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 () => {

tests/conversation-state.test.ts

@@ -3,6 +3,7 @@ import {
   buildConversationState,
   chooseConversationIntent,
   formatConversationAsUntrustedData,
+  hybridMediaAskSafetyFailure,
   mergeConversationState,
   isSafeConversationReply,
   isSafeHybridMediaAsk,
@@ -88,6 +89,15 @@ describe('conversation state', () => {
     expect(chooseConversationIntent([], state, 'media-ask').kind).toBe('follow-up');
   });
 
+  it('reports unused turns even when automation is paused for another reason', () => {
+    const state = buildConversationState([message('Hello', true), message('Hey')]);
+    state.automation.turnsUsed = 1;
+    state.automation.status = 'human-required';
+
+    expect(remainingAutomationTurns(state)).toBe(2);
+    expect(chooseConversationIntent([], state, 'media-ask').kind).toBe('follow-up');
+  });
+
   it('migrates legacy saved state with a fresh automation counter', () => {
     const state = parseConversationState(JSON.stringify({
       persona: { age: null, location: null, relationshipStatus: 'unspecified' },
@@ -146,9 +156,13 @@ describe('conversation state', () => {
 
   it('allows only optional non-explicit media asks in the hybrid phase', () => {
     expect(isSafeHybridMediaAsk('Would you be comfortable sharing a selfie?')).toBe(true);
+    expect(isSafeHybridMediaAsk('If you are up for it, snap a cute pic of yourself today?')).toBe(true);
+    expect(isSafeHybridMediaAsk('You can attach or upload a photo if you like.')).toBe(true);
     expect(isSafeHybridMediaAsk('Would you send me a nude?')).toBe(false);
     expect(isSafeHybridMediaAsk('You have to prove it by sending a photo.')).toBe(false);
     expect(isSafeHybridMediaAsk('What music are you into?')).toBe(false);
+    expect(hybridMediaAskSafetyFailure('What music are you into?'))
+      .toBe('media ask does not contain a recognizable image or video request');
   });
 
   it('rejects replies that imply shared location or encourage meeting in person', () => {

tests/dashboard/conversations.test.tsx

@@ -313,6 +313,29 @@ describe('ConversationsPage', () => {
     expect(await screen.findByRole('textbox', { name: 'Reply to u/alice' })).toHaveValue('Would you like to share a photo?');
   });
 
+  it('shows unused turns separately from a safety handoff', async () => {
+    server.use(
+      http.get('/api/conversations', () => HttpResponse.json([alice])),
+      http.get('/api/conversations/room-alice', () => HttpResponse.json({
+        ...detailFixture(),
+        automation: {
+          turnsUsed: 0,
+          remainingTurns: 3,
+          status: 'human-required',
+          handoffReason: 'The generated media ask was rejected: media ask does not contain a recognizable image or video request.',
+        },
+      })),
+    );
+    const user = userEvent.setup();
+    renderConversations();
+
+    await user.click(await screen.findByRole('button', { name: /u\/alice/ }));
+
+    expect(await screen.findByText('3 automated turns remaining')).toBeInTheDocument();
+    expect(screen.getByText(/generated media ask was rejected/)).toBeInTheDocument();
+    expect(screen.getByRole('button', { name: 'Suggest media ask' })).toBeDisabled();
+  });
+
   it('starts a conversation and preserves both fields after a recoverable failure', async () => {
     installConversationList();
     let startRequests = 0;