diff --git a/apps/web/src/components/chat/MessagesTimeline.test.tsx b/apps/web/src/components/chat/MessagesTimeline.test.tsx
index 4c7cf29969d9..6ef0f38808ca 100644
--- a/apps/web/src/components/chat/MessagesTimeline.test.tsx
+++ b/apps/web/src/components/chat/MessagesTimeline.test.tsx
@@ -135,6 +135,8 @@ function matchMedia() {
 }
 
 let MessagesTimeline: typeof import("./MessagesTimeline").MessagesTimeline;
+let resolveTimelineStatusRowPinned: typeof import("./MessagesTimeline").resolveTimelineStatusRowPinned;
+let resolveTimelineStatusRowTopOffset: typeof import("./MessagesTimeline").resolveTimelineStatusRowTopOffset;
 
 beforeAll(async () => {
   const classList = {
@@ -168,7 +170,8 @@ beforeAll(async () => {
     },
   });
 
-  ({ MessagesTimeline } = await import("./MessagesTimeline"));
+  ({ MessagesTimeline, resolveTimelineStatusRowPinned, resolveTimelineStatusRowTopOffset } =
+    await import("./MessagesTimeline"));
 }, 30_000);
 
 const ACTIVE_THREAD_ENVIRONMENT_ID = EnvironmentId.make("environment-local");
@@ -330,6 +333,28 @@ describe("MessagesTimeline", () => {
     expect(markup).toContain("px-1 text-sm leading-relaxed text-muted-foreground");
   });
 
+  it("pins a keyed status row when later rows follow it", () => {
+    const state = {
+      scroll: 100,
+      positionByKey: (key: string) => (key === "working-indicator-row" ? 112 : undefined),
+    };
+
+    expect(resolveTimelineStatusRowPinned(state, "working-indicator-row", 12)).toBe(true);
+    expect(
+      resolveTimelineStatusRowPinned({ ...state, scroll: 99 }, "working-indicator-row", 12),
+    ).toBe(false);
+    expect(resolveTimelineStatusRowPinned({ scroll: 100 }, "working-indicator-row", 12)).toBe(
+      false,
+    );
+  });
+
+  it("matches the timeline header height at each breakpoint", () => {
+    expect(resolveTimelineStatusRowTopOffset(false, false)).toBe(12);
+    expect(resolveTimelineStatusRowTopOffset(false, true)).toBe(16);
+    expect(resolveTimelineStatusRowTopOffset(true, false)).toBe(40);
+    expect(resolveTimelineStatusRowTopOffset(true, true)).toBe(48);
+  });
+
   it("uses the larger leading inset only when the top fade is enabled", () => {
     const timelineEntries = [buildUserTimelineEntry("Hello")];
 
diff --git a/apps/web/src/components/chat/MessagesTimeline.tsx b/apps/web/src/components/chat/MessagesTimeline.tsx
index dc0c03709e6c..98d33e5ba2ee 100644
--- a/apps/web/src/components/chat/MessagesTimeline.tsx
+++ b/apps/web/src/components/chat/MessagesTimeline.tsx
@@ -103,6 +103,7 @@ import {
 } from "./MessagesTimeline.logic";
 import { TerminalContextInlineChip } from "./TerminalContextInlineChip";
 import { Tooltip, TooltipPopup, TooltipTrigger } from "../ui/tooltip";
+import { useMediaQuery } from "~/hooks/useMediaQuery";
 import {
   deriveDisplayedUserMessageState,
   type ParsedTerminalContextEntry,
@@ -444,9 +445,15 @@ export const MessagesTimeline = memo(function MessagesTimeline({
   );
   const rows = useStableRows(rawRows);
   const minimapItems = useMemo(() => deriveTimelineMinimapItems(rows), [rows]);
+  const stickyStatusRow = isWorking
+    ? rows.find((row) => row.kind === "working")
+    : rows.find((row) => row.kind === "turn-fold" && row.turnId === latestTurn?.turnId);
   const [timelineViewportElement, setTimelineViewportElement] = useState<HTMLDivElement | null>(
     null,
   );
+  const [statusRowPinned, setStatusRowPinned] = useState(false);
+  const isWideViewport = useMediaQuery("sm");
+  const statusRowTop = resolveTimelineStatusRowTopOffset(topFadeEnabled, isWideViewport);
   const [minimapHasPersistentGutter, setMinimapHasPersistentGutter] = useState(false);
   const [minimapHitStripWidth, setMinimapHitStripWidth] = useState(0);
   const handleAnchorReady = useCallback(
@@ -470,11 +477,19 @@ export const MessagesTimeline = memo(function MessagesTimeline({
     if (isAtEnd !== undefined) {
       onIsAtEndChange(isAtEnd);
     }
-    if (!state || minimapItems.length === 0) {
+    if (!state) {
       return;
     }
 
     const scrollTop = state.scroll ?? 0;
+    setStatusRowPinned(
+      stickyStatusRow !== undefined &&
+        resolveTimelineStatusRowPinned(state, stickyStatusRow.id, statusRowTop),
+    );
+    if (minimapItems.length === 0) {
+      return;
+    }
+
     const scrollBottom = scrollTop + (state.scrollLength ?? 0);
 
     for (const item of minimapItems) {
@@ -492,7 +507,15 @@ export const MessagesTimeline = memo(function MessagesTimeline({
 
       strip.dataset.inView = inView ? "true" : "false";
     }
-  }, [contentInsetEndAdjustment, listRef, minimapItems, minimapStripMap, onIsAtEndChange]);
+  }, [
+    contentInsetEndAdjustment,
+    listRef,
+    minimapItems,
+    minimapStripMap,
+    onIsAtEndChange,
+    stickyStatusRow,
+    statusRowTop,
+  ]);
 
   useEffect(() => {
     const frame = requestAnimationFrame(handleScroll);
@@ -633,6 +656,23 @@ export const MessagesTimeline = memo(function MessagesTimeline({
             }
             ListFooterComponent={TIMELINE_LIST_FOOTER}
           />
+          {statusRowPinned && stickyStatusRow ? (
+            <div
+              className="pointer-events-none absolute inset-x-0 z-10 px-3 sm:px-5"
+              data-turn-status-row-pinned="true"
+              style={{ top: statusRowTop }}
+            >
+              <div
+                aria-hidden={stickyStatusRow.kind === "working" || undefined}
+                className={cn(
+                  "mx-auto w-full min-w-0 max-w-3xl overflow-x-clip bg-background",
+                  stickyStatusRow.kind === "turn-fold" && "pointer-events-auto",
+                )}
+              >
+                <TimelineRowContent row={stickyStatusRow} />
+              </div>
+            </div>
+          ) : null}
           <TimelineMinimap
             items={minimapItems}
             hasPersistentGutter={minimapHasPersistentGutter}
@@ -670,6 +710,7 @@ interface TimelineMinimapItem {
 
 interface TimelinePositionState {
   readonly contentLength?: number;
+  readonly positionByKey?: (key: string) => number | undefined;
   readonly scroll?: number;
   readonly scrollLength?: number;
   readonly positionAtIndex?: (index: number) => number | undefined;
@@ -726,6 +767,23 @@ function resolveTimelineRowTop(state: TimelinePositionState, rowIndex: number) {
   return typeof top === "number" && Number.isFinite(top) ? top : null;
 }
 
+export function resolveTimelineStatusRowPinned(
+  state: TimelinePositionState,
+  rowKey: string,
+  statusRowTop: number,
+) {
+  const rowTop = state.positionByKey?.(rowKey);
+  return (
+    typeof rowTop === "number" &&
+    Number.isFinite(rowTop) &&
+    rowTop <= (state.scroll ?? 0) + statusRowTop
+  );
+}
+
+export function resolveTimelineStatusRowTopOffset(topFadeEnabled: boolean, isWide: boolean) {
+  return topFadeEnabled ? (isWide ? 48 : 40) : isWide ? 16 : 12;
+}
+
 function resolveTimelineRowHeight(state: TimelinePositionState, rowIndex: number) {
   const height = state.sizeAtIndex?.(rowIndex);
   return typeof height === "number" && Number.isFinite(height) ? height : null;
@@ -971,6 +1029,7 @@ const TimelineRowContent = memo(function TimelineRowContent({ row }: { row: Time
                   row.kind === "turn-plan"
                 ? "pb-2"
                 : "pb-4",
+        row.kind === "turn-fold" || row.kind === "working" ? "bg-background" : null,
         row.kind === "message" && row.message.role === "assistant" ? "group/assistant" : null,
       )}
       data-timeline-row-id={row.id}