diff --git a/gsd-openclaw/src/gsd_openclaw/orchestrator.py b/gsd-openclaw/src/gsd_openclaw/orchestrator.py
index 3fc2406..5043d83 100644
--- a/gsd-openclaw/src/gsd_openclaw/orchestrator.py
+++ b/gsd-openclaw/src/gsd_openclaw/orchestrator.py
@@ -83,6 +83,17 @@ class Orchestrator:
             self.user_context_managers[user_id] = UserContextManager(user_id, self._users_root)
         return self.user_context_managers[user_id]
 
+    def _is_long_command(self, command: str) -> bool:
+        """Check if command requires no timeout.
+
+        Args:
+            command: The command name (e.g., 'execute-phase', 'status').
+
+        Returns:
+            True if command is in LONG_COMMANDS, False otherwise.
+        """
+        return command in self.LONG_COMMANDS
+
     def _handle_new_project(self, user_id: str, project_name: str) -> Dict[str, Any]:
         """Handle /gsd:new-project command.
 
@@ -273,8 +284,11 @@ class Orchestrator:
             if args:
                 full_command = f"{full_command} {args}"
 
-            # Execute command
-            result = self.executor.execute(session, full_command)
+            # Determine timeout based on command type
+            timeout = None if self._is_long_command(command) else self.executor.DEFAULT_TIMEOUT
+
+            # Execute command with adaptive timeout
+            result = self.executor.execute(session, full_command, timeout=timeout)
 
             # Truncate output if needed
             output = result.output
diff --git a/gsd-openclaw/tests/test_orchestrator.py b/gsd-openclaw/tests/test_orchestrator.py
index 71ab572..4433a98 100644
--- a/gsd-openclaw/tests/test_orchestrator.py
+++ b/gsd-openclaw/tests/test_orchestrator.py
@@ -848,3 +848,160 @@ class TestSpecialCommands:
 
         # Verify get_session was called with the project from user context
         orch.tmux_manager.get_session.assert_called_with("context-project")
+
+
+class TestAdaptiveTimeout:
+    """Tests for adaptive timeout based on command type."""
+
+    @pytest.fixture
+    def orchestrator_with_mocks(self):
+        """Create orchestrator with mocked dependencies for timeout tests."""
+        from gsd_openclaw.orchestrator import Orchestrator
+
+        mock_tmux_manager = MagicMock()
+        mock_formatter = MagicMock()
+        mock_executor = MagicMock()
+        mock_executor.DEFAULT_TIMEOUT = 60.0  # Set real timeout value on mock
+
+        orchestrator = Orchestrator(
+            tmux_manager=mock_tmux_manager,
+            formatter=mock_formatter
+        )
+        orchestrator.executor = mock_executor
+
+        return orchestrator
+
+    def test_orchestrator_has_long_commands_set(self, orchestrator_with_mocks):
+        """Orchestrator should have LONG_COMMANDS set defined."""
+        orch = orchestrator_with_mocks
+
+        assert hasattr(orch, 'LONG_COMMANDS')
+        assert 'execute-phase' in orch.LONG_COMMANDS
+        assert 'plan-phase' in orch.LONG_COMMANDS
+        assert 'discuss-phase' in orch.LONG_COMMANDS
+        assert 'new-project' in orch.LONG_COMMANDS
+
+    def test_is_long_command_returns_true_for_long_commands(self, orchestrator_with_mocks):
+        """_is_long_command should return True for commands in LONG_COMMANDS."""
+        orch = orchestrator_with_mocks
+
+        assert orch._is_long_command('execute-phase') is True
+        assert orch._is_long_command('plan-phase') is True
+        assert orch._is_long_command('discuss-phase') is True
+        assert orch._is_long_command('new-project') is True
+
+    def test_is_long_command_returns_false_for_regular_commands(self, orchestrator_with_mocks):
+        """_is_long_command should return False for commands not in LONG_COMMANDS."""
+        orch = orchestrator_with_mocks
+
+        assert orch._is_long_command('status') is False
+        assert orch._is_long_command('list') is False
+        assert orch._is_long_command('help') is False
+        assert orch._is_long_command('use') is False
+
+    def test_execute_called_with_none_timeout_for_long_commands(self, orchestrator_with_mocks):
+        """execute() should be called with timeout=None for long commands."""
+        from gsd_openclaw.tmux_session import TmuxSession
+
+        orch = orchestrator_with_mocks
+
+        mock_session = MagicMock(spec=TmuxSession)
+        mock_session.session_id = "test-123"
+        mock_session.tmux_session = MagicMock()
+        mock_session.tmux_session.active_pane = MagicMock()
+        orch.tmux_manager.get_session.return_value = mock_session
+
+        orch.executor.execute.return_value = CommandResult(
+            output="Executing phase...",
+            completed=True,
+            has_error=False,
+            error_type=None
+        )
+        orch.formatter.format_success.return_value = {"card": "success"}
+
+        # Call a long command
+        result = orch.handle_message(
+            user_id="user1",
+            message="/gsd:execute-phase 01-core",
+            channel="test-channel",
+            context={"project": "test-project"}
+        )
+
+        # Verify execute was called with timeout=None
+        call_args = orch.executor.execute.call_args
+        assert call_args[1].get('timeout') is None
+
+    def test_execute_called_with_default_timeout_for_regular_commands(self, orchestrator_with_mocks):
+        """execute() should be called with DEFAULT_TIMEOUT for regular commands."""
+        from gsd_openclaw.tmux_session import TmuxSession
+
+        orch = orchestrator_with_mocks
+
+        mock_session = MagicMock(spec=TmuxSession)
+        mock_session.session_id = "test-123"
+        mock_session.tmux_session = MagicMock()
+        mock_session.tmux_session.active_pane = MagicMock()
+        orch.tmux_manager.get_session.return_value = mock_session
+
+        orch.executor.execute.return_value = CommandResult(
+            output="Status: OK",
+            completed=True,
+            has_error=False,
+            error_type=None
+        )
+        orch.formatter.format_success.return_value = {"card": "success"}
+
+        # Call a regular command
+        result = orch.handle_message(
+            user_id="user1",
+            message="/gsd:status",
+            channel="test-channel",
+            context={"project": "test-project"}
+        )
+
+        # Verify execute was called with DEFAULT_TIMEOUT (60.0)
+        call_args = orch.executor.execute.call_args
+        assert call_args[1].get('timeout') == 60.0
+
+    def test_handle_message_passes_correct_timeout_based_on_command_type(self, orchestrator_with_mocks):
+        """handle_message should pass correct timeout based on command type."""
+        from gsd_openclaw.tmux_session import TmuxSession
+
+        orch = orchestrator_with_mocks
+
+        mock_session = MagicMock(spec=TmuxSession)
+        mock_session.session_id = "test-123"
+        mock_session.tmux_session = MagicMock()
+        mock_session.tmux_session.active_pane = MagicMock()
+        orch.tmux_manager.get_session.return_value = mock_session
+
+        orch.executor.execute.return_value = CommandResult(
+            output="Output",
+            completed=True,
+            has_error=False,
+            error_type=None
+        )
+        orch.formatter.format_success.return_value = {"card": "success"}
+
+        # Test plan-phase (long command)
+        orch.handle_message(
+            user_id="user1",
+            message="/gsd:plan-phase feature-x",
+            channel="test-channel",
+            context={"project": "test-project"}
+        )
+        call_args = orch.executor.execute.call_args
+        assert call_args[1].get('timeout') is None
+
+        # Reset mock
+        orch.executor.execute.reset_mock()
+
+        # Test discuss-phase (long command)
+        orch.handle_message(
+            user_id="user1",
+            message="/gsd:discuss-phase about architecture",
+            channel="test-channel",
+            context={"project": "test-project"}
+        )
+        call_args = orch.executor.execute.call_args
+        assert call_args[1].get('timeout') is None