diff --git a/apps/web/src/components/chat/TimelineWorkGroupRows.tsx b/apps/web/src/components/chat/TimelineWorkGroupRows.tsx
index 2adbd81bd155e..c9a5541897e29 100644
--- a/apps/web/src/components/chat/TimelineWorkGroupRows.tsx
+++ b/apps/web/src/components/chat/TimelineWorkGroupRows.tsx
@@ -892,6 +892,12 @@ function WorkingWindowView({ window, itemKey }: { window: WorkingWindow; itemKey
   }
   const windowRef = useRef<HTMLDivElement>(null);
   const spacerRef = useRef<HTMLDivElement>(null);
+  const [collapseClips, setCollapseClips] = useState(false);
+  // oxlint-disable-next-line t3code/no-unreasoned-state-sync -- reads the expanded height before the collapse transition paints its first frame
+  useLayoutEffect(() => {
+    if (open) return;
+    setCollapseClips((windowRef.current?.scrollHeight ?? 0) > WORKING_WINDOW_COLLAPSED_HEIGHT);
+  }, [open]);
   // oxlint-disable-next-line t3code/no-unreasoned-state-sync -- older items stay mounted until the collapse transition finishes clipping them
   useEffect(() => {
     if (open || history === null) return;
@@ -964,6 +970,7 @@ function WorkingWindowView({ window, itemKey }: { window: WorkingWindow; itemKey
           open
             ? "[height:calc-size(auto,size)]"
             : "[height:calc-size(auto,min(size,220px))] not-supports-[height:calc-size(auto,size)]:max-h-[220px]",
+          !open && history !== null && collapseClips && "working-window-collapse-fade",
         )}
       >
         {history === null ? (
@@ -1027,6 +1034,7 @@ function CollapsedWorkingWindow({
     );
     const content = contentRef.current;
     if (!viewport || !content) return;
+    viewport.scrollTop = viewport.scrollHeight;
     return observeResize([content, viewport], () => {
       if (followRef.current) viewport.scrollTop = viewport.scrollHeight;
     });
@@ -1101,6 +1109,7 @@ function workingWindowItemIsLive(item: WorkingWindowItem | undefined): boolean {
 }
 
 const WORKING_WINDOW_TAIL = 12;
+const WORKING_WINDOW_COLLAPSED_HEIGHT = 220;
 
 const WORKING_HISTORY_BATCH = 50;
 
diff --git a/apps/web/src/index.css b/apps/web/src/index.css
index 3e7c41b9d9783..4927b8ee8d6b9 100644
--- a/apps/web/src/index.css
+++ b/apps/web/src/index.css
@@ -1155,6 +1155,11 @@ html[data-mobile-composer-route-transition="true"]::view-transition-old(t3-mobil
     var(--app-scrollbar-width) 100%;
 }
 
+@utility working-window-collapse-fade {
+  -webkit-mask-image: linear-gradient(to bottom, transparent 0.5rem, black 2rem);
+  mask-image: linear-gradient(to bottom, transparent 0.5rem, black 2rem);
+}
+
 /* Stage-channel art needs a mask and pseudo-element gradient, so keep the
    behavior composable without tying it to the global components layer. */
 @utility sidebar-stage-backdrop {