diff --git a/site/src/pages/AgentsPage/AgentDetail/ConversationTimeline.tsx b/site/src/pages/AgentsPage/AgentDetail/ConversationTimeline.tsx
index 5954ba94e7..62a1010a02 100644
--- a/site/src/pages/AgentsPage/AgentDetail/ConversationTimeline.tsx
+++ b/site/src/pages/AgentsPage/AgentDetail/ConversationTimeline.tsx
@@ -268,7 +268,7 @@ const ChatMessageItem = memo<{
 							</div>
 							{fadeFromBottom && (
 								<div
-									className="pointer-events-none absolute inset-x-0 bottom-0 h-12"
+									className="pointer-events-none absolute inset-x-0 bottom-0 h-1/2 max-h-12"
 									style={{
 										background:
 											"linear-gradient(to top, hsl(var(--surface-secondary)), transparent)",
@@ -400,8 +400,10 @@ const StickyUserMessage: FC<{
 }) => {
 	const [isStuck, setIsStuck] = useState(false);
 	const [isReady, setIsReady] = useState(false);
+	const [isTooTall, setIsTooTall] = useState(false);
 	const sentinelRef = useRef<HTMLDivElement>(null);
 	const containerRef = useRef<HTMLDivElement>(null);
+	const updateFnRef = useRef<(() => void) | null>(null);
 
 	// useLayoutEffect so isStuck and --clip-h are both resolved
 	// before the browser paints, avoiding a flash on load.
@@ -440,9 +442,22 @@ const StickyUserMessage: FC<{
 
 		const MIN_HEIGHT = 72;
 		let scrollerTop = scroller.getBoundingClientRect().top;
+		let scrollerHeight = scroller.clientHeight;
 
 		const update = () => {
 			const fullHeight = container.offsetHeight;
+
+			// Skip sticky behavior for messages that take up
+			// most of the visible area — accounting for the
+			// chat input and some breathing room.
+			const tooTall = fullHeight > scrollerHeight * 0.75;
+			setIsTooTall(tooTall);
+			if (tooTall) {
+				container.style.setProperty("--clip-h", `${fullHeight}px`);
+				container.style.setProperty("--fade-opacity", "0");
+				return;
+			}
+
 			const sentinelTop = sentinel.getBoundingClientRect().top;
 			const scrolledPast = scrollerTop - sentinelTop;
 
@@ -463,9 +478,11 @@ const StickyUserMessage: FC<{
 				visible < fullHeight - 8 ? "1" : "0",
 			);
 		};
+		updateFnRef.current = update;
 
 		const onResize = () => {
 			scrollerTop = scroller.getBoundingClientRect().top;
+			scrollerHeight = scroller.clientHeight;
 			update();
 		};
 
@@ -495,6 +512,16 @@ const StickyUserMessage: FC<{
 		};
 	}, []);
 
+	// Re-run the height calculation synchronously whenever
+	// isStuck changes so --clip-h is correct on the same frame
+	// the overlay appears. Without this, the async
+	// IntersectionObserver + RAF-throttled scroll handler can
+	// leave a stale --clip-h for one paint.
+	// biome-ignore lint/correctness/useExhaustiveDependencies: isStuck is an intentional trigger
+	useLayoutEffect(() => {
+		updateFnRef.current?.();
+	}, [isStuck]);
+
 	const handleEditUserMessage = onEditUserMessage
 		? (messageId: number, text: string) => {
 				onEditUserMessage(messageId, text);
@@ -519,18 +546,19 @@ const StickyUserMessage: FC<{
 			<div
 				ref={containerRef}
 				className={cn(
-					"relative sticky top-0 z-10 px-3 -mx-3 pt-2 pb-2",
+					"relative px-3 -mx-3 pt-2 pb-2",
+					!isTooTall && "sticky top-0 z-10",
 					!isReady && "invisible",
-					isStuck && "pointer-events-none",
+					isStuck && !isTooTall && "pointer-events-none",
 				)}
 			>
 				{/* Flow element: always in the DOM to preserve
 				    scroll layout. Hidden when stuck so the
 				    clipped overlay takes over visually. */}
 				<div
-					className={isStuck ? undefined : "pointer-events-auto"}
+					className={isStuck && !isTooTall ? undefined : "pointer-events-auto"}
 					style={
-						isStuck
+						isStuck && !isTooTall
 							? { opacity: "calc(1 - var(--overlay-ready, 0))" }
 							: undefined
 					}
@@ -548,7 +576,7 @@ const StickyUserMessage: FC<{
 				    sticky container. max-height + mask are driven
 				    entirely by the --clip-h CSS variable which the
 				    scroll handler sets on the container. */}
-				{isStuck && (
+				{isStuck && !isTooTall && (
 					<div
 						className="absolute inset-0"
 						style={{
diff --git a/site/src/pages/AgentsPage/FilesChangedPanel.tsx b/site/src/pages/AgentsPage/FilesChangedPanel.tsx
index e7021aa1bf..645bdc6182 100644
--- a/site/src/pages/AgentsPage/FilesChangedPanel.tsx
+++ b/site/src/pages/AgentsPage/FilesChangedPanel.tsx
@@ -40,7 +40,15 @@ function formatPullRequestLabel(url: string): string {
 export const FilesChangedPanel: FC<FilesChangedPanelProps> = ({ chatId }) => {
 	const theme = useTheme();
 	const isDark = theme.palette.mode === "dark";
-	const diffOptions = useMemo(() => getDiffViewerOptions(isDark), [isDark]);
+	const diffOptions = useMemo(() => {
+		const base = getDiffViewerOptions(isDark);
+		return {
+			...base,
+			// Extend the base CSS to make file headers sticky so they
+			// remain visible while scrolling through long diffs.
+			unsafeCSS: `${base.unsafeCSS ?? ""} [data-diffs-header] { position: sticky; top: 0; z-index: 10; background-color: hsl(var(--surface-primary)) !important; }`,
+		};
+	}, [isDark]);
 
 	const diffStatusQuery = useQuery(chatDiffStatus(chatId));
 	const diffContentsQuery = useQuery({
diff --git a/site/vite.config.mts b/site/vite.config.mts
index bdf392465d..824f222367 100644
--- a/site/vite.config.mts
+++ b/site/vite.config.mts
@@ -90,6 +90,14 @@ export default defineConfig({
 				target: process.env.CODER_HOST || "http://localhost:3000",
 				secure: process.env.NODE_ENV === "production",
 				configure: (proxy) => {
+					if (process.env.CODER_SESSION_TOKEN) {
+						proxy.on("proxyReq", (proxyReq) => {
+							proxyReq.setHeader(
+								"Coder-Session-Token",
+								process.env.CODER_SESSION_TOKEN!,
+							);
+						});
+					}
 					// Vite does not catch socket errors, and stops the webserver.
 					// As /logs endpoint can return HTTP 4xx status, we need to embrace
 					// Vite with a custom error handler to prevent from quitting.