diff --git a/src/basic_memory/repository/entity_repository.py b/src/basic_memory/repository/entity_repository.py
index 1159e280..9fbfb72f 100644
--- a/src/basic_memory/repository/entity_repository.py
+++ b/src/basic_memory/repository/entity_repository.py
@@ -8,6 +8,7 @@ from sqlalchemy.exc import IntegrityError
 from sqlalchemy.ext.asyncio import AsyncSession, async_sessionmaker
 from sqlalchemy.orm import selectinload
 from sqlalchemy.orm.interfaces import LoaderOption
+from sqlalchemy.dialects.sqlite import insert as sqlite_insert
 
 from basic_memory import db
 from basic_memory.models.knowledge import Entity, Observation, Relation
@@ -252,3 +253,159 @@ class EntityRepository(Repository[Entity]):
         if not found:  # pragma: no cover
             raise RuntimeError(f"Failed to retrieve entity after insert: {entity.file_path}")
         return found
+
+    async def upsert_entity_optimistic(
+        self, entity_data: dict, conflict_columns: Optional[List[str]] = None
+    ) -> Entity:
+        """Insert or update entity using SQLite's ON CONFLICT clause for optimistic concurrency.
+
+        This method uses SQLite's native ON CONFLICT semantics to handle race conditions
+        efficiently without manual exception handling.
+
+        Args:
+            entity_data: Dictionary of entity data to insert/update
+            conflict_columns: Columns to use for conflict detection (defaults to ['file_path'])
+
+        Returns:
+            The inserted or updated entity
+        """
+        if conflict_columns is None:
+            conflict_columns = ["file_path"]
+
+        async with db.scoped_session(self.session_maker) as session:
+            # Ensure project_id is set
+            if (
+                self.project_id is not None
+                and "project_id" not in entity_data
+                and "project_id" in self.valid_columns
+            ):
+                entity_data["project_id"] = self.project_id
+
+            # Create the upsert statement using SQLite's ON CONFLICT
+            stmt = sqlite_insert(Entity).values(entity_data)
+            stmt = stmt.on_conflict_do_update(
+                index_elements=conflict_columns,
+                set_={
+                    key: stmt.excluded[key]
+                    for key in entity_data.keys()
+                    if key not in conflict_columns and key != "id"
+                },
+            )
+
+            await session.execute(stmt)
+            await session.flush()
+
+            # Retrieve the entity with relationships loaded
+            file_path = entity_data.get("file_path")
+            if not file_path:
+                raise ValueError("file_path is required for upsert_entity_optimistic")
+
+            query = (
+                self.select()
+                .where(Entity.file_path == file_path)
+                .options(*self.get_load_options())
+            )
+            result = await session.execute(query)
+            found = result.scalar_one_or_none()
+
+            if not found:  # pragma: no cover
+                raise RuntimeError(f"Failed to retrieve entity after optimistic upsert: {file_path}")
+
+            return found
+
+    async def update_entity_optimistic(
+        self, file_path: str, updates: dict, conflict_columns: Optional[List[str]] = None
+    ) -> Optional[Entity]:
+        """Update an entity by file_path using SQLite's ON CONFLICT clause.
+
+        This method is designed to replace direct update() calls in sync operations
+        to eliminate race conditions.
+
+        Args:
+            file_path: The file_path of the entity to update
+            updates: Dictionary of fields to update
+            conflict_columns: Columns to use for conflict detection (defaults to ['file_path'])
+
+        Returns:
+            The updated entity or None if no entity exists with the given file_path
+        """
+        if conflict_columns is None:
+            conflict_columns = ["file_path"]
+
+        async with db.scoped_session(self.session_maker) as session:
+            # First check if entity exists
+            existing_entity = await session.execute(
+                select(Entity).where(
+                    Entity.file_path == file_path,
+                    Entity.project_id == self.project_id
+                )
+            )
+            entity = existing_entity.scalar_one_or_none()
+            
+            if not entity:
+                # Entity doesn't exist, cannot update
+                return None
+
+            # Prepare the data for upsert (include the file_path and any other required fields)
+            entity_data = {
+                "file_path": file_path,
+                "project_id": self.project_id,
+                **updates
+            }
+
+            # For updates, we need to include the current values that shouldn't change
+            # This ensures we don't lose data during the upsert
+            for field in ["title", "entity_type", "content_type", "permalink", "checksum", "created_at", "updated_at"]:
+                if field not in entity_data and hasattr(entity, field):
+                    current_value = getattr(entity, field)
+                    if current_value is not None:
+                        entity_data[field] = current_value
+
+            # Use the optimistic upsert method
+            return await self.upsert_entity_optimistic(entity_data, conflict_columns)
+
+    async def update_entity_by_id_optimistic(
+        self, entity_id: int, updates: dict
+    ) -> Optional[Entity]:
+        """Update an entity by ID using current values + updates, then upsert optimistically.
+
+        This method is useful when you have an entity ID and want to update specific fields
+        while preserving all other current values.
+
+        Args:
+            entity_id: The ID of the entity to update
+            updates: Dictionary of fields to update
+
+        Returns:
+            The updated entity or None if no entity exists with the given ID
+        """
+        async with db.scoped_session(self.session_maker) as session:
+            # First get the current entity
+            existing_entity = await session.execute(
+                select(Entity).where(Entity.id == entity_id)
+            )
+            entity = existing_entity.scalar_one_or_none()
+            
+            if not entity:
+                # Entity doesn't exist, cannot update
+                return None
+
+            # Prepare the data for upsert with current values + updates
+            entity_data = {
+                "file_path": entity.file_path,
+                "project_id": entity.project_id,
+                "title": entity.title,
+                "entity_type": entity.entity_type,
+                "content_type": entity.content_type,
+                "permalink": entity.permalink,
+                "checksum": entity.checksum,
+                "created_at": entity.created_at,
+                "updated_at": entity.updated_at,
+                **updates  # Override with new values
+            }
+
+            # For moves, we need to handle the file_path conflict properly
+            conflict_columns = ["file_path"] if "file_path" in updates else ["file_path"]
+
+            # Use the optimistic upsert method
+            return await self.upsert_entity_optimistic(entity_data, conflict_columns)
diff --git a/src/basic_memory/sync/sync_service.py b/src/basic_memory/sync/sync_service.py
index 96e6f792..77bdae7b 100644
--- a/src/basic_memory/sync/sync_service.py
+++ b/src/basic_memory/sync/sync_service.py
@@ -389,8 +389,8 @@ class SyncService:
                         logger.error(f"Entity not found after constraint violation, path={path}")
                         raise ValueError(f"Entity not found after constraint violation: {path}")
 
-                    updated = await self.entity_repository.update(
-                        entity.id, {"file_path": path, "checksum": checksum}
+                    updated = await self.entity_repository.update_entity_optimistic(
+                        path, {"checksum": checksum}
                     )
 
                     if updated is None:  # pragma: no cover
@@ -407,8 +407,8 @@ class SyncService:
                 logger.error(f"Entity not found for existing file, path={path}")
                 raise ValueError(f"Entity not found for existing file: {path}")
 
-            updated = await self.entity_repository.update(
-                entity.id, {"file_path": path, "checksum": checksum}
+            updated = await self.entity_repository.update_entity_optimistic(
+                path, {"checksum": checksum}
             )
 
             if updated is None:  # pragma: no cover
@@ -477,7 +477,7 @@ class SyncService:
                     f"new_checksum={new_checksum}"
                 )
 
-            updated = await self.entity_repository.update(entity.id, updates)
+            updated = await self.entity_repository.update_entity_by_id_optimistic(entity.id, updates)
 
             if updated is None:  # pragma: no cover
                 logger.error(