diff --git a/surfsense_backend/app/indexing_pipeline/indexing_pipeline_service.py b/surfsense_backend/app/indexing_pipeline/indexing_pipeline_service.py
index 2e82dc68c..0fa4006f5 100644
--- a/surfsense_backend/app/indexing_pipeline/indexing_pipeline_service.py
+++ b/surfsense_backend/app/indexing_pipeline/indexing_pipeline_service.py
@@ -273,17 +273,18 @@ class IndexingPipelineService:
                         continue
 
                     dup_check = await self.session.execute(
-                        select(Document.id).filter(
+                        select(Document.id, Document.title).filter(
                             Document.content_hash == content_hash,
                             Document.id != existing.id,
                         )
                     )
-                    if dup_check.scalars().first() is not None:
+                    dup_row = dup_check.first()
+                    if dup_row is not None:
                         if not DocumentStatus.is_state(
                             existing.status, DocumentStatus.READY
                         ):
                             existing.status = DocumentStatus.failed(
-                                "Duplicate content — already indexed by another document"
+                                f"Duplicate content: matches '{dup_row.title}'"
                             )
                         continue
 
diff --git a/surfsense_web/app/dashboard/[search_space_id]/documents/(manage)/components/DocumentsTableShell.tsx b/surfsense_web/app/dashboard/[search_space_id]/documents/(manage)/components/DocumentsTableShell.tsx
index bc17949f5..4ed451850 100644
--- a/surfsense_web/app/dashboard/[search_space_id]/documents/(manage)/components/DocumentsTableShell.tsx
+++ b/surfsense_web/app/dashboard/[search_space_id]/documents/(manage)/components/DocumentsTableShell.tsx
@@ -90,7 +90,7 @@ function StatusIndicator({ status }: { status?: DocumentStatus }) {
 							<Clock className="h-5 w-5 text-muted-foreground/60" />
 						</div>
 					</TooltipTrigger>
-					<TooltipContent side="top">Pending - waiting to be synced</TooltipContent>
+					<TooltipContent side="top">Pending: waiting to be synced</TooltipContent>
 				</Tooltip>
 			);
 		case "processing":
diff --git a/surfsense_web/components/documents/DocumentNode.tsx b/surfsense_web/components/documents/DocumentNode.tsx
index d8e37df1c..0a361fc2b 100644
--- a/surfsense_web/components/documents/DocumentNode.tsx
+++ b/surfsense_web/components/documents/DocumentNode.tsx
@@ -167,7 +167,7 @@ export const DocumentNode = React.memo(function DocumentNode({
 											<Clock className="h-3.5 w-3.5 text-muted-foreground/60" />
 										</span>
 									</TooltipTrigger>
-									<TooltipContent side="top">Pending — waiting to be synced</TooltipContent>
+									<TooltipContent side="top">Pending: waiting to be synced</TooltipContent>
 								</Tooltip>
 							);
 						}
@@ -191,9 +191,9 @@ export const DocumentNode = React.memo(function DocumentNode({
 											<AlertCircle className="h-3.5 w-3.5 text-destructive" />
 										</span>
 									</TooltipTrigger>
-									<TooltipContent side="top" className="max-w-xs">
-										{doc.status?.reason || "Processing failed"}
-									</TooltipContent>
+								<TooltipContent side="top">
+									{doc.status?.reason || "Processing failed"}
+								</TooltipContent>
 								</Tooltip>
 							);
 						}