string(dependsOn),
+	})
+	return err
+}
+
+// SyncComplete marks a unit as complete in the dependency graph.
+func (c *Client) SyncComplete(ctx context.Context, unitName unit.ID) error {
+	_, err := c.client.SyncComplete(ctx, &proto.SyncCompleteRequest{
+		Unit: string(unitName),
+	})
+	return err
+}
+
+// SyncReady requests whether a unit is ready to be started. That is, all dependencies are satisfied.
+func (c *Client) SyncReady(ctx context.Context, unitName unit.ID) (bool, error) {
+	resp, err := c.client.SyncReady(ctx, &proto.SyncReadyRequest{
+		Unit: string(unitName),
+	})
+	return resp.Ready, err
+}
+
+// SyncStatus gets the status of a unit and its dependencies.
+func (c *Client) SyncStatus(ctx context.Context, unitName unit.ID) (SyncStatusResponse, error) {
+	resp, err := c.client.SyncStatus(ctx, &proto.SyncStatusRequest{
+		Unit: string(unitName),
+	})
+	if err != nil {
+		return SyncStatusResponse{}, err
+	}
+
+	var dependencies []DependencyInfo
+	for _, dep := range resp.Dependencies {
+		dependencies = append(dependencies, DependencyInfo{
+			DependsOn:      unit.ID(dep.DependsOn),
+			RequiredStatus: unit.Status(dep.RequiredStatus),
+			CurrentStatus:  unit.Status(dep.CurrentStatus),
+			IsSatisfied:    dep.IsSatisfied,
+		})
+	}
+
+	return SyncStatusResponse{
+		UnitName:     unitName,
+		Status:       unit.Status(resp.Status),
+		IsReady:      resp.IsReady,
+		Dependencies: dependencies,
+	}, nil
+}
+
+// SyncStatusResponse contains the status information for a unit.
+type SyncStatusResponse struct {
+	UnitName     unit.ID          `table:"unit,default_sort" json:"unit_name"`
+	Status       unit.Status      `table:"status" json:"status"`
+	IsReady      bool             `table:"ready" json:"is_ready"`
+	Dependencies []DependencyInfo `table:"dependencies" json:"dependencies"`
+}
+
+// DependencyInfo contains information about a unit dependency.
+type DependencyInfo struct {
+	DependsOn      unit.ID     `table:"depends on,default_sort" json:"depends_on"`
+	RequiredStatus unit.Status `table:"required status" json:"required_status"`
+	CurrentStatus  unit.Status `table:"current status" json:"current_status"`
+	IsSatisfied    bool        `table:"satisfied" json:"is_satisfied"`
+}
@@ -9,7 +9,6 @@ package proto
 import (
 	protoreflect "google.golang.org/protobuf/reflect/protoreflect"
 	protoimpl "google.golang.org/protobuf/runtime/protoimpl"
-	timestamppb "google.golang.org/protobuf/types/known/timestamppb"
 	reflect "reflect"
 	sync "sync"
 )
@@ -63,9 +62,6 @@ type PingResponse struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields
-
-	Message   string                 `protobuf:"bytes,1,opt,name=message,proto3" json:"message,omitempty"`
-	Timestamp *timestamppb.Timestamp `protobuf:"bytes,2,opt,name=timestamp,proto3" json:"timestamp,omitempty"`
 }

 func (x *PingResponse) Reset() {
@@ -100,20 +96,6 @@ func (*PingResponse) Descriptor() ([]byte, []int) {
 	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{1}
 }

-func (x *PingResponse) GetMessage() string {
-	if x != nil {
-		return x.Message
-	}
-	return ""
-}
-
-func (x *PingResponse) GetTimestamp() *timestamppb.Timestamp {
-	if x != nil {
-		return x.Timestamp
-	}
-	return nil
-}
-
 type SyncStartRequest struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
@@ -165,9 +147,6 @@ type SyncStartResponse struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields
-
-	Success bool   `protobuf:"varint,1,opt,name=success,proto3" json:"success,omitempty"`
-	Message string `protobuf:"bytes,2,opt,name=message,proto3" json:"message,omitempty"`
 }

 func (x *SyncStartResponse) Reset() {
@@ -202,20 +181,6 @@ func (*SyncStartResponse) Descriptor() ([]byte, []int) {
 	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{3}
 }

-func (x *SyncStartResponse) GetSuccess() bool {
-	if x != nil {
-		return x.Success
-	}
-	return false
-}
-
-func (x *SyncStartResponse) GetMessage() string {
-	if x != nil {
-		return x.Message
-	}
-	return ""
-}
-
 type SyncWantRequest struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
@@ -275,9 +240,6 @@ type SyncWantResponse struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields
-
-	Success bool   `protobuf:"varint,1,opt,name=success,proto3" json:"success,omitempty"`
-	Message string `protobuf:"bytes,2,opt,name=message,proto3" json:"message,omitempty"`
 }

 func (x *SyncWantResponse) Reset() {
@@ -312,20 +274,6 @@ func (*SyncWantResponse) Descriptor() ([]byte, []int) {
 	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{5}
 }

-func (x *SyncWantResponse) GetSuccess() bool {
-	if x != nil {
-		return x.Success
-	}
-	return false
-}
-
-func (x *SyncWantResponse) GetMessage() string {
-	if x != nil {
-		return x.Message
-	}
-	return ""
-}
-
 type SyncCompleteRequest struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
@@ -377,9 +325,6 @@ type SyncCompleteResponse struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields
-
-	Success bool   `protobuf:"varint,1,opt,name=success,proto3" json:"success,omitempty"`
-	Message string `protobuf:"bytes,2,opt,name=message,proto3" json:"message,omitempty"`
 }

 func (x *SyncCompleteResponse) Reset() {
@@ -414,20 +359,6 @@ func (*SyncCompleteResponse) Descriptor() ([]byte, []int) {
 	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{7}
 }

-func (x *SyncCompleteResponse) GetSuccess() bool {
-	if x != nil {
-		return x.Success
-	}
-	return false
-}
-
-func (x *SyncCompleteResponse) GetMessage() string {
-	if x != nil {
-		return x.Message
-	}
-	return ""
-}
-
 type SyncReadyRequest struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
@@ -480,8 +411,7 @@ type SyncReadyResponse struct {
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields

-	Success bool   `protobuf:"varint,1,opt,name=success,proto3" json:"success,omitempty"`
-	Message string `protobuf:"bytes,2,opt,name=message,proto3" json:"message,omitempty"`
+	Ready bool `protobuf:"varint,1,opt,name=ready,proto3" json:"ready,omitempty"`
 }

 func (x *SyncReadyResponse) Reset() {
@@ -516,27 +446,19 @@ func (*SyncReadyResponse) Descriptor() ([]byte, []int) {
 	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{9}
 }

-func (x *SyncReadyResponse) GetSuccess() bool {
+func (x *SyncReadyResponse) GetReady() bool {
 	if x != nil {
-		return x.Success
+		return x.Ready
 	}
 	return false
 }

-func (x *SyncReadyResponse) GetMessage() string {
-	if x != nil {
-		return x.Message
-	}
-	return ""
-}
-
 type SyncStatusRequest struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields

-	Unit      string `protobuf:"bytes,1,opt,name=unit,proto3" json:"unit,omitempty"`
-	Recursive bool   `protobuf:"varint,2,opt,name=recursive,proto3" json:"recursive,omitempty"`
+	Unit string `protobuf:"bytes,1,opt,name=unit,proto3" json:"unit,omitempty"`
 }

 func (x *SyncStatusRequest) Reset() {
@@ -578,22 +500,16 @@ func (x *SyncStatusRequest) GetUnit() string {
 	return ""
 }

-func (x *SyncStatusRequest) GetRecursive() bool {
-	if x != nil {
-		return x.Recursive
-	}
-	return false
-}
-
 type DependencyInfo struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields

-	DependsOn      string `protobuf:"bytes,1,opt,name=depends_on,json=dependsOn,proto3" json:"depends_on,omitempty"`
-	RequiredStatus string `protobuf:"bytes,2,opt,name=required_status,json=requiredStatus,proto3" json:"required_status,omitempty"`
-	CurrentStatus  string `protobuf:"bytes,3,opt,name=current_status,json=currentStatus,proto3" json:"current_status,omitempty"`
-	IsSatisfied    bool   `protobuf:"varint,4,opt,name=is_satisfied,json=isSatisfied,proto3" json:"is_satisfied,omitempty"`
+	Unit           string `protobuf:"bytes,1,opt,name=unit,proto3" json:"unit,omitempty"`
+	DependsOn      string `protobuf:"bytes,2,opt,name=depends_on,json=dependsOn,proto3" json:"depends_on,omitempty"`
+	RequiredStatus string `protobuf:"bytes,3,opt,name=required_status,json=requiredStatus,proto3" json:"required_status,omitempty"`
+	CurrentStatus  string `protobuf:"bytes,4,opt,name=current_status,json=currentStatus,proto3" json:"current_status,omitempty"`
+	IsSatisfied    bool   `protobuf:"varint,5,opt,name=is_satisfied,json=isSatisfied,proto3" json:"is_satisfied,omitempty"`
 }

 func (x *DependencyInfo) Reset() {
@@ -628,6 +544,13 @@ func (*DependencyInfo) Descriptor() ([]byte, []int) {
 	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{11}
 }

+func (x *DependencyInfo) GetUnit() string {
+	if x != nil {
+		return x.Unit
+	}
+	return ""
+}
+
 func (x *DependencyInfo) GetDependsOn() string {
 	if x != nil {
 		return x.DependsOn
@@ -661,13 +584,9 @@ type SyncStatusResponse struct {
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields

-	Success      bool              `protobuf:"varint,1,opt,name=success,proto3" json:"success,omitempty"`
-	Message      string            `protobuf:"bytes,2,opt,name=message,proto3" json:"message,omitempty"`
-	Unit         string            `protobuf:"bytes,3,opt,name=unit,proto3" json:"unit,omitempty"`
-	Status       string            `protobuf:"bytes,4,opt,name=status,proto3" json:"status,omitempty"`
-	IsReady      bool              `protobuf:"varint,5,opt,name=is_ready,json=isReady,proto3" json:"is_ready,omitempty"`
-	Dependencies []*DependencyInfo `protobuf:"bytes,6,rep,name=dependencies,proto3" json:"dependencies,omitempty"`
-	Dot          string            `protobuf:"bytes,7,opt,name=dot,proto3" json:"dot,omitempty"`
+	Status       string            `protobuf:"bytes,1,opt,name=status,proto3" json:"status,omitempty"`
+	IsReady      bool              `protobuf:"varint,2,opt,name=is_ready,json=isReady,proto3" json:"is_ready,omitempty"`
+	Dependencies []*DependencyInfo `protobuf:"bytes,3,rep,name=dependencies,proto3" json:"dependencies,omitempty"`
 }

 func (x *SyncStatusResponse) Reset() {
@@ -702,27 +621,6 @@ func (*SyncStatusResponse) Descriptor() ([]byte, []int) {
 	return file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP(), []int{12}
 }

-func (x *SyncStatusResponse) GetSuccess() bool {
-	if x != nil {
-		return x.Success
-	}
-	return false
-}
-
-func (x *SyncStatusResponse) GetMessage() string {
-	if x != nil {
-		return x.Message
-	}
-	return ""
-}
-
-func (x *SyncStatusResponse) GetUnit() string {
-	if x != nil {
-		return x.Unit
-	}
-	return ""
-}
-
 func (x *SyncStatusResponse) GetStatus() string {
 	if x != nil {
 		return x.Status
@@ -744,13 +642,6 @@ func (x *SyncStatusResponse) GetDependencies() []*DependencyInfo {
 	return nil
 }

-func (x *SyncStatusResponse) GetDot() string {
-	if x != nil {
-		return x.Dot
-	}
-	return ""
-}
-
 var File_agent_agentsocket_proto_agentsocket_proto protoreflect.FileDescriptor

 var file_agent_agentsocket_proto_agentsocket_proto_rawDesc = []byte{
@@ -758,116 +649,90 @@ var file_agent_agentsocket_proto_agentsocket_proto_rawDesc = []byte{
 	0x6b, 0x65, 0x74, 0x2f, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x2f, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73,
 	0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x12, 0x14, 0x63, 0x6f, 0x64,
 	0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e, 0x76,
-	0x31, 0x1a, 0x1f, 0x67, 0x6f, 0x6f, 0x67, 0x6c, 0x65, 0x2f, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x62,
-	0x75, 0x66, 0x2f, 0x74, 0x69, 0x6d, 0x65, 0x73, 0x74, 0x61, 0x6d, 0x70, 0x2e, 0x70, 0x72, 0x6f,
-	0x74, 0x6f, 0x22, 0x0d, 0x0a, 0x0b, 0x50, 0x69, 0x6e, 0x67, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73,
-	0x74, 0x22, 0x62, 0x0a, 0x0c, 0x50, 0x69, 0x6e, 0x67, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73,
-	0x65, 0x12, 0x18, 0x0a, 0x07, 0x6d, 0x65, 0x73, 0x73, 0x61, 0x67, 0x65, 0x18, 0x01, 0x20, 0x01,
-	0x28, 0x09, 0x52, 0x07, 0x6d, 0x65, 0x73, 0x73, 0x61, 0x67, 0x65, 0x12, 0x38, 0x0a, 0x09, 0x74,
-	0x69, 0x6d, 0x65, 0x73, 0x74, 0x61, 0x6d, 0x70, 0x18, 0x02, 0x20, 0x01, 0x28, 0x0b, 0x32, 0x1a,
-	0x2e, 0x67, 0x6f, 0x6f, 0x67, 0x6c, 0x65, 0x2e, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x62, 0x75, 0x66,
-	0x2e, 0x54, 0x69, 0x6d, 0x65, 0x73, 0x74, 0x61, 0x6d, 0x70, 0x52, 0x09, 0x74, 0x69, 0x6d, 0x65,
-	0x73, 0x74, 0x61, 0x6d, 0x70, 0x22, 0x26, 0x0a, 0x10, 0x53, 0x79, 0x6e, 0x63, 0x53, 0x74, 0x61,
-	0x72, 0x74, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x12, 0x12, 0x0a, 0x04, 0x75, 0x6e, 0x69,
-	0x74, 0x18, 0x01, 0x20, 0x01, 0x28, 0x09, 0x52, 0x04, 0x75, 0x6e, 0x69, 0x74, 0x22, 0x47, 0x0a,
-	0x11, 0x53, 0x79, 0x6e, 0x63, 0x53, 0x74, 0x61, 0x72, 0x74, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e,
-	0x73, 0x65, 0x12, 0x18, 0x0a, 0x07, 0x73, 0x75, 0x63, 0x63, 0x65, 0x73, 0x73, 0x18, 0x01, 0x20,
-	0x01, 0x28, 0x08, 0x52, 0x07, 0x73, 0x75, 0x63, 0x63, 0x65, 0x73, 0x73, 0x12, 0x18, 0x0a, 0x07,
-	0x6d, 0x65, 0x73, 0x73, 0x61, 0x67, 0x65, 0x18, 0x02, 0x20, 0x01, 0x28, 0x09, 0x52, 0x07, 0x6d,
-	0x65, 0x73, 0x73, 0x61, 0x67, 0x65, 0x22, 0x44, 0x0a, 0x0f, 0x53, 0x79, 0x6e, 0x63, 0x57, 0x61,
-	0x6e, 0x74, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x12, 0x12, 0x0a, 0x04, 0x75, 0x6e, 0x69,
+	0x31, 0x22, 0x0d, 0x0a, 0x0b, 0x50, 0x69, 0x6e, 0x67, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74,
+	0x22, 0x0e, 0x0a, 0x0c, 0x50, 0x69, 0x6e, 0x67, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65,
+	0x22, 0x26, 0x0a, 0x10, 0x53, 0x79, 0x6e, 0x63, 0x53, 0x74, 0x61, 0x72, 0x74, 0x52, 0x65, 0x71,
+	0x75, 0x65, 0x73, 0x74, 0x12, 0x12, 0x0a, 0x04, 0x75, 0x6e, 0x69, 0x74, 0x18, 0x01, 0x20, 0x01,
+	0x28, 0x09, 0x52, 0x04, 0x75, 0x6e, 0x69, 0x74, 0x22, 0x13, 0x0a, 0x11, 0x53, 0x79, 0x6e, 0x63,
+	0x53, 0x74, 0x61, 0x72, 0x74, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x22, 0x44, 0x0a,
+	0x0f, 0x53, 0x79, 0x6e, 0x63, 0x57, 0x61, 0x6e, 0x74, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74,
+	0x12, 0x12, 0x0a, 0x04, 0x75, 0x6e, 0x69, 0x74, 0x18, 0x01, 0x20, 0x01, 0x28, 0x09, 0x52, 0x04,
+	0x75, 0x6e, 0x69, 0x74, 0x12, 0x1d, 0x0a, 0x0a, 0x64, 0x65, 0x70, 0x65, 0x6e, 0x64, 0x73, 0x5f,
+	0x6f, 0x6e, 0x18, 0x02, 0x20, 0x01, 0x28, 0x09, 0x52, 0x09, 0x64, 0x65, 0x70, 0x65, 0x6e, 0x64,
+	0x73, 0x4f, 0x6e, 0x22, 0x12, 0x0a, 0x10, 0x53, 0x79, 0x6e, 0x63, 0x57, 0x61, 0x6e, 0x74, 0x52,
+	0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x22, 0x29, 0x0a, 0x13, 0x53, 0x79, 0x6e, 0x63, 0x43,
+	0x6f, 0x6d, 0x70, 0x6c, 0x65, 0x74, 0x65, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x12, 0x12,
+	0x0a, 0x04, 0x75, 0x6e, 0x69, 0x74, 0x18, 0x01, 0x20, 0x01, 0x28, 0x09, 0x52, 0x04, 0x75, 0x6e,
+	0x69, 0x74, 0x22, 0x16, 0x0a, 0x14, 0x53, 0x79, 0x6e, 0x63, 0x43, 0x6f, 0x6d, 0x70, 0x6c, 0x65,
+	0x74, 0x65, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x22, 0x26, 0x0a, 0x10, 0x53, 0x79,
+	0x6e, 0x63, 0x52, 0x65, 0x61, 0x64, 0x79, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x12, 0x12,
+	0x0a, 0x04, 0x75, 0x6e, 0x69, 0x74, 0x18, 0x01, 0x20, 0x01, 0x28, 0x09, 0x52, 0x04, 0x75, 0x6e,
+	0x69, 0x74, 0x22, 0x29, 0x0a, 0x11, 0x53, 0x79, 0x6e, 0x63, 0x52, 0x65, 0x61, 0x64, 0x79, 0x52,
+	0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x12, 0x14, 0x0a, 0x05, 0x72, 0x65, 0x61, 0x64, 0x79,
+	0x18, 0x01, 0x20, 0x01, 0x28, 0x08, 0x52, 0x05, 0x72, 0x65, 0x61, 0x64, 0x79, 0x22, 0x27, 0x0a,
+	0x11, 0x53, 0x79, 0x6e, 0x63, 0x53, 0x74, 0x61, 0x74, 0x75, 0x73, 0x52, 0x65, 0x71, 0x75, 0x65,
+	0x73, 0x74, 0x12, 0x12, 0x0a, 0x04, 0x75, 0x6e, 0x69, 0x74, 0x18, 0x01, 0x20, 0x01, 0x28, 0x09,
+	0x52, 0x04, 0x75, 0x6e, 0x69, 0x74, 0x22, 0xb6, 0x01, 0x0a, 0x0e, 0x44, 0x65, 0x70, 0x65, 0x6e,
+	0x64, 0x65, 0x6e, 0x63, 0x79, 0x49, 0x6e, 0x66, 0x6f, 0x12, 0x12, 0x0a, 0x04, 0x75, 0x6e, 0x69,
 	0x74, 0x18, 0x01, 0x20, 0x01, 0x28, 0x09, 0x52, 0x04, 0x75, 0x6e, 0x69, 0x74, 0x12, 0x1d, 0x0a,
 	0x0a, 0x64, 0x65, 0x70, 0x65, 0x6e, 0x64, 0x73, 0x5f, 0x6f, 0x6e, 0x18, 0x02, 0x20, 0x01, 0x28,
-	0x09, 0x52, 0x09, 0x64, 0x65, 0x70, 0x65, 0x6e, 0x64, 0x73, 0x4f, 0x6e, 0x22, 0x46, 0x0a, 0x10,
-	0x53, 0x79, 0x6e, 0x63, 0x57, 0x61, 0x6e, 0x74, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65,
-	0x12, 0x18, 0x0a, 0x07, 0x73, 0x75, 0x63, 0x63, 0x65, 0x73, 0x73, 0x18, 0x01, 0x20, 0x01, 0x28,
-	0x08, 0x52, 0x07, 0x73, 0x75, 0x63, 0x63, 0x65, 0x73, 0x73, 0x12, 0x18, 0x0a, 0x07, 0x6d, 0x65,
-	0x73, 0x73, 0x61, 0x67, 0x65, 0x18, 0x02, 0x20, 0x01, 0x28, 0x09, 0x52, 0x07, 0x6d, 0x65, 0x73,
-	0x73, 0x61, 0x67, 0x65, 0x22, 0x29, 0x0a, 0x13, 0x53, 0x79, 0x6e, 0x63, 0x43, 0x6f, 0x6d, 0x70,
-	0x6c, 0x65, 0x74, 0x65, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x12, 0x12, 0x0a, 0x04, 0x75,
-	0x6e, 0x69, 0x74, 0x18, 0x01, 0x20, 0x01, 0x28, 0x09, 0x52, 0x04, 0x75, 0x6e, 0x69, 0x74, 0x22,
-	0x4a, 0x0a, 0x14, 0x53, 0x79, 0x6e, 0x63, 0x43, 0x6f, 0x6d, 0x70, 0x6c, 0x65, 0x74, 0x65, 0x52,
-	0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x12, 0x18, 0x0a, 0x07, 0x73, 0x75, 0x63, 0x63, 0x65,
-	0x73, 0x73, 0x18, 0x01, 0x20, 0x01, 0x28, 0x08, 0x52, 0x07, 0x73, 0x75, 0x63, 0x63, 0x65, 0x73,
-	0x73, 0x12, 0x18, 0x0a, 0x07, 0x6d, 0x65, 0x73, 0x73, 0x61, 0x67, 0x65, 0x18, 0x02, 0x20, 0x01,
-	0x28, 0x09, 0x52, 0x07, 0x6d, 0x65, 0x73, 0x73, 0x61, 0x67, 0x65, 0x22, 0x26, 0x0a, 0x10, 0x53,
-	0x79, 0x6e, 0x63, 0x52, 0x65, 0x61, 0x64, 0x79, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x12,
-	0x12, 0x0a, 0x04, 0x75, 0x6e, 0x69, 0x74, 0x18, 0x01, 0x20, 0x01, 0x28, 0x09, 0x52, 0x04, 0x75,
-	0x6e, 0x69, 0x74, 0x22, 0x47, 0x0a, 0x11, 0x53, 0x79, 0x6e, 0x63, 0x52, 0x65, 0x61, 0x64, 0x79,
-	0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x12, 0x18, 0x0a, 0x07, 0x73, 0x75, 0x63, 0x63,
-	0x65, 0x73, 0x73, 0x18, 0x01, 0x20, 0x01, 0x28, 0x08, 0x52, 0x07, 0x73, 0x75, 0x63, 0x63, 0x65,
-	0x73, 0x73, 0x12, 0x18, 0x0a, 0x07, 0x6d, 0x65, 0x73, 0x73, 0x61, 0x67, 0x65, 0x18, 0x02, 0x20,
-	0x01, 0x28, 0x09, 0x52, 0x07, 0x6d, 0x65, 0x73, 0x73, 0x61, 0x67, 0x65, 0x22, 0x45, 0x0a, 0x11,
-	0x53, 0x79, 0x6e, 0x63, 0x53, 0x74, 0x61, 0x74, 0x75, 0x73, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73,
-	0x74, 0x12, 0x12, 0x0a, 0x04, 0x75, 0x6e, 0x69, 0x74, 0x18, 0x01, 0x20, 0x01, 0x28, 0x09, 0x52,
-	0x04, 0x75, 0x6e, 0x69, 0x74, 0x12, 0x1c, 0x0a, 0x09, 0x72, 0x65, 0x63, 0x75, 0x72, 0x73, 0x69,
-	0x76, 0x65, 0x18, 0x02, 0x20, 0x01, 0x28, 0x08, 0x52, 0x09, 0x72, 0x65, 0x63, 0x75, 0x72, 0x73,
-	0x69, 0x76, 0x65, 0x22, 0xa2, 0x01, 0x0a, 0x0e, 0x44, 0x65, 0x70, 0x65, 0x6e, 0x64, 0x65, 0x6e,
-	0x63, 0x79, 0x49, 0x6e, 0x66, 0x6f, 0x12, 0x1d, 0x0a, 0x0a, 0x64, 0x65, 0x70, 0x65, 0x6e, 0x64,
-	0x73, 0x5f, 0x6f, 0x6e, 0x18, 0x01, 0x20, 0x01, 0x28, 0x09, 0x52, 0x09, 0x64, 0x65, 0x70, 0x65,
-	0x6e, 0x64, 0x73, 0x4f, 0x6e, 0x12, 0x27, 0x0a, 0x0f, 0x72, 0x65, 0x71, 0x75, 0x69, 0x72, 0x65,
-	0x64, 0x5f, 0x73, 0x74, 0x61, 0x74, 0x75, 0x73, 0x18, 0x02, 0x20, 0x01, 0x28, 0x09, 0x52, 0x0e,
-	0x72, 0x65, 0x71, 0x75, 0x69, 0x72, 0x65, 0x64, 0x53, 0x74, 0x61, 0x74, 0x75, 0x73, 0x12, 0x25,
-	0x0a, 0x0e, 0x63, 0x75, 0x72, 0x72, 0x65, 0x6e, 0x74, 0x5f, 0x73, 0x74, 0x61, 0x74, 0x75, 0x73,
-	0x18, 0x03, 0x20, 0x01, 0x28, 0x09, 0x52, 0x0d, 0x63, 0x75, 0x72, 0x72, 0x65, 0x6e, 0x74, 0x53,
-	0x74, 0x61, 0x74, 0x75, 0x73, 0x12, 0x21, 0x0a, 0x0c, 0x69, 0x73, 0x5f, 0x73, 0x61, 0x74, 0x69,
-	0x73, 0x66, 0x69, 0x65, 0x64, 0x18, 0x04, 0x20, 0x01, 0x28, 0x08, 0x52, 0x0b, 0x69, 0x73, 0x53,
-	0x61, 0x74, 0x69, 0x73, 0x66, 0x69, 0x65, 0x64, 0x22, 0xeb, 0x01, 0x0a, 0x12, 0x53, 0x79, 0x6e,
-	0x63, 0x53, 0x74, 0x61, 0x74, 0x75, 0x73, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x12,
-	0x18, 0x0a, 0x07, 0x73, 0x75, 0x63, 0x63, 0x65, 0x73, 0x73, 0x18, 0x01, 0x20, 0x01, 0x28, 0x08,
-	0x52, 0x07, 0x73, 0x75, 0x63, 0x63, 0x65, 0x73, 0x73, 0x12, 0x18, 0x0a, 0x07, 0x6d, 0x65, 0x73,
-	0x73, 0x61, 0x67, 0x65, 0x18, 0x02, 0x20, 0x01, 0x28, 0x09, 0x52, 0x07, 0x6d, 0x65, 0x73, 0x73,
-	0x61, 0x67, 0x65, 0x12, 0x12, 0x0a, 0x04, 0x75, 0x6e, 0x69, 0x74, 0x18, 0x03, 0x20, 0x01, 0x28,
-	0x09, 0x52, 0x04, 0x75, 0x6e, 0x69, 0x74, 0x12, 0x16, 0x0a, 0x06, 0x73, 0x74, 0x61, 0x74, 0x75,
-	0x73, 0x18, 0x04, 0x20, 0x01, 0x28, 0x09, 0x52, 0x06, 0x73, 0x74, 0x61, 0x74, 0x75, 0x73, 0x12,
-	0x19, 0x0a, 0x08, 0x69, 0x73, 0x5f, 0x72, 0x65, 0x61, 0x64, 0x79, 0x18, 0x05, 0x20, 0x01, 0x28,
-	0x08, 0x52, 0x07, 0x69, 0x73, 0x52, 0x65, 0x61, 0x64, 0x79, 0x12, 0x48, 0x0a, 0x0c, 0x64, 0x65,
-	0x70, 0x65, 0x6e, 0x64, 0x65, 0x6e, 0x63, 0x69, 0x65, 0x73, 0x18, 0x06, 0x20, 0x03, 0x28, 0x0b,
-	0x32, 0x24, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f,
-	0x63, 0x6b, 0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x44, 0x65, 0x70, 0x65, 0x6e, 0x64, 0x65, 0x6e,
-	0x63, 0x79, 0x49, 0x6e, 0x66, 0x6f, 0x52, 0x0c, 0x64, 0x65, 0x70, 0x65, 0x6e, 0x64, 0x65, 0x6e,
-	0x63, 0x69, 0x65, 0x73, 0x12, 0x10, 0x0a, 0x03, 0x64, 0x6f, 0x74, 0x18, 0x07, 0x20, 0x01, 0x28,
-	0x09, 0x52, 0x03, 0x64, 0x6f, 0x74, 0x32, 0xbb, 0x04, 0x0a, 0x0b, 0x41, 0x67, 0x65, 0x6e, 0x74,
-	0x53, 0x6f, 0x63, 0x6b, 0x65, 0x74, 0x12, 0x4d, 0x0a, 0x04, 0x50, 0x69, 0x6e, 0x67, 0x12, 0x21,
+	0x09, 0x52, 0x09, 0x64, 0x65, 0x70, 0x65, 0x6e, 0x64, 0x73, 0x4f, 0x6e, 0x12, 0x27, 0x0a, 0x0f,
+	0x72, 0x65, 0x71, 0x75, 0x69, 0x72, 0x65, 0x64, 0x5f, 0x73, 0x74, 0x61, 0x74, 0x75, 0x73, 0x18,
+	0x03, 0x20, 0x01, 0x28, 0x09, 0x52, 0x0e, 0x72, 0x65, 0x71, 0x75, 0x69, 0x72, 0x65, 0x64, 0x53,
+	0x74, 0x61, 0x74, 0x75, 0x73, 0x12, 0x25, 0x0a, 0x0e, 0x63, 0x75, 0x72, 0x72, 0x65, 0x6e, 0x74,
+	0x5f, 0x73, 0x74, 0x61, 0x74, 0x75, 0x73, 0x18, 0x04, 0x20, 0x01, 0x28, 0x09, 0x52, 0x0d, 0x63,
+	0x75, 0x72, 0x72, 0x65, 0x6e, 0x74, 0x53, 0x74, 0x61, 0x74, 0x75, 0x73, 0x12, 0x21, 0x0a, 0x0c,
+	0x69, 0x73, 0x5f, 0x73, 0x61, 0x74, 0x69, 0x73, 0x66, 0x69, 0x65, 0x64, 0x18, 0x05, 0x20, 0x01,
+	0x28, 0x08, 0x52, 0x0b, 0x69, 0x73, 0x53, 0x61, 0x74, 0x69, 0x73, 0x66, 0x69, 0x65, 0x64, 0x22,
+	0x91, 0x01, 0x0a, 0x12, 0x53, 0x79, 0x6e, 0x63, 0x53, 0x74, 0x61, 0x74, 0x75, 0x73, 0x52, 0x65,
+	0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x12, 0x16, 0x0a, 0x06, 0x73, 0x74, 0x61, 0x74, 0x75, 0x73,
+	0x18, 0x01, 0x20, 0x01, 0x28, 0x09, 0x52, 0x06, 0x73, 0x74, 0x61, 0x74, 0x75, 0x73, 0x12, 0x19,
+	0x0a, 0x08, 0x69, 0x73, 0x5f, 0x72, 0x65, 0x61, 0x64, 0x79, 0x18, 0x02, 0x20, 0x01, 0x28, 0x08,
+	0x52, 0x07, 0x69, 0x73, 0x52, 0x65, 0x61, 0x64, 0x79, 0x12, 0x48, 0x0a, 0x0c, 0x64, 0x65, 0x70,
+	0x65, 0x6e, 0x64, 0x65, 0x6e, 0x63, 0x69, 0x65, 0x73, 0x18, 0x03, 0x20, 0x03, 0x28, 0x0b, 0x32,
+	0x24, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63,
+	0x6b, 0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x44, 0x65, 0x70, 0x65, 0x6e, 0x64, 0x65, 0x6e, 0x63,
+	0x79, 0x49, 0x6e, 0x66, 0x6f, 0x52, 0x0c, 0x64, 0x65, 0x70, 0x65, 0x6e, 0x64, 0x65, 0x6e, 0x63,
+	0x69, 0x65, 0x73, 0x32, 0xbb, 0x04, 0x0a, 0x0b, 0x41, 0x67, 0x65, 0x6e, 0x74, 0x53, 0x6f, 0x63,
+	0x6b, 0x65, 0x74, 0x12, 0x4d, 0x0a, 0x04, 0x50, 0x69, 0x6e, 0x67, 0x12, 0x21, 0x2e, 0x63, 0x6f,
+	0x64, 0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e,
+	0x76, 0x31, 0x2e, 0x50, 0x69, 0x6e, 0x67, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x1a, 0x22,
 	0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63, 0x6b,
-	0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x50, 0x69, 0x6e, 0x67, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73,
-	0x74, 0x1a, 0x22, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73,
-	0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x50, 0x69, 0x6e, 0x67, 0x52, 0x65, 0x73,
-	0x70, 0x6f, 0x6e, 0x73, 0x65, 0x12, 0x5c, 0x0a, 0x09, 0x53, 0x79, 0x6e, 0x63, 0x53, 0x74, 0x61,
-	0x72, 0x74, 0x12, 0x26, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74,
-	0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x53, 0x79, 0x6e, 0x63, 0x53, 0x74,
-	0x61, 0x72, 0x74, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x1a, 0x27, 0x2e, 0x63, 0x6f, 0x64,
-	0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e, 0x76,
-	0x31, 0x2e, 0x53, 0x79, 0x6e, 0x63, 0x53, 0x74, 0x61, 0x72, 0x74, 0x52, 0x65, 0x73, 0x70, 0x6f,
-	0x6e, 0x73, 0x65, 0x12, 0x59, 0x0a, 0x08, 0x53, 0x79, 0x6e, 0x63, 0x57, 0x61, 0x6e, 0x74, 0x12,
-	0x25, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63,
-	0x6b, 0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x53, 0x79, 0x6e, 0x63, 0x57, 0x61, 0x6e, 0x74, 0x52,
-	0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x1a, 0x26, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61,
+	0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x50, 0x69, 0x6e, 0x67, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e,
+	0x73, 0x65, 0x12, 0x5c, 0x0a, 0x09, 0x53, 0x79, 0x6e, 0x63, 0x53, 0x74, 0x61, 0x72, 0x74, 0x12,
+	0x26, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63,
+	0x6b, 0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x53, 0x79, 0x6e, 0x63, 0x53, 0x74, 0x61, 0x72, 0x74,
+	0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x1a, 0x27, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e,
+	0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x53,
+	0x79, 0x6e, 0x63, 0x53, 0x74, 0x61, 0x72, 0x74, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65,
+	0x12, 0x59, 0x0a, 0x08, 0x53, 0x79, 0x6e, 0x63, 0x57, 0x61, 0x6e, 0x74, 0x12, 0x25, 0x2e, 0x63,
+	0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74,
+	0x2e, 0x76, 0x31, 0x2e, 0x53, 0x79, 0x6e, 0x63, 0x57, 0x61, 0x6e, 0x74, 0x52, 0x65, 0x71, 0x75,
+	0x65, 0x73, 0x74, 0x1a, 0x26, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e,
+	0x74, 0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x53, 0x79, 0x6e, 0x63, 0x57,
+	0x61, 0x6e, 0x74, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x12, 0x65, 0x0a, 0x0c, 0x53,
+	0x79, 0x6e, 0x63, 0x43, 0x6f, 0x6d, 0x70, 0x6c, 0x65, 0x74, 0x65, 0x12, 0x29, 0x2e, 0x63, 0x6f,
+	0x64, 0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e,
+	0x76, 0x31, 0x2e, 0x53, 0x79, 0x6e, 0x63, 0x43, 0x6f, 0x6d, 0x70, 0x6c, 0x65, 0x74, 0x65, 0x52,
+	0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x1a, 0x2a, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61,
 	0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x53, 0x79,
-	0x6e, 0x63, 0x57, 0x61, 0x6e, 0x74, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x12, 0x65,
-	0x0a, 0x0c, 0x53, 0x79, 0x6e, 0x63, 0x43, 0x6f, 0x6d, 0x70, 0x6c, 0x65, 0x74, 0x65, 0x12, 0x29,
+	0x6e, 0x63, 0x43, 0x6f, 0x6d, 0x70, 0x6c, 0x65, 0x74, 0x65, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e,
+	0x73, 0x65, 0x12, 0x5c, 0x0a, 0x09, 0x53, 0x79, 0x6e, 0x63, 0x52, 0x65, 0x61, 0x64, 0x79, 0x12,
+	0x26, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63,
+	0x6b, 0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x53, 0x79, 0x6e, 0x63, 0x52, 0x65, 0x61, 0x64, 0x79,
+	0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x1a, 0x27, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e,
+	0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x53,
+	0x79, 0x6e, 0x63, 0x52, 0x65, 0x61, 0x64, 0x79, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65,
+	0x12, 0x5f, 0x0a, 0x0a, 0x53, 0x79, 0x6e, 0x63, 0x53, 0x74, 0x61, 0x74, 0x75, 0x73, 0x12, 0x27,
 	0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63, 0x6b,
-	0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x53, 0x79, 0x6e, 0x63, 0x43, 0x6f, 0x6d, 0x70, 0x6c, 0x65,
-	0x74, 0x65, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x1a, 0x2a, 0x2e, 0x63, 0x6f, 0x64, 0x65,
-	0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e, 0x76, 0x31,
-	0x2e, 0x53, 0x79, 0x6e, 0x63, 0x43, 0x6f, 0x6d, 0x70, 0x6c, 0x65, 0x74, 0x65, 0x52, 0x65, 0x73,
-	0x70, 0x6f, 0x6e, 0x73, 0x65, 0x12, 0x5c, 0x0a, 0x09, 0x53, 0x79, 0x6e, 0x63, 0x52, 0x65, 0x61,
-	0x64, 0x79, 0x12, 0x26, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74,
-	0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x53, 0x79, 0x6e, 0x63, 0x52, 0x65,
-	0x61, 0x64, 0x79, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x1a, 0x27, 0x2e, 0x63, 0x6f, 0x64,
-	0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e, 0x76,
-	0x31, 0x2e, 0x53, 0x79, 0x6e, 0x63, 0x52, 0x65, 0x61, 0x64, 0x79, 0x52, 0x65, 0x73, 0x70, 0x6f,
-	0x6e, 0x73, 0x65, 0x12, 0x5f, 0x0a, 0x0a, 0x53, 0x79, 0x6e, 0x63, 0x53, 0x74, 0x61, 0x74, 0x75,
-	0x73, 0x12, 0x27, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73,
-	0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x53, 0x79, 0x6e, 0x63, 0x53, 0x74, 0x61,
-	0x74, 0x75, 0x73, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x1a, 0x28, 0x2e, 0x63, 0x6f, 0x64,
-	0x65, 0x72, 0x2e, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e, 0x76,
-	0x31, 0x2e, 0x53, 0x79, 0x6e, 0x63, 0x53, 0x74, 0x61, 0x74, 0x75, 0x73, 0x52, 0x65, 0x73, 0x70,
-	0x6f, 0x6e, 0x73, 0x65, 0x42, 0x33, 0x5a, 0x31, 0x67, 0x69, 0x74, 0x68, 0x75, 0x62, 0x2e, 0x63,
-	0x6f, 0x6d, 0x2f, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2f, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2f, 0x76,
-	0x32, 0x2f, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x2f, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63,
-	0x6b, 0x65, 0x74, 0x2f, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x62, 0x06, 0x70, 0x72, 0x6f, 0x74, 0x6f,
-	0x33,
+	0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x53, 0x79, 0x6e, 0x63, 0x53, 0x74, 0x61, 0x74, 0x75, 0x73,
+	0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x1a, 0x28, 0x2e, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2e,
+	0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74, 0x2e, 0x76, 0x31, 0x2e, 0x53,
+	0x79, 0x6e, 0x63, 0x53, 0x74, 0x61, 0x74, 0x75, 0x73, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73,
+	0x65, 0x42, 0x33, 0x5a, 0x31, 0x67, 0x69, 0x74, 0x68, 0x75, 0x62, 0x2e, 0x63, 0x6f, 0x6d, 0x2f,
+	0x63, 0x6f, 0x64, 0x65, 0x72, 0x2f, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2f, 0x76, 0x32, 0x2f, 0x61,
+	0x67, 0x65, 0x6e, 0x74, 0x2f, 0x61, 0x67, 0x65, 0x6e, 0x74, 0x73, 0x6f, 0x63, 0x6b, 0x65, 0x74,
+	0x2f, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x62, 0x06, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x33,
 }

 var (
@@ -884,41 +749,39 @@ func file_agent_agentsocket_proto_agentsocket_proto_rawDescGZIP() []byte {

 var file_agent_agentsocket_proto_agentsocket_proto_msgTypes = make([]protoimpl.MessageInfo, 13)
 var file_agent_agentsocket_proto_agentsocket_proto_goTypes = []interface{}{
-	(*PingRequest)(nil),           // 0: coder.agentsocket.v1.PingRequest
-	(*PingResponse)(nil),          // 1: coder.agentsocket.v1.PingResponse
-	(*SyncStartRequest)(nil),      // 2: coder.agentsocket.v1.SyncStartRequest
-	(*SyncStartResponse)(nil),     // 3: coder.agentsocket.v1.SyncStartResponse
-	(*SyncWantRequest)(nil),       // 4: coder.agentsocket.v1.SyncWantRequest
-	(*SyncWantResponse)(nil),      // 5: coder.agentsocket.v1.SyncWantResponse
-	(*SyncCompleteRequest)(nil),   // 6: coder.agentsocket.v1.SyncCompleteRequest
-	(*SyncCompleteResponse)(nil),  // 7: coder.agentsocket.v1.SyncCompleteResponse
-	(*SyncReadyRequest)(nil),      // 8: coder.agentsocket.v1.SyncReadyRequest
-	(*SyncReadyResponse)(nil),     // 9: coder.agentsocket.v1.SyncReadyResponse
-	(*SyncStatusRequest)(nil),     // 10: coder.agentsocket.v1.SyncStatusRequest
-	(*DependencyInfo)(nil),        // 11: coder.agentsocket.v1.DependencyInfo
-	(*SyncStatusResponse)(nil),    // 12: coder.agentsocket.v1.SyncStatusResponse
-	(*timestamppb.Timestamp)(nil), // 13: google.protobuf.Timestamp
+	(*PingRequest)(nil),          // 0: coder.agentsocket.v1.PingRequest
+	(*PingResponse)(nil),         // 1: coder.agentsocket.v1.PingResponse
+	(*SyncStartRequest)(nil),     // 2: coder.agentsocket.v1.SyncStartRequest
+	(*SyncStartResponse)(nil),    // 3: coder.agentsocket.v1.SyncStartResponse
+	(*SyncWantRequest)(nil),      // 4: coder.agentsocket.v1.SyncWantRequest
+	(*SyncWantResponse)(nil),     // 5: coder.agentsocket.v1.SyncWantResponse
+	(*SyncCompleteRequest)(nil),  // 6: coder.agentsocket.v1.SyncCompleteRequest
+	(*SyncCompleteResponse)(nil), // 7: coder.agentsocket.v1.SyncCompleteResponse
+	(*SyncReadyRequest)(nil),     // 8: coder.agentsocket.v1.SyncReadyRequest
+	(*SyncReadyResponse)(nil),    // 9: coder.agentsocket.v1.SyncReadyResponse
+	(*SyncStatusRequest)(nil),    // 10: coder.agentsocket.v1.SyncStatusRequest
+	(*DependencyInfo)(nil),       // 11: coder.agentsocket.v1.DependencyInfo
+	(*SyncStatusResponse)(nil),   // 12: coder.agentsocket.v1.SyncStatusResponse
 }
 var file_agent_agentsocket_proto_agentsocket_proto_depIdxs = []int32{
-	13, // 0: coder.agentsocket.v1.PingResponse.timestamp:type_name -> google.protobuf.Timestamp
-	11, // 1: coder.agentsocket.v1.SyncStatusResponse.dependencies:type_name -> coder.agentsocket.v1.DependencyInfo
-	0,  // 2: coder.agentsocket.v1.AgentSocket.Ping:input_type -> coder.agentsocket.v1.PingRequest
-	2,  // 3: coder.agentsocket.v1.AgentSocket.SyncStart:input_type -> coder.agentsocket.v1.SyncStartRequest
-	4,  // 4: coder.agentsocket.v1.AgentSocket.SyncWant:input_type -> coder.agentsocket.v1.SyncWantRequest
-	6,  // 5: coder.agentsocket.v1.AgentSocket.SyncComplete:input_type -> coder.agentsocket.v1.SyncCompleteRequest
-	8,  // 6: coder.agentsocket.v1.AgentSocket.SyncReady:input_type -> coder.agentsocket.v1.SyncReadyRequest
-	10, // 7: coder.agentsocket.v1.AgentSocket.SyncStatus:input_type -> coder.agentsocket.v1.SyncStatusRequest
-	1,  // 8: coder.agentsocket.v1.AgentSocket.Ping:output_type -> coder.agentsocket.v1.PingResponse
-	3,  // 9: coder.agentsocket.v1.AgentSocket.SyncStart:output_type -> coder.agentsocket.v1.SyncStartResponse
-	5,  // 10: coder.agentsocket.v1.AgentSocket.SyncWant:output_type -> coder.agentsocket.v1.SyncWantResponse
-	7,  // 11: coder.agentsocket.v1.AgentSocket.SyncComplete:output_type -> coder.agentsocket.v1.SyncCompleteResponse
-	9,  // 12: coder.agentsocket.v1.AgentSocket.SyncReady:output_type -> coder.agentsocket.v1.SyncReadyResponse
-	12, // 13: coder.agentsocket.v1.AgentSocket.SyncStatus:output_type -> coder.agentsocket.v1.SyncStatusResponse
-	8,  // [8:14] is the sub-list for method output_type
-	2,  // [2:8] is the sub-list for method input_type
-	2,  // [2:2] is the sub-list for extension type_name
-	2,  // [2:2] is the sub-list for extension extendee
-	0,  // [0:2] is the sub-list for field type_name
+	11, // 0: coder.agentsocket.v1.SyncStatusResponse.dependencies:type_name -> coder.agentsocket.v1.DependencyInfo
+	0,  // 1: coder.agentsocket.v1.AgentSocket.Ping:input_type -> coder.agentsocket.v1.PingRequest
+	2,  // 2: coder.agentsocket.v1.AgentSocket.SyncStart:input_type -> coder.agentsocket.v1.SyncStartRequest
+	4,  // 3: coder.agentsocket.v1.AgentSocket.SyncWant:input_type -> coder.agentsocket.v1.SyncWantRequest
+	6,  // 4: coder.agentsocket.v1.AgentSocket.SyncComplete:input_type -> coder.agentsocket.v1.SyncCompleteRequest
+	8,  // 5: coder.agentsocket.v1.AgentSocket.SyncReady:input_type -> coder.agentsocket.v1.SyncReadyRequest
+	10, // 6: coder.agentsocket.v1.AgentSocket.SyncStatus:input_type -> coder.agentsocket.v1.SyncStatusRequest
+	1,  // 7: coder.agentsocket.v1.AgentSocket.Ping:output_type -> coder.agentsocket.v1.PingResponse
+	3,  // 8: coder.agentsocket.v1.AgentSocket.SyncStart:output_type -> coder.agentsocket.v1.SyncStartResponse
+	5,  // 9: coder.agentsocket.v1.AgentSocket.SyncWant:output_type -> coder.agentsocket.v1.SyncWantResponse
+	7,  // 10: coder.agentsocket.v1.AgentSocket.SyncComplete:output_type -> coder.agentsocket.v1.SyncCompleteResponse
+	9,  // 11: coder.agentsocket.v1.AgentSocket.SyncReady:output_type -> coder.agentsocket.v1.SyncReadyResponse
+	12, // 12: coder.agentsocket.v1.AgentSocket.SyncStatus:output_type -> coder.agentsocket.v1.SyncStatusResponse
+	7,  // [7:13] is the sub-list for method output_type
+	1,  // [1:7] is the sub-list for method input_type
+	1,  // [1:1] is the sub-list for extension type_name
+	1,  // [1:1] is the sub-list for extension extendee
+	0,  // [0:1] is the sub-list for field type_name
 }

 func init() { file_agent_agentsocket_proto_agentsocket_proto_init() }
@@ -3,86 +3,67 @@ option go_package = "github.com/coder/coder/v2/agent/agentsocket/proto";

 package coder.agentsocket.v1;

-import "google/protobuf/timestamp.proto";
-
 message PingRequest {}

-message PingResponse {
-	string message = 1;
-	google.protobuf.Timestamp timestamp = 2;
-}
+message PingResponse {}

 message SyncStartRequest {
-	string unit = 1;
+  string unit = 1;
 }

-message SyncStartResponse {
-	bool success = 1;
-	string message = 2;
-}
+message SyncStartResponse {}

 message SyncWantRequest {
-	string unit = 1;
-	string depends_on = 2;
+  string unit = 1;
+  string depends_on = 2;
 }

-message SyncWantResponse {
-	bool success = 1;
-	string message = 2;
-}
+message SyncWantResponse {}

 message SyncCompleteRequest {
-	string unit = 1;
+  string unit = 1;
 }

-message SyncCompleteResponse {
-	bool success = 1;
-	string message = 2;
-}
+message SyncCompleteResponse {}

 message SyncReadyRequest {
-	string unit = 1;
+  string unit = 1;
 }

 message SyncReadyResponse {
-	bool success = 1;
-	string message = 2;
+  bool ready = 1;
 }

 message SyncStatusRequest {
-	string unit = 1;
-	bool recursive = 2;
+  string unit = 1;
 }

 message DependencyInfo {
-	string depends_on = 1;
-	string required_status = 2;
-	string current_status = 3;
-	bool is_satisfied = 4;
+  string unit = 1;
+  string depends_on = 2;
+  string required_status = 3;
+  string current_status = 4;
+  bool is_satisfied = 5;
 }

 message SyncStatusResponse {
-	bool success = 1;
-	string message = 2;
-	string unit = 3;
-	string status = 4;
-	bool is_ready = 5;
-	repeated DependencyInfo dependencies = 6;
-	string dot = 7;
+  string status = 1;
+  bool is_ready = 2;
+  repeated DependencyInfo dependencies = 3;
 }

 // AgentSocket provides direct access to the agent over local IPC.
 service AgentSocket {
  // Ping the agent to check if it is alive.
-	rpc Ping(PingRequest) returns (PingResponse);
+  rpc Ping(PingRequest) returns (PingResponse);
  // Report the start of a unit.
-	rpc SyncStart(SyncStartRequest) returns (SyncStartResponse);
+  rpc SyncStart(SyncStartRequest) returns (SyncStartResponse);
  // Declare a dependency between units.
-	rpc SyncWant(SyncWantRequest) returns (SyncWantResponse);
+  rpc SyncWant(SyncWantRequest) returns (SyncWantResponse);
  // Report the completion of a unit.
-	rpc SyncComplete(SyncCompleteRequest) returns (SyncCompleteResponse);
+  rpc SyncComplete(SyncCompleteRequest) returns (SyncCompleteResponse);
  // Request whether a unit is ready to be started. That is, all dependencies are satisfied.
-	rpc SyncReady(SyncReadyRequest) returns (SyncReadyResponse);
+  rpc SyncReady(SyncReadyRequest) returns (SyncReadyResponse);
  // Get the status of a unit and list its dependencies.
-	rpc SyncStatus(SyncStatusRequest) returns (SyncStatusResponse);
+  rpc SyncStatus(SyncStatusRequest) returns (SyncStatusResponse);
 }
@@ -5,11 +5,8 @@ import (
 	"errors"
 	"net"
 	"sync"
-	"time"

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

@@ -24,23 +21,30 @@ import (
 type Server struct {
 	logger     slog.Logger
 	path       string
-	listener   net.Listener
-	mu         sync.RWMutex
-	ctx        context.Context
-	cancel     context.CancelFunc
-	wg         sync.WaitGroup
 	drpcServer *drpcserver.Server
 	service    *DRPCAgentSocketService
+
+	mu       sync.Mutex
+	listener net.Listener
+	ctx      context.Context
+	cancel   context.CancelFunc
+	wg       sync.WaitGroup
 }

-func NewServer(path string, logger slog.Logger) (*Server, error) {
-	logger = logger.Named("agentsocket")
+// 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[string, string](),
+			unitManager: unit.NewManager(),
 		},
 	}

@@ -61,54 +65,34 @@ func NewServer(path string, logger slog.Logger) (*Server, error) {
 		},
 	})

+	listener, err := createSocket(server.path)
+	if err != nil {
+		return nil, xerrors.Errorf("create socket: %w", err)
+	}
+
+	server.listener = listener
+
+	// This context is canceled by server.Close().
+	// canceling it will close all connections.
+	server.ctx, server.cancel = context.WithCancel(context.Background())
+
+	server.logger.Info(server.ctx, "agent socket server started", slog.F("path", server.path))
+
+	server.wg.Add(1)
+	go func() {
+		defer server.wg.Done()
+		server.acceptConnections()
+	}()
+
 	return server, nil
 }

-var ErrServerAlreadyStarted = xerrors.New("server already started")
-
-func (s *Server) Start() error {
+// Close stops the server and cleans up resources.
+func (s *Server) Close() error {
 	s.mu.Lock()
-	defer s.mu.Unlock()
-
-	if s.listener != nil {
-		return ErrServerAlreadyStarted
-	}
-
-	// This context is canceled by s.Stop() when the server is stopped.
-	// canceling it will close all connections.
-	s.ctx, s.cancel = context.WithCancel(context.Background())
-
-	if s.path == "" {
-		var err error
-		s.path, err = getDefaultSocketPath()
-		if err != nil {
-			return xerrors.Errorf("get default socket path: %w", err)
-		}
-	}
-
-	listener, err := createSocket(s.path)
-	if err != nil {
-		return xerrors.Errorf("create socket: %w", err)
-	}
-
-	s.listener = listener
-
-	s.logger.Info(s.ctx, "agent socket server started", slog.F("path", s.path))
-
-	s.wg.Add(1)
-	go func() {
-		defer s.wg.Done()
-		s.acceptConnections()
-	}()
-
-	return nil
-}
-
-func (s *Server) Stop() error {
-	s.mu.Lock()
-	defer s.mu.Unlock()

 	if s.listener == nil {
+		s.mu.Unlock()
 		return nil
 	}

@@ -120,6 +104,10 @@ func (s *Server) Stop() error {
 		s.logger.Warn(s.ctx, "error closing socket listener", slog.Error(err))
 	}

+	s.listener = nil
+
+	s.mu.Unlock()
+
 	// Wait for all connections to finish
 	s.wg.Wait()

@@ -127,59 +115,24 @@ func (s *Server) Stop() error {
 		s.logger.Warn(s.ctx, "error cleaning up socket file", slog.Error(err))
 	}

-	s.listener = nil
 	s.logger.Info(s.ctx, "agent socket server stopped")

 	return nil
 }

 func (s *Server) acceptConnections() {
-	for {
-		select {
-		case <-s.ctx.Done():
-			return
-		default:
-		}
-
-		conn, err := s.listener.Accept()
-		if err != nil {
-			select {
-			case <-s.ctx.Done():
-				return
-			default:
-				s.logger.Warn(s.ctx, "error accepting connection", slog.Error(err))
-				continue
-			}
-		}
-
-		s.wg.Add(1)
-		go func() {
-			defer s.wg.Done()
-			s.handleConnection(conn)
-		}()
-	}
-}
-
-func (s *Server) handleConnection(conn net.Conn) {
-	defer conn.Close()
-
-	if err := conn.SetDeadline(time.Now().Add(30 * time.Second)); err != nil {
-		s.logger.Warn(s.ctx, "failed to set connection deadline", slog.Error(err))
-	}
-
-	s.logger.Debug(s.ctx, "new connection accepted", slog.F("remote_addr", conn.RemoteAddr()))
-
-	config := yamux.DefaultConfig()
-	config.Logger = nil
-	session, err := yamux.Server(conn, config)
-	if err != nil {
-		s.logger.Warn(s.ctx, "failed to create yamux session", slog.Error(err))
+	// In an edge case, Close() might race with acceptConnections() and set s.listener to nil.
+	// Therefore, we grab a copy of the listener under a lock. We might still get a nil listener,
+	// but then we know close has already run and we can return early.
+	s.mu.Lock()
+	listener := s.listener
+	s.mu.Unlock()
+	if listener == nil {
 		return
 	}
-	defer session.Close()

-	err = s.drpcServer.Serve(s.ctx, session)
+	err := s.drpcServer.Serve(s.ctx, listener)
 	if err != nil {
-		s.logger.Debug(s.ctx, "drpc server finished", slog.Error(err))
+		s.logger.Warn(s.ctx, "error serving drpc server", slog.Error(err))
 	}
 }
@@ -1,27 +1,41 @@
 package agentsocket_test

 import (
+	"context"
 	"path/filepath"
+	"runtime"
 	"testing"

+	"github.com/google/uuid"
+	"github.com/spf13/afero"
 	"github.com/stretchr/testify/require"

 	"cdr.dev/slog"
+	"github.com/coder/coder/v2/agent"
 	"github.com/coder/coder/v2/agent/agentsocket"
+	"github.com/coder/coder/v2/agent/agenttest"
+	agentproto "github.com/coder/coder/v2/agent/proto"
+	"github.com/coder/coder/v2/codersdk/agentsdk"
+	"github.com/coder/coder/v2/tailnet"
+	"github.com/coder/coder/v2/tailnet/tailnettest"
+	"github.com/coder/coder/v2/testutil"
 )

 func TestServer(t *testing.T) {
 	t.Parallel()

+	if runtime.GOOS == "windows" {
+		t.Skip("agentsocket is not supported on Windows")
+	}
+
 	t.Run("StartStop", func(t *testing.T) {
 		t.Parallel()

 		socketPath := filepath.Join(t.TempDir(), "test.sock")
 		logger := slog.Make().Leveled(slog.LevelDebug)
-		server, err := agentsocket.NewServer(socketPath, logger)
+		server, err := agentsocket.NewServer(logger, agentsocket.WithPath(socketPath))
 		require.NoError(t, err)
-		require.NoError(t, server.Start())
-		require.NoError(t, server.Stop())
+		require.NoError(t, server.Close())
 	})

 	t.Run("AlreadyStarted", func(t *testing.T) {
@@ -29,10 +43,11 @@ func TestServer(t *testing.T) {

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

 	t.Run("AutoSocketPath", func(t *testing.T) {
@@ -40,9 +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.Start())
-		require.NoError(t, server.Stop())
+		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")
+}
@@ -3,10 +3,8 @@ package agentsocket
 import (
 	"context"
 	"errors"
-	"sync"
-	"time"

-	"google.golang.org/protobuf/types/known/timestamppb"
+	"golang.org/x/xerrors"

 	"cdr.dev/slog"
 	"github.com/coder/coder/v2/agent/agentsocket/proto"
@@ -15,248 +13,140 @@ import (

 var _ proto.DRPCAgentSocketServer = (*DRPCAgentSocketService)(nil)

+var ErrUnitManagerNotAvailable = xerrors.New("unit manager not available")
+
+// DRPCAgentSocketService implements the DRPC agent socket service.
 type DRPCAgentSocketService struct {
-	mu          sync.RWMutex
-	unitManager *unit.Manager[string, string]
+	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{
-		Message:   "pong",
-		Timestamp: timestamppb.New(time.Now()),
-	}, nil
+	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 &proto.SyncStartResponse{
-			Success: false,
-			Message: "dependency tracker not available",
-		}, nil
+		return nil, xerrors.Errorf("SyncStart: %w", ErrUnitManagerNotAvailable)
 	}

-	if req.Unit == "" {
-		return &proto.SyncStartResponse{
-			Success: false,
-			Message: "Unit name is required",
-		}, nil
-	}
+	unitID := unit.ID(req.Unit)

-	if err := s.unitManager.Register(req.Unit); err != nil {
-		// If already registered, that's okay - we can still update status
-		if !errors.Is(err, unit.ErrConsumerAlreadyRegistered) {
-			return &proto.SyncStartResponse{
-				Success: false,
-				Message: "Failed to register unit: " + err.Error(),
-			}, nil
+	if err := s.unitManager.Register(unitID); err != nil {
+		if !errors.Is(err, unit.ErrUnitAlreadyRegistered) {
+			return nil, xerrors.Errorf("SyncStart: %w", err)
 		}
 	}

-	isReady, err := s.unitManager.IsReady(req.Unit)
+	isReady, err := s.unitManager.IsReady(unitID)
 	if err != nil {
-		return &proto.SyncStartResponse{
-			Success: false,
-			Message: "Failed to check readiness: " + err.Error(),
-		}, nil
+		return nil, xerrors.Errorf("cannot check readiness: %w", err)
 	}
 	if !isReady {
-		return &proto.SyncStartResponse{
-			Success: false,
-			Message: "Unit is not ready",
-		}, nil
+		return nil, xerrors.Errorf("cannot start unit %q: unit not ready", req.Unit)
 	}

-	if err := s.unitManager.UpdateStatus(req.Unit, unit.StatusStarted); err != nil {
-		return &proto.SyncStartResponse{
-			Success: false,
-			Message: "Failed to update status: " + err.Error(),
-		}, nil
+	err = s.unitManager.UpdateStatus(unitID, unit.StatusStarted)
+	if err != nil {
+		return nil, xerrors.Errorf("cannot start unit %q: %w", req.Unit, err)
 	}

-	return &proto.SyncStartResponse{
-		Success: true,
-		Message: "Unit " + req.Unit + " started successfully",
-	}, nil
+	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 &proto.SyncWantResponse{
-			Success: false,
-			Message: "unit manager not available",
-		}, nil
+		return nil, xerrors.Errorf("cannot add dependency: %w", ErrUnitManagerNotAvailable)
 	}

-	if req.Unit == "" || req.DependsOn == "" {
-		return &proto.SyncWantResponse{
-			Success: false,
-			Message: "unit and depends_on are required",
-		}, nil
+	unitID := unit.ID(req.Unit)
+	dependsOnID := unit.ID(req.DependsOn)
+
+	if err := s.unitManager.Register(unitID); err != nil && !errors.Is(err, unit.ErrUnitAlreadyRegistered) {
+		return nil, xerrors.Errorf("cannot add dependency: %w", err)
 	}

-	if err := s.unitManager.Register(req.Unit); err != nil {
-		if !errors.Is(err, unit.ErrConsumerAlreadyRegistered) {
-			return &proto.SyncWantResponse{
-				Success: false,
-				Message: "failed to register unit: " + err.Error(),
-			}, nil
-		}
+	if err := s.unitManager.AddDependency(unitID, dependsOnID, unit.StatusComplete); err != nil {
+		return nil, xerrors.Errorf("cannot add dependency: %w", err)
 	}

-	if err := s.unitManager.Register(req.DependsOn); err != nil {
-		if !errors.Is(err, unit.ErrConsumerAlreadyRegistered) {
-			return &proto.SyncWantResponse{
-				Success: false,
-				Message: "failed to register dependency unit: " + err.Error(),
-			}, nil
-		}
-	}
-
-	if err := s.unitManager.AddDependency(req.Unit, req.DependsOn, unit.StatusComplete); err != nil {
-		return &proto.SyncWantResponse{
-			Success: false,
-			Message: "failed to add dependency: " + err.Error(),
-		}, nil
-	}
-
-	return &proto.SyncWantResponse{
-		Success: true,
-		Message: "Unit " + req.Unit + " now depends on " + req.DependsOn,
-	}, nil
+	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 &proto.SyncCompleteResponse{
-			Success: false,
-			Message: "unit manager not available",
-		}, nil
+		return nil, xerrors.Errorf("cannot complete unit: %w", ErrUnitManagerNotAvailable)
 	}

-	if req.Unit == "" {
-		return &proto.SyncCompleteResponse{
-			Success: false,
-			Message: "unit name is required",
-		}, nil
+	unitID := unit.ID(req.Unit)
+
+	if err := s.unitManager.UpdateStatus(unitID, unit.StatusComplete); err != nil {
+		return nil, xerrors.Errorf("cannot complete unit %q: %w", req.Unit, err)
 	}

-	if err := s.unitManager.UpdateStatus(req.Unit, unit.StatusComplete); err != nil {
-		return &proto.SyncCompleteResponse{
-			Success: false,
-			Message: "failed to update status: " + err.Error(),
-		}, nil
-	}
-
-	return &proto.SyncCompleteResponse{
-		Success: true,
-		Message: "unit " + req.Unit + " completed successfully",
-	}, nil
+	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 &proto.SyncReadyResponse{
-			Success: false,
-			Message: "unit manager not available",
-		}, nil
+		return nil, xerrors.Errorf("cannot check readiness: %w", ErrUnitManagerNotAvailable)
 	}

-	if req.Unit == "" {
-		return &proto.SyncReadyResponse{
-			Success: false,
-			Message: "unit name is required",
-		}, nil
-	}
-
-	isReady, err := s.unitManager.IsReady(req.Unit)
+	unitID := unit.ID(req.Unit)
+	isReady, err := s.unitManager.IsReady(unitID)
 	if err != nil {
-		return &proto.SyncReadyResponse{
-			Success: false,
-			Message: "failed to check readiness: " + err.Error(),
-		}, nil
-	}
-
-	if !isReady {
-		return &proto.SyncReadyResponse{
-			Success: false,
-			Message: unit.ErrDependenciesNotSatisfied.Error(),
-		}, nil
+		return nil, xerrors.Errorf("cannot check readiness: %w", err)
 	}

 	return &proto.SyncReadyResponse{
-		Success: true,
-		Message: "unit " + req.Unit + " dependencies are satisfied",
+		Ready: isReady,
 	}, nil
 }

+// SyncStatus gets the status of a unit and lists its dependencies.
 func (s *DRPCAgentSocketService) SyncStatus(_ context.Context, req *proto.SyncStatusRequest) (*proto.SyncStatusResponse, error) {
 	if s.unitManager == nil {
-		return &proto.SyncStatusResponse{
-			Success: false,
-			Message: "unit manager not available",
-		}, nil
+		return nil, xerrors.Errorf("cannot get status for unit %q: %w", req.Unit, ErrUnitManagerNotAvailable)
 	}

-	if req.Unit == "" {
-		return &proto.SyncStatusResponse{
-			Success: false,
-			Message: "unit name is required",
-		}, nil
-	}
+	unitID := unit.ID(req.Unit)

-	status, err := s.unitManager.GetStatus(req.Unit)
+	isReady, err := s.unitManager.IsReady(unitID)
 	if err != nil {
-		return &proto.SyncStatusResponse{
-			Success: false,
-			Message: "failed to get unit status: " + err.Error(),
-		}, nil
+		return nil, xerrors.Errorf("cannot check readiness: %w", err)
 	}

-	isReady, err := s.unitManager.IsReady(req.Unit)
-	if err != nil {
-		return &proto.SyncStatusResponse{
-			Success: false,
-			Message: "failed to check readiness: " + err.Error(),
-		}, nil
-	}
-
-	dependencies, err := s.unitManager.GetAllDependencies(req.Unit)
-	if err != nil {
-		return &proto.SyncStatusResponse{
-			Success: false,
-			Message: "failed to get dependencies: " + err.Error(),
-		}, nil
+	dependencies, err := s.unitManager.GetAllDependencies(unitID)
+	switch {
+	case errors.Is(err, unit.ErrUnitNotFound):
+		dependencies = []unit.Dependency{}
+	case err != nil:
+		return nil, xerrors.Errorf("cannot get dependencies: %w", err)
 	}

 	var depInfos []*proto.DependencyInfo
 	for _, dep := range dependencies {
 		depInfos = append(depInfos, &proto.DependencyInfo{
-			DependsOn:      dep.DependsOn,
-			RequiredStatus: dep.RequiredStatus,
-			CurrentStatus:  dep.CurrentStatus,
+			Unit:           string(dep.Unit),
+			DependsOn:      string(dep.DependsOn),
+			RequiredStatus: string(dep.RequiredStatus),
+			CurrentStatus:  string(dep.CurrentStatus),
 			IsSatisfied:    dep.IsSatisfied,
 		})
 	}

-	var dotStr string
-	if req.Recursive {
-		dotStr, err = s.unitManager.ExportDOT("dependency_graph")
-		if err != nil {
-			return &proto.SyncStatusResponse{
-				Success: false,
-				Message: "failed to export DOT: " + err.Error(),
-			}, nil
-		}
+	u, err := s.unitManager.Unit(unitID)
+	if err != nil {
+		return nil, xerrors.Errorf("cannot get status for unit %q: %w", req.Unit, err)
 	}
-
 	return &proto.SyncStatusResponse{
-		Success:      true,
-		Message:      "unit status retrieved successfully",
-		Unit:         req.Unit,
-		Status:       status,
+		Status:       string(u.Status()),
 		IsReady:      isReady,
 		Dependencies: depInfos,
-		Dot:          dotStr,
 	}, nil
 }
@@ -2,44 +2,83 @@ package agentsocket_test

 import (
 	"context"
+	"crypto/sha256"
+	"encoding/hex"
+	"fmt"
+	"os"
 	"path/filepath"
+	"runtime"
 	"testing"

+	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"

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

+// tempDirUnixSocket returns a temporary directory that can safely hold unix
+// sockets (probably).
+//
+// During tests on darwin we hit the max path length limit for unix sockets
+// pretty easily in the default location, so this function uses /tmp instead to
+// get shorter paths. To keep paths short, we use a hash of the test name
+// instead of the full test name.
+func tempDirUnixSocket(t *testing.T) string {
+	t.Helper()
+	if runtime.GOOS == "darwin" {
+		// Use a short hash of the test name to keep the path under 104 chars
+		hash := sha256.Sum256([]byte(t.Name()))
+		hashStr := hex.EncodeToString(hash[:])[:8] // Use first 8 chars of hash
+		dir, err := os.MkdirTemp("/tmp", fmt.Sprintf("c-%s-", hashStr))
+		require.NoError(t, err, "create temp dir for unix socket test")
+		t.Cleanup(func() {
+			err := os.RemoveAll(dir)
+			assert.NoError(t, err, "remove temp dir", dir)
+		})
+		return dir
+	}
+	return t.TempDir()
+}
+
+// newSocketClient creates a DRPC client connected to the Unix socket at the given path.
+func newSocketClient(ctx context.Context, t *testing.T, socketPath string) *agentsocket.Client {
+	t.Helper()
+
+	client, err := agentsocket.NewClient(ctx, agentsocket.WithPath(socketPath))
+	t.Cleanup(func() {
+		_ = client.Close()
+	})
+	require.NoError(t, err)
+
+	return client
+}
+
 func TestDRPCAgentSocketService(t *testing.T) {
 	t.Parallel()

+	if runtime.GOOS == "windows" {
+		t.Skip("agentsocket is not supported on Windows")
+	}
+
 	t.Run("Ping", func(t *testing.T) {
 		t.Parallel()

-		socketPath := filepath.Join(t.TempDir(), "test.sock")
-
+		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()

-		err = server.Start()
-		require.NoError(t, err)
-		defer server.Stop()
+		client := newSocketClient(ctx, t, socketPath)

-		client, err := agentsdk.NewSocketClient(agentsdk.SocketConfig{
-			Path: socketPath,
-		})
+		err = client.Ping(ctx)
 		require.NoError(t, err)
-		defer client.Close()
-
-		response, err := client.Ping(context.Background())
-		require.NoError(t, err)
-		require.Equal(t, "pong", response.Message)
 	})

 	t.Run("SyncStart", func(t *testing.T) {
@@ -47,146 +86,118 @@ func TestDRPCAgentSocketService(t *testing.T) {

 		t.Run("NewUnit", func(t *testing.T) {
 			t.Parallel()
-			socketPath := filepath.Join(t.TempDir(), "test.sock")
-
+			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)
-			err = server.Start()
-			require.NoError(t, err)
-			defer server.Stop()
+			defer server.Close()

-			client, err := agentsdk.NewSocketClient(agentsdk.SocketConfig{
-				Path: socketPath,
-			})
-			require.NoError(t, err)
-			defer client.Close()
+			client := newSocketClient(ctx, t, socketPath)

-			err = client.SyncStart(context.Background(), "test-unit")
+			err = client.SyncStart(ctx, "test-unit")
 			require.NoError(t, err)

-			status, err := client.SyncStatus(context.Background(), "test-unit", false)
+			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(t.TempDir(), "test.sock")
-
+			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)
-			err = server.Start()
-			require.NoError(t, err)
-			defer server.Stop()
+			defer server.Close()

-			client, err := agentsdk.NewSocketClient(agentsdk.SocketConfig{
-				Path: socketPath,
-			})
-			require.NoError(t, err)
-			defer client.Close()
-
-			err = client.SyncStart(context.Background(), "test-unit")
-			require.NoError(t, err)
+			client := newSocketClient(ctx, t, socketPath)

 			// First Start
-			status, err := client.SyncStatus(context.Background(), "test-unit", false)
+			err = client.SyncStart(ctx, "test-unit")
 			require.NoError(t, err)
-			require.Equal(t, "started", status.Status)
-
-			status, err = client.SyncStatus(context.Background(), "test-unit", false)
+			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(), "test-unit")
+			err = client.SyncStart(ctx, "test-unit")
 			require.ErrorContains(t, err, unit.ErrSameStatusAlreadySet.Error())

-			status, err = client.SyncStatus(context.Background(), "test-unit", false)
+			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(t.TempDir(), "test.sock")
-
+			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)
-			err = server.Start()
-			require.NoError(t, err)
-			defer server.Stop()
+			defer server.Close()

-			client, err := agentsdk.NewSocketClient(agentsdk.SocketConfig{
-				Path: socketPath,
-			})
-			require.NoError(t, err)
-			defer client.Close()
+			client := newSocketClient(ctx, t, socketPath)

 			// First start
-			err = client.SyncStart(context.Background(), "test-unit")
+			err = client.SyncStart(ctx, "test-unit")
 			require.NoError(t, err)

-			status, err := client.SyncStatus(context.Background(), "test-unit", false)
+			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(), "test-unit")
+			err = client.SyncComplete(ctx, "test-unit")
 			require.NoError(t, err)

-			status, err = client.SyncStatus(context.Background(), "test-unit", false)
+			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(), "test-unit")
+			err = client.SyncStart(ctx, "test-unit")
 			require.NoError(t, err)

-			status, err = client.SyncStatus(context.Background(), "test-unit", false)
+			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(t.TempDir(), "test.sock")
-
+			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)
-			err = server.Start()
-			require.NoError(t, err)
-			defer server.Stop()
+			defer server.Close()

-			client, err := agentsdk.NewSocketClient(agentsdk.SocketConfig{
-				Path: socketPath,
-			})
-			require.NoError(t, err)
-			defer client.Close()
+			client := newSocketClient(ctx, t, socketPath)

-			client.SyncWant(context.Background(), "test-unit", "dependency-unit")
+			err = client.SyncWant(ctx, "test-unit", "dependency-unit")
 			require.NoError(t, err)

-			err = client.SyncStart(context.Background(), "test-unit")
-			require.ErrorContains(t, err, "Unit is not ready")
+			err = client.SyncStart(ctx, "test-unit")
+			require.ErrorContains(t, err, "unit not ready")

-			status, err := client.SyncStatus(context.Background(), "test-unit", false)
+			status, err := client.SyncStatus(ctx, "test-unit")
 			require.NoError(t, err)
-			require.Equal(t, "", status.Status)
+			require.Equal(t, unit.StatusPending, status.Status)
+			require.False(t, status.IsReady)
 		})
 	})

@@ -196,104 +207,87 @@ func TestDRPCAgentSocketService(t *testing.T) {
 		t.Run("NewUnits", func(t *testing.T) {
 			t.Parallel()

-			socketPath := filepath.Join(t.TempDir(), "test.sock")
-
+			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)
-			err = server.Start()
-			require.NoError(t, err)
-			defer server.Stop()
+			defer server.Close()

-			client, err := agentsdk.NewSocketClient(agentsdk.SocketConfig{
-				Path: socketPath,
-			})
-			require.NoError(t, err)
-			defer client.Close()
+			client := newSocketClient(ctx, t, socketPath)

-			// If units are not registered, they are registered automatically
-			err = client.SyncWant(context.Background(), "test-unit", "dependency-unit")
+			// If dependency units are not registered, they are registered automatically
+			err = client.SyncWant(ctx, "test-unit", "dependency-unit")
 			require.NoError(t, err)

-			status, err := client.SyncStatus(context.Background(), "test-unit", false)
+			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.Len(t, status.Dependencies, 1)
+			require.Equal(t, unit.ID("dependency-unit"), status.Dependencies[0].DependsOn)
+			require.Equal(t, unit.StatusComplete, status.Dependencies[0].RequiredStatus)
 		})

 		t.Run("DependencyAlreadyRegistered", func(t *testing.T) {
 			t.Parallel()

-			socketPath := filepath.Join(t.TempDir(), "test.sock")
-
+			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)
-			err = server.Start()
-			require.NoError(t, err)
-			defer server.Stop()
+			defer server.Close()

-			client, err := agentsdk.NewSocketClient(agentsdk.SocketConfig{
-				Path: socketPath,
-			})
-			require.NoError(t, err)
-			defer client.Close()
+			client := newSocketClient(ctx, t, socketPath)

 			// Start the dependency unit
-			err = client.SyncStart(context.Background(), "dependency-unit")
+			err = client.SyncStart(ctx, "dependency-unit")
 			require.NoError(t, err)

-			status, err := client.SyncStatus(context.Background(), "dependency-unit", false)
+			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(), "test-unit", "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(), "test-unit", false)
+			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(t.TempDir(), "test.sock")
-
+			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)
-			err = server.Start()
-			require.NoError(t, err)
-			defer server.Stop()
+			defer server.Close()

-			client, err := agentsdk.NewSocketClient(agentsdk.SocketConfig{
-				Path: socketPath,
-			})
-			require.NoError(t, err)
-			defer client.Close()
+			client := newSocketClient(ctx, t, socketPath)

 			// Start the dependent unit
-			err = client.SyncStart(context.Background(), "test-unit")
+			err = client.SyncStart(ctx, "test-unit")
 			require.NoError(t, err)

-			status, err := client.SyncStatus(context.Background(), "test-unit", false)
+			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(), "test-unit", "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.
@@ -302,10 +296,94 @@ 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(), "test-unit", false)
+			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("SyncReady", func(t *testing.T) {
+		t.Parallel()
+
+		t.Run("UnregisteredUnit", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+			ctx := testutil.Context(t, testutil.WaitShort)
+			server, err := agentsocket.NewServer(
+				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(ctx, t, socketPath)
+
+			ready, err := client.SyncReady(ctx, "unregistered-unit")
+			require.NoError(t, err)
+			require.True(t, ready)
+		})
+
+		t.Run("UnitNotReady", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+			ctx := testutil.Context(t, testutil.WaitShort)
+			server, err := agentsocket.NewServer(
+				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(ctx, t, socketPath)
+
+			// Register a unit with an unsatisfied dependency
+			err = client.SyncWant(ctx, "test-unit", "dependency-unit")
+			require.NoError(t, err)
+
+			// Check readiness - should be false because dependency is not satisfied
+			ready, err := client.SyncReady(ctx, "test-unit")
+			require.NoError(t, err)
+			require.False(t, ready)
+		})
+
+		t.Run("UnitReady", func(t *testing.T) {
+			t.Parallel()
+
+			socketPath := filepath.Join(tempDirUnixSocket(t), "test.sock")
+			ctx := testutil.Context(t, testutil.WaitShort)
+			server, err := agentsocket.NewServer(
+				slog.Make().Leveled(slog.LevelDebug),
+				agentsocket.WithPath(socketPath),
+			)
+			require.NoError(t, err)
+			defer server.Close()
+
+			client := newSocketClient(ctx, t, socketPath)
+
+			// Register a unit with no dependencies - should be ready immediately
+			err = client.SyncStart(ctx, "test-unit")
+			require.NoError(t, err)
+
+			// Check readiness - should be true
+			ready, err := client.SyncReady(ctx, "test-unit")
+			require.NoError(t, err)
+			require.True(t, ready)
+
+			// Also test a unit with satisfied dependencies
+			err = client.SyncWant(ctx, "dependent-unit", "test-unit")
+			require.NoError(t, err)
+
+			// Complete the dependency
+			err = client.SyncComplete(ctx, "test-unit")
+			require.NoError(t, err)
+
+			// Now dependent-unit should be ready
+			ready, err = client.SyncReady(ctx, "dependent-unit")
+			require.NoError(t, err)
+			require.True(t, ready)
 		})
 	})
 }
@@ -3,16 +3,22 @@
 package agentsocket

 import (
-	"fmt"
+	"context"
 	"net"
 	"os"
 	"path/filepath"
+	"time"

 	"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)
 	}
@@ -21,7 +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)
@@ -39,38 +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) {
-	// Try XDG_RUNTIME_DIR first
-	if runtimeDir := os.Getenv("XDG_RUNTIME_DIR"); runtimeDir != "" {
-		return filepath.Join(runtimeDir, "coder-agent.sock"), nil
-	}
-
-	// Fall back to /tmp with user-specific path
-	uid := os.Getuid()
-	return filepath.Join("/tmp", fmt.Sprintf("coder-agent-%d.sock", uid)), 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
-	conn, err := net.Dial("unix", path)
+	// 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)
+}
@@ -4,108 +4,19 @@ package agentsocket

 import (
 	"context"
-	"fmt"
 	"net"
-	"os"
-	"path/filepath"
-	"strconv"
-	"time"

-	"cdr.dev/slog"
+	"golang.org/x/xerrors"
 )

-// createSocket creates a Unix domain socket listener on Windows
-// Falls back to named pipe if Unix sockets are not supported
-func CreateSocket(path string) (net.Listener, error) {
-	// Try Unix domain socket first (Windows 10 build 17063+)
-	listener, err := net.Listen("unix", path)
-	if err == nil {
-		return listener, nil
-	}
-
-	// Fall back to named pipe
-	pipePath := `\\.\pipe\coder-agent`
-	listener, err = net.Listen("tcp", pipePath)
-	if err != nil {
-		return nil, err
-	}
-	return listener, nil
+func createSocket(_ string) (net.Listener, error) {
+	return nil, xerrors.New("agentsocket is not supported on Windows")
 }

-// getDefaultSocketPath returns the default socket path for Windows
-func GetDefaultSocketPath() (string, error) {
-	// Try to use a temporary directory
-	tempDir := os.TempDir()
-	if tempDir == "" {
-		tempDir = "C:\\temp"
-	}
-
-	// Create a user-specific subdirectory
-	uid := os.Getuid()
-	userDir := filepath.Join(tempDir, "coder-agent", strconv.Itoa(uid))
-
-	if err := os.MkdirAll(userDir, 0o700); err != nil {
-		return "", fmt.Errorf("create user directory: %w", err)
-	}
-
-	return filepath.Join(userDir, "agent.sock"), nil
+func cleanupSocket(_ string) error {
+	return 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, logger slog.Logger) bool {
-	logger.Debug(context.Background(), "Checking socket availability on Windows", slog.F("path", path))
-
-	// Check if file exists
-	if _, err := os.Stat(path); os.IsNotExist(err) {
-		logger.Debug(context.Background(), "Socket file does not exist, path is available", slog.F("path", path))
-		return true
-	}
-	logger.Debug(context.Background(), "Socket file exists, checking if it's listening", slog.F("path", path))
-
-	// Try to connect to see if it's actually listening
-	conn, err := net.Dial("unix", path)
-	if err != nil {
-		// If we can't connect, the socket is not in use
-		logger.Debug(context.Background(), "Cannot connect to socket, path is available", slog.F("path", path), slog.Error(err))
-		return true
-	}
-	_ = conn.Close()
-	logger.Debug(context.Background(), "Socket is listening, path is not available", slog.F("path", path))
-	return false
-}
-
-// getSocketInfo returns information about the socket file
-func GetSocketInfo(path string) (*SocketInfo, error) {
-	stat, err := os.Stat(path)
-	if err != nil {
-		return nil, err
-	}
-
-	// On Windows, we'll use a simplified approach for now
-	// In a real implementation, you'd get the security descriptor
-	return &SocketInfo{
-		Path:    path,
-		UID:     0, // Simplified for now
-		GID:     0, // Simplified for now
-		Mode:    stat.Mode(),
-		ModTime: stat.ModTime(),
-		Owner:   "unknown",
-		Group:   "unknown",
-	}, nil
-}
-
-// SocketInfo contains information about a socket file
-type SocketInfo struct {
-	Path    string
-	UID     int
-	GID     int
-	Mode    os.FileMode
-	ModTime time.Time
-	Owner   string // Windows SID string
-	Group   string // Windows SID string
+func dialSocket(_ context.Context, _ string) (net.Conn, error) {
+	return nil, xerrors.New("agentsocket is not supported on Windows")
 }
@@ -2,41 +2,31 @@ package agent

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

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

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

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

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

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

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

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

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

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

+	filteredPorts := make([]codersdk.WorkspaceAgentListeningPort, 0, len(ports))
+	for _, port := range ports {
+		if port.Port < workspacesdk.AgentMinimumListeningPort {
+			continue
+		}
+
+		// Ignore ports that we've been told to ignore.
+		if _, ok := lp.ignorePorts[int(port.Port)]; ok {
+			continue
+		}
+		filteredPorts = append(filteredPorts, port)
+	}
+
 	httpapi.Write(r.Context(), rw, http.StatusOK, codersdk.WorkspaceAgentListeningPortsResponse{
-		Ports: ports,
+		Ports: filteredPorts,
 	})
 }
@@ -250,7 +250,9 @@ func (a *agent) editFile(ctx context.Context, path string, edits []workspacesdk.
 		transforms[i] = replace.String(edit.Search, edit.Replace)
 	}

-	tmpfile, err := afero.TempFile(a.filesystem, "", filepath.Base(path))
+	// Create an adjacent file to ensure it will be on the same device and can be
+	// moved atomically.
+	tmpfile, err := afero.TempFile(a.filesystem, filepath.Dir(path), filepath.Base(path))
 	if err != nil {
 		return http.StatusInternalServerError, err
 	}
@@ -3,16 +3,23 @@
 package agent

 import (
+	"sync"
 	"time"

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

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

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

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

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

 package agent

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

-func (*listeningPortsHandler) getListeningPorts() ([]codersdk.WorkspaceAgentListeningPort, error) {
+	"github.com/coder/coder/v2/codersdk"
+)
+
+type osListeningPortsGetter struct {
+	cacheDuration time.Duration
+}
+
+func (*osListeningPortsGetter) GetListeningPorts() ([]codersdk.WorkspaceAgentListeningPort, error) {
 	// Can't scan for ports on non-linux or non-windows_amd64 systems at the
 	// moment. The UI will not show any "no ports found" message to the user, so
 	// the user won't suspect a thing.
@@ -58,7 +58,7 @@ func (g *Graph[EdgeType, VertexType]) AddEdge(from, to VertexType, edge EdgeType
 	toID := g.getOrCreateVertexID(to)

 	if g.canReach(to, from) {
-		return xerrors.Errorf("adding edge (%v -> %v) would create a cycle", from, to)
+		return xerrors.Errorf("adding edge (%v -> %v): %w", from, to, ErrCycleDetected)
 	}

 	g.gonumGraph.SetEdge(simple.Edge{F: simple.Node(fromID), T: simple.Node(toID)})
@@ -148,8 +148,7 @@ func TestGraph(t *testing.T) {
 			graph := &testGraph{}
 			unit1 := &testGraphVertex{Name: "unit1"}
 			err := graph.AddEdge(unit1, unit1, testEdgeCompleted)
-			require.Error(t, err)
-			require.ErrorContains(t, err, fmt.Sprintf("adding edge (%v -> %v) would create a cycle", unit1, unit1))
+			require.ErrorIs(t, err, unit.ErrCycleDetected)

 			return graph
 		},
@@ -160,8 +159,7 @@ func TestGraph(t *testing.T) {
 			err := graph.AddEdge(unit1, unit2, testEdgeCompleted)
 			require.NoError(t, err)
 			err = graph.AddEdge(unit2, unit1, testEdgeStarted)
-			require.Error(t, err)
-			require.ErrorContains(t, err, fmt.Sprintf("adding edge (%v -> %v) would create a cycle", unit2, unit1))
+			require.ErrorIs(t, err, unit.ErrCycleDetected)

 			return graph
 		},
@@ -341,7 +339,7 @@ func TestGraphThreadSafety(t *testing.T) {
 		// Verify all attempts correctly returned cycle error
 		for i, err := range cycleErrors {
 			require.Error(t, err, "goroutine %d should have detected cycle", i)
-			require.Contains(t, err.Error(), "would create a cycle")
+			require.ErrorIs(t, err, unit.ErrCycleDetected)
 		}

 		// Verify graph remains valid (original chain intact)
@@ -1,307 +1,290 @@
 package unit

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

 	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/coderd/util/slice"
 )

-// ErrConsumerNotFound is returned when a consumer ID is not registered.
-var ErrConsumerNotFound = xerrors.New("consumer not found")
-
-// ErrConsumerAlreadyRegistered is returned when a consumer ID is already registered.
-var ErrConsumerAlreadyRegistered = xerrors.New("consumer already registered")
-
-// ErrCannotUpdateOtherConsumer is returned when attempting to update another consumer's status.
-var ErrCannotUpdateOtherConsumer = xerrors.New("cannot update other consumer's status")
-
-// ErrDependenciesNotSatisfied is returned when a consumer's dependencies are not satisfied.
-var ErrDependenciesNotSatisfied = xerrors.New("unit dependencies not satisfied")
-
-// ErrSameStatusAlreadySet is returned when attempting to set the same status as the current status.
-var ErrSameStatusAlreadySet = xerrors.New("same status already set")
-
-// Status constants for dependency tracking
-const (
-	StatusStarted  = "started"
-	StatusComplete = "completed"
+var (
+	ErrUnitIDRequired           = xerrors.New("unit name is required")
+	ErrUnitNotFound             = xerrors.New("unit not found")
+	ErrUnitAlreadyRegistered    = xerrors.New("unit already registered")
+	ErrCannotUpdateOtherUnit    = xerrors.New("cannot update other unit's status")
+	ErrDependenciesNotSatisfied = xerrors.New("unit dependencies not satisfied")
+	ErrSameStatusAlreadySet     = xerrors.New("same status already set")
+	ErrCycleDetected            = xerrors.New("cycle detected")
+	ErrFailedToAddDependency    = xerrors.New("failed to add dependency")
 )

-// dependencyVertex represents a vertex in the dependency graph that is associated with a consumer.
-type dependencyVertex[ConsumerID comparable] struct {
-	ID ConsumerID
+// 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)
 }

-// Dependency represents a dependency relationship between consumers.
-type Dependency[StatusType, ConsumerID comparable] struct {
-	Consumer       ConsumerID
-	DependsOn      ConsumerID
-	RequiredStatus StatusType
-	CurrentStatus  StatusType
+// Status constants for dependency tracking.
+const (
+	StatusNotRegistered Status = ""
+	StatusPending       Status = "pending"
+	StatusStarted       Status = "started"
+	StatusComplete      Status = "completed"
+)
+
+// ID provides a type narrowed representation of the unique identifier of a unit.
+type ID string
+
+// Unit represents a point-in-time snapshot of a vertex in the dependency graph.
+// Units may depend on other units, or be depended on by other units. The unit struct
+// is not aware of updates made to the dependency graph after it is initialized and should
+// not be cached.
+type Unit struct {
+	id     ID
+	status Status
+	// ready is true if all dependencies are satisfied.
+	// It does not have an accessor method on Unit, because a unit cannot know whether it is ready.
+	// Only the Manager can calculate whether a unit is ready based on knowledge of the dependency graph.
+	// To discourage use of an outdated readiness value, only the Manager should set and return this field.
+	ready bool
+}
+
+func (u Unit) ID() ID {
+	return u.id
+}
+
+func (u Unit) Status() Status {
+	return u.status
+}
+
+// Dependency represents a dependency relationship between units.
+type Dependency struct {
+	Unit           ID
+	DependsOn      ID
+	RequiredStatus Status
+	CurrentStatus  Status
 	IsSatisfied    bool
 }

 // Manager provides reactive dependency tracking over a Graph.
-// It manages consumer registration, dependency relationships, and status updates
+// It manages Unit registration, dependency relationships, and status updates
 // with automatic recalculation of readiness when dependencies are satisfied.
-type Manager[StatusType, ConsumerID comparable] struct {
+type Manager struct {
 	mu sync.RWMutex

 	// The underlying graph that stores dependency relationships
-	graph *Graph[StatusType, *dependencyVertex[ConsumerID]]
+	graph *Graph[Status, ID]

-	// Track current status of each consumer
-	consumerStatus map[ConsumerID]StatusType
-
-	// Track readiness state (cached to avoid repeated graph traversal)
-	consumerReadiness map[ConsumerID]bool
-
-	// Track which consumers are registered
-	registeredConsumers map[ConsumerID]bool
-
-	// Store vertex instances for each consumer to ensure consistent references
-	consumerVertices map[ConsumerID]*dependencyVertex[ConsumerID]
+	// Store vertex instances for each unit to ensure consistent references
+	units map[ID]Unit
 }

 // NewManager creates a new Manager instance.
-func NewManager[StatusType, ConsumerID comparable]() *Manager[StatusType, ConsumerID] {
-	return &Manager[StatusType, ConsumerID]{
-		graph:               &Graph[StatusType, *dependencyVertex[ConsumerID]]{},
-		consumerStatus:      make(map[ConsumerID]StatusType),
-		consumerReadiness:   make(map[ConsumerID]bool),
-		registeredConsumers: make(map[ConsumerID]bool),
-		consumerVertices:    make(map[ConsumerID]*dependencyVertex[ConsumerID]),
+func NewManager() *Manager {
+	return &Manager{
+		graph: &Graph[Status, ID]{},
+		units: make(map[ID]Unit),
 	}
 }

-// Register registers a new consumer as a vertex in the dependency graph.
-func (dt *Manager[StatusType, ConsumerID]) Register(id ConsumerID) error {
-	dt.mu.Lock()
-	defer dt.mu.Unlock()
+// Register adds a unit to the manager if it is not already registered.
+// If a Unit is already registered (per the ID field), it is not updated.
+func (m *Manager) Register(id ID) error {
+	m.mu.Lock()
+	defer m.mu.Unlock()

-	if dt.registeredConsumers[id] {
-		return ErrConsumerAlreadyRegistered
+	if id == "" {
+		return xerrors.Errorf("registering unit %q: %w", id, ErrUnitIDRequired)
 	}

-	// Create and store the vertex for this consumer
-	vertex := &dependencyVertex[ConsumerID]{ID: id}
-	dt.consumerVertices[id] = vertex
-	dt.registeredConsumers[id] = true
-	dt.consumerReadiness[id] = true // New consumers start as ready (no dependencies)
+	if m.registered(id) {
+		return xerrors.Errorf("registering unit %q: %w", id, ErrUnitAlreadyRegistered)
+	}
+
+	m.units[id] = Unit{
+		id:     id,
+		status: StatusPending,
+		ready:  true,
+	}

 	return nil
 }

-// AddDependency adds a dependency relationship between consumers.
-// The consumer depends on the dependsOn consumer reaching the requiredStatus.
-func (dt *Manager[StatusType, ConsumerID]) AddDependency(consumer ConsumerID, dependsOn ConsumerID, requiredStatus StatusType) error {
-	dt.mu.Lock()
-	defer dt.mu.Unlock()
+// registered checks if a unit is registered in the manager.
+func (m *Manager) registered(id ID) bool {
+	return m.units[id].status != StatusNotRegistered
+}

-	if !dt.registeredConsumers[consumer] {
-		return xerrors.Errorf("consumer %v is not registered", consumer)
-	}
-	if !dt.registeredConsumers[dependsOn] {
-		return xerrors.Errorf("consumer %v is not registered", dependsOn)
+// Unit fetches a unit from the manager. If the unit does not exist,
+// it returns the Unit zero-value as a placeholder unit, because
+// units may depend on other units that have not yet been created.
+func (m *Manager) Unit(id ID) (Unit, error) {
+	if id == "" {
+		return Unit{}, xerrors.Errorf("unit ID cannot be empty: %w", ErrUnitIDRequired)
 	}

-	// Get the stored vertices for both consumers
-	consumerVertex := dt.consumerVertices[consumer]
-	dependsOnVertex := dt.consumerVertices[dependsOn]
+	m.mu.RLock()
+	defer m.mu.RUnlock()
+
+	return m.units[id], nil
+}
+
+func (m *Manager) IsReady(id ID) (bool, error) {
+	if id == "" {
+		return false, xerrors.Errorf("unit ID cannot be empty: %w", ErrUnitIDRequired)
+	}
+
+	m.mu.RLock()
+	defer m.mu.RUnlock()
+
+	if !m.registered(id) {
+		return true, nil
+	}
+
+	return m.units[id].ready, nil
+}
+
+// AddDependency adds a dependency relationship between units.
+// The unit depends on the dependsOn unit reaching the requiredStatus.
+func (m *Manager) AddDependency(unit ID, dependsOn ID, requiredStatus Status) error {
+	m.mu.Lock()
+	defer m.mu.Unlock()
+
+	switch {
+	case unit == "":
+		return xerrors.Errorf("dependent name cannot be empty: %w", ErrUnitIDRequired)
+	case dependsOn == "":
+		return xerrors.Errorf("dependency name cannot be empty: %w", ErrUnitIDRequired)
+	case !m.registered(unit):
+		return xerrors.Errorf("dependent unit %q must be registered first: %w", unit, ErrUnitNotFound)
+	}

 	// Add the dependency edge to the graph
-	// The edge goes from consumer to dependsOn, representing the dependency
-	err := dt.graph.AddEdge(consumerVertex, dependsOnVertex, requiredStatus)
+	// The edge goes from unit to dependsOn, representing the dependency
+	err := m.graph.AddEdge(unit, dependsOn, requiredStatus)
 	if err != nil {
-		return xerrors.Errorf("failed to add dependency: %w", err)
+		return xerrors.Errorf("adding edge for unit %q: %w", unit, errors.Join(ErrFailedToAddDependency, err))
 	}

-	// Recalculate readiness for the consumer since it now has a dependency
-	dt.recalculateReadinessUnsafe(consumer)
+	// Recalculate readiness for the unit since it now has a new dependency
+	m.recalculateReadinessUnsafe(unit)

 	return nil
 }

-// UpdateStatus updates a consumer's status and recalculates readiness for affected dependents.
-func (dt *Manager[StatusType, ConsumerID]) UpdateStatus(consumer ConsumerID, newStatus StatusType) error {
-	dt.mu.Lock()
-	defer dt.mu.Unlock()
+// UpdateStatus updates a unit's status and recalculates readiness for affected dependents.
+func (m *Manager) UpdateStatus(unit ID, newStatus Status) error {
+	m.mu.Lock()
+	defer m.mu.Unlock()

-	if !dt.registeredConsumers[consumer] {
-		return ErrConsumerNotFound
+	switch {
+	case unit == "":
+		return xerrors.Errorf("updating status for unit %q: %w", unit, ErrUnitIDRequired)
+	case !m.registered(unit):
+		return xerrors.Errorf("unit %q must be registered first: %w", unit, ErrUnitNotFound)
 	}

-	// Update the consumer's status
-	if dt.consumerStatus[consumer] == newStatus {
-		return ErrSameStatusAlreadySet
+	u := m.units[unit]
+	if u.status == newStatus {
+		return xerrors.Errorf("checking status for unit %q: %w", unit, ErrSameStatusAlreadySet)
 	}
-	dt.consumerStatus[consumer] = newStatus

-	// Get all consumers that depend on this one (reverse adjacent vertices)
-	consumerVertex := dt.consumerVertices[consumer]
-	dependentEdges := dt.graph.GetReverseAdjacentVertices(consumerVertex)
+	u.status = newStatus
+	m.units[unit] = u
+
+	// Get all units that depend on this one (reverse adjacent vertices)
+	dependents := m.graph.GetReverseAdjacentVertices(unit)

 	// Recalculate readiness for all dependents
-	for _, edge := range dependentEdges {
-		dt.recalculateReadinessUnsafe(edge.From.ID)
+	for _, dependent := range dependents {
+		m.recalculateReadinessUnsafe(dependent.From)
 	}

 	return nil
 }

-// IsReady checks if all dependencies for a consumer are satisfied.
-func (dt *Manager[StatusType, ConsumerID]) IsReady(consumer ConsumerID) (bool, error) {
-	dt.mu.RLock()
-	defer dt.mu.RUnlock()
-
-	if !dt.registeredConsumers[consumer] {
-		return false, ErrConsumerNotFound
-	}
-
-	return dt.consumerReadiness[consumer], nil
-}
-
-// GetUnmetDependencies returns a list of unsatisfied dependencies for a consumer.
-func (dt *Manager[StatusType, ConsumerID]) GetUnmetDependencies(consumer ConsumerID) ([]Dependency[StatusType, ConsumerID], error) {
-	dt.mu.RLock()
-	defer dt.mu.RUnlock()
-
-	if !dt.registeredConsumers[consumer] {
-		return nil, ErrConsumerNotFound
-	}
-
-	consumerVertex := dt.consumerVertices[consumer]
-	forwardEdges := dt.graph.GetForwardAdjacentVertices(consumerVertex)
-
-	var unmetDependencies []Dependency[StatusType, ConsumerID]
-
-	for _, edge := range forwardEdges {
-		dependsOnConsumer := edge.To.ID
-		requiredStatus := edge.Edge
-		currentStatus, exists := dt.consumerStatus[dependsOnConsumer]
-		if !exists {
-			// If the dependency consumer has no status, it's not satisfied
-			var zeroStatus StatusType
-			unmetDependencies = append(unmetDependencies, Dependency[StatusType, ConsumerID]{
-				Consumer:       consumer,
-				DependsOn:      dependsOnConsumer,
-				RequiredStatus: requiredStatus,
-				CurrentStatus:  zeroStatus, // Zero value
-				IsSatisfied:    false,
-			})
-		} else {
-			isSatisfied := currentStatus == requiredStatus
-			if !isSatisfied {
-				unmetDependencies = append(unmetDependencies, Dependency[StatusType, ConsumerID]{
-					Consumer:       consumer,
-					DependsOn:      dependsOnConsumer,
-					RequiredStatus: requiredStatus,
-					CurrentStatus:  currentStatus,
-					IsSatisfied:    false,
-				})
-			}
-		}
-	}
-
-	return unmetDependencies, nil
-}
-
-// recalculateReadinessUnsafe recalculates the readiness state for a consumer.
+// recalculateReadinessUnsafe recalculates the readiness state for a unit.
 // This method assumes the caller holds the write lock.
-func (dt *Manager[StatusType, ConsumerID]) recalculateReadinessUnsafe(consumer ConsumerID) {
-	consumerVertex := dt.consumerVertices[consumer]
-	forwardEdges := dt.graph.GetForwardAdjacentVertices(consumerVertex)
+func (m *Manager) recalculateReadinessUnsafe(unit ID) {
+	u := m.units[unit]
+	dependencies := m.graph.GetForwardAdjacentVertices(unit)

-	// If there are no dependencies, the consumer is ready
-	if len(forwardEdges) == 0 {
-		dt.consumerReadiness[consumer] = true
-		return
-	}
-
-	// Check if all dependencies are satisfied
 	allSatisfied := true
-	for _, edge := range forwardEdges {
-		dependsOnConsumer := edge.To.ID
-		requiredStatus := edge.Edge
-		currentStatus, exists := dt.consumerStatus[dependsOnConsumer]
-		if !exists || currentStatus != requiredStatus {
+	for _, dependency := range dependencies {
+		requiredStatus := dependency.Edge
+		dependsOnUnit := m.units[dependency.To]
+		if dependsOnUnit.status != requiredStatus {
 			allSatisfied = false
 			break
 		}
 	}

-	dt.consumerReadiness[consumer] = allSatisfied
+	u.ready = allSatisfied
+	m.units[unit] = u
 }

 // GetGraph returns the underlying graph for visualization and debugging.
 // This should be used carefully as it exposes the internal graph structure.
-func (dt *Manager[StatusType, ConsumerID]) GetGraph() *Graph[StatusType, *dependencyVertex[ConsumerID]] {
-	return dt.graph
+func (m *Manager) GetGraph() *Graph[Status, ID] {
+	return m.graph
 }

-// GetStatus returns the current status of a consumer.
-func (dt *Manager[StatusType, ConsumerID]) GetStatus(consumer ConsumerID) (StatusType, error) {
-	dt.mu.RLock()
-	defer dt.mu.RUnlock()
+// GetAllDependencies returns all dependencies for a unit, both satisfied and unsatisfied.
+func (m *Manager) GetAllDependencies(unit ID) ([]Dependency, error) {
+	m.mu.RLock()
+	defer m.mu.RUnlock()

-	if !dt.registeredConsumers[consumer] {
-		var zeroStatus StatusType
-		return zeroStatus, ErrConsumerNotFound
+	if unit == "" {
+		return nil, xerrors.Errorf("unit ID cannot be empty: %w", ErrUnitIDRequired)
 	}

-	status, exists := dt.consumerStatus[consumer]
-	if !exists {
-		var zeroStatus StatusType
-		return zeroStatus, nil
+	if !m.registered(unit) {
+		return nil, xerrors.Errorf("checking registration for unit %q: %w", unit, ErrUnitNotFound)
 	}

-	return status, nil
-}
+	dependencies := m.graph.GetForwardAdjacentVertices(unit)

-// GetAllDependencies returns all dependencies for a consumer, both satisfied and unsatisfied.
-func (dt *Manager[StatusType, ConsumerID]) GetAllDependencies(consumer ConsumerID) ([]Dependency[StatusType, ConsumerID], error) {
-	dt.mu.RLock()
-	defer dt.mu.RUnlock()
+	var allDependencies []Dependency

-	if !dt.registeredConsumers[consumer] {
-		return nil, ErrConsumerNotFound
-	}
-
-	consumerVertex := dt.consumerVertices[consumer]
-	forwardEdges := dt.graph.GetForwardAdjacentVertices(consumerVertex)
-
-	var allDependencies []Dependency[StatusType, ConsumerID]
-
-	for _, edge := range forwardEdges {
-		dependsOnConsumer := edge.To.ID
-		requiredStatus := edge.Edge
-		currentStatus, exists := dt.consumerStatus[dependsOnConsumer]
-		if !exists {
-			// If the dependency consumer has no status, it's not satisfied
-			var zeroStatus StatusType
-			allDependencies = append(allDependencies, Dependency[StatusType, ConsumerID]{
-				Consumer:       consumer,
-				DependsOn:      dependsOnConsumer,
-				RequiredStatus: requiredStatus,
-				CurrentStatus:  zeroStatus, // Zero value
-				IsSatisfied:    false,
-			})
-		} else {
-			isSatisfied := currentStatus == requiredStatus
-			allDependencies = append(allDependencies, Dependency[StatusType, ConsumerID]{
-				Consumer:       consumer,
-				DependsOn:      dependsOnConsumer,
-				RequiredStatus: requiredStatus,
-				CurrentStatus:  currentStatus,
-				IsSatisfied:    isSatisfied,
-			})
-		}
+	for _, dependency := range dependencies {
+		dependsOnUnit := m.units[dependency.To]
+		requiredStatus := dependency.Edge
+		allDependencies = append(allDependencies, Dependency{
+			Unit:           unit,
+			DependsOn:      dependency.To,
+			RequiredStatus: requiredStatus,
+			CurrentStatus:  dependsOnUnit.status,
+			IsSatisfied:    dependsOnUnit.status == requiredStatus,
+		})
 	}

 	return allDependencies, nil
 }

-// ExportDOT exports the dependency graph to DOT format for visualization.
-func (dt *Manager[StatusType, ConsumerID]) ExportDOT(name string) (string, error) {
-	return dt.graph.ToDOT(name)
+// GetUnmetDependencies returns a list of unsatisfied dependencies for a unit.
+func (m *Manager) GetUnmetDependencies(unit ID) ([]Dependency, error) {
+	allDependencies, err := m.GetAllDependencies(unit)
+	if err != nil {
+		return nil, err
+	}
+
+	var unmetDependencies []Dependency = slice.Filter(allDependencies, func(dependency Dependency) bool {
+		return !dependency.IsSatisfied
+	})
+
+	return unmetDependencies, nil
+}
+
+// ExportDOT exports the dependency graph to DOT format for visualization.
+func (m *Manager) ExportDOT(name string) (string, error) {
+	return m.graph.ToDOT(name)
 }
@@ -11,6 +11,7 @@ import (
 	"os"
 	"path/filepath"
 	"runtime"
+	"slices"
 	"strconv"
 	"strings"
 	"time"
@@ -56,6 +57,7 @@ func workspaceAgent() *serpent.Command {
 		devcontainers                  bool
 		devcontainerProjectDiscovery   bool
 		devcontainerDiscoveryAutostart bool
+		socketServerEnabled            bool
 		socketPath                     string
 	)
 	agentAuth := &AgentAuth{}
@@ -202,18 +204,15 @@ func workspaceAgent() *serpent.Command {
 			// Enable pprof handler
 			// This prevents the pprof import from being accidentally deleted.
 			_ = pprof.Handler
-			pprofSrvClose := ServeHandler(ctx, logger, nil, pprofAddress, "pprof")
-			defer pprofSrvClose()
-			if port, err := extractPort(pprofAddress); err == nil {
-				ignorePorts[port] = "pprof"
-			}
+			if pprofAddress != "" {
+				pprofSrvClose := ServeHandler(ctx, logger, nil, pprofAddress, "pprof")
+				defer pprofSrvClose()

-			if port, err := extractPort(prometheusAddress); err == nil {
-				ignorePorts[port] = "prometheus"
-			}
-
-			if port, err := extractPort(debugAddress); err == nil {
-				ignorePorts[port] = "debug"
+				if port, err := extractPort(pprofAddress); err == nil {
+					ignorePorts[port] = "pprof"
+				}
+			} else {
+				logger.Debug(ctx, "pprof address is empty, disabling pprof server")
 			}

 			executablePath, err := os.Executable()
@@ -277,6 +276,28 @@ func workspaceAgent() *serpent.Command {
 			for {
 				prometheusRegistry := prometheus.NewRegistry()

+				promHandler := agent.PrometheusMetricsHandler(prometheusRegistry, logger)
+				var serverClose []func()
+				if prometheusAddress != "" {
+					prometheusSrvClose := ServeHandler(ctx, logger, promHandler, prometheusAddress, "prometheus")
+					serverClose = append(serverClose, prometheusSrvClose)
+
+					if port, err := extractPort(prometheusAddress); err == nil {
+						ignorePorts[port] = "prometheus"
+					}
+				} else {
+					logger.Debug(ctx, "prometheus address is empty, disabling prometheus server")
+				}
+
+				if debugAddress != "" {
+					// ServerHandle depends on `agnt.HTTPDebug()`, but `agnt`
+					// depends on `ignorePorts`. Keep this if statement in sync
+					// with below.
+					if port, err := extractPort(debugAddress); err == nil {
+						ignorePorts[port] = "debug"
+					}
+				}
+
 				agnt := agent.New(agent.Options{
 					Client:        client,
 					Logger:        logger,
@@ -298,13 +319,19 @@ func workspaceAgent() *serpent.Command {
 						agentcontainers.WithProjectDiscovery(devcontainerProjectDiscovery),
 						agentcontainers.WithDiscoveryAutostart(devcontainerDiscoveryAutostart),
 					},
-					SocketPath: socketPath,
+					SocketPath:          socketPath,
+					SocketServerEnabled: socketServerEnabled,
 				})

-				promHandler := agent.PrometheusMetricsHandler(prometheusRegistry, logger)
-				prometheusSrvClose := ServeHandler(ctx, logger, promHandler, prometheusAddress, "prometheus")
-
-				debugSrvClose := ServeHandler(ctx, logger, agnt.HTTPDebug(), debugAddress, "debug")
+				if debugAddress != "" {
+					// ServerHandle depends on `agnt.HTTPDebug()`, but `agnt`
+					// depends on `ignorePorts`. Keep this if statement in sync
+					// with above.
+					debugSrvClose := ServeHandler(ctx, logger, agnt.HTTPDebug(), debugAddress, "debug")
+					serverClose = append(serverClose, debugSrvClose)
+				} else {
+					logger.Debug(ctx, "debug address is empty, disabling debug server")
+				}

 				select {
 				case <-ctx.Done():
@@ -316,8 +343,11 @@ func workspaceAgent() *serpent.Command {
 				}

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

 				if mustExit {
 					break
@@ -451,6 +481,13 @@ 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",
@@ -178,6 +178,51 @@ func TestWorkspaceAgent(t *testing.T) {
 		require.Greater(t, atomic.LoadInt64(&called), int64(0), "expected coderd to be reached with custom headers")
 		require.Greater(t, atomic.LoadInt64(&derpCalled), int64(0), "expected /derp to be called with custom headers")
 	})
+
+	t.Run("DisabledServers", func(t *testing.T) {
+		t.Parallel()
+
+		client, db := coderdtest.NewWithDatabase(t, nil)
+		user := coderdtest.CreateFirstUser(t, client)
+		r := dbfake.WorkspaceBuild(t, db, database.WorkspaceTable{
+			OrganizationID: user.OrganizationID,
+			OwnerID:        user.UserID,
+		}).WithAgent().Do()
+
+		logDir := t.TempDir()
+		inv, _ := clitest.New(t,
+			"agent",
+			"--auth", "token",
+			"--agent-token", r.AgentToken,
+			"--agent-url", client.URL.String(),
+			"--log-dir", logDir,
+			"--pprof-address", "",
+			"--prometheus-address", "",
+			"--debug-address", "",
+		)
+
+		clitest.Start(t, inv)
+
+		// Verify the agent is connected and working.
+		resources := coderdtest.NewWorkspaceAgentWaiter(t, client, r.Workspace.ID).
+			MatchResources(matchAgentWithVersion).Wait()
+		require.Len(t, resources, 1)
+		require.Len(t, resources[0].Agents, 1)
+		require.NotEmpty(t, resources[0].Agents[0].Version)
+
+		// Verify the servers are not listening by checking the log for disabled
+		// messages.
+		require.Eventually(t, func() bool {
+			logContent, err := os.ReadFile(filepath.Join(logDir, "coder-agent.log"))
+			if err != nil {
+				return false
+			}
+			logStr := string(logContent)
+			return strings.Contains(logStr, "pprof address is empty, disabling pprof server") &&
+				strings.Contains(logStr, "prometheus address is empty, disabling prometheus server") &&
+				strings.Contains(logStr, "debug address is empty, disabling debug server")
+		}, testutil.WaitLong, testutil.IntervalMedium)
+	})
 }

 func matchAgentWithVersion(rs []codersdk.WorkspaceResource) bool {
@@ -0,0 +1,78 @@
+package cli
+
+import (
+	"encoding/csv"
+	"strings"
+
+	"github.com/spf13/pflag"
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/codersdk"
+)
+
+var (
+	_ pflag.SliceValue = &AllowListFlag{}
+	_ pflag.Value      = &AllowListFlag{}
+)
+
+// AllowListFlag implements pflag.SliceValue for codersdk.APIAllowListTarget entries.
+type AllowListFlag []codersdk.APIAllowListTarget
+
+func AllowListFlagOf(al *[]codersdk.APIAllowListTarget) *AllowListFlag {
+	return (*AllowListFlag)(al)
+}
+
+func (a AllowListFlag) String() string {
+	return strings.Join(a.GetSlice(), ",")
+}
+
+func (a AllowListFlag) Value() []codersdk.APIAllowListTarget {
+	return []codersdk.APIAllowListTarget(a)
+}
+
+func (AllowListFlag) Type() string { return "allow-list" }
+
+func (a *AllowListFlag) Set(set string) error {
+	values, err := csv.NewReader(strings.NewReader(set)).Read()
+	if err != nil {
+		return xerrors.Errorf("parse allow list entries as csv: %w", err)
+	}
+	for _, v := range values {
+		if err := a.Append(v); err != nil {
+			return err
+		}
+	}
+	return nil
+}
+
+func (a *AllowListFlag) Append(value string) error {
+	value = strings.TrimSpace(value)
+	if value == "" {
+		return xerrors.New("allow list entry cannot be empty")
+	}
+	var target codersdk.APIAllowListTarget
+	if err := target.UnmarshalText([]byte(value)); err != nil {
+		return err
+	}
+
+	*a = append(*a, target)
+	return nil
+}
+
+func (a *AllowListFlag) Replace(items []string) error {
+	*a = []codersdk.APIAllowListTarget{}
+	for _, item := range items {
+		if err := a.Append(item); err != nil {
+			return err
+		}
+	}
+	return nil
+}
+
+func (a *AllowListFlag) GetSlice() []string {
+	out := make([]string, len(*a))
+	for i, entry := range *a {
+		out[i] = entry.String()
+	}
+	return out
+}
@@ -28,7 +28,9 @@ import (
 )

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

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

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

 // SetupConfig applies the URL and SessionToken of the client to the config.
@@ -577,53 +577,57 @@ func prepWorkspaceBuild(inv *serpent.Invocation, client *codersdk.Client, args p
 		return nil, xerrors.Errorf("template version git auth: %w", err)
 	}

-	// Run a dry-run with the given parameters to check correctness
-	dryRun, err := client.CreateTemplateVersionDryRun(inv.Context(), templateVersion.ID, codersdk.CreateTemplateVersionDryRunRequest{
-		WorkspaceName:       args.NewWorkspaceName,
-		RichParameterValues: buildParameters,
-	})
-	if err != nil {
-		return nil, xerrors.Errorf("begin workspace dry-run: %w", err)
-	}
+	// Only perform dry-run for workspace creation and updates
+	// Skip for start and restart to avoid unnecessary delays
+	if args.Action == WorkspaceCreate || args.Action == WorkspaceUpdate {
+		// Run a dry-run with the given parameters to check correctness
+		dryRun, err := client.CreateTemplateVersionDryRun(inv.Context(), templateVersion.ID, codersdk.CreateTemplateVersionDryRunRequest{
+			WorkspaceName:       args.NewWorkspaceName,
+			RichParameterValues: buildParameters,
+		})
+		if err != nil {
+			return nil, xerrors.Errorf("begin workspace dry-run: %w", err)
+		}

-	matchedProvisioners, err := client.TemplateVersionDryRunMatchedProvisioners(inv.Context(), templateVersion.ID, dryRun.ID)
-	if err != nil {
-		return nil, xerrors.Errorf("get matched provisioners: %w", err)
-	}
-	cliutil.WarnMatchedProvisioners(inv.Stdout, &matchedProvisioners, dryRun)
-	_, _ = fmt.Fprintln(inv.Stdout, "Planning workspace...")
-	err = cliui.ProvisionerJob(inv.Context(), inv.Stdout, cliui.ProvisionerJobOptions{
-		Fetch: func() (codersdk.ProvisionerJob, error) {
-			return client.TemplateVersionDryRun(inv.Context(), templateVersion.ID, dryRun.ID)
-		},
-		Cancel: func() error {
-			return client.CancelTemplateVersionDryRun(inv.Context(), templateVersion.ID, dryRun.ID)
-		},
-		Logs: func() (<-chan codersdk.ProvisionerJobLog, io.Closer, error) {
-			return client.TemplateVersionDryRunLogsAfter(inv.Context(), templateVersion.ID, dryRun.ID, 0)
-		},
-		// Don't show log output for the dry-run unless there's an error.
-		Silent: true,
-	})
-	if err != nil {
-		// TODO (Dean): reprompt for parameter values if we deem it to
-		// be a validation error
-		return nil, xerrors.Errorf("dry-run workspace: %w", err)
-	}
+		matchedProvisioners, err := client.TemplateVersionDryRunMatchedProvisioners(inv.Context(), templateVersion.ID, dryRun.ID)
+		if err != nil {
+			return nil, xerrors.Errorf("get matched provisioners: %w", err)
+		}
+		cliutil.WarnMatchedProvisioners(inv.Stdout, &matchedProvisioners, dryRun)
+		_, _ = fmt.Fprintln(inv.Stdout, "Planning workspace...")
+		err = cliui.ProvisionerJob(inv.Context(), inv.Stdout, cliui.ProvisionerJobOptions{
+			Fetch: func() (codersdk.ProvisionerJob, error) {
+				return client.TemplateVersionDryRun(inv.Context(), templateVersion.ID, dryRun.ID)
+			},
+			Cancel: func() error {
+				return client.CancelTemplateVersionDryRun(inv.Context(), templateVersion.ID, dryRun.ID)
+			},
+			Logs: func() (<-chan codersdk.ProvisionerJobLog, io.Closer, error) {
+				return client.TemplateVersionDryRunLogsAfter(inv.Context(), templateVersion.ID, dryRun.ID, 0)
+			},
+			// Don't show log output for the dry-run unless there's an error.
+			Silent: true,
+		})
+		if err != nil {
+			// TODO (Dean): reprompt for parameter values if we deem it to
+			// be a validation error
+			return nil, xerrors.Errorf("dry-run workspace: %w", err)
+		}

-	resources, err := client.TemplateVersionDryRunResources(inv.Context(), templateVersion.ID, dryRun.ID)
-	if err != nil {
-		return nil, xerrors.Errorf("get workspace dry-run resources: %w", err)
-	}
+		resources, err := client.TemplateVersionDryRunResources(inv.Context(), templateVersion.ID, dryRun.ID)
+		if err != nil {
+			return nil, xerrors.Errorf("get workspace dry-run resources: %w", err)
+		}

-	err = cliui.WorkspaceResources(inv.Stdout, resources, cliui.WorkspaceResourcesOptions{
-		WorkspaceName: args.NewWorkspaceName,
-		// Since agents haven't connected yet, hiding this makes more sense.
-		HideAgentState: true,
-		Title:          "Workspace Preview",
-	})
-	if err != nil {
-		return nil, xerrors.Errorf("get resources: %w", err)
+		err = cliui.WorkspaceResources(inv.Stdout, resources, cliui.WorkspaceResourcesOptions{
+			WorkspaceName: args.NewWorkspaceName,
+			// Since agents haven't connected yet, hiding this makes more sense.
+			HideAgentState: true,
+			Title:          "Workspace Preview",
+		})
+		if err != nil {
+			return nil, xerrors.Errorf("get resources: %w", err)
+		}
 	}

 	return buildParameters, nil
@@ -64,7 +64,9 @@ func (r *RootCmd) scaletestCmd() *serpent.Command {
 			r.scaletestWorkspaceTraffic(),
 			r.scaletestAutostart(),
 			r.scaletestNotifications(),
+			r.scaletestTaskStatus(),
 			r.scaletestSMTP(),
+			r.scaletestPrebuilds(),
 		},
 	}

@@ -384,6 +386,88 @@ func (s *scaletestPrometheusFlags) attach(opts *serpent.OptionSet) {
 	)
 }

+// workspaceTargetFlags holds common flags for targeting specific workspaces in scale tests.
+type workspaceTargetFlags struct {
+	template         string
+	targetWorkspaces string
+	useHostLogin     bool
+}
+
+// attach adds the workspace target flags to the given options set.
+func (f *workspaceTargetFlags) attach(opts *serpent.OptionSet) {
+	*opts = append(*opts,
+		serpent.Option{
+			Flag:          "template",
+			FlagShorthand: "t",
+			Env:           "CODER_SCALETEST_TEMPLATE",
+			Description:   "Name or ID of the template. Traffic generation will be limited to workspaces created from this template.",
+			Value:         serpent.StringOf(&f.template),
+		},
+		serpent.Option{
+			Flag:        "target-workspaces",
+			Env:         "CODER_SCALETEST_TARGET_WORKSPACES",
+			Description: "Target a specific range of workspaces in the format [START]:[END] (exclusive). Example: 0:10 will target the 10 first alphabetically sorted workspaces (0-9).",
+			Value:       serpent.StringOf(&f.targetWorkspaces),
+		},
+		serpent.Option{
+			Flag:        "use-host-login",
+			Env:         "CODER_SCALETEST_USE_HOST_LOGIN",
+			Default:     "false",
+			Description: "Connect as the currently logged in user.",
+			Value:       serpent.BoolOf(&f.useHostLogin),
+		},
+	)
+}
+
+// getTargetedWorkspaces retrieves the workspaces based on the template filter and target range. warnWriter is where to
+// write a warning message if any workspaces were skipped due to ownership mismatch.
+func (f *workspaceTargetFlags) getTargetedWorkspaces(ctx context.Context, client *codersdk.Client, organizationIDs []uuid.UUID, warnWriter io.Writer) ([]codersdk.Workspace, error) {
+	// Validate template if provided
+	if f.template != "" {
+		_, err := parseTemplate(ctx, client, organizationIDs, f.template)
+		if err != nil {
+			return nil, xerrors.Errorf("parse template: %w", err)
+		}
+	}
+
+	// Parse target range
+	targetStart, targetEnd, err := parseTargetRange("workspaces", f.targetWorkspaces)
+	if err != nil {
+		return nil, xerrors.Errorf("parse target workspaces: %w", err)
+	}
+
+	// Determine owner based on useHostLogin
+	var owner string
+	if f.useHostLogin {
+		owner = codersdk.Me
+	}
+
+	// Get workspaces
+	workspaces, numSkipped, err := getScaletestWorkspaces(ctx, client, owner, f.template)
+	if err != nil {
+		return nil, err
+	}
+	if numSkipped > 0 {
+		cliui.Warnf(warnWriter, "CODER_DISABLE_OWNER_WORKSPACE_ACCESS is set on the deployment.\n\t%d workspace(s) were skipped due to ownership mismatch.\n\tSet --use-host-login to only target workspaces you own.", numSkipped)
+	}
+
+	// Adjust targetEnd if not specified
+	if targetEnd == 0 {
+		targetEnd = len(workspaces)
+	}
+
+	// Validate range
+	if len(workspaces) == 0 {
+		return nil, xerrors.Errorf("no scaletest workspaces exist")
+	}
+	if targetEnd > len(workspaces) {
+		return nil, xerrors.Errorf("target workspace end %d is greater than the number of workspaces %d", targetEnd, len(workspaces))
+	}
+
+	// Return the sliced workspaces
+	return workspaces[targetStart:targetEnd], nil
+}
+
 func requireAdmin(ctx context.Context, client *codersdk.Client) (codersdk.User, error) {
 	me, err := client.User(ctx, codersdk.Me)
 	if err != nil {
@@ -1193,12 +1277,10 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *serpent.Command {
 		bytesPerTick      int64
 		ssh               bool
 		disableDirect     bool
-		useHostLogin      bool
 		app               string
-		template          string
-		targetWorkspaces  string
 		workspaceProxyURL string

+		targetFlags     = &workspaceTargetFlags{}
 		tracingFlags    = &scaletestTracingFlags{}
 		strategy        = &scaletestStrategyFlags{}
 		cleanupStrategy = newScaletestCleanupStrategy()
@@ -1243,15 +1325,9 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *serpent.Command {
 				},
 			}

-			if template != "" {
-				_, err := parseTemplate(ctx, client, me.OrganizationIDs, template)
-				if err != nil {
-					return xerrors.Errorf("parse template: %w", err)
-				}
-			}
-			targetWorkspaceStart, targetWorkspaceEnd, err := parseTargetRange("workspaces", targetWorkspaces)
+			workspaces, err := targetFlags.getTargetedWorkspaces(ctx, client, me.OrganizationIDs, inv.Stdout)
 			if err != nil {
-				return xerrors.Errorf("parse target workspaces: %w", err)
+				return err
 			}

 			appHost, err := client.AppHost(ctx)
@@ -1259,30 +1335,6 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *serpent.Command {
 				return xerrors.Errorf("get app host: %w", err)
 			}

-			var owner string
-			if useHostLogin {
-				owner = codersdk.Me
-			}
-
-			workspaces, numSkipped, err := getScaletestWorkspaces(inv.Context(), client, owner, template)
-			if err != nil {
-				return err
-			}
-			if numSkipped > 0 {
-				cliui.Warnf(inv.Stdout, "CODER_DISABLE_OWNER_WORKSPACE_ACCESS is set on the deployment.\n\t%d workspace(s) were skipped due to ownership mismatch.\n\tSet --use-host-login to only target workspaces you own.", numSkipped)
-			}
-
-			if targetWorkspaceEnd == 0 {
-				targetWorkspaceEnd = len(workspaces)
-			}
-
-			if len(workspaces) == 0 {
-				return xerrors.Errorf("no scaletest workspaces exist")
-			}
-			if targetWorkspaceEnd > len(workspaces) {
-				return xerrors.Errorf("target workspace end %d is greater than the number of workspaces %d", targetWorkspaceEnd, len(workspaces))
-			}
-
 			tracerProvider, closeTracing, tracingEnabled, err := tracingFlags.provider(ctx)
 			if err != nil {
 				return xerrors.Errorf("create tracer provider: %w", err)
@@ -1307,10 +1359,6 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *serpent.Command {

 			th := harness.NewTestHarness(strategy.toStrategy(), cleanupStrategy.toStrategy())
 			for idx, ws := range workspaces {
-				if idx < targetWorkspaceStart || idx >= targetWorkspaceEnd {
-					continue
-				}
-
 				var (
 					agent codersdk.WorkspaceAgent
 					name  = "workspace-traffic"
@@ -1415,19 +1463,6 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *serpent.Command {
 	}

 	cmd.Options = []serpent.Option{
-		{
-			Flag:          "template",
-			FlagShorthand: "t",
-			Env:           "CODER_SCALETEST_TEMPLATE",
-			Description:   "Name or ID of the template. Traffic generation will be limited to workspaces created from this template.",
-			Value:         serpent.StringOf(&template),
-		},
-		{
-			Flag:        "target-workspaces",
-			Env:         "CODER_SCALETEST_TARGET_WORKSPACES",
-			Description: "Target a specific range of workspaces in the format [START]:[END] (exclusive). Example: 0:10 will target the 10 first alphabetically sorted workspaces (0-9).",
-			Value:       serpent.StringOf(&targetWorkspaces),
-		},
 		{
 			Flag:        "bytes-per-tick",
 			Env:         "CODER_SCALETEST_WORKSPACE_TRAFFIC_BYTES_PER_TICK",
@@ -1463,13 +1498,6 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *serpent.Command {
 			Description: "Send WebSocket traffic to a workspace app (proxied via coderd), cannot be used with --ssh.",
 			Value:       serpent.StringOf(&app),
 		},
-		{
-			Flag:        "use-host-login",
-			Env:         "CODER_SCALETEST_USE_HOST_LOGIN",
-			Default:     "false",
-			Description: "Connect as the currently logged in user.",
-			Value:       serpent.BoolOf(&useHostLogin),
-		},
 		{
 			Flag:        "workspace-proxy-url",
 			Env:         "CODER_SCALETEST_WORKSPACE_PROXY_URL",
@@ -1479,6 +1507,7 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *serpent.Command {
 		},
 	}

+	targetFlags.attach(&cmd.Options)
 	tracingFlags.attach(&cmd.Options)
 	strategy.attach(&cmd.Options)
 	cleanupStrategy.attach(&cmd.Options)
@@ -1530,6 +1559,15 @@ func (r *RootCmd) scaletestDashboard() *serpent.Command {
 			if err != nil {
 				return xerrors.Errorf("create tracer provider: %w", err)
 			}
+			tracer := tracerProvider.Tracer(scaletestTracerName)
+			outputs, err := output.parse()
+			if err != nil {
+				return xerrors.Errorf("could not parse --output flags")
+			}
+			reg := prometheus.NewRegistry()
+			prometheusSrvClose := ServeHandler(ctx, logger, promhttp.HandlerFor(reg, promhttp.HandlerOpts{}), prometheusFlags.Address, "prometheus")
+			defer prometheusSrvClose()
+
 			defer func() {
 				// Allow time for traces to flush even if command context is
 				// canceled. This is a no-op if tracing is not enabled.
@@ -1541,14 +1579,7 @@ func (r *RootCmd) scaletestDashboard() *serpent.Command {
 				_, _ = fmt.Fprintf(inv.Stderr, "Waiting %s for prometheus metrics to be scraped\n", prometheusFlags.Wait)
 				<-time.After(prometheusFlags.Wait)
 			}()
-			tracer := tracerProvider.Tracer(scaletestTracerName)
-			outputs, err := output.parse()
-			if err != nil {
-				return xerrors.Errorf("could not parse --output flags")
-			}
-			reg := prometheus.NewRegistry()
-			prometheusSrvClose := ServeHandler(ctx, logger, promhttp.HandlerFor(reg, promhttp.HandlerOpts{}), prometheusFlags.Address, "prometheus")
-			defer prometheusSrvClose()
+
 			metrics := dashboard.NewMetrics(reg)

 			th := harness.NewTestHarness(strategy.toStrategy(), cleanupStrategy.toStrategy())
@@ -3,6 +3,7 @@
 package cli

 import (
+	"bytes"
 	"context"
 	"fmt"
 	"net/http"
@@ -29,12 +30,13 @@ import (

 func (r *RootCmd) scaletestNotifications() *serpent.Command {
 	var (
-		userCount           int64
-		ownerUserPercentage float64
-		notificationTimeout time.Duration
-		dialTimeout         time.Duration
-		noCleanup           bool
-		smtpAPIURL          string
+		userCount               int64
+		templateAdminPercentage float64
+		notificationTimeout     time.Duration
+		smtpRequestTimeout      time.Duration
+		dialTimeout             time.Duration
+		noCleanup               bool
+		smtpAPIURL              string

 		tracingFlags = &scaletestTracingFlags{}

@@ -77,24 +79,24 @@ func (r *RootCmd) scaletestNotifications() *serpent.Command {
 				return xerrors.Errorf("--user-count must be greater than 0")
 			}

-			if ownerUserPercentage < 0 || ownerUserPercentage > 100 {
-				return xerrors.Errorf("--owner-user-percentage must be between 0 and 100")
+			if templateAdminPercentage < 0 || templateAdminPercentage > 100 {
+				return xerrors.Errorf("--template-admin-percentage must be between 0 and 100")
 			}

 			if smtpAPIURL != "" && !strings.HasPrefix(smtpAPIURL, "http://") && !strings.HasPrefix(smtpAPIURL, "https://") {
 				return xerrors.Errorf("--smtp-api-url must start with http:// or https://")
 			}

-			ownerUserCount := int64(float64(userCount) * ownerUserPercentage / 100)
-			if ownerUserCount == 0 && ownerUserPercentage > 0 {
-				ownerUserCount = 1
+			templateAdminCount := int64(float64(userCount) * templateAdminPercentage / 100)
+			if templateAdminCount == 0 && templateAdminPercentage > 0 {
+				templateAdminCount = 1
 			}
-			regularUserCount := userCount - ownerUserCount
+			regularUserCount := userCount - templateAdminCount

 			_, _ = fmt.Fprintf(inv.Stderr, "Distribution plan:\n")
 			_, _ = fmt.Fprintf(inv.Stderr, "  Total users: %d\n", userCount)
-			_, _ = fmt.Fprintf(inv.Stderr, "  Owner users: %d (%.1f%%)\n", ownerUserCount, ownerUserPercentage)
-			_, _ = fmt.Fprintf(inv.Stderr, "  Regular users: %d (%.1f%%)\n", regularUserCount, 100.0-ownerUserPercentage)
+			_, _ = fmt.Fprintf(inv.Stderr, "  Template admins: %d (%.1f%%)\n", templateAdminCount, templateAdminPercentage)
+			_, _ = fmt.Fprintf(inv.Stderr, "  Regular users: %d (%.1f%%)\n", regularUserCount, 100.0-templateAdminPercentage)

 			outputs, err := output.parse()
 			if err != nil {
@@ -127,13 +129,12 @@ func (r *RootCmd) scaletestNotifications() *serpent.Command {
 			_, _ = fmt.Fprintln(inv.Stderr, "Creating users...")

 			dialBarrier := &sync.WaitGroup{}
-			ownerWatchBarrier := &sync.WaitGroup{}
+			templateAdminWatchBarrier := &sync.WaitGroup{}
 			dialBarrier.Add(int(userCount))
-			ownerWatchBarrier.Add(int(ownerUserCount))
+			templateAdminWatchBarrier.Add(int(templateAdminCount))

 			expectedNotificationIDs := map[uuid.UUID]struct{}{
-				notificationsLib.TemplateUserAccountCreated: {},
-				notificationsLib.TemplateUserAccountDeleted: {},
+				notificationsLib.TemplateTemplateDeleted: {},
 			}

 			triggerTimes := make(map[uuid.UUID]chan time.Time, len(expectedNotificationIDs))
@@ -141,20 +142,31 @@ func (r *RootCmd) scaletestNotifications() *serpent.Command {
 				triggerTimes[id] = make(chan time.Time, 1)
 			}

+			smtpHTTPTransport := &http.Transport{
+				MaxConnsPerHost:     512,
+				MaxIdleConnsPerHost: 512,
+				IdleConnTimeout:     60 * time.Second,
+			}
+			smtpHTTPClient := &http.Client{
+				Transport: smtpHTTPTransport,
+			}
+
 			configs := make([]notifications.Config, 0, userCount)
-			for range ownerUserCount {
+			for range templateAdminCount {
 				config := notifications.Config{
 					User: createusers.Config{
 						OrganizationID: me.OrganizationIDs[0],
 					},
-					Roles:                    []string{codersdk.RoleOwner},
+					Roles:                    []string{codersdk.RoleTemplateAdmin},
 					NotificationTimeout:      notificationTimeout,
 					DialTimeout:              dialTimeout,
 					DialBarrier:              dialBarrier,
-					ReceivingWatchBarrier:    ownerWatchBarrier,
+					ReceivingWatchBarrier:    templateAdminWatchBarrier,
 					ExpectedNotificationsIDs: expectedNotificationIDs,
 					Metrics:                  metrics,
 					SMTPApiURL:               smtpAPIURL,
+					SMTPRequestTimeout:       smtpRequestTimeout,
+					SMTPHttpClient:           smtpHTTPClient,
 				}
 				if err := config.Validate(); err != nil {
 					return xerrors.Errorf("validate config: %w", err)
@@ -170,9 +182,8 @@ func (r *RootCmd) scaletestNotifications() *serpent.Command {
 					NotificationTimeout:   notificationTimeout,
 					DialTimeout:           dialTimeout,
 					DialBarrier:           dialBarrier,
-					ReceivingWatchBarrier: ownerWatchBarrier,
+					ReceivingWatchBarrier: templateAdminWatchBarrier,
 					Metrics:               metrics,
-					SMTPApiURL:            smtpAPIURL,
 				}
 				if err := config.Validate(); err != nil {
 					return xerrors.Errorf("validate config: %w", err)
@@ -180,7 +191,7 @@ func (r *RootCmd) scaletestNotifications() *serpent.Command {
 				configs = append(configs, config)
 			}

-			go triggerUserNotifications(
+			go triggerNotifications(
 				ctx,
 				logger,
 				client,
@@ -261,23 +272,30 @@ func (r *RootCmd) scaletestNotifications() *serpent.Command {
 			Required:      true,
 		},
 		{
-			Flag:        "owner-user-percentage",
-			Env:         "CODER_SCALETEST_NOTIFICATION_OWNER_USER_PERCENTAGE",
+			Flag:        "template-admin-percentage",
+			Env:         "CODER_SCALETEST_NOTIFICATION_TEMPLATE_ADMIN_PERCENTAGE",
 			Default:     "20.0",
-			Description: "Percentage of users to assign Owner role to (0-100).",
-			Value:       serpent.Float64Of(&ownerUserPercentage),
+			Description: "Percentage of users to assign Template Admin role to (0-100).",
+			Value:       serpent.Float64Of(&templateAdminPercentage),
 		},
 		{
 			Flag:        "notification-timeout",
 			Env:         "CODER_SCALETEST_NOTIFICATION_TIMEOUT",
-			Default:     "5m",
+			Default:     "10m",
 			Description: "How long to wait for notifications after triggering.",
 			Value:       serpent.DurationOf(&notificationTimeout),
 		},
+		{
+			Flag:        "smtp-request-timeout",
+			Env:         "CODER_SCALETEST_SMTP_REQUEST_TIMEOUT",
+			Default:     "5m",
+			Description: "Timeout for SMTP requests.",
+			Value:       serpent.DurationOf(&smtpRequestTimeout),
+		},
 		{
 			Flag:        "dial-timeout",
 			Env:         "CODER_SCALETEST_DIAL_TIMEOUT",
-			Default:     "2m",
+			Default:     "10m",
 			Description: "Timeout for dialing the notification websocket endpoint.",
 			Value:       serpent.DurationOf(&dialTimeout),
 		},
@@ -379,9 +397,9 @@ func computeNotificationLatencies(
 	return nil
 }

-// triggerUserNotifications waits for all test users to connect,
-// then creates and deletes a test user to trigger notification events for testing.
-func triggerUserNotifications(
+// triggerNotifications waits for all test users to connect,
+// then creates and deletes a test template to trigger notification events for testing.
+func triggerNotifications(
 	ctx context.Context,
 	logger slog.Logger,
 	client *codersdk.Client,
@@ -414,34 +432,49 @@ func triggerUserNotifications(
 		return
 	}

-	const (
-		triggerUsername = "scaletest-trigger-user"
-		triggerEmail    = "scaletest-trigger@example.com"
-	)
+	logger.Info(ctx, "creating test template to test notifications")

-	logger.Info(ctx, "creating test user to test notifications",
-		slog.F("username", triggerUsername),
-		slog.F("email", triggerEmail),
-		slog.F("org_id", orgID))
+	// Upload empty template file.
+	file, err := client.Upload(ctx, codersdk.ContentTypeTar, bytes.NewReader([]byte{}))
+	if err != nil {
+		logger.Error(ctx, "upload test template", slog.Error(err))
+		return
+	}
+	logger.Info(ctx, "test template uploaded", slog.F("file_id", file.ID))

-	testUser, err := client.CreateUserWithOrgs(ctx, codersdk.CreateUserRequestWithOrgs{
-		OrganizationIDs: []uuid.UUID{orgID},
-		Username:        triggerUsername,
-		Email:           triggerEmail,
-		Password:        "test-password-123",
+	// Create template version.
+	version, err := client.CreateTemplateVersion(ctx, orgID, codersdk.CreateTemplateVersionRequest{
+		StorageMethod: codersdk.ProvisionerStorageMethodFile,
+		FileID:        file.ID,
+		Provisioner:   codersdk.ProvisionerTypeEcho,
 	})
 	if err != nil {
-		logger.Error(ctx, "create test user", slog.Error(err))
+		logger.Error(ctx, "create test template version", slog.Error(err))
 		return
 	}
-	expectedNotifications[notificationsLib.TemplateUserAccountCreated] <- time.Now()
+	logger.Info(ctx, "test template version created", slog.F("template_version_id", version.ID))

-	err = client.DeleteUser(ctx, testUser.ID)
+	// Create template.
+	testTemplate, err := client.CreateTemplate(ctx, orgID, codersdk.CreateTemplateRequest{
+		Name:        "scaletest-test-template",
+		Description: "scaletest-test-template",
+		VersionID:   version.ID,
+	})
 	if err != nil {
-		logger.Error(ctx, "delete test user", slog.Error(err))
+		logger.Error(ctx, "create test template", slog.Error(err))
 		return
 	}
-	expectedNotifications[notificationsLib.TemplateUserAccountDeleted] <- time.Now()
-	close(expectedNotifications[notificationsLib.TemplateUserAccountCreated])
-	close(expectedNotifications[notificationsLib.TemplateUserAccountDeleted])
+	logger.Info(ctx, "test template created", slog.F("template_id", testTemplate.ID))
+
+	// Delete template to trigger notification.
+	err = client.DeleteTemplate(ctx, testTemplate.ID)
+	if err != nil {
+		logger.Error(ctx, "delete test template", slog.Error(err))
+		return
+	}
+	logger.Info(ctx, "test template deleted", slog.F("template_id", testTemplate.ID))
+
+	// Record expected notification.
+	expectedNotifications[notificationsLib.TemplateTemplateDeleted] <- time.Now()
+	close(expectedNotifications[notificationsLib.TemplateTemplateDeleted])
 }
@@ -0,0 +1,298 @@
+//go:build !slim
+
+package cli
+
+import (
+	"fmt"
+	"net/http"
+	"os/signal"
+	"strconv"
+	"sync"
+	"time"
+
+	"github.com/prometheus/client_golang/prometheus"
+	"github.com/prometheus/client_golang/prometheus/promhttp"
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/codersdk"
+	"github.com/coder/coder/v2/scaletest/harness"
+	"github.com/coder/coder/v2/scaletest/prebuilds"
+	"github.com/coder/quartz"
+	"github.com/coder/serpent"
+)
+
+func (r *RootCmd) scaletestPrebuilds() *serpent.Command {
+	var (
+		numTemplates              int64
+		numPresets                int64
+		numPresetPrebuilds        int64
+		templateVersionJobTimeout time.Duration
+		prebuildWorkspaceTimeout  time.Duration
+		noCleanup                 bool
+
+		tracingFlags    = &scaletestTracingFlags{}
+		timeoutStrategy = &timeoutFlags{}
+		cleanupStrategy = newScaletestCleanupStrategy()
+		output          = &scaletestOutputFlags{}
+		prometheusFlags = &scaletestPrometheusFlags{}
+	)
+
+	cmd := &serpent.Command{
+		Use:   "prebuilds",
+		Short: "Creates prebuild workspaces on the Coder server.",
+		Handler: func(inv *serpent.Invocation) error {
+			ctx := inv.Context()
+			client, err := r.InitClient(inv)
+			if err != nil {
+				return err
+			}
+
+			notifyCtx, stop := signal.NotifyContext(ctx, StopSignals...)
+			defer stop()
+			ctx = notifyCtx
+
+			me, err := requireAdmin(ctx, client)
+			if err != nil {
+				return err
+			}
+
+			client.HTTPClient = &http.Client{
+				Transport: &codersdk.HeaderTransport{
+					Transport: http.DefaultTransport,
+					Header: map[string][]string{
+						codersdk.BypassRatelimitHeader: {"true"},
+					},
+				},
+			}
+
+			if numTemplates <= 0 {
+				return xerrors.Errorf("--num-templates must be greater than 0")
+			}
+			if numPresets <= 0 {
+				return xerrors.Errorf("--num-presets must be greater than 0")
+			}
+			if numPresetPrebuilds <= 0 {
+				return xerrors.Errorf("--num-preset-prebuilds must be greater than 0")
+			}
+
+			outputs, err := output.parse()
+			if err != nil {
+				return xerrors.Errorf("parse output flags: %w", err)
+			}
+
+			tracerProvider, closeTracing, tracingEnabled, err := tracingFlags.provider(ctx)
+			if err != nil {
+				return xerrors.Errorf("create tracer provider: %w", err)
+			}
+			tracer := tracerProvider.Tracer(scaletestTracerName)
+
+			reg := prometheus.NewRegistry()
+			metrics := prebuilds.NewMetrics(reg)
+
+			logger := inv.Logger
+			prometheusSrvClose := ServeHandler(ctx, logger, promhttp.HandlerFor(reg, promhttp.HandlerOpts{}), prometheusFlags.Address, "prometheus")
+			defer prometheusSrvClose()
+
+			defer func() {
+				_, _ = fmt.Fprintln(inv.Stderr, "\nUploading traces...")
+				if err := closeTracing(ctx); err != nil {
+					_, _ = fmt.Fprintf(inv.Stderr, "\nError uploading traces: %+v\n", err)
+				}
+				_, _ = fmt.Fprintf(inv.Stderr, "Waiting %s for prometheus metrics to be scraped\n", prometheusFlags.Wait)
+				<-time.After(prometheusFlags.Wait)
+			}()
+
+			err = client.PutPrebuildsSettings(ctx, codersdk.PrebuildsSettings{
+				ReconciliationPaused: true,
+			})
+			if err != nil {
+				return xerrors.Errorf("pause prebuilds: %w", err)
+			}
+
+			setupBarrier := new(sync.WaitGroup)
+			setupBarrier.Add(int(numTemplates))
+			creationBarrier := new(sync.WaitGroup)
+			creationBarrier.Add(int(numTemplates))
+			deletionSetupBarrier := new(sync.WaitGroup)
+			deletionSetupBarrier.Add(1)
+			deletionBarrier := new(sync.WaitGroup)
+			deletionBarrier.Add(int(numTemplates))
+
+			th := harness.NewTestHarness(timeoutStrategy.wrapStrategy(harness.ConcurrentExecutionStrategy{}), cleanupStrategy.toStrategy())
+
+			for i := range numTemplates {
+				id := strconv.Itoa(int(i))
+				cfg := prebuilds.Config{
+					OrganizationID:            me.OrganizationIDs[0],
+					NumPresets:                int(numPresets),
+					NumPresetPrebuilds:        int(numPresetPrebuilds),
+					TemplateVersionJobTimeout: templateVersionJobTimeout,
+					PrebuildWorkspaceTimeout:  prebuildWorkspaceTimeout,
+					Metrics:                   metrics,
+					SetupBarrier:              setupBarrier,
+					CreationBarrier:           creationBarrier,
+					DeletionSetupBarrier:      deletionSetupBarrier,
+					DeletionBarrier:           deletionBarrier,
+					Clock:                     quartz.NewReal(),
+				}
+				err := cfg.Validate()
+				if err != nil {
+					return xerrors.Errorf("validate config: %w", err)
+				}
+
+				var runner harness.Runnable = prebuilds.NewRunner(client, cfg)
+				if tracingEnabled {
+					runner = &runnableTraceWrapper{
+						tracer:   tracer,
+						spanName: fmt.Sprintf("prebuilds/%s", id),
+						runner:   runner,
+					}
+				}
+
+				th.AddRun("prebuilds", id, runner)
+			}
+
+			_, _ = fmt.Fprintf(inv.Stderr, "Creating %d templates with %d presets and %d prebuilds per preset...\n",
+				numTemplates, numPresets, numPresetPrebuilds)
+			_, _ = fmt.Fprintf(inv.Stderr, "Total expected prebuilds: %d\n", numTemplates*numPresets*numPresetPrebuilds)
+
+			testCtx, testCancel := timeoutStrategy.toContext(ctx)
+			defer testCancel()
+
+			runErrCh := make(chan error, 1)
+			go func() {
+				runErrCh <- th.Run(testCtx)
+			}()
+
+			_, _ = fmt.Fprintln(inv.Stderr, "Waiting for all templates to be created...")
+			setupBarrier.Wait()
+			_, _ = fmt.Fprintln(inv.Stderr, "All templates created")
+
+			err = client.PutPrebuildsSettings(ctx, codersdk.PrebuildsSettings{
+				ReconciliationPaused: false,
+			})
+			if err != nil {
+				return xerrors.Errorf("resume prebuilds: %w", err)
+			}
+
+			_, _ = fmt.Fprintln(inv.Stderr, "Waiting for all prebuilds to be created...")
+			creationBarrier.Wait()
+			_, _ = fmt.Fprintln(inv.Stderr, "All prebuilds created")
+
+			err = client.PutPrebuildsSettings(ctx, codersdk.PrebuildsSettings{
+				ReconciliationPaused: true,
+			})
+			if err != nil {
+				return xerrors.Errorf("pause prebuilds before deletion: %w", err)
+			}
+
+			_, _ = fmt.Fprintln(inv.Stderr, "Prebuilds paused, signaling runners to prepare for deletion")
+			deletionSetupBarrier.Done()
+
+			_, _ = fmt.Fprintln(inv.Stderr, "Waiting for all templates to be updated with 0 prebuilds...")
+			deletionBarrier.Wait()
+			_, _ = fmt.Fprintln(inv.Stderr, "All templates updated")
+
+			err = client.PutPrebuildsSettings(ctx, codersdk.PrebuildsSettings{
+				ReconciliationPaused: false,
+			})
+			if err != nil {
+				return xerrors.Errorf("resume prebuilds for deletion: %w", err)
+			}
+
+			_, _ = fmt.Fprintln(inv.Stderr, "Waiting for all prebuilds to be deleted...")
+			err = <-runErrCh
+			if err != nil {
+				return xerrors.Errorf("run test harness (harness failure, not a test failure): %w", err)
+			}
+
+			// If the command was interrupted, skip cleanup & stats
+			if notifyCtx.Err() != nil {
+				return notifyCtx.Err()
+			}
+
+			res := th.Results()
+			for _, o := range outputs {
+				err = o.write(res, inv.Stdout)
+				if err != nil {
+					return xerrors.Errorf("write output %q to %q: %w", o.format, o.path, err)
+				}
+			}
+
+			if !noCleanup {
+				_, _ = fmt.Fprintln(inv.Stderr, "\nStarting cleanup (deleting templates)...")
+
+				cleanupCtx, cleanupCancel := cleanupStrategy.toContext(ctx)
+				defer cleanupCancel()
+
+				err = th.Cleanup(cleanupCtx)
+				if err != nil {
+					return xerrors.Errorf("cleanup tests: %w", err)
+				}
+
+				// If the cleanup was interrupted, skip stats
+				if notifyCtx.Err() != nil {
+					return notifyCtx.Err()
+				}
+			}
+
+			if res.TotalFail > 0 {
+				return xerrors.New("prebuild creation test failed, see above for more details")
+			}
+
+			return nil
+		},
+	}
+
+	cmd.Options = serpent.OptionSet{
+		{
+			Flag:        "num-templates",
+			Env:         "CODER_SCALETEST_PREBUILDS_NUM_TEMPLATES",
+			Default:     "1",
+			Description: "Number of templates to create for the test.",
+			Value:       serpent.Int64Of(&numTemplates),
+		},
+		{
+			Flag:        "num-presets",
+			Env:         "CODER_SCALETEST_PREBUILDS_NUM_PRESETS",
+			Default:     "1",
+			Description: "Number of presets per template.",
+			Value:       serpent.Int64Of(&numPresets),
+		},
+		{
+			Flag:        "num-preset-prebuilds",
+			Env:         "CODER_SCALETEST_PREBUILDS_NUM_PRESET_PREBUILDS",
+			Default:     "1",
+			Description: "Number of prebuilds per preset.",
+			Value:       serpent.Int64Of(&numPresetPrebuilds),
+		},
+		{
+			Flag:        "template-version-job-timeout",
+			Env:         "CODER_SCALETEST_PREBUILDS_TEMPLATE_VERSION_JOB_TIMEOUT",
+			Default:     "5m",
+			Description: "Timeout for template version provisioning jobs.",
+			Value:       serpent.DurationOf(&templateVersionJobTimeout),
+		},
+		{
+			Flag:        "prebuild-workspace-timeout",
+			Env:         "CODER_SCALETEST_PREBUILDS_WORKSPACE_TIMEOUT",
+			Default:     "10m",
+			Description: "Timeout for all prebuild workspaces to be created/deleted.",
+			Value:       serpent.DurationOf(&prebuildWorkspaceTimeout),
+		},
+		{
+			Flag:        "skip-cleanup",
+			Env:         "CODER_SCALETEST_PREBUILDS_SKIP_CLEANUP",
+			Description: "Skip cleanup (deletion test) and leave resources intact.",
+			Value:       serpent.BoolOf(&noCleanup),
+		},
+	}
+
+	tracingFlags.attach(&cmd.Options)
+	timeoutStrategy.attach(&cmd.Options)
+	cleanupStrategy.attach(&cmd.Options)
+	output.attach(&cmd.Options)
+	prometheusFlags.attach(&cmd.Options)
+
+	return cmd
+}
@@ -0,0 +1,275 @@
+//go:build !slim
+
+package cli
+
+import (
+	"context"
+	"fmt"
+	"net/http"
+	"sync"
+	"time"
+
+	"github.com/google/uuid"
+	"github.com/prometheus/client_golang/prometheus"
+	"github.com/prometheus/client_golang/prometheus/promhttp"
+	"golang.org/x/xerrors"
+
+	"cdr.dev/slog"
+	"cdr.dev/slog/sloggers/sloghuman"
+	"github.com/coder/serpent"
+
+	"github.com/coder/coder/v2/codersdk"
+	"github.com/coder/coder/v2/scaletest/harness"
+	"github.com/coder/coder/v2/scaletest/taskstatus"
+)
+
+const (
+	taskStatusTestName = "task-status"
+)
+
+func (r *RootCmd) scaletestTaskStatus() *serpent.Command {
+	var (
+		count                int64
+		template             string
+		workspaceNamePrefix  string
+		appSlug              string
+		reportStatusPeriod   time.Duration
+		reportStatusDuration time.Duration
+		baselineDuration     time.Duration
+		tracingFlags         = &scaletestTracingFlags{}
+		prometheusFlags      = &scaletestPrometheusFlags{}
+		timeoutStrategy      = &timeoutFlags{}
+		cleanupStrategy      = newScaletestCleanupStrategy()
+		output               = &scaletestOutputFlags{}
+	)
+	orgContext := NewOrganizationContext()
+
+	cmd := &serpent.Command{
+		Use:   "task-status",
+		Short: "Generates load on the Coder server by simulating task status reporting",
+		Long: `This test creates external workspaces and simulates AI agents reporting task status.
+After all runners connect, it waits for the baseline duration before triggering status reporting.`,
+		Handler: func(inv *serpent.Invocation) error {
+			ctx := inv.Context()
+
+			outputs, err := output.parse()
+			if err != nil {
+				return xerrors.Errorf("could not parse --output flags: %w", err)
+			}
+
+			client, err := r.InitClient(inv)
+			if err != nil {
+				return err
+			}
+
+			org, err := orgContext.Selected(inv, client)
+			if err != nil {
+				return err
+			}
+
+			_, err = requireAdmin(ctx, client)
+			if err != nil {
+				return err
+			}
+
+			// Disable rate limits for this test
+			client.HTTPClient = &http.Client{
+				Transport: &codersdk.HeaderTransport{
+					Transport: http.DefaultTransport,
+					Header: map[string][]string{
+						codersdk.BypassRatelimitHeader: {"true"},
+					},
+				},
+			}
+
+			// Find the template
+			tpl, err := parseTemplate(ctx, client, []uuid.UUID{org.ID}, template)
+			if err != nil {
+				return xerrors.Errorf("parse template %q: %w", template, err)
+			}
+			templateID := tpl.ID
+
+			reg := prometheus.NewRegistry()
+			metrics := taskstatus.NewMetrics(reg)
+
+			logger := slog.Make(sloghuman.Sink(inv.Stdout)).Leveled(slog.LevelDebug)
+			prometheusSrvClose := ServeHandler(ctx, logger, promhttp.HandlerFor(reg, promhttp.HandlerOpts{}), prometheusFlags.Address, "prometheus")
+			defer prometheusSrvClose()
+
+			tracerProvider, closeTracing, tracingEnabled, err := tracingFlags.provider(ctx)
+			if err != nil {
+				return xerrors.Errorf("create tracer provider: %w", err)
+			}
+			defer func() {
+				// Allow time for traces to flush even if command context is
+				// canceled. This is a no-op if tracing is not enabled.
+				_, _ = fmt.Fprintln(inv.Stderr, "\nUploading traces...")
+				if err := closeTracing(ctx); err != nil {
+					_, _ = fmt.Fprintf(inv.Stderr, "\nError uploading traces: %+v\n", err)
+				}
+				// Wait for prometheus metrics to be scraped
+				_, _ = fmt.Fprintf(inv.Stderr, "Waiting %s for prometheus metrics to be scraped\n", prometheusFlags.Wait)
+				<-time.After(prometheusFlags.Wait)
+			}()
+			tracer := tracerProvider.Tracer(scaletestTracerName)
+
+			// Setup shared resources for coordination
+			connectedWaitGroup := &sync.WaitGroup{}
+			connectedWaitGroup.Add(int(count))
+			startReporting := make(chan struct{})
+
+			// Create the test harness
+			th := harness.NewTestHarness(
+				timeoutStrategy.wrapStrategy(harness.ConcurrentExecutionStrategy{}),
+				cleanupStrategy.toStrategy(),
+			)
+
+			// Create runners
+			for i := range count {
+				workspaceName := fmt.Sprintf("%s-%d", workspaceNamePrefix, i)
+				cfg := taskstatus.Config{
+					TemplateID:           templateID,
+					WorkspaceName:        workspaceName,
+					AppSlug:              appSlug,
+					ConnectedWaitGroup:   connectedWaitGroup,
+					StartReporting:       startReporting,
+					ReportStatusPeriod:   reportStatusPeriod,
+					ReportStatusDuration: reportStatusDuration,
+					Metrics:              metrics,
+					MetricLabelValues:    []string{},
+				}
+
+				if err := cfg.Validate(); err != nil {
+					return xerrors.Errorf("validate config for runner %d: %w", i, err)
+				}
+
+				var runner harness.Runnable = taskstatus.NewRunner(client, cfg)
+				if tracingEnabled {
+					runner = &runnableTraceWrapper{
+						tracer:   tracer,
+						spanName: fmt.Sprintf("%s/%d", taskStatusTestName, i),
+						runner:   runner,
+					}
+				}
+				th.AddRun(taskStatusTestName, workspaceName, runner)
+			}
+
+			// Start the test in a separate goroutine so we can coordinate timing
+			testCtx, testCancel := timeoutStrategy.toContext(ctx)
+			defer testCancel()
+			testDone := make(chan error)
+			go func() {
+				testDone <- th.Run(testCtx)
+			}()
+
+			// Wait for all runners to connect
+			logger.Info(ctx, "waiting for all runners to connect")
+			waitCtx, waitCancel := context.WithTimeout(ctx, 5*time.Minute)
+			defer waitCancel()
+
+			connectDone := make(chan struct{})
+			go func() {
+				connectedWaitGroup.Wait()
+				close(connectDone)
+			}()
+
+			select {
+			case <-waitCtx.Done():
+				return xerrors.Errorf("timeout waiting for runners to connect")
+			case <-connectDone:
+				logger.Info(ctx, "all runners connected")
+			}
+
+			// Wait for baseline duration
+			logger.Info(ctx, "waiting for baseline duration", slog.F("duration", baselineDuration))
+			select {
+			case <-ctx.Done():
+				return ctx.Err()
+			case <-time.After(baselineDuration):
+			}
+
+			// Trigger all runners to start reporting
+			logger.Info(ctx, "triggering runners to start reporting task status")
+			close(startReporting)
+
+			// Wait for the test to complete
+			err = <-testDone
+			if err != nil {
+				return xerrors.Errorf("run test harness: %w", err)
+			}
+
+			res := th.Results()
+			for _, o := range outputs {
+				err = o.write(res, inv.Stdout)
+				if err != nil {
+					return xerrors.Errorf("write output %q to %q: %w", o.format, o.path, err)
+				}
+			}
+
+			cleanupCtx, cleanupCancel := cleanupStrategy.toContext(ctx)
+			defer cleanupCancel()
+			err = th.Cleanup(cleanupCtx)
+			if err != nil {
+				return xerrors.Errorf("cleanup tests: %w", err)
+			}
+
+			if res.TotalFail > 0 {
+				return xerrors.New("load test failed, see above for more details")
+			}
+
+			return nil
+		},
+	}
+
+	cmd.Options = serpent.OptionSet{
+		{
+			Flag:        "count",
+			Description: "Number of concurrent runners to create.",
+			Default:     "10",
+			Value:       serpent.Int64Of(&count),
+		},
+		{
+			Flag:        "template",
+			Description: "Name or UUID of the template to use for the scale test. The template MUST include a coder_external_agent and a coder_app.",
+			Default:     "scaletest-task-status",
+			Value:       serpent.StringOf(&template),
+		},
+		{
+			Flag:        "workspace-name-prefix",
+			Description: "Prefix for workspace names (will be suffixed with index).",
+			Default:     "scaletest-task-status",
+			Value:       serpent.StringOf(&workspaceNamePrefix),
+		},
+		{
+			Flag:        "app-slug",
+			Description: "Slug of the app designated as the AI Agent.",
+			Default:     "ai-agent",
+			Value:       serpent.StringOf(&appSlug),
+		},
+		{
+			Flag:        "report-status-period",
+			Description: "Time between reporting task statuses.",
+			Default:     "10s",
+			Value:       serpent.DurationOf(&reportStatusPeriod),
+		},
+		{
+			Flag:        "report-status-duration",
+			Description: "Total time to report task statuses after baseline.",
+			Default:     "15m",
+			Value:       serpent.DurationOf(&reportStatusDuration),
+		},
+		{
+			Flag:        "baseline-duration",
+			Description: "Duration to wait after all runners connect before starting to report status.",
+			Default:     "10m",
+			Value:       serpent.DurationOf(&baselineDuration),
+		},
+	}
+	orgContext.AttachOptions(cmd)
+	output.attach(&cmd.Options)
+	tracingFlags.attach(&cmd.Options)
+	prometheusFlags.attach(&cmd.Options)
+	timeoutStrategy.attach(&cmd.Options)
+	cleanupStrategy.attach(&cmd.Options)
+	return cmd
+}
@@ -0,0 +1,426 @@
+package cli_test
+
+import (
+	"bytes"
+	"crypto/rand"
+	"encoding/binary"
+	"fmt"
+	"net/url"
+	"os"
+	"path"
+	"runtime"
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/cli"
+	"github.com/coder/coder/v2/cli/clitest"
+	"github.com/coder/coder/v2/cli/config"
+	"github.com/coder/coder/v2/cli/sessionstore"
+	"github.com/coder/coder/v2/coderd/coderdtest"
+	"github.com/coder/coder/v2/pty/ptytest"
+	"github.com/coder/serpent"
+)
+
+// keyringTestServiceName generates a unique service name for keyring tests
+// using the test name and a nanosecond timestamp to prevent collisions.
+func keyringTestServiceName(t *testing.T) string {
+	t.Helper()
+	var n uint32
+	err := binary.Read(rand.Reader, binary.BigEndian, &n)
+	if err != nil {
+		t.Fatal(err)
+	}
+	return fmt.Sprintf("%s_%v_%d", t.Name(), time.Now().UnixNano(), n)
+}
+
+type keyringTestEnv struct {
+	serviceName string
+	keyring     sessionstore.Keyring
+	inv         *serpent.Invocation
+	cfg         config.Root
+	clientURL   *url.URL
+}
+
+func setupKeyringTestEnv(t *testing.T, clientURL string, args ...string) keyringTestEnv {
+	t.Helper()
+
+	var root cli.RootCmd
+
+	cmd, err := root.Command(root.AGPL())
+	require.NoError(t, err)
+
+	serviceName := keyringTestServiceName(t)
+	root.WithKeyringServiceName(serviceName)
+	root.UseKeyringWithGlobalConfig()
+
+	inv, cfg := clitest.NewWithDefaultKeyringCommand(t, cmd, args...)
+
+	parsedURL, err := url.Parse(clientURL)
+	require.NoError(t, err)
+
+	backend := sessionstore.NewKeyringWithService(serviceName)
+	t.Cleanup(func() {
+		_ = backend.Delete(parsedURL)
+	})
+
+	return keyringTestEnv{serviceName, backend, inv, cfg, parsedURL}
+}
+
+func TestUseKeyring(t *testing.T) {
+	// Verify that the --use-keyring flag default opts into using a keyring backend
+	// for storing session tokens instead of plain text files.
+	t.Parallel()
+
+	t.Run("Login", func(t *testing.T) {
+		t.Parallel()
+
+		if runtime.GOOS != "windows" && runtime.GOOS != "darwin" {
+			t.Skip("keyring is not supported on this OS")
+		}
+
+		// Create a test server
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+
+		// Create a pty for interactive prompts
+		pty := ptytest.New(t)
+
+		// Create CLI invocation which defaults to using the keyring
+		env := setupKeyringTestEnv(t, client.URL.String(),
+			"login",
+			"--force-tty",
+			"--no-open",
+			client.URL.String())
+		inv := env.inv
+		inv.Stdin = pty.Input()
+		inv.Stdout = pty.Output()
+
+		// Run login in background
+		doneChan := make(chan struct{})
+		go func() {
+			defer close(doneChan)
+			err := inv.Run()
+			assert.NoError(t, err)
+		}()
+
+		// Provide the token when prompted
+		pty.ExpectMatch("Paste your token here:")
+		pty.WriteLine(client.SessionToken())
+		pty.ExpectMatch("Welcome to Coder")
+		<-doneChan
+
+		// Verify that session file was NOT created (using keyring instead)
+		sessionFile := path.Join(string(env.cfg), "session")
+		_, err := os.Stat(sessionFile)
+		require.True(t, os.IsNotExist(err), "session file should not exist when using keyring")
+
+		// Verify that the credential IS stored in OS keyring
+		cred, err := env.keyring.Read(env.clientURL)
+		require.NoError(t, err, "credential should be stored in OS keyring")
+		require.Equal(t, client.SessionToken(), cred, "stored token should match login token")
+	})
+
+	t.Run("Logout", func(t *testing.T) {
+		t.Parallel()
+
+		if runtime.GOOS != "windows" && runtime.GOOS != "darwin" {
+			t.Skip("keyring is not supported on this OS")
+		}
+
+		// Create a test server
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+
+		// Create a pty for interactive prompts
+		pty := ptytest.New(t)
+
+		// First, login with the keyring (default)
+		env := setupKeyringTestEnv(t, client.URL.String(),
+			"login",
+			"--force-tty",
+			"--no-open",
+			client.URL.String(),
+		)
+		loginInv := env.inv
+		loginInv.Stdin = pty.Input()
+		loginInv.Stdout = pty.Output()
+
+		doneChan := make(chan struct{})
+		go func() {
+			defer close(doneChan)
+			err := loginInv.Run()
+			assert.NoError(t, err)
+		}()
+
+		pty.ExpectMatch("Paste your token here:")
+		pty.WriteLine(client.SessionToken())
+		pty.ExpectMatch("Welcome to Coder")
+		<-doneChan
+
+		// Verify credential exists in OS keyring
+		cred, err := env.keyring.Read(env.clientURL)
+		require.NoError(t, err, "read credential should succeed before logout")
+		require.NotEmpty(t, cred, "credential should exist before logout")
+
+		// Now logout using the same keyring service name
+		var logoutRoot cli.RootCmd
+		logoutCmd, err := logoutRoot.Command(logoutRoot.AGPL())
+		require.NoError(t, err)
+		logoutRoot.WithKeyringServiceName(env.serviceName)
+		logoutRoot.UseKeyringWithGlobalConfig()
+
+		logoutInv, _ := clitest.NewWithDefaultKeyringCommand(t, logoutCmd,
+			"logout",
+			"--yes",
+			"--global-config", string(env.cfg),
+		)
+
+		var logoutOut bytes.Buffer
+		logoutInv.Stdout = &logoutOut
+
+		err = logoutInv.Run()
+		require.NoError(t, err, "logout should succeed")
+
+		// Verify the credential was deleted from OS keyring
+		_, err = env.keyring.Read(env.clientURL)
+		require.ErrorIs(t, err, os.ErrNotExist, "credential should be deleted from keyring after logout")
+	})
+
+	t.Run("DefaultFileStorage", func(t *testing.T) {
+		t.Parallel()
+
+		if runtime.GOOS != "linux" {
+			t.Skip("file storage is the default for Linux")
+		}
+
+		// Create a test server
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+
+		// Create a pty for interactive prompts
+		pty := ptytest.New(t)
+
+		env := setupKeyringTestEnv(t, client.URL.String(),
+			"login",
+			"--force-tty",
+			"--no-open",
+			client.URL.String(),
+		)
+		inv := env.inv
+		inv.Stdin = pty.Input()
+		inv.Stdout = pty.Output()
+
+		doneChan := make(chan struct{})
+		go func() {
+			defer close(doneChan)
+			err := inv.Run()
+			assert.NoError(t, err)
+		}()
+
+		pty.ExpectMatch("Paste your token here:")
+		pty.WriteLine(client.SessionToken())
+		pty.ExpectMatch("Welcome to Coder")
+		<-doneChan
+
+		// Verify that session file WAS created (not using keyring)
+		sessionFile := path.Join(string(env.cfg), "session")
+		_, err := os.Stat(sessionFile)
+		require.NoError(t, err, "session file should exist when NOT using --use-keyring on Linux")
+
+		// Read and verify the token from file
+		content, err := os.ReadFile(sessionFile)
+		require.NoError(t, err, "should be able to read session file")
+		require.Equal(t, client.SessionToken(), string(content), "file should contain the session token")
+	})
+
+	t.Run("EnvironmentVariable", func(t *testing.T) {
+		t.Parallel()
+
+		// Create a test server
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+
+		// Create a pty for interactive prompts
+		pty := ptytest.New(t)
+
+		// Login using CODER_USE_KEYRING environment variable set to disable keyring usage,
+		// which should have the same behavior on all platforms.
+		env := setupKeyringTestEnv(t, client.URL.String(),
+			"login",
+			"--force-tty",
+			"--no-open",
+			client.URL.String(),
+		)
+		inv := env.inv
+		inv.Stdin = pty.Input()
+		inv.Stdout = pty.Output()
+		inv.Environ.Set("CODER_USE_KEYRING", "false")
+
+		doneChan := make(chan struct{})
+		go func() {
+			defer close(doneChan)
+			err := inv.Run()
+			assert.NoError(t, err)
+		}()
+
+		pty.ExpectMatch("Paste your token here:")
+		pty.WriteLine(client.SessionToken())
+		pty.ExpectMatch("Welcome to Coder")
+		<-doneChan
+
+		// Verify that session file WAS created (not using keyring)
+		sessionFile := path.Join(string(env.cfg), "session")
+		_, err := os.Stat(sessionFile)
+		require.NoError(t, err, "session file should exist when CODER_USE_KEYRING set to false")
+
+		// Read and verify the token from file
+		content, err := os.ReadFile(sessionFile)
+		require.NoError(t, err, "should be able to read session file")
+		require.Equal(t, client.SessionToken(), string(content), "file should contain the session token")
+	})
+
+	t.Run("DisableKeyringWithFlag", func(t *testing.T) {
+		t.Parallel()
+
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+		pty := ptytest.New(t)
+
+		// Login with --use-keyring=false to explicitly disable keyring usage, which
+		// should have the same behavior on all platforms.
+		env := setupKeyringTestEnv(t, client.URL.String(),
+			"login",
+			"--use-keyring=false",
+			"--force-tty",
+			"--no-open",
+			client.URL.String(),
+		)
+		inv := env.inv
+		inv.Stdin = pty.Input()
+		inv.Stdout = pty.Output()
+
+		doneChan := make(chan struct{})
+		go func() {
+			defer close(doneChan)
+			err := inv.Run()
+			assert.NoError(t, err)
+		}()
+
+		pty.ExpectMatch("Paste your token here:")
+		pty.WriteLine(client.SessionToken())
+		pty.ExpectMatch("Welcome to Coder")
+		<-doneChan
+
+		// Verify that session file WAS created (not using keyring)
+		sessionFile := path.Join(string(env.cfg), "session")
+		_, err := os.Stat(sessionFile)
+		require.NoError(t, err, "session file should exist when --use-keyring=false is specified")
+
+		// Read and verify the token from file
+		content, err := os.ReadFile(sessionFile)
+		require.NoError(t, err, "should be able to read session file")
+		require.Equal(t, client.SessionToken(), string(content), "file should contain the session token")
+	})
+}
+
+func TestUseKeyringUnsupportedOS(t *testing.T) {
+	// Verify that on unsupported operating systems, file-based storage is used
+	// automatically even when --use-keyring is set to true (the default).
+	t.Parallel()
+
+	// Only run this on an unsupported OS.
+	if runtime.GOOS == "windows" || runtime.GOOS == "darwin" {
+		t.Skipf("Skipping unsupported OS test on %s where keyring is supported", runtime.GOOS)
+	}
+
+	t.Run("LoginWithDefaultKeyring", func(t *testing.T) {
+		t.Parallel()
+
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+		pty := ptytest.New(t)
+
+		env := setupKeyringTestEnv(t, client.URL.String(),
+			"login",
+			"--force-tty",
+			"--no-open",
+			client.URL.String(),
+		)
+		inv := env.inv
+		inv.Stdin = pty.Input()
+		inv.Stdout = pty.Output()
+
+		doneChan := make(chan struct{})
+		go func() {
+			defer close(doneChan)
+			err := inv.Run()
+			assert.NoError(t, err)
+		}()
+
+		pty.ExpectMatch("Paste your token here:")
+		pty.WriteLine(client.SessionToken())
+		pty.ExpectMatch("Welcome to Coder")
+		<-doneChan
+
+		// Verify that session file WAS created (automatic fallback to file storage)
+		sessionFile := path.Join(string(env.cfg), "session")
+		_, err := os.Stat(sessionFile)
+		require.NoError(t, err, "session file should exist due to automatic fallback to file storage")
+
+		content, err := os.ReadFile(sessionFile)
+		require.NoError(t, err, "should be able to read session file")
+		require.Equal(t, client.SessionToken(), string(content), "file should contain the session token")
+	})
+
+	t.Run("LogoutWithDefaultKeyring", func(t *testing.T) {
+		t.Parallel()
+
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+		pty := ptytest.New(t)
+
+		// First login to create a session (will use file storage due to automatic fallback)
+		env := setupKeyringTestEnv(t, client.URL.String(),
+			"login",
+			"--force-tty",
+			"--no-open",
+			client.URL.String(),
+		)
+		loginInv := env.inv
+		loginInv.Stdin = pty.Input()
+		loginInv.Stdout = pty.Output()
+
+		doneChan := make(chan struct{})
+		go func() {
+			defer close(doneChan)
+			err := loginInv.Run()
+			assert.NoError(t, err)
+		}()
+
+		pty.ExpectMatch("Paste your token here:")
+		pty.WriteLine(client.SessionToken())
+		pty.ExpectMatch("Welcome to Coder")
+		<-doneChan
+
+		// Verify session file exists
+		sessionFile := path.Join(string(env.cfg), "session")
+		_, err := os.Stat(sessionFile)
+		require.NoError(t, err, "session file should exist before logout")
+
+		// Now logout - should succeed and delete the file
+		logoutEnv := setupKeyringTestEnv(t, client.URL.String(),
+			"logout",
+			"--yes",
+			"--global-config", string(env.cfg),
+		)
+
+		err = logoutEnv.inv.Run()
+		require.NoError(t, err, "logout should succeed with automatic file storage fallback")
+
+		_, err = os.Stat(sessionFile)
+		require.True(t, os.IsNotExist(err), "session file should be deleted after logout")
+	})
+}
@@ -19,6 +19,7 @@ import (
 	"github.com/coder/pretty"

 	"github.com/coder/coder/v2/cli/cliui"
+	"github.com/coder/coder/v2/cli/sessionstore"
 	"github.com/coder/coder/v2/coderd/userpassword"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/serpent"
@@ -114,9 +115,11 @@ func (r *RootCmd) loginWithPassword(
 	}

 	sessionToken := resp.SessionToken
-	config := r.createConfig()
-	err = config.Session().Write(sessionToken)
+	err = r.ensureTokenBackend().Write(client.URL, sessionToken)
 	if err != nil {
+		if xerrors.Is(err, sessionstore.ErrNotImplemented) {
+			return errKeyringNotSupported
+		}
 		return xerrors.Errorf("write session token: %w", err)
 	}

@@ -149,11 +152,15 @@ func (r *RootCmd) login() *serpent.Command {
 		useTokenForSession bool
 	)
 	cmd := &serpent.Command{
-		Use:        "login [<url>]",
-		Short:      "Authenticate with Coder deployment",
+		Use:   "login [<url>]",
+		Short: "Authenticate with Coder deployment",
+		Long: "By default, the session token is stored in the operating system keyring on " +
+			"macOS and Windows and a plain text file on Linux. Use the --use-keyring flag " +
+			"or CODER_USE_KEYRING environment variable to change the storage mechanism.",
 		Middleware: serpent.RequireRangeArgs(0, 1),
 		Handler: func(inv *serpent.Invocation) error {
 			ctx := inv.Context()
+
 			rawURL := ""
 			var urlSource string

@@ -198,6 +205,15 @@ func (r *RootCmd) login() *serpent.Command {
 				return err
 			}

+			// Check keyring availability before prompting the user for a token to fail fast.
+			if r.useKeyring {
+				backend := r.ensureTokenBackend()
+				_, err := backend.Read(client.URL)
+				if err != nil && xerrors.Is(err, sessionstore.ErrNotImplemented) {
+					return errKeyringNotSupported
+				}
+			}
+
 			hasFirstUser, err := client.HasFirstUser(ctx)
 			if err != nil {
 				return xerrors.Errorf("Failed to check server %q for first user, is the URL correct and is coder accessible from your browser? Error - has initial user: %w", serverURL.String(), err)
@@ -394,8 +410,11 @@ func (r *RootCmd) login() *serpent.Command {
 			}

 			config := r.createConfig()
-			err = config.Session().Write(sessionToken)
+			err = r.ensureTokenBackend().Write(client.URL, sessionToken)
 			if err != nil {
+				if xerrors.Is(err, sessionstore.ErrNotImplemented) {
+					return errKeyringNotSupported
+				}
 				return xerrors.Errorf("write session token: %w", err)
 			}
 			err = config.URL().Write(serverURL.String())
@@ -8,6 +8,7 @@ import (
 	"golang.org/x/xerrors"

 	"github.com/coder/coder/v2/cli/cliui"
+	"github.com/coder/coder/v2/cli/sessionstore"
 	"github.com/coder/serpent"
 )

@@ -46,11 +47,15 @@ func (r *RootCmd) logout() *serpent.Command {
 				errors = append(errors, xerrors.Errorf("remove URL file: %w", err))
 			}

-			err = config.Session().Delete()
+			err = r.ensureTokenBackend().Delete(client.URL)
 			// Only throw error if the session configuration file is present,
 			// otherwise the user is already logged out, and we proceed
-			if err != nil && !os.IsNotExist(err) {
-				errors = append(errors, xerrors.Errorf("remove session file: %w", err))
+			if err != nil && !xerrors.Is(err, os.ErrNotExist) {
+				if xerrors.Is(err, sessionstore.ErrNotImplemented) {
+					errors = append(errors, errKeyringNotSupported)
+				} else {
+					errors = append(errors, xerrors.Errorf("remove session token: %w", err))
+				}
 			}

 			err = config.Organization().Delete()
@@ -37,6 +37,7 @@ import (
 	"github.com/coder/coder/v2/cli/cliui"
 	"github.com/coder/coder/v2/cli/config"
 	"github.com/coder/coder/v2/cli/gitauth"
+	"github.com/coder/coder/v2/cli/sessionstore"
 	"github.com/coder/coder/v2/cli/telemetry"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/codersdk/agentsdk"
@@ -54,6 +55,8 @@ var (
 	// ErrSilent is a sentinel error that tells the command handler to just exit with a non-zero error, but not print
 	// anything.
 	ErrSilent = xerrors.New("silent error")
+
+	errKeyringNotSupported = xerrors.New("keyring storage is not supported on this operating system; omit --use-keyring to use file-based storage")
 )

 const (
@@ -68,12 +71,14 @@ const (
 	varVerbose                 = "verbose"
 	varDisableDirect           = "disable-direct-connections"
 	varDisableNetworkTelemetry = "disable-network-telemetry"
+	varUseKeyring              = "use-keyring"

 	notLoggedInMessage = "You are not logged in. Try logging in using '%s login <url>'."

 	envNoVersionCheck   = "CODER_NO_VERSION_WARNING"
 	envNoFeatureWarning = "CODER_NO_FEATURE_WARNING"
 	envSessionToken     = "CODER_SESSION_TOKEN"
+	envUseKeyring       = "CODER_USE_KEYRING"
 	//nolint:gosec
 	envAgentToken = "CODER_AGENT_TOKEN"
 	//nolint:gosec
@@ -99,6 +104,7 @@ func (r *RootCmd) CoreSubcommands() []*serpent.Command {
 		r.resetPassword(),
 		r.sharing(),
 		r.state(),
+		r.tasksCommand(),
 		r.templates(),
 		r.tokens(),
 		r.users(),
@@ -145,7 +151,6 @@ func (r *RootCmd) AGPLExperimental() []*serpent.Command {
 		r.promptExample(),
 		r.rptyCommand(),
 		r.syncCommand(),
-		r.tasksCommand(),
 		r.boundary(),
 	}
 }
@@ -475,6 +480,17 @@ func (r *RootCmd) Command(subcommands []*serpent.Command) (*serpent.Command, err
 			Value:       serpent.BoolOf(&r.disableNetworkTelemetry),
 			Group:       globalGroup,
 		},
+		{
+			Flag: varUseKeyring,
+			Env:  envUseKeyring,
+			Description: "Store and retrieve session tokens using the operating system " +
+				"keyring. This flag is ignored and file-based storage is used when " +
+				"--global-config is set or keyring usage is not supported on the current " +
+				"platform. Set to false to force file-based storage on supported platforms.",
+			Default: "true",
+			Value:   serpent.BoolOf(&r.useKeyring),
+			Group:   globalGroup,
+		},
 		{
 			Flag:        "debug-http",
 			Description: "Debug codersdk HTTP requests.",
@@ -509,6 +525,7 @@ func (r *RootCmd) Command(subcommands []*serpent.Command) (*serpent.Command, err
 type RootCmd struct {
 	clientURL     *url.URL
 	token         string
+	tokenBackend  sessionstore.Backend
 	globalConfig  string
 	header        []string
 	headerCommand string
@@ -520,9 +537,12 @@ type RootCmd struct {
 	disableDirect bool
 	debugHTTP     bool

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

 // InitClient creates and configures a new client with authentication, telemetry,
@@ -550,14 +570,19 @@ func (r *RootCmd) InitClient(inv *serpent.Invocation) (*codersdk.Client, error)
 			return nil, err
 		}
 	}
-	// Read the token stored on disk.
 	if r.token == "" {
-		r.token, err = conf.Session().Read()
+		tok, err := r.ensureTokenBackend().Read(r.clientURL)
 		// Even if there isn't a token, we don't care.
 		// Some API routes can be unauthenticated.
-		if err != nil && !os.IsNotExist(err) {
+		if err != nil && !xerrors.Is(err, os.ErrNotExist) {
+			if xerrors.Is(err, sessionstore.ErrNotImplemented) {
+				return nil, errKeyringNotSupported
+			}
 			return nil, err
 		}
+		if tok != "" {
+			r.token = tok
+		}
 	}

 	// Configure HTTP client with transport wrappers
@@ -589,7 +614,6 @@ func (r *RootCmd) InitClient(inv *serpent.Invocation) (*codersdk.Client, error)
 // This allows commands to run without requiring authentication, but still use auth if available.
 func (r *RootCmd) TryInitClient(inv *serpent.Invocation) (*codersdk.Client, error) {
 	conf := r.createConfig()
-	var err error
 	// Read the client URL stored on disk.
 	if r.clientURL == nil || r.clientURL.String() == "" {
 		rawURL, err := conf.URL().Read()
@@ -606,14 +630,19 @@ func (r *RootCmd) TryInitClient(inv *serpent.Invocation) (*codersdk.Client, erro
 			}
 		}
 	}
-	// Read the token stored on disk.
 	if r.token == "" {
-		r.token, err = conf.Session().Read()
+		tok, err := r.ensureTokenBackend().Read(r.clientURL)
 		// Even if there isn't a token, we don't care.
 		// Some API routes can be unauthenticated.
-		if err != nil && !os.IsNotExist(err) {
+		if err != nil && !xerrors.Is(err, os.ErrNotExist) {
+			if xerrors.Is(err, sessionstore.ErrNotImplemented) {
+				return nil, errKeyringNotSupported
+			}
 			return nil, err
 		}
+		if tok != "" {
+			r.token = tok
+		}
 	}

 	// Only configure the client if we have a URL
@@ -689,6 +718,45 @@ func (r *RootCmd) createUnauthenticatedClient(ctx context.Context, serverURL *ur
 	return client, nil
 }

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

@@ -1029,7 +1029,7 @@ func (r *RootCmd) Server(newAPI func(context.Context, *coderd.Options) (*coderd.
 			defer shutdownConns()

 			// Ensures that old database entries are cleaned up over time!
-			purger := dbpurge.New(ctx, logger.Named("dbpurge"), options.Database, quartz.NewReal())
+			purger := dbpurge.New(ctx, logger.Named("dbpurge"), options.Database, options.DeploymentValues, quartz.NewReal())
 			defer purger.Close()

 			// Updates workspace usage
@@ -1476,6 +1476,7 @@ func newProvisionerDaemon(
 						Listener:      terraformServer,
 						Logger:        provisionerLogger,
 						WorkDirectory: workDir,
+						Experiments:   coderAPI.Experiments,
 					},
 					CachePath: tfDir,
 					Tracer:    tracer,
@@ -2142,21 +2143,33 @@ func startBuiltinPostgres(ctx context.Context, cfg config.Root, logger slog.Logg
 	}
 	stdlibLogger := slog.Stdlib(ctx, logger.Named("postgres"), slog.LevelDebug)

-	// If the port is not defined, an available port will be found dynamically.
+	// If the port is not defined, an available port will be found dynamically. This has
+	// implications in CI because here is no way to tell Postgres to use an ephemeral
+	// port, so to avoid flaky tests in CI we need to retry EmbeddedPostgres.Start in
+	// case of a race condition where the port we quickly listen on and close in
+	// embeddedPostgresURL() is not free by the time the embedded postgres starts up.
+	// The maximum retry attempts _should_ cover most cases where port conflicts occur
+	// in CI and cause flaky tests.
 	maxAttempts := 1
 	_, err = cfg.PostgresPort().Read()
+	// Important: if retryPortDiscovery is changed to not include testing.Testing(),
+	// the retry logic below also needs to be updated to ensure we don't delete an
+	// existing database
 	retryPortDiscovery := errors.Is(err, os.ErrNotExist) && testing.Testing()
 	if retryPortDiscovery {
-		// There is no way to tell Postgres to use an ephemeral port, so in order to avoid
-		// flaky tests in CI we need to retry EmbeddedPostgres.Start in case of a race
-		// condition where the port we quickly listen on and close in embeddedPostgresURL()
-		// is not free by the time the embedded postgres starts up. This maximum_should
-		// cover most cases where port conflicts occur in CI and cause flaky tests.
 		maxAttempts = 3
 	}

 	var startErr error
 	for attempt := 0; attempt < maxAttempts; attempt++ {
+		if retryPortDiscovery && attempt > 0 {
+			// Clean up the data and runtime directories and the port file from the
+			// previous failed attempt to ensure a clean slate for the next attempt.
+			_ = os.RemoveAll(filepath.Join(cfg.PostgresPath(), "data"))
+			_ = os.RemoveAll(filepath.Join(cfg.PostgresPath(), "runtime"))
+			_ = cfg.PostgresPort().Delete()
+		}
+
 		// Ensure a password and port have been generated.
 		connectionURL, err := embeddedPostgresURL(cfg)
 		if err != nil {
@@ -2203,11 +2216,6 @@ func startBuiltinPostgres(ctx context.Context, cfg config.Root, logger slog.Logg
 			slog.F("port", pgPort),
 			slog.Error(startErr),
 		)
-
-		if retryPortDiscovery {
-			// Since a retry is needed, we wipe the port stored here at the beginning of the loop.
-			_ = cfg.PostgresPort().Delete()
-		}
 	}

 	return "", nil, xerrors.Errorf("failed to start built-in PostgreSQL after %d attempts. "+
@@ -0,0 +1,237 @@
+// Package sessionstore provides CLI session token storage mechanisms.
+// Operating system keyring storage is intended to have compatibility with other Coder
+// applications (e.g. Coder Desktop, Coder provider for JetBrains Toolbox, etc) so that
+// applications can read/write the same credential stored in the keyring.
+//
+// Note that we aren't using an existing Go package zalando/go-keyring here for a few
+// reasons. 1) It prescribes the format of the target credential name in the OS keyrings,
+// which makes our life difficult for compatibility with other Coder applications. 2)
+// It uses init functions that make it difficult to test with. As a result, the OS
+// keyring implementations may be adapted from zalando/go-keyring source (i.e. Windows).
+package sessionstore
+
+import (
+	"encoding/json"
+	"errors"
+	"net/url"
+	"os"
+	"strings"
+
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/cli/config"
+)
+
+// Backend is a storage backend for session tokens.
+type Backend interface {
+	// Read returns the session token for the given server URL or an error, if any. It
+	// will return os.ErrNotExist if no token exists for the given URL.
+	Read(serverURL *url.URL) (string, error)
+	// Write stores the session token for the given server URL.
+	Write(serverURL *url.URL, token string) error
+	// Delete removes the session token for the given server URL or an error, if any.
+	// It will return os.ErrNotExist error if no token exists to delete.
+	Delete(serverURL *url.URL) error
+}
+
+var (
+
+	// ErrSetDataTooBig is returned if `keyringProvider.Set` was called with too much data.
+	// On macOS: The combination of service, username & password should not exceed ~3000 bytes
+	// On Windows: The service is limited to 32KiB while the password is limited to 2560 bytes
+	ErrSetDataTooBig = xerrors.New("data passed to Set was too big")
+
+	// ErrNotImplemented represents when keyring usage is not implemented on the current
+	// operating system.
+	ErrNotImplemented = xerrors.New("not implemented")
+)
+
+const (
+	// DefaultServiceName is the service name used in keyrings for storing Coder CLI session
+	// tokens.
+	DefaultServiceName = "coder-v2-credentials"
+)
+
+// keyringProvider represents an operating system keyring. The expectation
+// is these methods operate on the user/login keyring.
+type keyringProvider interface {
+	// Set stores the given credential for a service name in the operating system
+	// keyring.
+	Set(service, credential string) error
+	// Get retrieves the credential from the keyring. It must return os.ErrNotExist
+	// if the credential is not found.
+	Get(service string) ([]byte, error)
+	// Delete deletes the credential from the keyring. It must return os.ErrNotExist
+	// if the credential is not found.
+	Delete(service string) error
+}
+
+// credential represents a single credential entry.
+type credential struct {
+	CoderURL string `json:"coder_url"`
+	APIToken string `json:"api_token"`
+}
+
+// credentialsMap represents the JSON structure stored in the operating system keyring.
+// It supports storing multiple credentials for different server URLs.
+type credentialsMap map[string]credential
+
+// normalizeHost returns a normalized version of the URL host for use as a map key.
+func normalizeHost(u *url.URL) (string, error) {
+	if u == nil || u.Host == "" {
+		return "", xerrors.New("nil server URL")
+	}
+	return strings.TrimSpace(strings.ToLower(u.Host)), nil
+}
+
+// parseCredentialsJSON parses the JSON from the keyring into a credentialsMap.
+func parseCredentialsJSON(jsonData []byte) (credentialsMap, error) {
+	if len(jsonData) == 0 {
+		return make(credentialsMap), nil
+	}
+
+	var creds credentialsMap
+	if err := json.Unmarshal(jsonData, &creds); err != nil {
+		return nil, xerrors.Errorf("unmarshal credentials: %w", err)
+	}
+
+	return creds, nil
+}
+
+// Keyring is a Backend that exclusively stores the session token in the operating
+// system keyring. Happy path usage of this type should start with NewKeyring.
+// It stores a JSON object in the keyring that supports multiple credentials for
+// different server URLs, providing compatibility with Coder Desktop and other Coder
+// applications.
+type Keyring struct {
+	provider    keyringProvider
+	serviceName string
+}
+
+// NewKeyringWithService creates a Keyring Backend that stores credentials under the
+// specified service name. Generally, DefaultServiceName should be provided as the service
+// name except in tests which may need parameterization to avoid conflicting keyring use.
+func NewKeyringWithService(serviceName string) Keyring {
+	return Keyring{
+		provider:    operatingSystemKeyring{},
+		serviceName: serviceName,
+	}
+}
+
+func (o Keyring) Read(serverURL *url.URL) (string, error) {
+	host, err := normalizeHost(serverURL)
+	if err != nil {
+		return "", err
+	}
+
+	credJSON, err := o.provider.Get(o.serviceName)
+	if err != nil {
+		return "", err
+	}
+	if len(credJSON) == 0 {
+		return "", os.ErrNotExist
+	}
+
+	creds, err := parseCredentialsJSON(credJSON)
+	if err != nil {
+		return "", xerrors.Errorf("read: parse existing credentials: %w", err)
+	}
+
+	// Return the credential for the specified URL
+	cred, ok := creds[host]
+	if !ok {
+		return "", os.ErrNotExist
+	}
+	return cred.APIToken, nil
+}
+
+func (o Keyring) Write(serverURL *url.URL, token string) error {
+	host, err := normalizeHost(serverURL)
+	if err != nil {
+		return err
+	}
+
+	existingJSON, err := o.provider.Get(o.serviceName)
+	if err != nil && !errors.Is(err, os.ErrNotExist) {
+		return xerrors.Errorf("read existing credentials: %w", err)
+	}
+
+	creds, err := parseCredentialsJSON(existingJSON)
+	if err != nil {
+		return xerrors.Errorf("write: parse existing credentials: %w", err)
+	}
+
+	// Upsert the credential for this URL.
+	creds[host] = credential{
+		CoderURL: host,
+		APIToken: token,
+	}
+
+	credsJSON, err := json.Marshal(creds)
+	if err != nil {
+		return xerrors.Errorf("marshal credentials: %w", err)
+	}
+
+	err = o.provider.Set(o.serviceName, string(credsJSON))
+	if err != nil {
+		return xerrors.Errorf("write credentials to keyring: %w", err)
+	}
+	return nil
+}
+
+func (o Keyring) Delete(serverURL *url.URL) error {
+	host, err := normalizeHost(serverURL)
+	if err != nil {
+		return err
+	}
+
+	existingJSON, err := o.provider.Get(o.serviceName)
+	if err != nil {
+		return err
+	}
+
+	creds, err := parseCredentialsJSON(existingJSON)
+	if err != nil {
+		return xerrors.Errorf("failed to parse existing credentials: %w", err)
+	}
+
+	if _, ok := creds[host]; !ok {
+		return os.ErrNotExist
+	}
+
+	delete(creds, host)
+
+	// Delete the entire keyring entry when no credentials remain.
+	if len(creds) == 0 {
+		return o.provider.Delete(o.serviceName)
+	}
+
+	// Write back the updated credentials map.
+	credsJSON, err := json.Marshal(creds)
+	if err != nil {
+		return xerrors.Errorf("failed to marshal credentials: %w", err)
+	}
+
+	return o.provider.Set(o.serviceName, string(credsJSON))
+}
+
+// File is a Backend that exclusively stores the session token in a file on disk.
+type File struct {
+	config func() config.Root
+}
+
+func NewFile(f func() config.Root) *File {
+	return &File{config: f}
+}
+
+func (f *File) Read(_ *url.URL) (string, error) {
+	return f.config().Session().Read()
+}
+
+func (f *File) Write(_ *url.URL, token string) error {
+	return f.config().Session().Write(token)
+}
+
+func (f *File) Delete(_ *url.URL) error {
+	return f.config().Session().Delete()
+}
@@ -0,0 +1,105 @@
+//go:build darwin
+
+package sessionstore
+
+import (
+	"encoding/base64"
+	"fmt"
+	"io"
+	"os"
+	"os/exec"
+	"regexp"
+	"strings"
+)
+
+const (
+	// fixedUsername is the fixed username used for all keychain entries.
+	// Since our interface only uses service names, we use a constant username.
+	fixedUsername = "coder-login-credentials"
+
+	execPathKeychain = "/usr/bin/security"
+	notFoundStr      = "could not be found"
+)
+
+// operatingSystemKeyring implements keyringProvider for macOS.
+// It is largely adapted from the zalando/go-keyring package.
+type operatingSystemKeyring struct{}
+
+func (operatingSystemKeyring) Set(service, credential string) error {
+	// if the added secret has multiple lines or some non ascii,
+	// macOS will hex encode it on return. To avoid getting garbage, we
+	// encode all passwords
+	password := base64.StdEncoding.EncodeToString([]byte(credential))
+
+	cmd := exec.Command(execPathKeychain, "-i")
+	stdIn, err := cmd.StdinPipe()
+	if err != nil {
+		return err
+	}
+
+	if err = cmd.Start(); err != nil {
+		return err
+	}
+
+	command := fmt.Sprintf("add-generic-password -U -s %s -a %s -w %s\n",
+		shellEscape(service),
+		shellEscape(fixedUsername),
+		shellEscape(password))
+	if len(command) > 4096 {
+		return ErrSetDataTooBig
+	}
+
+	if _, err := io.WriteString(stdIn, command); err != nil {
+		return err
+	}
+
+	if err = stdIn.Close(); err != nil {
+		return err
+	}
+
+	return cmd.Wait()
+}
+
+func (operatingSystemKeyring) Get(service string) ([]byte, error) {
+	out, err := exec.Command(
+		execPathKeychain,
+		"find-generic-password",
+		"-s", service,
+		"-wa", fixedUsername).CombinedOutput()
+	if err != nil {
+		if strings.Contains(string(out), notFoundStr) {
+			return nil, os.ErrNotExist
+		}
+		return nil, err
+	}
+
+	trimStr := strings.TrimSpace(string(out))
+	return base64.StdEncoding.DecodeString(trimStr)
+}
+
+func (operatingSystemKeyring) Delete(service string) error {
+	out, err := exec.Command(
+		execPathKeychain,
+		"delete-generic-password",
+		"-s", service,
+		"-a", fixedUsername).CombinedOutput()
+	if strings.Contains(string(out), notFoundStr) {
+		return os.ErrNotExist
+	}
+	return err
+}
+
+// shellEscape returns a shell-escaped version of the string s.
+// This is adapted from github.com/zalando/go-keyring/internal/shellescape.
+func shellEscape(s string) string {
+	if len(s) == 0 {
+		return "''"
+	}
+
+	pattern := regexp.MustCompile(`[^\w@%+=:,./-]`)
+	if pattern.MatchString(s) {
+		return "'" + strings.ReplaceAll(s, "'", "'\"'\"'") + "'"
+	}
+
+	return s
+}
@@ -0,0 +1,34 @@
+//go:build darwin
+
+package sessionstore_test
+
+import (
+	"encoding/base64"
+	"os/exec"
+	"testing"
+)
+
+const (
+	execPathKeychain = "/usr/bin/security"
+	fixedUsername    = "coder-login-credentials"
+)
+
+func readRawKeychainCredential(t *testing.T, service string) []byte {
+	t.Helper()
+
+	out, err := exec.Command(
+		execPathKeychain,
+		"find-generic-password",
+		"-s", service,
+		"-wa", fixedUsername).CombinedOutput()
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	dst := make([]byte, base64.StdEncoding.DecodedLen(len(out)))
+	n, err := base64.StdEncoding.Decode(dst, out)
+	if err != nil {
+		t.Fatal(err)
+	}
+	return dst[:n]
+}
@@ -0,0 +1,121 @@
+package sessionstore
+
+import (
+	"encoding/json"
+	"net/url"
+	"testing"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestNormalizeHost(t *testing.T) {
+	t.Parallel()
+
+	tests := []struct {
+		name    string
+		url     *url.URL
+		want    string
+		wantErr bool
+	}{
+		{
+			name: "StandardHost",
+			url:  &url.URL{Host: "coder.example.com"},
+			want: "coder.example.com",
+		},
+		{
+			name: "HostWithPort",
+			url:  &url.URL{Host: "coder.example.com:8080"},
+			want: "coder.example.com:8080",
+		},
+		{
+			name: "UppercaseHost",
+			url:  &url.URL{Host: "CODER.EXAMPLE.COM"},
+			want: "coder.example.com",
+		},
+		{
+			name: "HostWithWhitespace",
+			url:  &url.URL{Host: "  coder.example.com  "},
+			want: "coder.example.com",
+		},
+		{
+			name:    "NilURL",
+			url:     nil,
+			want:    "",
+			wantErr: true,
+		},
+		{
+			name:    "EmptyHost",
+			url:     &url.URL{Host: ""},
+			want:    "",
+			wantErr: true,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			t.Parallel()
+			got, err := normalizeHost(tt.url)
+			if tt.wantErr {
+				require.Error(t, err)
+				return
+			}
+			require.NoError(t, err)
+			require.Equal(t, tt.want, got)
+		})
+	}
+}
+
+func TestParseCredentialsJSON(t *testing.T) {
+	t.Parallel()
+
+	t.Run("Empty", func(t *testing.T) {
+		t.Parallel()
+		creds, err := parseCredentialsJSON(nil)
+		require.NoError(t, err)
+		require.NotNil(t, creds)
+		require.Empty(t, creds)
+	})
+
+	t.Run("NewFormat", func(t *testing.T) {
+		t.Parallel()
+		jsonData := []byte(`{
+			"coder1.example.com": {"coder_url": "coder1.example.com", "api_token": "token1"},
+			"coder2.example.com": {"coder_url": "coder2.example.com", "api_token": "token2"}
+		}`)
+		creds, err := parseCredentialsJSON(jsonData)
+		require.NoError(t, err)
+		require.Len(t, creds, 2)
+		require.Equal(t, "token1", creds["coder1.example.com"].APIToken)
+		require.Equal(t, "token2", creds["coder2.example.com"].APIToken)
+	})
+
+	t.Run("InvalidJSON", func(t *testing.T) {
+		t.Parallel()
+		jsonData := []byte(`{invalid json}`)
+		_, err := parseCredentialsJSON(jsonData)
+		require.Error(t, err)
+	})
+}
+
+func TestCredentialsMap_RoundTrip(t *testing.T) {
+	t.Parallel()
+
+	creds := credentialsMap{
+		"coder1.example.com": {
+			CoderURL: "coder1.example.com",
+			APIToken: "token1",
+		},
+		"coder2.example.com:8080": {
+			CoderURL: "coder2.example.com:8080",
+			APIToken: "token2",
+		},
+	}
+
+	jsonData, err := json.Marshal(creds)
+	require.NoError(t, err)
+
+	parsed, err := parseCredentialsJSON(jsonData)
+	require.NoError(t, err)
+
+	require.Equal(t, creds, parsed)
+}
@@ -0,0 +1,17 @@
+//go:build !windows && !darwin
+
+package sessionstore
+
+type operatingSystemKeyring struct{}
+
+func (operatingSystemKeyring) Set(_, _ string) error {
+	return ErrNotImplemented
+}
+
+func (operatingSystemKeyring) Get(_ string) ([]byte, error) {
+	return nil, ErrNotImplemented
+}
+
+func (operatingSystemKeyring) Delete(_ string) error {
+	return ErrNotImplemented
+}
@@ -0,0 +1,10 @@
+//go:build !windows && !darwin
+
+package sessionstore_test
+
+import "testing"
+
+func readRawKeychainCredential(t *testing.T, _ string) []byte {
+	t.Fatal("not implemented")
+	return nil
+}
@@ -0,0 +1,408 @@
+package sessionstore_test
+
+import (
+	"encoding/json"
+	"errors"
+	"fmt"
+	"net/url"
+	"os"
+	"path"
+	"runtime"
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/cli/config"
+	"github.com/coder/coder/v2/cli/sessionstore"
+)
+
+type storedCredentials map[string]struct {
+	CoderURL string `json:"coder_url"`
+	APIToken string `json:"api_token"`
+}
+
+// Generate a test service name for use with the OS keyring. It uses a combination
+// of the test name and a nanosecond timestamp to prevent collisions.
+func keyringTestServiceName(t *testing.T) string {
+	t.Helper()
+	return t.Name() + "_" + fmt.Sprintf("%v", time.Now().UnixNano())
+}
+
+func TestKeyring(t *testing.T) {
+	t.Parallel()
+
+	if runtime.GOOS != "windows" && runtime.GOOS != "darwin" {
+		t.Skip("linux is not supported yet")
+	}
+
+	// This test exercises use of the operating system keyring. As a result,
+	// the operating system keyring is expected to be available.
+
+	const (
+		testURL  = "http://127.0.0.1:1337"
+		testURL2 = "http://127.0.0.1:1338"
+	)
+
+	t.Run("ReadNonExistent", func(t *testing.T) {
+		t.Parallel()
+
+		backend := sessionstore.NewKeyringWithService(keyringTestServiceName(t))
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+		t.Cleanup(func() { _ = backend.Delete(srvURL) })
+
+		_, err = backend.Read(srvURL)
+		require.Error(t, err)
+		require.True(t, os.IsNotExist(err), "expected os.ErrNotExist when reading non-existent token")
+	})
+
+	t.Run("DeleteNonExistent", func(t *testing.T) {
+		t.Parallel()
+
+		backend := sessionstore.NewKeyringWithService(keyringTestServiceName(t))
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+		t.Cleanup(func() { _ = backend.Delete(srvURL) })
+
+		err = backend.Delete(srvURL)
+		require.Error(t, err)
+		require.True(t, errors.Is(err, os.ErrNotExist), "expected os.ErrNotExist when deleting non-existent token")
+	})
+
+	t.Run("WriteAndRead", func(t *testing.T) {
+		t.Parallel()
+
+		backend := sessionstore.NewKeyringWithService(keyringTestServiceName(t))
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+		t.Cleanup(func() { _ = backend.Delete(srvURL) })
+
+		dir := t.TempDir()
+		expSessionFile := path.Join(dir, "session")
+
+		const inputToken = "test-keyring-token-12345"
+		err = backend.Write(srvURL, inputToken)
+		require.NoError(t, err)
+
+		// Verify no session file was created (keyring stores in OS keyring, not file)
+		_, err = os.Stat(expSessionFile)
+		require.True(t, errors.Is(err, os.ErrNotExist), "expected session token file to not exist when using keyring")
+
+		token, err := backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, inputToken, token)
+
+		// Clean up
+		err = backend.Delete(srvURL)
+		require.NoError(t, err)
+	})
+
+	t.Run("WriteAndDelete", func(t *testing.T) {
+		t.Parallel()
+
+		backend := sessionstore.NewKeyringWithService(keyringTestServiceName(t))
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+		t.Cleanup(func() { _ = backend.Delete(srvURL) })
+
+		const inputToken = "test-keyring-token-67890"
+		err = backend.Write(srvURL, inputToken)
+		require.NoError(t, err)
+
+		token, err := backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, inputToken, token)
+
+		err = backend.Delete(srvURL)
+		require.NoError(t, err)
+
+		_, err = backend.Read(srvURL)
+		require.Error(t, err)
+		require.True(t, os.IsNotExist(err), "expected os.ErrNotExist after deleting token")
+	})
+
+	t.Run("OverwriteToken", func(t *testing.T) {
+		t.Parallel()
+
+		backend := sessionstore.NewKeyringWithService(keyringTestServiceName(t))
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+		t.Cleanup(func() { _ = backend.Delete(srvURL) })
+
+		// Write first token
+		const firstToken = "first-keyring-token"
+		err = backend.Write(srvURL, firstToken)
+		require.NoError(t, err)
+
+		token, err := backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, firstToken, token)
+
+		// Overwrite with second token
+		const secondToken = "second-keyring-token"
+		err = backend.Write(srvURL, secondToken)
+		require.NoError(t, err)
+
+		token, err = backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, secondToken, token)
+
+		// Clean up
+		err = backend.Delete(srvURL)
+		require.NoError(t, err)
+	})
+
+	t.Run("MultipleServers", func(t *testing.T) {
+		t.Parallel()
+
+		backend := sessionstore.NewKeyringWithService(keyringTestServiceName(t))
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+		srvURL2, err := url.Parse(testURL2)
+		require.NoError(t, err)
+
+		t.Cleanup(func() {
+			_ = backend.Delete(srvURL)
+			_ = backend.Delete(srvURL2)
+		})
+
+		// Write token for server 1
+		const token1 = "token-for-server-1"
+		err = backend.Write(srvURL, token1)
+		require.NoError(t, err)
+
+		// Write token for server 2 (should NOT overwrite server 1)
+		const token2 = "token-for-server-2"
+		err = backend.Write(srvURL2, token2)
+		require.NoError(t, err)
+
+		// Read server 1's credential
+		token, err := backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, token1, token)
+
+		// Read server 2's credential
+		token, err = backend.Read(srvURL2)
+		require.NoError(t, err)
+		require.Equal(t, token2, token)
+
+		// Delete server 1's credential
+		err = backend.Delete(srvURL)
+		require.NoError(t, err)
+
+		// Verify server 1's credential is gone
+		_, err = backend.Read(srvURL)
+		require.Error(t, err)
+		require.True(t, os.IsNotExist(err))
+
+		// Verify server 2's credential still exists
+		token, err = backend.Read(srvURL2)
+		require.NoError(t, err)
+		require.Equal(t, token2, token)
+
+		// Clean up remaining credentials
+		err = backend.Delete(srvURL2)
+		require.NoError(t, err)
+	})
+
+	t.Run("StorageFormat", func(t *testing.T) {
+		t.Parallel()
+		// The storage format must remain consistent to ensure we don't break
+		// compatibility with other Coder related applications that may read
+		// or decode the same credential.
+
+		const testURL1 = "http://127.0.0.1:1337"
+		srv1URL, err := url.Parse(testURL1)
+		require.NoError(t, err)
+
+		const testURL2 = "http://127.0.0.1:1338"
+		srv2URL, err := url.Parse(testURL2)
+		require.NoError(t, err)
+
+		serviceName := keyringTestServiceName(t)
+		backend := sessionstore.NewKeyringWithService(serviceName)
+		t.Cleanup(func() {
+			_ = backend.Delete(srv1URL)
+			_ = backend.Delete(srv2URL)
+		})
+
+		// Write token for server 1
+		const token1 = "token-server-1"
+		err = backend.Write(srv1URL, token1)
+		require.NoError(t, err)
+
+		// Write token for server 2 (should NOT overwrite server 1's token)
+		const token2 = "token-server-2"
+		err = backend.Write(srv2URL, token2)
+		require.NoError(t, err)
+
+		// Verify both credentials are stored in the raw format and can
+		// be extracted through the Backend API.
+		rawCredential := readRawKeychainCredential(t, serviceName)
+
+		storedCreds := make(storedCredentials)
+		err = json.Unmarshal(rawCredential, &storedCreds)
+		require.NoError(t, err, "unmarshalling stored credentials")
+
+		// Both credentials should exist
+		require.Len(t, storedCreds, 2)
+		require.Equal(t, token1, storedCreds[srv1URL.Host].APIToken)
+		require.Equal(t, token2, storedCreds[srv2URL.Host].APIToken)
+
+		// Read individual credentials
+		token, err := backend.Read(srv1URL)
+		require.NoError(t, err)
+		require.Equal(t, token1, token)
+
+		token, err = backend.Read(srv2URL)
+		require.NoError(t, err)
+		require.Equal(t, token2, token)
+
+		// Cleanup
+		err = backend.Delete(srv1URL)
+		require.NoError(t, err)
+		err = backend.Delete(srv2URL)
+		require.NoError(t, err)
+	})
+}
+
+func TestFile(t *testing.T) {
+	const (
+		testURL  = "http://127.0.0.1:1337"
+		testURL2 = "http://127.0.0.1:1338"
+	)
+
+	t.Parallel()
+
+	t.Run("ReadNonExistent", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		backend := sessionstore.NewFile(func() config.Root { return config.Root(dir) })
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+
+		_, err = backend.Read(srvURL)
+		require.Error(t, err)
+		require.True(t, os.IsNotExist(err))
+	})
+
+	t.Run("WriteAndRead", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		backend := sessionstore.NewFile(func() config.Root { return config.Root(dir) })
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+
+		// Write a token
+		const inputToken = "test-token-12345"
+		err = backend.Write(srvURL, inputToken)
+		require.NoError(t, err)
+
+		// Verify the session file was created
+		sessionFile := config.Root(dir).Session()
+		require.True(t, sessionFile.Exists())
+
+		// Read the token back
+		token, err := backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, inputToken, token)
+	})
+
+	t.Run("WriteAndDelete", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		backend := sessionstore.NewFile(func() config.Root { return config.Root(dir) })
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+
+		// Write a token
+		const inputToken = "test-token-67890"
+		err = backend.Write(srvURL, inputToken)
+		require.NoError(t, err)
+
+		// Verify the token was written
+		token, err := backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, inputToken, token)
+
+		// Delete the token
+		err = backend.Delete(srvURL)
+		require.NoError(t, err)
+
+		// Verify the token is gone
+		_, err = backend.Read(srvURL)
+		require.Error(t, err)
+		require.True(t, os.IsNotExist(err))
+	})
+
+	t.Run("DeleteNonExistent", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		backend := sessionstore.NewFile(func() config.Root { return config.Root(dir) })
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+
+		// Attempt to delete a non-existent token
+		err = backend.Delete(srvURL)
+		require.Error(t, err)
+		require.True(t, os.IsNotExist(err))
+	})
+
+	t.Run("OverwriteToken", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		backend := sessionstore.NewFile(func() config.Root { return config.Root(dir) })
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+
+		// Write first token
+		const firstToken = "first-token"
+		err = backend.Write(srvURL, firstToken)
+		require.NoError(t, err)
+
+		token, err := backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, firstToken, token)
+
+		// Overwrite with second token
+		const secondToken = "second-token"
+		err = backend.Write(srvURL, secondToken)
+		require.NoError(t, err)
+
+		token, err = backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, secondToken, token)
+	})
+
+	t.Run("WriteIgnoresURL", func(t *testing.T) {
+		t.Parallel()
+
+		dir := t.TempDir()
+		backend := sessionstore.NewFile(func() config.Root { return config.Root(dir) })
+		srvURL, err := url.Parse(testURL)
+		require.NoError(t, err)
+		srvURL2, err := url.Parse(testURL2)
+		require.NoError(t, err)
+
+		//nolint:gosec // Write with first URL test token
+		const firstToken = "token-for-url1"
+		err = backend.Write(srvURL, firstToken)
+		require.NoError(t, err)
+
+		//nolint:gosec // Write with second URL - should overwrite
+		const secondToken = "token-for-url2"
+		err = backend.Write(srvURL2, secondToken)
+		require.NoError(t, err)
+
+		// Should have the second token (File backend doesn't differentiate by URL)
+		token, err := backend.Read(srvURL)
+		require.NoError(t, err)
+		require.Equal(t, secondToken, token)
+	})
+}
@@ -0,0 +1,60 @@
+//go:build windows
+
+package sessionstore
+
+import (
+	"errors"
+	"os"
+	"syscall"
+
+	"github.com/danieljoos/wincred"
+)
+
+// operatingSystemKeyring implements keyringProvider and uses Windows Credential Manager.
+// It is largely adapted from the zalando/go-keyring package.
+type operatingSystemKeyring struct{}
+
+func (operatingSystemKeyring) Set(service, credential string) error {
+	// password may not exceed 2560 bytes (https://github.com/jaraco/keyring/issues/540#issuecomment-968329967)
+	if len(credential) > 2560 {
+		return ErrSetDataTooBig
+	}
+
+	// service may not exceed 512 bytes (might need more testing)
+	if len(service) >= 512 {
+		return ErrSetDataTooBig
+	}
+
+	// service may not exceed 32k but problems occur before that
+	// so we limit it to 30k
+	if len(service) > 1024*30 {
+		return ErrSetDataTooBig
+	}
+
+	cred := wincred.NewGenericCredential(service)
+	cred.CredentialBlob = []byte(credential)
+	cred.Persist = wincred.PersistLocalMachine
+	return cred.Write()
+}
+
+func (operatingSystemKeyring) Get(service string) ([]byte, error) {
+	cred, err := wincred.GetGenericCredential(service)
+	if err != nil {
+		if errors.Is(err, syscall.ERROR_NOT_FOUND) {
+			return nil, os.ErrNotExist
+		}
+		return nil, err
+	}
+	return cred.CredentialBlob, nil
+}
+
+func (operatingSystemKeyring) Delete(service string) error {
+	cred, err := wincred.GetGenericCredential(service)
+	if err != nil {
+		if errors.Is(err, syscall.ERROR_NOT_FOUND) {
+			return os.ErrNotExist
+		}
+		return err
+	}
+	return cred.Delete()
+}
@@ -0,0 +1,74 @@
+//go:build windows
+
+package sessionstore_test
+
+import (
+	"encoding/json"
+	"net/url"
+	"os"
+	"testing"
+
+	"github.com/danieljoos/wincred"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/cli/sessionstore"
+)
+
+func readRawKeychainCredential(t *testing.T, serviceName string) []byte {
+	t.Helper()
+
+	winCred, err := wincred.GetGenericCredential(serviceName)
+	if err != nil {
+		t.Fatal(err)
+	}
+	return winCred.CredentialBlob
+}
+
+func TestWindowsKeyring_WriteReadDelete(t *testing.T) {
+	t.Parallel()
+
+	const testURL = "http://127.0.0.1:1337"
+	srvURL, err := url.Parse(testURL)
+	require.NoError(t, err)
+
+	serviceName := keyringTestServiceName(t)
+	backend := sessionstore.NewKeyringWithService(serviceName)
+	t.Cleanup(func() { _ = backend.Delete(srvURL) })
+
+	// Verify no token exists initially
+	_, err = backend.Read(srvURL)
+	require.ErrorIs(t, err, os.ErrNotExist)
+
+	// Write a token
+	const inputToken = "test-token-12345"
+	err = backend.Write(srvURL, inputToken)
+	require.NoError(t, err)
+
+	// Verify the credential is stored in Windows Credential Manager with correct format
+	winCred, err := wincred.GetGenericCredential(serviceName)
+	require.NoError(t, err, "getting windows credential")
+
+	storedCreds := make(storedCredentials)
+	err = json.Unmarshal(winCred.CredentialBlob, &storedCreds)
+	require.NoError(t, err, "unmarshalling stored credentials")
+
+	// Verify the stored values
+	require.Len(t, storedCreds, 1)
+	cred, ok := storedCreds[srvURL.Host]
+	require.True(t, ok, "credential for URL should exist")
+	require.Equal(t, inputToken, cred.APIToken)
+	require.Equal(t, srvURL.Host, cred.CoderURL)
+
+	// Read the token back
+	token, err := backend.Read(srvURL)
+	require.NoError(t, err)
+	require.Equal(t, inputToken, token)
+
+	// Delete the token
+	err = backend.Delete(srvURL)
+	require.NoError(t, err)
+
+	// Verify token is deleted
+	_, err = backend.Read(srvURL)
+	require.ErrorIs(t, err, os.ErrNotExist)
+}
@@ -109,6 +109,51 @@ func (r *RootCmd) ssh() *serpent.Command {
 				}
 			},
 		),
+		CompletionHandler: func(inv *serpent.Invocation) []string {
+			client, err := r.InitClient(inv)
+			if err != nil {
+				return []string{}
+			}
+
+			res, err := client.Workspaces(inv.Context(), codersdk.WorkspaceFilter{
+				Owner: codersdk.Me,
+			})
+			if err != nil {
+				return []string{}
+			}
+
+			var mu sync.Mutex
+			var completions []string
+			var wg sync.WaitGroup
+			for _, ws := range res.Workspaces {
+				wg.Add(1)
+				go func() {
+					defer wg.Done()
+					resources, err := client.TemplateVersionResources(inv.Context(), ws.LatestBuild.TemplateVersionID)
+					if err != nil {
+						return
+					}
+					var agents []codersdk.WorkspaceAgent
+					for _, resource := range resources {
+						agents = append(agents, resource.Agents...)
+					}
+
+					mu.Lock()
+					defer mu.Unlock()
+					if len(agents) == 1 {
+						completions = append(completions, ws.Name)
+					} else {
+						for _, agent := range agents {
+							completions = append(completions, fmt.Sprintf("%s.%s", ws.Name, agent.Name))
+						}
+					}
+				}()
+			}
+			wg.Wait()
+
+			slices.Sort(completions)
+			return completions
+		},
 		Handler: func(inv *serpent.Invocation) (retErr error) {
 			client, err := r.InitClient(inv)
 			if err != nil {
@@ -906,6 +951,8 @@ func GetWorkspaceAndAgent(ctx context.Context, inv *serpent.Invocation, client *
 					return codersdk.Workspace{}, codersdk.WorkspaceAgent{}, nil, xerrors.Errorf("start workspace with active template version: %w", err)
 				}
 				_, _ = fmt.Fprintln(inv.Stdout, "Unable to start the workspace with template version from last build. Your workspace has been updated to the current active template version.")
+			default:
+				return codersdk.Workspace{}, codersdk.WorkspaceAgent{}, nil, xerrors.Errorf("start workspace with current template version: %w", err)
 			}
 		} else if err != nil {
 			return codersdk.Workspace{}, codersdk.WorkspaceAgent{}, nil, xerrors.Errorf("start workspace with current template version: %w", err)
@@ -2447,3 +2447,99 @@ func tempDirUnixSocket(t *testing.T) string {

 	return t.TempDir()
 }
+
+func TestSSH_Completion(t *testing.T) {
+	t.Parallel()
+
+	t.Run("SingleAgent", func(t *testing.T) {
+		t.Parallel()
+
+		client, workspace, agentToken := setupWorkspaceForAgent(t)
+		_ = agenttest.New(t, client.URL, agentToken)
+		coderdtest.AwaitWorkspaceAgents(t, client, workspace.ID)
+
+		var stdout bytes.Buffer
+		inv, root := clitest.New(t, "ssh", "")
+		inv.Stdout = &stdout
+		inv.Environ.Set("COMPLETION_MODE", "1")
+		clitest.SetupConfig(t, client, root)
+
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitMedium)
+		defer cancel()
+
+		err := inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		// For single-agent workspaces, the only completion should be the
+		// bare workspace name.
+		output := stdout.String()
+		t.Logf("Completion output: %q", output)
+		require.Contains(t, output, workspace.Name)
+	})
+
+	t.Run("MultiAgent", func(t *testing.T) {
+		t.Parallel()
+
+		client, store := coderdtest.NewWithDatabase(t, nil)
+		first := coderdtest.CreateFirstUser(t, client)
+		userClient, user := coderdtest.CreateAnotherUserMutators(t, client, first.OrganizationID, nil, func(r *codersdk.CreateUserRequestWithOrgs) {
+			r.Username = "multiuser"
+		})
+
+		r := dbfake.WorkspaceBuild(t, store, database.WorkspaceTable{
+			Name:           "multiworkspace",
+			OrganizationID: first.OrganizationID,
+			OwnerID:        user.ID,
+		}).WithAgent(func(agents []*proto.Agent) []*proto.Agent {
+			return []*proto.Agent{
+				{
+					Name: "agent1",
+					Auth: &proto.Agent_Token{},
+				},
+				{
+					Name: "agent2",
+					Auth: &proto.Agent_Token{},
+				},
+			}
+		}).Do()
+
+		var stdout bytes.Buffer
+		inv, root := clitest.New(t, "ssh", "")
+		inv.Stdout = &stdout
+		inv.Environ.Set("COMPLETION_MODE", "1")
+		clitest.SetupConfig(t, userClient, root)
+
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitMedium)
+		defer cancel()
+
+		err := inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		// For multi-agent workspaces, completions should include the
+		// workspace.agent format but NOT the bare workspace name.
+		output := stdout.String()
+		t.Logf("Completion output: %q", output)
+		lines := strings.Split(strings.TrimSpace(output), "\n")
+		require.NotContains(t, lines, r.Workspace.Name)
+		require.Contains(t, output, r.Workspace.Name+".agent1")
+		require.Contains(t, output, r.Workspace.Name+".agent2")
+	})
+
+	t.Run("NetworkError", func(t *testing.T) {
+		t.Parallel()
+
+		var stdout bytes.Buffer
+		inv, _ := clitest.New(t, "ssh", "")
+		inv.Stdout = &stdout
+		inv.Environ.Set("COMPLETION_MODE", "1")
+
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
+		defer cancel()
+
+		err := inv.WithContext(ctx).Run()
+		require.NoError(t, err)
+
+		output := stdout.String()
+		require.Empty(t, output)
+	})
+}
@@ -5,21 +5,31 @@ import (
 )

 func (r *RootCmd) syncCommand() *serpent.Command {
+	var socketPath string
+
 	cmd := &serpent.Command{
 		Use:   "sync",
-		Short: "Synchronize with the local agent socket",
-		Long:  "Commands for interacting with the local Coder agent via socket communication.",
+		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(),
-			r.syncStart(),
-			r.syncWant(),
-			r.syncComplete(),
-			r.syncWait(),
-			r.syncStatus(),
+			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
 }
@@ -1,50 +1,47 @@
 package cli

 import (
-	"context"
-	"fmt"
-
 	"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"
-
-	"github.com/coder/coder/v2/codersdk/agentsdk"
 )

-func (r *RootCmd) syncComplete() *serpent.Command {
-	return &serpent.Command{
+func (*RootCmd) syncComplete(socketPath *string) *serpent.Command {
+	cmd := &serpent.Command{
 		Use:   "complete <unit>",
-		Short: "Mark a unit as complete in the dependency graph",
-		Long:  "Set a unit's status to complete in the dependency graph.",
+		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 := context.Background()
+			ctx := i.Context()

 			if len(i.Args) != 1 {
 				return xerrors.New("exactly one unit name is required")
 			}
-			unit := i.Args[0]
+			unit := unit.ID(i.Args[0])

-			// Show initial message
-			fmt.Printf("Completing unit '%s'...\n", unit)
+			opts := []agentsocket.Option{}
+			if *socketPath != "" {
+				opts = append(opts, agentsocket.WithPath(*socketPath))
+			}

-			// Connect to agent socket
-			client, err := agentsdk.NewSocketClient(agentsdk.SocketConfig{
-				Path: "/tmp/coder.sock",
-			})
+			client, err := agentsocket.NewClient(ctx, opts...)
 			if err != nil {
 				return xerrors.Errorf("connect to agent socket: %w", err)
 			}
 			defer client.Close()

-			// Complete the unit
 			if err := client.SyncComplete(ctx, unit); err != nil {
 				return xerrors.Errorf("complete unit failed: %w", err)
 			}

-			// Display success message
-			fmt.Printf("Unit '%s' completed successfully\n", unit)
+			cliui.Info(i.Stdout, "Success")

 			return nil
 		},
 	}
+
+	return cmd
 }
@@ -1,53 +1,42 @@
 package cli

 import (
-	"context"
-	"fmt"
-	"time"
-
 	"golang.org/x/xerrors"

+	"github.com/coder/coder/v2/agent/agentsocket"
+	"github.com/coder/coder/v2/cli/cliui"
 	"github.com/coder/serpent"
-
-	"github.com/coder/coder/v2/codersdk/agentsdk"
 )

-func (r *RootCmd) syncPing() *serpent.Command {
-	return &serpent.Command{
+func (*RootCmd) syncPing(socketPath *string) *serpent.Command {
+	cmd := &serpent.Command{
 		Use:   "ping",
-		Short: "Ping the local agent socket",
-		Long:  "Test connectivity to the local Coder agent via socket communication.",
+		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 := context.Background()
+			ctx := i.Context()

-			// Show initial message
-			fmt.Println("Pinging agent socket...")
+			opts := []agentsocket.Option{}
+			if *socketPath != "" {
+				opts = append(opts, agentsocket.WithPath(*socketPath))
+			}

-			// Connect to agent socket
-			client, err := agentsdk.NewSocketClient(agentsdk.SocketConfig{
-				Path: "/tmp/coder.sock",
-			})
+			client, err := agentsocket.NewClient(ctx, opts...)
 			if err != nil {
 				return xerrors.Errorf("connect to agent socket: %w", err)
 			}
 			defer client.Close()

-			// Measure round-trip time
-			start := time.Now()
-			resp, err := client.Ping(ctx)
-			duration := time.Since(start)
-
+			err = client.Ping(ctx)
 			if err != nil {
 				return xerrors.Errorf("ping failed: %w", err)
 			}

-			// Display results
-			fmt.Printf("Response: %s\n", resp.Message)
-			fmt.Printf("Timestamp: %s\n", resp.Timestamp.Format(time.RFC3339))
-			fmt.Printf("Round-trip time: %s\n", duration.Round(time.Microsecond))
-			fmt.Println("Status: healthy")
+			cliui.Info(i.Stdout, "Success")

 			return nil
 		},
 	}
+
+	return cmd
 }
@@ -2,111 +2,89 @@ package cli

 import (
 	"context"
-	"fmt"
 	"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/codersdk/agentsdk"
+	"github.com/coder/coder/v2/cli/cliui"
 )

 const (
-	// SyncPollInterval is the interval between dependency checks for sync start
-	SyncPollInterval = 1 * time.Second
+	syncPollInterval = 1 * time.Second
 )

-func (r *RootCmd) syncStart() *serpent.Command {
+func (*RootCmd) syncStart(socketPath *string) *serpent.Command {
 	var timeout time.Duration

 	cmd := &serpent.Command{
 		Use:   "start <unit>",
-		Short: "Start a unit in the dependency graph",
-		Long:  "Register a unit in the dependency graph and set its status to started. Waits for all dependencies to be satisfied before marking as started.",
+		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 := context.Background()
+			ctx := i.Context()

 			if len(i.Args) != 1 {
 				return xerrors.New("exactly one unit name is required")
 			}
-			unitName := i.Args[0]
+			unitName := unit.ID(i.Args[0])

-			// Set up context with timeout if specified
 			if timeout > 0 {
 				var cancel context.CancelFunc
 				ctx, cancel = context.WithTimeout(ctx, timeout)
 				defer cancel()
 			}

-			// Show initial message
-			fmt.Printf("Starting unit '%s'...\n", unitName)
+			opts := []agentsocket.Option{}
+			if *socketPath != "" {
+				opts = append(opts, agentsocket.WithPath(*socketPath))
+			}

-			// Connect to agent socket
-			client, err := agentsdk.NewSocketClient(agentsdk.SocketConfig{
-				Path: "/tmp/coder.sock",
-			})
+			client, err := agentsocket.NewClient(ctx, opts...)
 			if err != nil {
 				return xerrors.Errorf("connect to agent socket: %w", err)
 			}
 			defer client.Close()

-			// Check if dependencies are satisfied first
-			err = client.SyncReady(ctx, unitName)
+			ready, err := client.SyncReady(ctx, unitName)
 			if err != nil {
-				// Check if it's a "not ready" error (expected if dependencies exist)
-				if xerrors.Is(err, unit.ErrDependenciesNotSatisfied) {
-					// Dependencies exist but aren't satisfied, start polling
-					fmt.Printf("Waiting for dependencies of unit '%s' to be satisfied...\n", unitName)
-
-					// Poll until dependencies are satisfied
-					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:
-							// Check if dependencies are satisfied
-							err := client.SyncReady(ctx, unitName)
-							if err == nil {
-								// Dependencies are satisfied
-								fmt.Printf("Dependencies satisfied, marking unit '%s' as started\n", unitName)
-								break pollLoop
-							}
-
-							// Check if it's still a "not ready" error (expected while waiting)
-							if xerrors.Is(err, unit.ErrDependenciesNotSatisfied) {
-								// Still waiting, continue polling
-								continue
-							}
-
-							// Some other error occurred
-							return xerrors.Errorf("error checking dependencies: %w", err)
-						}
-					}
-				} else {
-					// Some other error occurred
-					return xerrors.Errorf("error checking dependencies: %w", err)
-				}
-			} else {
-				// No dependencies or already satisfied
-				fmt.Printf("Dependencies satisfied, marking unit '%s' as started\n", unitName)
+				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
+						}
+					}
+				}
 			}

-			// Start the unit
 			if err := client.SyncStart(ctx, unitName); err != nil {
 				return xerrors.Errorf("start unit failed: %w", err)
 			}

-			// Display success message
-			fmt.Printf("Unit '%s' started successfully\n", unitName)
+			cliui.Info(i.Stdout, "Success")

 			return nil
 		},
@@ -114,8 +92,9 @@ func (r *RootCmd) syncStart() *serpent.Command {

 	cmd.Options = append(cmd.Options, serpent.Option{
 		Flag:        "timeout",
-		Description: "Maximum time to wait for dependencies (e.g., 30s, 5m). No timeout by default.",
+		Description: "Maximum time to wait for dependencies (e.g., 30s, 5m). 5m by default.",
 		Value:       serpent.DurationOf(&timeout),
+		Default:     "5m",
 	})

 	return cmd
@@ -1,134 +1,88 @@
 package cli

 import (
-	"context"
-	"encoding/json"
 	"fmt"
-	"os"
-	"strings"

 	"golang.org/x/xerrors"

 	"github.com/coder/serpent"

-	"github.com/coder/coder/v2/codersdk/agentsdk"
+	"github.com/coder/coder/v2/agent/agentsocket"
+	"github.com/coder/coder/v2/agent/unit"
+	"github.com/coder/coder/v2/cli/cliui"
 )

-type outputFormat string
-
-const (
-	outputFormatHuman outputFormat = "human"
-	outputFormatJSON  outputFormat = "json"
-	outputFormatDOT   outputFormat = "dot"
-)
-
-func (r *RootCmd) syncStatus() *serpent.Command {
-	var (
-		output    string
-		recursive bool
+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 the status of a unit and its dependencies",
-		Long:  "Display the current status of a unit and information about its dependencies. Supports multiple output formats.",
+		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 := context.Background()
+			ctx := i.Context()

 			if len(i.Args) != 1 {
 				return xerrors.New("exactly one unit name is required")
 			}
-			unit := i.Args[0]
+			unit := unit.ID(i.Args[0])

-			// Connect to agent socket
-			client, err := agentsdk.NewSocketClient(agentsdk.SocketConfig{
-				Path: "/tmp/coder.sock",
-			})
+			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()

-			// Get status information
-			statusResp, err := client.SyncStatus(ctx, unit, recursive)
+			statusResp, err := client.SyncStatus(ctx, unit)
 			if err != nil {
 				return xerrors.Errorf("get status failed: %w", err)
 			}

-			// Output based on format
-			switch outputFormat(output) {
-			case outputFormatJSON:
-				return outputJSON(statusResp)
-			case outputFormatDOT:
-				return outputDOT(statusResp)
-			default: // outputFormatHuman
-				return outputHuman(statusResp)
+			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
 		},
 	}

-	cmd.Options = append(cmd.Options,
-		serpent.Option{
-			Flag:          "output",
-			FlagShorthand: "o",
-			Description:   "Output format: human, json, or dot.",
-			Value:         serpent.EnumOf(&output, "human", "json", "dot"),
-		},
-		serpent.Option{
-			Flag:          "recursive",
-			FlagShorthand: "r",
-			Description:   "Show transitive dependencies and include DOT graph.",
-			Value:         serpent.BoolOf(&recursive),
-		},
-	)
-
+	formatter.AttachOptions(&cmd.Options)
 	return cmd
 }
-
-func outputJSON(statusResp *agentsdk.SyncStatusResponse) error {
-	encoder := json.NewEncoder(os.Stdout)
-	encoder.SetIndent("", "  ")
-	return encoder.Encode(statusResp)
-}
-
-func outputDOT(statusResp *agentsdk.SyncStatusResponse) error {
-	if statusResp.DOT == "" {
-		return xerrors.New("DOT output requires --recursive flag")
-	}
-	fmt.Println(statusResp.DOT)
-	return nil
-}
-
-func outputHuman(statusResp *agentsdk.SyncStatusResponse) error {
-	// Unit status
-	fmt.Printf("Unit: %s\n", statusResp.Unit)
-	fmt.Printf("Status: %s\n", statusResp.Status)
-	fmt.Printf("Ready: %t\n", statusResp.IsReady)
-	fmt.Println()
-
-	// Dependencies
-	if len(statusResp.Dependencies) == 0 {
-		fmt.Println("No dependencies")
-		return nil
-	}
-
-	fmt.Println("Dependencies:")
-	fmt.Println(strings.Repeat("-", 80))
-	fmt.Printf("%-20s %-15s %-15s %-10s\n", "Depends On", "Required", "Current", "Satisfied")
-	fmt.Println(strings.Repeat("-", 80))
-
-	for _, dep := range statusResp.Dependencies {
-		satisfied := "✓"
-		if !dep.IsSatisfied {
-			satisfied = "✗"
-		}
-		fmt.Printf("%-20s %-15s %-15s %-10s\n",
-			dep.DependsOn,
-			dep.RequiredStatus,
-			dep.CurrentStatus,
-			satisfied,
-		)
-	}
-
-	return nil
-}
@@ -1,359 +1,330 @@
+//go:build !windows
+
 package cli_test

 import (
-	"errors"
-	"fmt"
-	"net"
+	"bytes"
+	"context"
 	"os"
-	"strings"
+	"path/filepath"
 	"testing"
 	"time"

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

-	"github.com/coder/coder/v2/agent/unit"
+	"cdr.dev/slog"
+	"github.com/coder/coder/v2/agent/agentsocket"
 	"github.com/coder/coder/v2/cli/clitest"
+	"github.com/coder/coder/v2/testutil"
 )

-// mockAgentSocketServer simulates the agent socket server for testing
-type mockAgentSocketServer struct {
-	listener net.Listener
-	handlers map[string]func(string) (string, error)
+// 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 newMockAgentSocketServer(t *testing.T, socketPath string) *mockAgentSocketServer {
-	listener, err := net.Listen("unix", socketPath)
-	require.NoError(t, err)
+func TestSyncCommands_Golden(t *testing.T) {
+	t.Parallel()

-	server := &mockAgentSocketServer{
-		listener: listener,
-		handlers: make(map[string]func(string) (string, error)),
-	}
+	t.Run("ping", func(t *testing.T) {
+		t.Parallel()
+		path, cleanup := setupSocketServer(t)
+		defer cleanup()

-	// Set up default handlers
-	server.handlers["sync.wait"] = func(unitName string) (string, error) {
-		// Always return dependencies not satisfied to trigger polling
-		return "", unit.ErrDependenciesNotSatisfied
-	}
+		ctx := testutil.Context(t, testutil.WaitShort)

-	server.handlers["sync.start"] = func(unitName string) (string, error) {
-		return "Unit " + unitName + " started successfully", nil
-	}
+		var outBuf bytes.Buffer
+		inv, _ := clitest.New(t, "exp", "sync", "ping", "--socket-path", path)
+		inv.Stdout = &outBuf
+		inv.Stderr = &outBuf

-	go server.serve(t)
-	return server
-}
+		err := inv.WithContext(ctx).Run()
+		require.NoError(t, err)

-func (s *mockAgentSocketServer) serve(t *testing.T) {
-	for {
-		conn, err := s.listener.Accept()
-		if err != nil {
-			if !errors.Is(err, net.ErrClosed) {
-				t.Logf("Accept error: %v", 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
 			}
-			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
 		}

-		go s.handleConnection(t, conn)
-	}
-}
-
-func (s *mockAgentSocketServer) handleConnection(t *testing.T, conn net.Conn) {
-	defer conn.Close()
-
-	// Simple JSON-RPC-like protocol simulation
-	buf := make([]byte, 1024)
-	n, err := conn.Read(buf)
-	if err != nil {
-		t.Logf("Read error: %v", err)
-		return
-	}
-
-	request := string(buf[:n])
-
-	// Parse method from request (simplified)
-	var method string
-	if strings.Contains(request, "sync.wait") {
-		method = "sync.wait"
-	} else if strings.Contains(request, "sync.start") {
-		method = "sync.start"
-	}
-
-	handler, exists := s.handlers[method]
-	if !exists {
-		response := `{"error": {"code": -32601, "message": "Method not found"}}`
-		_, _ = conn.Write([]byte(response))
-		return
-	}
-
-	// Extract unit name from request (simplified)
-	unitName := "test-unit"
-	if strings.Contains(request, "test-unit") {
-		unitName = "test-unit"
-	}
-
-	message, err := handler(unitName)
-	if err != nil {
-		response := fmt.Sprintf(`{"error": {"code": -32603, "message": %q}}`, err.Error())
-		_, _ = conn.Write([]byte(response))
-		return
-	}
-
-	response := fmt.Sprintf(`{"result": {"success": true, "message": %q}}`, message)
-	_, _ = conn.Write([]byte(response))
-}
-
-func (s *mockAgentSocketServer) setHandler(method string, handler func(string) (string, error)) {
-	s.handlers[method] = handler
-}
-
-func (s *mockAgentSocketServer) close() {
-	_ = s.listener.Close()
-}
-
-func TestSyncStartTimeout(t *testing.T) {
-	t.Parallel()
-
-	// Create a unique temporary socket file
-	socketPath := fmt.Sprintf("/tmp/coder-test-%d.sock", time.Now().UnixNano())
-	// Remove existing socket if it exists
-	_ = os.Remove(socketPath)
-	defer func() { _ = os.Remove(socketPath) }()
-
-	// Start mock server
-	server := newMockAgentSocketServer(t, socketPath)
-	defer server.close()
-
-	// Test with a short timeout
-	inv, _ := clitest.New(t, "exp", "sync", "start", "test-unit", "--timeout", "100ms")
-
-	// Override the socket path for this test
-	inv.Args = append(inv.Args, "--agent-socket", socketPath)
-
-	start := time.Now()
-	err := inv.Run()
-	duration := time.Since(start)
-
-	// Should timeout after approximately 100ms
-	assert.Error(t, err)
-	assert.Contains(t, err.Error(), "timeout waiting for dependencies of unit 'test-unit'")
-
-	// Should timeout within a reasonable range (100ms + some buffer for test execution)
-	assert.True(t, duration >= 100*time.Millisecond, "Duration should be at least 100ms, got %v", duration)
-	assert.True(t, duration < 2*time.Second, "Duration should be less than 2s, got %v", duration)
-}
-
-func TestSyncWaitTimeout(t *testing.T) {
-	t.Parallel()
-
-	// Create a unique temporary socket file
-	socketPath := fmt.Sprintf("/tmp/coder-test-%d.sock", time.Now().UnixNano())
-	// Remove existing socket if it exists
-	_ = os.Remove(socketPath)
-	defer func() { _ = os.Remove(socketPath) }()
-
-	// Start mock server
-	server := newMockAgentSocketServer(t, socketPath)
-	defer server.close()
-
-	// Test with a short timeout
-	inv, _ := clitest.New(t, "exp", "sync", "wait", "test-unit", "--timeout", "100ms")
-
-	// Override the socket path for this test
-	inv.Args = append(inv.Args, "--agent-socket", socketPath)
-
-	start := time.Now()
-	err := inv.Run()
-	duration := time.Since(start)
-
-	// Should timeout after approximately 100ms
-	assert.Error(t, err)
-	assert.Contains(t, err.Error(), "timeout waiting for dependencies of unit 'test-unit'")
-
-	// Should timeout within a reasonable range (100ms + some buffer for test execution)
-	assert.True(t, duration >= 100*time.Millisecond, "Duration should be at least 100ms, got %v", duration)
-	assert.True(t, duration < 2*time.Second, "Duration should be less than 2s, got %v", duration)
-}
-
-func TestSyncStartNoTimeout(t *testing.T) {
-	t.Parallel()
-
-	// Create a unique temporary socket file
-	socketPath := fmt.Sprintf("/tmp/coder-test-%d.sock", time.Now().UnixNano())
-	// Remove existing socket if it exists
-	_ = os.Remove(socketPath)
-	defer func() { _ = os.Remove(socketPath) }()
-
-	// Start mock server
-	server := newMockAgentSocketServer(t, socketPath)
-	defer server.close()
-
-	// Set up handler that will eventually succeed
-	callCount := 0
-	server.setHandler("sync.wait", func(unitName string) (string, error) {
-		callCount++
-		if callCount >= 3 {
-			// After 3 calls, dependencies are satisfied
-			return "Dependencies satisfied", nil
-		}
-		return "", unit.ErrDependenciesNotSatisfied
+		clitest.TestGoldenFile(t, "TestSyncCommands_Golden/start_with_dependencies", outBuf.Bytes(), nil)
 	})

-	// Test without timeout - should eventually succeed
-	inv, _ := clitest.New(t, "exp", "sync", "start", "test-unit")
+	t.Run("want", func(t *testing.T) {
+		t.Parallel()
+		path, cleanup := setupSocketServer(t)
+		defer cleanup()

-	// Override the socket path for this test
-	inv.Args = append(inv.Args, "--agent-socket", socketPath)
+		ctx := testutil.Context(t, testutil.WaitShort)

-	start := time.Now()
-	err := inv.Run()
-	duration := time.Since(start)
+		var outBuf bytes.Buffer
+		inv, _ := clitest.New(t, "exp", "sync", "want", "test-unit", "dep-unit", "--socket-path", path)
+		inv.Stdout = &outBuf
+		inv.Stderr = &outBuf

-	// Should succeed after a few polling cycles
-	assert.NoError(t, err)
+		err := inv.WithContext(ctx).Run()
+		require.NoError(t, err)

-	// Should take at least 2 seconds (2 polling cycles at 1s interval)
-	assert.True(t, duration >= 2*time.Second, "Duration should be at least 2s, got %v", duration)
-	assert.True(t, callCount >= 3, "Should have made at least 3 calls, got %d", callCount)
-}
-
-func TestSyncWaitNoTimeout(t *testing.T) {
-	t.Parallel()
-
-	// Create a unique temporary socket file
-	socketPath := fmt.Sprintf("/tmp/coder-test-%d.sock", time.Now().UnixNano())
-	// Remove existing socket if it exists
-	_ = os.Remove(socketPath)
-	defer func() { _ = os.Remove(socketPath) }()
-
-	// Start mock server
-	server := newMockAgentSocketServer(t, socketPath)
-	defer server.close()
-
-	// Set up handler that will eventually succeed
-	callCount := 0
-	server.setHandler("sync.wait", func(unitName string) (string, error) {
-		callCount++
-		if callCount >= 3 {
-			// After 3 calls, dependencies are satisfied
-			return "Dependencies satisfied", nil
-		}
-		return "", unit.ErrDependenciesNotSatisfied
+		clitest.TestGoldenFile(t, "TestSyncCommands_Golden/want_success", outBuf.Bytes(), nil)
 	})

-	// Test without timeout - should eventually succeed
-	inv, _ := clitest.New(t, "exp", "sync", "wait", "test-unit")
+	t.Run("complete", func(t *testing.T) {
+		t.Parallel()
+		path, cleanup := setupSocketServer(t)
+		defer cleanup()

-	// Override the socket path for this test
-	inv.Args = append(inv.Args, "--agent-socket", socketPath)
+		ctx := testutil.Context(t, testutil.WaitShort)

-	start := time.Now()
-	err := inv.Run()
-	duration := time.Since(start)
+		// 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()

-	// Should succeed after a few polling cycles
-	assert.NoError(t, err)
+		var outBuf bytes.Buffer
+		inv, _ := clitest.New(t, "exp", "sync", "complete", "test-unit", "--socket-path", path)
+		inv.Stdout = &outBuf
+		inv.Stderr = &outBuf

-	// Should take at least 2 seconds (2 polling cycles at 1s interval)
-	assert.True(t, duration >= 2*time.Second, "Duration should be at least 2s, got %v", duration)
-	assert.True(t, callCount >= 3, "Should have made at least 3 calls, got %d", callCount)
-}
-
-func TestSyncStartTimeoutWithDifferentValues(t *testing.T) {
-	t.Parallel()
-
-	testCases := []struct {
-		name     string
-		timeout  string
-		expected time.Duration
-	}{
-		{"50ms", "50ms", 50 * time.Millisecond},
-		{"200ms", "200ms", 200 * time.Millisecond},
-		{"500ms", "500ms", 500 * time.Millisecond},
-		{"1s", "1s", 1 * time.Second},
-	}
-
-	for _, tc := range testCases {
-		t.Run(tc.name, func(t *testing.T) {
-			t.Parallel()
-
-			// Create a unique temporary socket file
-			socketPath := fmt.Sprintf("/tmp/coder-test-%d.sock", time.Now().UnixNano())
-			// Remove existing socket if it exists
-			_ = os.Remove(socketPath)
-			defer func() { _ = os.Remove(socketPath) }()
-
-			// Start mock server
-			server := newMockAgentSocketServer(t, socketPath)
-			defer server.close()
-
-			// Test with specified timeout
-			inv, _ := clitest.New(t, "exp", "sync", "start", "test-unit", "--timeout", tc.timeout)
-
-			// Override the socket path for this test
-			inv.Args = append(inv.Args, "--agent-socket", socketPath)
-
-			start := time.Now()
-			err := inv.Run()
-			duration := time.Since(start)
-
-			// Should timeout after approximately the specified duration
-			assert.Error(t, err)
-			assert.Contains(t, err.Error(), "timeout waiting for dependencies of unit 'test-unit'")
-
-			// Should timeout within a reasonable range
-			assert.True(t, duration >= tc.expected, "Duration should be at least %v, got %v", tc.expected, duration)
-			assert.True(t, duration < tc.expected+2*time.Second, "Duration should be less than %v, got %v", tc.expected+2*time.Second, duration)
-		})
-	}
-}
-
-func TestSyncWaitTimeoutWithDifferentValues(t *testing.T) {
-	t.Parallel()
-
-	testCases := []struct {
-		name     string
-		timeout  string
-		expected time.Duration
-	}{
-		{"50ms", "50ms", 50 * time.Millisecond},
-		{"200ms", "200ms", 200 * time.Millisecond},
-		{"500ms", "500ms", 500 * time.Millisecond},
-		{"1s", "1s", 1 * time.Second},
-	}
-
-	for _, tc := range testCases {
-		t.Run(tc.name, func(t *testing.T) {
-			t.Parallel()
-
-			// Create a unique temporary socket file
-			socketPath := fmt.Sprintf("/tmp/coder-test-%d.sock", time.Now().UnixNano())
-			// Remove existing socket if it exists
-			_ = os.Remove(socketPath)
-			defer func() { _ = os.Remove(socketPath) }()
-
-			// Start mock server
-			server := newMockAgentSocketServer(t, socketPath)
-			defer server.close()
-
-			// Test with specified timeout
-			inv, _ := clitest.New(t, "exp", "sync", "wait", "test-unit", "--timeout", tc.timeout)
-
-			// Override the socket path for this test
-			inv.Args = append(inv.Args, "--agent-socket", socketPath)
-
-			start := time.Now()
-			err := inv.Run()
-			duration := time.Since(start)
-
-			// Should timeout after approximately the specified duration
-			assert.Error(t, err)
-			assert.Contains(t, err.Error(), "timeout waiting for dependencies of unit 'test-unit'")
-
-			// Should timeout within a reasonable range
-			assert.True(t, duration >= tc.expected, "Duration should be at least %v, got %v", tc.expected, duration)
-			assert.True(t, duration < tc.expected+2*time.Second, "Duration should be less than %v, got %v", tc.expected+2*time.Second, duration)
-		})
-	}
+		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)
+	})
 }
@@ -1,95 +0,0 @@
-package cli
-
-import (
-	"context"
-	"fmt"
-	"time"
-
-	"golang.org/x/xerrors"
-
-	"github.com/coder/serpent"
-
-	"github.com/coder/coder/v2/agent/unit"
-	"github.com/coder/coder/v2/codersdk/agentsdk"
-)
-
-const (
-	// PollInterval is the interval between dependency checks
-	PollInterval = 1 * time.Second
-)
-
-func (r *RootCmd) syncWait() *serpent.Command {
-	var timeout time.Duration
-
-	cmd := &serpent.Command{
-		Use:   "wait <unit>",
-		Short: "Wait for a unit's dependencies to be satisfied",
-		Long:  "Poll until all dependencies for a unit are met. Exits when dependencies are satisfied or timeout is reached.",
-		Handler: func(i *serpent.Invocation) error {
-			ctx := context.Background()
-
-			if len(i.Args) != 1 {
-				return xerrors.New("exactly one unit name is required")
-			}
-			unitName := i.Args[0]
-
-			// Set up context with timeout if specified
-			if timeout > 0 {
-				var cancel context.CancelFunc
-				ctx, cancel = context.WithTimeout(ctx, timeout)
-				defer cancel()
-			}
-
-			// Show initial message
-			fmt.Printf("Waiting for dependencies of unit '%s' to be satisfied...\n", unitName)
-
-			// Connect to agent socket
-			client, err := agentsdk.NewSocketClient(agentsdk.SocketConfig{
-				Path: "/tmp/coder.sock",
-			})
-			if err != nil {
-				return xerrors.Errorf("connect to agent socket: %w", err)
-			}
-			defer client.Close()
-
-			// Poll until dependencies are satisfied
-			ticker := time.NewTicker(PollInterval)
-			defer ticker.Stop()
-
-			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:
-					// Check if dependencies are satisfied
-					err := client.SyncReady(ctx, unitName)
-					if err == nil {
-						// Dependencies are satisfied
-						fmt.Printf("Dependencies for unit '%s' are now satisfied\n", unitName)
-						return nil
-					}
-
-					// Check if it's a "not ready" error (expected while waiting)
-					if xerrors.Is(err, unit.ErrDependenciesNotSatisfied) {
-						// Still waiting, continue polling
-						continue
-					}
-
-					// Some other error occurred
-					return xerrors.Errorf("error checking dependencies: %w", err)
-				}
-			}
-		},
-	}
-
-	cmd.Options = append(cmd.Options, serpent.Option{
-		Flag:        "timeout",
-		Description: "Maximum time to wait for dependencies (e.g., 30s, 5m). No timeout by default.",
-		Value:       serpent.DurationOf(&timeout),
-	})
-
-	return cmd
-}
@@ -1,51 +1,49 @@
 package cli

 import (
-	"context"
-	"fmt"
-
 	"golang.org/x/xerrors"

 	"github.com/coder/serpent"

-	"github.com/coder/coder/v2/codersdk/agentsdk"
+	"github.com/coder/coder/v2/agent/agentsocket"
+	"github.com/coder/coder/v2/agent/unit"
+	"github.com/coder/coder/v2/cli/cliui"
 )

-func (r *RootCmd) syncWant() *serpent.Command {
-	return &serpent.Command{
+func (*RootCmd) syncWant(socketPath *string) *serpent.Command {
+	cmd := &serpent.Command{
 		Use:   "want <unit> <depends-on>",
-		Short: "Declare a dependency between units",
-		Long:  "Declare that a unit depends on another unit reaching complete status.",
+		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 := context.Background()
+			ctx := i.Context()

 			if len(i.Args) != 2 {
 				return xerrors.New("exactly two arguments are required: unit and depends-on")
 			}
-			unit := i.Args[0]
-			dependsOn := i.Args[1]
+			dependentUnit := unit.ID(i.Args[0])
+			dependsOn := unit.ID(i.Args[1])

-			// Show initial message
-			fmt.Printf("Declaring dependency: '%s' depends on '%s'...\n", unit, dependsOn)
+			opts := []agentsocket.Option{}
+			if *socketPath != "" {
+				opts = append(opts, agentsocket.WithPath(*socketPath))
+			}

-			// Connect to agent socket
-			client, err := agentsdk.NewSocketClient(agentsdk.SocketConfig{
-				Path: "/tmp/coder.sock",
-			})
+			client, err := agentsocket.NewClient(ctx, opts...)
 			if err != nil {
 				return xerrors.Errorf("connect to agent socket: %w", err)
 			}
 			defer client.Close()

-			// Declare the dependency
-			if err := client.SyncWant(ctx, unit, dependsOn); err != nil {
+			if err := client.SyncWant(ctx, dependentUnit, dependsOn); err != nil {
 				return xerrors.Errorf("declare dependency failed: %w", err)
 			}

-			// Display success message
-			fmt.Printf("Dependency declared: '%s' now depends on '%s'\n", unit, dependsOn)
+			cliui.Info(i.Stdout, "Success")

 			return nil
 		},
 	}
+
+	return cmd
 }
@@ -1,8 +0,0 @@
-package cli_test
-
-import (
-	"testing"
-)
-
-func TestSyncWant(t *testing.T) {
-}
@@ -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(
@@ -56,20 +56,15 @@ func TestExpTaskDelete(t *testing.T) {
 				taskID := uuid.MustParse(id1)
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch {
-					case r.Method == http.MethodGet && r.URL.Path == "/api/experimental/tasks" && r.URL.Query().Get("q") == "owner:\"me\"":
+					case r.Method == http.MethodGet && r.URL.Path == "/api/v2/tasks/me/exists":
 						c.nameResolves.Add(1)
-						httpapi.Write(r.Context(), w, http.StatusOK, struct {
-							Tasks []codersdk.Task `json:"tasks"`
-							Count int             `json:"count"`
-						}{
-							Tasks: []codersdk.Task{{
+						httpapi.Write(r.Context(), w, http.StatusOK,
+							codersdk.Task{
 								ID:        taskID,
 								Name:      "exists",
 								OwnerName: "me",
-							}},
-							Count: 1,
-						})
-					case r.Method == http.MethodDelete && r.URL.Path == "/api/experimental/tasks/me/"+id1:
+							})
+					case r.Method == http.MethodDelete && r.URL.Path == "/api/v2/tasks/me/"+id1:
 						c.deleteCalls.Add(1)
 						w.WriteHeader(http.StatusAccepted)
 					default:
@@ -87,13 +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:
@@ -107,32 +102,26 @@ func TestExpTaskDelete(t *testing.T) {
 			name: "Multiple_YesFlag",
 			args: []string{"--yes", "first", id4},
 			buildHandler: func(c *testCounters) http.HandlerFunc {
-				firstID := uuid.MustParse(id3)
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch {
-					case r.Method == http.MethodGet && r.URL.Path == "/api/experimental/tasks" && r.URL.Query().Get("q") == "owner:\"me\"":
+					case r.Method == http.MethodGet && r.URL.Path == "/api/v2/tasks/me/first":
 						c.nameResolves.Add(1)
-						httpapi.Write(r.Context(), w, http.StatusOK, struct {
-							Tasks []codersdk.Task `json:"tasks"`
-							Count int             `json:"count"`
-						}{
-							Tasks: []codersdk.Task{{
-								ID:        firstID,
-								Name:      "first",
-								OwnerName: "me",
-							}},
-							Count: 1,
+						httpapi.Write(r.Context(), w, http.StatusOK, codersdk.Task{
+							ID:        uuid.MustParse(id3),
+							Name:      "first",
+							OwnerName: "me",
 						})
-					case r.Method == http.MethodGet && r.URL.Path == "/api/experimental/tasks/me/"+id4:
+					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-2",
+							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:
@@ -141,7 +130,7 @@ func TestExpTaskDelete(t *testing.T) {
 				}
 			},
 			wantDeleteCalls:    2,
-			wantNameResolves:   1,
+			wantNameResolves:   2,
 			wantDeletedMessage: 2,
 		},
 		{
@@ -151,7 +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"`
@@ -174,20 +163,14 @@ func TestExpTaskDelete(t *testing.T) {
 				taskID := uuid.MustParse(id5)
 				return func(w http.ResponseWriter, r *http.Request) {
 					switch {
-					case r.Method == http.MethodGet && r.URL.Path == "/api/experimental/tasks" && r.URL.Query().Get("q") == "owner:\"me\"":
+					case r.Method == http.MethodGet && r.URL.Path == "/api/v2/tasks/me/bad":
 						c.nameResolves.Add(1)
-						httpapi.Write(r.Context(), w, http.StatusOK, struct {
-							Tasks []codersdk.Task `json:"tasks"`
-							Count int             `json:"count"`
-						}{
-							Tasks: []codersdk.Task{{
-								ID:        taskID,
-								Name:      "bad",
-								OwnerName: "me",
-							}},
-							Count: 1,
+						httpapi.Write(r.Context(), w, http.StatusOK, codersdk.Task{
+							ID:        taskID,
+							Name:      "bad",
+							OwnerName: "me",
 						})
-					case r.Method == http.MethodDelete && r.URL.Path == "/api/experimental/tasks/me/"+id5:
+					case r.Method == http.MethodDelete && r.URL.Path == "/api/v2/tasks/me/bad":
 						httpapi.InternalServerError(w, xerrors.New("boom"))
 					default:
 						httpapi.InternalServerError(w, xerrors.New("unwanted path: "+r.Method+" "+r.URL.Path))
@@ -210,7 +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),
 			})
@@ -2,7 +2,6 @@ package cli_test

 import (
 	"bytes"
-	"context"
 	"database/sql"
 	"encoding/json"
 	"io"
@@ -19,10 +18,7 @@ import (
 	"github.com/coder/coder/v2/cli/clitest"
 	"github.com/coder/coder/v2/coderd/coderdtest"
 	"github.com/coder/coder/v2/coderd/database"
-	"github.com/coder/coder/v2/coderd/database/dbauthz"
 	"github.com/coder/coder/v2/coderd/database/dbfake"
-	"github.com/coder/coder/v2/coderd/database/dbgen"
-	"github.com/coder/coder/v2/coderd/database/dbtime"
 	"github.com/coder/coder/v2/coderd/util/slice"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/pty/ptytest"
@@ -43,76 +39,22 @@ func makeAITask(t *testing.T, db database.Store, orgID, adminID, ownerID uuid.UU
 			},
 		}).Do()

-	ws := database.WorkspaceTable{
+	build := dbfake.WorkspaceBuild(t, db, database.WorkspaceTable{
 		OrganizationID: orgID,
 		OwnerID:        ownerID,
 		TemplateID:     tv.Template.ID,
-	}
-	build := dbfake.WorkspaceBuild(t, db, ws).
+	}).
 		Seed(database.WorkspaceBuild{
 			TemplateVersionID: tv.TemplateVersion.ID,
 			Transition:        transition,
-		}).WithAgent().Do()
-	dbgen.WorkspaceBuildParameters(t, db, []database.WorkspaceBuildParameter{
-		{
-			WorkspaceBuildID: build.Build.ID,
-			Name:             codersdk.AITaskPromptParameterName,
-			Value:            prompt,
-		},
-	})
-	agents, err := db.GetWorkspaceAgentsByWorkspaceAndBuildNumber(
-		dbauthz.AsSystemRestricted(context.Background()),
-		database.GetWorkspaceAgentsByWorkspaceAndBuildNumberParams{
-			WorkspaceID: build.Workspace.ID,
-			BuildNumber: build.Build.BuildNumber,
-		},
-	)
-	require.NoError(t, err)
-	require.NotEmpty(t, agents)
-	agentID := agents[0].ID
+		}).
+		WithAgent().
+		WithTask(database.TaskTable{
+			Prompt: prompt,
+		}, nil).
+		Do()

-	// Create a workspace app and set it as the sidebar app.
-	app := dbgen.WorkspaceApp(t, db, database.WorkspaceApp{
-		AgentID:     agentID,
-		Slug:        "task-sidebar",
-		DisplayName: "Task Sidebar",
-		External:    false,
-	})
-
-	// Update build flags to reference the sidebar app and HasAITask=true.
-	err = db.UpdateWorkspaceBuildFlagsByID(
-		dbauthz.AsSystemRestricted(context.Background()),
-		database.UpdateWorkspaceBuildFlagsByIDParams{
-			ID:               build.Build.ID,
-			HasAITask:        sql.NullBool{Bool: true, Valid: true},
-			HasExternalAgent: sql.NullBool{Bool: false, Valid: false},
-			SidebarAppID:     uuid.NullUUID{UUID: app.ID, Valid: true},
-			UpdatedAt:        build.Build.UpdatedAt,
-		},
-	)
-	require.NoError(t, err)
-
-	// Create a task record in the tasks table for the new data model.
-	task := dbgen.Task(t, db, database.TaskTable{
-		OrganizationID:     orgID,
-		OwnerID:            ownerID,
-		Name:               build.Workspace.Name,
-		WorkspaceID:        uuid.NullUUID{UUID: build.Workspace.ID, Valid: true},
-		TemplateVersionID:  tv.TemplateVersion.ID,
-		TemplateParameters: []byte("{}"),
-		Prompt:             prompt,
-		CreatedAt:          dbtime.Now(),
-	})
-
-	// Link the task to the workspace app.
-	dbgen.TaskWorkspaceApp(t, db, database.TaskWorkspaceApp{
-		TaskID:               task.ID,
-		WorkspaceBuildNumber: build.Build.BuildNumber,
-		WorkspaceAgentID:     uuid.NullUUID{UUID: agentID, Valid: true},
-		WorkspaceAppID:       uuid.NullUUID{UUID: app.ID, Valid: true},
-	})
-
-	return task
+	return build.Task
 }

 func TestExpTaskList(t *testing.T) {
@@ -127,7 +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)
@@ -151,7 +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)
@@ -180,7 +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)
@@ -211,7 +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)

@@ -238,7 +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)
@@ -282,7 +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)

@@ -310,7 +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()
--- a/Show More
+++ b/Show More