diff --git a/site/src/api/queries/chats.ts b/site/src/api/queries/chats.ts
index fead88a404..366255e4c5 100644
--- a/site/src/api/queries/chats.ts
+++ b/site/src/api/queries/chats.ts
@@ -453,7 +453,13 @@ export const unpinChat = (queryClient: QueryClient) => ({
 export const reorderPinnedChat = (queryClient: QueryClient) => ({
 	mutationFn: ({ chatId, pinOrder }: { chatId: string; pinOrder: number }) =>
 		API.experimental.updateChat(chatId, { pin_order: pinOrder }),
-	onMutate: async ({ chatId }: { chatId: string; pinOrder: number }) => {
+	onMutate: async ({
+		chatId,
+		pinOrder,
+	}: {
+		chatId: string;
+		pinOrder: number;
+	}) => {
 		await queryClient.cancelQueries({
 			queryKey: chatsKey,
 			predicate: isChatListQuery,
@@ -462,6 +468,26 @@ export const reorderPinnedChat = (queryClient: QueryClient) => ({
 			queryKey: chatKey(chatId),
 			exact: true,
 		});
+
+		// Optimistically reorder pinned chats in the cache so the
+		// sidebar reflects the new order immediately without waiting
+		// for the server round-trip.
+		const allChats = readInfiniteChatsCache(queryClient) ?? [];
+		const pinned = allChats
+			.filter((c) => c.pin_order > 0)
+			.sort((a, b) => a.pin_order - b.pin_order);
+		const oldIdx = pinned.findIndex((c) => c.id === chatId);
+		if (oldIdx !== -1) {
+			const moved = pinned.splice(oldIdx, 1)[0];
+			pinned.splice(pinOrder - 1, 0, moved);
+			const newOrders = new Map(pinned.map((c, i) => [c.id, i + 1]));
+			updateInfiniteChatsCache(queryClient, (chats) =>
+				chats.map((c) => {
+					const order = newOrders.get(c.id);
+					return order !== undefined ? { ...c, pin_order: order } : c;
+				}),
+			);
+		}
 	},
 	onSettled: async (
 		_data: unknown,
diff --git a/site/src/pages/AgentsPage/components/Sidebar/AgentsSidebar.tsx b/site/src/pages/AgentsPage/components/Sidebar/AgentsSidebar.tsx
index cc811a8c8c..331e55597a 100644
--- a/site/src/pages/AgentsPage/components/Sidebar/AgentsSidebar.tsx
+++ b/site/src/pages/AgentsPage/components/Sidebar/AgentsSidebar.tsx
@@ -672,8 +672,7 @@ const ChatTreeNode: FC<ChatTreeNodeProps> = ({ chat, isChildNode }) => {
 
 const SortableChatTreeNode: FC<{
 	chat: Chat;
-	recentDragRef: React.RefObject<boolean>;
-}> = ({ chat, recentDragRef }) => {
+}> = ({ chat }) => {
 	const {
 		attributes,
 		listeners,
@@ -707,18 +706,6 @@ const SortableChatTreeNode: FC<{
 			className={cn(isDragging && "opacity-50")}
 			{...attributes}
 			{...listeners}
-			onClickCapture={(e) => {
-				// After a drag, the browser synthesizes a click from
-				// pointerup. dnd-kit's sensor calls stopPropagation
-				// but never preventDefault, so the <a> tag inside
-				// NavLink still fires its default navigation action.
-				// Block it here in React's capture phase instead of
-				// racing with a global document listener + rAF.
-				if (recentDragRef.current) {
-					e.stopPropagation();
-					e.preventDefault();
-				}
-			}}
 		>
 			<ChatTreeNode chat={chat} isChildNode={false} />
 		</div>
@@ -807,11 +794,25 @@ export const AgentsSidebar: FC<AgentsSidebarProps> = (props) => {
 
 	const pinnedChatIds = sortedPinnedChats.map((chat) => chat.id);
 
-	// Ref flag set after drag ends. Checked by SortableChatTreeNode's
-	// onClickCapture to block the synthetic click that the browser
-	// fires from the final pointerup. Cleared after 100ms, which
-	// comfortably exceeds dnd-kit's 50ms sensor cleanup window.
-	const recentDragRef = useRef(false);
+	const lastDragEndedAtRef = useRef(0);
+
+	const pinnedContainerRef = useRef<HTMLDivElement | null>(null);
+	useEffect(() => {
+		const handler = (e: MouseEvent) => {
+			const container = pinnedContainerRef.current;
+			const target = e.target;
+			if (
+				container &&
+				target instanceof Node &&
+				container.contains(target) &&
+				performance.now() - lastDragEndedAtRef.current < 300
+			) {
+				e.preventDefault();
+			}
+		};
+		document.addEventListener("click", handler, true);
+		return () => document.removeEventListener("click", handler, true);
+	}, []);
 
 	const sensors = useSensors(
 		useSensor(MouseSensor, {
@@ -828,11 +829,7 @@ export const AgentsSidebar: FC<AgentsSidebarProps> = (props) => {
 	const handleDragEnd = (event: DragEndEvent) => {
 		const { active, over } = event;
 
-		recentDragRef.current = true;
-		setTimeout(() => {
-			recentDragRef.current = false;
-		}, 100);
-
+		lastDragEndedAtRef.current = performance.now();
 		if (!over || active.id === over.id) return;
 		const activeId = String(active.id);
 		const overId = String(over.id);
@@ -1087,12 +1084,14 @@ export const AgentsSidebar: FC<AgentsSidebarProps> = (props) => {
 																items={pinnedChatIds}
 																strategy={verticalListSortingStrategy}
 															>
-																<div className="flex flex-col gap-0.5">
+																<div
+																	ref={pinnedContainerRef}
+																	className="flex flex-col gap-0.5"
+																>
 																	{sortedPinnedChats.map((chat) => (
 																		<SortableChatTreeNode
 																			key={chat.id}
 																			chat={chat}
-																			recentDragRef={recentDragRef}
 																		/>
 																	))}
 																</div>