diff --git a/src/gateway/server/ws-connection/message-handler.ts b/src/gateway/server/ws-connection/message-handler.ts
index 948d6cefb..5c91c4eb9 100644
--- a/src/gateway/server/ws-connection/message-handler.ts
+++ b/src/gateway/server/ws-connection/message-handler.ts
@@ -664,12 +664,25 @@ export function attachGatewayWsMessageHandler(params: {
                 requestId: pairing.request.requestId,
                 reason,
               });
+              const helpMessage = 
+                `Device pairing required. ` +
+                `On the OpenClaw server machine, run: ` +
+                `'openclaw devices list' to see pending requests, then ` +
+                `'openclaw devices approve ${pairing.request.requestId}' to approve this device. ` +
+                `Alternatively, access the Control UI from the server's localhost to approve.`;
               send({
                 type: "res",
                 id: frame.id,
                 ok: false,
-                error: errorShape(ErrorCodes.NOT_PAIRED, "pairing required", {
-                  details: { requestId: pairing.request.requestId },
+                error: errorShape(ErrorCodes.NOT_PAIRED, helpMessage, {
+                  details: { 
+                    requestId: pairing.request.requestId,
+                    deviceId: device.id,
+                    instructions: {
+                      list: "openclaw devices list",
+                      approve: `openclaw devices approve ${pairing.request.requestId}`,
+                    }
+                  },
                 }),
               });
               close(1008, "pairing required");
diff --git a/ui/src/ui/gateway.ts b/ui/src/ui/gateway.ts
index fc8dde08a..122df9fea 100644
--- a/ui/src/ui/gateway.ts
+++ b/ui/src/ui/gateway.ts
@@ -219,11 +219,13 @@ export class GatewayBrowserClient {
         this.backoffMs = 800;
         this.opts.onHello?.(hello);
       })
-      .catch(() => {
+      .catch((err) => {
         if (canFallbackToShared && deviceIdentity) {
           clearDeviceAuthToken({ deviceId: deviceIdentity.deviceId, role });
         }
-        this.ws?.close(CONNECT_FAILED_CLOSE_CODE, "connect failed");
+        // Extract the error message to pass to onClose handler
+        const errorMessage = err instanceof Error ? err.message : "connect failed";
+        this.ws?.close(CONNECT_FAILED_CLOSE_CODE, errorMessage);
       });
   }