diff --git a/apps/web/src/components/ChatView.logic.test.ts b/apps/web/src/components/ChatView.logic.test.ts
index 8aa4df4c09ba5..c241522084415 100644
--- a/apps/web/src/components/ChatView.logic.test.ts
+++ b/apps/web/src/components/ChatView.logic.test.ts
@@ -4,6 +4,7 @@ import {
   buildExpiredTerminalContextToastCopy,
   mergeDirectPreviewAnnotation,
   planComposerTurn,
+  deriveTimelineWorking,
   snapshotComposerSend,
   withMessageContext,
   deriveAvailableRevertTurnCounts,
@@ -45,6 +46,7 @@ import { appAtomRegistry } from "../rpc/atomRegistry";
 import { environmentThreadDetails } from "../state/threads";
 
 import type { Thread } from "../types";
+import { derivePhase } from "../session-logic";
 import { makeThreadFixture, makeThreadProjectionFixture } from "../test-fixtures";
 import {
   getAntigravitySendBlockReason,
@@ -1129,6 +1131,28 @@ describe("snapshotComposerSend", () => {
   });
 });
 
+describe("deriveTimelineWorking", () => {
+  it.each(["preparing", "starting", "queued"] as const)(
+    "restores activity from a persisted %s session without a local send",
+    (status) => {
+      const state = {
+        phase: derivePhase({ ...readySession, status }),
+        isSendBusy: false,
+        isCompacting: false,
+        runlessWorkStartedAt: null,
+      };
+      expect(deriveTimelineWorking(state)).toBe(true);
+      expect(deriveTimelineWorking({ ...state, phase: "ready" })).toBe(false);
+      expect(
+        deriveTimelineWorking({
+          ...state,
+          phase: derivePhase({ ...readySession, status: "failed" }),
+        }),
+      ).toBe(false);
+    },
+  );
+});
+
 describe("planComposerTurn", () => {
   const base = {
     messageText: "hello",
diff --git a/apps/web/src/components/ChatView.logic.ts b/apps/web/src/components/ChatView.logic.ts
index d98ab2ac9bd67..14590bb0ff386 100644
--- a/apps/web/src/components/ChatView.logic.ts
+++ b/apps/web/src/components/ChatView.logic.ts
@@ -1294,6 +1294,22 @@ export function snapshotComposerSend(contents: ComposerSendContents) {
 
 export type ComposerSendSnapshot = ReturnType<typeof snapshotComposerSend>;
 
+/** Derived from the persisted run phase, so a starting run still reads as work after a reload. */
+export function deriveTimelineWorking(input: {
+  readonly phase: SessionPhase;
+  readonly isSendBusy: boolean;
+  readonly isCompacting: boolean;
+  readonly runlessWorkStartedAt: string | null;
+}): boolean {
+  return (
+    input.phase === "connecting" ||
+    input.phase === "running" ||
+    input.isSendBusy ||
+    input.isCompacting ||
+    input.runlessWorkStartedAt !== null
+  );
+}
+
 /** How a composer send dispatches: where it runs and whether it waits behind other work. */
 export function planComposerTurn(input: {
   readonly messageText: string;
diff --git a/apps/web/src/components/ChatView.tsx b/apps/web/src/components/ChatView.tsx
index 7da579d0659aa..764ea2c6bf756 100644
--- a/apps/web/src/components/ChatView.tsx
+++ b/apps/web/src/components/ChatView.tsx
@@ -350,6 +350,7 @@ import {
 import {
   buildLocalDraftThread,
   deriveCommittedServerUserMessageIds,
+  deriveTimelineWorking,
   dismissBranchMismatchForSession,
   shouldRenderPreviewMiniPlayer,
   deriveLockedProvider,
@@ -1495,8 +1496,12 @@ export default function ChatView(props: ChatViewProps) {
     run: serverProjection?.runs.find((run) => run.id === activeRuntime?.activeRunId),
     messages: serverProjection?.messages,
   });
-  const isWorking =
-    phase === "running" || isSendBusy || isCompacting || runlessWorkStartedAt !== null;
+  const isWorking = deriveTimelineWorking({
+    phase,
+    isSendBusy,
+    isCompacting,
+    runlessWorkStartedAt,
+  });
   const activeContextWindow = deriveLatestContextWindowSnapshot(
     serverVisibleTurnItems ?? [],
     activeThreadLiveTokenUsage,