diff --git a/src/tools/builtin/messaging.ts b/src/tools/builtin/messaging.ts
index c3bedec..dc7e368 100644
--- a/src/tools/builtin/messaging.ts
+++ b/src/tools/builtin/messaging.ts
@@ -6,15 +6,15 @@ import { z } from 'zod';
 function detectRole(): string {
   const cwd = process.cwd();
 
-  // Check for specific workspace patterns with leading slash
-  if (cwd.includes('/joylo-admin')) return 'admin-dev';
-  if (cwd.includes('/joylo-api')) return 'api-dev';
-  if (cwd.includes('/joylo-web')) return 'web-dev';
+  // Match patterns - check most specific first
+  if (cwd.includes('joylo-admin') || cwd.includes('joylo/admin')) return 'admin-dev';
+  if (cwd.includes('joylo-api') || cwd.includes('joylo/api')) return 'api-dev';
+  if (cwd.includes('joylo-web') || cwd.includes('joylo/web')) return 'web-dev';
 
-  // Fallback for different path formats
-  if (cwd.match(/admin/i)) return 'admin-dev';
-  if (cwd.match(/api/i)) return 'api-dev';
-  if (cwd.match(/web/i)) return 'web-dev';
+  // Fallback regex
+  if (/admin/i.test(cwd)) return 'admin-dev';
+  if (/\bapi\b/i.test(cwd)) return 'api-dev';
+  if (/\bweb\b/i.test(cwd)) return 'web-dev';
 
   return 'unknown';
 }