diff --git a/AGENTS.md b/AGENTS.md
index 9bc9753f5..46b9ff051 100644
--- a/AGENTS.md
+++ b/AGENTS.md
@@ -527,7 +527,9 @@ When adding code that needs a new string, decide up front which rule it falls un
   - `/api/automation/*` → automation backend (:18001)
   - `/api/*`, `/sockets`, etc. → agent server (:18000)
   - `/*` (default) → frontend server (:3001), either Vite or static depending on launcher mode
-  - Environment variables: `PORT` (ingress port, default: 8000), `OH_AUTOMATION_GIT_REF` (git ref, overrides default version), `OH_AUTOMATION_VERSION` (default: `1.0.0a3`), `AUTOMATION_LOCAL_API_KEY` (optional, use a fixed key; default: persisted generated key), `OH_AUTOMATION_API_KEY_PATH` (override the persisted default key path)
+  - Environment variables: `PORT` (ingress port, default: 8000), `OH_AUTOMATION_GIT_REF` (git ref, overrides default version), `OH_AUTOMATION_VERSION` (default: `1.0.0a3`), `AUTOMATION_DB_URL` (optional override for the automation SQLite DB), `AUTOMATION_LOCAL_API_KEY` (optional, use a fixed key; default: persisted generated key), `OH_AUTOMATION_API_KEY_PATH` (override the persisted default key path)
+  - For local cross-repo test harnesses, prefer overriding `AUTOMATION_DB_URL` rather than `OH_CANVAS_SAFE_STATE_DIR` when you need a clean automation scheduler state but want to keep the user's existing LLM profiles/secrets. A fresh state dir also changes `OH_PERSISTENCE_DIR`, which can make the stack look like LLM setup was lost.
+  - The launcher should wait for both the automation backend (`/api/automation/health`) and the frontend (`/`) to become reachable before starting ingress and printing the ready banner; otherwise first-load requests hit proxy errors (`/api/automation/health`, `/`, `/favicon.ico`) and the Automations page can incorrectly show Backend Not Configured on a healthy-but-still-booting stack.
   - `scripts/check-sdk-version-sync.mjs` checks the released `openhands-automation` package against `versions.automationSdk` in `config/defaults.json`; that value may intentionally lag `versions.agentServer` while automation has not yet published a matching release.
   - Access points: `http://localhost:8000/` (main UI), `http://localhost:8000/api/automation/docs` (API docs)
   - Security: `AUTOMATION_LOCAL_API_KEY` defaults to a generated key persisted across restarts because static frontend builds bake it into `VITE_AUTOMATION_API_KEY`. Set the env var explicitly to rotate or pin it. The cipher key (`OH_SECRET_KEY`) is persisted at `~/.openhands/agent-canvas/secret-key.txt` (same file used by `docker/entrypoint.sh`); both modes share the same key automatically when using the same `~/.openhands` directory.
diff --git a/package-lock.json b/package-lock.json
index 31e38ba26..f69c5651c 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -12,7 +12,7 @@
         "@heroui/react": "2.8.10",
         "@microlink/react-json-view": "1.31.20",
         "@monaco-editor/react": "4.7.0",
-        "@openhands/extensions": "0.3.0",
+        "@openhands/extensions": "git+https://github.com/jamiechicago312/extensions.git#1566b45055779dd2ef33070e76c0976c4175ebfc",
         "@openhands/typescript-client": "1.24.3",
         "@react-router/node": "7.17.0",
         "@react-router/serve": "7.17.0",
@@ -3469,8 +3469,8 @@
     },
     "node_modules/@openhands/extensions": {
       "version": "0.3.0",
-      "resolved": "https://registry.npmjs.org/@openhands/extensions/-/extensions-0.3.0.tgz",
-      "integrity": "sha512-6xewbbmrDG6GbnI/Gga+o3+cw1jUpPkEW4wJKtL1mncL9f1qpI93YOBQMlrdQnu0JMRnLAMYSeURksqToUw2rw==",
+      "resolved": "git+https://github.com/jamiechicago312/extensions.git#1566b45055779dd2ef33070e76c0976c4175ebfc",
+      "integrity": "sha512-kNqzQc+DonfhI3ZqVWC6pw5FeYps9SY2ad7qUKRpT9826G2s/PxOQrIe/zG0ogoMzIVl7QIU3sUe/Y1rLyUmMA==",
       "license": "MIT",
       "engines": {
         "node": ">=18.20.0"
diff --git a/package.json b/package.json
index 197203563..e74a85d3a 100644
--- a/package.json
+++ b/package.json
@@ -23,7 +23,7 @@
     "@heroui/react": "2.8.10",
     "@microlink/react-json-view": "1.31.20",
     "@monaco-editor/react": "4.7.0",
-    "@openhands/extensions": "0.3.0",
+    "@openhands/extensions": "git+https://github.com/jamiechicago312/extensions.git#1566b45055779dd2ef33070e76c0976c4175ebfc",
     "@openhands/typescript-client": "1.24.3",
     "@react-router/node": "7.17.0",
     "@react-router/serve": "7.17.0",
@@ -70,7 +70,9 @@
     "zustand": "5.0.12"
   },
   "scripts": {
-    "dev": "node --env-file-if-exists=.env scripts/dev-with-automation.mjs",
+    "dev": "node --env-file-if-exists=.env scripts/dev-github-windows-stack.mjs",
+    "dev:default": "node --env-file-if-exists=.env scripts/dev-with-automation.mjs",
+    "dev:test-github-windows-stack": "node --env-file-if-exists=.env scripts/dev-github-windows-stack.mjs",
     "dev:static": "node --env-file-if-exists=.env scripts/dev-static.mjs",
     "dev:extra-backend": "node --env-file-if-exists=.env scripts/dev-extra-backend.mjs",
     "dev:minimal": "node --env-file-if-exists=.env scripts/dev-safe.mjs",
diff --git a/scripts/dev-github-windows-stack.mjs b/scripts/dev-github-windows-stack.mjs
new file mode 100644
index 000000000..0913a2b30
--- /dev/null
+++ b/scripts/dev-github-windows-stack.mjs
@@ -0,0 +1,26 @@
+import { homedir } from "node:os";
+import { dirname, join } from "node:path";
+
+import { main } from "./dev-with-automation.mjs";
+
+const DEFAULT_STATE_DIR = join(homedir(), ".openhands", "agent-canvas");
+const stateDir =
+  process.env.OH_CANVAS_SAFE_STATE_DIR ||
+  process.env.STATE_DIR ||
+  DEFAULT_STATE_DIR;
+const automationDbPath = join(
+  dirname(stateDir),
+  "automation",
+  "github-windows-stack.db",
+);
+
+process.env.OH_AUTOMATION_REPO ??=
+  "https://github.com/jamiechicago312/automation.git";
+process.env.OH_AUTOMATION_GIT_REF ??=
+  "d20a68c1ef581370d1297da42a9b43a1de3c87b4";
+process.env.AUTOMATION_DB_URL ??=
+  `sqlite+aiosqlite:///${automationDbPath}`;
+
+await main({
+  bannerTitle: "Agent Canvas + Automation Development Stack (GitHub Windows test)",
+});
diff --git a/scripts/dev-with-automation.mjs b/scripts/dev-with-automation.mjs
index 9779e8ec8..809627df7 100644
--- a/scripts/dev-with-automation.mjs
+++ b/scripts/dev-with-automation.mjs
@@ -29,6 +29,7 @@
  * Environment variables:
  *   - PORT: Ingress port (default: 8000)
  *   - OH_AUTOMATION_GIT_REF: Git ref for automation (default: main)
+ *   - AUTOMATION_DB_URL: Optional sqlite URL override for the automation DB
  *   - OH_AGENT_SERVER_LOCAL_PATH: Absolute path to a local software-agent-sdk
  *     checkout. Highest precedence for agent-server source selection: rebuilds
  *     the agent-server from local source and installs openhands-sdk,
@@ -250,6 +251,7 @@ ENVIRONMENT VARIABLES:
   PORT                        Alternative to --port
   OH_AUTOMATION_GIT_REF       Git ref for automation (overrides default version)
   OH_AUTOMATION_VERSION       Specific PyPI version for automation (default: ${DEFAULT_AUTOMATION_VERSION})
+  AUTOMATION_DB_URL           Override the automation SQLite DB path/URL
   OH_AGENT_SERVER_LOCAL_PATH  Absolute path to a local software-agent-sdk checkout (highest precedence)
   OH_AGENT_SERVER_GIT_REF     Git ref for agent-server SDK (overrides default version)
   OH_AGENT_SERVER_VERSION     Specific PyPI version for agent-server
@@ -819,8 +821,13 @@ function startAutomationBackend(config) {
             }
           : {}),
         AUTOMATION_AGENT_SERVER_API_KEY: config.sessionApiKey,
-        // ~/.openhands/automation/automations.db — matches docker/entrypoint.sh.
-        AUTOMATION_DB_URL: `sqlite+aiosqlite:///${join(dirname(config.stateDir), SHARED_DEFAULTS.paths.automationDb)}`,
+        // ~/.openhands/automation/automations.db by default — matches docker/entrypoint.sh.
+        // Allow callers to override it so local test harnesses can avoid stale
+        // scheduled automations while still reusing the user's existing LLM
+        // profiles and secrets.
+        AUTOMATION_DB_URL:
+          process.env.AUTOMATION_DB_URL ||
+          `sqlite+aiosqlite:///${join(dirname(config.stateDir), SHARED_DEFAULTS.paths.automationDb)}`,
         // The automation backend uses this as its publicly-reachable base
         // URL: it's appended to callback URLs and injected into each
         // sandbox as `AUTOMATION_API_URL` (consumed by setup.sh for
@@ -1319,8 +1326,35 @@ async function main(options = {}) {
     }
   }
 
-  // 5. Wait for services to be ready
-  await delay(2000);
+  // 5. Wait for launched services to become reachable before exposing ingress.
+  // Without this the browser can hit / or /api/automation/health while Vite or
+  // the automation backend is still booting, which surfaces misleading proxy
+  // errors and an empty automations screen on first load.
+  const readinessChecks = [];
+  if (config.launchAutomation) {
+    readinessChecks.push(
+      waitForService(
+        "automation",
+        `http://localhost:${config.autoBackendPort}${AUTOMATION_ROUTE_PREFIX}/health`,
+        60000,
+      ),
+    );
+  }
+  if (config.launchFrontend) {
+    const frontendUrl = getFrontendBackend(config);
+    if (frontendUrl) {
+      readinessChecks.push(
+        waitForService(
+          useStaticMode ? "static" : "vite",
+          frontendUrl,
+          60000,
+        ),
+      );
+    }
+  }
+  if (readinessChecks.length > 0) {
+    await Promise.all(readinessChecks);
+  }
 
   // 6. Start ingress proxy (routes traffic only to running services)
   startIngress(config);