diff --git a/src/langbot/pkg/plugin/handler.py b/src/langbot/pkg/plugin/handler.py
index e7029f625..4805f2668 100644
--- a/src/langbot/pkg/plugin/handler.py
+++ b/src/langbot/pkg/plugin/handler.py
@@ -1579,7 +1579,7 @@ class RuntimeConnectionHandler(handler.Handler):
             return await self.call_action(
                 LangBotToRuntimeAction.RECONCILE_PLUGIN_INSTALLATIONS,
                 request.model_dump(),
-                timeout=120,
+                timeout=300,
             )
 
     async def apply_plugin_installation(
diff --git a/tests/unit_tests/plugin/test_handler.py b/tests/unit_tests/plugin/test_handler.py
index c0339d3c4..952d59134 100644
--- a/tests/unit_tests/plugin/test_handler.py
+++ b/tests/unit_tests/plugin/test_handler.py
@@ -9,8 +9,8 @@ from types import SimpleNamespace
 from unittest.mock import AsyncMock, MagicMock, Mock
 import pytest
 
-from langbot_plugin.entities.io.actions.enums import PluginToRuntimeAction
-from langbot_plugin.entities.io.context import ActionContext, InstallationBinding
+from langbot_plugin.entities.io.actions.enums import LangBotToRuntimeAction, PluginToRuntimeAction
+from langbot_plugin.entities.io.context import ActionContext, InstallationBinding, PluginInstallationDesiredState
 
 
 def make_handler(app):
@@ -67,6 +67,20 @@ def make_handler(app):
     return runtime_handler
 
 
+@pytest.mark.asyncio
+async def test_reconcile_plugin_installations_allows_cloud_cold_start_to_finish():
+    app = SimpleNamespace()
+    runtime_handler = make_handler(app)
+    runtime_handler.call_action = AsyncMock(return_value={})
+    binding = next(iter(runtime_handler._installation_bindings.values()))[0]
+    desired = PluginInstallationDesiredState(binding=binding, enabled=True)
+
+    await runtime_handler.reconcile_plugin_installations((desired,))
+
+    assert runtime_handler.call_action.await_args.args[0] == LangBotToRuntimeAction.RECONCILE_PLUGIN_INSTALLATIONS
+    assert runtime_handler.call_action.await_args.kwargs['timeout'] == 300
+
+
 class TestHandlerQueryVariables:
     """Tests for handler query variable logic."""