diff --git a/web/src/server/server.ts b/web/src/server/server.ts
index efebd894..0939b833 100644
--- a/web/src/server/server.ts
+++ b/web/src/server/server.ts
@@ -910,8 +910,8 @@ let serverStarted = false;
 
 // Export a function to start the server
 export async function startVibeTunnelServer() {
-  // Initialize logger first (we'll set debug mode after parsing args)
-  initLogger(false);
+  // Initialize logger if not already initialized (preserves debug mode from CLI)
+  initLogger();
 
   // Prevent multiple server instances
   if (serverStarted) {
diff --git a/web/src/server/utils/logger.ts b/web/src/server/utils/logger.ts
index 9ab85b1d..2ae970a7 100644
--- a/web/src/server/utils/logger.ts
+++ b/web/src/server/utils/logger.ts
@@ -23,6 +23,11 @@ const ANSI_PATTERN = /\x1b\[[0-9;]*m/g;
 export function initLogger(debug: boolean = false): void {
   debugMode = debug;
 
+  // If already initialized, just update debug mode and return
+  if (logFileHandle) {
+    return;
+  }
+
   try {
     // Ensure log directory exists
     if (!fs.existsSync(LOG_DIR)) {