feat: add AI Bridge Proxy support to copilot module (#725)

## Description

Add AI Bridge Proxy support to the copilot module. When enabled, the module configures proxy environment variables (`HTTPS_PROXY`, `NODE_EXTRA_CA_CERTS`) scoped to the copilot process tree (agentapi and copilot), routing Copilot traffic through AI Bridge Proxy without affecting other workspace traffic.

GitHub authentication is still required, the proxy authenticates with AI Bridge using the Coder session token but does not replace GitHub authentication.

Note: Uses [coder exp sync](https://coder.com/docs/admin/templates/startup-coordination) for startup coordination, ensuring the copilot module waits for the `aibridge-proxy` setup to complete before starting.

## Type of Change

- [ ] New module
- [ ] New template
- [ ] Bug fix
- [x] Feature/enhancement
- [ ] Documentation
- [ ] Other

## Module Information

**Path:** `registry/coder-labs/modules/copilot`  
**New version:** `v0.4.0`  
**Breaking change:** [ ] Yes [x] No

## Testing & Validation

- [x] Tests pass (`bun test`)
- [x] Code formatted (`bun fmt`)
- [x] Changes tested locally

## Related Issues

Depends on: #721
Related to: https://github.com/coder/internal/issues/1187

registry/coder-labs/modules/copilot/README.md

@@ -3,7 +3,7 @@ display_name: Copilot CLI
 description: GitHub Copilot CLI agent for AI-powered terminal assistance
 icon: ../../../../.icons/github.svg
 verified: false
-tags: [agent, copilot, ai, github, tasks]
+tags: [agent, copilot, ai, github, tasks, aibridge]
 ---
 
 # Copilot
@@ -13,7 +13,7 @@ Run [GitHub Copilot CLI](https://docs.github.com/copilot/concepts/agents/about-c
 ```tf
 module "copilot" {
   source   = "registry.coder.com/coder-labs/copilot/coder"
-  version  = "0.3.0"
+  version  = "0.4.0"
   agent_id = coder_agent.example.id
   workdir  = "/home/coder/projects"
 }
@@ -51,7 +51,7 @@ data "coder_parameter" "ai_prompt" {
 
 module "copilot" {
   source   = "registry.coder.com/coder-labs/copilot/coder"
-  version  = "0.3.0"
+  version  = "0.4.0"
   agent_id = coder_agent.example.id
   workdir  = "/home/coder/projects"
 
@@ -71,7 +71,7 @@ Customize tool permissions, MCP servers, and Copilot settings:
 ```tf
 module "copilot" {
   source   = "registry.coder.com/coder-labs/copilot/coder"
-  version  = "0.3.0"
+  version  = "0.4.0"
   agent_id = coder_agent.example.id
   workdir  = "/home/coder/projects"
 
@@ -142,7 +142,7 @@ variable "github_token" {
 
 module "copilot" {
   source       = "registry.coder.com/coder-labs/copilot/coder"
-  version      = "0.3.0"
+  version      = "0.4.0"
   agent_id     = coder_agent.example.id
   workdir      = "/home/coder/projects"
   github_token = var.github_token
@@ -156,7 +156,7 @@ Run Copilot as a command-line tool without task reporting or web interface. This
 ```tf
 module "copilot" {
   source       = "registry.coder.com/coder-labs/copilot/coder"
-  version      = "0.3.0"
+  version      = "0.4.0"
   agent_id     = coder_agent.example.id
   workdir      = "/home/coder"
   report_tasks = false
@@ -164,6 +164,39 @@ module "copilot" {
 }
 ```
 
+### Usage with AI Bridge Proxy
+
+[AI Bridge Proxy](https://coder.com/docs/ai-coder/ai-bridge/ai-bridge-proxy) routes Copilot traffic through [AI Bridge](https://coder.com/docs/ai-coder/ai-bridge) for centralized LLM management and governance.
+The proxy environment variables are scoped to the Copilot process only and do not affect other workspace traffic.
+
+```tf
+module "aibridge-proxy" {
+  source    = "registry.coder.com/coder/aibridge-proxy/coder"
+  version   = "1.0.0"
+  agent_id  = coder_agent.main.id
+  proxy_url = "https://aiproxy.example.com"
+}
+
+module "copilot" {
+  source                   = "registry.coder.com/coder-labs/copilot/coder"
+  version                  = "0.4.0"
+  agent_id                 = coder_agent.main.id
+  workdir                  = "/home/coder/projects"
+  enable_aibridge_proxy    = true
+  aibridge_proxy_auth_url  = module.aibridge-proxy.proxy_auth_url
+  aibridge_proxy_cert_path = module.aibridge-proxy.cert_path
+}
+```
+
+> [!NOTE]
+> AI Bridge Proxy is a Premium Coder feature that requires [AI Governance Add-On](https://coder.com/docs/ai-coder/ai-governance).
+> See the [AI Bridge Proxy setup guide](https://coder.com/docs/ai-coder/ai-bridge/ai-bridge-proxy/setup) for details on configuring the proxy on your Coder deployment.
+> GitHub authentication is still required for Copilot as the proxy authenticates with AI Bridge using the Coder session token, but does not replace GitHub authentication.
+
+> [!IMPORTANT]
+> When using AI Bridge Proxy, enable [startup coordination](https://coder.com/docs/admin/templates/startup-coordination) by setting `CODER_AGENT_SOCKET_SERVER_ENABLED=true` in the workspace container environment.
+> This ensures the Copilot module waits for the `aibridge-proxy` module to complete before starting. Without it, the Copilot start script may fail if the AI Bridge Proxy setup has not completed in time.
+
 ## Authentication
 
 The module supports multiple authentication methods (in priority order):

registry/coder-labs/modules/copilot/copilot.tftest.hcl

@@ -234,3 +234,116 @@ run "app_slug_is_consistent" {
     error_message = "module_dir_name should be '.copilot-module'"
   }
 }
+
+run "aibridge_proxy_defaults" {
+  command = plan
+
+  variables {
+    agent_id = "test-agent"
+    workdir  = "/home/coder"
+  }
+
+  assert {
+    condition     = var.enable_aibridge_proxy == false
+    error_message = "enable_aibridge_proxy should default to false"
+  }
+
+  assert {
+    condition     = var.aibridge_proxy_auth_url == null
+    error_message = "aibridge_proxy_auth_url should default to null"
+  }
+
+  assert {
+    condition     = var.aibridge_proxy_cert_path == null
+    error_message = "aibridge_proxy_cert_path should default to null"
+  }
+}
+
+run "aibridge_proxy_enabled" {
+  command = plan
+
+  variables {
+    agent_id                 = "test-agent-aibridge-proxy"
+    workdir                  = "/home/coder"
+    enable_aibridge_proxy    = true
+    aibridge_proxy_auth_url  = "https://coder:mock-token@aiproxy.example.com"
+    aibridge_proxy_cert_path = "/tmp/aibridge-proxy/ca-cert.pem"
+  }
+
+  assert {
+    condition     = var.enable_aibridge_proxy == true
+    error_message = "AI Bridge Proxy should be enabled"
+  }
+
+  assert {
+    condition     = var.aibridge_proxy_auth_url == "https://coder:mock-token@aiproxy.example.com"
+    error_message = "AI Bridge Proxy auth URL should match the input variable"
+  }
+
+  assert {
+    condition     = var.aibridge_proxy_cert_path == "/tmp/aibridge-proxy/ca-cert.pem"
+    error_message = "AI Bridge Proxy cert path should match the input variable"
+  }
+}
+
+run "aibridge_proxy_validation_missing_proxy_auth_url" {
+  command = plan
+
+  variables {
+    agent_id                 = "test-agent-validation"
+    workdir                  = "/home/coder"
+    enable_aibridge_proxy    = true
+    aibridge_proxy_auth_url  = ""
+    aibridge_proxy_cert_path = "/tmp/aibridge-proxy/ca-cert.pem"
+  }
+
+  expect_failures = [
+    var.enable_aibridge_proxy,
+  ]
+}
+
+run "aibridge_proxy_validation_missing_cert_path" {
+  command = plan
+
+  variables {
+    agent_id                 = "test-agent-validation"
+    workdir                  = "/home/coder"
+    enable_aibridge_proxy    = true
+    aibridge_proxy_auth_url  = "https://coder:mock-token@aiproxy.example.com"
+    aibridge_proxy_cert_path = ""
+  }
+
+  expect_failures = [
+    var.enable_aibridge_proxy,
+  ]
+}
+
+run "aibridge_proxy_with_copilot_config" {
+  command = plan
+
+  variables {
+    agent_id                 = "test-agent"
+    workdir                  = "/home/coder"
+    copilot_model            = "gpt-5"
+    github_token             = "ghp_test123"
+    allow_all_tools          = true
+    enable_aibridge_proxy    = true
+    aibridge_proxy_auth_url  = "https://coder:mock-token@aiproxy.example.com"
+    aibridge_proxy_cert_path = "/tmp/aibridge-proxy/ca-cert.pem"
+  }
+
+  assert {
+    condition     = var.enable_aibridge_proxy == true
+    error_message = "AI Bridge Proxy should be enabled"
+  }
+
+  assert {
+    condition     = length(resource.coder_env.github_token) == 1
+    error_message = "github_token environment variable should be set alongside proxy"
+  }
+
+  assert {
+    condition     = length(resource.coder_env.copilot_model) == 1
+    error_message = "copilot_model environment variable should be set alongside proxy"
+  }
+}

registry/coder-labs/modules/copilot/main.tf

@@ -1,5 +1,5 @@
 terraform {
-  required_version = ">= 1.0"
+  required_version = ">= 1.9"
   required_providers {
     coder = {
       source  = "coder/coder"
@@ -173,6 +173,35 @@ variable "post_install_script" {
   default     = null
 }
 
+variable "enable_aibridge_proxy" {
+  type        = bool
+  description = "Route Copilot traffic through AI Bridge Proxy. See https://coder.com/docs/ai-coder/ai-bridge/ai-bridge-proxy"
+  default     = false
+
+  validation {
+    condition     = !var.enable_aibridge_proxy || (var.aibridge_proxy_auth_url != null && length(var.aibridge_proxy_auth_url) > 0)
+    error_message = "aibridge_proxy_auth_url is required when enable_aibridge_proxy is true."
+  }
+
+  validation {
+    condition     = !var.enable_aibridge_proxy || (var.aibridge_proxy_cert_path != null && length(var.aibridge_proxy_cert_path) > 0)
+    error_message = "aibridge_proxy_cert_path is required when enable_aibridge_proxy is true."
+  }
+}
+
+variable "aibridge_proxy_auth_url" {
+  type        = string
+  description = "AI Bridge Proxy URL with authentication. Use the proxy_auth_url output from the aibridge-proxy module."
+  default     = null
+  sensitive   = true
+}
+
+variable "aibridge_proxy_cert_path" {
+  type        = string
+  description = "Path to the AI Bridge Proxy CA certificate. Use the cert_path output from the aibridge-proxy module."
+  default     = null
+}
+
 data "coder_workspace" "me" {}
 data "coder_workspace_owner" "me" {}
 
@@ -279,6 +308,9 @@ module "agentapi" {
     ARG_TRUSTED_DIRECTORIES='${join(",", var.trusted_directories)}' \
     ARG_EXTERNAL_AUTH_ID='${var.external_auth_id}' \
     ARG_RESUME_SESSION='${var.resume_session}' \
+    ARG_ENABLE_AIBRIDGE_PROXY='${var.enable_aibridge_proxy}' \
+    ARG_AIBRIDGE_PROXY_AUTH_URL='${var.aibridge_proxy_auth_url != null ? var.aibridge_proxy_auth_url : ""}' \
+    ARG_AIBRIDGE_PROXY_CERT_PATH='${var.aibridge_proxy_cert_path != null ? var.aibridge_proxy_cert_path : ""}' \
     /tmp/start.sh
   EOT
 

registry/coder-labs/modules/copilot/scripts/start.sh

@@ -22,6 +22,9 @@ ARG_DENY_TOOLS=${ARG_DENY_TOOLS:-}
 ARG_TRUSTED_DIRECTORIES=${ARG_TRUSTED_DIRECTORIES:-}
 ARG_EXTERNAL_AUTH_ID=${ARG_EXTERNAL_AUTH_ID:-github}
 ARG_RESUME_SESSION=${ARG_RESUME_SESSION:-true}
+ARG_ENABLE_AIBRIDGE_PROXY=${ARG_ENABLE_AIBRIDGE_PROXY:-false}
+ARG_AIBRIDGE_PROXY_AUTH_URL=${ARG_AIBRIDGE_PROXY_AUTH_URL:-}
+ARG_AIBRIDGE_PROXY_CERT_PATH=${ARG_AIBRIDGE_PROXY_CERT_PATH:-}
 
 validate_copilot_installation() {
   if ! command_exists copilot; then
@@ -118,6 +121,48 @@ setup_github_authentication() {
   return 0
 }
 
+setup_aibridge_proxy() {
+  if [ "$ARG_ENABLE_AIBRIDGE_PROXY" != "true" ]; then
+    return 0
+  fi
+
+  echo "Setting up AI Bridge Proxy..."
+
+  # Wait for the aibridge-proxy module to finish.
+  # Uses startup coordination to block until aibridge-proxy-setup signals completion.
+  if command -v coder > /dev/null 2>&1; then
+    coder exp sync want "copilot-aibridge" "aibridge-proxy-setup" > /dev/null 2>&1 || true
+    coder exp sync start "copilot-aibridge" > /dev/null 2>&1 || true
+    trap 'coder exp sync complete "copilot-aibridge" > /dev/null 2>&1 || true' EXIT
+  fi
+
+  if [ -z "$ARG_AIBRIDGE_PROXY_AUTH_URL" ]; then
+    echo "ERROR: AI Bridge Proxy is enabled but no proxy auth URL provided."
+    exit 1
+  fi
+
+  if [ -z "$ARG_AIBRIDGE_PROXY_CERT_PATH" ]; then
+    echo "ERROR: AI Bridge Proxy is enabled but no certificate path provided."
+    exit 1
+  fi
+
+  if [ ! -f "$ARG_AIBRIDGE_PROXY_CERT_PATH" ]; then
+    echo "ERROR: AI Bridge Proxy certificate not found at $ARG_AIBRIDGE_PROXY_CERT_PATH."
+    echo "  Ensure the aibridge-proxy module has successfully completed setup."
+    exit 1
+  fi
+
+  # Set proxy environment variables scoped to this process tree only.
+  # These are inherited by the agentapi/copilot process below,
+  # but do not affect other workspace processes, avoiding routing
+  # unnecessary traffic through the proxy.
+  export HTTPS_PROXY="$ARG_AIBRIDGE_PROXY_AUTH_URL"
+  export NODE_EXTRA_CA_CERTS="$ARG_AIBRIDGE_PROXY_CERT_PATH"
+
+  echo "✓ AI Bridge Proxy configured"
+  echo "  CA certificate: $ARG_AIBRIDGE_PROXY_CERT_PATH"
+}
+
 start_agentapi() {
   echo "Starting in directory: $ARG_WORKDIR"
   cd "$ARG_WORKDIR"
@@ -157,5 +202,6 @@ start_agentapi() {
 }
 
 setup_github_authentication
+setup_aibridge_proxy
 validate_copilot_installation
 start_agentapi

registry/coder/modules/aibridge-proxy/README.md

@@ -0,0 +1,89 @@
+---
+display_name: AI Bridge Proxy
+description: Configure a workspace to route AI tool traffic through AI Bridge via AI Bridge Proxy.
+icon: ../../../../.icons/coder.svg
+verified: true
+tags: [helper, aibridge]
+---
+
+# AI Bridge Proxy
+
+This module configures a Coder workspace to use [AI Bridge Proxy](https://coder.com/docs/ai-coder/ai-bridge/ai-bridge-proxy).
+It downloads the proxy's CA certificate from the Coder deployment and provides Terraform outputs (`proxy_auth_url` and `cert_path`) that tool-specific modules can use to route their traffic through the proxy.
+
+```tf
+module "aibridge-proxy" {
+  source    = "registry.coder.com/coder/aibridge-proxy/coder"
+  version   = "1.0.0"
+  agent_id  = coder_agent.main.id
+  proxy_url = "https://aiproxy.example.com"
+}
+```
+
+> [!NOTE]
+> AI Bridge Proxy is a Premium Coder feature that requires [AI Governance Add-On](https://coder.com/docs/ai-coder/ai-governance).
+> See the [AI Bridge Proxy setup guide](https://coder.com/docs/ai-coder/ai-bridge/ai-bridge-proxy/setup) for details on configuring the proxy on your Coder deployment.
+
+## How it works
+
+[AI Bridge Proxy](https://coder.com/docs/ai-coder/ai-bridge/ai-bridge-proxy) is an HTTP proxy that intercepts traffic to AI providers and forwards it through [AI Bridge](https://coder.com/docs/ai-coder/ai-bridge), enabling centralized LLM management, governance, and cost tracking.
+Any process with the proxy environment variables set will route **all** its traffic through the proxy.
+
+This module **does not** set proxy environment variables globally on the workspace.
+Instead, it provides Terraform outputs (`proxy_auth_url` and `cert_path`) that tool-specific modules consume to configure proxy routing.
+See the [Copilot module](https://registry.coder.com/modules/coder-labs/copilot) for a working integration example.
+
+It is recommended that tool modules scope the proxy environment variables to their own process rather than setting them globally on the workspace, to avoid routing unnecessary traffic through the proxy.
+
+> [!WARNING]
+> If the setup script fails (e.g. the proxy is unreachable), the workspace will still start but the agent will report a startup script error.
+> Tools that depend on the proxy will not work until the issue is resolved. Check the workspace build logs for details.
+
+## Startup Coordination
+
+When used with tool-specific modules (e.g. [Copilot](https://registry.coder.com/modules/coder-labs/copilot)),
+the setup script signals completion via [`coder exp sync`](https://coder.com/docs/admin/templates/startup-coordination) so dependent modules can wait for the `aibridge-proxy` module to complete before starting.
+
+Dependent modules are unblocked once the setup script finishes, regardless of success or failure.
+If the setup fails, dependent modules are expected to detect the failure and handle the error accordingly.
+
+To enable startup coordination, set `CODER_AGENT_SOCKET_SERVER_ENABLED=true` in the workspace container environment:
+
+```hcl
+env = [
+  "CODER_AGENT_TOKEN=${coder_agent.main.token}",
+  "CODER_AGENT_SOCKET_SERVER_ENABLED=true",
+]
+```
+
+> [!NOTE]
+> [Startup coordination](https://coder.com/docs/admin/templates/startup-coordination) requires Coder >= v2.30.
+> Without it, the sync calls are skipped gracefully but dependent modules may fail to start if the `aibridge-proxy` setup has not completed in time.
+
+## Examples
+
+### Custom certificate path
+
+```tf
+module "aibridge-proxy" {
+  source    = "registry.coder.com/coder/aibridge-proxy/coder"
+  version   = "1.0.0"
+  agent_id  = coder_agent.main.id
+  proxy_url = "https://aiproxy.example.com"
+  cert_path = "/home/coder/.certs/aibridge-proxy-ca.pem"
+}
+```
+
+### Proxy with custom port
+
+For deployments where the proxy is accessed directly on a configured port.
+See [security considerations](https://coder.com/docs/ai-coder/ai-bridge/ai-bridge-proxy/setup#security-considerations) for network access guidelines.
+
+```tf
+module "aibridge-proxy" {
+  source    = "registry.coder.com/coder/aibridge-proxy/coder"
+  version   = "1.0.0"
+  agent_id  = coder_agent.main.id
+  proxy_url = "http://internal-proxy:8888"
+}
+```

registry/coder/modules/aibridge-proxy/main.test.ts

@@ -0,0 +1,254 @@
+import { serve } from "bun";
+import {
+  afterEach,
+  beforeAll,
+  describe,
+  expect,
+  it,
+  setDefaultTimeout,
+} from "bun:test";
+import {
+  execContainer,
+  findResourceInstance,
+  removeContainer,
+  runContainer,
+  runTerraformApply,
+  runTerraformInit,
+  testRequiredVariables,
+} from "~test";
+
+let cleanupFunctions: (() => Promise<void>)[] = [];
+const registerCleanup = (cleanup: () => Promise<void>) => {
+  cleanupFunctions.push(cleanup);
+};
+afterEach(async () => {
+  const cleanupFnsCopy = cleanupFunctions.slice().reverse();
+  cleanupFunctions = [];
+  for (const cleanup of cleanupFnsCopy) {
+    try {
+      await cleanup();
+    } catch (error) {
+      console.error("Error during cleanup:", error);
+    }
+  }
+});
+
+const FAKE_CERT =
+  "-----BEGIN CERTIFICATE-----\nMIIBfakecert\n-----END CERTIFICATE-----\n";
+
+// Runs terraform apply to render the setup script, then starts a Docker
+// container where we can execute it against a mock server.
+const setupContainer = async (vars: Record<string, string> = {}) => {
+  const state = await runTerraformApply(import.meta.dir, {
+    agent_id: "foo",
+    proxy_url: "https://aiproxy.example.com",
+    ...vars,
+  });
+  const instance = findResourceInstance(state, "coder_script");
+  const id = await runContainer("lorello/alpine-bash");
+
+  registerCleanup(async () => {
+    await removeContainer(id);
+  });
+
+  return { id, instance };
+};
+
+// Starts a mock HTTP server that simulates the Coder API certificate endpoint.
+// Returns the server and its base URL.
+const setupServer = (handler: (req: Request) => Response) => {
+  const server = serve({
+    fetch: handler,
+    port: 0,
+  });
+  registerCleanup(async () => {
+    server.stop();
+  });
+  return {
+    server,
+    // Base URL without trailing slash
+    url: server.url.toString().slice(0, -1),
+  };
+};
+
+setDefaultTimeout(30 * 1000);
+
+describe("aibridge-proxy", () => {
+  beforeAll(async () => {
+    await runTerraformInit(import.meta.dir);
+  });
+
+  // Verify that agent_id and proxy_url are required.
+  testRequiredVariables(import.meta.dir, {
+    agent_id: "foo",
+    proxy_url: "https://aiproxy.example.com",
+  });
+
+  it("downloads the CA certificate successfully", async () => {
+    let receivedToken = "";
+    const { url } = setupServer((req) => {
+      const reqUrl = new URL(req.url);
+      if (reqUrl.pathname === "/api/v2/aibridge/proxy/ca-cert.pem") {
+        receivedToken = req.headers.get("Coder-Session-Token") || "";
+        return new Response(FAKE_CERT, {
+          status: 200,
+          headers: { "Content-Type": "application/x-pem-file" },
+        });
+      }
+      return new Response("not found", { status: 404 });
+    });
+
+    const { id, instance } = await setupContainer();
+
+    // Override ACCESS_URL and SESSION_TOKEN at runtime to point at the mock server.
+    const exec = await execContainer(id, [
+      "env",
+      `ACCESS_URL=${url}`,
+      "SESSION_TOKEN=test-session-token-123",
+      "bash",
+      "-c",
+      instance.script,
+    ]);
+    expect(exec.exitCode).toBe(0);
+    expect(exec.stdout).toContain(
+      "AI Bridge Proxy CA certificate saved to /tmp/aibridge-proxy/ca-cert.pem",
+    );
+
+    // Verify the cert was written to the default path.
+    const certContent = await execContainer(id, [
+      "cat",
+      "/tmp/aibridge-proxy/ca-cert.pem",
+    ]);
+    expect(certContent.stdout).toContain("BEGIN CERTIFICATE");
+
+    // Verify the session token was sent in the request header.
+    expect(receivedToken).toBe("test-session-token-123");
+  });
+
+  it("fails when the server is unreachable", async () => {
+    const { id, instance } = await setupContainer();
+
+    // Port 9999 has nothing listening, so curl will fail to connect.
+    const exec = await execContainer(id, [
+      "env",
+      "ACCESS_URL=http://localhost:9999",
+      "SESSION_TOKEN=mock-token",
+      "bash",
+      "-c",
+      instance.script,
+    ]);
+    expect(exec.exitCode).not.toBe(0);
+    expect(exec.stdout).toContain(
+      "AI Bridge Proxy setup failed: could not connect to",
+    );
+  });
+
+  it("fails when the server returns a non-200 status", async () => {
+    const { url } = setupServer(() => {
+      return new Response("not found", { status: 404 });
+    });
+
+    const { id, instance } = await setupContainer();
+
+    const exec = await execContainer(id, [
+      "env",
+      `ACCESS_URL=${url}`,
+      "SESSION_TOKEN=mock-token",
+      "bash",
+      "-c",
+      instance.script,
+    ]);
+    expect(exec.exitCode).not.toBe(0);
+    expect(exec.stdout).toContain(
+      "AI Bridge Proxy setup failed: unexpected response",
+    );
+  });
+
+  it("fails when the server returns an empty response", async () => {
+    const { url } = setupServer((req) => {
+      const reqUrl = new URL(req.url);
+      if (reqUrl.pathname === "/api/v2/aibridge/proxy/ca-cert.pem") {
+        return new Response("", { status: 200 });
+      }
+      return new Response("not found", { status: 404 });
+    });
+
+    const { id, instance } = await setupContainer();
+
+    const exec = await execContainer(id, [
+      "env",
+      `ACCESS_URL=${url}`,
+      "SESSION_TOKEN=mock-token",
+      "bash",
+      "-c",
+      instance.script,
+    ]);
+    expect(exec.exitCode).not.toBe(0);
+    expect(exec.stdout).toContain(
+      "AI Bridge Proxy setup failed: downloaded certificate is empty.",
+    );
+  });
+
+  it("saves the certificate to a custom path", async () => {
+    const { url } = setupServer((req) => {
+      const reqUrl = new URL(req.url);
+      if (reqUrl.pathname === "/api/v2/aibridge/proxy/ca-cert.pem") {
+        return new Response(FAKE_CERT, {
+          status: 200,
+          headers: { "Content-Type": "application/x-pem-file" },
+        });
+      }
+      return new Response("not found", { status: 404 });
+    });
+
+    // Pass a custom cert_path to terraform apply so the script uses it.
+    const { id, instance } = await setupContainer({
+      cert_path: "/tmp/custom/certs/proxy-ca.pem",
+    });
+
+    const exec = await execContainer(id, [
+      "env",
+      `ACCESS_URL=${url}`,
+      "SESSION_TOKEN=mock-token",
+      "bash",
+      "-c",
+      instance.script,
+    ]);
+    expect(exec.exitCode).toBe(0);
+    expect(exec.stdout).toContain(
+      "AI Bridge Proxy CA certificate saved to /tmp/custom/certs/proxy-ca.pem",
+    );
+
+    const certContent = await execContainer(id, [
+      "cat",
+      "/tmp/custom/certs/proxy-ca.pem",
+    ]);
+    expect(certContent.stdout).toContain("BEGIN CERTIFICATE");
+  });
+
+  it("does not create global proxy env vars via coder_env", async () => {
+    const state = await runTerraformApply(import.meta.dir, {
+      agent_id: "foo",
+      proxy_url: "https://aiproxy.example.com",
+    });
+
+    // Proxy env vars should NOT be set globally via coder_env.
+    // They are intended to be scoped to specific tool processes.
+    const proxyEnvVarNames = [
+      "HTTP_PROXY",
+      "HTTPS_PROXY",
+      "NODE_EXTRA_CA_CERTS",
+      "SSL_CERT_FILE",
+      "REQUESTS_CA_BUNDLE",
+      "CURL_CA_BUNDLE",
+    ];
+    const proxyEnvVars = state.resources.filter(
+      (r) =>
+        r.type === "coder_env" &&
+        r.instances.some((i) =>
+          proxyEnvVarNames.includes(i.attributes.name as string),
+        ),
+    );
+    expect(proxyEnvVars.length).toBe(0);
+  });
+});

registry/coder/modules/aibridge-proxy/main.tf

@@ -0,0 +1,81 @@
+terraform {
+  required_version = ">= 1.9"
+
+  required_providers {
+    coder = {
+      source  = "coder/coder"
+      version = ">= 2.12"
+    }
+  }
+}
+
+variable "agent_id" {
+  type        = string
+  description = "The ID of a Coder agent."
+}
+
+variable "proxy_url" {
+  type        = string
+  description = "The full URL of the AI Bridge Proxy. Include the port if not using standard ports (e.g. https://aiproxy.example.com or http://internal-proxy:8888)."
+
+  validation {
+    condition     = can(regex("^https?://", var.proxy_url))
+    error_message = "proxy_url must start with http:// or https://."
+  }
+}
+
+variable "cert_path" {
+  type        = string
+  description = "Absolute path where the AI Bridge Proxy CA certificate will be saved."
+  default     = "/tmp/aibridge-proxy/ca-cert.pem"
+
+  validation {
+    condition     = startswith(var.cert_path, "/")
+    error_message = "cert_path must be an absolute path."
+  }
+}
+
+data "coder_workspace" "me" {}
+
+data "coder_workspace_owner" "me" {}
+
+locals {
+  # Build the proxy URL with Coder authentication embedded.
+  # AI Bridge Proxy expects the Coder session token as the password
+  # in basic auth: http://coder:<token>@host:port
+  proxy_auth_url = replace(
+    var.proxy_url,
+    "://",
+    "://coder:${data.coder_workspace_owner.me.session_token}@"
+  )
+}
+
+# These outputs are intended to be consumed by tool-specific modules,
+# to set proxy environment variables scoped to their process, rather than globally.
+output "proxy_auth_url" {
+  description = "The AI Bridge Proxy URL with Coder authentication embedded (http://coder:<token>@host:port)."
+  value       = local.proxy_auth_url
+  sensitive   = true
+}
+
+output "cert_path" {
+  description = "Path to the downloaded AI Bridge Proxy CA certificate."
+  value       = var.cert_path
+}
+
+# Downloads the CA certificate from the Coder deployment.
+# This runs on workspace start but does not block login, if the script
+# fails, the workspace remains usable and the error is visible in the build logs.
+# Tools that depend on the proxy will fail until the certificate is available.
+resource "coder_script" "aibridge_proxy_setup" {
+  agent_id           = var.agent_id
+  display_name       = "AI Bridge Proxy Setup"
+  icon               = "/icon/coder.svg"
+  run_on_start       = true
+  start_blocks_login = false
+  script = templatefile("${path.module}/scripts/setup.sh", {
+    CERT_PATH     = var.cert_path,
+    ACCESS_URL    = data.coder_workspace.me.access_url,
+    SESSION_TOKEN = data.coder_workspace_owner.me.session_token,
+  })
+}

registry/coder/modules/aibridge-proxy/main.tftest.hcl

@@ -0,0 +1,210 @@
+run "test_aibridge_proxy_basic" {
+  command = plan
+
+  variables {
+    agent_id  = "test-agent-id"
+    proxy_url = "https://aiproxy.example.com"
+  }
+
+  assert {
+    condition     = var.agent_id == "test-agent-id"
+    error_message = "Agent ID should match the input variable"
+  }
+
+  assert {
+    condition     = var.proxy_url == "https://aiproxy.example.com"
+    error_message = "Proxy URL should match the input variable"
+  }
+
+  assert {
+    condition     = var.cert_path == "/tmp/aibridge-proxy/ca-cert.pem"
+    error_message = "cert_path should default to /tmp/aibridge-proxy/ca-cert.pem"
+  }
+}
+
+run "test_aibridge_proxy_empty_url_validation" {
+  command = plan
+
+  variables {
+    agent_id  = "test-agent-id"
+    proxy_url = ""
+  }
+
+  expect_failures = [
+    var.proxy_url,
+  ]
+}
+
+run "test_aibridge_proxy_invalid_url_validation" {
+  command = plan
+
+  variables {
+    agent_id  = "test-agent-id"
+    proxy_url = "aiproxy.example.com"
+  }
+
+  expect_failures = [
+    var.proxy_url,
+  ]
+}
+
+run "test_aibridge_proxy_url_formats" {
+  command = plan
+
+  variables {
+    agent_id  = "test-agent-id"
+    proxy_url = "https://aiproxy.example.com"
+  }
+
+  assert {
+    condition     = can(regex("^https?://", var.proxy_url))
+    error_message = "Proxy URL should be a valid URL with scheme"
+  }
+}
+
+run "test_aibridge_proxy_https_with_port" {
+  command = plan
+
+  variables {
+    agent_id  = "test-agent-id"
+    proxy_url = "https://aiproxy.example.com:8443"
+  }
+
+  assert {
+    condition     = can(regex("^https?://", var.proxy_url))
+    error_message = "Proxy URL should support HTTPS with custom port"
+  }
+}
+
+run "test_aibridge_proxy_http_with_port" {
+  command = plan
+
+  variables {
+    agent_id  = "test-agent-id"
+    proxy_url = "http://internal-proxy:8888"
+  }
+
+  assert {
+    condition     = can(regex("^https?://", var.proxy_url))
+    error_message = "Proxy URL should support HTTP with custom port"
+  }
+}
+
+run "test_aibridge_proxy_empty_cert_path_validation" {
+  command = plan
+
+  variables {
+    agent_id  = "test-agent-id"
+    proxy_url = "https://aiproxy.example.com"
+    cert_path = ""
+  }
+
+  expect_failures = [
+    var.cert_path,
+  ]
+}
+
+run "test_aibridge_proxy_relative_cert_path_validation" {
+  command = plan
+
+  variables {
+    agent_id  = "test-agent-id"
+    proxy_url = "https://aiproxy.example.com"
+    cert_path = "relative/path/ca-cert.pem"
+  }
+
+  expect_failures = [
+    var.cert_path,
+  ]
+}
+
+run "test_aibridge_proxy_custom_cert_path" {
+  command = plan
+
+  variables {
+    agent_id  = "test-agent-id"
+    proxy_url = "https://aiproxy.example.com"
+    cert_path = "/home/coder/.certs/ca-cert.pem"
+  }
+
+  assert {
+    condition     = var.cert_path == "/home/coder/.certs/ca-cert.pem"
+    error_message = "cert_path should match the input variable"
+  }
+}
+
+run "test_aibridge_proxy_script" {
+  command = plan
+
+  variables {
+    agent_id  = "test-agent-id"
+    proxy_url = "https://aiproxy.example.com"
+  }
+
+  assert {
+    condition     = coder_script.aibridge_proxy_setup.run_on_start == true
+    error_message = "Script should run on start"
+  }
+
+  assert {
+    condition     = coder_script.aibridge_proxy_setup.start_blocks_login == false
+    error_message = "Script should not block login"
+  }
+
+  assert {
+    condition     = coder_script.aibridge_proxy_setup.display_name == "AI Bridge Proxy Setup"
+    error_message = "Script display name should be 'AI Bridge Proxy Setup'"
+  }
+}
+
+run "test_aibridge_proxy_auth_url_https" {
+  command = plan
+
+  variables {
+    agent_id  = "test-agent-id"
+    proxy_url = "https://aiproxy.example.com"
+  }
+
+  override_data {
+    target = data.coder_workspace_owner.me
+    values = {
+      session_token = "mock-session-token"
+    }
+  }
+
+  assert {
+    condition     = output.proxy_auth_url == "https://coder:mock-session-token@aiproxy.example.com"
+    error_message = "proxy_auth_url should contain the mocked session token"
+  }
+
+  assert {
+    condition     = output.cert_path == "/tmp/aibridge-proxy/ca-cert.pem"
+    error_message = "cert_path output should match the default"
+  }
+}
+
+run "test_aibridge_proxy_auth_url_http_with_port" {
+  command = plan
+
+  variables {
+    agent_id  = "test-agent-id"
+    proxy_url = "http://internal-proxy:8888"
+  }
+
+  override_data {
+    target = data.coder_workspace_owner.me
+    values = {
+      session_token = "mock-session-token"
+    }
+  }
+
+  assert {
+    condition     = output.proxy_auth_url == "http://coder:mock-session-token@internal-proxy:8888"
+    error_message = "proxy_auth_url should preserve the port"
+  }
+
+  assert {
+    condition     = output.cert_path == "/tmp/aibridge-proxy/ca-cert.pem"
+    error_message = "cert_path output should match the default"
+  }
+}

registry/coder/modules/aibridge-proxy/scripts/setup.sh

@@ -0,0 +1,79 @@
+#!/usr/bin/env bash
+
+if [ -z "$CERT_PATH" ]; then
+  CERT_PATH="${CERT_PATH}"
+fi
+
+if [ -z "$ACCESS_URL" ]; then
+  ACCESS_URL="${ACCESS_URL}"
+fi
+
+if [ -z "$SESSION_TOKEN" ]; then
+  SESSION_TOKEN="${SESSION_TOKEN}"
+fi
+
+set -euo pipefail
+
+# Signal startup coordination.
+# The trap ensures 'complete' is always called (even on failure) so dependent
+# scripts unblock promptly and can check for the certificate themselves.
+if command -v coder > /dev/null 2>&1; then
+  coder exp sync start "aibridge-proxy-setup" > /dev/null 2>&1 || true
+  trap 'coder exp sync complete "aibridge-proxy-setup" > /dev/null 2>&1 || true' EXIT
+fi
+
+if [ -z "$ACCESS_URL" ]; then
+  echo "Error: Coder access URL is not set."
+  exit 1
+fi
+
+if [ -z "$SESSION_TOKEN" ]; then
+  echo "Error: Coder session token is not set."
+  exit 1
+fi
+
+if ! command -v curl > /dev/null; then
+  echo "Error: curl is not installed."
+  exit 1
+fi
+
+echo "--------------------------------"
+echo "AI Bridge Proxy Setup"
+printf "Certificate path: %s\n" "$CERT_PATH"
+printf "Access URL: %s\n" "$ACCESS_URL"
+echo "--------------------------------"
+
+CERT_DIR=$(dirname "$CERT_PATH")
+mkdir -p "$CERT_DIR"
+
+CERT_URL="$ACCESS_URL/api/v2/aibridge/proxy/ca-cert.pem"
+echo "Downloading AI Bridge Proxy CA certificate from $CERT_URL..."
+
+# Download the certificate with a 5s connection timeout and 10s total timeout
+# to avoid the script hanging indefinitely.
+if ! HTTP_STATUS=$(curl -s -o "$CERT_PATH" -w "%%{http_code}" \
+  --connect-timeout 5 \
+  --max-time 10 \
+  -H "Coder-Session-Token: $SESSION_TOKEN" \
+  "$CERT_URL"); then
+  echo "❌ AI Bridge Proxy setup failed: could not connect to $CERT_URL."
+  echo "Ensure AI Bridge Proxy is enabled and reachable from the workspace."
+  rm -f "$CERT_PATH"
+  exit 1
+fi
+
+if [ "$HTTP_STATUS" -ne 200 ]; then
+  echo "❌ AI Bridge Proxy setup failed: unexpected response (HTTP $HTTP_STATUS)."
+  echo "Ensure AI Bridge Proxy is enabled and reachable from the workspace."
+  rm -f "$CERT_PATH"
+  exit 1
+fi
+
+if [ ! -s "$CERT_PATH" ]; then
+  echo "❌ AI Bridge Proxy setup failed: downloaded certificate is empty."
+  rm -f "$CERT_PATH"
+  exit 1
+fi
+
+echo "AI Bridge Proxy CA certificate saved to $CERT_PATH"
+echo "✅ AI Bridge Proxy setup complete."

registry/coder/modules/claude-code/README.md

@@ -13,7 +13,7 @@ Run the [Claude Code](https://docs.anthropic.com/en/docs/agents-and-tools/claude
 ```tf
 module "claude-code" {
   source         = "registry.coder.com/coder/claude-code/coder"
-  version        = "4.7.5"
+  version        = "4.8.0"
   agent_id       = coder_agent.main.id
   workdir        = "/home/coder/project"
   claude_api_key = "xxxx-xxxxx-xxxx"
@@ -36,6 +36,19 @@ module "claude-code" {
 
 By default, Claude Code automatically resumes existing conversations when your workspace restarts. Sessions are tracked per workspace directory, so conversations continue where you left off. If no session exists (first start), your `ai_prompt` will run normally. To disable this behavior and always start fresh, set `continue = false`
 
+## State Persistence
+
+AgentAPI can save and restore its conversation state to disk across workspace restarts. This complements `continue` (which resumes the Claude CLI session) by also preserving the AgentAPI-level context. Enabled by default, requires agentapi >= v0.12.0 (older versions skip it with a warning).
+
+To disable:
+
+```tf
+module "claude-code" {
+  # ... other config
+  enable_state_persistence = false
+}
+```
+
 ## Examples
 
 ### Usage with Agent Boundaries
@@ -47,7 +60,7 @@ By default, when `enable_boundary = true`, the module uses `coder boundary` subc
 ```tf
 module "claude-code" {
   source          = "registry.coder.com/coder/claude-code/coder"
-  version         = "4.7.5"
+  version         = "4.8.0"
   agent_id        = coder_agent.main.id
   workdir         = "/home/coder/project"
   enable_boundary = true
@@ -68,7 +81,7 @@ For tasks integration with AI Bridge, add `enable_aibridge = true` to the [Usage
 ```tf
 module "claude-code" {
   source          = "registry.coder.com/coder/claude-code/coder"
-  version         = "4.7.5"
+  version         = "4.8.0"
   agent_id        = coder_agent.main.id
   workdir         = "/home/coder/project"
   enable_aibridge = true
@@ -97,7 +110,7 @@ data "coder_task" "me" {}
 
 module "claude-code" {
   source    = "registry.coder.com/coder/claude-code/coder"
-  version   = "4.7.5"
+  version   = "4.8.0"
   agent_id  = coder_agent.main.id
   workdir   = "/home/coder/project"
   ai_prompt = data.coder_task.me.prompt
@@ -120,7 +133,7 @@ This example shows additional configuration options for version pinning, custom
 ```tf
 module "claude-code" {
   source   = "registry.coder.com/coder/claude-code/coder"
-  version  = "4.7.5"
+  version  = "4.8.0"
   agent_id = coder_agent.main.id
   workdir  = "/home/coder/project"
 
@@ -176,7 +189,7 @@ Run and configure Claude Code as a standalone CLI in your workspace.
 ```tf
 module "claude-code" {
   source              = "registry.coder.com/coder/claude-code/coder"
-  version             = "4.7.5"
+  version             = "4.8.0"
   agent_id            = coder_agent.main.id
   workdir             = "/home/coder/project"
   install_claude_code = true
@@ -198,7 +211,7 @@ variable "claude_code_oauth_token" {
 
 module "claude-code" {
   source                  = "registry.coder.com/coder/claude-code/coder"
-  version                 = "4.7.5"
+  version                 = "4.8.0"
   agent_id                = coder_agent.main.id
   workdir                 = "/home/coder/project"
   claude_code_oauth_token = var.claude_code_oauth_token
@@ -271,7 +284,7 @@ resource "coder_env" "bedrock_api_key" {
 
 module "claude-code" {
   source   = "registry.coder.com/coder/claude-code/coder"
-  version  = "4.7.5"
+  version  = "4.8.0"
   agent_id = coder_agent.main.id
   workdir  = "/home/coder/project"
   model    = "global.anthropic.claude-sonnet-4-5-20250929-v1:0"
@@ -328,7 +341,7 @@ resource "coder_env" "google_application_credentials" {
 
 module "claude-code" {
   source   = "registry.coder.com/coder/claude-code/coder"
-  version  = "4.7.5"
+  version  = "4.8.0"
   agent_id = coder_agent.main.id
   workdir  = "/home/coder/project"
   model    = "claude-sonnet-4@20250514"

registry/coder/modules/claude-code/main.tf

@@ -67,7 +67,7 @@ variable "cli_app_display_name" {
 
 variable "pre_install_script" {
   type        = string
-  description = "Custom script to run before installing Claude Code."
+  description = "Custom script to run before installing Claude Code. Can be used for dependency ordering between modules (e.g., waiting for git-clone to complete before Claude Code initialization)."
   default     = null
 }
 
@@ -261,6 +261,12 @@ variable "enable_aibridge" {
   }
 }
 
+variable "enable_state_persistence" {
+  type        = bool
+  description = "Enable AgentAPI conversation state persistence across restarts."
+  default     = true
+}
+
 resource "coder_env" "claude_code_md_path" {
   count    = var.claude_md_path == "" ? 0 : 1
   agent_id = var.agent_id
@@ -356,25 +362,26 @@ locals {
 
 module "agentapi" {
   source  = "registry.coder.com/coder/agentapi/coder"
-  version = "2.0.0"
+  version = "2.2.0"
 
-  agent_id             = var.agent_id
-  web_app_slug         = local.app_slug
-  web_app_order        = var.order
-  web_app_group        = var.group
-  web_app_icon         = var.icon
-  web_app_display_name = var.web_app_display_name
-  folder               = local.workdir
-  cli_app              = var.cli_app
-  cli_app_slug         = var.cli_app ? "${local.app_slug}-cli" : null
-  cli_app_display_name = var.cli_app ? var.cli_app_display_name : null
-  agentapi_subdomain   = var.subdomain
-  module_dir_name      = local.module_dir_name
-  install_agentapi     = var.install_agentapi
-  agentapi_version     = var.agentapi_version
-  pre_install_script   = var.pre_install_script
-  post_install_script  = var.post_install_script
-  start_script         = <<-EOT
+  agent_id                 = var.agent_id
+  web_app_slug             = local.app_slug
+  web_app_order            = var.order
+  web_app_group            = var.group
+  web_app_icon             = var.icon
+  web_app_display_name     = var.web_app_display_name
+  folder                   = local.workdir
+  cli_app                  = var.cli_app
+  cli_app_slug             = var.cli_app ? "${local.app_slug}-cli" : null
+  cli_app_display_name     = var.cli_app ? var.cli_app_display_name : null
+  agentapi_subdomain       = var.subdomain
+  module_dir_name          = local.module_dir_name
+  install_agentapi         = var.install_agentapi
+  agentapi_version         = var.agentapi_version
+  enable_state_persistence = var.enable_state_persistence
+  pre_install_script       = var.pre_install_script
+  post_install_script      = var.post_install_script
+  start_script             = <<-EOT
     #!/bin/bash
     set -o errexit
     set -o pipefail

registry/coder/modules/claude-code/main.tftest.hcl

@@ -387,6 +387,36 @@ run "test_aibridge_disabled_with_api_key" {
   }
 }
 
+run "test_enable_state_persistence_default" {
+  command = plan
+
+  variables {
+    agent_id = "test-agent"
+    workdir  = "/home/coder"
+  }
+
+  assert {
+    condition     = var.enable_state_persistence == true
+    error_message = "enable_state_persistence should default to true"
+  }
+}
+
+run "test_disable_state_persistence" {
+  command = plan
+
+  variables {
+    agent_id                 = "test-agent"
+    workdir                  = "/home/coder"
+    enable_state_persistence = false
+  }
+
+  assert {
+    condition     = var.enable_state_persistence == false
+    error_message = "enable_state_persistence should be false when explicitly disabled"
+  }
+}
+
+
 run "test_no_api_key_no_env" {
   command = plan
 

registry/coder/modules/devcontainers-cli/README.md

@@ -14,8 +14,9 @@ The devcontainers-cli module provides an easy way to install [`@devcontainers/cl
 
 ```tf
 module "devcontainers-cli" {
-  source   = "registry.coder.com/coder/devcontainers-cli/coder"
-  version  = "1.0.34"
-  agent_id = coder_agent.example.id
+  source             = "registry.coder.com/coder/devcontainers-cli/coder"
+  version            = "1.1.0"
+  agent_id           = coder_agent.example.id
+  start_blocks_login = false
 }
 ```

registry/coder/modules/devcontainers-cli/main.tf

@@ -14,10 +14,17 @@ variable "agent_id" {
   description = "The ID of a Coder agent."
 }
 
-resource "coder_script" "devcontainers-cli" {
-  agent_id     = var.agent_id
-  display_name = "devcontainers-cli"
-  icon         = "/icon/devcontainers.svg"
-  script       = templatefile("${path.module}/run.sh", {})
-  run_on_start = true
+variable "start_blocks_login" {
+  type        = bool
+  default     = false
+  description = "Boolean, This option determines whether users can log in immediately or must wait for the workspace to finish running this script upon startup."
+}
+
+resource "coder_script" "devcontainers-cli" {
+  agent_id           = var.agent_id
+  display_name       = "devcontainers-cli"
+  icon               = "/icon/devcontainers.svg"
+  script             = templatefile("${path.module}/run.sh", {})
+  run_on_start       = true
+  start_blocks_login = var.start_blocks_login
 }

registry/coder/modules/vscode-web/README.md

@@ -14,7 +14,7 @@ Automatically install [Visual Studio Code Server](https://code.visualstudio.com/
 module "vscode-web" {
   count          = data.coder_workspace.me.start_count
   source         = "registry.coder.com/coder/vscode-web/coder"
-  version        = "1.4.3"
+  version        = "1.5.0"
   agent_id       = coder_agent.example.id
   accept_license = true
 }
@@ -30,7 +30,7 @@ module "vscode-web" {
 module "vscode-web" {
   count          = data.coder_workspace.me.start_count
   source         = "registry.coder.com/coder/vscode-web/coder"
-  version        = "1.4.3"
+  version        = "1.5.0"
   agent_id       = coder_agent.example.id
   install_prefix = "/home/coder/.vscode-web"
   folder         = "/home/coder"
@@ -44,22 +44,22 @@ module "vscode-web" {
 module "vscode-web" {
   count          = data.coder_workspace.me.start_count
   source         = "registry.coder.com/coder/vscode-web/coder"
-  version        = "1.4.3"
+  version        = "1.5.0"
   agent_id       = coder_agent.example.id
   extensions     = ["github.copilot", "ms-python.python", "ms-toolsai.jupyter"]
   accept_license = true
 }
 ```
 
-### Pre-configure Settings
+### Pre-configure Machine Settings
 
-Configure VS Code's [settings.json](https://code.visualstudio.com/docs/getstarted/settings#_settings-json-file) file:
+Configure VS Code's [Machine settings.json](https://code.visualstudio.com/docs/getstarted/settings#_settings-json-file). These settings are merged with any existing machine settings on startup:
 
 ```tf
 module "vscode-web" {
   count      = data.coder_workspace.me.start_count
   source     = "registry.coder.com/coder/vscode-web/coder"
-  version    = "1.4.3"
+  version    = "1.5.0"
   agent_id   = coder_agent.example.id
   extensions = ["dracula-theme.theme-dracula"]
   settings = {
@@ -69,6 +69,9 @@ module "vscode-web" {
 }
 ```
 
+> [!WARNING]
+> Merging settings requires `jq` or `python3`. If neither is available, existing machine settings will be preserved. User settings configured through the VS Code UI are stored in browser local storage and will not persist across different browsers or devices.
+
 ### Pin a specific VS Code Web version
 
 By default, this module installs the latest. To pin a specific version, retrieve the commit ID from the [VS Code Update API](https://update.code.visualstudio.com/api/commits/stable/server-linux-x64-web) and verify its corresponding release on the [VS Code GitHub Releases](https://github.com/microsoft/vscode/releases).
@@ -77,7 +80,7 @@ By default, this module installs the latest. To pin a specific version, retrieve
 module "vscode-web" {
   count          = data.coder_workspace.me.start_count
   source         = "registry.coder.com/coder/vscode-web/coder"
-  version        = "1.4.3"
+  version        = "1.5.0"
   agent_id       = coder_agent.example.id
   commit_id      = "e54c774e0add60467559eb0d1e229c6452cf8447"
   accept_license = true
@@ -93,7 +96,7 @@ Note: Either `workspace` or `folder` can be used, but not both simultaneously. T
 module "vscode-web" {
   count     = data.coder_workspace.me.start_count
   source    = "registry.coder.com/coder/vscode-web/coder"
-  version   = "1.4.3"
+  version   = "1.5.0"
   agent_id  = coder_agent.example.id
   workspace = "/home/coder/coder.code-workspace"
 }

registry/coder/modules/vscode-web/main.test.ts

@@ -1,42 +1,298 @@
-import { describe, expect, it } from "bun:test";
-import { runTerraformApply, runTerraformInit } from "~test";
+import {
+  describe,
+  expect,
+  it,
+  beforeAll,
+  afterEach,
+  setDefaultTimeout,
+} from "bun:test";
+import {
+  runTerraformApply,
+  runTerraformInit,
+  runContainer,
+  execContainer,
+  removeContainer,
+  findResourceInstance,
+} from "~test";
+
+// Set timeout to 2 minutes for tests that install packages
+setDefaultTimeout(2 * 60 * 1000);
+
+let cleanupContainers: string[] = [];
+
+afterEach(async () => {
+  for (const id of cleanupContainers) {
+    try {
+      await removeContainer(id);
+    } catch {
+      // Ignore cleanup errors
+    }
+  }
+  cleanupContainers = [];
+});
 
 describe("vscode-web", async () => {
-  await runTerraformInit(import.meta.dir);
-
-  it("accept_license should be set to true", () => {
-    const t = async () => {
-      await runTerraformApply(import.meta.dir, {
-        agent_id: "foo",
-        accept_license: "false",
-      });
-    };
-    expect(t).toThrow("Invalid value for variable");
+  beforeAll(async () => {
+    await runTerraformInit(import.meta.dir);
   });
 
-  it("use_cached and offline can not be used together", () => {
-    const t = async () => {
+  it("accept_license should be set to true", async () => {
+    try {
       await runTerraformApply(import.meta.dir, {
         agent_id: "foo",
-        accept_license: "true",
-        use_cached: "true",
-        offline: "true",
+        accept_license: false,
       });
-    };
-    expect(t).toThrow("Offline and Use Cached can not be used together");
+      throw new Error("Expected terraform apply to fail");
+    } catch (ex) {
+      expect((ex as Error).message).toContain("Invalid value for variable");
+    }
   });
 
-  it("offline and extensions can not be used together", () => {
-    const t = async () => {
+  it("use_cached and offline can not be used together", async () => {
+    try {
       await runTerraformApply(import.meta.dir, {
         agent_id: "foo",
-        accept_license: "true",
-        offline: "true",
-        extensions: '["1", "2"]',
+        accept_license: true,
+        use_cached: true,
+        offline: true,
       });
-    };
-    expect(t).toThrow("Offline mode does not allow extensions to be installed");
+      throw new Error("Expected terraform apply to fail");
+    } catch (ex) {
+      expect((ex as Error).message).toContain(
+        "Offline and Use Cached can not be used together",
+      );
+    }
   });
 
-  // More tests depend on shebang refactors
+  it("offline and extensions can not be used together", async () => {
+    try {
+      await runTerraformApply(import.meta.dir, {
+        agent_id: "foo",
+        accept_license: true,
+        offline: true,
+        extensions: '["ms-python.python"]',
+      });
+      throw new Error("Expected terraform apply to fail");
+    } catch (ex) {
+      expect((ex as Error).message).toContain(
+        "Offline mode does not allow extensions to be installed",
+      );
+    }
+  });
+
+  it("creates settings file with correct content", async () => {
+    const state = await runTerraformApply(import.meta.dir, {
+      agent_id: "foo",
+      accept_license: true,
+      use_cached: true,
+      settings: '{"editor.fontSize": 14}',
+    });
+
+    const containerId = await runContainer("ubuntu:22.04");
+    cleanupContainers.push(containerId);
+
+    // Create a mock code-server CLI that the script expects
+    await execContainer(containerId, [
+      "bash",
+      "-c",
+      `mkdir -p /tmp/vscode-web/bin && cat > /tmp/vscode-web/bin/code-server << 'MOCKEOF'
+#!/bin/bash
+echo "Mock code-server running"
+exit 0
+MOCKEOF
+chmod +x /tmp/vscode-web/bin/code-server`,
+    ]);
+
+    const script = findResourceInstance(state, "coder_script");
+
+    const scriptResult = await execContainer(containerId, [
+      "bash",
+      "-c",
+      script.script,
+    ]);
+    expect(scriptResult.exitCode).toBe(0);
+
+    // Check that settings file was created
+    const settingsResult = await execContainer(containerId, [
+      "cat",
+      "/root/.vscode-server/data/Machine/settings.json",
+    ]);
+
+    expect(settingsResult.exitCode).toBe(0);
+    expect(settingsResult.stdout).toContain("editor.fontSize");
+    expect(settingsResult.stdout).toContain("14");
+  });
+
+  it("merges settings with existing settings file", async () => {
+    const state = await runTerraformApply(import.meta.dir, {
+      agent_id: "foo",
+      accept_license: true,
+      use_cached: true,
+      settings: '{"new.setting": "new_value"}',
+    });
+
+    const containerId = await runContainer("ubuntu:22.04");
+    cleanupContainers.push(containerId);
+
+    // Install jq and create mock code-server CLI
+    await execContainer(containerId, ["apt-get", "update", "-qq"]);
+    await execContainer(containerId, ["apt-get", "install", "-y", "-qq", "jq"]);
+    await execContainer(containerId, [
+      "bash",
+      "-c",
+      `mkdir -p /tmp/vscode-web/bin && cat > /tmp/vscode-web/bin/code-server << 'MOCKEOF'
+#!/bin/bash
+echo "Mock code-server running"
+exit 0
+MOCKEOF
+chmod +x /tmp/vscode-web/bin/code-server`,
+    ]);
+
+    // Pre-create an existing settings file
+    await execContainer(containerId, [
+      "bash",
+      "-c",
+      `mkdir -p /root/.vscode-server/data/Machine && echo '{"existing.setting": "existing_value"}' > /root/.vscode-server/data/Machine/settings.json`,
+    ]);
+
+    const script = findResourceInstance(state, "coder_script");
+
+    const scriptResult = await execContainer(containerId, [
+      "bash",
+      "-c",
+      script.script,
+    ]);
+    expect(scriptResult.exitCode).toBe(0);
+
+    // Check that settings were merged (both existing and new should be present)
+    const settingsResult = await execContainer(containerId, [
+      "cat",
+      "/root/.vscode-server/data/Machine/settings.json",
+    ]);
+
+    expect(settingsResult.exitCode).toBe(0);
+    // Should contain both existing and new settings
+    expect(settingsResult.stdout).toContain("existing.setting");
+    expect(settingsResult.stdout).toContain("existing_value");
+    expect(settingsResult.stdout).toContain("new.setting");
+    expect(settingsResult.stdout).toContain("new_value");
+  });
+
+  it("merges settings using python3 fallback when jq unavailable", async () => {
+    const state = await runTerraformApply(import.meta.dir, {
+      agent_id: "foo",
+      accept_license: true,
+      use_cached: true,
+      settings: '{"new.setting": "new_value"}',
+    });
+
+    const containerId = await runContainer("ubuntu:22.04");
+    cleanupContainers.push(containerId);
+
+    // Install python3 (ubuntu:22.04 doesn't have it by default)
+    await execContainer(containerId, ["apt-get", "update", "-qq"]);
+    await execContainer(containerId, [
+      "apt-get",
+      "install",
+      "-y",
+      "-qq",
+      "python3",
+    ]);
+
+    // Create mock code-server CLI (no jq installed)
+    await execContainer(containerId, [
+      "bash",
+      "-c",
+      `mkdir -p /tmp/vscode-web/bin && cat > /tmp/vscode-web/bin/code-server << 'MOCKEOF'
+#!/bin/bash
+echo "Mock code-server running"
+exit 0
+MOCKEOF
+chmod +x /tmp/vscode-web/bin/code-server`,
+    ]);
+
+    // Pre-create an existing settings file
+    await execContainer(containerId, [
+      "bash",
+      "-c",
+      `mkdir -p /root/.vscode-server/data/Machine && echo '{"existing.setting": "existing_value"}' > /root/.vscode-server/data/Machine/settings.json`,
+    ]);
+
+    const script = findResourceInstance(state, "coder_script");
+
+    const scriptResult = await execContainer(containerId, [
+      "bash",
+      "-c",
+      script.script,
+    ]);
+    expect(scriptResult.exitCode).toBe(0);
+
+    // Check that settings were merged using python3 fallback
+    const settingsResult = await execContainer(containerId, [
+      "cat",
+      "/root/.vscode-server/data/Machine/settings.json",
+    ]);
+
+    expect(settingsResult.exitCode).toBe(0);
+    // Should contain both existing and new settings
+    expect(settingsResult.stdout).toContain("existing.setting");
+    expect(settingsResult.stdout).toContain("existing_value");
+    expect(settingsResult.stdout).toContain("new.setting");
+    expect(settingsResult.stdout).toContain("new_value");
+  });
+
+  it("preserves existing settings when neither jq nor python3 available", async () => {
+    const state = await runTerraformApply(import.meta.dir, {
+      agent_id: "foo",
+      accept_license: true,
+      use_cached: true,
+      settings: '{"new.setting": "new_value"}',
+    });
+
+    // Use ubuntu without installing jq or python3 (neither available by default)
+    const containerId = await runContainer("ubuntu:22.04");
+    cleanupContainers.push(containerId);
+
+    // Create mock code-server CLI
+    await execContainer(containerId, [
+      "bash",
+      "-c",
+      `mkdir -p /tmp/vscode-web/bin && cat > /tmp/vscode-web/bin/code-server << 'MOCKEOF'
+#!/bin/bash
+echo "Mock code-server running"
+exit 0
+MOCKEOF
+chmod +x /tmp/vscode-web/bin/code-server`,
+    ]);
+
+    // Pre-create an existing settings file
+    await execContainer(containerId, [
+      "bash",
+      "-c",
+      `mkdir -p /root/.vscode-server/data/Machine && echo '{"existing.setting": "existing_value"}' > /root/.vscode-server/data/Machine/settings.json`,
+    ]);
+
+    const script = findResourceInstance(state, "coder_script");
+
+    // Run script - should warn but not fail
+    const scriptResult = await execContainer(containerId, [
+      "bash",
+      "-c",
+      script.script,
+    ]);
+    expect(scriptResult.exitCode).toBe(0);
+    expect(scriptResult.stdout).toContain("Could not merge settings");
+
+    // Existing settings should be preserved (not overwritten)
+    const settingsResult = await execContainer(containerId, [
+      "cat",
+      "/root/.vscode-server/data/Machine/settings.json",
+    ]);
+
+    expect(settingsResult.exitCode).toBe(0);
+    expect(settingsResult.stdout).toContain("existing.setting");
+    expect(settingsResult.stdout).toContain("existing_value");
+    expect(settingsResult.stdout).not.toContain("new.setting");
+    expect(settingsResult.stdout).not.toContain("new_value");
+  });
 });

registry/coder/modules/vscode-web/main.tf

@@ -105,7 +105,7 @@ variable "group" {
 
 variable "settings" {
   type        = any
-  description = "A map of settings to apply to VS Code web."
+  description = "A map of settings to apply to VS Code Web's Machine settings. These settings are merged with any existing machine settings on startup."
   default     = {}
 }
 
@@ -167,6 +167,10 @@ variable "workspace" {
 data "coder_workspace_owner" "me" {}
 data "coder_workspace" "me" {}
 
+locals {
+  settings_b64 = var.settings != {} ? base64encode(jsonencode(var.settings)) : ""
+}
+
 resource "coder_script" "vscode-web" {
   agent_id     = var.agent_id
   display_name = "VS Code Web"
@@ -177,8 +181,7 @@ resource "coder_script" "vscode-web" {
     INSTALL_PREFIX : var.install_prefix,
     EXTENSIONS : join(",", var.extensions),
     TELEMETRY_LEVEL : var.telemetry_level,
-    // This is necessary otherwise the quotes are stripped!
-    SETTINGS : replace(jsonencode(var.settings), "\"", "\\\""),
+    SETTINGS_B64 : local.settings_b64,
     OFFLINE : var.offline,
     USE_CACHED : var.use_cached,
     DISABLE_TRUST : var.disable_trust,

registry/coder/modules/vscode-web/run.sh

@@ -4,13 +4,54 @@ BOLD='\033[0;1m'
 EXTENSIONS=("${EXTENSIONS}")
 VSCODE_WEB="${INSTALL_PREFIX}/bin/code-server"
 
+# Merge settings from module with existing settings file
+# Uses jq if available, falls back to Python3 for deep merge
+merge_settings() {
+  local new_settings="$1"
+  local settings_file="$2"
+
+  if [ -z "$new_settings" ] || [ "$new_settings" = "{}" ]; then
+    return 0
+  fi
+
+  if [ ! -f "$settings_file" ]; then
+    mkdir -p "$(dirname "$settings_file")"
+    printf '%s\n' "$new_settings" > "$settings_file"
+    printf "⚙️ Creating settings file...\n"
+    return 0
+  fi
+
+  local tmpfile
+  tmpfile="$(mktemp)"
+
+  if command -v jq > /dev/null 2>&1; then
+    if jq -s '.[0] * .[1]' "$settings_file" <(printf '%s\n' "$new_settings") > "$tmpfile" 2> /dev/null; then
+      mv "$tmpfile" "$settings_file"
+      printf "⚙️ Merging settings...\n"
+      return 0
+    fi
+  fi
+
+  if command -v python3 > /dev/null 2>&1; then
+    if python3 -c "import json,sys;m=lambda a,b:{**a,**{k:m(a[k],v)if k in a and type(a[k])==type(v)==dict else v for k,v in b.items()}};print(json.dumps(m(json.load(open(sys.argv[1])),json.loads(sys.argv[2])),indent=2))" "$settings_file" "$new_settings" > "$tmpfile" 2> /dev/null; then
+      mv "$tmpfile" "$settings_file"
+      printf "⚙️ Merging settings...\n"
+      return 0
+    fi
+  fi
+
+  rm -f "$tmpfile"
+  printf "Warning: Could not merge settings (jq or python3 required). Keeping existing settings.\n"
+  return 0
+}
+
 # Set extension directory
 EXTENSION_ARG=""
 if [ -n "${EXTENSIONS_DIR}" ]; then
   EXTENSION_ARG="--extensions-dir=${EXTENSIONS_DIR}"
 fi
 
-# Set extension directory
+# Set server base path
 SERVER_BASE_PATH_ARG=""
 if [ -n "${SERVER_BASE_PATH}" ]; then
   SERVER_BASE_PATH_ARG="--server-base-path=${SERVER_BASE_PATH}"
@@ -28,11 +69,14 @@ run_vscode_web() {
   "$VSCODE_WEB" serve-local "$EXTENSION_ARG" "$SERVER_BASE_PATH_ARG" "$DISABLE_TRUST_ARG" --port "${PORT}" --host 127.0.0.1 --accept-server-license-terms --without-connection-token --telemetry-level "${TELEMETRY_LEVEL}" > "${LOG_PATH}" 2>&1 &
 }
 
-# Check if the settings file exists...
-if [ ! -f ~/.vscode-server/data/Machine/settings.json ]; then
-  echo "⚙️ Creating settings file..."
-  mkdir -p ~/.vscode-server/data/Machine
-  echo "${SETTINGS}" > ~/.vscode-server/data/Machine/settings.json
+# Apply machine settings (merge with existing if present)
+SETTINGS_B64='${SETTINGS_B64}'
+if [ -n "$SETTINGS_B64" ]; then
+  if SETTINGS_JSON="$(echo -n "$SETTINGS_B64" | base64 -d 2> /dev/null)" && [ -n "$SETTINGS_JSON" ]; then
+    merge_settings "$SETTINGS_JSON" ~/.vscode-server/data/Machine/settings.json
+  else
+    printf "Warning: Failed to decode settings. Skipping settings configuration.\n"
+  fi
 fi
 
 # Check if vscode-server is already installed for offline or cached mode