diff --git a/surfsense_backend/app/agents/new_chat/tools/podcast.py b/surfsense_backend/app/agents/new_chat/tools/podcast.py
index 424b04f77..1048ed881 100644
--- a/surfsense_backend/app/agents/new_chat/tools/podcast.py
+++ b/surfsense_backend/app/agents/new_chat/tools/podcast.py
@@ -54,7 +54,9 @@ def set_generating_podcast(search_space_id: int, podcast_id: int) -> None:
         client = get_redis_client()
         client.setex(_redis_key(search_space_id), 1800, str(podcast_id))
     except Exception as e:
-        print(f"[generate_podcast] Warning: Could not set generating podcast in Redis: {e}")
+        print(
+            f"[generate_podcast] Warning: Could not set generating podcast in Redis: {e}"
+        )
 
 
 def create_generate_podcast_tool(
diff --git a/surfsense_backend/app/routes/new_chat_routes.py b/surfsense_backend/app/routes/new_chat_routes.py
index 541e25a75..38352d348 100644
--- a/surfsense_backend/app/routes/new_chat_routes.py
+++ b/surfsense_backend/app/routes/new_chat_routes.py
@@ -670,7 +670,9 @@ async def delete_thread(
         ) from None
 
 
-@router.post("/threads/{thread_id}/complete-clone", response_model=CompleteCloneResponse)
+@router.post(
+    "/threads/{thread_id}/complete-clone", response_model=CompleteCloneResponse
+)
 async def complete_clone(
     thread_id: int,
     session: AsyncSession = Depends(get_async_session),
@@ -702,7 +704,9 @@ async def complete_clone(
             raise HTTPException(status_code=400, detail="Clone already completed")
 
         if not thread.cloned_from_thread_id:
-            raise HTTPException(status_code=400, detail="No source thread to clone from")
+            raise HTTPException(
+                status_code=400, detail="No source thread to clone from"
+            )
 
         message_count = await complete_clone_content(
             session=session,
diff --git a/surfsense_backend/app/routes/public_chat_routes.py b/surfsense_backend/app/routes/public_chat_routes.py
index 8b4f42559..4676f2ad0 100644
--- a/surfsense_backend/app/routes/public_chat_routes.py
+++ b/surfsense_backend/app/routes/public_chat_routes.py
@@ -53,7 +53,9 @@ async def clone_public_chat_endpoint(
     source_thread = await get_thread_by_share_token(session, share_token)
 
     if not source_thread:
-        raise HTTPException(status_code=404, detail="Chat not found or no longer public")
+        raise HTTPException(
+            status_code=404, detail="Chat not found or no longer public"
+        )
 
     target_search_space_id = await get_user_default_search_space(session, user.id)
 
diff --git a/surfsense_backend/app/routes/search_source_connectors_routes.py b/surfsense_backend/app/routes/search_source_connectors_routes.py
index 2237ddfa8..c4d4fdb3b 100644
--- a/surfsense_backend/app/routes/search_source_connectors_routes.py
+++ b/surfsense_backend/app/routes/search_source_connectors_routes.py
@@ -187,6 +187,7 @@ async def create_search_source_connector(
                 user_id=str(user.id),
                 connector_type=db_connector.connector_type,
                 frequency_minutes=db_connector.indexing_frequency_minutes,
+                connector_config=db_connector.config,
             )
             if not success:
                 logger.warning(
@@ -646,6 +647,7 @@ async def index_connector_content(
 
         # Handle different connector types
         response_message = ""
+        indexing_started = True
         # Use UTC for consistency with last_indexed_at storage
         today_str = datetime.now(UTC).strftime("%Y-%m-%d")
 
@@ -921,14 +923,31 @@ async def index_connector_content(
 
         elif connector.connector_type == SearchSourceConnectorType.WEBCRAWLER_CONNECTOR:
             from app.tasks.celery_tasks.connector_tasks import index_crawled_urls_task
+            from app.utils.webcrawler_utils import parse_webcrawler_urls
 
-            logger.info(
-                f"Triggering web pages indexing for connector {connector_id} into search space {search_space_id} from {indexing_from} to {indexing_to}"
-            )
-            index_crawled_urls_task.delay(
-                connector_id, search_space_id, str(user.id), indexing_from, indexing_to
-            )
-            response_message = "Web page indexing started in the background."
+            # Check if URLs are configured before triggering indexing
+            connector_config = connector.config or {}
+            urls = parse_webcrawler_urls(connector_config.get("INITIAL_URLS"))
+
+            if not urls:
+                # URLs are optional - skip indexing gracefully
+                logger.info(
+                    f"Webcrawler connector {connector_id} has no URLs configured, skipping indexing"
+                )
+                response_message = "No URLs configured for this connector. Add URLs in the connector settings to enable indexing."
+                indexing_started = False
+            else:
+                logger.info(
+                    f"Triggering web pages indexing for connector {connector_id} into search space {search_space_id} from {indexing_from} to {indexing_to}"
+                )
+                index_crawled_urls_task.delay(
+                    connector_id,
+                    search_space_id,
+                    str(user.id),
+                    indexing_from,
+                    indexing_to,
+                )
+                response_message = "Web page indexing started in the background."
 
         elif connector.connector_type == SearchSourceConnectorType.OBSIDIAN_CONNECTOR:
             from app.config import config as app_config
@@ -1025,6 +1044,7 @@ async def index_connector_content(
 
         return {
             "message": response_message,
+            "indexing_started": indexing_started,
             "connector_id": connector_id,
             "search_space_id": search_space_id,
             "indexing_from": indexing_from,
diff --git a/surfsense_backend/app/schemas/new_chat.py b/surfsense_backend/app/schemas/new_chat.py
index b420b1b91..ab6be9c9f 100644
--- a/surfsense_backend/app/schemas/new_chat.py
+++ b/surfsense_backend/app/schemas/new_chat.py
@@ -257,14 +257,11 @@ class PublicChatResponse(BaseModel):
 
 
 class CloneInitResponse(BaseModel):
-
-
     thread_id: int
     search_space_id: int
     share_token: str
 
 
 class CompleteCloneResponse(BaseModel):
-
     status: str
     message_count: int
diff --git a/surfsense_backend/app/schemas/podcasts.py b/surfsense_backend/app/schemas/podcasts.py
index 9e5cb0262..60f9d7dc0 100644
--- a/surfsense_backend/app/schemas/podcasts.py
+++ b/surfsense_backend/app/schemas/podcasts.py
@@ -59,6 +59,8 @@ class PodcastRead(PodcastBase):
             "search_space_id": obj.search_space_id,
             "status": obj.status,
             "created_at": obj.created_at,
-            "transcript_entries": len(obj.podcast_transcript) if obj.podcast_transcript else None,
+            "transcript_entries": len(obj.podcast_transcript)
+            if obj.podcast_transcript
+            else None,
         }
         return cls(**data)
diff --git a/surfsense_backend/app/services/public_chat_service.py b/surfsense_backend/app/services/public_chat_service.py
index 79618974f..a5b8c9ffe 100644
--- a/surfsense_backend/app/services/public_chat_service.py
+++ b/surfsense_backend/app/services/public_chat_service.py
@@ -291,6 +291,9 @@ async def complete_clone_content(
 
                     if old_podcast_id and old_podcast_id in podcast_id_map:
                         result_data["podcast_id"] = podcast_id_map[old_podcast_id]
+                    elif old_podcast_id:
+                        # Podcast couldn't be cloned (not ready), remove reference
+                        result_data.pop("podcast_id", None)
 
         new_message = NewChatMessage(
             thread_id=target_thread.id,
diff --git a/surfsense_backend/app/tasks/celery_tasks/podcast_tasks.py b/surfsense_backend/app/tasks/celery_tasks/podcast_tasks.py
index 0ce714cdc..2ce8716e0 100644
--- a/surfsense_backend/app/tasks/celery_tasks/podcast_tasks.py
+++ b/surfsense_backend/app/tasks/celery_tasks/podcast_tasks.py
@@ -55,7 +55,9 @@ def _clear_generating_podcast(search_space_id: int) -> None:
         client = redis.from_url(redis_url, decode_responses=True)
         key = f"podcast:generating:{search_space_id}"
         client.delete(key)
-        logger.info(f"Cleared generating podcast key for search_space_id={search_space_id}")
+        logger.info(
+            f"Cleared generating podcast key for search_space_id={search_space_id}"
+        )
     except Exception as e:
         logger.warning(f"Could not clear generating podcast key: {e}")
 
@@ -119,9 +121,7 @@ async def _generate_content_podcast(
 ) -> dict:
     """Generate content-based podcast and update existing record."""
     async with get_celery_session_maker()() as session:
-        result = await session.execute(
-            select(Podcast).filter(Podcast.id == podcast_id)
-        )
+        result = await session.execute(select(Podcast).filter(Podcast.id == podcast_id))
         podcast = result.scalars().first()
 
         if not podcast:
diff --git a/surfsense_backend/app/tasks/celery_tasks/schedule_checker_task.py b/surfsense_backend/app/tasks/celery_tasks/schedule_checker_task.py
index bf80cbe78..b33e25170 100644
--- a/surfsense_backend/app/tasks/celery_tasks/schedule_checker_task.py
+++ b/surfsense_backend/app/tasks/celery_tasks/schedule_checker_task.py
@@ -156,6 +156,41 @@ async def _check_and_trigger_schedules():
                             )
                             await session.commit()
                             continue
+
+                    # Special handling for Webcrawler - skip if no URLs configured
+                    elif (
+                        connector.connector_type
+                        == SearchSourceConnectorType.WEBCRAWLER_CONNECTOR
+                    ):
+                        from app.utils.webcrawler_utils import parse_webcrawler_urls
+
+                        connector_config = connector.config or {}
+                        urls = parse_webcrawler_urls(
+                            connector_config.get("INITIAL_URLS")
+                        )
+
+                        if urls:
+                            task.delay(
+                                connector.id,
+                                connector.search_space_id,
+                                str(connector.user_id),
+                                None,  # start_date
+                                None,  # end_date
+                            )
+                        else:
+                            # No URLs configured - skip indexing but still update next_scheduled_at
+                            logger.info(
+                                f"Webcrawler connector {connector.id} has no URLs configured, "
+                                "skipping periodic indexing (will check again at next scheduled time)"
+                            )
+                            from datetime import timedelta
+
+                            connector.next_scheduled_at = now + timedelta(
+                                minutes=connector.indexing_frequency_minutes
+                            )
+                            await session.commit()
+                            continue
+
                     else:
                         task.delay(
                             connector.id,
diff --git a/surfsense_backend/app/tasks/connector_indexers/airtable_indexer.py b/surfsense_backend/app/tasks/connector_indexers/airtable_indexer.py
index 4d5a33b79..6bb62d716 100644
--- a/surfsense_backend/app/tasks/connector_indexers/airtable_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/airtable_indexer.py
@@ -20,6 +20,7 @@ from app.utils.document_converters import (
 from .base import (
     calculate_date_range,
     check_document_by_unique_identifier,
+    check_duplicate_document_by_hash,
     get_connector_by_id,
     get_current_timestamp,
     logger,
@@ -317,6 +318,24 @@ async def index_airtable_records(
                                     )
                                     continue
 
+                            # Document doesn't exist by unique_identifier_hash
+                            # Check if a document with the same content_hash exists (from another connector)
+                            with session.no_autoflush:
+                                duplicate_by_content = (
+                                    await check_duplicate_document_by_hash(
+                                        session, content_hash
+                                    )
+                                )
+
+                            if duplicate_by_content:
+                                logger.info(
+                                    f"Airtable record {record_id} already indexed by another connector "
+                                    f"(existing document ID: {duplicate_by_content.id}, "
+                                    f"type: {duplicate_by_content.document_type}). Skipping."
+                                )
+                                documents_skipped += 1
+                                continue
+
                             # Document doesn't exist - create new one
                             # Generate document summary
                             user_llm = await get_user_long_context_llm(
diff --git a/surfsense_backend/app/tasks/connector_indexers/bookstack_indexer.py b/surfsense_backend/app/tasks/connector_indexers/bookstack_indexer.py
index a1067255d..e183ab333 100644
--- a/surfsense_backend/app/tasks/connector_indexers/bookstack_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/bookstack_indexer.py
@@ -22,6 +22,7 @@ from app.utils.document_converters import (
 from .base import (
     calculate_date_range,
     check_document_by_unique_identifier,
+    check_duplicate_document_by_hash,
     get_connector_by_id,
     get_current_timestamp,
     logger,
@@ -308,6 +309,22 @@ async def index_bookstack_pages(
                         logger.info(f"Successfully updated BookStack page {page_name}")
                         continue
 
+                # Document doesn't exist by unique_identifier_hash
+                # Check if a document with the same content_hash exists (from another connector)
+                with session.no_autoflush:
+                    duplicate_by_content = await check_duplicate_document_by_hash(
+                        session, content_hash
+                    )
+
+                if duplicate_by_content:
+                    logger.info(
+                        f"BookStack page {page_name} already indexed by another connector "
+                        f"(existing document ID: {duplicate_by_content.id}, "
+                        f"type: {duplicate_by_content.document_type}). Skipping."
+                    )
+                    documents_skipped += 1
+                    continue
+
                 # Document doesn't exist - create new one
                 # Generate summary with metadata
                 user_llm = await get_user_long_context_llm(
diff --git a/surfsense_backend/app/tasks/connector_indexers/clickup_indexer.py b/surfsense_backend/app/tasks/connector_indexers/clickup_indexer.py
index e459584f8..887c3e2e5 100644
--- a/surfsense_backend/app/tasks/connector_indexers/clickup_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/clickup_indexer.py
@@ -22,6 +22,7 @@ from app.utils.document_converters import (
 
 from .base import (
     check_document_by_unique_identifier,
+    check_duplicate_document_by_hash,
     get_connector_by_id,
     get_current_timestamp,
     logger,
@@ -302,6 +303,22 @@ async def index_clickup_tasks(
                             )
                             continue
 
+                    # Document doesn't exist by unique_identifier_hash
+                    # Check if a document with the same content_hash exists (from another connector)
+                    with session.no_autoflush:
+                        duplicate_by_content = await check_duplicate_document_by_hash(
+                            session, content_hash
+                        )
+
+                    if duplicate_by_content:
+                        logger.info(
+                            f"ClickUp task {task_name} already indexed by another connector "
+                            f"(existing document ID: {duplicate_by_content.id}, "
+                            f"type: {duplicate_by_content.document_type}). Skipping."
+                        )
+                        documents_skipped += 1
+                        continue
+
                     # Document doesn't exist - create new one
                     # Generate summary with metadata
                     user_llm = await get_user_long_context_llm(
diff --git a/surfsense_backend/app/tasks/connector_indexers/confluence_indexer.py b/surfsense_backend/app/tasks/connector_indexers/confluence_indexer.py
index ddbefafb9..5673839bb 100644
--- a/surfsense_backend/app/tasks/connector_indexers/confluence_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/confluence_indexer.py
@@ -23,6 +23,7 @@ from app.utils.document_converters import (
 from .base import (
     calculate_date_range,
     check_document_by_unique_identifier,
+    check_duplicate_document_by_hash,
     get_connector_by_id,
     get_current_timestamp,
     logger,
@@ -306,6 +307,22 @@ async def index_confluence_pages(
                         )
                         continue
 
+                # Document doesn't exist by unique_identifier_hash
+                # Check if a document with the same content_hash exists (from another connector)
+                with session.no_autoflush:
+                    duplicate_by_content = await check_duplicate_document_by_hash(
+                        session, content_hash
+                    )
+
+                if duplicate_by_content:
+                    logger.info(
+                        f"Confluence page {page_title} already indexed by another connector "
+                        f"(existing document ID: {duplicate_by_content.id}, "
+                        f"type: {duplicate_by_content.document_type}). Skipping."
+                    )
+                    documents_skipped += 1
+                    continue
+
                 # Document doesn't exist - create new one
                 # Generate summary with metadata
                 user_llm = await get_user_long_context_llm(
diff --git a/surfsense_backend/app/tasks/connector_indexers/discord_indexer.py b/surfsense_backend/app/tasks/connector_indexers/discord_indexer.py
index 8f0c76e53..9e401b335 100644
--- a/surfsense_backend/app/tasks/connector_indexers/discord_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/discord_indexer.py
@@ -21,6 +21,7 @@ from app.utils.document_converters import (
 from .base import (
     build_document_metadata_markdown,
     check_document_by_unique_identifier,
+    check_duplicate_document_by_hash,
     get_connector_by_id,
     get_current_timestamp,
     logger,
@@ -454,6 +455,24 @@ async def index_discord_messages(
                                     )
                                     continue
 
+                            # Document doesn't exist by unique_identifier_hash
+                            # Check if a document with the same content_hash exists (from another connector)
+                            with session.no_autoflush:
+                                duplicate_by_content = (
+                                    await check_duplicate_document_by_hash(
+                                        session, content_hash
+                                    )
+                                )
+
+                            if duplicate_by_content:
+                                logger.info(
+                                    f"Discord message {msg_id} in {guild_name}#{channel_name} already indexed by another connector "
+                                    f"(existing document ID: {duplicate_by_content.id}, "
+                                    f"type: {duplicate_by_content.document_type}). Skipping."
+                                )
+                                documents_skipped += 1
+                                continue
+
                             # Document doesn't exist - create new one
                             # Process chunks
                             chunks = await create_document_chunks(
diff --git a/surfsense_backend/app/tasks/connector_indexers/github_indexer.py b/surfsense_backend/app/tasks/connector_indexers/github_indexer.py
index 4a8df4918..fb6989bb9 100644
--- a/surfsense_backend/app/tasks/connector_indexers/github_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/github_indexer.py
@@ -24,6 +24,7 @@ from app.utils.document_converters import (
 
 from .base import (
     check_document_by_unique_identifier,
+    check_duplicate_document_by_hash,
     get_connector_by_id,
     get_current_timestamp,
     logger,
@@ -319,6 +320,21 @@ async def _process_repository_digest(
             # Delete existing document to replace with new one
             await session.delete(existing_document)
             await session.flush()
+    else:
+        # Document doesn't exist by unique_identifier_hash
+        # Check if a document with the same content_hash exists (from another connector)
+        with session.no_autoflush:
+            duplicate_by_content = await check_duplicate_document_by_hash(
+                session, content_hash
+            )
+
+        if duplicate_by_content:
+            logger.info(
+                f"Repository {repo_full_name} already indexed by another connector "
+                f"(existing document ID: {duplicate_by_content.id}, "
+                f"type: {duplicate_by_content.document_type}). Skipping."
+            )
+            return 0
 
     # Generate summary using LLM (ONE call per repository!)
     user_llm = await get_user_long_context_llm(session, user_id, search_space_id)
diff --git a/surfsense_backend/app/tasks/connector_indexers/google_gmail_indexer.py b/surfsense_backend/app/tasks/connector_indexers/google_gmail_indexer.py
index 08d2904d6..e599abd22 100644
--- a/surfsense_backend/app/tasks/connector_indexers/google_gmail_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/google_gmail_indexer.py
@@ -24,7 +24,9 @@ from app.utils.document_converters import (
 )
 
 from .base import (
+    calculate_date_range,
     check_document_by_unique_identifier,
+    check_duplicate_document_by_hash,
     get_connector_by_id,
     get_current_timestamp,
     logger,
@@ -163,10 +165,22 @@ async def index_google_gmail_messages(
             credentials, session, user_id, connector_id
         )
 
+        # Calculate date range using last_indexed_at if dates not provided
+        # This ensures Gmail uses the same date logic as other connectors
+        # (uses last_indexed_at → now, or 365 days back for first-time indexing)
+        calculated_start_date, calculated_end_date = calculate_date_range(
+            connector, start_date, end_date, default_days_back=365
+        )
+
         # Fetch recent Google gmail messages
-        logger.info(f"Fetching recent emails for connector {connector_id}")
+        logger.info(
+            f"Fetching emails for connector {connector_id} "
+            f"from {calculated_start_date} to {calculated_end_date}"
+        )
         messages, error = await gmail_connector.get_recent_messages(
-            max_results=max_messages, start_date=start_date, end_date=end_date
+            max_results=max_messages,
+            start_date=calculated_start_date,
+            end_date=calculated_end_date,
         )
 
         if error:
@@ -316,6 +330,22 @@ async def index_google_gmail_messages(
                         logger.info(f"Successfully updated Gmail message {subject}")
                         continue
 
+                # Document doesn't exist by unique_identifier_hash
+                # Check if a document with the same content_hash exists (from another connector)
+                with session.no_autoflush:
+                    duplicate_by_content = await check_duplicate_document_by_hash(
+                        session, content_hash
+                    )
+
+                if duplicate_by_content:
+                    logger.info(
+                        f"Gmail message {subject} already indexed by another connector "
+                        f"(existing document ID: {duplicate_by_content.id}, "
+                        f"type: {duplicate_by_content.document_type}). Skipping."
+                    )
+                    documents_skipped += 1
+                    continue
+
                 # Document doesn't exist - create new one
                 # Generate summary with metadata
                 user_llm = await get_user_long_context_llm(
diff --git a/surfsense_backend/app/tasks/connector_indexers/jira_indexer.py b/surfsense_backend/app/tasks/connector_indexers/jira_indexer.py
index 4851a6466..d6095d20e 100644
--- a/surfsense_backend/app/tasks/connector_indexers/jira_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/jira_indexer.py
@@ -23,6 +23,7 @@ from app.utils.document_converters import (
 from .base import (
     calculate_date_range,
     check_document_by_unique_identifier,
+    check_duplicate_document_by_hash,
     get_connector_by_id,
     get_current_timestamp,
     logger,
@@ -284,6 +285,22 @@ async def index_jira_issues(
                         )
                         continue
 
+                # Document doesn't exist by unique_identifier_hash
+                # Check if a document with the same content_hash exists (from another connector)
+                with session.no_autoflush:
+                    duplicate_by_content = await check_duplicate_document_by_hash(
+                        session, content_hash
+                    )
+
+                if duplicate_by_content:
+                    logger.info(
+                        f"Jira issue {issue_identifier} already indexed by another connector "
+                        f"(existing document ID: {duplicate_by_content.id}, "
+                        f"type: {duplicate_by_content.document_type}). Skipping."
+                    )
+                    documents_skipped += 1
+                    continue
+
                 # Document doesn't exist - create new one
                 # Generate summary with metadata
                 user_llm = await get_user_long_context_llm(
diff --git a/surfsense_backend/app/tasks/connector_indexers/linear_indexer.py b/surfsense_backend/app/tasks/connector_indexers/linear_indexer.py
index 7d8e0c30e..d00a39160 100644
--- a/surfsense_backend/app/tasks/connector_indexers/linear_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/linear_indexer.py
@@ -22,6 +22,7 @@ from app.utils.document_converters import (
 from .base import (
     calculate_date_range,
     check_document_by_unique_identifier,
+    check_duplicate_document_by_hash,
     get_connector_by_id,
     get_current_timestamp,
     logger,
@@ -315,6 +316,22 @@ async def index_linear_issues(
                         )
                         continue
 
+                # Document doesn't exist by unique_identifier_hash
+                # Check if a document with the same content_hash exists (from another connector)
+                with session.no_autoflush:
+                    duplicate_by_content = await check_duplicate_document_by_hash(
+                        session, content_hash
+                    )
+
+                if duplicate_by_content:
+                    logger.info(
+                        f"Linear issue {issue_identifier} already indexed by another connector "
+                        f"(existing document ID: {duplicate_by_content.id}, "
+                        f"type: {duplicate_by_content.document_type}). Skipping."
+                    )
+                    documents_skipped += 1
+                    continue
+
                 # Document doesn't exist - create new one
                 # Generate summary with metadata
                 user_llm = await get_user_long_context_llm(
diff --git a/surfsense_backend/app/tasks/connector_indexers/luma_indexer.py b/surfsense_backend/app/tasks/connector_indexers/luma_indexer.py
index ead259a44..59890dbe4 100644
--- a/surfsense_backend/app/tasks/connector_indexers/luma_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/luma_indexer.py
@@ -21,6 +21,7 @@ from app.utils.document_converters import (
 
 from .base import (
     check_document_by_unique_identifier,
+    check_duplicate_document_by_hash,
     get_connector_by_id,
     get_current_timestamp,
     logger,
@@ -363,6 +364,22 @@ async def index_luma_events(
                         logger.info(f"Successfully updated Luma event {event_name}")
                         continue
 
+                # Document doesn't exist by unique_identifier_hash
+                # Check if a document with the same content_hash exists (from another connector)
+                with session.no_autoflush:
+                    duplicate_by_content = await check_duplicate_document_by_hash(
+                        session, content_hash
+                    )
+
+                if duplicate_by_content:
+                    logger.info(
+                        f"Luma event {event_name} already indexed by another connector "
+                        f"(existing document ID: {duplicate_by_content.id}, "
+                        f"type: {duplicate_by_content.document_type}). Skipping."
+                    )
+                    documents_skipped += 1
+                    continue
+
                 # Document doesn't exist - create new one
                 # Generate summary with metadata
                 user_llm = await get_user_long_context_llm(
diff --git a/surfsense_backend/app/tasks/connector_indexers/notion_indexer.py b/surfsense_backend/app/tasks/connector_indexers/notion_indexer.py
index 2d36351fa..70c4917da 100644
--- a/surfsense_backend/app/tasks/connector_indexers/notion_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/notion_indexer.py
@@ -22,6 +22,7 @@ from .base import (
     build_document_metadata_string,
     calculate_date_range,
     check_document_by_unique_identifier,
+    check_duplicate_document_by_hash,
     get_connector_by_id,
     get_current_timestamp,
     logger,
@@ -360,6 +361,22 @@ async def index_notion_pages(
 
                         continue
 
+                # Document doesn't exist by unique_identifier_hash
+                # Check if a document with the same content_hash exists (from another connector)
+                with session.no_autoflush:
+                    duplicate_by_content = await check_duplicate_document_by_hash(
+                        session, content_hash
+                    )
+
+                if duplicate_by_content:
+                    logger.info(
+                        f"Notion page {page_title} already indexed by another connector "
+                        f"(existing document ID: {duplicate_by_content.id}, "
+                        f"type: {duplicate_by_content.document_type}). Skipping."
+                    )
+                    documents_skipped += 1
+                    continue
+
                 # Document doesn't exist - create new one
                 # Get user's long context LLM
                 user_llm = await get_user_long_context_llm(
diff --git a/surfsense_backend/app/tasks/connector_indexers/obsidian_indexer.py b/surfsense_backend/app/tasks/connector_indexers/obsidian_indexer.py
index 4c4dab4c2..a603d3fba 100644
--- a/surfsense_backend/app/tasks/connector_indexers/obsidian_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/obsidian_indexer.py
@@ -28,6 +28,7 @@ from app.utils.document_converters import (
 from .base import (
     build_document_metadata_string,
     check_document_by_unique_identifier,
+    check_duplicate_document_by_hash,
     get_connector_by_id,
     get_current_timestamp,
     logger,
@@ -426,6 +427,22 @@ async def index_obsidian_vault(
                     indexed_count += 1
 
                 else:
+                    # Document doesn't exist by unique_identifier_hash
+                    # Check if a document with the same content_hash exists (from another connector)
+                    with session.no_autoflush:
+                        duplicate_by_content = await check_duplicate_document_by_hash(
+                            session, content_hash
+                        )
+
+                    if duplicate_by_content:
+                        logger.info(
+                            f"Obsidian note {title} already indexed by another connector "
+                            f"(existing document ID: {duplicate_by_content.id}, "
+                            f"type: {duplicate_by_content.document_type}). Skipping."
+                        )
+                        skipped_count += 1
+                        continue
+
                     # Create new document
                     logger.info(f"Indexing new note: {title}")
 
diff --git a/surfsense_backend/app/tasks/connector_indexers/slack_indexer.py b/surfsense_backend/app/tasks/connector_indexers/slack_indexer.py
index f6ed4f567..f244c97f8 100644
--- a/surfsense_backend/app/tasks/connector_indexers/slack_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/slack_indexer.py
@@ -22,6 +22,7 @@ from .base import (
     build_document_metadata_markdown,
     calculate_date_range,
     check_document_by_unique_identifier,
+    check_duplicate_document_by_hash,
     get_connector_by_id,
     get_current_timestamp,
     logger,
@@ -325,6 +326,22 @@ async def index_slack_messages(
                             logger.info(f"Successfully updated Slack message {msg_ts}")
                             continue
 
+                    # Document doesn't exist by unique_identifier_hash
+                    # Check if a document with the same content_hash exists (from another connector)
+                    with session.no_autoflush:
+                        duplicate_by_content = await check_duplicate_document_by_hash(
+                            session, content_hash
+                        )
+
+                    if duplicate_by_content:
+                        logger.info(
+                            f"Slack message {msg_ts} in channel {channel_name} already indexed by another connector "
+                            f"(existing document ID: {duplicate_by_content.id}, "
+                            f"type: {duplicate_by_content.document_type}). Skipping."
+                        )
+                        documents_skipped += 1
+                        continue
+
                     # Document doesn't exist - create new one
                     # Process chunks
                     chunks = await create_document_chunks(combined_document_string)
diff --git a/surfsense_backend/app/tasks/connector_indexers/teams_indexer.py b/surfsense_backend/app/tasks/connector_indexers/teams_indexer.py
index b879ddfcb..66b709ddc 100644
--- a/surfsense_backend/app/tasks/connector_indexers/teams_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/teams_indexer.py
@@ -21,6 +21,7 @@ from .base import (
     build_document_metadata_markdown,
     calculate_date_range,
     check_document_by_unique_identifier,
+    check_duplicate_document_by_hash,
     get_connector_by_id,
     get_current_timestamp,
     logger,
@@ -354,6 +355,27 @@ async def index_teams_messages(
                                     )
                                     continue
 
+                            # Document doesn't exist by unique_identifier_hash
+                            # Check if a document with the same content_hash exists (from another connector)
+                            with session.no_autoflush:
+                                duplicate_by_content = (
+                                    await check_duplicate_document_by_hash(
+                                        session, content_hash
+                                    )
+                                )
+
+                            if duplicate_by_content:
+                                logger.info(
+                                    "Teams message %s in channel %s already indexed by another connector "
+                                    "(existing document ID: %s, type: %s). Skipping.",
+                                    message_id,
+                                    channel_name,
+                                    duplicate_by_content.id,
+                                    duplicate_by_content.document_type,
+                                )
+                                documents_skipped += 1
+                                continue
+
                             # Document doesn't exist - create new one
                             # Process chunks
                             chunks = await create_document_chunks(
diff --git a/surfsense_backend/app/tasks/connector_indexers/webcrawler_indexer.py b/surfsense_backend/app/tasks/connector_indexers/webcrawler_indexer.py
index fb1aae5f2..0c63fd2f0 100644
--- a/surfsense_backend/app/tasks/connector_indexers/webcrawler_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/webcrawler_indexer.py
@@ -18,9 +18,11 @@ from app.utils.document_converters import (
     generate_document_summary,
     generate_unique_identifier_hash,
 )
+from app.utils.webcrawler_utils import parse_webcrawler_urls
 
 from .base import (
     check_document_by_unique_identifier,
+    check_duplicate_document_by_hash,
     get_connector_by_id,
     get_current_timestamp,
     logger,
@@ -96,13 +98,7 @@ async def index_crawled_urls(
         api_key = connector.config.get("FIRECRAWL_API_KEY")
 
         # Get URLs from connector config
-        initial_urls = connector.config.get("INITIAL_URLS", "")
-        if isinstance(initial_urls, str):
-            urls = [url.strip() for url in initial_urls.split("\n") if url.strip()]
-        elif isinstance(initial_urls, list):
-            urls = [url.strip() for url in initial_urls if url.strip()]
-        else:
-            urls = []
+        urls = parse_webcrawler_urls(connector.config.get("INITIAL_URLS"))
 
         logger.info(
             f"Starting crawled web page indexing for connector {connector_id} with {len(urls)} URLs"
@@ -281,6 +277,22 @@ async def index_crawled_urls(
                         logger.info(f"Successfully updated URL {url}")
                         continue
 
+                # Document doesn't exist by unique_identifier_hash
+                # Check if a document with the same content_hash exists (from another connector)
+                with session.no_autoflush:
+                    duplicate_by_content = await check_duplicate_document_by_hash(
+                        session, content_hash
+                    )
+
+                if duplicate_by_content:
+                    logger.info(
+                        f"URL {url} already indexed by another connector "
+                        f"(existing document ID: {duplicate_by_content.id}, "
+                        f"type: {duplicate_by_content.document_type}). Skipping."
+                    )
+                    documents_skipped += 1
+                    continue
+
                 # Document doesn't exist - create new one
                 # Generate summary with metadata
                 user_llm = await get_user_long_context_llm(
diff --git a/surfsense_backend/app/tasks/document_processors/file_processors.py b/surfsense_backend/app/tasks/document_processors/file_processors.py
index 5161fb569..6c4be0cb8 100644
--- a/surfsense_backend/app/tasks/document_processors/file_processors.py
+++ b/surfsense_backend/app/tasks/document_processors/file_processors.py
@@ -55,7 +55,9 @@ LLAMACLOUD_RETRYABLE_EXCEPTIONS = (
 )
 
 # Timeout calculation constants
-UPLOAD_BYTES_PER_SECOND_SLOW = 100 * 1024  # 100 KB/s (conservative for slow connections)
+UPLOAD_BYTES_PER_SECOND_SLOW = (
+    100 * 1024
+)  # 100 KB/s (conservative for slow connections)
 MIN_UPLOAD_TIMEOUT = 120  # Minimum 2 minutes for any file
 MAX_UPLOAD_TIMEOUT = 1800  # Maximum 30 minutes for very large files
 BASE_JOB_TIMEOUT = 600  # 10 minutes base for job processing
@@ -219,19 +221,19 @@ async def find_existing_document_with_migration(
 def calculate_upload_timeout(file_size_bytes: int) -> float:
     """
     Calculate appropriate upload timeout based on file size.
-    
+
     Assumes a conservative slow connection speed to handle worst-case scenarios.
-    
+
     Args:
         file_size_bytes: Size of the file in bytes
-        
+
     Returns:
         Timeout in seconds
     """
     # Calculate time needed at slow connection speed
     # Add 50% buffer for network variability and SSL overhead
     estimated_time = (file_size_bytes / UPLOAD_BYTES_PER_SECOND_SLOW) * 1.5
-    
+
     # Clamp to reasonable bounds
     return max(MIN_UPLOAD_TIMEOUT, min(estimated_time, MAX_UPLOAD_TIMEOUT))
 
@@ -239,21 +241,21 @@ def calculate_upload_timeout(file_size_bytes: int) -> float:
 def calculate_job_timeout(estimated_pages: int, file_size_bytes: int) -> float:
     """
     Calculate job processing timeout based on page count and file size.
-    
+
     Args:
         estimated_pages: Estimated number of pages
         file_size_bytes: Size of the file in bytes
-        
+
     Returns:
         Timeout in seconds
     """
     # Base timeout + time per page
     page_based_timeout = BASE_JOB_TIMEOUT + (estimated_pages * PER_PAGE_JOB_TIMEOUT)
-    
+
     # Also consider file size (large images take longer to process)
     # ~1 minute per 10MB of file size
     size_based_timeout = BASE_JOB_TIMEOUT + (file_size_bytes / (10 * 1024 * 1024)) * 60
-    
+
     # Use the larger of the two estimates
     return max(page_based_timeout, size_based_timeout)
 
@@ -284,18 +286,18 @@ async def parse_with_llamacloud_retry(
     """
     import os
     import random
-    
+
     from llama_cloud_services import LlamaParse
     from llama_cloud_services.parse.utils import ResultType
 
     # Get file size for timeout calculations
     file_size_bytes = os.path.getsize(file_path)
     file_size_mb = file_size_bytes / (1024 * 1024)
-    
+
     # Calculate dynamic timeouts based on file size and page count
     upload_timeout = calculate_upload_timeout(file_size_bytes)
     job_timeout = calculate_job_timeout(estimated_pages, file_size_bytes)
-    
+
     # HTTP client timeouts - scaled based on file size
     # Write timeout is critical for large file uploads
     custom_timeout = httpx.Timeout(
@@ -304,7 +306,7 @@ async def parse_with_llamacloud_retry(
         write=upload_timeout,  # Dynamic based on file size (upload time)
         pool=120.0,  # 2 minutes to acquire connection from pool
     )
-    
+
     logging.info(
         f"LlamaCloud upload configured: file_size={file_size_mb:.1f}MB, "
         f"pages={estimated_pages}, upload_timeout={upload_timeout:.0f}s, "
@@ -335,14 +337,14 @@ async def parse_with_llamacloud_retry(
 
                 # Parse the file asynchronously
                 result = await parser.aparse(file_path)
-                
+
                 # Success - log if we had previous failures
                 if attempt > 1:
                     logging.info(
                         f"LlamaCloud upload succeeded on attempt {attempt} after "
                         f"{len(attempt_errors)} failures"
                     )
-                
+
                 return result
 
         except LLAMACLOUD_RETRYABLE_EXCEPTIONS as e:
@@ -355,8 +357,7 @@ async def parse_with_llamacloud_retry(
                 # Calculate exponential backoff with jitter
                 # Base delay doubles each attempt, capped at max delay
                 base_delay = min(
-                    LLAMACLOUD_BASE_DELAY * (2 ** (attempt - 1)),
-                    LLAMACLOUD_MAX_DELAY
+                    LLAMACLOUD_BASE_DELAY * (2 ** (attempt - 1)), LLAMACLOUD_MAX_DELAY
                 )
                 # Add random jitter (±25%) to prevent thundering herd
                 jitter = base_delay * 0.25 * (2 * random.random() - 1)
diff --git a/surfsense_backend/app/utils/periodic_scheduler.py b/surfsense_backend/app/utils/periodic_scheduler.py
index 219641933..aa8c07ce4 100644
--- a/surfsense_backend/app/utils/periodic_scheduler.py
+++ b/surfsense_backend/app/utils/periodic_scheduler.py
@@ -43,6 +43,7 @@ def create_periodic_schedule(
     user_id: str,
     connector_type: SearchSourceConnectorType,
     frequency_minutes: int,
+    connector_config: dict | None = None,
 ) -> bool:
     """
     Trigger the first indexing run immediately when periodic indexing is enabled.
@@ -57,11 +58,26 @@ def create_periodic_schedule(
         user_id: User ID
         connector_type: Type of connector
         frequency_minutes: Frequency in minutes (used for logging)
+        connector_config: Optional connector config dict for validation
 
     Returns:
         True if successful, False otherwise
     """
     try:
+        # Special handling for connectors that require config validation
+        if connector_type == SearchSourceConnectorType.WEBCRAWLER_CONNECTOR:
+            from app.utils.webcrawler_utils import parse_webcrawler_urls
+
+            config = connector_config or {}
+            urls = parse_webcrawler_urls(config.get("INITIAL_URLS"))
+
+            if not urls:
+                logger.info(
+                    f"Webcrawler connector {connector_id} has no URLs configured, "
+                    "skipping first indexing run (will run when URLs are added)"
+                )
+                return True  # Return success - schedule is created, just no first run
+
         logger.info(
             f"Periodic indexing enabled for connector {connector_id} "
             f"(frequency: {frequency_minutes} minutes). Triggering first run..."
diff --git a/surfsense_backend/app/utils/webcrawler_utils.py b/surfsense_backend/app/utils/webcrawler_utils.py
new file mode 100644
index 000000000..31d2ebe50
--- /dev/null
+++ b/surfsense_backend/app/utils/webcrawler_utils.py
@@ -0,0 +1,28 @@
+"""
+Utility functions for webcrawler connector.
+"""
+
+
+def parse_webcrawler_urls(initial_urls: str | list | None) -> list[str]:
+    """
+    Parse URLs from webcrawler INITIAL_URLS value.
+
+    Handles both string (newline-separated) and list formats.
+
+    Args:
+        initial_urls: The INITIAL_URLS value (string, list, or None)
+
+    Returns:
+        List of parsed, stripped, non-empty URLs
+    """
+    if initial_urls is None:
+        return []
+
+    if isinstance(initial_urls, str):
+        return [url.strip() for url in initial_urls.split("\n") if url.strip()]
+    elif isinstance(initial_urls, list):
+        return [
+            url.strip() for url in initial_urls if isinstance(url, str) and url.strip()
+        ]
+    else:
+        return []
diff --git a/surfsense_web/app/dashboard/[search_space_id]/new-chat/[[...chat_id]]/page.tsx b/surfsense_web/app/dashboard/[search_space_id]/new-chat/[[...chat_id]]/page.tsx
index f6f70f83b..1f9dd433d 100644
--- a/surfsense_web/app/dashboard/[search_space_id]/new-chat/[[...chat_id]]/page.tsx
+++ b/surfsense_web/app/dashboard/[search_space_id]/new-chat/[[...chat_id]]/page.tsx
@@ -143,6 +143,7 @@ export default function NewChatPage() {
 	const queryClient = useQueryClient();
 	const [isInitializing, setIsInitializing] = useState(true);
 	const [isCompletingClone, setIsCompletingClone] = useState(false);
+	const [cloneError, setCloneError] = useState(false);
 	const [threadId, setThreadId] = useState<number | null>(null);
 	const [currentThread, setCurrentThread] = useState<ThreadRecord | null>(null);
 	const [messages, setMessages] = useState<ThreadMessageLike[]>([]);
@@ -333,7 +334,7 @@ export default function NewChatPage() {
 
 	// Handle clone completion when thread has clone_pending flag
 	useEffect(() => {
-		if (!currentThread?.clone_pending || isCompletingClone) return;
+		if (!currentThread?.clone_pending || isCompletingClone || cloneError) return;
 
 		const completeClone = async () => {
 			setIsCompletingClone(true);
@@ -351,13 +352,14 @@ export default function NewChatPage() {
 			} catch (error) {
 				console.error("[NewChatPage] Failed to complete clone:", error);
 				toast.error("Failed to copy chat content. Please try again.");
+				setCloneError(true);
 			} finally {
 				setIsCompletingClone(false);
 			}
 		};
 
 		completeClone();
-	}, [currentThread?.clone_pending, currentThread?.id, isCompletingClone, initializeThread, queryClient]);
+	}, [currentThread?.clone_pending, currentThread?.id, isCompletingClone, cloneError, initializeThread, queryClient]);
 
 	// Handle scroll to comment from URL query params (e.g., from inbox item click)
 	const searchParams = useSearchParams();