diff --git a/openhands/server/config/server_config.py b/openhands/server/config/server_config.py
index ae86d8d43a..63bd7a4f28 100644
--- a/openhands/server/config/server_config.py
+++ b/openhands/server/config/server_config.py
@@ -17,6 +17,7 @@ class ServerConfig(ServerConfigInterface):
         'openhands.storage.conversation.file_conversation_store.FileConversationStore'
     )
     conversation_manager_class: str = 'openhands.server.conversation_manager.standalone_conversation_manager.StandaloneConversationManager'
+    monitoring_listener_class: str = 'openhands.server.monitoring.MonitoringListener'
 
     def verify_config(self):
         if self.config_cls:
diff --git a/openhands/server/conversation_manager/standalone_conversation_manager.py b/openhands/server/conversation_manager/standalone_conversation_manager.py
index 2f49de63dc..7440342f36 100644
--- a/openhands/server/conversation_manager/standalone_conversation_manager.py
+++ b/openhands/server/conversation_manager/standalone_conversation_manager.py
@@ -11,6 +11,7 @@ from openhands.core.logger import openhands_logger as logger
 from openhands.core.schema.agent import AgentState
 from openhands.events.action import MessageAction
 from openhands.events.stream import EventStream, session_exists
+from openhands.server.monitoring import MonitoringListener
 from openhands.server.session.conversation import Conversation
 from openhands.server.session.session import ROOM_KEY, Session
 from openhands.server.settings import Settings
@@ -31,6 +32,8 @@ class StandaloneConversationManager(ConversationManager):
     sio: socketio.AsyncServer
     config: AppConfig
     file_store: FileStore
+    # Defaulting monitoring_listener for temp backward compatibility.
+    monitoring_listener: MonitoringListener = MonitoringListener()
     _local_agent_loops_by_sid: dict[str, Session] = field(default_factory=dict)
     _local_connection_id_to_session_id: dict[str, str] = field(default_factory=dict)
     _active_conversations: dict[str, tuple[Conversation, int]] = field(
@@ -208,6 +211,7 @@ class StandaloneConversationManager(ConversationManager):
                 config=self.config,
                 sio=self.sio,
                 user_id=user_id,
+                monitoring_listener=self.monitoring_listener,
             )
             self._local_agent_loops_by_sid[sid] = session
             asyncio.create_task(session.initialize_agent(settings, initial_user_msg))
@@ -280,5 +284,8 @@ class StandaloneConversationManager(ConversationManager):
         sio: socketio.AsyncServer,
         config: AppConfig,
         file_store: FileStore,
+        monitoring_listener: MonitoringListener | None = None,
     ) -> ConversationManager:
-        return StandaloneConversationManager(sio, config, file_store)
+        return StandaloneConversationManager(
+            sio, config, file_store, monitoring_listener or MonitoringListener()
+        )
diff --git a/openhands/server/monitoring.py b/openhands/server/monitoring.py
new file mode 100644
index 0000000000..e5c4462880
--- /dev/null
+++ b/openhands/server/monitoring.py
@@ -0,0 +1,38 @@
+from openhands.core.config.app_config import AppConfig
+from openhands.events.event import Event
+
+
+class MonitoringListener:
+    """
+    Allow tracking of application activity for monitoring purposes.
+
+    Implementations should be non-disruptive, do not raise or block to perform I/O.
+    """
+
+    def on_session_event(self, event: Event) -> None:
+        """
+        Track metrics about events being added to a Session's EventStream.
+        """
+        pass
+
+    def on_agent_session_start(self, success: bool, duration: float) -> None:
+        """
+        Track an agent session start.
+        Success is true if startup completed without error.
+        Duration is start time in seconds observed by AgentSession.
+        """
+        pass
+
+    def on_create_conversation(self) -> None:
+        """
+        Track the beginning of conversation creation.
+        Does not currently capture whether it succeed.
+        """
+        pass
+
+    @classmethod
+    def get_instance(
+        cls,
+        config: AppConfig,
+    ) -> 'MonitoringListener':
+        return cls()
diff --git a/openhands/server/routes/manage_conversations.py b/openhands/server/routes/manage_conversations.py
index 4ef130e49e..88efc03cbf 100644
--- a/openhands/server/routes/manage_conversations.py
+++ b/openhands/server/routes/manage_conversations.py
@@ -18,6 +18,7 @@ from openhands.server.shared import (
     SettingsStoreImpl,
     config,
     conversation_manager,
+    monitoring_listener,
 )
 from openhands.server.types import LLMAuthenticationError, MissingSettingsError
 from openhands.storage.data_models.conversation_info import ConversationInfo
@@ -51,6 +52,7 @@ async def _create_new_conversation(
     initial_user_msg: str | None,
     image_urls: list[str] | None,
 ):
+    monitoring_listener.on_create_conversation()
     logger.info('Loading settings')
     settings_store = await SettingsStoreImpl.get_instance(config, user_id)
     settings = await settings_store.load()
diff --git a/openhands/server/session/agent_session.py b/openhands/server/session/agent_session.py
index 3da21eb0d2..2f71f8e62e 100644
--- a/openhands/server/session/agent_session.py
+++ b/openhands/server/session/agent_session.py
@@ -19,6 +19,7 @@ from openhands.runtime import get_runtime_cls
 from openhands.runtime.base import Runtime
 from openhands.runtime.impl.remote.remote_runtime import RemoteRuntime
 from openhands.security import SecurityAnalyzer, options
+from openhands.server.monitoring import MonitoringListener
 from openhands.storage.files import FileStore
 from openhands.utils.async_utils import call_sync_from_async
 from openhands.utils.shutdown_listener import should_continue
@@ -44,11 +45,13 @@ class AgentSession:
     _started_at: float = 0
     _closed: bool = False
     loop: asyncio.AbstractEventLoop | None = None
+    monitoring_listener: MonitoringListener
 
     def __init__(
         self,
         sid: str,
         file_store: FileStore,
+        monitoring_listener: MonitoringListener,
         status_callback: Optional[Callable] = None,
         github_user_id: str | None = None,
     ):
@@ -64,6 +67,7 @@ class AgentSession:
         self.file_store = file_store
         self._status_callback = status_callback
         self.github_user_id = github_user_id
+        self._monitoring_listener = monitoring_listener
 
     async def start(
         self,
@@ -98,10 +102,13 @@ class AgentSession:
             logger.warning('Session closed before starting')
             return
         self._starting = True
-        self._started_at = time.time()
+        started_at = time.time()
+        self._started_at = started_at
+        finished = False  # For monitoring
+        runtime_connected = False
         try:
             self._create_security_analyzer(config.security.security_analyzer)
-            await self._create_runtime(
+            runtime_connected = await self._create_runtime(
                 runtime_name=runtime_name,
                 config=config,
                 agent=agent,
@@ -134,8 +141,13 @@ class AgentSession:
                     ChangeAgentStateAction(AgentState.AWAITING_USER_INPUT),
                     EventSource.ENVIRONMENT,
                 )
+            finished = True
         finally:
             self._starting = False
+            success = finished and runtime_connected
+            self._monitoring_listener.on_agent_session_start(
+                success, (time.time() - started_at)
+            )
 
     async def close(self):
         """Closes the Agent session"""
@@ -188,13 +200,16 @@ class AgentSession:
         github_token: SecretStr | None = None,
         selected_repository: str | None = None,
         selected_branch: str | None = None,
-    ):
+    ) -> bool:
         """Creates a runtime instance
 
         Parameters:
         - runtime_name: The name of the runtime associated with the session
         - config:
         - agent:
+
+        Return True on successfully connected, False if could not connect.
+        Raises if already created, possibly in other situations.
         """
 
         if self.runtime is not None:
@@ -239,7 +254,7 @@ class AgentSession:
                 self._status_callback(
                     'error', 'STATUS$ERROR_RUNTIME_DISCONNECTED', str(e)
                 )
-            return
+            return False
 
         repo_directory = None
         if selected_repository:
@@ -264,6 +279,7 @@ class AgentSession:
         logger.debug(
             f'Runtime initialized with plugins: {[plugin.name for plugin in self.runtime.plugins]}'
         )
+        return True
 
     def _create_controller(
         self,
diff --git a/openhands/server/session/session.py b/openhands/server/session/session.py
index d7807fc947..1fa99f59f7 100644
--- a/openhands/server/session/session.py
+++ b/openhands/server/session/session.py
@@ -23,6 +23,7 @@ from openhands.events.observation.error import ErrorObservation
 from openhands.events.serialization import event_from_dict, event_to_dict
 from openhands.events.stream import EventStreamSubscriber
 from openhands.llm.llm import LLM
+from openhands.server.monitoring import MonitoringListener
 from openhands.server.session.agent_session import AgentSession
 from openhands.server.session.conversation_init_data import ConversationInitData
 from openhands.server.settings import Settings
@@ -40,6 +41,7 @@ class Session:
     loop: asyncio.AbstractEventLoop
     config: AppConfig
     file_store: FileStore
+    monitoring_listener: MonitoringListener
     user_id: str | None
 
     def __init__(
@@ -47,6 +49,7 @@ class Session:
         sid: str,
         config: AppConfig,
         file_store: FileStore,
+        monitoring_listener: MonitoringListener,
         sio: socketio.AsyncServer | None,
         user_id: str | None = None,
     ):
@@ -59,10 +62,12 @@ class Session:
             file_store,
             status_callback=self.queue_status_message,
             github_user_id=user_id,
+            monitoring_listener=monitoring_listener,
         )
         self.agent_session.event_stream.subscribe(
             EventStreamSubscriber.SERVER, self.on_event, self.sid
         )
+        self.monitoring_listener = monitoring_listener
         # Copying this means that when we update variables they are not applied to the shared global configuration!
         self.config = deepcopy(config)
         self.loop = asyncio.get_event_loop()
@@ -87,7 +92,6 @@ class Session:
             AgentStateChangedObservation('', AgentState.LOADING),
             EventSource.ENVIRONMENT,
         )
-
         agent_cls = settings.agent or self.config.default_agent
         self.config.security.confirmation_mode = (
             self.config.security.confirmation_mode
@@ -175,6 +179,7 @@ class Session:
         Args:
             event: The agent event (Observation or Action).
         """
+        self.monitoring_listener.on_session_event(event)
         if isinstance(event, NullAction):
             return
         if isinstance(event, NullObservation):
diff --git a/openhands/server/shared.py b/openhands/server/shared.py
index 269f42ffd5..2a472e4121 100644
--- a/openhands/server/shared.py
+++ b/openhands/server/shared.py
@@ -1,3 +1,4 @@
+import inspect
 import os
 
 import socketio
@@ -8,6 +9,7 @@ from openhands.server.config.server_config import load_server_config
 from openhands.server.conversation_manager.conversation_manager import (
     ConversationManager,
 )
+from openhands.server.monitoring import MonitoringListener
 from openhands.storage import get_file_store
 from openhands.storage.conversation.conversation_store import ConversationStore
 from openhands.storage.settings.settings_store import SettingsStore
@@ -32,11 +34,27 @@ sio = socketio.AsyncServer(
     async_mode='asgi', cors_allowed_origins='*', client_manager=client_manager
 )
 
+MonitoringListenerImpl = get_impl(
+    MonitoringListener,
+    server_config.monitoring_listener_class,
+)
+
+monitoring_listener = MonitoringListenerImpl.get_instance(config)
+
 ConversationManagerImpl = get_impl(
     ConversationManager,  # type: ignore
     server_config.conversation_manager_class,
 )
-conversation_manager = ConversationManagerImpl.get_instance(sio, config, file_store)
+
+if len(inspect.signature(ConversationManagerImpl.get_instance).parameters) == 3:
+    # This conditional prevents a breaking change in February 2025.
+    # It should be safe to remove by April.
+    conversation_manager = ConversationManagerImpl.get_instance(sio, config, file_store)
+else:
+    # This is the new signature.
+    conversation_manager = ConversationManagerImpl.get_instance(  # type: ignore
+        sio, config, file_store, monitoring_listener
+    )
 
 SettingsStoreImpl = get_impl(SettingsStore, server_config.settings_store_class)  # type: ignore
 
diff --git a/tests/unit/test_agent_session.py b/tests/unit/test_agent_session.py
index fdbe3d0a02..a9a15cd083 100644
--- a/tests/unit/test_agent_session.py
+++ b/tests/unit/test_agent_session.py
@@ -10,6 +10,7 @@ from openhands.events import EventStream, EventStreamSubscriber
 from openhands.llm import LLM
 from openhands.llm.metrics import Metrics
 from openhands.runtime.base import Runtime
+from openhands.server.monitoring import MonitoringListener
 from openhands.server.session.agent_session import AgentSession
 from openhands.storage.memory import InMemoryFileStore
 
@@ -44,7 +45,11 @@ async def test_agent_session_start_with_no_state(mock_agent):
 
     # Setup
     file_store = InMemoryFileStore({})
-    session = AgentSession(sid='test-session', file_store=file_store)
+    session = AgentSession(
+        sid='test-session',
+        file_store=file_store,
+        monitoring_listener=MonitoringListener(),
+    )
 
     # Create a mock runtime and set it up
     mock_runtime = MagicMock(spec=Runtime)
@@ -52,6 +57,7 @@ async def test_agent_session_start_with_no_state(mock_agent):
     # Mock the runtime creation to set up the runtime attribute
     async def mock_create_runtime(*args, **kwargs):
         session.runtime = mock_runtime
+        return True
 
     session._create_runtime = AsyncMock(side_effect=mock_create_runtime)
 
@@ -114,7 +120,11 @@ async def test_agent_session_start_with_restored_state(mock_agent):
 
     # Setup
     file_store = InMemoryFileStore({})
-    session = AgentSession(sid='test-session', file_store=file_store)
+    session = AgentSession(
+        sid='test-session',
+        file_store=file_store,
+        monitoring_listener=MonitoringListener(),
+    )
 
     # Create a mock runtime and set it up
     mock_runtime = MagicMock(spec=Runtime)
@@ -122,6 +132,7 @@ async def test_agent_session_start_with_restored_state(mock_agent):
     # Mock the runtime creation to set up the runtime attribute
     async def mock_create_runtime(*args, **kwargs):
         session.runtime = mock_runtime
+        return True
 
     session._create_runtime = AsyncMock(side_effect=mock_create_runtime)
 
diff --git a/tests/unit/test_session.py b/tests/unit/test_session.py
index 7f61e66f01..d2709e9242 100644
--- a/tests/unit/test_session.py
+++ b/tests/unit/test_session.py
@@ -7,6 +7,7 @@ from litellm.exceptions import (
 
 from openhands.core.config.app_config import AppConfig
 from openhands.core.config.llm_config import LLMConfig
+from openhands.server.monitoring import MonitoringListener
 from openhands.server.session.session import Session
 from openhands.storage.memory import InMemoryFileStore
 
@@ -45,6 +46,7 @@ async def test_notify_on_llm_retry(
         config=config,
         sio=mock_sio,
         user_id='..uid..',
+        monitoring_listener=MonitoringListener(),
     )
     session.queue_status_message = AsyncMock()
 
diff --git a/tests/unit/test_standalone_conversation_manager.py b/tests/unit/test_standalone_conversation_manager.py
index 61ea379831..2e49768aed 100644
--- a/tests/unit/test_standalone_conversation_manager.py
+++ b/tests/unit/test_standalone_conversation_manager.py
@@ -9,6 +9,7 @@ from openhands.core.config.app_config import AppConfig
 from openhands.server.conversation_manager.standalone_conversation_manager import (
     StandaloneConversationManager,
 )
+from openhands.server.monitoring import MonitoringListener
 from openhands.server.session.conversation_init_data import ConversationInitData
 from openhands.storage.memory import InMemoryFileStore
 
@@ -54,7 +55,7 @@ async def test_init_new_local_session():
         ),
     ):
         async with StandaloneConversationManager(
-            sio, AppConfig(), InMemoryFileStore()
+            sio, AppConfig(), InMemoryFileStore(), MonitoringListener()
         ) as conversation_manager:
             await conversation_manager.maybe_start_agent_loop(
                 'new-session-id', ConversationInitData(), 1
@@ -86,7 +87,7 @@ async def test_join_local_session():
         ),
     ):
         async with StandaloneConversationManager(
-            sio, AppConfig(), InMemoryFileStore()
+            sio, AppConfig(), InMemoryFileStore(), MonitoringListener()
         ) as conversation_manager:
             await conversation_manager.maybe_start_agent_loop(
                 'new-session-id', ConversationInitData(), None
@@ -121,7 +122,7 @@ async def test_add_to_local_event_stream():
         ),
     ):
         async with StandaloneConversationManager(
-            sio, AppConfig(), InMemoryFileStore()
+            sio, AppConfig(), InMemoryFileStore(), MonitoringListener()
         ) as conversation_manager:
             await conversation_manager.maybe_start_agent_loop(
                 'new-session-id', ConversationInitData(), 1
@@ -139,7 +140,7 @@ async def test_add_to_local_event_stream():
 async def test_cleanup_session_connections():
     sio = get_mock_sio()
     async with StandaloneConversationManager(
-        sio, AppConfig(), InMemoryFileStore()
+        sio, AppConfig(), InMemoryFileStore(), MonitoringListener()
     ) as conversation_manager:
         conversation_manager._local_connection_id_to_session_id.update(
             {