diff --git a/packages/app/src/agent-stream/strategy-web.tsx b/packages/app/src/agent-stream/strategy-web.tsx
index bc6966b18..7f31539e1 100644
--- a/packages/app/src/agent-stream/strategy-web.tsx
+++ b/packages/app/src/agent-stream/strategy-web.tsx
@@ -331,9 +331,7 @@ function WebStreamViewport(props: StreamRenderInput & { isMobileBreakpoint: bool
         settleFrames: HISTORY_START_SETTLE_FRAMES,
         requestFrame: (callback) => window.requestAnimationFrame(callback),
         cancelFrame: (frame) => window.cancelAnimationFrame(frame),
-        isSettling: () =>
-          historyStartPaginationStateRef.current.status === "settling" &&
-          historyStartPrependAnchorActiveRef.current,
+        isSettling: () => historyStartPaginationStateRef.current.status === "settling",
         isLoading: () => {
           const input = getHistoryStartPaginationInput();
           return (
@@ -581,11 +579,15 @@ function WebStreamViewport(props: StreamRenderInput & { isMobileBreakpoint: bool
   useEffect(() => {
     updateScrollMetrics();
     evaluateHistoryStart();
+    if (historyStartPaginationStateRef.current.status === "settling") {
+      scheduleHistoryStartPrependSettle();
+    }
   }, [
     evaluateHistoryStart,
     hasOlderHistory,
     isLoadingOlderHistory,
     olderHistoryProgressKey,
+    scheduleHistoryStartPrependSettle,
     segments.historyMounted.length,
     segments.historyVirtualized.length,
     segments.liveHead.length,
@@ -605,6 +607,8 @@ function WebStreamViewport(props: StreamRenderInput & { isMobileBreakpoint: bool
     const observer = new ResizeObserver(() => {
       if (historyStartPrependAnchorActiveRef.current) {
         applyHistoryStartPrependAnchor();
+      }
+      if (historyStartPaginationStateRef.current.status === "settling") {
         scheduleHistoryStartPrependSettle();
       }
       updateScrollMetrics();
diff --git a/packages/app/src/timeline/session-stream-reducers.test.ts b/packages/app/src/timeline/session-stream-reducers.test.ts
index 1fad0845a..a549571f4 100644
--- a/packages/app/src/timeline/session-stream-reducers.test.ts
+++ b/packages/app/src/timeline/session-stream-reducers.test.ts
@@ -363,6 +363,59 @@ describe("processTimelineResponse", () => {
     expect(result.head).toEqual([liveThought, liveAssistant]);
   });
 
+  it("keeps a newer live tool completion when bootstrap contains the running call", () => {
+    const callId = "toolu_live_completion";
+    const liveCompletion = hydrateStreamState(
+      [
+        {
+          event: {
+            type: "timeline",
+            provider: "claude",
+            item: makeToolCallTimelineEntry(2, callId, "completed", {
+              type: "read",
+              filePath: "/tmp/example.ts",
+            }).item,
+          } as AgentStreamEventPayload,
+          timestamp: new Date(2000),
+          timelineCursor: { epoch: "epoch-1", seq: 2 },
+        },
+      ],
+      { source: "canonical" },
+    );
+
+    const result = processTimelineResponse({
+      ...baseTimelineInput,
+      currentHead: liveCompletion,
+      hasAuthoritativeBaseline: false,
+      isInitializing: true,
+      hasActiveInitDeferred: true,
+      payload: {
+        ...baseTimelineInput.payload,
+        direction: "tail",
+        reset: false,
+        epoch: "epoch-1",
+        startCursor: { seq: 1 },
+        endCursor: { seq: 1 },
+        entries: [
+          makeToolCallTimelineEntry(1, callId, "running", {
+            type: "unknown",
+            input: { file_path: "/tmp/example.ts" },
+            output: null,
+          }),
+        ],
+      },
+    });
+
+    expect(getAgentToolCalls([...result.tail, ...result.head])).toEqual([
+      expect.objectContaining({
+        timelineCursor: { epoch: "epoch-1", seq: 2 },
+        payload: expect.objectContaining({
+          data: expect.objectContaining({ callId, status: "completed" }),
+        }),
+      }),
+    ]);
+  });
+
   it("replaces a painted replica with an empty authoritative timeline", () => {
     const result = processTimelineResponse({
       ...baseTimelineInput,
diff --git a/packages/app/src/types/stream.ts b/packages/app/src/types/stream.ts
index 5f47bdd70..05f42c6fb 100644
--- a/packages/app/src/types/stream.ts
+++ b/packages/app/src/types/stream.ts
@@ -410,6 +410,44 @@ function removeUserMessageAt(items: UserMessageItem[], index: number): UserMessa
   return [...items.slice(0, index), ...items.slice(index + 1)];
 }
 
+function reconcileReplacementHeadAgainstTail(
+  tail: StreamItem[],
+  retainedHead: StreamItem[],
+): { tail: StreamItem[]; head: StreamItem[] } {
+  let reconciledTail = tail;
+  const reconciledHeadIndexes = new Set<number>();
+  for (const [headIndex, item] of retainedHead.entries()) {
+    if (!isAgentToolCallItem(item) || !item.timelineCursor) {
+      continue;
+    }
+    const tailIndex = findExistingAgentToolCallIndex(reconciledTail, item.payload.data.callId);
+    const existing = reconciledTail[tailIndex];
+    if (tailIndex < 0 || !existing || !isAgentToolCallItem(existing)) {
+      continue;
+    }
+    if (reconciledTail === tail) {
+      reconciledTail = [...tail];
+    }
+    reconciledTail[tailIndex] = mergeAgentToolCallItem(
+      existing,
+      item.payload.data,
+      item.timestamp,
+      item.timelineCursor,
+    );
+    reconciledHeadIndexes.add(headIndex);
+  }
+
+  const tailIds = new Set(reconciledTail.map((item) => item.id));
+  return {
+    tail: reconciledTail,
+    head: retainedHead.filter(
+      (item, index) =>
+        !reconciledHeadIndexes.has(index) &&
+        (item.kind === "assistant_message" || !tailIds.has(item.id)),
+    ),
+  };
+}
+
 function preserveReplacementHead(
   tail: StreamItem[],
   currentHead: StreamItem[],
@@ -435,25 +473,25 @@ function preserveReplacementHead(
           item.clientMessageId !== undefined &&
           sendingClientMessageIds.has(item.clientMessageId),
       );
-  const tailIds = new Set(tail.map((item) => item.id));
-  const unreconciledHead = retainedHead.filter(
-    (item) => item.kind === "assistant_message" || !tailIds.has(item.id),
+  const { tail: reconciledTail, head: unreconciledHead } = reconcileReplacementHeadAgainstTail(
+    tail,
+    retainedHead,
   );
   const liveAssistantIndex = unreconciledHead.findLastIndex(
     (item) => item.kind === "assistant_message",
   );
   if (liveAssistantIndex < 0) {
-    return { tail, head: unreconciledHead, acknowledgedClientMessageIds: [] };
+    return { tail: reconciledTail, head: unreconciledHead, acknowledgedClientMessageIds: [] };
   }
 
   const liveAssistant = unreconciledHead[liveAssistantIndex];
-  const tailAssistant = tail.at(-1);
+  const tailAssistant = reconciledTail.at(-1);
   if (
     liveAssistant.kind !== "assistant_message" ||
     !tailAssistant ||
     tailAssistant.kind !== "assistant_message"
   ) {
-    return { tail, head: unreconciledHead, acknowledgedClientMessageIds: [] };
+    return { tail: reconciledTail, head: unreconciledHead, acknowledgedClientMessageIds: [] };
   }
 
   const isNewerContinuation =
@@ -472,10 +510,14 @@ function preserveReplacementHead(
       { ...liveAssistant, text },
       ...unreconciledHead.slice(liveAssistantIndex + 1),
     ];
-    return { tail: tail.slice(0, -1), head, acknowledgedClientMessageIds: [] };
+    return {
+      tail: reconciledTail.slice(0, -1),
+      head,
+      acknowledgedClientMessageIds: [],
+    };
   }
   if (!liveAssistant.text.startsWith(tailAssistant.text)) {
-    return { tail, head: unreconciledHead, acknowledgedClientMessageIds: [] };
+    return { tail: reconciledTail, head: unreconciledHead, acknowledgedClientMessageIds: [] };
   }
 
   const head = [
@@ -483,7 +525,11 @@ function preserveReplacementHead(
     { ...liveAssistant, text: tailAssistant.text },
     ...unreconciledHead.slice(liveAssistantIndex + 1),
   ];
-  return { tail: tail.slice(0, -1), head, acknowledgedClientMessageIds: [] };
+  return {
+    tail: reconciledTail.slice(0, -1),
+    head,
+    acknowledgedClientMessageIds: [],
+  };
 }
 
 export function replaceWithCanonicalStream(