diff --git a/ccw/src/commands/cli.ts b/ccw/src/commands/cli.ts
index 1de7e568..01769b5f 100644
--- a/ccw/src/commands/cli.ts
+++ b/ccw/src/commands/cli.ts
@@ -43,6 +43,7 @@ function notifyDashboard(data: Record<string, unknown>): void {
     port: Number(DASHBOARD_PORT),
     path: '/api/hook',
     method: 'POST',
+    timeout: 2000, // 2 second timeout to prevent hanging
     headers: {
       'Content-Type': 'application/json',
       'Content-Length': Buffer.byteLength(payload)
@@ -53,6 +54,10 @@ function notifyDashboard(data: Record<string, unknown>): void {
   req.on('error', (err) => {
     if (process.env.DEBUG) console.error('[Dashboard] CLI notification failed:', err.message);
   });
+  req.on('timeout', () => {
+    req.destroy();
+    if (process.env.DEBUG) console.error('[Dashboard] CLI notification timed out');
+  });
   req.write(payload);
   req.end();
 }
diff --git a/ccw/src/tools/cli-executor.ts b/ccw/src/tools/cli-executor.ts
index ef052a90..7b986c92 100644
--- a/ccw/src/tools/cli-executor.ts
+++ b/ccw/src/tools/cli-executor.ts
@@ -796,7 +796,7 @@ async function executeCliTool(
     });
 
     // Handle completion
-    child.on('close', (code) => {
+    child.on('close', async (code) => {
       const endTime = Date.now();
       const duration = endTime - startTime;
 
@@ -942,29 +942,28 @@ async function executeCliTool(
         }
       }
 
-      // Track native session after execution (async, non-blocking)
+      // Track native session after execution (awaited to prevent process hang)
       // Pass prompt for precise matching in parallel execution scenarios
-      trackNewSession(tool, new Date(startTime), workingDir, prompt)
-        .then((nativeSession) => {
-          if (nativeSession) {
-            // Save native session mapping
-            try {
-              store.saveNativeSessionMapping({
-                ccw_id: conversationId,
-                tool,
-                native_session_id: nativeSession.sessionId,
-                native_session_path: nativeSession.filePath,
-                project_hash: nativeSession.projectHash,
-                created_at: new Date().toISOString()
-              });
-            } catch (err) {
-              console.error('[CLI Executor] Failed to save native session mapping:', (err as Error).message);
-            }
+      try {
+        const nativeSession = await trackNewSession(tool, new Date(startTime), workingDir, prompt);
+        if (nativeSession) {
+          // Save native session mapping
+          try {
+            store.saveNativeSessionMapping({
+              ccw_id: conversationId,
+              tool,
+              native_session_id: nativeSession.sessionId,
+              native_session_path: nativeSession.filePath,
+              project_hash: nativeSession.projectHash,
+              created_at: new Date().toISOString()
+            });
+          } catch (err) {
+            console.error('[CLI Executor] Failed to save native session mapping:', (err as Error).message);
           }
-        })
-        .catch((err) => {
-          console.error('[CLI Executor] Failed to track native session:', (err as Error).message);
-        });
+        }
+      } catch (err) {
+        console.error('[CLI Executor] Failed to track native session:', (err as Error).message);
+      }
 
       // Create legacy execution record for backward compatibility
       const execution: ExecutionRecord = {