feat: persist settings and enrich conversation context

src/services/chat/index.ts

@@ -5,6 +5,7 @@ export type {
   SyncStatus,
   SyncProgress,
   SyncPhase,
+  SyncCompletion,
   SyncProgressListener,
 } from './service.js';
 export type {
@@ -23,3 +24,4 @@ export {
   MatrixTokenRefresher,
 } from './matrix/token-refresher.js';
 export { MatrixMediaDownloader } from './matrix/http-media-downloader.js';
+export { MatrixUsernameResolver } from './matrix/username-resolver.js';

src/services/chat/matrix/client.ts

@@ -190,7 +190,13 @@ export class MatrixClient {
       }
 
       if (res.status === 401 || res.status === 403) {
-        throw new MatrixAuthError(`Matrix ${method} ${path} → ${res.status} (token likely expired)`);
+        const failure = await readMatrixFailure(res);
+        if (isMatrixAuthenticationFailure(res.status, failure.errcode)) {
+          throw new MatrixAuthError(
+            `Matrix ${method} ${path} → ${res.status} ${failure.errcode ?? ''} (token rejected)`,
+          );
+        }
+        throw new Error(`Matrix ${method} ${path} → ${res.status}: ${failure.text.slice(0, 300)}`);
       }
 
       // Matrix-standard rate-limit response: { retry_after_ms } per spec.
@@ -251,6 +257,13 @@ export class MatrixClient {
     return res.user_id;
   }
 
+  async getUserProfile(mxid: string): Promise<{ displayname?: string; avatar_url?: string }> {
+    return this.request<{ displayname?: string; avatar_url?: string }>(
+      'GET',
+      `/_matrix/client/v3/profile/${encodeURIComponent(mxid)}`,
+    );
+  }
+
   /**
    * All rooms the user is currently joined to. Use this for backfill —
    * `/sync` only returns rooms with recent activity.
@@ -502,7 +515,15 @@ export class MatrixClient {
           throw new Error(`Matrix media download ${url} timed out (exceeded ${maxAttempts} attempts)`);
         }
         if (res.status === 401 || res.status === 403) {
-          throw new MatrixAuthError(`Matrix media download → ${res.status} (token likely expired)`);
+          const failure = await readMatrixFailure(res);
+          if (isMatrixAuthenticationFailure(res.status, failure.errcode)) {
+            throw new MatrixAuthError(
+              `Matrix media download → ${res.status} ${failure.errcode ?? ''} (token rejected)`,
+            );
+          }
+          throw new Error(
+            `Matrix media download ${url} → ${res.status}: ${failure.text.slice(0, 200)}`,
+          );
         }
         if (res.status === 429) {
           const body = (await res.json().catch(() => ({}))) as { retry_after_ms?: number };
@@ -529,6 +550,29 @@ export class MatrixClient {
   }
 }
 
+interface MatrixFailure {
+  errcode?: string;
+  text: string;
+}
+
+async function readMatrixFailure(response: Response): Promise<MatrixFailure> {
+  const text = await response.text().catch(() => '');
+  if (!text) return { text };
+  try {
+    const parsed = JSON.parse(text) as { errcode?: unknown };
+    return {
+      text,
+      ...(typeof parsed.errcode === 'string' ? { errcode: parsed.errcode } : {}),
+    };
+  } catch {
+    return { text };
+  }
+}
+
+function isMatrixAuthenticationFailure(status: number, errcode?: string): boolean {
+  return status === 401 || errcode === 'M_UNKNOWN_TOKEN' || errcode === 'M_MISSING_TOKEN';
+}
+
 function parseMxc(mxc: string): { serverName: string; mediaId: string } | null {
   const m = mxc.match(/^mxc:\/\/([^/]+)\/(.+)$/);
   if (!m) return null;

src/services/chat/matrix/http-media-downloader.ts

@@ -16,6 +16,10 @@ export class MatrixMediaDownloader implements MediaDownloader {
     private logger: Logger,
   ) {}
 
+  setMatrixClient(client: MatrixClient): void {
+    this.matrix = client;
+  }
+
   async fetch(url: string): Promise<MediaDownloadResult | null> {
     try {
       if (url.startsWith('mxc://')) {

src/services/chat/matrix/username-resolver.ts

@@ -0,0 +1,29 @@
+import type { UsernameResolver } from '../service.js';
+
+interface MatrixProfileClient {
+  getUserProfile(mxid: string): Promise<{ displayname?: string }>;
+}
+
+export class MatrixUsernameResolver implements UsernameResolver {
+  constructor(private profiles: MatrixProfileClient) {}
+
+  setMatrixClient(client: MatrixProfileClient): void {
+    this.profiles = client;
+  }
+
+  async resolveT2Ids(t2Ids: string[]): Promise<Record<string, string>> {
+    const resolved: Record<string, string> = {};
+    await Promise.all(t2Ids.map(async (value) => {
+      const t2Id = value.startsWith('t2_') ? value : `t2_${value}`;
+      try {
+        const username = (await this.profiles.getUserProfile(`@${t2Id}:reddit.com`)).displayname?.trim();
+        if (username && !username.startsWith('t2_') && !username.startsWith('@')) {
+          resolved[t2Id] = username;
+        }
+      } catch {
+        // A missing profile should not prevent the rest of the batch resolving.
+      }
+    }));
+    return resolved;
+  }
+}

src/services/chat/service.ts

@@ -2,6 +2,7 @@ import type { Logger } from '../../utils/logger.js';
 import type {
   MessagesRepository,
   RedditUsersRepository,
+  SentMessageRecord,
   SuccessfulMessagesRepository,
 } from '../../database/repositories.js';
 import type { MediaService } from '../media.js';
@@ -40,10 +41,13 @@ class MatrixAuthenticationUnavailableError extends Error {
 export interface UsernameResolver {
   /** Map t2 IDs (with or without `t2_` prefix) to Reddit usernames. */
   resolveT2Ids(t2Ids: string[]): Promise<Record<string, string>>;
+  /** Resolve a Reddit username to its t2 account ID when starting a DM. */
+  resolveUsernameToT2?(username: string): Promise<string | null>;
 }
 
 interface BuildChatOpts {
   knownUsernames: Map<string, string>;
+  includeTimelineMessages?: boolean;
 }
 
 /**
@@ -98,8 +102,15 @@ export interface SyncStatus {
   progress: SyncProgress | null;
 }
 
+export type SyncCompletion =
+  | { status: 'completed' }
+  | { status: 'failed'; error: string };
+
 /** `null` signals "sync ended" (clear progress UI). */
-export type SyncProgressListener = (progress: SyncProgress | null) => void;
+export type SyncProgressListener = (
+  progress: SyncProgress | null,
+  completion?: SyncCompletion,
+) => void;
 
 /** Fired when a chat we sent into first receives a reply from the other party. */
 export type NewReplyListener = (info: {
@@ -112,6 +123,7 @@ export type NewReplyListener = (info: {
 export class ChatService {
   private cache: ChatCache;
   private queue: Promise<unknown> = Promise.resolve();
+  private deltaSyncInFlight: Promise<void> | null = null;
   private readonly t2ToUsername = new Map<string, string>();
   /** Rooms whose /joined_members lookup has already failed — don't retry. */
   private readonly unresolvableRooms = new Set<string>();
@@ -263,6 +275,7 @@ export class ChatService {
     return this.enqueue(async () => {
       if (this.cache.isFresh()) return this.cache.get();
       this.beginSync('delta');
+      let failure: unknown;
       try {
         this.updateProgress({ phase: 'starting', current: 0, total: 0 });
         const merged = await this.syncOnce();
@@ -273,8 +286,11 @@ export class ChatService {
         this.logger.info(`[chat] sync → ${merged.length} known rooms, ${active.length} active`);
         this.updateProgress({ phase: 'done', current: merged.length, total: merged.length });
         return active;
+      } catch (error) {
+        failure = error;
+        throw error;
       } finally {
-        this.endSync();
+        this.endSync(failure);
       }
     });
   }
@@ -284,9 +300,12 @@ export class ChatService {
    * cache. The `limit` arg is preserved for API compatibility but Matrix
    * already returns only rooms with new events, so it's a no-op.
    */
-  async refreshTopChats(_limit = 5): Promise<void> {
-    await this.enqueue(async () => {
+  refreshTopChats(_limit = 5): Promise<void> {
+    if (this.deltaSyncInFlight) return this.deltaSyncInFlight;
+
+    const operation = this.enqueue(async () => {
       this.beginSync('delta');
+      let failure: unknown;
       try {
         this.updateProgress({ phase: 'starting', current: 0, total: 0 });
         await this.syncOnce();
@@ -297,11 +316,19 @@ export class ChatService {
           total: this.cache.get().length,
         });
       } catch (error) {
+        failure = error;
         this.logger.error('[chat] refreshTopChats failed:', error);
+        throw error;
       } finally {
-        this.endSync();
+        this.endSync(failure);
       }
     });
+
+    const tracked = operation.finally(() => {
+      this.deltaSyncInFlight = null;
+    });
+    this.deltaSyncInFlight = tracked;
+    return tracked;
   }
 
   /**
@@ -312,6 +339,7 @@ export class ChatService {
   async fetchAllMessages(): Promise<ActiveChat[]> {
     return this.enqueue(async () => {
       this.beginSync('full');
+      let failure: unknown;
       try {
         this.logger.info('[chat] full backfill starting (via /joined_rooms)...');
         const t0 = Date.now();
@@ -326,24 +354,46 @@ export class ChatService {
         const joinedIds = await this.withAuth(() => this.matrix.getJoinedRooms());
         this.logger.info(`[chat] backfill: ${joinedIds.length} joined rooms`);
 
-        this.updateProgress({
-          phase: 'resolving-usernames',
-          current: 0,
-          total: joinedIds.length,
-        });
-        const knownUsernames = await this.resolveUsernamesForRooms(joinedIds);
+        const knownUsernames = new Map(this.t2ToUsername);
         const chats: ActiveChat[] = [];
 
         for (const roomId of joinedIds) {
           try {
             const room = seedJoined[roomId];
-            const chat = this.roomToActiveChat(roomId, room, { knownUsernames });
+            const chat = this.roomToActiveChat(roomId, room, {
+              knownUsernames,
+              includeTimelineMessages: true,
+            });
             chats.push(chat);
           } catch (err) {
             this.logger.warn(`[chat] backfill: failed to seed ${roomId}: ${(err as Error).message}`);
           }
         }
 
+        // Make the inbox usable as soon as Matrix has listed the rooms. A
+        // full history backfill can take many minutes for large accounts, so
+        // keeping these summaries local until the final room has loaded makes
+        // a healthy sync look like an empty inbox for the entire run.
+        chats.sort((a, b) => b.lastMessageTime - a.lastMessageTime);
+        this.cache.set(chats);
+        await this.cache.save(chats);
+
+        this.updateProgress({
+          phase: 'resolving-usernames',
+          current: 0,
+          total: joinedIds.length,
+        });
+        const resolvedUsernames = await this.resolveUsernamesForRooms(joinedIds, seedJoined);
+        for (const chat of chats) {
+          const t2 = this.extractT2(chat);
+          if (!t2) continue;
+          const resolved = resolvedUsernames.get(t2);
+          if (!resolved) continue;
+          chat.username = resolved;
+          if (!chat.roomName || chat.roomName.startsWith('t2_')) chat.roomName = resolved;
+        }
+        await this.cache.save(chats);
+
         let done = 0;
         for (const chat of chats) {
           this.updateProgress({
@@ -377,10 +427,12 @@ export class ChatService {
         this.updateProgress({ phase: 'done', current: chats.length, total: chats.length });
         return chats;
       } catch (error) {
+        failure = error;
         this.logger.error('[chat] fetchAllMessages failed:', error);
+        if (error instanceof MatrixAuthenticationUnavailableError) throw error;
         return this.cache.get();
       } finally {
-        this.endSync();
+        this.endSync(failure);
       }
     });
   }
@@ -446,12 +498,18 @@ export class ChatService {
     this.emitProgress();
   }
 
-  private endSync(): void {
+  private endSync(error?: unknown): void {
     this.syncingKind = null;
     this.progress = null;
     if (this.progressListener) {
       try {
-        this.progressListener(null);
+        const completion: SyncCompletion = error === undefined
+          ? { status: 'completed' }
+          : {
+              status: 'failed',
+              error: error instanceof Error ? error.message : String(error),
+            };
+        this.progressListener(null, completion);
       } catch (err) {
         this.logger.debug('progress listener error:', err);
       }
@@ -522,7 +580,11 @@ export class ChatService {
    * Start a brand-new DM with the given Reddit user and send the opening
    * line. Returns the new chat (or null on failure).
    */
-  async startConversation(username: string, message: string): Promise<ActiveChat | null> {
+  async startConversation(
+    username: string,
+    message: string,
+    knownT2Id?: string,
+  ): Promise<ActiveChat | null> {
     if (!this.accountAuth?.isFullyAuthenticated()) return null;
     const active = this.getInvitationCooldown();
     if (active) {
@@ -534,7 +596,7 @@ export class ChatService {
     }
     return this.enqueue(async () => {
       try {
-        const t2Id = await this.resolveUsernameToT2(username);
+        const t2Id = await this.resolveUsernameToT2(username, knownT2Id);
         if (!t2Id) {
           this.logger.error(`[chat] cannot start conversation: unknown user "${username}"`);
           return null;
@@ -657,7 +719,7 @@ export class ChatService {
     const joined = sync.rooms?.join ?? {};
 
     const existing = new Map(this.cache.get().map((c) => [c.roomId!, c] as const));
-    const knownUsernames = await this.resolveUsernamesForRooms(Object.keys(joined));
+    const knownUsernames = await this.resolveUsernamesForRooms(Object.keys(joined), joined);
 
     for (const [roomId, room] of Object.entries(joined)) {
       const prev = existing.get(roomId);
@@ -786,38 +848,36 @@ export class ChatService {
     if (firstSelf) chat.originMessage = firstSelf.text;
 
     const hasReply = chat.messages.some((m) => !m.isSelf);
+    let performanceMessage: SentMessageRecord | undefined;
 
     if (firstSelf && chat.roomId && this.messagesRepo) {
       try {
         const existing = this.messagesRepo.getByChatRoomId(chat.roomId);
-        const id = existing
-          ? existing.id
-          : this.messagesRepo.insertChat({
-              recipient: chat.username,
-              subject: chat.username,
-              message: firstSelf.text,
-              sentAt: firstSelf.timestamp,
-              chatRoomId: chat.roomId,
-            });
-        if (hasReply && !existing?.gotResponse) {
-          this.messagesRepo.markGotResponse(id);
+        const hasPerformanceContext = Boolean(
+          existing?.postId || existing?.strategyId || existing?.subreddit,
+        );
+        if (existing && hasPerformanceContext) {
+          performanceMessage = existing;
+          if (hasReply && !existing.gotResponse) {
+            this.messagesRepo.markGotResponse(existing.id);
+          }
         }
       } catch (err) {
-        this.logger.warn('[chat] failed to record sent_message for stats:', err);
+        this.logger.warn('[chat] failed to associate reply with performance context:', err);
       }
     }
 
-    if (firstSelf && hasReply && this.successfulMessagesRepo) {
+    if (firstSelf && hasReply && performanceMessage && this.successfulMessagesRepo) {
       if (!this.successfulMessagesRepo.existsByMessage(firstSelf.text)) {
         const firstReply = chat.messages.find((m) => !m.isSelf);
         try {
           this.successfulMessagesRepo.insert({
-            sentMessageId: null,
+            sentMessageId: performanceMessage.id,
             originalMessage: firstSelf.text,
-            imageAnalysis: null,
-            postTitle: `Chat with ${chat.username}`,
+            imageAnalysis: performanceMessage.postImageAnalysis ?? null,
+            postTitle: performanceMessage.postTitle ?? null,
             responseSnippet: firstReply?.text.slice(0, 200) || null,
-            subreddit: null,
+            subreddit: performanceMessage.subreddit ?? null,
           });
           this.logger.info(`[chat] stored successful chat example from ${chat.username}`);
           try {
@@ -916,6 +976,10 @@ export class ChatService {
       isFromUs = lastMessage.sender === this.matrix.userId;
     }
 
+    const timelineMessages = opts.includeTimelineMessages && !prev?.messages
+      ? this.scrapeMessageEvents(timeline).map(({ mediaUrls: _ignored, ...message }) => message)
+      : prev?.messages;
+
     const unread = (room?.unread_notifications?.notification_count ?? 0) > 0;
 
     return {
@@ -928,6 +992,7 @@ export class ChatService {
       unread,
       url: ROOM_URL_PREFIX + encodeURIComponent(roomId),
       roomId,
+      ...(timelineMessages ? { messages: timelineMessages } : {}),
     };
   }
 
@@ -956,16 +1021,58 @@ export class ChatService {
     * as a fallback. Failures are logged and ignored, with the t2 ID
     * staying as the fallback display.
     */
-  private async resolveUsernamesForRooms(roomIds: string[]): Promise<Map<string, string>> {
-    // Collect all known t2 IDs (from the in-memory cache) and query
-    // Reddit's alfred API for reverse-resolution.
+  private async resolveUsernamesForRooms(
+    roomIds: string[],
+    rooms: Record<string, MatrixJoinedRoom> = {},
+  ): Promise<Map<string, string>> {
     const cached = new Map(this.t2ToUsername);
+    const candidateT2s = new Set(cached.keys());
 
-    const staleT2s = Array.from(cached.keys()).filter(id => {
+    for (const roomId of roomIds) {
+      const room = rooms[roomId];
+      const mxids = [
+        ...(room?.summary?.['m.heroes'] ?? []),
+        ...(room?.state?.events ?? []).map((event) =>
+          (event as MatrixTimelineEvent & { state_key?: string }).state_key,
+        ),
+        ...(room?.timeline?.events ?? []).map((event) => event.sender),
+      ];
+      for (const mxid of mxids) {
+        if (!mxid || mxid === this.matrix.userId) continue;
+        const t2 = mxid.match(/^@t2_([^:]+):/)?.[1];
+        if (t2) candidateT2s.add(t2);
+      }
+    }
+
+    let staleT2s = Array.from(candidateT2s).filter(id => {
       const name = cached.get(id);
       return !name || name.startsWith('t2_') || name.startsWith('@') || this.isStaleUsername(name);
     });
 
+    // Matrix already knows the display name attached to each room member, so
+    // prefer that authenticated source before trying Reddit's legacy lookup.
+    if (staleT2s.length > 0 && this.usernameResolver) {
+      try {
+        const resolved = await this.usernameResolver.resolveT2Ids(
+          staleT2s.map((id) => `t2_${id}`),
+        );
+        for (const [t2, name] of Object.entries(resolved)) {
+          const bare = t2.replace(/^t2_/, '');
+          cached.set(bare, name);
+          this.t2ToUsername.set(bare, name);
+          this.persistUsername(t2, name);
+        }
+      } catch (err) {
+        this.logger.debug('[chat] MXID resolution failed:', err);
+      }
+      staleT2s = staleT2s.filter((id) => {
+        const name = cached.get(id);
+        return !name || this.isStaleUsername(name);
+      });
+    }
+
+    // Fall back to Reddit's alfred API for profiles without a Matrix display
+    // name. This is best-effort and leaves the stable t2 ID visible on error.
     if (staleT2s.length > 0) {
       const numericIds = staleT2s.map(id => id.replace(/^t2_/, ''));
       try {
@@ -1014,23 +1121,6 @@ export class ChatService {
       }
     }
 
-    // Also resolve MXID-based t2 IDs via the lifted UsernameResolver,
-    // while avoiding re-queries for IDs we already resolved via alfred.
-    const mxidT2s = Array.from(new Set(staleT2s.filter(id => !cached.get(id.replace(/^t2_/, '')))));
-    if (mxidT2s.length > 0 && this.usernameResolver) {
-      try {
-        const resolved = await this.usernameResolver.resolveT2Ids(mxidT2s);
-        for (const [t2, name] of Object.entries(resolved)) {
-          const bare = t2.replace(/^t2_/, '');
-          cached.set(bare, name);
-          this.t2ToUsername.set(bare, name);
-          this.persistUsername(t2, name);
-        }
-      } catch (err) {
-        this.logger.debug('[chat] MXID resolution failed:', err);
-      }
-    }
-
     return cached;
   }
 
@@ -1170,28 +1260,21 @@ export class ChatService {
     if (dirty) await this.cache.save();
   }
 
-  /**
-   * Look up the t2 ID for a Reddit username via the standard about.json
-   * endpoint. Returns `t2_xxx` or null.
-   */
-  private async resolveUsernameToT2(username: string): Promise<string | null> {
-    try {
-      const res = await fetchWithTimeout(
-        `https://www.reddit.com/user/${encodeURIComponent(username)}/about.json`,
-        { headers: { 'User-Agent': 'reddit-bot-chat/1.0' }, timeoutMs: 15_000 },
-      );
-      if (!res.ok) {
-        this.logger.warn(`[chat] /user/${username}/about.json → ${res.status}`);
-        return null;
-      }
-      const json = (await res.json()) as { data?: { id?: string } };
-      const id = json.data?.id;
-      if (!id) return null;
-      return id.startsWith('t2_') ? id : `t2_${id}`;
-    } catch (err) {
-      this.logger.error(`[chat] failed to resolve username "${username}":`, err);
-      return null;
+  /** Resolve an account ID from listing data, the durable cache, or Reddit auth. */
+  private async resolveUsernameToT2(
+    username: string,
+    knownT2Id?: string,
+  ): Promise<string | null> {
+    if (knownT2Id && /^t2_[a-z0-9]+$/i.test(knownT2Id)) return knownT2Id;
+
+    const cached = this.redditUsersRepo?.getByUsername(username);
+    if (cached) return cached.t2Id;
+
+    if (this.usernameResolver?.resolveUsernameToT2) {
+      return this.usernameResolver.resolveUsernameToT2(username);
     }
+
+    return null;
   }
 
   /** Parse a chat URL like `…/room/!abc%3Areddit.com` → `!abc:reddit.com`. */

src/services/chat/types.ts

@@ -23,6 +23,7 @@ export interface ActiveChat {
   roomId?: string;
   messages?: ChatMessage[];
   originMessage?: string;
+  hasReceivedImages?: boolean;
 }
 
 /**