diff --git a/surfsense_web/components/assistant-ui/inline-mention-editor.tsx b/surfsense_web/components/assistant-ui/inline-mention-editor.tsx
index f35019216..917660cf6 100644
--- a/surfsense_web/components/assistant-ui/inline-mention-editor.tsx
+++ b/surfsense_web/components/assistant-ui/inline-mention-editor.tsx
@@ -12,6 +12,7 @@ import {
 } from "react";
 import ReactDOMServer from "react-dom/server";
 import type { Document } from "@/contracts/types/document.types";
+import { getConnectorIcon } from "@/contracts/enums/connectorIcons";
 import { cn } from "@/lib/utils";
 
 export interface MentionedDocument {
@@ -166,12 +167,19 @@ export const InlineMentionEditor = forwardRef<InlineMentionEditorRef, InlineMent
 				chip.setAttribute(CHIP_DOCTYPE_ATTR, doc.document_type ?? "UNKNOWN");
 				chip.contentEditable = "false";
 				chip.className =
-					"inline-flex items-center gap-0.5 mx-0.5 pl-1 pr-0.5 py-0.5 rounded bg-primary/10 text-xs font-bold text-primary border border-primary/10 select-none";
+					"inline-flex items-center gap-1 mx-0.5 pl-1 pr-0.5 py-0.5 rounded bg-primary/10 text-xs font-bold text-primary border border-primary/10 select-none";
 				chip.style.userSelect = "none";
 				chip.style.verticalAlign = "baseline";
 
+				// Add document type icon
+				const iconSpan = document.createElement("span");
+				iconSpan.className = "shrink-0 flex items-center text-muted-foreground";
+				iconSpan.innerHTML = ReactDOMServer.renderToString(
+					getConnectorIcon(doc.document_type ?? "UNKNOWN", "h-3 w-3")
+				);
+
 				const titleSpan = document.createElement("span");
-				titleSpan.className = "max-w-[80px] truncate";
+				titleSpan.className = "max-w-[120px] truncate";
 				titleSpan.textContent = doc.title;
 				titleSpan.title = doc.title;
 
@@ -197,6 +205,7 @@ export const InlineMentionEditor = forwardRef<InlineMentionEditorRef, InlineMent
 					focusAtEnd();
 				};
 
+				chip.appendChild(iconSpan);
 				chip.appendChild(titleSpan);
 				chip.appendChild(removeBtn);
 
diff --git a/surfsense_web/components/new-chat/document-mention-picker.tsx b/surfsense_web/components/new-chat/document-mention-picker.tsx
index 81c7b9a33..5b23f4432 100644
--- a/surfsense_web/components/new-chat/document-mention-picker.tsx
+++ b/surfsense_web/components/new-chat/document-mention-picker.tsx
@@ -156,7 +156,7 @@ export const DocumentMentionPicker = forwardRef<
 	// Use the new lightweight endpoint for document title search
 	// TanStack Query provides signal for automatic request cancellation
 	// keepPreviousData: shows old results while fetching new ones (no spinner flicker)
-	const { data: titleSearchResults, isLoading: isTitleSearchLoading } = useQuery({
+	const { data: titleSearchResults, isLoading: isTitleSearchLoading, isFetching: isTitleSearchFetching } = useQuery({
 		queryKey: ["document-titles", titleSearchParams],
 		queryFn: ({ signal }) =>
 			documentsApiService.searchDocumentTitles({ queryParams: titleSearchParams }, signal),
@@ -168,7 +168,7 @@ export const DocumentMentionPicker = forwardRef<
 	// Use query for fetching first page of SurfSense docs
 	// TanStack Query provides signal for automatic request cancellation
 	// keepPreviousData: shows old results while fetching new ones (no spinner flicker)
-	const { data: surfsenseDocs, isLoading: isSurfsenseDocsLoading } = useQuery({
+	const { data: surfsenseDocs, isLoading: isSurfsenseDocsLoading, isFetching: isSurfsenseDocsFetching } = useQuery({
 		queryKey: ["surfsense-docs-mention", debouncedSearch, isSearchValid],
 		queryFn: ({ signal }) =>
 			documentsApiService.getSurfsenseDocs({ queryParams: surfsenseDocsQueryParams }, signal),
@@ -177,6 +177,16 @@ export const DocumentMentionPicker = forwardRef<
 		placeholderData: keepPreviousData,
 	});
 
+	// Client-side filter to verify search term is actually in the title (handles backend fuzzy false positives)
+	const filterBySearchTerm = useCallback(
+		(docs: Pick<Document, "id" | "title" | "document_type">[]) => {
+			if (!isSearchValid) return docs; // No filtering when not searching
+			const searchLower = debouncedSearch.trim().toLowerCase();
+			return docs.filter((doc) => doc.title.toLowerCase().includes(searchLower));
+		},
+		[debouncedSearch, isSearchValid]
+	);
+
 	// Update accumulated documents when first page loads - combine both sources
 	useEffect(() => {
 		if (currentPage === 0) {
@@ -199,9 +209,10 @@ export const DocumentMentionPicker = forwardRef<
 				setHasMore(titleSearchResults.has_more);
 			}
 
-			setAccumulatedDocuments(combinedDocs);
+			// Apply client-side filter to remove fuzzy false positives
+			setAccumulatedDocuments(filterBySearchTerm(combinedDocs));
 		}
-	}, [titleSearchResults, surfsenseDocs, currentPage]);
+	}, [titleSearchResults, surfsenseDocs, currentPage, filterBySearchTerm]);
 
 	// Function to load next page using lightweight endpoint
 	const loadNextPage = useCallback(async () => {
@@ -246,10 +257,14 @@ export const DocumentMentionPicker = forwardRef<
 
 	const actualDocuments = accumulatedDocuments;
 	const actualLoading = (isTitleSearchLoading || isSurfsenseDocsLoading) && currentPage === 0;
+	const isFetchingResults = isTitleSearchFetching || isSurfsenseDocsFetching;
 
 	// Show hint when search is too short
 	const showSearchHint = shouldSearch && !isSearchValid;
 
+	// Hide popup entirely when user is searching and no documents match (only after fetch completes)
+	const hasNoSearchResults = isSearchValid && !actualLoading && !isFetchingResults && actualDocuments.length === 0;
+
 	// Split documents into SurfSense docs and user docs for grouped rendering
 	const surfsenseDocsList = useMemo(
 		() => actualDocuments.filter((doc) => doc.document_type === "SURFSENSE_DOCS"),
@@ -345,6 +360,11 @@ export const DocumentMentionPicker = forwardRef<
 		[selectableDocuments, highlightedIndex, handleSelectDocument, onDone]
 	);
 
+	// Don't show popup when user is searching and no documents match
+	if (hasNoSearchResults) {
+		return null;
+	}
+
 	return (
 		<div
 			className="flex flex-col w-[280px] sm:w-[320px] bg-popover rounded-lg"