feat: label AI-generated conversation messages

tests/conversation-automation.test.ts

@@ -46,6 +46,7 @@ describe('conversation automation', () => {
     expect(third).toMatchObject({ kind: 'human-required', remainingTurns: 0 });
     expect(chat.sendChatMessage).toHaveBeenCalledTimes(3);
     expect(getSaved()?.automation).toMatchObject({ turnsUsed: 3, status: 'human-required' });
+    expect(getSaved()?.automation.aiMessageFingerprints).toHaveLength(3);
     expect(await service.processConversation(incoming(3))).toBeNull();
   });
 

tests/dashboard/conversations.test.tsx

@@ -40,7 +40,7 @@ function detailFixture(chat = alice) {
   return {
     ...chat,
     messages: [
-      { sender: 'me', text: 'Hello Alice', timestamp: 1_785_999_900_000, isSelf: true },
+      { sender: 'me', text: 'Hello Alice', timestamp: 1_785_999_900_000, isSelf: true, isAi: true },
       { sender: 'alice', text: 'Good to hear from you', timestamp: 1_786_000_000_000, isSelf: false },
     ],
     triggeringPost: {
@@ -136,6 +136,7 @@ describe('ConversationsPage', () => {
       expect(profileLink).toHaveAttribute('href', 'https://www.reddit.com/u/alice');
     }
     expect(screen.getByText('Good to hear from you')).toBeInTheDocument();
+    expect(screen.getByLabelText('Sent by AI')).toHaveTextContent('AI');
     expect(screen.getByRole('link', { name: 'Looking for a chat' })).toHaveAttribute('href', expect.stringContaining('post-1'));
     expect(screen.getByRole('img', { name: 'Source post: Looking for a chat' })).toHaveAttribute(
       'src',

tests/openrouter-client.test.ts

@@ -574,7 +574,7 @@ describe('OpenRouterClient', () => {
           boundaries: [],
           askedForMedia: false,
           topics: [],
-          automation: { turnsUsed: 0, status: 'active', lastIncomingKey: null, handoffReason: null },
+          automation: { turnsUsed: 0, status: 'active', lastIncomingKey: null, handoffReason: null, aiMessageFingerprints: [] },
         },
         { kind: 'answer-question', reason: 'their latest message asks a direct question' },
       );

tests/web/conversations-route.test.ts

@@ -3,6 +3,7 @@ import type { AddressInfo } from 'node:net';
 import { afterEach, describe, expect, it, vi } from 'vitest';
 import type { WebContext } from '../../src/web/context.js';
 import { createConversationsRouter } from '../../src/web/routes/conversations.js';
+import { buildConversationState, conversationMessageFingerprint } from '../../src/services/conversation-state.js';
 
 const servers: Array<ReturnType<express.Express['listen']>> = [];
 
@@ -234,13 +235,14 @@ describe('conversations route', () => {
       lastMessageSnippet: 'Hello',
       isFromUs: false,
       unread: false,
-      messages: [{
-        sender: 'alice',
-        text: 'Hello',
-        timestamp: 1_786_000_000_000,
-        isSelf: false,
-      }],
+      messages: [
+        { sender: 'me', text: 'Automated hello', timestamp: 1_785_999_900_000, isSelf: true },
+        { sender: 'alice', text: 'Hello', timestamp: 1_786_000_000_000, isSelf: false },
+      ],
     };
+    const savedState = buildConversationState(conversation.messages);
+    savedState.automation.turnsUsed = 1;
+    savedState.automation.aiMessageFingerprints = [conversationMessageFingerprint('Automated hello')];
     const refreshTopChats = vi.fn();
     const loadConversationDetails = vi.fn();
     const context = {
@@ -249,6 +251,7 @@ describe('conversations route', () => {
         messages: { getLatestByRecipient: vi.fn().mockReturnValue(undefined) },
       },
       services: {
+        conversationState: { get: vi.fn().mockReturnValue(savedState), save: vi.fn() },
         chat: {
           getSyncStatus: vi.fn().mockReturnValue({
             syncing: false,
@@ -270,11 +273,13 @@ describe('conversations route', () => {
     const body = await response.json();
     expect(body.username).toBe('alice');
     expect(body.automation).toEqual({
-      turnsUsed: 0,
-      remainingTurns: 3,
+      turnsUsed: 1,
+      remainingTurns: 2,
       status: 'active',
       handoffReason: null,
     });
+    expect(body.messages[0]).toMatchObject({ text: 'Automated hello', isAi: true });
+    expect(body.messages[1].isAi).toBeUndefined();
     expect(refreshTopChats).not.toHaveBeenCalled();
     expect(loadConversationDetails).not.toHaveBeenCalled();
   });
@@ -310,10 +315,12 @@ describe('conversations route', () => {
     const response = await request(app, '/api/conversations/room-alice');
 
     expect(response.status).toBe(200);
-    expect((await response.json()).triggeringPost).toEqual({
+    const body = await response.json();
+    expect(body.triggeringPost).toEqual({
       id: 'post-exact', subreddit: 'example', title: 'Exact source post',
       url: roomOrigin.postUrl, imageUrl: roomOrigin.postImageUrl, sentAt: 9,
     });
+    expect(body.messages[0]).toMatchObject({ text: 'Hello', isAi: true });
     expect(context.repos.messages.getLatestByRecipient).not.toHaveBeenCalled();
   });