diff --git a/electron/gateway/manager.ts b/electron/gateway/manager.ts
index cf96d3c25..eec06d333 100644
--- a/electron/gateway/manager.ts
+++ b/electron/gateway/manager.ts
@@ -337,7 +337,11 @@ export class GatewayManager extends EventEmitter {
     });
 
     try {
+      let startAttempts = 0;
+      const MAX_START_ATTEMPTS = 3;
+
       while (true) {
+        startAttempts++;
         this.assertLifecycleEpoch(startEpoch, 'start');
         this.recentStartupStderrLines = [];
         try {
@@ -390,6 +394,22 @@ export class GatewayManager extends EventEmitter {
             }
             logger.error('OpenClaw doctor repair failed; not retrying Gateway startup');
           }
+
+          // Retry on transient connect errors
+          const errMsg = String(error);
+          const isTransientError =
+            errMsg.includes('WebSocket closed before handshake') ||
+            errMsg.includes('ECONNREFUSED') ||
+            errMsg.includes('Gateway process exited before becoming ready') ||
+            errMsg.includes('Timed out waiting for connect.challenge') ||
+            errMsg.includes('Connect handshake timeout');
+
+          if (startAttempts < MAX_START_ATTEMPTS && isTransientError) {
+            logger.warn(`Transient start error: ${errMsg}. Retrying... (${startAttempts}/${MAX_START_ATTEMPTS})`);
+            await new Promise((r) => setTimeout(r, 1000));
+            continue;
+          }
+
           throw error;
         }
       }
diff --git a/electron/main/ipc-handlers.ts b/electron/main/ipc-handlers.ts
index 891c127e0..ae3bc1af2 100644
--- a/electron/main/ipc-handlers.ts
+++ b/electron/main/ipc-handlers.ts
@@ -1312,7 +1312,10 @@ function registerProviderHandlers(gatewayManager: GatewayManager): void {
           }
 
           // Debounced restart so the gateway picks up the new default provider.
-          if (gatewayManager.isConnected()) {
+          // Because OAuth success triggers a debounced restart, the gateway might not be
+          // currently connected ('starting' or 'reconnecting'). Checking if it is simply
+          // not 'stopped' ensures the restart request is correctly queued or coalesced.
+          if (gatewayManager.getStatus().state !== 'stopped') {
             logger.info(`Scheduling Gateway restart after provider switch to "${ock}"`);
             gatewayManager.debouncedRestart();
           }