diff --git a/agent/memory_manager.py b/agent/memory_manager.py
index dcd50a2997a..c4baf44fe9a 100644
--- a/agent/memory_manager.py
+++ b/agent/memory_manager.py
@@ -721,9 +721,10 @@ class MemoryManager:
             try:
                 provider.on_session_end(messages)
             except Exception as e:
-                logger.debug(
+                logger.warning(
                     "Memory provider '%s' on_session_end failed: %s",
                     provider.name, e,
+                    exc_info=True,
                 )
 
     def on_session_switch(
diff --git a/cli.py b/cli.py
index 49da337dfd8..794bf65763f 100644
--- a/cli.py
+++ b/cli.py
@@ -1031,11 +1031,20 @@ def _run_cleanup(*, notify_session_finalize: bool = True):
             # partially-initialised agents where the attribute is missing.
             _session_msgs = getattr(_active_agent_ref, '_session_messages', None)
             if isinstance(_session_msgs, list):
+                logger.info(
+                    "CLI cleanup calling memory shutdown for session %s with %d message(s)",
+                    getattr(_active_agent_ref, "session_id", None) or "<unknown>",
+                    len(_session_msgs),
+                )
                 _active_agent_ref.shutdown_memory_provider(_session_msgs)
             else:
+                logger.info(
+                    "CLI cleanup calling memory shutdown for session %s without session message list",
+                    getattr(_active_agent_ref, "session_id", None) or "<unknown>",
+                )
                 _active_agent_ref.shutdown_memory_provider()
-    except Exception:
-        pass
+    except Exception as e:
+        logger.warning("CLI cleanup memory shutdown failed: %s", e, exc_info=True)
 
 
 def _should_emit_cleanup_session_finalize(session_id: str | None) -> bool:
diff --git a/run_agent.py b/run_agent.py
index 167d11c5ced..2c78123829c 100644
--- a/run_agent.py
+++ b/run_agent.py
@@ -3034,8 +3034,8 @@ class AIAgent:
         if self._memory_manager:
             try:
                 self._memory_manager.on_session_end(messages or [])
-            except Exception:
-                pass
+            except Exception as e:
+                logger.warning("Memory provider on_session_end failed during shutdown: %s", e, exc_info=True)
             try:
                 self._memory_manager.shutdown_all()
             except Exception: