diff --git a/tools/observer-transcript-parser.mjs b/tools/observer-transcript-parser.mjs
index 198ebc9c..466346eb 100644
--- a/tools/observer-transcript-parser.mjs
+++ b/tools/observer-transcript-parser.mjs
@@ -286,6 +286,29 @@ export function extractTokenUsage(turn) {
   };
 }
 
+/**
+ * For each AskUserQuestion toolUseResult in the turn, emit one event per question.
+ * answer_kind: 'option' (exact label match), 'custom' (free-text), 'no_answer' (missing/empty).
+ */
+export function extractAskUserQuestionEvents(turn) {
+  const events = [];
+  for (const e of turn || []) {
+    const tur = e && e.toolUseResult;
+    if (!tur || !Array.isArray(tur.questions) || !tur.answers) continue;
+    const qCount = tur.questions.length;
+    for (const q of tur.questions) {
+      const labels = (q.options || []).map((o) => o && o.label).filter((l) => typeof l === 'string');
+      const answer = tur.answers[q.question];
+      let answer_kind;
+      if (typeof answer !== 'string' || answer.length === 0) answer_kind = 'no_answer';
+      else if (labels.some((l) => l.trim() === answer.trim())) answer_kind = 'option';
+      else answer_kind = 'custom';
+      events.push({ kind: 'ask_user_question', question_count: qCount, answer_kind });
+    }
+  }
+  return events;
+}
+
 /** Classify the opening user-prompt sentiment (per spec §6 / gap-resolution 1). */
 export function classifyPromptSignal(text) {
   const t = String(text || '').toLowerCase().trim();
@@ -472,6 +495,7 @@ export function parseTranscript(transcriptText, fallbackSessionId = null) {
     events.push({ kind: 'error', message: 'tool_result reported is_error' });
   }
   events.push(...extractProcessEvents(turn, broken, total, durationMs));
+  events.push(...extractAskUserQuestionEvents(turn));
 
   const usedSuperpowers = skills.some((s) => String(s).startsWith(SUPERPOWERS_PREFIX));
   const prompt = promptText(entries[start]);
diff --git a/tools/observer-transcript-parser.test.mjs b/tools/observer-transcript-parser.test.mjs
index 1482030a..c42ed74d 100644
--- a/tools/observer-transcript-parser.test.mjs
+++ b/tools/observer-transcript-parser.test.mjs
@@ -1003,3 +1003,80 @@ describe('parseTranscript — task_cost integration (Task 2)', () => {
     });
   });
 });
+
+import { extractAskUserQuestionEvents } from './observer-transcript-parser.mjs';
+
+describe('extractAskUserQuestionEvents (Task 4)', () => {
+  it('records "option" when user picked an offered label exactly', () => {
+    const turn = [
+      { message: { content: [{ type: 'tool_use', name: 'AskUserQuestion',
+        input: { questions: [{ question: 'q1', options: [{ label: 'A' }, { label: 'B' }] }] } }] } },
+      { toolUseResult: { questions: [{ question: 'q1', options: [{ label: 'A' }, { label: 'B' }] }],
+        answers: { q1: 'A' } } },
+    ];
+    const evs = extractAskUserQuestionEvents(turn);
+    expect(evs).toHaveLength(1);
+    expect(evs[0].kind).toBe('ask_user_question');
+    expect(evs[0].question_count).toBe(1);
+    expect(evs[0].answer_kind).toBe('option');
+  });
+  it('records "custom" when user wrote free-text Other', () => {
+    const turn = [
+      { message: { content: [{ type: 'tool_use', name: 'AskUserQuestion',
+        input: { questions: [{ question: 'q1', options: [{ label: 'A' }, { label: 'B' }] }] } }] } },
+      { toolUseResult: { questions: [{ question: 'q1', options: [{ label: 'A' }, { label: 'B' }] }],
+        answers: { q1: 'C — мой вариант' } } },
+    ];
+    const evs = extractAskUserQuestionEvents(turn);
+    expect(evs[0].answer_kind).toBe('custom');
+  });
+  it('records "no_answer" when answer key missing', () => {
+    const turn = [
+      { toolUseResult: { questions: [{ question: 'q1', options: [{ label: 'A' }, { label: 'B' }] }],
+        answers: {} } },
+    ];
+    const evs = extractAskUserQuestionEvents(turn);
+    expect(evs[0].answer_kind).toBe('no_answer');
+  });
+  it('reports question_count from toolUseResult.questions length', () => {
+    const turn = [
+      { toolUseResult: { questions: [
+          { question: 'q1', options: [{ label: 'A' }] },
+          { question: 'q2', options: [{ label: 'B' }] },
+        ], answers: { q1: 'A', q2: 'B' } } },
+    ];
+    const evs = extractAskUserQuestionEvents(turn);
+    expect(evs).toHaveLength(2);   // one event per question
+    expect(evs[0].question_count).toBe(2);
+    expect(evs[1].question_count).toBe(2);
+  });
+  it('returns empty for a turn without AskUserQuestion', () => {
+    expect(extractAskUserQuestionEvents([{ message: { content: [{ type: 'tool_use', name: 'Read' }] } }])).toEqual([]);
+  });
+  it('handles null/undefined turn safely', () => {
+    expect(extractAskUserQuestionEvents(null)).toEqual([]);
+    expect(extractAskUserQuestionEvents(undefined)).toEqual([]);
+    expect(extractAskUserQuestionEvents([])).toEqual([]);
+  });
+});
+
+describe('parseTranscript — ask_user_question events (Task 4)', () => {
+  it('emits ask_user_question event from AskUserQuestion + toolUseResult', () => {
+    const transcript = [
+      JSON.stringify({ sessionId: 's1' }),
+      JSON.stringify({ type: 'user', message: { role: 'user', content: 'делай' }, uuid: 'u1', timestamp: '2026-05-20T00:00:00Z' }),
+      JSON.stringify({ type: 'assistant', message: { role: 'assistant', content: [
+        { type: 'tool_use', id: 't1', name: 'AskUserQuestion',
+          input: { questions: [{ question: 'q', options: [{ label: 'X' }, { label: 'Y' }] }] } },
+      ] }, uuid: 'u2', timestamp: '2026-05-20T00:00:01Z' }),
+      JSON.stringify({ type: 'user', message: { role: 'user', content: [
+        { type: 'tool_result', tool_use_id: 't1' },
+      ] }, toolUseResult: { questions: [{ question: 'q', options: [{ label: 'X' }, { label: 'Y' }] }],
+        answers: { q: 'X' } }, uuid: 'u3', timestamp: '2026-05-20T00:00:02Z' }),
+    ].join('\n');
+    const ep = parseTranscript(transcript);
+    const aq = ep.events.filter((e) => e.kind === 'ask_user_question');
+    expect(aq).toHaveLength(1);
+    expect(aq[0].answer_kind).toBe('option');
+  });
+});