diff --git a/package.json b/package.json
index ad7c7045..150cae1f 100644
--- a/package.json
+++ b/package.json
@@ -13,7 +13,9 @@
     "postinstall": "npx @playwright/mcp install-browser chrome-for-testing || exit 0",
     "prebuild": "node scripts/bootstrap-pilotdeck-config.mjs && cd src/context/memory/edgeclaw-memory-core && npm run build",
     "build": "node -e \"require('fs').rmSync('dist',{recursive:true,force:true})\" && tsc -p tsconfig.json && node -e \"require('fs').cpSync('src/extension/plugins/builtin','dist/src/extension/plugins/builtin',{recursive:true})\"",
+    "preserver": "node scripts/bootstrap-pilotdeck-config.mjs",
     "server": "tsx src/cli/pilotdeck.ts server",
+    "preserver:built": "node scripts/bootstrap-pilotdeck-config.mjs",
     "server:built": "node dist/src/cli/pilotdeck.js server",
     "skills:migrate": "tsx src/cli/pilotdeck.ts skills migrate",
     "predev": "node scripts/bootstrap-pilotdeck-config.mjs",
diff --git a/scripts/dev-launcher.mjs b/scripts/dev-launcher.mjs
index 58b260a3..1e121877 100644
--- a/scripts/dev-launcher.mjs
+++ b/scripts/dev-launcher.mjs
@@ -122,7 +122,7 @@ async function main() {
   const child = spawn(
     'npm',
     ['--workspace', 'ui', 'run', 'dev:concurrent'],
-    { cwd: repoRoot, env, stdio: 'inherit' },
+    { cwd: repoRoot, env, stdio: 'inherit', shell: true },
   );
 
   const forward = (signal) => {
diff --git a/ui/package.json b/ui/package.json
index cbbe60bf..80522522 100644
--- a/ui/package.json
+++ b/ui/package.json
@@ -12,6 +12,7 @@
     "dev:gateway": "npm --prefix .. run server",
     "dev:server": "node --import tsx server/index.js",
     "dev:client": "vite",
+    "preserver": "node ../scripts/bootstrap-pilotdeck-config.mjs",
     "server": "node --import tsx server/index.js",
     "gateway": "npm --prefix .. run server",
     "client": "vite",
@@ -20,6 +21,7 @@
     "typecheck": "tsc --noEmit -p tsconfig.json",
     "lint": "eslint src/",
     "lint:fix": "eslint src/ --fix",
+    "prestart": "node ../scripts/bootstrap-pilotdeck-config.mjs",
     "start": "npm run build && npm run start:built",
     "start:built": "concurrently --kill-others --names gateway,server \"npm:gateway\" \"npm:server\"",
     "postinstall": "node scripts/fix-node-pty.js"
diff --git a/ui/server/load-env.js b/ui/server/load-env.js
index 4063ec8c..2c51a872 100644
--- a/ui/server/load-env.js
+++ b/ui/server/load-env.js
@@ -2,6 +2,7 @@ import fs from 'fs';
 import os from 'os';
 import path from 'path';
 import { fileURLToPath } from 'url';
+import { execSync } from 'child_process';
 import {
   applyConfigToProcessEnv,
   getPilotDeckConfigPath,
@@ -18,6 +19,31 @@ const REPO_ROOT = path.resolve(__dirname, '../..');
 // chat execution goes through pilotdeck-bridge.js → src/gateway, which
 // reads ~/.pilotdeck/pilotdeck.yaml directly. The sanity check has been
 // retired; ui/server boots even when the config file is missing.
+// ─── Auto-bootstrap ──────────────────────────────────────────────────────────
+// On first run the ~/.pilotdeck/pilotdeck.yaml config file doesn't exist yet.
+// Rather than relying solely on npm `pre` hooks (which are skipped when the
+// server is started directly, e.g. `node server/index.js` or `pilotdeck start`),
+// we run the bootstrap script inline whenever the config is missing.
+// This ensures Windows users always get the folder + placeholder config
+// regardless of how they launch the project.
+
+function ensurePilotDeckConfigExists() {
+  if (hasPilotDeckConfigFile()) return;
+
+  const bootstrapScript = path.resolve(REPO_ROOT, 'scripts', 'bootstrap-pilotdeck-config.mjs');
+  if (!fs.existsSync(bootstrapScript)) return;
+
+  try {
+    execSync(`node "${bootstrapScript}"`, {
+      stdio: 'inherit',
+      cwd: REPO_ROOT,
+      timeout: 30000,
+      windowsHide: true,
+    });
+  } catch (err) {
+    console.warn('[load-env] Config bootstrap warning:', err instanceof Error ? err.message : String(err));
+  }
+}
 
 function applyDerivedRuntimeEnv() {
   const { config } = readPilotDeckConfigFile();
@@ -45,6 +71,7 @@ export function assertRequiredPilotDeckEnv() {
 }
 
 export function loadRootPilotDeckEnv() {
+  ensurePilotDeckConfigExists();
   applyDerivedRuntimeEnv();
 
   if (!process.env.DATABASE_PATH) {