diff --git a/cli.py b/cli.py
index 9e82e03d3..5e256f275 100644
--- a/cli.py
+++ b/cli.py
@@ -1186,8 +1186,8 @@ class HermesCLI:
         try:
             from hermes_state import SessionDB
             self._session_db = SessionDB()
-        except Exception:
-            pass
+        except Exception as e:
+            logger.warning("Failed to initialize SessionDB — session will NOT be indexed for search: %s", e)
         
         # Deferred title: stored in memory until the session is created in the DB
         self._pending_title: Optional[str] = None
@@ -1852,7 +1852,7 @@ class HermesCLI:
                 from hermes_state import SessionDB
                 self._session_db = SessionDB()
             except Exception as e:
-                logger.debug("SQLite session store not available: %s", e)
+                logger.warning("SQLite session store not available — session will NOT be indexed: %s", e)
         
         # If resuming, validate the session exists and load its history.
         # _preload_resumed_session() may have already loaded it (called from
diff --git a/run_agent.py b/run_agent.py
index 80c5fe3e9..6c0262ccf 100644
--- a/run_agent.py
+++ b/run_agent.py
@@ -887,7 +887,8 @@ class AIAgent:
                     user_id=None,
                 )
             except Exception as e:
-                logger.debug("Session DB create_session failed: %s", e)
+                logger.warning("Session DB create_session failed — messages will NOT be indexed: %s", e)
+                self._session_db = None  # prevent silent data loss on every subsequent flush
         
         # In-memory todo list for task planning (one per agent/session)
         from tools.todo_tool import TodoStore
@@ -1546,7 +1547,7 @@ class AIAgent:
                 )
             self._last_flushed_db_idx = len(messages)
         except Exception as e:
-            logger.debug("Session DB append_message failed: %s", e)
+            logger.warning("Session DB append_message failed: %s", e)
 
     def _get_messages_up_to_last_assistant(self, messages: List[Dict]) -> List[Dict]:
         """
@@ -4687,7 +4688,7 @@ class AIAgent:
                 # Reset flush cursor — new session starts with no messages written
                 self._last_flushed_db_idx = 0
             except Exception as e:
-                logger.debug("Session DB compression split failed: %s", e)
+                logger.warning("Session DB compression split failed — new session will NOT be indexed: %s", e)
 
         # Reset context pressure warning and token estimate — usage drops
         # after compaction.  Without this, the stale last_prompt_tokens from