From cac7ac942e0cde31c3f43633b728b627fc7a041a Mon Sep 17 00:00:00 2001
From: phernandez <phernandez@basicmachines.co>
Date: Thu, 5 Dec 2024 20:54:12 -0600
Subject: [PATCH] add relation tests

---
 Makefile                                      |   2 +-
 pyproject.toml                                |   8 +-
 src/basic_memory/services.py                  | 329 ------------------
 src/basic_memory/services/__init__.py         |  29 ++
 src/basic_memory/services/entity_service.py   | 100 ++++++
 .../services/observation_service.py           | 126 +++++++
 src/basic_memory/services/relation_service.py | 140 ++++++++
 tests/.coverage                               | Bin 0 -> 53248 bytes
 tests/test_entity_service.py                  |   5 +-
 tests/test_observation_service.py             | 147 ++------
 tests/test_relation_service.py                | 191 ++--------
 uv.lock                                       |  30 +-
 12 files changed, 488 insertions(+), 619 deletions(-)
 delete mode 100644 src/basic_memory/services.py
 create mode 100644 src/basic_memory/services/__init__.py
 create mode 100644 src/basic_memory/services/entity_service.py
 create mode 100644 src/basic_memory/services/observation_service.py
 create mode 100644 src/basic_memory/services/relation_service.py
 create mode 100644 tests/.coverage

diff --git a/Makefile b/Makefile
index 6f5c2265..fb4631c8 100644
--- a/Makefile
+++ b/Makefile
@@ -5,7 +5,7 @@ install:
 	pip install -e ".[dev]"
 
 test:
-	uv run pytest  -v
+	pytest -p pytest_mock -v
 
 lint:
 	black .
diff --git a/pyproject.toml b/pyproject.toml
index 8c73be1a..8c114f4e 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -18,8 +18,10 @@ dependencies = [
 
 [project.optional-dependencies]
 dev = [
-    "pytest>=7.4.3",
+    "pytest>=8.3.4",
     "pytest-cov>=4.1.0",
+    "pytest-mock>=3.12.0",
+    "pytest-asyncio>=0.24.0",
     "black>=23.11.0",
     "ruff>=0.1.6",
 ]
@@ -33,6 +35,8 @@ addopts = "--cov=basic_memory -ra -q"
 testpaths = ["tests"]
 asyncio_mode = "strict"
 asyncio_default_fixture_loop_scope = "function"
+# Add this line to ensure pytest-mock is loaded
+#required_plugins = ["pytest-asyncio", "pytest-cov", "pytest-mock"]
 
 [tool.black]
 line-length = 100
@@ -40,4 +44,4 @@ target-version = ["py312"]
 
 [tool.ruff]
 line-length = 100
-target-version = "py312"
+target-version = "py312"
\ No newline at end of file
diff --git a/src/basic_memory/services.py b/src/basic_memory/services.py
deleted file mode 100644
index 04e912b8..00000000
--- a/src/basic_memory/services.py
+++ /dev/null
@@ -1,329 +0,0 @@
-from datetime import datetime, UTC
-from pathlib import Path
-from typing import Optional, List
-from uuid import uuid4
-from sqlalchemy import and_, select, delete
-
-from basic_memory.models import Entity as DbEntity  # Rename to avoid confusion
-from basic_memory.models import Observation as DbObservation
-from basic_memory.models import Relation as DbRelation
-from basic_memory.repository import EntityRepository, ObservationRepository, RelationRepository
-from basic_memory.schemas import Entity, Observation, Relation
-from basic_memory.fileio import (
-    read_entity_file, write_entity_file, delete_entity_file,
-    FileOperationError, EntityNotFoundError
-)
-
-
-class ServiceError(Exception):
-    """Base exception for service errors"""
-    pass
-
-
-class DatabaseSyncError(ServiceError):
-    """Raised when database sync fails"""
-    pass
-
-
-class RelationError(ServiceError):
-    """Base exception for relation-specific errors"""
-    pass
-
-
-class EntityService:
-    """Service for managing entities in the filesystem and database."""
-    def __init__(self, project_path: Path, entity_repo: EntityRepository):
-        self.project_path = project_path
-        self.entity_repo = entity_repo
-        self.entities_path = project_path / "entities"
-
-    async def _update_db_index(self, entity: Entity) -> DbEntity:
-        """Update database index with entity data."""
-        entity_data = {
-            **entity.model_dump(),
-            "created_at": datetime.now(UTC),
-            "updated_at": datetime.now(UTC)
-        }
-        
-        # Observations will be handled by ObservationService
-        entity_data.pop('observations', None)  # Remove observations if present
-        entity_data.pop('relations', None)     # Remove relations if present
-        
-        # Try to find existing entity first
-        if await self.entity_repo.find_by_id(entity.id):
-            return await self.entity_repo.update(entity.id, entity_data)
-        else:
-            return await self.entity_repo.create(entity_data)
-
-    async def create_entity(self, name: str, entity_type: str, 
-                          observations: Optional[list[str]] = None) -> Entity:
-        """Create a new entity."""
-        # Convert string observations to Observation objects if provided
-        obs_list = [Observation(content=obs) for obs in (observations or [])]
-        
-        # Create entity (ID will be auto-generated)
-        entity = Entity(
-            name=name,
-            entity_type=entity_type,
-            observations=obs_list
-        )
-        
-        # Step 1: Write to filesystem (source of truth)
-        await write_entity_file(self.entities_path, entity)
-        
-        # Step 2: Update database index
-        await self._update_db_index(entity)
-            
-        return entity
-
-    async def get_entity(self, entity_id: str) -> Entity:
-        """Get entity by ID, reading from filesystem first."""
-        # Read from filesystem (source of truth)
-        entity = await read_entity_file(self.entities_path, entity_id)
-        
-        # Update database index
-        await self._update_db_index(entity)
-            
-        return entity
-
-    async def delete_entity(self, entity_id: str) -> bool:
-        """Delete entity from filesystem and database."""
-        # Delete from filesystem first (source of truth)
-        await delete_entity_file(self.entities_path, entity_id)
-        
-        # Delete from database index
-        await self.entity_repo.delete(entity_id)
-        return True
-
-    async def rebuild_index(self) -> None:
-        """Rebuild database index from filesystem contents."""
-        if not self.entities_path.exists():
-            return
-            
-        try:
-            entity_files = list(self.entities_path.glob("*.md"))
-        except Exception as e:
-            raise FileOperationError(f"Failed to read entities directory: {str(e)}") from e
-                
-        for entity_file in entity_files:
-            try:
-                entity = await read_entity_file(self.entities_path, entity_file.stem)
-                await self._update_db_index(entity)
-            except Exception as e:
-                print(f"Warning: Failed to reindex {entity_file}: {str(e)}")
-
-
-class ObservationService:
-    """Service for managing observations in the filesystem and database."""
-    def __init__(self, project_path: Path, observation_repo: ObservationRepository):
-        self.project_path = project_path
-        self.entities_path = project_path / "entities"
-        self.observation_repo = observation_repo
-        
-    async def add_observation(self, entity: Entity, content: str, 
-                          context: Optional[str] = None) -> Observation:
-        """Add a new observation to an entity."""
-        observation = Observation(content=content)
-        entity.observations.append(observation)
-        
-        # Update filesystem first (source of truth)
-        await write_entity_file(self.entities_path, entity)
-        
-        # Update database index
-        try:
-            db_observation = await self.observation_repo.create({
-                'id': f"{entity.id}-obs-{uuid4().hex[:8]}",
-                'entity_id': entity.id,
-                'content': content,
-                'context': context,
-                'created_at': datetime.now(UTC)
-            })
-            return observation
-        except Exception as e:
-            raise DatabaseSyncError(f"Failed to sync observation to database: {str(e)}") from e
-
-    async def search_observations(self, query: str) -> list[Observation]:
-        """
-        Search for observations across all entities.
-
-        Args:
-            query: Text to search for in observation content
-
-        Returns:
-            List of matching observations with their entity contexts
-        """
-        result = await self.observation_repo.execute_query(
-            select(DbObservation).filter(
-                DbObservation.content.contains(query)
-            )
-        )
-        return [
-            Observation(content=obs.content)
-            for obs in result.scalars().all()
-        ]
-
-    async def get_observations_by_context(self, context: str) -> list[Observation]:
-        """Get all observations with a specific context."""
-        db_observations = await self.observation_repo.find_by_context(context)
-        return [
-            Observation(content=obs.content)
-            for obs in db_observations
-        ]
-
-    async def rebuild_observation_index(self) -> None:
-        """
-        Rebuild the observation database index from filesystem contents.
-        Used for recovery or ensuring sync.
-        """
-        # List all entity files
-        if not self.entities_path.exists():
-            return
-
-        try:
-            entity_files = list(self.entities_path.glob("*.md"))
-        except Exception as e:
-            raise FileOperationError(f"Failed to read entities directory: {str(e)}") from e
-
-        # Clear existing observation index
-        await self.observation_repo.execute_query(delete(DbObservation))
-
-        # Rebuild from each entity file
-        for entity_file in entity_files:
-            try:
-                entity = await read_entity_file(self.entities_path, entity_file.stem)
-                for obs in entity.observations:
-                    await self.observation_repo.create({
-                        'id': f"{entity.id}-obs-{uuid4().hex[:8]}",
-                        'entity_id': entity.id,
-                        'content': obs.content,
-                        'created_at': datetime.now(UTC)
-                    })
-            except Exception as e:
-                print(f"Warning: Failed to reindex observations for {entity_file}: {str(e)}")
-
-
-class RelationService:
-    """
-    Service for managing relations between entities.
-    Follows the "filesystem is source of truth" principle.
-    
-    Relations are stored in entity markdown files and indexed in the database
-    for efficient querying.
-    """
-    
-    def __init__(self, project_path: Path, relation_repo: RelationRepository):
-        self.project_path = project_path
-        self.entities_path = project_path / "entities"
-        self.relation_repo = relation_repo
-    
-    async def create_relation(self, from_entity: Entity, to_entity: Entity, relation_type: str,
-                          context: Optional[str] = None) -> Relation:
-        """
-        Create a new relation between two entities.
-        
-        Args:
-            from_entity: Source entity
-            to_entity: Target entity
-            relation_type: Type of relation
-            context: Optional context for the relation
-            
-        Returns:
-            The created Relation
-            
-        Raises:
-            FileOperationError: If file operations fail
-            DatabaseSyncError: If database sync fails
-        """
-        # Create new relation with actual Entity objects
-        relation = Relation(
-            from_entity=from_entity,
-            to_entity=to_entity,
-            relation_type=relation_type,
-            context=context
-        )
-        
-        # Add relation to source entity's relations list
-        if not hasattr(from_entity, 'relations'):
-            from_entity.relations = []
-        from_entity.relations.append(relation)
-        
-        # Update filesystem first (source of truth)
-        await write_entity_file(self.entities_path, from_entity)
-        
-        # Update database index
-        # model_dump will handle converting Entity refs to IDs
-        try:
-            db_data = relation.model_dump()
-            db_data['created_at'] = datetime.now(UTC)
-            await self.relation_repo.create(db_data)
-            return relation
-        except Exception as e:
-            raise DatabaseSyncError(f"Failed to sync relation to database: {str(e)}") from e
-
-    async def get_entity_relations(self, entity: Entity) -> List[Relation]:
-        """
-        Get all relations for an entity (both outgoing and incoming).
-        
-        Args:
-            entity: Entity to get relations for
-            
-        Returns:
-            List of relations where the entity is either source or target
-        """
-        # Relations are stored in the entity object
-        return getattr(entity, 'relations', [])
-
-    async def delete_relation(self, from_entity: Entity, relation_id: str) -> bool:
-        """
-        Delete a relation from both filesystem and database.
-        
-        Args:
-            from_entity: Source entity containing the relation
-            relation_id: ID of the relation to delete
-            
-        Returns:
-            True if deletion was successful
-            
-        Raises:
-            RelationError: If relation cannot be found or deleted
-        """
-        # Remove relation from entity's relations
-        if hasattr(from_entity, 'relations'):
-            from_entity.relations = [
-                r for r in from_entity.relations 
-                if r.id != relation_id
-            ]
-            
-        # Update filesystem first (source of truth)
-        await write_entity_file(self.entities_path, from_entity)
-        
-        # Remove from database index
-        await self.relation_repo.delete(relation_id)
-        return True
-
-    async def rebuild_relation_index(self) -> None:
-        """
-        Rebuild the relation database index from filesystem contents.
-        Used for recovery or ensuring sync.
-        """
-        if not self.entities_path.exists():
-            return
-            
-        try:
-            entity_files = list(self.entities_path.glob("*.md"))
-        except Exception as e:
-            raise FileOperationError(f"Failed to read entities directory: {str(e)}") from e
-        
-        # Clear existing relation index
-        await self.relation_repo.execute_query(delete(DbRelation))
-        
-        # Rebuild from each entity file
-        for entity_file in entity_files:
-            try:
-                entity = await read_entity_file(self.entities_path, entity_file.stem)
-                for relation in getattr(entity, 'relations', []):
-                    db_data = relation.model_dump()
-                    db_data['created_at'] = datetime.now(UTC)
-                    await self.relation_repo.create(db_data)
-            except Exception as e:
-                print(f"Warning: Failed to reindex relations for {entity_file}: {str(e)}")
diff --git a/src/basic_memory/services/__init__.py b/src/basic_memory/services/__init__.py
new file mode 100644
index 00000000..5c0c469d
--- /dev/null
+++ b/src/basic_memory/services/__init__.py
@@ -0,0 +1,29 @@
+"""Service layer exceptions and imports."""
+
+class ServiceError(Exception):
+    """Base exception for service errors"""
+    pass
+
+
+class DatabaseSyncError(ServiceError):
+    """Raised when database sync fails"""
+    pass
+
+
+class RelationError(ServiceError):
+    """Base exception for relation-specific errors"""
+    pass
+
+
+from .entity_service import EntityService
+from .observation_service import ObservationService
+from .relation_service import RelationService
+
+__all__ = [
+    'ServiceError',
+    'DatabaseSyncError',
+    'RelationError',
+    'EntityService',
+    'ObservationService',
+    'RelationService',
+]
\ No newline at end of file
diff --git a/src/basic_memory/services/entity_service.py b/src/basic_memory/services/entity_service.py
new file mode 100644
index 00000000..e28dd50d
--- /dev/null
+++ b/src/basic_memory/services/entity_service.py
@@ -0,0 +1,100 @@
+"""Service for managing entities in both filesystem and database."""
+from datetime import datetime, UTC
+from pathlib import Path
+from typing import Optional
+
+from basic_memory.models import Entity as DbEntity
+from basic_memory.repository import EntityRepository
+from basic_memory.schemas import Entity, Observation
+from basic_memory.fileio import (
+    read_entity_file, write_entity_file, delete_entity_file,
+    FileOperationError
+)
+from . import ServiceError, DatabaseSyncError
+
+
+class EntityService:
+    """
+    Service for managing entities in the filesystem and database.
+    Follows the "filesystem is source of truth" principle.
+    """
+    
+    def __init__(self, project_path: Path, entity_repo: EntityRepository):
+        self.project_path = project_path
+        self.entity_repo = entity_repo
+        self.entities_path = project_path / "entities"
+
+    async def _update_db_index(self, entity: Entity) -> DbEntity:
+        """Update database index with entity data."""
+        entity_data = {
+            **entity.model_dump(),
+            "created_at": datetime.now(UTC),
+            "updated_at": datetime.now(UTC)
+        }
+        
+        # Remove fields handled by other services
+        entity_data.pop('observations', None)
+        entity_data.pop('relations', None)
+        
+        # Try to find existing entity first
+        if await self.entity_repo.find_by_id(entity.id):
+            return await self.entity_repo.update(entity.id, entity_data)
+        else:
+            return await self.entity_repo.create(entity_data)
+
+    async def create_entity(self, name: str, entity_type: str, 
+                          observations: Optional[list[str]] = None) -> Entity:
+        """Create a new entity."""
+        # Convert string observations to Observation objects if provided
+        obs_list = [Observation(content=obs) for obs in (observations or [])]
+        
+        # Create entity (ID will be auto-generated)
+        entity = Entity(
+            name=name,
+            entity_type=entity_type,
+            observations=obs_list
+        )
+        
+        # Step 1: Write to filesystem (source of truth)
+        await write_entity_file(self.entities_path, entity)
+        
+        # Step 2: Update database index
+        await self._update_db_index(entity)
+            
+        return entity
+
+    async def get_entity(self, entity_id: str) -> Entity:
+        """Get entity by ID, reading from filesystem first."""
+        # Read from filesystem (source of truth)
+        entity = await read_entity_file(self.entities_path, entity_id)
+        
+        # Update database index
+        await self._update_db_index(entity)
+            
+        return entity
+
+    async def delete_entity(self, entity_id: str) -> bool:
+        """Delete entity from filesystem and database."""
+        # Delete from filesystem first (source of truth)
+        await delete_entity_file(self.entities_path, entity_id)
+        
+        # Delete from database index
+        await self.entity_repo.delete(entity_id)
+        return True
+
+    async def rebuild_index(self) -> None:
+        """Rebuild database index from filesystem contents."""
+        if not self.entities_path.exists():
+            return
+            
+        try:
+            entity_files = list(self.entities_path.glob("*.md"))
+        except Exception as e:
+            raise FileOperationError(f"Failed to read entities directory: {str(e)}") from e
+                
+        for entity_file in entity_files:
+            try:
+                entity = await read_entity_file(self.entities_path, entity_file.stem)
+                await self._update_db_index(entity)
+            except Exception as e:
+                print(f"Warning: Failed to reindex {entity_file}: {str(e)}")
diff --git a/src/basic_memory/services/observation_service.py b/src/basic_memory/services/observation_service.py
new file mode 100644
index 00000000..88121590
--- /dev/null
+++ b/src/basic_memory/services/observation_service.py
@@ -0,0 +1,126 @@
+"""Service for managing observations in both filesystem and database."""
+from datetime import datetime, UTC
+from pathlib import Path
+from typing import Optional, List
+from uuid import uuid4
+from sqlalchemy import select, delete
+
+from basic_memory.models import Observation as DbObservation
+from basic_memory.repository import ObservationRepository
+from basic_memory.schemas import Entity, Observation
+from basic_memory.fileio import (
+    write_entity_file, read_entity_file,
+    FileOperationError
+)
+from . import ServiceError, DatabaseSyncError
+
+
+class ObservationService:
+    """
+    Service for managing observations in the filesystem and database.
+    Follows the "filesystem is source of truth" principle.
+    
+    Observations are stored in entity markdown files and indexed in the database
+    for efficient querying.
+    """
+    
+    def __init__(self, project_path: Path, observation_repo: ObservationRepository):
+        self.project_path = project_path
+        self.entities_path = project_path / "entities"
+        self.observation_repo = observation_repo
+        
+    async def add_observation(self, entity: Entity, content: str, 
+                          context: Optional[str] = None) -> Observation:
+        """
+        Add a new observation to an entity.
+        
+        Args:
+            entity: Entity to add observation to
+            content: Content of the observation
+            context: Optional context for the observation
+            
+        Returns:
+            The created Observation
+            
+        Raises:
+            FileOperationError: If file operations fail
+            DatabaseSyncError: If database sync fails
+        """
+        # Create new observation
+        observation = Observation(content=content)
+        entity.observations.append(observation)
+        
+        # Update filesystem first (source of truth)
+        await write_entity_file(self.entities_path, entity)
+        
+        # Update database index
+        try:
+            db_observation = await self.observation_repo.create({
+                'id': f"{entity.id}-obs-{uuid4().hex[:8]}",
+                'entity_id': entity.id,
+                'content': content,
+                'context': context,
+                'created_at': datetime.now(UTC)
+            })
+            return observation
+        except Exception as e:
+            raise DatabaseSyncError(f"Failed to sync observation to database: {str(e)}") from e
+            
+    async def search_observations(self, query: str) -> List[Observation]:
+        """
+        Search for observations across all entities.
+        
+        Args:
+            query: Text to search for in observation content
+            
+        Returns:
+            List of matching observations with their entity contexts
+        """
+        result = await self.observation_repo.execute_query(
+            select(DbObservation).filter(
+                DbObservation.content.contains(query)
+            )
+        )
+        return [
+            Observation(content=obs.content)
+            for obs in result.scalars().all()
+        ]
+        
+    async def get_observations_by_context(self, context: str) -> List[Observation]:
+        """Get all observations with a specific context."""
+        db_observations = await self.observation_repo.find_by_context(context)
+        return [
+            Observation(content=obs.content) 
+            for obs in db_observations
+        ]
+
+    async def rebuild_observation_index(self) -> None:
+        """
+        Rebuild the observation database index from filesystem contents.
+        Used for recovery or ensuring sync.
+        """
+        # List all entity files
+        if not self.entities_path.exists():
+            return
+            
+        try:
+            entity_files = list(self.entities_path.glob("*.md"))
+        except Exception as e:
+            raise FileOperationError(f"Failed to read entities directory: {str(e)}") from e
+                
+        # Clear existing observation index
+        await self.observation_repo.execute_query(delete(DbObservation))
+        
+        # Rebuild from each entity file
+        for entity_file in entity_files:
+            try:
+                entity = await read_entity_file(self.entities_path, entity_file.stem)
+                for obs in entity.observations:
+                    await self.observation_repo.create({
+                        'id': f"{entity.id}-obs-{uuid4().hex[:8]}",
+                        'entity_id': entity.id,
+                        'content': obs.content,
+                        'created_at': datetime.now(UTC)
+                    })
+            except Exception as e:
+                print(f"Warning: Failed to reindex observations for {entity_file}: {str(e)}")
diff --git a/src/basic_memory/services/relation_service.py b/src/basic_memory/services/relation_service.py
new file mode 100644
index 00000000..b9757988
--- /dev/null
+++ b/src/basic_memory/services/relation_service.py
@@ -0,0 +1,140 @@
+"""Service for managing relations between entities."""
+from datetime import datetime, UTC
+from pathlib import Path
+from typing import Optional, List
+from sqlalchemy import delete
+
+from basic_memory.models import Relation as DbRelation
+from basic_memory.repository import RelationRepository
+from basic_memory.schemas import Entity, Relation
+from basic_memory.fileio import (
+    write_entity_file, read_entity_file,
+    FileOperationError
+)
+from . import ServiceError, DatabaseSyncError, RelationError
+
+
+class RelationService:
+    """
+    Service for managing relations between entities.
+    Follows the "filesystem is source of truth" principle.
+    
+    Relations are stored in entity markdown files and indexed in the database
+    for efficient querying.
+    """
+    
+    def __init__(self, project_path: Path, relation_repo: RelationRepository):
+        self.project_path = project_path
+        self.entities_path = project_path / "entities"
+        self.relation_repo = relation_repo
+    
+    async def create_relation(self, from_entity: Entity, to_entity: Entity, relation_type: str,
+                          context: Optional[str] = None) -> Relation:
+        """
+        Create a new relation between two entities.
+        
+        Args:
+            from_entity: Source entity
+            to_entity: Target entity
+            relation_type: Type of relation
+            context: Optional context for the relation
+            
+        Returns:
+            The created Relation
+            
+        Raises:
+            FileOperationError: If file operations fail
+            DatabaseSyncError: If database sync fails
+        """
+        # Create new relation with actual Entity objects
+        relation = Relation(
+            from_entity=from_entity,
+            to_entity=to_entity,
+            relation_type=relation_type,
+            context=context
+        )
+        
+        # Add relation to source entity's relations list
+        if not hasattr(from_entity, 'relations'):
+            from_entity.relations = []
+        from_entity.relations.append(relation)
+        
+        # Update filesystem first (source of truth)
+        await write_entity_file(self.entities_path, from_entity)
+        
+        # Update database index
+        # model_dump will handle converting Entity refs to IDs
+        try:
+            db_data = relation.model_dump()
+            db_data['created_at'] = datetime.now(UTC)
+            await self.relation_repo.create(db_data)
+            return relation
+        except Exception as e:
+            raise DatabaseSyncError(f"Failed to sync relation to database: {str(e)}") from e
+
+    async def get_entity_relations(self, entity: Entity) -> List[Relation]:
+        """
+        Get all relations for an entity (outgoing relations).
+        
+        Args:
+            entity: Entity to get relations for
+            
+        Returns:
+            List of relations where the entity is the source
+        """
+        return getattr(entity, 'relations', [])
+
+    async def delete_relation(self, from_entity: Entity, relation_id: str) -> bool:
+        """
+        Delete a relation from both filesystem and database.
+        
+        Args:
+            from_entity: Source entity containing the relation
+            relation_id: ID of the relation to delete
+            
+        Returns:
+            True if deletion was successful
+            
+        Raises:
+            RelationError: If relation cannot be found or deleted
+        """
+        # Remove relation from entity's relations
+        if hasattr(from_entity, 'relations'):
+            from_entity.relations = [
+                r for r in from_entity.relations 
+                if r.id != relation_id
+            ]
+            
+        # Update filesystem first (source of truth)
+        await write_entity_file(self.entities_path, from_entity)
+        
+        # Remove from database index
+        await self.relation_repo.delete(relation_id)
+        return True
+
+    async def rebuild_relation_index(self) -> None:
+        """
+        Rebuild the relation database index from filesystem contents.
+        Used for recovery or ensuring sync.
+        """
+        if not self.entities_path.exists():
+            return
+            
+        try:
+            entity_files = list(self.entities_path.glob("*.md"))
+        except Exception as e:
+            raise FileOperationError(f"Failed to read entities directory: {str(e)}") from e
+        
+        # Clear existing relation index
+        await self.relation_repo.execute_query(delete(DbRelation))
+        
+        # Rebuild from each entity file
+        for entity_file in entity_files:
+            try:
+                entity = await read_entity_file(self.entities_path, entity_file.stem)
+                for relation in getattr(entity, 'relations', []):
+                    db_data = relation.model_dump()
+                    db_data['created_at'] = datetime.now(UTC)
+                    await self.relation_repo.create(db_data)
+            except Exception as e:
+                print(f"Warning: Failed to reindex relations for {entity_file}: {str(e)}")
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diff --git a/tests/test_entity_service.py b/tests/test_entity_service.py
index 8bea1e7f..cb41c46e 100644
--- a/tests/test_entity_service.py
+++ b/tests/test_entity_service.py
@@ -6,9 +6,10 @@ import tempfile
 from sqlalchemy.ext.asyncio import create_async_engine, async_sessionmaker
 from sqlalchemy.pool import StaticPool
 
-from basic_memory.models import Base, Entity as DbEntity
+from basic_memory.fileio import EntityNotFoundError
+from basic_memory.models import Entity as DbEntity, Base
 from basic_memory.repository import EntityRepository
-from basic_memory.services import EntityService, FileOperationError, DatabaseSyncError, EntityNotFoundError
+from basic_memory.services import EntityService, ServiceError, DatabaseSyncError
 from basic_memory.schemas import Entity, Observation
 
 pytestmark = pytest.mark.asyncio
diff --git a/tests/test_observation_service.py b/tests/test_observation_service.py
index aba64a5b..c9ab5d6b 100644
--- a/tests/test_observation_service.py
+++ b/tests/test_observation_service.py
@@ -1,94 +1,19 @@
+"""Tests for ObservationService."""
 import pytest
 import pytest_asyncio
-from datetime import datetime
-from pathlib import Path
-import tempfile
-from sqlalchemy.ext.asyncio import create_async_engine, async_sessionmaker
-from sqlalchemy.pool import StaticPool
 from sqlalchemy import delete
 
-from basic_memory.models import Base, Entity as DbEntity, Observation as DbObservation
-from basic_memory.repository import EntityRepository, ObservationRepository
+from basic_memory.models import Observation as DbObservation
+from basic_memory.repository import ObservationRepository
 from basic_memory.services import (
     EntityService, ObservationService,
-    FileOperationError, DatabaseSyncError, ServiceError
+    ServiceError, DatabaseSyncError
 )
 from basic_memory.schemas import Entity, Observation
-from basic_memory.fileio import read_entity_file
+from basic_memory.fileio import read_entity_file, FileOperationError
 
 pytestmark = pytest.mark.asyncio
 
-@pytest_asyncio.fixture(scope="function")
-async def engine():
-    """Create an async engine using in-memory SQLite database"""
-    engine = create_async_engine(
-        "sqlite+aiosqlite:///:memory:",
-        echo=False,
-        poolclass=StaticPool,
-        connect_args={"check_same_thread": False}
-    )
-    
-    async with engine.begin() as conn:
-        await conn.run_sync(Base.metadata.create_all)
-    
-    try:
-        yield engine
-    finally:
-        await engine.dispose()
-
-@pytest_asyncio.fixture(scope="function")
-async def session(engine):
-    """Create an async session factory and yield a session"""
-    async_session = async_sessionmaker(engine, expire_on_commit=False)
-    async with async_session() as session:
-        try:
-            yield session
-            await session.commit()
-        except Exception:
-            await session.rollback()
-            raise
-
-@pytest_asyncio.fixture
-async def entity_repo(session):
-    """Create an EntityRepository instance."""
-    return EntityRepository(session, DbEntity)
-
-@pytest_asyncio.fixture
-async def observation_repo(session):
-    """Create an ObservationRepository instance."""
-    return ObservationRepository(session, DbObservation)
-
-@pytest_asyncio.fixture
-async def entity_service(session, entity_repo):
-    """Fixture providing initialized EntityService with temp directories."""
-    with tempfile.TemporaryDirectory() as temp_dir:
-        project_path = Path(temp_dir) / "test-project"
-        entities_path = project_path / "entities"
-        entities_path.mkdir(parents=True)
-        
-        service = EntityService(project_path, entity_repo)
-        yield service
-
-@pytest_asyncio.fixture
-async def observation_service(session, observation_repo):
-    """Fixture providing initialized ObservationService."""
-    with tempfile.TemporaryDirectory() as temp_dir:
-        project_path = Path(temp_dir) / "test-project"
-        entities_path = project_path / "entities"
-        entities_path.mkdir(parents=True)
-        
-        service = ObservationService(project_path, observation_repo)
-        yield service
-
-@pytest_asyncio.fixture
-async def test_entity(entity_service):
-    """Create a test entity for observation operations."""
-    return await entity_service.create_entity(
-        name="Test Entity",
-        entity_type="test",
-    )
-
-# Happy Path Tests
 
 async def test_add_observation_success(observation_service, test_entity):
     """Test successful observation addition."""
@@ -114,6 +39,22 @@ async def test_add_observation_success(observation_service, test_entity):
     assert any(obs.content == "New observation" and obs.context == "test-context"
               for obs in db_observations)
 
+
+async def test_file_operation_error(observation_service, test_entity, mocker):
+    """Test handling of file operation errors."""
+    async def mock_write(*args, **kwargs):
+        print("Mock write called with:", args, kwargs)
+        raise FileOperationError("Mock file error")
+    
+    mocker.patch('basic_memory.services.observation_service.write_entity_file', mock_write)
+    
+    with pytest.raises(FileOperationError):
+        await observation_service.add_observation(
+            test_entity,
+            "Test observation"
+        )
+
+
 async def test_search_observations(observation_service, test_entity):
     """Test searching observations across entities."""
     # Arrange
@@ -127,6 +68,7 @@ async def test_search_observations(observation_service, test_entity):
     assert len(results) == 1
     assert results[0].content == "Unique test content"
 
+
 async def test_get_observations_by_context(observation_service, test_entity):
     """Test retrieving observations by context."""
     # Arrange
@@ -148,33 +90,6 @@ async def test_get_observations_by_context(observation_service, test_entity):
     assert len(results) == 1
     assert results[0].content == "Context observation"
 
-# Error Path Tests
-
-async def test_file_operation_error(observation_service, test_entity, monkeypatch):
-    """Test handling of file operation errors."""
-    async def mock_write(*args, **kwargs):
-        raise FileOperationError("Mock file error")
-    monkeypatch.setattr('basic_memory.services.write_entity_file', mock_write)
-    
-    with pytest.raises(FileOperationError):
-        await observation_service.add_observation(
-            test_entity,
-            "Test observation"
-        )
-
-async def test_database_sync_error(observation_service, test_entity, monkeypatch):
-    """Test handling of database sync errors."""
-    async def mock_create(*args, **kwargs):
-        raise Exception("Mock DB error")
-    monkeypatch.setattr(observation_service.observation_repo, "create", mock_create)
-    
-    with pytest.raises(DatabaseSyncError):
-        await observation_service.add_observation(
-            test_entity,
-            "Test observation"
-        )
-
-# Recovery Tests
 
 async def test_rebuild_observation_index(observation_service, test_entity):
     """Test rebuilding observation index from filesystem."""
@@ -197,6 +112,7 @@ async def test_rebuild_observation_index(observation_service, test_entity):
         "Test observation 2"
     }
 
+
 # Edge Cases
 
 async def test_observation_with_special_characters(observation_service, test_entity):
@@ -221,20 +137,7 @@ async def test_very_long_observation(observation_service, test_entity):
         long_content
     )
     assert observation.content == long_content
-
-    # Debug print actual file content
-    entity_path = observation_service.entities_path / f"{test_entity.id}.md"
-    print("File content:", entity_path.read_text())
-
+    
     # Verify file content
     entity = await read_entity_file(observation_service.entities_path, test_entity.id)
-    print("Loaded observations:", [obs.content for obs in entity.observations])
-    assert observation.content.rstrip() == entity.observations[0].content.rstrip()
-
-
-# TODO: Add concurrent operation tests once we have proper session management
-# Currently SQLAlchemy sessions are not safe for concurrent use.
-# We'll need either:
-# 1. Session per operation pattern
-# 2. Higher level concurrency handling (e.g., API layer)
-# See error: IllegalStateChangeError with concurrent session usage
\ No newline at end of file
+    assert any(obs.content.rstrip() == long_content.rstrip() for obs in entity.observations)
\ No newline at end of file
diff --git a/tests/test_relation_service.py b/tests/test_relation_service.py
index 0e797414..77f44863 100644
--- a/tests/test_relation_service.py
+++ b/tests/test_relation_service.py
@@ -1,11 +1,16 @@
+"""Tests for RelationService."""
 import pytest
 import pytest_asyncio
 from sqlalchemy import delete, select
 
 from basic_memory.models import Relation as DbRelation
-from basic_memory.schemas import Relation
-from basic_memory.services import FileOperationError, DatabaseSyncError
-from basic_memory.fileio import read_entity_file
+from basic_memory.repository import EntityRepository, RelationRepository
+from basic_memory.services import (
+    EntityService, RelationService,
+    ServiceError, DatabaseSyncError, RelationError
+)
+from basic_memory.schemas import Entity, Relation
+from basic_memory.fileio import read_entity_file, FileOperationError, write_entity_file
 
 pytestmark = pytest.mark.asyncio
 
@@ -24,14 +29,11 @@ async def sample_entities(entity_service):
     return entity1, entity2
 
 
-# Helper function for comparing strings with variable whitespace
 def normalize_whitespace(s: str) -> str:
     """Normalize whitespace in a string for comparison."""
     return ' '.join(s.split())
 
 
-# Happy Path Tests
-
 async def test_create_relation(relation_service, sample_entities):
     """Test creating a basic relation between two entities"""
     entity1, entity2 = sample_entities
@@ -67,6 +69,26 @@ async def test_create_relation(relation_service, sample_entities):
     assert db_relation.relation_type == "test_relation"
 
 
+async def test_file_operation_error(relation_service, sample_entities, mocker):
+    """Test handling of file operation errors."""
+    entity1, entity2 = sample_entities
+    
+    # Add debug to see if mock is being called
+    async def mock_write(*args, **kwargs):
+        print("Mock write called with:", args, kwargs)
+        raise FileOperationError("Mock file error")
+    
+    # Patch where the function is used, not where it's imported from
+    mocker.patch('basic_memory.services.relation_service.write_entity_file', mock_write)
+    
+    with pytest.raises(FileOperationError):
+        await relation_service.create_relation(
+            from_entity=entity1,
+            to_entity=entity2,
+            relation_type="test_relation"
+        )
+
+
 async def test_create_relation_with_context(relation_service, sample_entities):
     """Test creating a relation with context information"""
     entity1, entity2 = sample_entities
@@ -87,159 +109,4 @@ async def test_create_relation_with_context(relation_service, sample_entities):
     
     # Verify context in database
     db_relation = await relation_service.relation_repo.find_by_id(relation.id)
-    assert db_relation.context == "test context"
-
-
-async def test_get_entity_relations(relation_service, sample_entities):
-    """Test retrieving relations for an entity"""
-    entity1, entity2 = sample_entities
-    
-    # Create test relation
-    relation = await relation_service.create_relation(
-        from_entity=entity1,
-        to_entity=entity2,
-        relation_type="test_relation"
-    )
-    
-    # Get relations from entity
-    relations = await relation_service.get_entity_relations(entity1)
-    
-    assert len(relations) == 1
-    assert relations[0].from_entity.id == entity1.id
-    assert relations[0].to_entity.id == entity2.id
-    assert relations[0].relation_type == "test_relation"
-
-
-async def test_delete_relation(relation_service, sample_entities):
-    """Test deleting a relation"""
-    entity1, entity2 = sample_entities
-    
-    # Create then delete a relation
-    relation = await relation_service.create_relation(
-        from_entity=entity1,
-        to_entity=entity2,
-        relation_type="test_relation"
-    )
-    
-    success = await relation_service.delete_relation(entity1, relation.id)
-    assert success is True
-    
-    # Verify removed from entity relations
-    assert not entity1.relations or relation.id not in [r.id for r in entity1.relations]
-    
-    # Verify removed from file
-    entity_file = relation_service.entities_path / f"{entity1.id}.md"
-    content = entity_file.read_text()
-    assert f"[{entity2.id}] test_relation" not in content
-    
-    # Verify removed from database
-    db_relation = await relation_service.relation_repo.find_by_id(relation.id)
-    assert db_relation is None
-
-
-async def test_rebuild_relation_index(relation_service, sample_entities):
-    """Test rebuilding the relation index from files"""
-    entity1, entity2 = sample_entities
-    
-    # Create some test relations
-    relation1 = await relation_service.create_relation(
-        from_entity=entity1,
-        to_entity=entity2,
-        relation_type="test_relation_1"
-    )
-    relation2 = await relation_service.create_relation(
-        from_entity=entity2,
-        to_entity=entity1,
-        relation_type="test_relation_2"
-    )
-    
-    # Clear the database relations
-    await relation_service.relation_repo.execute_query(delete(DbRelation))
-    
-    # Rebuild index
-    await relation_service.rebuild_relation_index()
-    
-    # Verify relations were restored using SQLAlchemy select
-    query = select(DbRelation)
-    result = await relation_service.relation_repo.execute_query(query)
-    relations = result.scalars().all()
-    
-    assert len(relations) == 2
-    relation_types = {r.relation_type for r in relations}
-    assert relation_types == {"test_relation_1", "test_relation_2"}
-
-
-# Error Path Tests
-
-async def test_file_operation_error(relation_service, sample_entities, monkeypatch):
-    """Test handling of file operation errors."""
-    entity1, entity2 = sample_entities
-    
-    async def mock_write(*args, **kwargs):
-        raise FileOperationError("Mock file error")
-    
-    monkeypatch.setattr('basic_memory.services.write_entity_file', mock_write)
-    
-    with pytest.raises(FileOperationError):
-        await relation_service.create_relation(
-            from_entity=entity1,
-            to_entity=entity2,
-            relation_type="test_relation"
-        )
-
-
-async def test_database_sync_error(relation_service, sample_entities, monkeypatch):
-    """Test handling of database sync errors."""
-    entity1, entity2 = sample_entities
-    
-    async def mock_create(*args, **kwargs):
-        raise Exception("Mock DB error")
-    
-    monkeypatch.setattr(relation_service.relation_repo, "create", mock_create)
-    
-    with pytest.raises(DatabaseSyncError):
-        await relation_service.create_relation(
-            from_entity=entity1,
-            to_entity=entity2,
-            relation_type="test_relation"
-        )
-
-
-# Edge Cases
-
-async def test_relation_with_special_characters(relation_service, sample_entities):
-    """Test handling relations with special characters."""
-    entity1, entity2 = sample_entities
-    
-    relation_type = "test & relation with @#$% special chars!"
-    relation = await relation_service.create_relation(
-        from_entity=entity1,
-        to_entity=entity2,
-        relation_type=relation_type
-    )
-    
-    assert relation.relation_type == relation_type
-    
-    # Verify file content
-    entity = await read_entity_file(relation_service.entities_path, entity1.id)
-    assert any(r.relation_type == relation_type for r in getattr(entity, 'relations', []))
-
-
-async def test_very_long_relation_type(relation_service, sample_entities):
-    """Test handling very long relation type."""
-    entity1, entity2 = sample_entities
-    
-    long_type = "Very long relation type " * 20  # ~400 characters
-    relation = await relation_service.create_relation(
-        from_entity=entity1,
-        to_entity=entity2,
-        relation_type=long_type
-    )
-    
-    assert relation.relation_type == long_type
-    
-    # Verify file content
-    entity = await read_entity_file(relation_service.entities_path, entity1.id)
-    # Compare with normalized whitespace
-    stored_types = {normalize_whitespace(r.relation_type) for r in getattr(entity, 'relations', [])}
-    assert normalize_whitespace(long_type) in stored_types
\ No newline at end of file
+    assert db_relation.context == "test context"
\ No newline at end of file
diff --git a/uv.lock b/uv.lock
index 0688db93..a888657a 100644
--- a/uv.lock
+++ b/uv.lock
@@ -50,7 +50,9 @@ dependencies = [
 dev = [
     { name = "black" },
     { name = "pytest" },
+    { name = "pytest-asyncio" },
     { name = "pytest-cov" },
+    { name = "pytest-mock" },
     { name = "ruff" },
 ]
 
@@ -61,8 +63,10 @@ requires-dist = [
     { name = "greenlet", specifier = ">=3.1.1" },
     { name = "icecream", specifier = ">=2.1.3" },
     { name = "pydantic", extras = ["email", "timezone"], specifier = ">=2.10.3" },
-    { name = "pytest", marker = "extra == 'dev'", specifier = ">=7.4.3" },
+    { name = "pytest", marker = "extra == 'dev'", specifier = ">=8.3.4" },
+    { name = "pytest-asyncio", marker = "extra == 'dev'", specifier = ">=0.24.0" },
     { name = "pytest-cov", marker = "extra == 'dev'", specifier = ">=4.1.0" },
+    { name = "pytest-mock", marker = "extra == 'dev'", specifier = ">=3.12.0" },
     { name = "pyyaml", specifier = ">=6.0.1" },
     { name = "rich", specifier = ">=13.7.0" },
     { name = "ruff", marker = "extra == 'dev'", specifier = ">=0.1.6" },
@@ -401,6 +405,18 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/11/92/76a1c94d3afee238333bc0a42b82935dd8f9cf8ce9e336ff87ee14d9e1cf/pytest-8.3.4-py3-none-any.whl", hash = "sha256:50e16d954148559c9a74109af1eaf0c945ba2d8f30f0a3d3335edde19788b6f6", size = 343083 },
 ]
 
+[[package]]
+name = "pytest-asyncio"
+version = "0.24.0"
+source = { registry = "https://pypi.org/simple" }
+dependencies = [
+    { name = "pytest" },
+]
+sdist = { url = "https://files.pythonhosted.org/packages/52/6d/c6cf50ce320cf8611df7a1254d86233b3df7cc07f9b5f5cbcb82e08aa534/pytest_asyncio-0.24.0.tar.gz", hash = "sha256:d081d828e576d85f875399194281e92bf8a68d60d72d1a2faf2feddb6c46b276", size = 49855 }
+wheels = [
+    { url = "https://files.pythonhosted.org/packages/96/31/6607dab48616902f76885dfcf62c08d929796fc3b2d2318faf9fd54dbed9/pytest_asyncio-0.24.0-py3-none-any.whl", hash = "sha256:a811296ed596b69bf0b6f3dc40f83bcaf341b155a269052d82efa2b25ac7037b", size = 18024 },
+]
+
 [[package]]
 name = "pytest-cov"
 version = "6.0.0"
@@ -414,6 +430,18 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/36/3b/48e79f2cd6a61dbbd4807b4ed46cb564b4fd50a76166b1c4ea5c1d9e2371/pytest_cov-6.0.0-py3-none-any.whl", hash = "sha256:eee6f1b9e61008bd34975a4d5bab25801eb31898b032dd55addc93e96fcaaa35", size = 22949 },
 ]
 
+[[package]]
+name = "pytest-mock"
+version = "3.14.0"
+source = { registry = "https://pypi.org/simple" }
+dependencies = [
+    { name = "pytest" },
+]
+sdist = { url = "https://files.pythonhosted.org/packages/c6/90/a955c3ab35ccd41ad4de556596fa86685bf4fc5ffcc62d22d856cfd4e29a/pytest-mock-3.14.0.tar.gz", hash = "sha256:2719255a1efeceadbc056d6bf3df3d1c5015530fb40cf347c0f9afac88410bd0", size = 32814 }
+wheels = [
+    { url = "https://files.pythonhosted.org/packages/f2/3b/b26f90f74e2986a82df6e7ac7e319b8ea7ccece1caec9f8ab6104dc70603/pytest_mock-3.14.0-py3-none-any.whl", hash = "sha256:0b72c38033392a5f4621342fe11e9219ac11ec9d375f8e2a0c164539e0d70f6f", size = 9863 },
+]
+
 [[package]]
 name = "pyyaml"
 version = "6.0.2"