diff --git a/packages/main/src/plugin/agent-workspace/agent-workspace-manager.spec.ts b/packages/main/src/plugin/agent-workspace/agent-workspace-manager.spec.ts
index 3d668975c..6be4c02a8 100644
--- a/packages/main/src/plugin/agent-workspace/agent-workspace-manager.spec.ts
+++ b/packages/main/src/plugin/agent-workspace/agent-workspace-manager.spec.ts
@@ -89,6 +89,7 @@ const openshellCli = new OpenshellCli({} as Exec, {} as CliToolRegistry);
 
 const agentRegistry = {
   getAgentRegistration: vi.fn(),
+  getAgent: vi.fn(),
 } as unknown as AgentRegistry;
 
 const mockTask = {
@@ -1206,6 +1207,149 @@ describe('dispose', () => {
   });
 });
 
+describe('terminal agent command execution', () => {
+  const SANDBOXES_WITH_AGENT: GatewaySandboxes[] = [
+    {
+      gateway: { name: 'kaiden', endpoint: 'http://localhost:10080' },
+      sandboxes: [
+        {
+          id: 'ws-agent',
+          name: 'agent-workspace',
+          phase: 'Ready',
+          labels: { [AGENT_LABEL]: 'test-agent' },
+        },
+        {
+          id: 'ws-no-label',
+          name: 'no-label-workspace',
+          phase: 'Ready',
+        },
+      ],
+    },
+  ];
+
+  function createTerminalMockPty(): { pty: IPty; triggerData: (data: string) => void } {
+    let onDataCb: ((data: string) => void) | undefined;
+    const pty = {
+      onData: vi.fn((cb: (data: string) => void) => {
+        onDataCb = cb;
+        return { dispose: vi.fn() };
+      }),
+      onExit: vi.fn(() => ({ dispose: vi.fn() })),
+      write: vi.fn(),
+      resize: vi.fn(),
+      kill: vi.fn(),
+      pid: 456,
+    } as unknown as IPty;
+    return {
+      pty,
+      triggerData: (data: string): void => {
+        onDataCb?.(data);
+      },
+    };
+  }
+
+  function getTerminalHandler(): (_listener: unknown, id: string, onDataId: number) => Promise<number> {
+    return vi.mocked(ipcHandle).mock.calls.find(call => call[0] === 'agent-workspace:terminal')![1] as (
+      _listener: unknown,
+      id: string,
+      onDataId: number,
+    ) => Promise<number>;
+  }
+
+  test('executes agent command on first terminal data', async () => {
+    vi.mocked(openshellCli.listSandboxesPerGateway).mockResolvedValue(SANDBOXES_WITH_AGENT);
+    vi.mocked(agentRegistry.getAgent).mockResolvedValue({
+      id: 'test-agent',
+      name: 'Test Agent',
+      description: '',
+      command: '/usr/bin/agent start',
+      destinationSkillsFolder: '~/.agent',
+    });
+    const { pty, triggerData } = createTerminalMockPty();
+    vi.mocked(spawn).mockReturnValue(pty);
+
+    await getTerminalHandler()({}, 'ws-agent', 10);
+    triggerData('$ ');
+
+    expect(pty.write).toHaveBeenCalledWith('/usr/bin/agent start\n');
+  });
+
+  test('does not execute agent command on subsequent connections', async () => {
+    vi.mocked(openshellCli.listSandboxesPerGateway).mockResolvedValue(SANDBOXES_WITH_AGENT);
+    vi.mocked(agentRegistry.getAgent).mockResolvedValue({
+      id: 'test-agent',
+      name: 'Test Agent',
+      description: '',
+      command: '/usr/bin/agent start',
+      destinationSkillsFolder: '~/.agent',
+    });
+    const { pty: pty1, triggerData: triggerData1 } = createTerminalMockPty();
+    vi.mocked(spawn).mockReturnValue(pty1);
+
+    await getTerminalHandler()({}, 'ws-agent', 10);
+    triggerData1('$ ');
+
+    const { pty: pty2, triggerData: triggerData2 } = createTerminalMockPty();
+    vi.mocked(spawn).mockReturnValue(pty2);
+
+    await getTerminalHandler()({}, 'ws-agent', 11);
+    triggerData2('$ ');
+
+    expect(pty2.write).not.toHaveBeenCalled();
+  });
+
+  test('does not execute command when workspace has no agent label', async () => {
+    vi.mocked(openshellCli.listSandboxesPerGateway).mockResolvedValue(SANDBOXES_WITH_AGENT);
+    const { pty, triggerData } = createTerminalMockPty();
+    vi.mocked(spawn).mockReturnValue(pty);
+
+    await getTerminalHandler()({}, 'ws-no-label', 10);
+    triggerData('$ ');
+
+    expect(pty.write).not.toHaveBeenCalled();
+    expect(agentRegistry.getAgent).not.toHaveBeenCalled();
+  });
+
+  test('does not execute command when agent has no command', async () => {
+    vi.mocked(openshellCli.listSandboxesPerGateway).mockResolvedValue(SANDBOXES_WITH_AGENT);
+    vi.mocked(agentRegistry.getAgent).mockResolvedValue({
+      id: 'test-agent',
+      name: 'Test Agent',
+      description: '',
+      command: '',
+      destinationSkillsFolder: '~/.agent',
+    });
+    const { pty, triggerData } = createTerminalMockPty();
+    vi.mocked(spawn).mockReturnValue(pty);
+
+    await getTerminalHandler()({}, 'ws-agent', 10);
+    triggerData('$ ');
+
+    expect(pty.write).not.toHaveBeenCalled();
+  });
+
+  test('executes agent command only once despite multiple data events', async () => {
+    vi.mocked(openshellCli.listSandboxesPerGateway).mockResolvedValue(SANDBOXES_WITH_AGENT);
+    vi.mocked(agentRegistry.getAgent).mockResolvedValue({
+      id: 'test-agent',
+      name: 'Test Agent',
+      description: '',
+      command: '/usr/bin/agent start',
+      destinationSkillsFolder: '~/.agent',
+    });
+    const { pty, triggerData } = createTerminalMockPty();
+    vi.mocked(spawn).mockReturnValue(pty);
+
+    await getTerminalHandler()({}, 'ws-agent', 10);
+    triggerData('$ ');
+    triggerData('more output');
+    triggerData('even more output');
+
+    expect(pty.write).toHaveBeenCalledTimes(1);
+    expect(pty.write).toHaveBeenCalledWith('/usr/bin/agent start\n');
+  });
+});
+
 describe('encodeWorkspaceLabels', () => {
   test('returns single label for short paths', () => {
     const labels = encodeWorkspaceLabels('/tmp/my-project');
diff --git a/packages/main/src/plugin/agent-workspace/agent-workspace-manager.ts b/packages/main/src/plugin/agent-workspace/agent-workspace-manager.ts
index 6137beb8a..f6c567423 100644
--- a/packages/main/src/plugin/agent-workspace/agent-workspace-manager.ts
+++ b/packages/main/src/plugin/agent-workspace/agent-workspace-manager.ts
@@ -80,6 +80,7 @@ export class AgentWorkspaceManager implements Disposable {
     { write: (param: string) => void; resize: (w: number, h: number) => void }
   >();
   private readonly terminalProcesses = new Map<number, IPty>();
+  private readonly commandExecutedWorkspaces = new Set<string>();
 
   constructor(
     @inject(ApiSenderType)
@@ -398,6 +399,7 @@ export class AgentWorkspaceManager implements Disposable {
     task.status = 'in-progress';
     try {
       await this.openshellCli.deleteSandbox(workspaceName);
+      this.commandExecutedWorkspaces.delete(id);
       this.apiSender.send('agent-workspace-update');
       task.status = 'success';
       return { id };
@@ -603,12 +605,36 @@ export class AgentWorkspaceManager implements Disposable {
         if (!workspace) {
           throw new Error(`workspace "${id}" not found. Use "workspace list" to see available workspaces.`);
         }
+
+        const shouldExecuteCommand = !this.commandExecutedWorkspaces.has(id);
+        let agentCommand: string | undefined;
+        if (shouldExecuteCommand && workspace.labels) {
+          const agentId = workspace.labels[AGENT_LABEL];
+          if (agentId) {
+            try {
+              const agent = await this.agentRegistry.getAgent(agentId);
+              agentCommand = agent?.command;
+            } catch (err: unknown) {
+              console.error(`Failed to resolve agent command for workspace "${id}":`, err);
+            }
+          }
+        }
+
+        if (agentCommand) {
+          this.commandExecutedWorkspaces.add(id);
+        }
+
+        let commandSent = false;
         const invocation = this.shellInAgentWorkspace(
           workspace.name,
           (content: string) => {
             if (!this.webContents.isDestroyed()) {
               this.webContents.send('agent-workspace:terminal-onData', onDataId, content);
             }
+            if (!commandSent && agentCommand) {
+              commandSent = true;
+              invocation.write(`${agentCommand}\n`);
+            }
           },
           (error: string) => {
             if (!this.webContents.isDestroyed()) {
@@ -689,5 +715,6 @@ export class AgentWorkspaceManager implements Disposable {
     }
     this.terminalProcesses.clear();
     this.terminalCallbacks.clear();
+    this.commandExecutedWorkspaces.clear();
   }
 }