diff --git a/apps/web/src/pages/workspace/index.tsx b/apps/web/src/pages/workspace/index.tsx
index 63372a47..cbda015d 100644
--- a/apps/web/src/pages/workspace/index.tsx
+++ b/apps/web/src/pages/workspace/index.tsx
@@ -89,6 +89,7 @@ import {
 } from "./tab-follow.ts";
 import {
   awaitingCommit,
+  awaitingReply,
   committedSteps,
   emptyLiveRun,
   foldLiveRun,
@@ -998,19 +999,19 @@ export function StageWorkspace({
     }
   };
   const held = waitingOnPerson(waits, openApprovalIds, runId, liveRun.running);
-  // A message sent here waits on the coordinator from the moment it leaves, before the stream
-  // reports its run: until a reply follows it or a run ends after it.
-  const awaitingReply =
-    awaitingSince !== null &&
-    turns.at(-1)?.role === "person" &&
-    (liveRun.endedAt === null || liveRun.endedAt < awaitingSince) &&
+  const awaiting =
+    awaitingReply(
+      awaitingSince,
+      turns.at(-1)?.role,
+      liveRun.endedAt,
+      parkedOnApproval(waits, openApprovalIds, runId),
+    ) &&
     !archived &&
     startFault === null &&
     modelNeeded === null;
   // The mark stays for the whole turn: between model calls and during long tool work the live
   // reply shows nothing moving.
-  const thinking =
-    !sendFailed && (sending || awaitingReply || (working && !held));
+  const thinking = !sendFailed && (sending || awaiting || (working && !held));
   // Each concept's option is its own tab beside the others, never an ordinary document.
   const options = artifacts.filter((item) => item.kind === DESIGN_OPTION);
   const paneDeliverables = documentsForPane(
diff --git a/apps/web/src/pages/workspace/live-run.ts b/apps/web/src/pages/workspace/live-run.ts
index c24ef242..0fbaea85 100644
--- a/apps/web/src/pages/workspace/live-run.ts
+++ b/apps/web/src/pages/workspace/live-run.ts
@@ -294,3 +294,23 @@ export function waitingOnPerson(
     )
   );
 }
+
+/**
+ * A message sent here waits on the coordinator from the moment it leaves, before the stream
+ * reports its run: until a reply follows it, a run ends after it, or its run is held on an open
+ * approval. An approval card alone brings no reply text while its run stays open. A standing
+ * question does not end the wait: an answer to it is sent before the stream reports the new run.
+ */
+export function awaitingReply(
+  sentAt: number | null,
+  lastTurnRole: ConversationTurn["role"] | undefined,
+  runEndedAt: number | null,
+  heldOnApproval: boolean,
+): boolean {
+  return (
+    sentAt !== null &&
+    lastTurnRole === "person" &&
+    (runEndedAt === null || runEndedAt < sentAt) &&
+    !heldOnApproval
+  );
+}
diff --git a/apps/web/src/pages/workspace/transcript.test.tsx b/apps/web/src/pages/workspace/transcript.test.tsx
index 95122f98..233bf286 100644
--- a/apps/web/src/pages/workspace/transcript.test.tsx
+++ b/apps/web/src/pages/workspace/transcript.test.tsx
@@ -9,6 +9,7 @@ import { wording } from "../../config.ts";
 import { DocumentDecision } from "./document-decision.tsx";
 import {
   awaitingCommit,
+  awaitingReply,
   emptyLiveRun,
   foldLiveRun,
   liveTurnStreaming,
@@ -171,6 +172,23 @@ describe("conversation transcript", () => {
     );
   });
 
+  test("a sent message waits on the coordinator until its approval card opens, and through an answered question", () => {
+    const approval = { runId: "run-c", approvalId: "appr-1" };
+    const question = { runId: "run-c", park: { seq: 4 } };
+    const heldOnCard = parkedOnApproval(
+      [approval],
+      new Set(["appr-1"]),
+      "run-c",
+    );
+    expect(awaitingReply(10, "person", null, false)).toBe(true);
+    expect(awaitingReply(10, "person", null, heldOnCard)).toBe(false);
+    expect(awaitingReply(10, "assistant", null, false)).toBe(false);
+    expect(awaitingReply(10, "person", 12, false)).toBe(false);
+    // The answer is sent while the question still stands and before the stream reports the run.
+    const answered = parkedOnApproval([question], new Set(), "run-c");
+    expect(awaitingReply(20, "person", 12, answered)).toBe(true);
+  });
+
   test("an inference call that finishes with tool work settles even while the message run stays open on a park", () => {
     const started = foldLiveRun(
       emptyLiveRun,