feat: label AI-generated conversation messages

src/services/conversation-automation.ts

@@ -7,6 +7,7 @@ import type { ChatService } from './chat/service.js';
 import {
   buildConversationState,
   chooseConversationIntent,
+  conversationMessageFingerprint,
   MAX_AUTOMATED_CONVERSATION_TURNS,
   mergeConversationState,
   remainingAutomationTurns,
@@ -101,6 +102,7 @@ export class ConversationAutomationService {
     state.askedForMedia = true;
     state.automation.turnsUsed += 1;
     state.automation.lastIncomingKey = incomingKey;
+    state.automation.aiMessageFingerprints.push(conversationMessageFingerprint(reply));
     const exhausted = state.automation.turnsUsed >= MAX_AUTOMATED_CONVERSATION_TURNS;
     if (exhausted) {
       state.automation.status = 'human-required';

src/services/conversation-state.ts

@@ -1,3 +1,5 @@
+import { createHash } from 'node:crypto';
+
 export interface ConversationMessage {
   sender: string;
   text: string;
@@ -45,6 +47,8 @@ export interface ConversationAutomationState {
   status: ConversationAutomationStatus;
   lastIncomingKey: string | null;
   handoffReason: string | null;
+  /** SHA-256 fingerprints avoid storing a second copy of generated message text. */
+  aiMessageFingerprints: string[];
 }
 
 export function createConversationAutomationState(): ConversationAutomationState {
@@ -53,9 +57,14 @@ export function createConversationAutomationState(): ConversationAutomationState
     status: 'active',
     lastIncomingKey: null,
     handoffReason: null,
+    aiMessageFingerprints: [],
   };
 }
 
+export function conversationMessageFingerprint(message: string): string {
+  return createHash('sha256').update(message.trim()).digest('hex');
+}
+
 export function remainingAutomationTurns(state: ConversationState): number {
   if (state.automation.status !== 'active') return 0;
   return Math.max(0, MAX_AUTOMATED_CONVERSATION_TURNS - state.automation.turnsUsed);
@@ -222,6 +231,9 @@ function parseAutomationState(value: unknown): ConversationAutomationState {
     status,
     lastIncomingKey: typeof parsed.lastIncomingKey === 'string' ? parsed.lastIncomingKey : null,
     handoffReason: typeof parsed.handoffReason === 'string' ? parsed.handoffReason : null,
+    aiMessageFingerprints: Array.isArray(parsed.aiMessageFingerprints)
+      ? parsed.aiMessageFingerprints.filter((item): item is string => typeof item === 'string')
+      : [],
   };
 }
 

src/web/routes/conversations.ts

@@ -4,6 +4,7 @@ import type { WebContext } from '../context.js';
 import {
   buildConversationState,
   chooseConversationIntent,
+  conversationMessageFingerprint,
   mergeConversationState,
   remainingAutomationTurns,
 } from '../../services/conversation-state.js';
@@ -169,12 +170,14 @@ export function createConversationsRouter(ctx: WebContext): Router {
         imageUrl: string | null;
         sentAt: number;
       } | null = null;
+      let automatedOpener: string | null = null;
       try {
         const messagesRepo = resolved.runtime?.resources.messagesRepo ?? ctx.repos.messages;
         const sent = conversation.roomId
           ? messagesRepo.getByChatRoomId(conversation.roomId)
             ?? messagesRepo.getLatestByRecipient(conversation.username)
           : messagesRepo.getLatestByRecipient(conversation.username);
+        automatedOpener = sent?.message ?? null;
         if (sent && sent.postId) {
           const url = sent.postUrl ?? (sent.subreddit
             ? `https://www.reddit.com/r/${sent.subreddit}/comments/${sent.postId}/`
@@ -205,9 +208,25 @@ export function createConversationsRouter(ctx: WebContext): Router {
         intelligence.state.automation.handoffReason = intelligence.state.boundaries.join('; ');
       }
       if (conversation.roomId) stateRepo?.save(conversation.roomId, intelligence.state);
+      const aiFingerprints = new Map<string, number>();
+      if (automatedOpener) {
+        aiFingerprints.set(conversationMessageFingerprint(automatedOpener), 1);
+      }
+      for (const fingerprint of intelligence.state.automation.aiMessageFingerprints) {
+        aiFingerprints.set(fingerprint, (aiFingerprints.get(fingerprint) ?? 0) + 1);
+      }
+      const annotatedMessages = conversation.messages?.map((message) => {
+        if (!message.isSelf) return message;
+        const fingerprint = conversationMessageFingerprint(message.text);
+        const remainingMatches = aiFingerprints.get(fingerprint) ?? 0;
+        if (remainingMatches === 0) return message;
+        aiFingerprints.set(fingerprint, remainingMatches - 1);
+        return { ...message, isAi: true };
+      });
 
       res.json({
         ...conversation,
+        ...(annotatedMessages ? { messages: annotatedMessages } : {}),
         owner: resolved.runtime
           ? { accountId: resolved.runtime.session.accountId, redditUsername: resolved.runtime.session.redditUsername }
           : currentOwner(),