diff --git a/test/helpers/claude-pty-runner.ts b/test/helpers/claude-pty-runner.ts
index 02d6a30e5..36b2efb1a 100644
--- a/test/helpers/claude-pty-runner.ts
+++ b/test/helpers/claude-pty-runner.ts
@@ -504,6 +504,9 @@ ${tail}
  *     for plan-eng / plan-design / plan-devex prose AUQ
  *   - 3+ distinct numbered options (1. 2. 3.) at line starts WITHOUT a
  *     `❯<spaces>1.` cursor — typical for autoplan / office-hours prose AUQ
+ *   - 3+ markdown bold-bullet options (`- **label**`) following an
+ *     interrogative line — office-hours renders its mode question this way
+ *     (`> - **Building a startup**`), which has no letter/number marker
  *
  * Used by classifyVisible and runPlanSkillFloorCheck to return outcome='asked'
  * (or auq_observed) instead of letting the harness time out when the model
@@ -547,7 +550,24 @@ export function isProseAUQVisible(visible: string): boolean {
   while ((nm = numberedRe.exec(tail)) !== null) {
     if (nm[1]) numberedHits.add(nm[1]);
   }
-  return numberedHits.size >= 2;
+  if (numberedHits.size >= 2) return true;
+
+  // Pattern 3: markdown bold-bullet option list. office-hours renders its
+  // mode question as `> - **Building a startup**` lines under
+  // --disallowedTools — no letter/number marker, so Patterns 1-2 miss it,
+  // and the model keeps a spinner up so the Haiku judge scores it 'working'
+  // and the run times out despite the question being on screen.
+  // Require both: an interrogative line (the question stem ends in '?') AND
+  // 3+ bold-bullet markers. The bold (`- **`) requirement is what separates
+  // an option list from incidental prose bullets; the line anchor is dropped
+  // because stripAnsi can collapse option lines (see Pattern 1 note), so we
+  // count markers anywhere in the tail. The `❯ 1.` cursor gate above already
+  // excludes a live native list.
+  if (/\?/.test(tail)) {
+    const boldBulletHits = (tail.match(/[-*•]\s+\*\*/g) || []).length;
+    if (boldBulletHits >= 3) return true;
+  }
+  return false;
 }
 
 /**
diff --git a/test/helpers/claude-pty-runner.unit.test.ts b/test/helpers/claude-pty-runner.unit.test.ts
index 345c95f47..a42e12583 100644
--- a/test/helpers/claude-pty-runner.unit.test.ts
+++ b/test/helpers/claude-pty-runner.unit.test.ts
@@ -291,6 +291,64 @@ This refers to (see option B) above and also to point A) earlier.
     expect(isProseAUQVisible('Just some plain text output from the model.')).toBe(false);
     expect(isProseAUQVisible('')).toBe(false);
   });
+
+  // Pattern 3: markdown bold-bullet options — office-hours renders its mode
+  // question this way under --disallowedTools, with no letter/number marker.
+  test('matches office-hours markdown bold-bullet mode question (Pattern 3)', () => {
+    const sample = `
+> Before we dig in — what's your goal with this?
+>
+> - **Building a startup** (or thinking about it)
+> - **Intrapreneurship** — internal project at a company, need to ship fast
+> - **Hackathon / demo** — time-boxed, need to impress
+> - **Open source / research** — building for a community
+> - **Learning** — teaching yourself to code
+❯
+`;
+    expect(isProseAUQVisible(sample)).toBe(true);
+  });
+
+  test('bold-bullets require a preceding interrogative — no "?" => false', () => {
+    // 3+ bold bullets but no question stem: this is a feature list, not an AUQ.
+    const sample = `
+Here is what shipped:
+- **Faster builds** via caching
+- **Smaller binaries** through tree-shaking
+- **Better errors** with source maps
+`;
+    expect(isProseAUQVisible(sample)).toBe(false);
+  });
+
+  test('a question with fewer than 3 bold bullets stays false (guard)', () => {
+    const sample = `
+Which approach do you prefer?
+- **Option one** is simpler
+- **Option two** is faster
+`;
+    expect(isProseAUQVisible(sample)).toBe(false);
+  });
+
+  test('plain (non-bold) bullets after a question do not trigger Pattern 3', () => {
+    // Only bold bullets count — plain "- text" prose lists are too common.
+    const sample = `
+What should we do about this?
+- run the tests
+- ship the fix
+- file a follow-up
+`;
+    expect(isProseAUQVisible(sample)).toBe(false);
+  });
+
+  test('Pattern 3 still defers to a live native cursor list (❯ 1.)', () => {
+    const sample = `
+> What's your goal?
+❯ 1. **Building a startup**
+  2. **Intrapreneurship**
+  3. **Hackathon**
+`;
+    // The ❯1. cursor gate fires first — native list handling owns this.
+    expect(isProseAUQVisible(sample)).toBe(false);
+  });
 });
 
 describe('classifyVisible (runtime path through the runner classifier)', () => {