diff --git a/ccw/src/core/routes/cli-routes.ts b/ccw/src/core/routes/cli-routes.ts
index 29a53a65..2c81b7cd 100644
--- a/ccw/src/core/routes/cli-routes.ts
+++ b/ccw/src/core/routes/cli-routes.ts
@@ -35,6 +35,7 @@ import {
 import {
   loadClaudeCliTools,
   ensureClaudeCliTools,
+  ensureClaudeCliToolsAsync,
   saveClaudeCliTools,
   loadClaudeCliSettings,
   saveClaudeCliSettings,
@@ -329,16 +330,18 @@ export async function handleCliRoutes(ctx: RouteContext): Promise<boolean> {
 
   // API: Get all API endpoints (for --tool custom --model <id>)
   if (pathname === '/api/cli/endpoints' && req.method === 'GET') {
-    try {
-      // Use ensureClaudeCliTools to auto-create config if missing
-      const config = ensureClaudeCliTools(initialPath);
-      const endpoints = getApiEndpointsFromTools(config);
-      res.writeHead(200, { 'Content-Type': 'application/json' });
-      res.end(JSON.stringify({ endpoints }));
-    } catch (err) {
-      res.writeHead(500, { 'Content-Type': 'application/json' });
-      res.end(JSON.stringify({ error: (err as Error).message }));
-    }
+    (async () => {
+      try {
+        // Use ensureClaudeCliToolsAsync to auto-create config with availability sync
+        const config = await ensureClaudeCliToolsAsync(initialPath);
+        const endpoints = getApiEndpointsFromTools(config);
+        res.writeHead(200, { 'Content-Type': 'application/json' });
+        res.end(JSON.stringify({ endpoints }));
+      } catch (err) {
+        res.writeHead(500, { 'Content-Type': 'application/json' });
+        res.end(JSON.stringify({ error: (err as Error).message }));
+      }
+    })();
     return true;
   }
 
@@ -820,21 +823,23 @@ export async function handleCliRoutes(ctx: RouteContext): Promise<boolean> {
 
   // API: Get CLI Tools Config from .claude/cli-tools.json (with fallback to global)
   if (pathname === '/api/cli/tools-config' && req.method === 'GET') {
-    try {
-      // Use ensureClaudeCliTools to auto-create config if missing
-      const toolsConfig = ensureClaudeCliTools(initialPath);
-      const settingsConfig = loadClaudeCliSettings(initialPath);
-      const info = getClaudeCliToolsInfo(initialPath);
-      res.writeHead(200, { 'Content-Type': 'application/json' });
-      res.end(JSON.stringify({
-        tools: toolsConfig,
-        settings: settingsConfig,
-        _configInfo: info
-      }));
-    } catch (err) {
-      res.writeHead(500, { 'Content-Type': 'application/json' });
-      res.end(JSON.stringify({ error: (err as Error).message }));
-    }
+    (async () => {
+      try {
+        // Use ensureClaudeCliToolsAsync to auto-create config with availability sync
+        const toolsConfig = await ensureClaudeCliToolsAsync(initialPath);
+        const settingsConfig = loadClaudeCliSettings(initialPath);
+        const info = getClaudeCliToolsInfo(initialPath);
+        res.writeHead(200, { 'Content-Type': 'application/json' });
+        res.end(JSON.stringify({
+          tools: toolsConfig,
+          settings: settingsConfig,
+          _configInfo: info
+        }));
+      } catch (err) {
+        res.writeHead(500, { 'Content-Type': 'application/json' });
+        res.end(JSON.stringify({ error: (err as Error).message }));
+      }
+    })();
     return true;
   }
 
diff --git a/ccw/src/tools/claude-cli-tools.ts b/ccw/src/tools/claude-cli-tools.ts
index 9aed6810..875c74af 100644
--- a/ccw/src/tools/claude-cli-tools.ts
+++ b/ccw/src/tools/claude-cli-tools.ts
@@ -418,6 +418,56 @@ export function ensureClaudeCliTools(projectDir: string, createInProject: boolea
   }
 }
 
+/**
+ * Async version of ensureClaudeCliTools with automatic availability sync
+ * Creates default config in global ~/.claude directory and syncs with actual tool availability
+ * @param projectDir - Project directory path (used for reading existing project config)
+ * @param createInProject - DEPRECATED: Always creates in global dir. Kept for backward compatibility.
+ * @returns The config that was created/exists
+ */
+export async function ensureClaudeCliToolsAsync(projectDir: string, createInProject: boolean = false): Promise<ClaudeCliToolsConfig & { _source?: string }> {
+  const resolved = resolveConfigPath(projectDir);
+
+  if (resolved.source !== 'default') {
+    // Config exists, load and return it
+    return loadClaudeCliTools(projectDir);
+  }
+
+  // Config doesn't exist - create in global directory only
+  debugLog('[claude-cli-tools] Config not found, creating default cli-tools.json in ~/.claude');
+
+  const defaultConfig: ClaudeCliToolsConfig = { ...DEFAULT_TOOLS_CONFIG };
+
+  // Always create in global directory (user-level config), respecting CCW_DATA_DIR
+  const claudeHome = process.env.CCW_DATA_DIR
+    ? path.join(process.env.CCW_DATA_DIR, '.claude')
+    : path.join(os.homedir(), '.claude');
+  if (!fs.existsSync(claudeHome)) {
+    fs.mkdirSync(claudeHome, { recursive: true });
+  }
+  const globalPath = getGlobalConfigPath();
+  try {
+    fs.writeFileSync(globalPath, JSON.stringify(defaultConfig, null, 2), 'utf-8');
+    debugLog(`[claude-cli-tools] Created default config at: ${globalPath}`);
+
+    // Auto-sync with actual tool availability on first creation
+    try {
+      debugLog('[claude-cli-tools] Auto-syncing tool availability on first creation...');
+      const syncResult = await syncBuiltinToolsAvailability(projectDir);
+      debugLog(`[claude-cli-tools] Auto-sync completed: enabled=[${syncResult.changes.enabled.join(', ')}], disabled=[${syncResult.changes.disabled.join(', ')}]`);
+      return { ...syncResult.config, _source: 'global' };
+    } catch (syncErr) {
+      console.warn('[claude-cli-tools] Failed to auto-sync availability:', syncErr);
+      // Return default config if sync fails
+      return { ...defaultConfig, _source: 'global' };
+    }
+  } catch (err) {
+    console.error('[claude-cli-tools] Failed to create global config:', err);
+    return { ...defaultConfig, _source: 'default' };
+  }
+}
+
+
 /**
  * Load CLI tools configuration from global ~/.claude/cli-tools.json
  * Falls back to default config if not found.