Merge pull request #771 from MODSetter/dev

chore: various fixes and document ownership tracking

surfsense_backend/alembic/versions/86_add_document_created_by.py

@@ -0,0 +1,185 @@
+"""Add created_by_id column to documents table for document ownership tracking
+
+Revision ID: 86
+Revises: 85
+Create Date: 2026-02-02
+
+Changes:
+1. Add created_by_id column (UUID, nullable, foreign key to user.id)
+2. Create index on created_by_id for performance
+3. Backfill existing documents with search space owner's user_id (with progress indicator)
+"""
+
+import sys
+from collections.abc import Sequence
+
+import sqlalchemy as sa
+
+from alembic import op
+
+# revision identifiers, used by Alembic.
+revision: str = "86"
+down_revision: str | None = "85"
+branch_labels: str | Sequence[str] | None = None
+depends_on: str | Sequence[str] | None = None
+
+# Batch size for backfill operation
+BATCH_SIZE = 5000
+
+
+def upgrade() -> None:
+    """Add created_by_id column to documents and backfill with search space owner."""
+
+    # 1. Add created_by_id column (nullable for backward compatibility)
+    print("Step 1/4: Adding created_by_id column...")
+    op.execute(
+        """
+        DO $$
+        BEGIN
+            IF NOT EXISTS (
+                SELECT 1 FROM information_schema.columns
+                WHERE table_name = 'documents' AND column_name = 'created_by_id'
+            ) THEN
+                ALTER TABLE documents
+                ADD COLUMN created_by_id UUID;
+            END IF;
+        END$$;
+        """
+    )
+    print("  Done: created_by_id column added.")
+
+    # 2. Create index on created_by_id for efficient queries
+    print("Step 2/4: Creating index on created_by_id...")
+    op.execute(
+        """
+        CREATE INDEX IF NOT EXISTS ix_documents_created_by_id
+        ON documents (created_by_id);
+        """
+    )
+    print("  Done: Index created.")
+
+    # 3. Add foreign key constraint with ON DELETE SET NULL
+    # First check if constraint already exists
+    print("Step 3/4: Adding foreign key constraint...")
+    op.execute(
+        """
+        DO $$
+        BEGIN
+            IF NOT EXISTS (
+                SELECT 1 FROM information_schema.table_constraints
+                WHERE constraint_name = 'fk_documents_created_by_id'
+                AND table_name = 'documents'
+            ) THEN
+                ALTER TABLE documents
+                ADD CONSTRAINT fk_documents_created_by_id
+                FOREIGN KEY (created_by_id) REFERENCES "user"(id)
+                ON DELETE SET NULL;
+            END IF;
+        END$$;
+        """
+    )
+    print("  Done: Foreign key constraint added.")
+
+    # 4. Backfill existing documents with search space owner's user_id
+    # Process in batches with progress indicator
+    print("Step 4/4: Backfilling created_by_id for existing documents...")
+    
+    connection = op.get_bind()
+    
+    # Get total count of documents that need backfilling
+    result = connection.execute(
+        sa.text("""
+            SELECT COUNT(*) FROM documents WHERE created_by_id IS NULL
+        """)
+    )
+    total_count = result.scalar()
+    
+    if total_count == 0:
+        print("  No documents need backfilling. Skipping.")
+        return
+    
+    print(f"  Total documents to backfill: {total_count:,}")
+    
+    processed = 0
+    batch_num = 0
+    
+    while processed < total_count:
+        batch_num += 1
+        
+        # Update a batch of documents using a subquery to limit the update
+        # We use ctid (tuple identifier) for efficient batching in PostgreSQL
+        result = connection.execute(
+            sa.text("""
+                UPDATE documents
+                SET created_by_id = searchspaces.user_id
+                FROM searchspaces
+                WHERE documents.search_space_id = searchspaces.id
+                AND documents.created_by_id IS NULL
+                AND documents.id IN (
+                    SELECT d.id FROM documents d
+                    WHERE d.created_by_id IS NULL
+                    LIMIT :batch_size
+                )
+            """),
+            {"batch_size": BATCH_SIZE}
+        )
+        
+        rows_updated = result.rowcount
+        if rows_updated == 0:
+            # No more rows to update
+            break
+            
+        processed += rows_updated
+        progress_pct = min(100.0, (processed / total_count) * 100)
+        
+        # Print progress with carriage return for in-place update
+        sys.stdout.write(f"\r  Progress: {processed:,}/{total_count:,} documents ({progress_pct:.1f}%) - Batch {batch_num}")
+        sys.stdout.flush()
+    
+    # Final newline after progress
+    print()
+    print(f"  Done: Backfilled {processed:,} documents.")
+
+
+def downgrade() -> None:
+    """Remove created_by_id column from documents."""
+
+    # Drop foreign key constraint
+    op.execute(
+        """
+        DO $$
+        BEGIN
+            IF EXISTS (
+                SELECT 1 FROM information_schema.table_constraints
+                WHERE constraint_name = 'fk_documents_created_by_id'
+                AND table_name = 'documents'
+            ) THEN
+                ALTER TABLE documents
+                DROP CONSTRAINT fk_documents_created_by_id;
+            END IF;
+        END$$;
+        """
+    )
+
+    # Drop index
+    op.execute(
+        """
+        DROP INDEX IF EXISTS ix_documents_created_by_id;
+        """
+    )
+
+    # Drop column
+    op.execute(
+        """
+        DO $$
+        BEGIN
+            IF EXISTS (
+                SELECT 1 FROM information_schema.columns
+                WHERE table_name = 'documents' AND column_name = 'created_by_id'
+            ) THEN
+                ALTER TABLE documents
+                DROP COLUMN created_by_id;
+            END IF;
+        END$$;
+        """
+    )

surfsense_backend/alembic/versions/87_add_document_connector_id.py

@@ -0,0 +1,170 @@
+"""Add connector_id column to documents table for linking documents to their source connector
+
+Revision ID: 87
+Revises: 86
+Create Date: 2026-02-02
+
+Changes:
+1. Add connector_id column (Integer, nullable, foreign key to search_source_connectors.id)
+2. Create index on connector_id for efficient bulk deletion queries
+3. SET NULL on delete - allows controlled cleanup in application code
+4. Backfill existing documents based on document_type and search_space_id matching
+"""
+
+from collections.abc import Sequence
+
+from alembic import op
+
+# revision identifiers, used by Alembic.
+revision: str = "87"
+down_revision: str | None = "86"
+branch_labels: str | Sequence[str] | None = None
+depends_on: str | Sequence[str] | None = None
+
+
+def upgrade() -> None:
+    """Add connector_id column to documents and backfill from existing connectors."""
+
+    # 1. Add connector_id column (nullable - for manually uploaded docs without connector)
+    op.execute(
+        """
+        DO $$
+        BEGIN
+            IF NOT EXISTS (
+                SELECT 1 FROM information_schema.columns
+                WHERE table_name = 'documents' AND column_name = 'connector_id'
+            ) THEN
+                ALTER TABLE documents
+                ADD COLUMN connector_id INTEGER;
+            END IF;
+        END$$;
+        """
+    )
+
+    # 2. Create index on connector_id for efficient cleanup queries
+    op.execute(
+        """
+        CREATE INDEX IF NOT EXISTS ix_documents_connector_id
+        ON documents (connector_id);
+        """
+    )
+
+    # 3. Add foreign key constraint with ON DELETE SET NULL
+    # SET NULL allows us to delete documents in controlled batches before deleting connector
+    op.execute(
+        """
+        DO $$
+        BEGIN
+            IF NOT EXISTS (
+                SELECT 1 FROM information_schema.table_constraints
+                WHERE constraint_name = 'fk_documents_connector_id'
+                AND table_name = 'documents'
+            ) THEN
+                ALTER TABLE documents
+                ADD CONSTRAINT fk_documents_connector_id
+                FOREIGN KEY (connector_id) REFERENCES search_source_connectors(id)
+                ON DELETE SET NULL;
+            END IF;
+        END$$;
+        """
+    )
+
+    # 4. Backfill existing documents with connector_id based on document_type matching
+    # This maps document types to their corresponding connector types
+    # Only backfills for documents in search spaces that have exactly one connector of that type
+
+    # Map of document_type -> connector_type for backfilling
+    document_connector_mappings = [
+        ("NOTION_CONNECTOR", "NOTION_CONNECTOR"),
+        ("SLACK_CONNECTOR", "SLACK_CONNECTOR"),
+        ("TEAMS_CONNECTOR", "TEAMS_CONNECTOR"),
+        ("GITHUB_CONNECTOR", "GITHUB_CONNECTOR"),
+        ("LINEAR_CONNECTOR", "LINEAR_CONNECTOR"),
+        ("DISCORD_CONNECTOR", "DISCORD_CONNECTOR"),
+        ("JIRA_CONNECTOR", "JIRA_CONNECTOR"),
+        ("CONFLUENCE_CONNECTOR", "CONFLUENCE_CONNECTOR"),
+        ("CLICKUP_CONNECTOR", "CLICKUP_CONNECTOR"),
+        ("GOOGLE_CALENDAR_CONNECTOR", "GOOGLE_CALENDAR_CONNECTOR"),
+        ("GOOGLE_GMAIL_CONNECTOR", "GOOGLE_GMAIL_CONNECTOR"),
+        ("GOOGLE_DRIVE_FILE", "GOOGLE_DRIVE_CONNECTOR"),
+        ("AIRTABLE_CONNECTOR", "AIRTABLE_CONNECTOR"),
+        ("LUMA_CONNECTOR", "LUMA_CONNECTOR"),
+        ("ELASTICSEARCH_CONNECTOR", "ELASTICSEARCH_CONNECTOR"),
+        ("BOOKSTACK_CONNECTOR", "BOOKSTACK_CONNECTOR"),
+        ("CIRCLEBACK", "CIRCLEBACK_CONNECTOR"),
+        ("OBSIDIAN_CONNECTOR", "OBSIDIAN_CONNECTOR"),
+        ("COMPOSIO_GOOGLE_DRIVE_CONNECTOR", "COMPOSIO_GOOGLE_DRIVE_CONNECTOR"),
+        ("COMPOSIO_GMAIL_CONNECTOR", "COMPOSIO_GMAIL_CONNECTOR"),
+        ("COMPOSIO_GOOGLE_CALENDAR_CONNECTOR", "COMPOSIO_GOOGLE_CALENDAR_CONNECTOR"),
+        ("CRAWLED_URL", "WEBCRAWLER_CONNECTOR"),
+    ]
+
+    for doc_type, connector_type in document_connector_mappings:
+        # Backfill connector_id for documents where:
+        # 1. Document has this document_type
+        # 2. Document doesn't already have a connector_id
+        # 3. There's exactly one connector of this type in the same search space
+        # This safely handles most cases while avoiding ambiguity
+        op.execute(
+            f"""
+            UPDATE documents d
+            SET connector_id = (
+                SELECT ssc.id 
+                FROM search_source_connectors ssc
+                WHERE ssc.search_space_id = d.search_space_id
+                AND ssc.connector_type = '{connector_type}'
+                LIMIT 1
+            )
+            WHERE d.document_type = '{doc_type}'
+            AND d.connector_id IS NULL
+            AND EXISTS (
+                SELECT 1 FROM search_source_connectors ssc
+                WHERE ssc.search_space_id = d.search_space_id
+                AND ssc.connector_type = '{connector_type}'
+            );
+            """
+        )
+
+
+def downgrade() -> None:
+    """Remove connector_id column from documents."""
+
+    # Drop foreign key constraint
+    op.execute(
+        """
+        DO $$
+        BEGIN
+            IF EXISTS (
+                SELECT 1 FROM information_schema.table_constraints
+                WHERE constraint_name = 'fk_documents_connector_id'
+                AND table_name = 'documents'
+            ) THEN
+                ALTER TABLE documents
+                DROP CONSTRAINT fk_documents_connector_id;
+            END IF;
+        END$$;
+        """
+    )
+
+    # Drop index
+    op.execute(
+        """
+        DROP INDEX IF EXISTS ix_documents_connector_id;
+        """
+    )
+
+    # Drop column
+    op.execute(
+        """
+        DO $$
+        BEGIN
+            IF EXISTS (
+                SELECT 1 FROM information_schema.columns
+                WHERE table_name = 'documents' AND column_name = 'connector_id'
+            ) THEN
+                ALTER TABLE documents
+                DROP COLUMN connector_id;
+            END IF;
+        END$$;
+        """
+    )

surfsense_backend/alembic/versions/88_make_podcast_transcript_nullable.py

@@ -0,0 +1,58 @@
+"""Make podcast_transcript nullable
+
+Revision ID: 88
+Revises: 87
+Create Date: 2026-02-02
+
+The podcast workflow now creates a podcast record with PENDING status first,
+then fills in the transcript after generation completes. This requires
+podcast_transcript to be nullable.
+"""
+
+from collections.abc import Sequence
+
+from alembic import op
+
+revision: str = "88"
+down_revision: str | None = "87"
+branch_labels: str | Sequence[str] | None = None
+depends_on: str | Sequence[str] | None = None
+
+
+def upgrade() -> None:
+    # Make podcast_transcript nullable and remove the server default
+    op.execute(
+        """
+        ALTER TABLE podcasts
+        ALTER COLUMN podcast_transcript DROP NOT NULL;
+        """
+    )
+    op.execute(
+        """
+        ALTER TABLE podcasts
+        ALTER COLUMN podcast_transcript DROP DEFAULT;
+        """
+    )
+
+
+def downgrade() -> None:
+    # Set empty JSON for any NULL values before adding NOT NULL constraint
+    op.execute(
+        """
+        UPDATE podcasts
+        SET podcast_transcript = '{}'::jsonb
+        WHERE podcast_transcript IS NULL;
+        """
+    )
+    op.execute(
+        """
+        ALTER TABLE podcasts
+        ALTER COLUMN podcast_transcript SET DEFAULT '{}';
+        """
+    )
+    op.execute(
+        """
+        ALTER TABLE podcasts
+        ALTER COLUMN podcast_transcript SET NOT NULL;
+        """
+    )

surfsense_backend/app/celery_app.py

@@ -81,6 +81,7 @@ celery_app = Celery(
         "app.tasks.celery_tasks.blocknote_migration_tasks",
         "app.tasks.celery_tasks.document_reindex_tasks",
         "app.tasks.celery_tasks.stale_notification_cleanup_task",
+        "app.tasks.celery_tasks.connector_deletion_task",
     ],
 )
 

surfsense_backend/app/connectors/composio_gmail_connector.py

@@ -394,6 +394,8 @@ async def _process_gmail_message_batch(
                 embedding=summary_embedding,
                 chunks=chunks,
                 updated_at=get_current_timestamp(),
+                created_by_id=user_id,
+                connector_id=connector_id,
             )
             session.add(document)
             documents_indexed += 1

surfsense_backend/app/connectors/composio_google_calendar_connector.py

@@ -442,6 +442,8 @@ async def index_composio_google_calendar(
                     embedding=summary_embedding,
                     chunks=chunks,
                     updated_at=get_current_timestamp(),
+                    created_by_id=user_id,
+                    connector_id=connector_id,
                 )
                 session.add(document)
                 documents_indexed += 1

surfsense_backend/app/connectors/composio_google_drive_connector.py

@@ -1248,7 +1248,6 @@ async def _process_single_drive_file(
             "file_name": file_name,
             "FILE_NAME": file_name,  # For compatibility
             "mime_type": mime_type,
-            "connector_id": connector_id,
             "toolkit_id": "googledrive",
             "source": "composio",
         },
@@ -1258,6 +1257,8 @@ async def _process_single_drive_file(
         embedding=summary_embedding,
         chunks=chunks,
         updated_at=get_current_timestamp(),
+        created_by_id=user_id,
+        connector_id=connector_id,
     )
     session.add(document)
 

surfsense_backend/app/connectors/google_drive/content_extractor.py

@@ -25,6 +25,7 @@ async def download_and_process_file(
     session: AsyncSession,
     task_logger: TaskLoggingService,
     log_entry: Log,
+    connector_id: int | None = None,
 ) -> tuple[Any, str | None, dict[str, Any] | None]:
     """
     Download Google Drive file and process using Surfsense file processors.
@@ -37,6 +38,7 @@ async def download_and_process_file(
         session: Database session
         task_logger: Task logging service
         log_entry: Log entry for tracking
+        connector_id: ID of the connector (for de-indexing support)
 
     Returns:
         Tuple of (Document object if successful, error message if failed, file metadata dict)
@@ -92,6 +94,9 @@ async def download_and_process_file(
                 "source_connector": "google_drive",
             },
         }
+        # Include connector_id for de-indexing support
+        if connector_id is not None:
+            connector_info["connector_id"] = connector_id
 
         # Add additional Drive metadata if available
         if "modifiedTime" in file:

surfsense_backend/app/connectors/google_drive/credentials.py

@@ -127,7 +127,12 @@ async def get_valid_credentials(
                     )
                 creds_dict["_token_encrypted"] = True
 
-            connector.config = creds_dict
+            # IMPORTANT: Merge new credentials with existing config to preserve
+            # user settings like selected_folders, selected_files, indexing_options,
+            # folder_tokens, etc. that would otherwise be wiped on token refresh.
+            existing_config = connector.config.copy() if connector.config else {}
+            existing_config.update(creds_dict)
+            connector.config = existing_config
             flag_modified(connector, "config")
             await session.commit()
 

surfsense_backend/app/db.py

@@ -751,7 +751,27 @@ class Document(BaseModel, TimestampMixin):
     search_space_id = Column(
         Integer, ForeignKey("searchspaces.id", ondelete="CASCADE"), nullable=False
     )
+
+    # Track who created/uploaded this document
+    created_by_id = Column(
+        UUID(as_uuid=True),
+        ForeignKey("user.id", ondelete="SET NULL"),
+        nullable=True,  # Nullable for backward compatibility with existing records
+        index=True,
+    )
+
+    # Track which connector created this document (for cleanup on connector deletion)
+    connector_id = Column(
+        Integer,
+        ForeignKey("search_source_connectors.id", ondelete="SET NULL"),
+        nullable=True,  # Nullable for manually uploaded docs without connector
+        index=True,
+    )
+
+    # Relationships
     search_space = relationship("SearchSpace", back_populates="documents")
+    created_by = relationship("User", back_populates="documents")
+    connector = relationship("SearchSourceConnector", back_populates="documents")
     chunks = relationship(
         "Chunk", back_populates="document", cascade="all, delete-orphan"
     )
@@ -980,6 +1000,9 @@ class SearchSourceConnector(BaseModel, TimestampMixin):
         UUID(as_uuid=True), ForeignKey("user.id", ondelete="CASCADE"), nullable=False
     )
 
+    # Documents created by this connector (for cleanup on connector deletion)
+    documents = relationship("Document", back_populates="connector")
+
 
 class NewLLMConfig(BaseModel, TimestampMixin):
     """
@@ -1286,6 +1309,13 @@ if config.AUTH_TYPE == "GOOGLE":
             passive_deletes=True,
         )
 
+        # Documents created/uploaded by this user
+        documents = relationship(
+            "Document",
+            back_populates="created_by",
+            passive_deletes=True,
+        )
+
         # User memories for personalized AI responses
         memories = relationship(
             "UserMemory",
@@ -1344,6 +1374,13 @@ else:
             passive_deletes=True,
         )
 
+        # Documents created/uploaded by this user
+        documents = relationship(
+            "Document",
+            back_populates="created_by",
+            passive_deletes=True,
+        )
+
         # User memories for personalized AI responses
         memories = relationship(
             "UserMemory",

surfsense_backend/app/routes/circleback_webhook_route.py

@@ -9,8 +9,12 @@ import logging
 from datetime import datetime
 from typing import Any
 
-from fastapi import APIRouter, HTTPException
+from fastapi import APIRouter, Depends, HTTPException
 from pydantic import BaseModel, Field
+from sqlalchemy import select
+from sqlalchemy.ext.asyncio import AsyncSession
+
+from app.db import SearchSourceConnector, SearchSourceConnectorType, get_async_session
 
 logger = logging.getLogger(__name__)
 
@@ -212,6 +216,7 @@ def format_circleback_meeting_to_markdown(payload: CirclebackWebhookPayload) ->
 async def receive_circleback_webhook(
     search_space_id: int,
     payload: CirclebackWebhookPayload,
+    session: AsyncSession = Depends(get_async_session),
 ):
     """
     Receive and process a Circleback webhook.
@@ -223,6 +228,7 @@ async def receive_circleback_webhook(
     Args:
         search_space_id: The ID of the search space to save the document to
         payload: The Circleback webhook payload containing meeting data
+        session: Database session for looking up the connector
 
     Returns:
         Success message with document details
@@ -236,6 +242,26 @@ async def receive_circleback_webhook(
             f"Received Circleback webhook for meeting {payload.id} in search space {search_space_id}"
         )
 
+        # Look up the Circleback connector for this search space
+        connector_result = await session.execute(
+            select(SearchSourceConnector.id).where(
+                SearchSourceConnector.search_space_id == search_space_id,
+                SearchSourceConnector.connector_type
+                == SearchSourceConnectorType.CIRCLEBACK_CONNECTOR,
+            )
+        )
+        connector_id = connector_result.scalar_one_or_none()
+
+        if connector_id:
+            logger.info(
+                f"Found Circleback connector {connector_id} for search space {search_space_id}"
+            )
+        else:
+            logger.warning(
+                f"No Circleback connector found for search space {search_space_id}. "
+                "Document will be created without connector_id."
+            )
+
         # Convert to markdown
         markdown_content = format_circleback_meeting_to_markdown(payload)
 
@@ -264,6 +290,7 @@ async def receive_circleback_webhook(
             markdown_content=markdown_content,
             metadata=meeting_metadata,
             search_space_id=search_space_id,
+            connector_id=connector_id,
         )
 
         logger.info(

surfsense_backend/app/routes/composio_routes.py

@@ -20,6 +20,7 @@ from pydantic import ValidationError
 from sqlalchemy.exc import IntegrityError
 from sqlalchemy.ext.asyncio import AsyncSession
 from sqlalchemy.future import select
+from sqlalchemy.orm.attributes import flag_modified
 
 from app.config import config
 from app.db import (
@@ -330,10 +331,19 @@ async def composio_callback(
                     )
 
             # Update existing connector with new connected_account_id
+            # IMPORTANT: Merge new credentials with existing config to preserve
+            # user settings like selected_folders, selected_files, indexing_options,
+            # drive_page_token, etc. that would otherwise be wiped on reconnection.
             logger.info(
                 f"Updating existing Composio connector {existing_connector.id} with new connected_account_id {final_connected_account_id}"
             )
-            existing_connector.config = connector_config
+            existing_config = (
+                existing_connector.config.copy() if existing_connector.config else {}
+            )
+            existing_config.update(connector_config)
+            existing_connector.config = existing_config
+
+            flag_modified(existing_connector, "config")
             await session.commit()
             await session.refresh(existing_connector)
 

surfsense_backend/app/routes/notes_routes.py

@@ -76,6 +76,7 @@ async def create_note(
         document_metadata={"NOTE": True},
         embedding=None,  # Will be generated on first reindex
         updated_at=datetime.now(UTC),
+        created_by_id=user.id,  # Track who created this note
     )
 
     session.add(document)
@@ -93,6 +94,7 @@ async def create_note(
         search_space_id=document.search_space_id,
         created_at=document.created_at,
         updated_at=document.updated_at,
+        created_by_id=document.created_by_id,
     )
 
 

surfsense_backend/app/routes/search_source_connectors_routes.py

@@ -527,9 +527,17 @@ async def delete_search_source_connector(
     user: User = Depends(current_active_user),
 ):
     """
-    Delete a search source connector.
+    Delete a search source connector and all its associated documents.
+
+    The deletion runs in background via Celery task. User is notified
+    via the notification system when complete (no polling required).
+
     Requires CONNECTORS_DELETE permission.
     """
+    from app.tasks.celery_tasks.connector_deletion_task import (
+        delete_connector_with_documents_task,
+    )
+
     try:
         # Get the connector first
         result = await session.execute(
@@ -551,7 +559,12 @@ async def delete_search_source_connector(
             "You don't have permission to delete this connector",
         )
 
-        # Delete any periodic schedule associated with this connector
+        # Store connector info before we queue the deletion task
+        connector_name = db_connector.name
+        connector_type = db_connector.connector_type.value
+        search_space_id = db_connector.search_space_id
+
+        # Delete any periodic schedule associated with this connector (lightweight, sync)
         if db_connector.periodic_indexing_enabled:
             success = delete_periodic_schedule(connector_id)
             if not success:
@@ -559,7 +572,7 @@ async def delete_search_source_connector(
                     f"Failed to delete periodic schedule for connector {connector_id}"
                 )
 
-        # For Composio connectors, also delete the connected account in Composio
+        # For Composio connectors, delete the connected account in Composio (lightweight API call, sync)
         composio_connector_types = [
             SearchSourceConnectorType.COMPOSIO_GOOGLE_DRIVE_CONNECTOR,
             SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR,
@@ -591,16 +604,33 @@ async def delete_search_source_connector(
                         f"Error deleting Composio connected account {composio_connected_account_id}: {composio_error!s}"
                     )
 
-        await session.delete(db_connector)
-        await session.commit()
-        return {"message": "Search source connector deleted successfully"}
+        # Queue background task to delete documents and connector
+        # This handles potentially large document counts without blocking the API
+        delete_connector_with_documents_task.delay(
+            connector_id=connector_id,
+            user_id=str(user.id),
+            search_space_id=search_space_id,
+            connector_name=connector_name,
+            connector_type=connector_type,
+        )
+
+        logger.info(
+            f"Queued deletion task for connector {connector_id} ({connector_name})"
+        )
+
+        return {
+            "message": "Connector deletion started. You will be notified when complete.",
+            "status": "queued",
+            "connector_id": connector_id,
+            "connector_name": connector_name,
+        }
     except HTTPException:
         raise
     except Exception as e:
         await session.rollback()
         raise HTTPException(
             status_code=500,
-            detail=f"Failed to delete search source connector: {e!s}",
+            detail=f"Failed to start connector deletion: {e!s}",
         ) from e
 
 

surfsense_backend/app/schemas/documents.py

@@ -1,5 +1,6 @@
 from datetime import datetime
 from typing import TypeVar
+from uuid import UUID
 
 from pydantic import BaseModel, ConfigDict
 
@@ -51,6 +52,7 @@ class DocumentRead(BaseModel):
     created_at: datetime
     updated_at: datetime | None
     search_space_id: int
+    created_by_id: UUID | None = None  # User who created/uploaded this document
 
     model_config = ConfigDict(from_attributes=True)
 

surfsense_backend/app/tasks/celery_tasks/connector_deletion_task.py

@@ -0,0 +1,269 @@
+"""Celery task for background connector deletion.
+
+This task handles the deletion of all documents associated with a connector
+in the background, then deletes the connector itself. User is notified via
+the notification system when complete (no polling required).
+
+Features:
+- Batch deletion to handle large document counts
+- Automatic retry on failure
+- Progress tracking via notifications
+- Handles both success and failure notifications
+"""
+
+import asyncio
+import logging
+from uuid import UUID
+
+from sqlalchemy import delete, func, select
+from sqlalchemy.ext.asyncio import async_sessionmaker, create_async_engine
+from sqlalchemy.pool import NullPool
+
+from app.celery_app import celery_app
+from app.config import config
+from app.db import Document, Notification, SearchSourceConnector
+
+logger = logging.getLogger(__name__)
+
+# Batch size for document deletion
+DELETION_BATCH_SIZE = 500
+
+
+def _get_celery_session_maker():
+    """Create async session maker for Celery tasks."""
+    engine = create_async_engine(
+        config.DATABASE_URL,
+        poolclass=NullPool,
+        echo=False,
+    )
+    return async_sessionmaker(engine, expire_on_commit=False), engine
+
+
+@celery_app.task(
+    bind=True,
+    name="delete_connector_with_documents",
+    max_retries=3,
+    default_retry_delay=60,
+    autoretry_for=(Exception,),
+    retry_backoff=True,
+)
+def delete_connector_with_documents_task(
+    self,
+    connector_id: int,
+    user_id: str,
+    search_space_id: int,
+    connector_name: str,
+    connector_type: str,
+):
+    """
+    Background task to delete a connector and all its associated documents.
+
+    Creates a notification when complete (success or failure).
+    No polling required - user sees notification in UI.
+
+    Args:
+        connector_id: ID of the connector to delete
+        user_id: ID of the user who initiated the deletion
+        search_space_id: ID of the search space
+        connector_name: Name of the connector (for notification message)
+        connector_type: Type of the connector (for logging)
+    """
+    loop = asyncio.new_event_loop()
+    asyncio.set_event_loop(loop)
+
+    try:
+        return loop.run_until_complete(
+            _delete_connector_async(
+                connector_id=connector_id,
+                user_id=user_id,
+                search_space_id=search_space_id,
+                connector_name=connector_name,
+                connector_type=connector_type,
+            )
+        )
+    finally:
+        loop.close()
+
+
+async def _delete_connector_async(
+    connector_id: int,
+    user_id: str,
+    search_space_id: int,
+    connector_name: str,
+    connector_type: str,
+) -> dict:
+    """
+    Async implementation of connector deletion.
+
+    Steps:
+    1. Count total documents to delete
+    2. Delete documents in batches (chunks cascade automatically)
+    3. Delete the connector record
+    4. Create success notification
+
+    On failure, creates failure notification and re-raises exception.
+    """
+    session_maker, engine = _get_celery_session_maker()
+    total_deleted = 0
+
+    try:
+        async with session_maker() as session:
+            # Step 1: Count total documents for this connector
+            count_result = await session.execute(
+                select(func.count(Document.id)).where(
+                    Document.connector_id == connector_id
+                )
+            )
+            total_docs = count_result.scalar() or 0
+
+            logger.info(
+                f"Starting deletion of connector {connector_id} ({connector_name}). "
+                f"Documents to delete: {total_docs}"
+            )
+
+            # Step 2: Delete documents in batches
+            while True:
+                # Get batch of document IDs
+                result = await session.execute(
+                    select(Document.id)
+                    .where(Document.connector_id == connector_id)
+                    .limit(DELETION_BATCH_SIZE)
+                )
+                doc_ids = [row[0] for row in result.fetchall()]
+
+                if not doc_ids:
+                    break
+
+                # Delete this batch (chunks are deleted via CASCADE)
+                await session.execute(delete(Document).where(Document.id.in_(doc_ids)))
+                await session.commit()
+
+                total_deleted += len(doc_ids)
+                logger.info(
+                    f"Deleted batch of {len(doc_ids)} documents. "
+                    f"Progress: {total_deleted}/{total_docs}"
+                )
+
+            # Step 3: Delete the connector record
+            result = await session.execute(
+                select(SearchSourceConnector).where(
+                    SearchSourceConnector.id == connector_id
+                )
+            )
+            connector = result.scalar_one_or_none()
+
+            if connector:
+                await session.delete(connector)
+                logger.info(f"Deleted connector record: {connector_id}")
+            else:
+                logger.warning(
+                    f"Connector {connector_id} not found - may have been already deleted"
+                )
+
+            # Step 4: Create success notification
+            doc_text = "document" if total_deleted == 1 else "documents"
+            notification = Notification(
+                user_id=UUID(user_id),
+                search_space_id=search_space_id,
+                type="connector_deletion",
+                title=f"{connector_name} Removed",
+                message=f"Connector and {total_deleted} {doc_text} have been removed from your knowledge base.",
+                notification_metadata={
+                    "connector_id": connector_id,
+                    "connector_name": connector_name,
+                    "connector_type": connector_type,
+                    "documents_deleted": total_deleted,
+                    "status": "completed",
+                },
+            )
+            session.add(notification)
+            await session.commit()
+
+            logger.info(
+                f"Connector {connector_id} ({connector_name}) deleted successfully. "
+                f"Total documents deleted: {total_deleted}"
+            )
+
+            return {
+                "status": "success",
+                "connector_id": connector_id,
+                "connector_name": connector_name,
+                "documents_deleted": total_deleted,
+            }
+
+    except Exception as e:
+        logger.error(
+            f"Failed to delete connector {connector_id} ({connector_name}): {e!s}",
+            exc_info=True,
+        )
+
+        # Create failure notification
+        try:
+            async with session_maker() as session:
+                notification = Notification(
+                    user_id=UUID(user_id),
+                    search_space_id=search_space_id,
+                    type="connector_deletion",
+                    title=f"Failed to Remove {connector_name}",
+                    message="Something went wrong while removing this connector. Please try again.",
+                    notification_metadata={
+                        "connector_id": connector_id,
+                        "connector_name": connector_name,
+                        "connector_type": connector_type,
+                        "documents_deleted": total_deleted,
+                        "status": "failed",
+                        "error": str(e),
+                    },
+                )
+                session.add(notification)
+                await session.commit()
+        except Exception as notify_error:
+            logger.error(
+                f"Failed to create failure notification: {notify_error!s}",
+                exc_info=True,
+            )
+
+        # Re-raise to trigger Celery retry
+        raise
+
+    finally:
+        await engine.dispose()
+
+
+async def delete_documents_by_connector_id(
+    session,
+    connector_id: int,
+    batch_size: int = DELETION_BATCH_SIZE,
+) -> int:
+    """
+    Delete all documents associated with a connector in batches.
+
+    This is a utility function that can be used independently of the Celery task
+    for synchronous deletion scenarios (e.g., small document counts).
+
+    Args:
+        session: AsyncSession instance
+        connector_id: ID of the connector
+        batch_size: Number of documents to delete per batch
+
+    Returns:
+        Total number of documents deleted
+    """
+    total_deleted = 0
+
+    while True:
+        result = await session.execute(
+            select(Document.id)
+            .where(Document.connector_id == connector_id)
+            .limit(batch_size)
+        )
+        doc_ids = [row[0] for row in result.fetchall()]
+
+        if not doc_ids:
+            break
+
+        await session.execute(delete(Document).where(Document.id.in_(doc_ids)))
+        await session.commit()
+        total_deleted += len(doc_ids)
+
+    return total_deleted

surfsense_backend/app/tasks/celery_tasks/document_tasks.py

@@ -545,6 +545,7 @@ def process_circleback_meeting_task(
     markdown_content: str,
     metadata: dict,
     search_space_id: int,
+    connector_id: int | None = None,
 ):
     """
     Celery task to process Circleback meeting webhook data.
@@ -555,6 +556,7 @@ def process_circleback_meeting_task(
         markdown_content: Meeting content formatted as markdown
         metadata: Meeting metadata dictionary
         search_space_id: ID of the search space
+        connector_id: ID of the Circleback connector (for deletion support)
     """
     import asyncio
 
@@ -569,6 +571,7 @@ def process_circleback_meeting_task(
                 markdown_content,
                 metadata,
                 search_space_id,
+                connector_id,
             )
         )
     finally:
@@ -581,6 +584,7 @@ async def _process_circleback_meeting(
     markdown_content: str,
     metadata: dict,
     search_space_id: int,
+    connector_id: int | None = None,
 ):
     """Process Circleback meeting with new session."""
     from app.tasks.document_processors.circleback_processor import (
@@ -637,6 +641,7 @@ async def _process_circleback_meeting(
                 markdown_content=markdown_content,
                 metadata=metadata,
                 search_space_id=search_space_id,
+                connector_id=connector_id,
             )
 
             if result:

surfsense_backend/app/tasks/connector_indexers/airtable_indexer.py

@@ -417,6 +417,8 @@ async def index_airtable_records(
                                 embedding=summary_embedding,
                                 chunks=chunks,
                                 updated_at=get_current_timestamp(),
+                                created_by_id=user_id,
+                                connector_id=connector_id,
                             )
 
                             session.add(document)

surfsense_backend/app/tasks/connector_indexers/bookstack_indexer.py

@@ -396,6 +396,8 @@ async def index_bookstack_pages(
                     embedding=summary_embedding,
                     chunks=chunks,
                     updated_at=get_current_timestamp(),
+                    created_by_id=user_id,
+                    connector_id=connector_id,
                 )
 
                 session.add(document)

surfsense_backend/app/tasks/connector_indexers/clickup_indexer.py

@@ -395,6 +395,8 @@ async def index_clickup_tasks(
                         embedding=summary_embedding,
                         chunks=chunks,
                         updated_at=get_current_timestamp(),
+                        created_by_id=user_id,
+                        connector_id=connector_id,
                     )
 
                     session.add(document)

surfsense_backend/app/tasks/connector_indexers/confluence_indexer.py

@@ -402,6 +402,8 @@ async def index_confluence_pages(
                     embedding=summary_embedding,
                     chunks=chunks,
                     updated_at=get_current_timestamp(),
+                    created_by_id=user_id,
+                    connector_id=connector_id,
                 )
 
                 session.add(document)

surfsense_backend/app/tasks/connector_indexers/discord_indexer.py

@@ -527,6 +527,8 @@ async def index_discord_messages(
                                 content_hash=content_hash,
                                 unique_identifier_hash=unique_identifier_hash,
                                 updated_at=get_current_timestamp(),
+                                created_by_id=user_id,
+                                connector_id=connector_id,
                             )
 
                             session.add(document)

surfsense_backend/app/tasks/connector_indexers/elasticsearch_indexer.py

@@ -292,6 +292,8 @@ async def index_elasticsearch_documents(
                         document_metadata=metadata,
                         search_space_id=search_space_id,
                         updated_at=get_current_timestamp(),
+                        created_by_id=user_id,
+                        connector_id=connector_id,
                     )
 
                     # Create chunks and attach to document (persist via relationship)

surfsense_backend/app/tasks/connector_indexers/github_indexer.py

@@ -220,6 +220,7 @@ async def index_github_repos(
                     user_id=user_id,
                     task_logger=task_logger,
                     log_entry=log_entry,
+                    connector_id=connector_id,
                 )
 
                 documents_processed += docs_created
@@ -292,6 +293,7 @@ async def _process_repository_digest(
     user_id: str,
     task_logger: TaskLoggingService,
     log_entry,
+    connector_id: int,
 ) -> int:
     """
     Process a repository digest and create documents.
@@ -426,6 +428,8 @@ async def _process_repository_digest(
         search_space_id=search_space_id,
         chunks=chunks_data,
         updated_at=get_current_timestamp(),
+        created_by_id=user_id,
+        connector_id=connector_id,
     )
 
     session.add(document)

surfsense_backend/app/tasks/connector_indexers/google_calendar_indexer.py

@@ -499,6 +499,8 @@ async def index_google_calendar_events(
                     embedding=summary_embedding,
                     chunks=chunks,
                     updated_at=get_current_timestamp(),
+                    created_by_id=user_id,
+                    connector_id=connector_id,
                 )
 
                 session.add(document)

surfsense_backend/app/tasks/connector_indexers/google_drive_indexer.py

@@ -767,6 +767,7 @@ async def _process_single_file(
             session=session,
             task_logger=task_logger,
             log_entry=log_entry,
+            connector_id=connector_id,
         )
 
         if error:

surfsense_backend/app/tasks/connector_indexers/google_gmail_indexer.py

@@ -413,7 +413,6 @@ async def index_google_gmail_messages(
                         "subject": subject,
                         "sender": sender,
                         "date": date_str,
-                        "connector_id": connector_id,
                     },
                     content=summary_content,
                     content_hash=content_hash,
@@ -421,6 +420,8 @@ async def index_google_gmail_messages(
                     embedding=summary_embedding,
                     chunks=chunks,
                     updated_at=get_current_timestamp(),
+                    created_by_id=user_id,
+                    connector_id=connector_id,
                 )
                 session.add(document)
                 documents_indexed += 1

surfsense_backend/app/tasks/connector_indexers/jira_indexer.py

@@ -380,6 +380,8 @@ async def index_jira_issues(
                     embedding=summary_embedding,
                     chunks=chunks,
                     updated_at=get_current_timestamp(),
+                    created_by_id=user_id,
+                    connector_id=connector_id,
                 )
 
                 session.add(document)

surfsense_backend/app/tasks/connector_indexers/linear_indexer.py

@@ -413,6 +413,8 @@ async def index_linear_issues(
                     embedding=summary_embedding,
                     chunks=chunks,
                     updated_at=get_current_timestamp(),
+                    created_by_id=user_id,
+                    connector_id=connector_id,
                 )
 
                 session.add(document)

surfsense_backend/app/tasks/connector_indexers/luma_indexer.py

@@ -476,6 +476,8 @@ async def index_luma_events(
                     embedding=summary_embedding,
                     chunks=chunks,
                     updated_at=get_current_timestamp(),
+                    created_by_id=user_id,
+                    connector_id=connector_id,
                 )
 
                 session.add(document)

surfsense_backend/app/tasks/connector_indexers/notion_indexer.py

@@ -398,6 +398,7 @@ async def index_notion_pages(
                         }
                         existing_document.chunks = chunks
                         existing_document.updated_at = get_current_timestamp()
+                        existing_document.connector_id = connector_id
 
                         documents_indexed += 1
                         logger.info(f"Successfully updated Notion page: {page_title}")
@@ -470,6 +471,8 @@ async def index_notion_pages(
                     embedding=summary_embedding,
                     chunks=chunks,
                     updated_at=get_current_timestamp(),
+                    created_by_id=user_id,
+                    connector_id=connector_id,
                 )
 
                 session.add(document)

surfsense_backend/app/tasks/connector_indexers/obsidian_indexer.py

@@ -500,6 +500,8 @@ async def index_obsidian_vault(
                         embedding=embedding,
                         chunks=chunks,
                         updated_at=get_current_timestamp(),
+                        created_by_id=user_id,
+                        connector_id=connector_id,
                     )
 
                     session.add(new_document)

surfsense_backend/app/tasks/connector_indexers/slack_indexer.py

@@ -389,6 +389,8 @@ async def index_slack_messages(
                         content_hash=content_hash,
                         unique_identifier_hash=unique_identifier_hash,
                         updated_at=get_current_timestamp(),
+                        created_by_id=user_id,
+                        connector_id=connector_id,
                     )
 
                     session.add(document)

surfsense_backend/app/tasks/connector_indexers/teams_indexer.py

@@ -430,6 +430,8 @@ async def index_teams_messages(
                                 content_hash=content_hash,
                                 unique_identifier_hash=unique_identifier_hash,
                                 updated_at=get_current_timestamp(),
+                                created_by_id=user_id,
+                                connector_id=connector_id,
                             )
 
                             session.add(document)

surfsense_backend/app/tasks/connector_indexers/webcrawler_indexer.py

@@ -371,6 +371,8 @@ async def index_crawled_urls(
                     embedding=summary_embedding,
                     chunks=chunks,
                     updated_at=get_current_timestamp(),
+                    created_by_id=user_id,
+                    connector_id=connector_id,
                 )
 
                 session.add(document)

surfsense_backend/app/tasks/document_processors/circleback_processor.py

@@ -8,10 +8,17 @@ and stores it as searchable documents in the database.
 import logging
 from typing import Any
 
+from sqlalchemy import select
 from sqlalchemy.exc import SQLAlchemyError
 from sqlalchemy.ext.asyncio import AsyncSession
 
-from app.db import Document, DocumentType
+from app.db import (
+    Document,
+    DocumentType,
+    SearchSourceConnector,
+    SearchSourceConnectorType,
+    SearchSpace,
+)
 from app.services.llm_service import get_document_summary_llm
 from app.utils.document_converters import (
     create_document_chunks,
@@ -35,6 +42,7 @@ async def add_circleback_meeting_document(
     markdown_content: str,
     metadata: dict[str, Any],
     search_space_id: int,
+    connector_id: int | None = None,
 ) -> Document | None:
     """
     Process and store a Circleback meeting document.
@@ -46,6 +54,7 @@ async def add_circleback_meeting_document(
         markdown_content: Meeting content formatted as markdown
         metadata: Meeting metadata dictionary
         search_space_id: ID of the search space
+        connector_id: ID of the Circleback connector (for deletion support)
 
     Returns:
         Document object if successful, None if failed or duplicate
@@ -125,6 +134,30 @@ async def add_circleback_meeting_document(
             **metadata,
         }
 
+        # Fetch the user who set up the Circleback connector (preferred)
+        # or fall back to search space owner if no connector found
+        created_by_user_id = None
+
+        # Try to find the Circleback connector for this search space
+        connector_result = await session.execute(
+            select(SearchSourceConnector.user_id).where(
+                SearchSourceConnector.search_space_id == search_space_id,
+                SearchSourceConnector.connector_type
+                == SearchSourceConnectorType.CIRCLEBACK_CONNECTOR,
+            )
+        )
+        connector_user = connector_result.scalar_one_or_none()
+
+        if connector_user:
+            # Use the user who set up the Circleback connector
+            created_by_user_id = connector_user
+        else:
+            # Fallback: use search space owner if no connector found
+            search_space_result = await session.execute(
+                select(SearchSpace.user_id).where(SearchSpace.id == search_space_id)
+            )
+            created_by_user_id = search_space_result.scalar_one_or_none()
+
         # Update or create document
         if existing_document:
             # Update existing document
@@ -138,6 +171,9 @@ async def add_circleback_meeting_document(
             existing_document.blocknote_document = blocknote_json
             existing_document.content_needs_reindexing = False
             existing_document.updated_at = get_current_timestamp()
+            # Ensure connector_id is set (backfill for documents created before this field)
+            if connector_id is not None:
+                existing_document.connector_id = connector_id
 
             await session.commit()
             await session.refresh(existing_document)
@@ -160,6 +196,8 @@ async def add_circleback_meeting_document(
                 blocknote_document=blocknote_json,
                 content_needs_reindexing=False,
                 updated_at=get_current_timestamp(),
+                created_by_id=created_by_user_id,
+                connector_id=connector_id,
             )
 
             session.add(document)

surfsense_backend/app/tasks/document_processors/extension_processor.py

@@ -185,6 +185,7 @@ async def add_extension_received_document(
                 unique_identifier_hash=unique_identifier_hash,
                 blocknote_document=blocknote_json,
                 updated_at=get_current_timestamp(),
+                created_by_id=user_id,
             )
 
             session.add(document)

surfsense_backend/app/tasks/document_processors/file_processors.py

@@ -526,6 +526,8 @@ async def add_received_file_document_using_unstructured(
                 blocknote_document=blocknote_json,
                 content_needs_reindexing=False,
                 updated_at=get_current_timestamp(),
+                created_by_id=user_id,
+                connector_id=connector.get("connector_id") if connector else None,
             )
 
             session.add(document)
@@ -665,6 +667,8 @@ async def add_received_file_document_using_llamacloud(
                 blocknote_document=blocknote_json,
                 content_needs_reindexing=False,
                 updated_at=get_current_timestamp(),
+                created_by_id=user_id,
+                connector_id=connector.get("connector_id") if connector else None,
             )
 
             session.add(document)
@@ -829,6 +833,8 @@ async def add_received_file_document_using_docling(
                 blocknote_document=blocknote_json,
                 content_needs_reindexing=False,
                 updated_at=get_current_timestamp(),
+                created_by_id=user_id,
+                connector_id=connector.get("connector_id") if connector else None,
             )
 
             session.add(document)
@@ -849,7 +855,7 @@ async def add_received_file_document_using_docling(
 async def _update_document_from_connector(
     document: Document | None, connector: dict | None, session: AsyncSession
 ) -> None:
-    """Helper to update document type and metadata from connector info."""
+    """Helper to update document type, metadata, and connector_id from connector info."""
     if document and connector:
         if "type" in connector:
             document.document_type = connector["type"]
@@ -861,6 +867,9 @@ async def _update_document_from_connector(
                 # Expand existing metadata with connector metadata
                 merged = {**document.document_metadata, **connector["metadata"]}
                 document.document_metadata = merged
+        # Set connector_id if provided for de-indexing support
+        if "connector_id" in connector:
+            document.connector_id = connector["connector_id"]
         await session.commit()
 
 

surfsense_backend/app/tasks/document_processors/markdown_processor.py

@@ -295,6 +295,8 @@ async def add_received_markdown_file_document(
                 unique_identifier_hash=primary_hash,
                 blocknote_document=blocknote_json,
                 updated_at=get_current_timestamp(),
+                created_by_id=user_id,
+                connector_id=connector.get("connector_id") if connector else None,
             )
 
             session.add(document)

surfsense_backend/app/tasks/document_processors/youtube_processor.py

@@ -357,6 +357,7 @@ async def add_youtube_video_document(
                 unique_identifier_hash=unique_identifier_hash,
                 blocknote_document=blocknote_json,
                 updated_at=get_current_timestamp(),
+                created_by_id=user_id,
             )
 
             session.add(document)

surfsense_web/app/dashboard/[search_space_id]/team/page.tsx

@@ -206,7 +206,7 @@ export default function TeamManagementPage() {
 	);
 
 	const handleUpdateRole = useCallback(
-		async (roleId: number, data: { permissions?: string[] }): Promise<Role> => {
+		async (roleId: number, data: { name?: string; description?: string | null; permissions?: string[]; is_default?: boolean }): Promise<Role> => {
 			const request: UpdateRoleRequest = {
 				search_space_id: searchSpaceId,
 				role_id: roleId,
@@ -944,7 +944,7 @@ function RolesTab({
 	roles,
 	groupedPermissions,
 	loading,
-	onUpdateRole: _onUpdateRole,
+	onUpdateRole,
 	onDeleteRole,
 	onCreateRole,
 	canUpdate,
@@ -954,7 +954,7 @@ function RolesTab({
 	roles: Role[];
 	groupedPermissions: Record<string, PermissionWithDescription[]>;
 	loading: boolean;
-	onUpdateRole: (roleId: number, data: { permissions?: string[] }) => Promise<Role>;
+	onUpdateRole: (roleId: number, data: { name?: string; description?: string | null; permissions?: string[]; is_default?: boolean }) => Promise<Role>;
 	onDeleteRole: (roleId: number) => Promise<boolean>;
 	onCreateRole: (data: CreateRoleRequest["data"]) => Promise<Role>;
 	canUpdate: boolean;
@@ -962,6 +962,7 @@ function RolesTab({
 	canCreate: boolean;
 }) {
 	const [showCreateRole, setShowCreateRole] = useState(false);
+	const [editingRoleId, setEditingRoleId] = useState<number | null>(null);
 
 	if (loading) {
 		return (
@@ -997,6 +998,20 @@ function RolesTab({
 				/>
 			)}
 
+			{/* Edit Role Form */}
+			{editingRoleId !== null && (() => {
+				const roleToEdit = roles.find((r) => r.id === editingRoleId);
+				if (!roleToEdit) return null;
+				return (
+					<EditRoleSection
+						role={roleToEdit}
+						groupedPermissions={groupedPermissions}
+						onUpdateRole={onUpdateRole}
+						onCancel={() => setEditingRoleId(null)}
+					/>
+				);
+			})()}
+
 			{/* Roles Grid */}
 			<div className="grid grid-cols-1 md:grid-cols-2 lg:grid-cols-3 gap-4">
 				{roles.map((role, index) => (
@@ -1055,12 +1070,13 @@ function RolesTab({
 													<MoreHorizontal className="h-4 w-4" />
 												</Button>
 											</DropdownMenuTrigger>
-											<DropdownMenuContent align="end">
+											<DropdownMenuContent
+												align="end"
+												onCloseAutoFocus={(e) => e.preventDefault()}
+											>
 												{canUpdate && (
 													<DropdownMenuItem
-														onClick={() => {
-															// TODO: Implement edit role dialog/modal
-														}}
+														onClick={() => setEditingRoleId(role.id)}
 													>
 														<Edit2 className="h-4 w-4 mr-2" />
 														Edit Role
@@ -2026,3 +2042,363 @@ function CreateRoleSection({
 		</motion.div>
 	);
 }
+
+function EditRoleSection({
+	role,
+	groupedPermissions,
+	onUpdateRole,
+	onCancel,
+}: {
+	role: Role;
+	groupedPermissions: Record<string, PermissionWithDescription[]>;
+	onUpdateRole: (roleId: number, data: { name?: string; description?: string | null; permissions?: string[]; is_default?: boolean }) => Promise<Role>;
+	onCancel: () => void;
+}) {
+	const [saving, setSaving] = useState(false);
+	const [name, setName] = useState(role.name);
+	const [description, setDescription] = useState(role.description || "");
+	const [selectedPermissions, setSelectedPermissions] = useState<string[]>(role.permissions);
+	const [isDefault, setIsDefault] = useState(role.is_default);
+	const [expandedCategories, setExpandedCategories] = useState<string[]>([]);
+
+	// Sort categories by order
+	const sortedCategories = useMemo(() => {
+		return Object.keys(groupedPermissions).sort((a, b) => {
+			const orderA = CATEGORY_CONFIG[a]?.order ?? 99;
+			const orderB = CATEGORY_CONFIG[b]?.order ?? 99;
+			return orderA - orderB;
+		});
+	}, [groupedPermissions]);
+
+	const handleSave = async () => {
+		if (!name.trim()) {
+			toast.error("Please enter a role name");
+			return;
+		}
+
+		setSaving(true);
+		try {
+			await onUpdateRole(role.id, {
+				name: name.trim(),
+				description: description.trim() || null,
+				permissions: selectedPermissions,
+				is_default: isDefault,
+			});
+			toast.success("Role updated successfully");
+			onCancel();
+		} catch (error) {
+			console.error("Failed to update role:", error);
+			toast.error("Failed to update role");
+		} finally {
+			setSaving(false);
+		}
+	};
+
+	const togglePermission = useCallback((perm: string) => {
+		setSelectedPermissions((prev) =>
+			prev.includes(perm) ? prev.filter((p) => p !== perm) : [...prev, perm]
+		);
+	}, []);
+
+	const toggleCategory = useCallback(
+		(category: string) => {
+			const categoryPerms = groupedPermissions[category]?.map((p) => p.value) || [];
+			const allSelected = categoryPerms.every((p) => selectedPermissions.includes(p));
+
+			if (allSelected) {
+				setSelectedPermissions((prev) => prev.filter((p) => !categoryPerms.includes(p)));
+			} else {
+				setSelectedPermissions((prev) => [...new Set([...prev, ...categoryPerms])]);
+			}
+		},
+		[groupedPermissions, selectedPermissions]
+	);
+
+	const toggleCategoryExpanded = useCallback((category: string) => {
+		setExpandedCategories((prev) =>
+			prev.includes(category) ? prev.filter((c) => c !== category) : [...prev, category]
+		);
+	}, []);
+
+	const getCategoryStats = useCallback(
+		(category: string) => {
+			const perms = groupedPermissions[category] || [];
+			const selected = perms.filter((p) => selectedPermissions.includes(p.value)).length;
+			return { selected, total: perms.length, allSelected: selected === perms.length };
+		},
+		[groupedPermissions, selectedPermissions]
+	);
+
+	return (
+		<motion.div
+			initial={{ opacity: 0, y: -10 }}
+			animate={{ opacity: 1, y: 0 }}
+			exit={{ opacity: 0, y: -10 }}
+			className="mb-6"
+		>
+			<Card className="border-primary/20 bg-gradient-to-br from-primary/5 via-background to-background">
+				<CardHeader className="pb-4">
+					<div className="flex items-center justify-between">
+						<div className="flex items-center gap-3">
+							<div className="h-10 w-10 rounded-xl bg-primary/10 flex items-center justify-center">
+								<Edit2 className="h-5 w-5 text-primary" />
+							</div>
+							<div>
+								<CardTitle className="text-lg">Edit Role</CardTitle>
+								<CardDescription className="text-sm">
+									Modify permissions for "{role.name}"
+								</CardDescription>
+							</div>
+						</div>
+						<Button variant="ghost" size="icon" onClick={onCancel}>
+							<Trash2 className="h-4 w-4" />
+						</Button>
+					</div>
+				</CardHeader>
+				<CardContent className="space-y-6">
+					{/* Role Details */}
+					<div className="grid grid-cols-1 md:grid-cols-2 gap-4">
+						<div className="space-y-2">
+							<Label htmlFor="edit-role-name">Role Name *</Label>
+							<Input
+								id="edit-role-name"
+								placeholder="e.g., Content Manager"
+								value={name}
+								onChange={(e) => setName(e.target.value)}
+							/>
+						</div>
+						<div className="space-y-2">
+							<Label htmlFor="edit-role-description">Description</Label>
+							<Input
+								id="edit-role-description"
+								placeholder="Brief description of this role"
+								value={description}
+								onChange={(e) => setDescription(e.target.value)}
+							/>
+						</div>
+					</div>
+
+					{/* Default Role Checkbox */}
+					<div className="flex items-center gap-3 p-3 rounded-lg bg-muted/50">
+						<Checkbox
+							id="edit-is-default"
+							checked={isDefault}
+							onCheckedChange={(checked) => setIsDefault(checked === true)}
+						/>
+						<div className="flex-1">
+							<Label htmlFor="edit-is-default" className="cursor-pointer font-medium">
+								Set as default role
+							</Label>
+							<p className="text-xs text-muted-foreground">
+								New members without a specific role will be assigned this role
+							</p>
+						</div>
+					</div>
+
+					{/* Permissions Section */}
+					<div className="space-y-3">
+						<div className="flex items-center justify-between">
+							<Label className="text-sm font-medium">
+								Permissions ({selectedPermissions.length} selected)
+							</Label>
+							<Button
+								type="button"
+								variant="ghost"
+								size="sm"
+								className="text-xs h-7"
+								onClick={() =>
+									setExpandedCategories(
+										expandedCategories.length === sortedCategories.length ? [] : sortedCategories
+									)
+								}
+							>
+								{expandedCategories.length === sortedCategories.length
+									? "Collapse All"
+									: "Expand All"}
+							</Button>
+						</div>
+
+						<div className="space-y-2">
+							{sortedCategories.map((category) => {
+								const config = CATEGORY_CONFIG[category] || {
+									label: category,
+									icon: FileText,
+									description: "",
+									order: 99,
+								};
+								const IconComponent = config.icon;
+								const stats = getCategoryStats(category);
+								const isExpanded = expandedCategories.includes(category);
+								const perms = groupedPermissions[category] || [];
+
+								return (
+									<div key={category} className="rounded-lg border bg-card overflow-hidden">
+										{/* Category Header */}
+										<div
+											className={cn(
+												"flex items-center justify-between p-3 cursor-pointer hover:bg-muted/50 transition-colors",
+												stats.allSelected && "bg-primary/5"
+											)}
+											onClick={() => toggleCategoryExpanded(category)}
+											onKeyDown={(e) => {
+												if (e.key === "Enter" || e.key === " ") {
+													e.preventDefault();
+													toggleCategoryExpanded(category);
+												}
+											}}
+											tabIndex={0}
+											role="button"
+										>
+											<div className="flex items-center gap-3">
+												<div
+													className={cn(
+														"h-8 w-8 rounded-lg flex items-center justify-center",
+														stats.selected > 0 ? "bg-primary/10" : "bg-muted"
+													)}
+												>
+													<IconComponent
+														className={cn(
+															"h-4 w-4",
+															stats.selected > 0 ? "text-primary" : "text-muted-foreground"
+														)}
+													/>
+												</div>
+												<div>
+													<div className="flex items-center gap-2">
+														<span className="font-medium text-sm">{config.label}</span>
+														<Badge
+															variant={stats.selected > 0 ? "default" : "secondary"}
+															className="text-xs h-5"
+														>
+															{stats.selected}/{stats.total}
+														</Badge>
+													</div>
+													<p className="text-xs text-muted-foreground hidden md:block">
+														{config.description}
+													</p>
+												</div>
+											</div>
+											<div className="flex items-center gap-2">
+												<Checkbox
+													checked={stats.allSelected}
+													onCheckedChange={() => toggleCategory(category)}
+													onClick={(e) => e.stopPropagation()}
+													aria-label={`Select all ${config.label} permissions`}
+												/>
+												<motion.div
+													animate={{ rotate: isExpanded ? 180 : 0 }}
+													transition={{ duration: 0.2 }}
+												>
+													<svg
+														className="h-4 w-4 text-muted-foreground"
+														fill="none"
+														viewBox="0 0 24 24"
+														stroke="currentColor"
+													>
+														<path
+															strokeLinecap="round"
+															strokeLinejoin="round"
+															strokeWidth={2}
+															d="M19 9l-7 7-7-7"
+														/>
+													</svg>
+												</motion.div>
+											</div>
+										</div>
+
+										{/* Permissions List */}
+										{isExpanded && (
+											<motion.div
+												initial={{ height: 0, opacity: 0 }}
+												animate={{ height: "auto", opacity: 1 }}
+												exit={{ height: 0, opacity: 0 }}
+												transition={{ duration: 0.2 }}
+												className="border-t"
+											>
+												<div className="p-3 space-y-1">
+													{perms.map((perm) => {
+														const action = perm.value.split(":")[1];
+														const actionConfig = ACTION_DISPLAY[action] || {
+															label: action,
+															color: "text-gray-600 bg-gray-500/10",
+														};
+														const isSelected = selectedPermissions.includes(perm.value);
+
+														return (
+															<div
+																key={perm.value}
+																className={cn(
+																	"flex items-center justify-between p-2 rounded-md cursor-pointer transition-colors",
+																	isSelected
+																		? "bg-primary/10 hover:bg-primary/15"
+																		: "hover:bg-muted/50"
+																)}
+																onClick={() => togglePermission(perm.value)}
+																onKeyDown={(e) => {
+																	if (e.key === "Enter" || e.key === " ") {
+																		e.preventDefault();
+																		togglePermission(perm.value);
+																	}
+																}}
+																tabIndex={0}
+																role="checkbox"
+																aria-checked={isSelected}
+															>
+																<div className="flex items-center gap-3 flex-1 min-w-0">
+																	<Checkbox
+																		checked={isSelected}
+																		onCheckedChange={() => togglePermission(perm.value)}
+																		onClick={(e) => e.stopPropagation()}
+																	/>
+																	<div className="flex-1 min-w-0">
+																		<div className="flex items-center gap-2">
+																			<span
+																				className={cn(
+																					"text-xs font-medium px-2 py-0.5 rounded",
+																					actionConfig.color
+																				)}
+																			>
+																				{actionConfig.label}
+																			</span>
+																		</div>
+																		<p className="text-xs text-muted-foreground mt-0.5 truncate">
+																			{perm.description}
+																		</p>
+																	</div>
+																</div>
+															</div>
+														);
+													})}
+												</div>
+											</motion.div>
+										)}
+									</div>
+								);
+							})}
+						</div>
+					</div>
+
+					{/* Actions */}
+					<div className="flex items-center justify-end gap-3 pt-4 border-t">
+						<Button variant="outline" onClick={onCancel}>
+							Cancel
+						</Button>
+						<Button onClick={handleSave} disabled={saving || !name.trim()}>
+							{saving ? (
+								<>
+									<Spinner size="sm" className="mr-2" />
+									Saving...
+								</>
+							) : (
+								<>
+									<Check className="h-4 w-4 mr-2" />
+									Save Changes
+								</>
+							)}
+						</Button>
+					</div>
+				</CardContent>
+			</Card>
+		</motion.div>
+	);
+}

surfsense_web/components/assistant-ui/inline-mention-editor.tsx

@@ -536,10 +536,11 @@ export const InlineMentionEditor = forwardRef<InlineMentionEditorRef, InlineMent
 					role="textbox"
 					aria-multiline="true"
 				/>
-				{/* Placeholder */}
+				{/* Placeholder with fade animation on change */}
 				{isEmpty && (
 					<div
-						className="absolute top-0 left-0 pointer-events-none text-muted-foreground text-sm"
+						key={placeholder}
+						className="absolute top-0 left-0 pointer-events-none text-muted-foreground text-sm animate-in fade-in duration-1000"
 						aria-hidden="true"
 					>
 						{placeholder}

surfsense_web/components/assistant-ui/thread.tsx

@@ -65,6 +65,16 @@ import type { Document } from "@/contracts/types/document.types";
 import { useCommentsElectric } from "@/hooks/use-comments-electric";
 import { cn } from "@/lib/utils";
 
+/** Placeholder texts that cycle in new chats when input is empty */
+const CYCLING_PLACEHOLDERS = [
+	"Ask SurfSense anything or @mention docs.",
+	"Generate a podcast from marketing tips in the company handbook.",
+	"Sum up our vacation policy from Drive.",
+	"Give me a brief overview of the most urgent tickets in Jira and Linear.",
+	"Create a concise table of today's top ten emails and calendar events.",
+	"Check if this week's Slack messages reference any GitHub issues.",
+];
+
 interface ThreadProps {
 	messageThinkingSteps?: Map<string, ThinkingStep[]>;
 	header?: React.ReactNode;
@@ -228,6 +238,30 @@ const Composer: FC = () => {
 	const isThreadEmpty = useAssistantState(({ thread }) => thread.isEmpty);
 	const isThreadRunning = useAssistantState(({ thread }) => thread.isRunning);
 
+	// Cycling placeholder state - only cycles in new chats
+	const [placeholderIndex, setPlaceholderIndex] = useState(0);
+
+	// Cycle through placeholders every 4 seconds when thread is empty (new chat)
+	useEffect(() => {
+		// Only cycle when thread is empty (new chat)
+		if (!isThreadEmpty) {
+			// Reset to first placeholder when chat becomes active
+			setPlaceholderIndex(0);
+			return;
+		}
+
+		const intervalId = setInterval(() => {
+			setPlaceholderIndex((prev) => (prev + 1) % CYCLING_PLACEHOLDERS.length);
+		}, 6000);
+
+		return () => clearInterval(intervalId);
+	}, [isThreadEmpty]);
+
+	// Compute current placeholder - only cycle in new chats
+	const currentPlaceholder = isThreadEmpty
+		? CYCLING_PLACEHOLDERS[placeholderIndex]
+		: CYCLING_PLACEHOLDERS[0];
+
 	// Live collaboration state
 	const { data: currentUser } = useAtomValue(currentUserAtom);
 	const { data: members } = useAtomValue(membersAtom);
@@ -410,7 +444,7 @@ const Composer: FC = () => {
 				<div ref={editorContainerRef} className="aui-composer-input-wrapper px-3 pt-3 pb-6">
 					<InlineMentionEditor
 						ref={editorRef}
-						placeholder="Ask SurfSense or @mention docs"
+						placeholder={currentPlaceholder}
 						onMentionTrigger={handleMentionTrigger}
 						onMentionClose={handleMentionClose}
 						onChange={handleEditorChange}

surfsense_web/components/layout/ui/sidebar/InboxSidebar.tsx

@@ -237,7 +237,7 @@ export function InboxSidebar({
 	const currentDataSource = activeTab === "mentions" ? mentions : status;
 	const { loading, loadingMore = false, hasMore = false, loadMore } = currentDataSource;
 
-	// Status tab includes: connector indexing, document processing, page limit exceeded
+	// Status tab includes: connector indexing, document processing, page limit exceeded, connector deletion
 	// Filter to only show status notification types
 	const statusItems = useMemo(
 		() =>
@@ -245,7 +245,8 @@ export function InboxSidebar({
 				(item) =>
 					item.type === "connector_indexing" ||
 					item.type === "document_processing" ||
-					item.type === "page_limit_exceeded"
+					item.type === "page_limit_exceeded" ||
+					item.type === "connector_deletion"
 			),
 		[status.items]
 	);

surfsense_web/contracts/types/inbox.types.ts

@@ -7,6 +7,7 @@ import { documentTypeEnum } from "./document.types";
  */
 export const inboxItemTypeEnum = z.enum([
 	"connector_indexing",
+	"connector_deletion",
 	"document_processing",
 	"new_mention",
 	"page_limit_exceeded",
@@ -60,6 +61,17 @@ export const connectorIndexingMetadata = baseInboxItemMetadata.extend({
 	file_names: z.array(z.string()).optional(),
 });
 
+/**
+ * Connector deletion metadata schema
+ */
+export const connectorDeletionMetadata = baseInboxItemMetadata.extend({
+	connector_id: z.number(),
+	connector_name: z.string(),
+	connector_type: z.string(),
+	documents_deleted: z.number(),
+	error: z.string().optional(),
+});
+
 /**
  * Document processing metadata schema
  */
@@ -110,6 +122,7 @@ export const pageLimitExceededMetadata = baseInboxItemMetadata.extend({
  */
 export const inboxItemMetadata = z.union([
 	connectorIndexingMetadata,
+	connectorDeletionMetadata,
 	documentProcessingMetadata,
 	newMentionMetadata,
 	pageLimitExceededMetadata,
@@ -140,6 +153,11 @@ export const connectorIndexingInboxItem = inboxItem.extend({
 	metadata: connectorIndexingMetadata,
 });
 
+export const connectorDeletionInboxItem = inboxItem.extend({
+	type: z.literal("connector_deletion"),
+	metadata: connectorDeletionMetadata,
+});
+
 export const documentProcessingInboxItem = inboxItem.extend({
 	type: z.literal("document_processing"),
 	metadata: documentProcessingMetadata,
@@ -235,6 +253,15 @@ export function isConnectorIndexingMetadata(
 	return connectorIndexingMetadata.safeParse(metadata).success;
 }
 
+/**
+ * Type guard for ConnectorDeletionMetadata
+ */
+export function isConnectorDeletionMetadata(
+	metadata: unknown
+): metadata is ConnectorDeletionMetadata {
+	return connectorDeletionMetadata.safeParse(metadata).success;
+}
+
 /**
  * Type guard for DocumentProcessingMetadata
  */
@@ -268,6 +295,7 @@ export function parseInboxItemMetadata(
 	metadata: unknown
 ):
 	| ConnectorIndexingMetadata
+	| ConnectorDeletionMetadata
 	| DocumentProcessingMetadata
 	| NewMentionMetadata
 	| PageLimitExceededMetadata
@@ -277,6 +305,10 @@ export function parseInboxItemMetadata(
 			const result = connectorIndexingMetadata.safeParse(metadata);
 			return result.success ? result.data : null;
 		}
+		case "connector_deletion": {
+			const result = connectorDeletionMetadata.safeParse(metadata);
+			return result.success ? result.data : null;
+		}
 		case "document_processing": {
 			const result = documentProcessingMetadata.safeParse(metadata);
 			return result.success ? result.data : null;
@@ -303,12 +335,14 @@ export type InboxItemStatusEnum = z.infer<typeof inboxItemStatusEnum>;
 export type DocumentProcessingStageEnum = z.infer<typeof documentProcessingStageEnum>;
 export type BaseInboxItemMetadata = z.infer<typeof baseInboxItemMetadata>;
 export type ConnectorIndexingMetadata = z.infer<typeof connectorIndexingMetadata>;
+export type ConnectorDeletionMetadata = z.infer<typeof connectorDeletionMetadata>;
 export type DocumentProcessingMetadata = z.infer<typeof documentProcessingMetadata>;
 export type NewMentionMetadata = z.infer<typeof newMentionMetadata>;
 export type PageLimitExceededMetadata = z.infer<typeof pageLimitExceededMetadata>;
 export type InboxItemMetadata = z.infer<typeof inboxItemMetadata>;
 export type InboxItem = z.infer<typeof inboxItem>;
 export type ConnectorIndexingInboxItem = z.infer<typeof connectorIndexingInboxItem>;
+export type ConnectorDeletionInboxItem = z.infer<typeof connectorDeletionInboxItem>;
 export type DocumentProcessingInboxItem = z.infer<typeof documentProcessingInboxItem>;
 export type NewMentionInboxItem = z.infer<typeof newMentionInboxItem>;
 export type PageLimitExceededInboxItem = z.infer<typeof pageLimitExceededInboxItem>;