diff --git a/apps/web/src/components/chat/MessagesTimeline.browser.test.tsx b/apps/web/src/components/chat/MessagesTimeline.browser.test.tsx
index 038274b274b5a..d65d49b9fa6ca 100644
--- a/apps/web/src/components/chat/MessagesTimeline.browser.test.tsx
+++ b/apps/web/src/components/chat/MessagesTimeline.browser.test.tsx
@@ -449,6 +449,57 @@ describe("MessagesTimeline work rows", () => {
       .toBeInTheDocument();
   });
 
+  it("keeps the bar still when work arrives while the history collapses at the bottom", async () => {
+    const runId = RunId.make("collapse-run");
+    const props = {
+      ...baseProps(),
+      isWorking: true,
+      activeTurnStartedAt: CREATED_AT,
+      latestRun: { runId, status: "running" as const, startedAt: CREATED_AT, completedAt: null },
+    };
+    const entries = (steps: number) => [
+      ...Array.from({ length: 40 }, (_, index) =>
+        message(`Earlier ${index}`, {}, `earlier-${index}`),
+      ),
+      message("Build it", { runId }),
+      ...Array.from({ length: steps }, (_, index) =>
+        message(`Step ${index}`, { runId, role: "assistant" }, `step-${index}`),
+      ),
+    ];
+    await using screen = await renderElement(
+      <MessagesTimeline {...props} timelineEntries={entries(30)} />,
+    );
+    const bar = screen.getByRole("button", { name: "Open work history" });
+    await expect.element(bar).toBeVisible();
+    const viewport = props.listRef.current!.getScrollableNode()!;
+    await vi.waitFor(() =>
+      expect(viewport.scrollHeight - viewport.clientHeight - viewport.scrollTop).toBeLessThan(2),
+    );
+    const barElement = bar.element();
+    await bar.click();
+    const history = screen.getByRole("region", { name: "Work history" }).element();
+    await expect.element(screen.getByText("Step 0", { exact: true })).toBeInTheDocument();
+    await Promise.all(history.getAnimations().map((animation) => animation.finished));
+    const barTop = barElement.getBoundingClientRect().top;
+    const expandedHeight = history.clientHeight;
+    const barTops = new Set<number>();
+    const resizes = new ResizeObserver(() => barTops.add(barElement.getBoundingClientRect().top));
+    resizes.observe(history);
+    using _resizes = { [Symbol.dispose]: () => resizes.disconnect() };
+    history.style.transitionDuration = "10s";
+
+    await screen.getByRole("button", { name: "Close work history" }).click();
+    await vi.waitFor(() => expect(history.clientHeight).toBeLessThan(expandedHeight - 20));
+    await screen.rerender(<MessagesTimeline {...props} timelineEntries={entries(31)} />);
+    const arrivedHeight = history.clientHeight;
+    await vi.waitFor(() => expect(history.clientHeight).toBeLessThan(arrivedHeight - 60));
+    for (const animation of history.getAnimations()) animation.finish();
+    await vi.waitFor(() =>
+      expect(history.querySelector('[data-slot="scroll-area-viewport"]')).not.toBeNull(),
+    );
+    expect([...barTops]).toEqual([barTop]);
+  });
+
   it.each(["delegated", "legacy", "missing"] as const)(
     "uses the reported task for %s completion notifications",
     async (source) => {
diff --git a/apps/web/src/components/chat/MessagesTimeline.tsx b/apps/web/src/components/chat/MessagesTimeline.tsx
index b56a533012d1e..f3f212f9639aa 100644
--- a/apps/web/src/components/chat/MessagesTimeline.tsx
+++ b/apps/web/src/components/chat/MessagesTimeline.tsx
@@ -499,6 +499,7 @@ const ConversationTimeline = memo(function ConversationTimeline({
   // The open history belongs to the prompt that opened it; sending closes it.
   const [workingHistoryKey, setWorkingHistoryKey] = useState<string | null>(null);
   const [disclosureToggleSettling, setDisclosureToggleSettling] = useState(false);
+  const [workingHistoryCollapsing, setWorkingHistoryCollapsing] = useState(false);
   const disclosureAnchorKeyRef = useRef<string | null>(null);
   const disclosureSettleFrameRef = useRef<number | null>(null);
   const disclosureSettleSecondFrameRef = useRef<number | null>(null);
@@ -1137,6 +1138,7 @@ const ConversationTimeline = memo(function ConversationTimeline({
     onWorktreeSetupWorkLocally: onWorktreeSetupWorkLocally ?? null,
     onOpenWorktreeSetupTerminal: onOpenWorktreeSetupTerminal ?? null,
     onToggleWorkingHistory,
+    onWorkingHistoryCollapsing: setWorkingHistoryCollapsing,
     onFocusComposer: onFocusComposer ?? null,
     workGroupViewState,
   };
@@ -1431,7 +1433,8 @@ const ConversationTimeline = memo(function ConversationTimeline({
                 !liveFollowEnabled ||
                 fullscreenAppRowId !== null ||
                 disclosureToggleSettling ||
-                workingHistoryOpen
+                workingHistoryOpen ||
+                workingHistoryCollapsing
                   ? false
                   : isWorking && !prefersReducedMotion && settlingListIdentity === null
                     ? TIMELINE_MAINTAIN_SCROLL_AT_END_SMOOTH
diff --git a/apps/web/src/components/chat/TimelineWorkGroupRows.tsx b/apps/web/src/components/chat/TimelineWorkGroupRows.tsx
index 9c4933f318307..3dc64599a0351 100644
--- a/apps/web/src/components/chat/TimelineWorkGroupRows.tsx
+++ b/apps/web/src/components/chat/TimelineWorkGroupRows.tsx
@@ -898,17 +898,20 @@ function WorkingWindowView({ window, itemKey }: { window: WorkingWindow; itemKey
     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
+  const { onWorkingHistoryCollapsing } = ctx;
+  // oxlint-disable-next-line t3code/no-unreasoned-state-sync -- older items stay mounted, and the timeline stops following its end, until the collapse transition finishes
   useEffect(() => {
     if (open || history === null) return;
+    onWorkingHistoryCollapsing(true);
     let cancelled = false;
     void transitionsSettled(windowRef.current).then(() => {
       if (!cancelled) setHistory(null);
     });
     return () => {
       cancelled = true;
+      onWorkingHistoryCollapsing(false);
     };
-  }, [open, history]);
+  }, [open, history, onWorkingHistoryCollapsing]);
   const head = history?.head;
   // oxlint-disable-next-line t3code/no-unreasoned-state-sync -- mounts older items as the timeline scroll brings them near the viewport
   useEffect(() => {
diff --git a/apps/web/src/components/chat/timelineRowContext.ts b/apps/web/src/components/chat/timelineRowContext.ts
index e557e41856c5c..7ba464f4c7848 100644
--- a/apps/web/src/components/chat/timelineRowContext.ts
+++ b/apps/web/src/components/chat/timelineRowContext.ts
@@ -95,6 +95,7 @@ export interface TimelineRowSharedState {
   onWorktreeSetupWorkLocally: (() => void) | null;
   onOpenWorktreeSetupTerminal: ((terminalId: string) => void) | null;
   onToggleWorkingHistory: (key: string) => void;
+  onWorkingHistoryCollapsing: (collapsing: boolean) => void;
   onFocusComposer: (() => void) | null;
   workGroupViewState: WorkGroupViewState;
 }