diff --git a/site/src/pages/AgentsPage/components/Sidebar/AgentsSidebar.test.tsx b/site/src/pages/AgentsPage/components/Sidebar/AgentsSidebar.test.tsx
index 92f21f0136..d761efd2cc 100644
--- a/site/src/pages/AgentsPage/components/Sidebar/AgentsSidebar.test.tsx
+++ b/site/src/pages/AgentsPage/components/Sidebar/AgentsSidebar.test.tsx
@@ -258,6 +258,50 @@ describe("AgentsSidebar load-more behavior", () => {
 		expect(onLoadMore).toHaveBeenCalledTimes(1);
 	});
 
+	it("recreates the observer when isFetchingNextPage transitions to false so visible sentinels re-trigger", () => {
+		const onLoadMore = vi.fn();
+		const { rerender } = render(
+			<Wrapper>
+				<AgentsSidebar
+					{...defaultProps}
+					hasNextPage
+					onLoadMore={onLoadMore}
+					isFetchingNextPage={false}
+				/>
+			</Wrapper>,
+		);
+
+		const countAfterMount = observeCount;
+		expect(countAfterMount).toBe(1);
+
+		// Start fetching — observer is torn down.
+		rerender(
+			<Wrapper>
+				<AgentsSidebar
+					{...defaultProps}
+					hasNextPage
+					onLoadMore={onLoadMore}
+					isFetchingNextPage={true}
+				/>
+			</Wrapper>,
+		);
+
+		// Fetch completes — a fresh observer is created, firing
+		// an initial entry that detects the still-visible sentinel.
+		rerender(
+			<Wrapper>
+				<AgentsSidebar
+					{...defaultProps}
+					hasNextPage
+					onLoadMore={onLoadMore}
+					isFetchingNextPage={false}
+				/>
+			</Wrapper>,
+		);
+
+		expect(observeCount).toBe(countAfterMount + 1);
+	});
+
 	it("does NOT render the sentinel when hasNextPage is false", () => {
 		const onLoadMore = vi.fn();
 		render(
diff --git a/site/src/pages/AgentsPage/components/Sidebar/AgentsSidebar.tsx b/site/src/pages/AgentsPage/components/Sidebar/AgentsSidebar.tsx
index 2dd13a9181..6841ac9d12 100644
--- a/site/src/pages/AgentsPage/components/Sidebar/AgentsSidebar.tsx
+++ b/site/src/pages/AgentsPage/components/Sidebar/AgentsSidebar.tsx
@@ -1131,27 +1131,29 @@ const LoadMoreSentinel: FC<{
 }> = ({ onLoadMore, isFetchingNextPage }) => {
 	const sentinelRef = useRef<HTMLDivElement>(null);
 	const onLoadMoreRef = useRef(onLoadMore);
-	const isFetchingNextPageRef = useRef(isFetchingNextPage);
 
-	// Keep refs in sync with the latest prop values so the
-	// observer callback always reads current state without
-	// needing to tear down and re-create the observer.
+	// Keep the callback ref in sync so the observer closure
+	// always calls the latest onLoadMore without needing to
+	// tear down and re-create the observer.
 	useEffect(() => {
 		onLoadMoreRef.current = onLoadMore;
-		isFetchingNextPageRef.current = isFetchingNextPage;
-	}, [onLoadMore, isFetchingNextPage]);
+	}, [onLoadMore]);
 
 	useEffect(() => {
+		// Don't observe while a fetch is in progress. When the
+		// fetch completes this effect re-runs, creating a fresh
+		// observer whose initial entry detects the sentinel if
+		// it's still visible — fixing the case where loaded items
+		// don't push the sentinel out of view and the previous
+		// observer never re-fires.
+		if (isFetchingNextPage) return;
+
 		const el = sentinelRef.current;
 		if (!el) return;
 
 		const observer = new IntersectionObserver(
 			(entries) => {
-				if (
-					entries[0]?.isIntersecting &&
-					!isFetchingNextPageRef.current &&
-					onLoadMoreRef.current
-				) {
+				if (entries[0]?.isIntersecting && onLoadMoreRef.current) {
 					onLoadMoreRef.current();
 				}
 			},
@@ -1159,7 +1161,7 @@ const LoadMoreSentinel: FC<{
 		);
 		observer.observe(el);
 		return () => observer.disconnect();
-	}, []);
+	}, [isFetchingNextPage]);
 
 	return (
 		<div ref={sentinelRef} className="flex items-center justify-center py-2">