diff --git a/packages/main/src/plugin/openshell-cli/openshell-gateway.spec.ts b/packages/main/src/plugin/openshell-cli/openshell-gateway.spec.ts
index f1c037425a..e2771c3a7f 100644
--- a/packages/main/src/plugin/openshell-cli/openshell-gateway.spec.ts
+++ b/packages/main/src/plugin/openshell-cli/openshell-gateway.spec.ts
@@ -82,6 +82,7 @@ const openshellCli = {
   selectGateway: vi.fn(),
   checkEndpointStatus: vi.fn(),
   addGateway: vi.fn(),
+  removeGateway: vi.fn(),
 } as unknown as OpenshellCli;
 
 const directories = {
@@ -105,6 +106,8 @@ beforeEach(() => {
   ] as unknown as CliToolInfo[]);
   vi.mocked(createWriteStream).mockReturnValue(gatewayLogStream);
   vi.mocked(exec.exec).mockResolvedValue({ command: '', stdout: '', stderr: '' });
+  vi.mocked(openshellCli.removeGateway).mockResolvedValue();
+  vi.mocked(openshellCli.listGateways).mockResolvedValue([]);
   gateway = new OpenshellGateway(cliToolRegistry, openshellCli, directories, exec, notificationRegistry);
 });
 
@@ -423,6 +426,84 @@ describe('start', () => {
     });
   });
 
+  test('skips re-registration when kaiden-local already exists with same endpoint', async () => {
+    vi.spyOn(console, 'log').mockImplementation(() => undefined);
+    const proc = createMockChildProcess();
+    vi.mocked(spawn).mockReturnValue(proc);
+    vi.mocked(exec.exec).mockResolvedValue(mockExecResult('openshell-gateway 0.0.69'));
+    vi.mocked(openshellCli.checkEndpointStatus).mockResolvedValue(true);
+    vi.mocked(openshellCli.listGateways).mockResolvedValue([
+      { name: 'kaiden-local', endpoint: 'http://127.0.0.1:17670' } as GatewayInfo,
+    ]);
+
+    await gateway.start();
+
+    expect(openshellCli.removeGateway).not.toHaveBeenCalled();
+    expect(openshellCli.addGateway).not.toHaveBeenCalled();
+  });
+
+  test('removes stale gateway and re-registers when endpoint differs', async () => {
+    vi.spyOn(console, 'log').mockImplementation(() => undefined);
+    const proc = createMockChildProcess();
+    vi.mocked(spawn).mockReturnValue(proc);
+    vi.mocked(exec.exec).mockResolvedValue(mockExecResult('openshell-gateway 0.0.69'));
+    vi.mocked(openshellCli.checkEndpointStatus).mockResolvedValue(true);
+    vi.mocked(openshellCli.listGateways).mockResolvedValue([
+      { name: 'kaiden-local', endpoint: 'http://127.0.0.1:9999' } as GatewayInfo,
+    ]);
+
+    await gateway.start();
+
+    expect(openshellCli.removeGateway).toHaveBeenCalledWith('kaiden-local');
+    expect(openshellCli.addGateway).toHaveBeenCalledWith({
+      endpoint: 'http://127.0.0.1:17670',
+      local: true,
+      name: 'kaiden-local',
+    });
+
+    const removeOrder = vi.mocked(openshellCli.removeGateway).mock.invocationCallOrder[0]!;
+    const addOrder = vi.mocked(openshellCli.addGateway).mock.invocationCallOrder[0]!;
+    expect(removeOrder).toBeLessThan(addOrder);
+  });
+
+  test('registers fresh when kaiden-local does not exist', async () => {
+    vi.spyOn(console, 'log').mockImplementation(() => undefined);
+    const proc = createMockChildProcess();
+    vi.mocked(spawn).mockReturnValue(proc);
+    vi.mocked(exec.exec).mockResolvedValue(mockExecResult('openshell-gateway 0.0.69'));
+    vi.mocked(openshellCli.checkEndpointStatus).mockResolvedValue(true);
+    vi.mocked(openshellCli.listGateways).mockResolvedValue([]);
+
+    await gateway.start();
+
+    expect(openshellCli.removeGateway).not.toHaveBeenCalled();
+    expect(openshellCli.addGateway).toHaveBeenCalledWith({
+      endpoint: 'http://127.0.0.1:17670',
+      local: true,
+      name: 'kaiden-local',
+    });
+  });
+
+  test('registers successfully even when removeGateway fails', async () => {
+    vi.spyOn(console, 'log').mockImplementation(() => undefined);
+    const proc = createMockChildProcess();
+    vi.mocked(spawn).mockReturnValue(proc);
+    vi.mocked(exec.exec).mockResolvedValue(mockExecResult('openshell-gateway 0.0.69'));
+    vi.mocked(openshellCli.checkEndpointStatus).mockResolvedValue(true);
+    vi.mocked(openshellCli.listGateways).mockResolvedValue([
+      { name: 'kaiden-local', endpoint: 'http://127.0.0.1:9999' } as GatewayInfo,
+    ]);
+    vi.mocked(openshellCli.removeGateway).mockRejectedValue(new Error('no such gateway'));
+
+    await gateway.start();
+
+    expect(openshellCli.addGateway).toHaveBeenCalledWith({
+      endpoint: 'http://127.0.0.1:17670',
+      local: true,
+      name: 'kaiden-local',
+    });
+  });
+
   test('skips registerWithCli when skipRegistration is true', async () => {
     vi.spyOn(console, 'log').mockImplementation(() => undefined);
     const proc = createMockChildProcess();
diff --git a/packages/main/src/plugin/openshell-cli/openshell-gateway.ts b/packages/main/src/plugin/openshell-cli/openshell-gateway.ts
index 7028f8470a..3fcc72c628 100644
--- a/packages/main/src/plugin/openshell-cli/openshell-gateway.ts
+++ b/packages/main/src/plugin/openshell-cli/openshell-gateway.ts
@@ -366,6 +366,15 @@ export class OpenshellGateway implements Disposable {
   private async registerWithCli(): Promise<void> {
     const endpoint = `http://${this.#bindAddress}:${this.#port}`;
     try {
+      const gateways = await this.openshellCli.listGateways();
+      const existing = gateways.find(gw => gw.name === 'kaiden-local');
+      if (existing) {
+        if (existing.endpoint === endpoint) {
+          console.log(`[openshell-gateway] kaiden-local already registered at ${endpoint}`);
+          return;
+        }
+        await this.openshellCli.removeGateway('kaiden-local').catch(() => {});
+      }
       await this.openshellCli.addGateway({ endpoint, local: true, name: 'kaiden-local' });
       console.log(`[openshell-gateway] registered with CLI as kaiden-local at ${endpoint}`);
     } catch (err: unknown) {