Fix false autonomous safety handoffs

tests/conversation-automation.test.ts

@@ -107,7 +107,7 @@ describe('conversation automation', () => {
     expect((await service.processConversation(incoming(1)))?.remainingTurns).toBe(2);
     const second = await service.processConversation(incoming(2));
 
-    expect(second).toMatchObject({ kind: 'human-required', remainingTurns: 0 });
+    expect(second).toMatchObject({ kind: 'human-required', remainingTurns: 2 });
     expect(chat.sendChatMessage).toHaveBeenCalledOnce();
     expect(getSaved()?.automation).toMatchObject({ turnsUsed: 1, status: 'human-required' });
     expect(getSaved()?.automation.aiMessageFingerprints).toHaveLength(1);
@@ -135,7 +135,7 @@ describe('conversation automation', () => {
 
     const result = await fixture.service.processConversation(conversation);
 
-    expect(result).toMatchObject({ kind: 'human-required', remainingTurns: 0 });
+    expect(result).toMatchObject({ kind: 'human-required', remainingTurns: 3 });
     expect(fixture.ai.generateMediaAsk).not.toHaveBeenCalled();
     expect(fixture.chat.sendChatMessage).not.toHaveBeenCalled();
     expect(fixture.getSaved()?.automation.handoffReason).toContain('media request has already been made');
@@ -194,7 +194,7 @@ describe('conversation automation', () => {
     const { service, chat, ai, getSaved } = harness(['onlyfans'], ['fansly.com']);
     const result = await service.processConversation(incoming(1, 'My Fansly is https://www.fansly.com/example'));
 
-    expect(result).toMatchObject({ kind: 'human-required', remainingTurns: 0 });
+    expect(result).toMatchObject({ kind: 'human-required', remainingTurns: 3 });
     expect(ai.generateMediaAsk).not.toHaveBeenCalled();
     expect(chat.sendChatMessage).not.toHaveBeenCalled();
     expect(getSaved()?.automation).toMatchObject({
@@ -550,7 +550,39 @@ describe('conversation automation', () => {
 
     expect(result?.kind).toBe('human-required');
     expect(fixture.chat.sendChatMessage).not.toHaveBeenCalled();
-    expect(fixture.getSaved()?.automation.handoffReason).toContain('failed autonomous safety checks');
+    expect(fixture.getSaved()?.automation.handoffReason)
+      .toBe('The generated reply was rejected: reply solicits media outside the configured media-ask phase.');
+  });
+
+  it('regenerates once when a legacy media ask contains no recognizable request', async () => {
+    const fixture = harness();
+    fixture.ai.generateMediaAsk
+      .mockResolvedValueOnce('That sounds fun. I would love to see that smile.')
+      .mockResolvedValueOnce('If you are up for it, snap a cute pic of yourself?');
+
+    const result = await fixture.service.processConversation(incoming(1));
+
+    expect(result).toMatchObject({ kind: 'sent', remainingTurns: 2 });
+    expect(fixture.ai.generateMediaAsk).toHaveBeenCalledTimes(2);
+    expect(fixture.chat.sendChatMessage).toHaveBeenCalledWith(
+      expect.any(String),
+      'If you are up for it, snap a cute pic of yourself?',
+    );
+  });
+
+  it('preserves unused turns and records the exact reason when regeneration is still invalid', async () => {
+    const fixture = harness();
+    fixture.ai.generateMediaAsk.mockResolvedValue('That sounds fun. I would love to see that smile.');
+
+    const result = await fixture.service.processConversation(incoming(1));
+
+    expect(result).toMatchObject({ kind: 'human-required', remainingTurns: 3 });
+    expect(fixture.ai.generateMediaAsk).toHaveBeenCalledTimes(2);
+    expect(fixture.getSaved()?.automation).toMatchObject({
+      turnsUsed: 0,
+      handoffReason: 'The generated media ask was rejected: media ask does not contain a recognizable image or video request.',
+    });
+    expect(fixture.chat.sendChatMessage).not.toHaveBeenCalled();
   });
 
   it('builds rapport before making exactly one optional media ask in hybrid mode', async () => {