diff --git a/openhands/server/session/agent_session.py b/openhands/server/session/agent_session.py
index 5f1d1fa9f6..b2d47ba520 100644
--- a/openhands/server/session/agent_session.py
+++ b/openhands/server/session/agent_session.py
@@ -121,11 +121,10 @@ class AgentSession:
         self._started_at = started_at
         finished = False  # For monitoring
         runtime_connected = False
-
+        restored_state = False
         custom_secrets_handler = UserSecrets(
             custom_secrets=custom_secrets if custom_secrets else {}
         )
-
         try:
             self._create_security_analyzer(config.security.security_analyzer)
             runtime_connected = await self._create_runtime(
@@ -173,7 +172,7 @@ class AgentSession:
                     agent_configs,
                 )
             else:
-                self.controller = self._create_controller(
+                self.controller, restored_state = self._create_controller(
                     agent,
                     config.security.confirmation_mode,
                     max_iterations,
@@ -198,14 +197,24 @@ class AgentSession:
         finally:
             self._starting = False
             success = finished and runtime_connected
-            self.logger.info(
-                'Agent session start',
-                extra={
-                    'signal': 'agent_session_start',
-                    'success': success,
-                    'duration': (time.time() - started_at),
-                },
-            )
+            duration = (time.time() - started_at)
+
+            log_metadata = {
+                'signal': 'agent_session_start',
+                'success': success,
+                'duration': duration,
+                'restored_state': restored_state
+            }
+            if success:
+                self.logger.info(
+                    f'Agent session start succeeded in {duration}s',
+                    extra=log_metadata
+                )
+            else:
+                self.logger.error(
+                    f'Agent session start failed in {duration}s',
+                    extra=log_metadata
+                )
 
     async def close(self) -> None:
         """Closes the Agent session"""
@@ -252,7 +261,7 @@ class AgentSession:
         """
         assert initial_message is None
         replay_events = ReplayManager.get_replay_events(json.loads(replay_json))
-        self.controller = self._create_controller(
+        self.controller, _ = self._create_controller(
             agent,
             config.security.confirmation_mode,
             max_iterations,
@@ -396,7 +405,7 @@ class AgentSession:
         agent_to_llm_config: dict[str, LLMConfig] | None = None,
         agent_configs: dict[str, AgentConfig] | None = None,
         replay_events: list[Event] | None = None,
-    ) -> AgentController:
+    ) -> tuple[AgentController, bool]:
         """Creates an AgentController instance
 
         Parameters:
@@ -406,6 +415,9 @@ class AgentSession:
         - max_budget_per_task:
         - agent_to_llm_config:
         - agent_configs:
+
+        Returns:
+            Agent Controller and a bool indicating if state was restored from a previous conversation
         """
 
         if self.controller is not None:
@@ -425,7 +437,7 @@ class AgentSession:
             '-------------------------------------------------------------------------------------------'
         )
         self.logger.debug(msg)
-
+        initial_state = self._maybe_restore_state()
         controller = AgentController(
             sid=self.sid,
             event_stream=self.event_stream,
@@ -437,11 +449,11 @@ class AgentSession:
             confirmation_mode=confirmation_mode,
             headless_mode=False,
             status_callback=self._status_callback,
-            initial_state=self._maybe_restore_state(),
+            initial_state=initial_state,
             replay_events=replay_events,
         )
 
-        return controller
+        return (controller, initial_state is not None)
 
     async def _create_memory(
         self,
diff --git a/openhands/server/session/session.py b/openhands/server/session/session.py
index b468873f8a..76f58c012c 100644
--- a/openhands/server/session/session.py
+++ b/openhands/server/session/session.py
@@ -270,8 +270,8 @@ class Session:
                 isinstance(event, AgentStateChangedObservation)
                 and event.agent_state == AgentState.ERROR
             ):
-                self.logger.info(
-                    'Agent status error',
+                self.logger.error(
+                    f'Agent status error: {event.reason}',
                     extra={'signal': 'agent_status_error'},
                 )
         elif isinstance(event, ErrorObservation):
@@ -329,8 +329,8 @@ class Session:
             controller = self.agent_session.controller
             if controller is not None and not agent_session.is_closed():
                 await controller.set_agent_state_to(AgentState.ERROR)
-            self.logger.info(
-                'Agent status error',
+            self.logger.error(
+                f'Agent status error: {message}',
                 extra={'signal': 'agent_status_error'},
             )
         await self.send(