diff --git a/src/gateway/r2.test.ts b/src/gateway/r2.test.ts
index 83b03ae43..e6d3a55b4 100644
--- a/src/gateway/r2.test.ts
+++ b/src/gateway/r2.test.ts
@@ -142,6 +142,25 @@ describe('mountR2Storage', () => {
       expect(console.error).toHaveBeenCalledWith('Failed to mount R2 bucket:', expect.any(Error));
     });
 
+    it('returns true when mount fails with "already in use" error', async () => {
+      const { sandbox, mountBucketMock, startProcessMock } = createMockSandbox({ mounted: false });
+      mountBucketMock.mockRejectedValue(
+        new Error('InvalidMountConfigError: Mount path "/data/moltbot" is already in use by bucket "moltbot-data". Unmount the existing bucket first or use a different mount path.'),
+      );
+      startProcessMock.mockResolvedValueOnce(createMockProcess(''));
+
+      const env = createMockEnvWithR2();
+
+      const result = await mountR2Storage(sandbox, env);
+
+      expect(result).toBe(true);
+      expect(console.log).toHaveBeenCalledWith(
+        'R2 bucket already mounted at',
+        '/data/moltbot',
+        '(detected via mount error)',
+      );
+    });
+
     it('returns true if mount fails but check shows it is actually mounted', async () => {
       const { sandbox, mountBucketMock, startProcessMock } = createMockSandbox();
       startProcessMock
diff --git a/src/gateway/r2.ts b/src/gateway/r2.ts
index c95efc40b..124dabe11 100644
--- a/src/gateway/r2.ts
+++ b/src/gateway/r2.ts
@@ -65,6 +65,12 @@ export async function mountR2Storage(sandbox: Sandbox, env: MoltbotEnv): Promise
     const errorMessage = err instanceof Error ? err.message : String(err);
     console.log('R2 mount error:', errorMessage);
 
+    // "already in use" means the bucket is mounted — treat as success
+    if (errorMessage.includes('already in use')) {
+      console.log('R2 bucket already mounted at', R2_MOUNT_PATH, '(detected via mount error)');
+      return true;
+    }
+
     // Check again if it's mounted - the error might be misleading
     if (await isR2Mounted(sandbox)) {
       console.log('R2 bucket is mounted despite error');
diff --git a/src/gateway/sync.test.ts b/src/gateway/sync.test.ts
index f062ffed7..b8a89aaef 100644
--- a/src/gateway/sync.test.ts
+++ b/src/gateway/sync.test.ts
@@ -1,4 +1,4 @@
-import { describe, it, expect, beforeEach } from 'vitest';
+import { describe, it, expect, beforeEach, vi } from 'vitest';
 import { syncToR2 } from './sync';
 import {
   createMockEnv,
@@ -8,6 +8,10 @@ import {
   suppressConsole,
 } from '../test-utils';
 
+vi.mock('./process', () => ({
+  ensureMoltbotGateway: vi.fn().mockResolvedValue({ id: 'mock-process' }),
+}));
+
 describe('syncToR2', () => {
   beforeEach(() => {
     suppressConsole();
diff --git a/src/gateway/sync.ts b/src/gateway/sync.ts
index 63808c471..cfc4c48de 100644
--- a/src/gateway/sync.ts
+++ b/src/gateway/sync.ts
@@ -1,6 +1,7 @@
 import type { Sandbox } from '@cloudflare/sandbox';
 import type { MoltbotEnv } from '../types';
 import { R2_MOUNT_PATH } from '../config';
+import { ensureMoltbotGateway } from './process';
 import { mountR2Storage } from './r2';
 import { waitForProcess } from './utils';
 
@@ -35,6 +36,18 @@ export async function syncToR2(sandbox: Sandbox, env: MoltbotEnv): Promise<SyncR
     return { success: false, error: 'R2 storage is not configured' };
   }
 
+  // Ensure the gateway is running — the startup script creates the config
+  // file via `openclaw onboard`, which is required before we can sync
+  try {
+    await ensureMoltbotGateway(sandbox, env);
+  } catch (err) {
+    return {
+      success: false,
+      error: 'Failed to start gateway',
+      details: err instanceof Error ? err.message : 'Unknown error',
+    };
+  }
+
   // Mount R2 if not already mounted
   const mounted = await mountR2Storage(sandbox, env);
   if (!mounted) {