diff --git a/tools/session_search_tool.py b/tools/session_search_tool.py
index 299286d9..a78de895 100644
--- a/tools/session_search_tool.py
+++ b/tools/session_search_tool.py
@@ -20,7 +20,7 @@ import concurrent.futures
 import json
 import os
 import logging
-from typing import Dict, Any, List, Optional
+from typing import Dict, Any, List, Optional, Union
 
 from openai import AsyncOpenAI, OpenAI
 
@@ -46,8 +46,16 @@ MAX_SESSION_CHARS = 100_000
 MAX_SUMMARY_TOKENS = 2000
 
 
-def _format_timestamp(ts) -> str:
-    """Convert a Unix timestamp (float/int) or ISO string to a human-readable date."""
+def _format_timestamp(ts: Optional[Any]) -> str:
+    """
+    Convert a Unix timestamp (float/int) or ISO string to a human-readable date.
+    
+    Args:
+        ts: Unix timestamp (int/float), ISO string, or None
+        
+    Returns:
+        Human-readable date string or "unknown" if conversion fails
+    """
     if ts is None:
         return "unknown"
     try:
@@ -61,8 +69,11 @@ def _format_timestamp(ts) -> str:
                 dt = datetime.fromtimestamp(float(ts))
                 return dt.strftime("%B %d, %Y at %I:%M %p")
             return ts
-    except Exception:
-        pass
+    except (ValueError, OSError, OverflowError) as e:
+        # Log specific errors for debugging while gracefully handling edge cases
+        logging.debug("Failed to format timestamp %s: %s", ts, e)
+    except Exception as e:
+        logging.debug("Unexpected error formatting timestamp %s: %s", ts, e)
     return str(ts)
 
 
@@ -236,18 +247,31 @@ def session_search(
 
         # Resolve child sessions to their parent — delegation stores detailed
         # content in child sessions, but the user's conversation is the parent.
-        def _resolve_to_parent(session_id):
+        def _resolve_to_parent(session_id: str) -> Optional[str]:
+            """
+            Resolve a session ID to its parent session ID, handling delegation chains.
+            
+            Args:
+                session_id: The session ID to resolve
+                
+            Returns:
+                Parent session ID or None if resolution fails
+            """
             visited = set()
             sid = session_id
             while sid and sid not in visited:
                 visited.add(sid)
-                session = db.get_session(sid)
-                if not session:
-                    break
-                parent = session.get("parent_session_id")
-                if parent:
-                    sid = parent
-                else:
+                try:
+                    session = db.get_session(sid)
+                    if not session:
+                        break
+                    parent = session.get("parent_session_id")
+                    if parent:
+                        sid = parent
+                    else:
+                        break
+                except Exception as e:
+                    logging.debug("Error resolving parent for session %s: %s", sid, e)
                     break
             return sid
 
@@ -278,7 +302,8 @@ def session_search(
                 logging.warning(f"Failed to prepare session {session_id}: {e}")
 
         # Summarize all sessions in parallel
-        async def _summarize_all():
+        async def _summarize_all() -> List[Union[str, Exception]]:
+            """Summarize all sessions in parallel."""
             coros = [
                 _summarize_session(text, query, meta)
                 for _, _, text, meta in tasks
@@ -290,7 +315,14 @@ def session_search(
             with concurrent.futures.ThreadPoolExecutor(max_workers=1) as pool:
                 results = pool.submit(lambda: asyncio.run(_summarize_all())).result(timeout=60)
         except RuntimeError:
+            # No event loop running, create a new one
             results = asyncio.run(_summarize_all())
+        except concurrent.futures.TimeoutError:
+            logging.warning("Session summarization timed out after 60 seconds")
+            return json.dumps({
+                "success": False,
+                "error": "Session summarization timed out. Try a more specific query or reduce the limit.",
+            }, ensure_ascii=False)
 
         summaries = []
         for (session_id, match_info, _, _), result in zip(tasks, results):