Improve messaging and dashboard reliability

apps/dashboard/src/features/conversations/conversations-page.tsx

@@ -1,4 +1,4 @@
-import { useMemo, useState } from 'react';
+import { useEffect, useMemo, useState } from 'react';
 import type { ActiveChat } from '../../../../../packages/api-contracts/src/index.js';
 import { RedditUsernameLink, redditUsernameLabel } from '../../components/reddit-username-link.js';
 import { ConversationDetail } from './conversation-detail.js';
@@ -8,6 +8,7 @@ import { ProcessedUserLookup } from './processed-user-lookup.js';
 import { AccountOwnerBadge } from '../../components/account-owner-badge.js';
 import './conversations.css';
 import { ownedConversationId } from './conversation-identity.js';
+import { formatExactTime, formatShortRelativeTime } from './relative-time.js';
 
 export type ConversationFilter = 'all' | 'unread' | 'awaiting-reply' | 'received-images';
 
@@ -30,9 +31,10 @@ function matchesFilter(conversation: ActiveChat, filter: ConversationFilter): bo
   return true;
 }
 
-function ConversationListItem({ conversation, isSelected, onSelect }: {
+function ConversationListItem({ conversation, isSelected, now, onSelect }: {
   conversation: ActiveChat;
   isSelected: boolean;
+  now: number;
   onSelect(): void;
 }) {
   const state = conversation.unread ? 'Unread' : conversation.isFromUs ? 'Awaiting reply' : 'Up to date';
@@ -45,7 +47,15 @@ function ConversationListItem({ conversation, isSelected, onSelect }: {
         onClick={onSelect}
         type="button"
       />
-      <span className="conversation-list-heading"><strong><RedditUsernameLink username={conversation.username} /></strong><small>{state}</small></span>
+      <span className="conversation-list-heading">
+        <strong><RedditUsernameLink username={conversation.username} /></strong>
+        <span className="conversation-list-meta">
+          <small>{state}</small>
+          <time dateTime={new Date(conversation.lastMessageTime).toISOString()} title={formatExactTime(conversation.lastMessageTime)}>
+            {formatShortRelativeTime(conversation.lastMessageTime, now)}
+          </time>
+        </span>
+      </span>
       <AccountOwnerBadge owner={conversation.owner} />
       {conversation.hasReceivedImages ? <span className="conversation-image-marker">Image received</span> : null}
       <span>{conversation.lastMessageSnippet || 'No message preview'}</span>
@@ -58,9 +68,15 @@ export function ConversationsPage({ selectedConversationId, onSelectedConversati
   const [internalSelectedId, setInternalSelectedId] = useState<string | null>(null);
   const [localFilters, setLocalFilters] = useState<ConversationFilters>({ search: '', filter: 'all' });
   const [isStartingConversation, setIsStartingConversation] = useState(false);
+  const [now, setNow] = useState(() => Date.now());
   const activeConversationId = selectedConversationId !== undefined ? selectedConversationId : internalSelectedId;
   const activeFilters = filters ?? localFilters;
 
+  useEffect(() => {
+    const interval = window.setInterval(() => setNow(Date.now()), 60_000);
+    return () => window.clearInterval(interval);
+  }, []);
+
   function updateFilters(next: ConversationFilters) {
     if (filters === undefined) setLocalFilters(next);
     onFiltersChange?.(next);
@@ -68,12 +84,14 @@ export function ConversationsPage({ selectedConversationId, onSelectedConversati
 
   const visibleConversations = useMemo(() => {
     const normalizedSearch = activeFilters.search.trim().toLowerCase();
-    return (conversationsQuery.data ?? []).filter((conversation) => {
+    return (conversationsQuery.data ?? [])
+      .filter((conversation) => {
         const matchesSearch = normalizedSearch.length === 0
           || conversation.username.toLowerCase().includes(normalizedSearch)
           || conversation.lastMessageSnippet.toLowerCase().includes(normalizedSearch);
         return matchesSearch && matchesFilter(conversation, activeFilters.filter);
-    });
+      })
+      .sort((left, right) => right.lastMessageTime - left.lastMessageTime);
   }, [activeFilters, conversationsQuery.data]);
 
   function selectConversation(id: string | null) {
@@ -144,6 +162,7 @@ export function ConversationsPage({ selectedConversationId, onSelectedConversati
                   conversation={conversation}
                   isSelected={ownedConversationId(conversation) === activeConversationId}
                   key={ownedConversationId(conversation)}
+                  now={now}
                   onSelect={() => selectConversation(ownedConversationId(conversation))}
                 />
               ))}

apps/dashboard/src/features/conversations/conversations.css

@@ -43,6 +43,8 @@
 .conversation-list-item > span:last-child { overflow: hidden; color: var(--muted); font-size: .82rem; text-overflow: ellipsis; white-space: nowrap; }
 .conversation-list-heading { display: flex; align-items: center; justify-content: space-between; gap: .5rem; }
 .conversation-list-heading small { color: var(--accent); }
+.conversation-list-meta { display: flex; align-items: center; gap: .45rem; }
+.conversation-list-meta time { color: var(--muted); font-size: .7rem; white-space: nowrap; }
 .conversation-image-marker { justify-self: start; padding: .18rem .45rem; color: #d8e8ff !important; background: #18324d; border: 1px solid #315d85; border-radius: 999px; font-size: .68rem !important; font-weight: 750; }
 .conversation-list-state, .conversation-detail-state { display: grid; place-items: center; align-content: center; gap: .5rem; min-height: 16rem; padding: 1.5rem; color: var(--muted); text-align: center; }
 .conversation-list-state strong, .conversation-detail-state strong { color: #e9f1ec; }

apps/dashboard/src/features/conversations/relative-time.ts

@@ -0,0 +1,20 @@
+const MINUTE_MS = 60_000;
+const HOUR_MS = 60 * MINUTE_MS;
+const DAY_MS = 24 * HOUR_MS;
+const MONTH_MS = 30 * DAY_MS;
+const YEAR_MS = 365 * DAY_MS;
+
+export function formatShortRelativeTime(timestamp: number, now: number): string {
+  const elapsed = Math.max(0, now - timestamp);
+
+  if (elapsed < MINUTE_MS) return 'just now';
+  if (elapsed < HOUR_MS) return `${Math.floor(elapsed / MINUTE_MS)}m ago`;
+  if (elapsed < DAY_MS) return `${Math.floor(elapsed / HOUR_MS)}h ago`;
+  if (elapsed < MONTH_MS) return `${Math.floor(elapsed / DAY_MS)}d ago`;
+  if (elapsed < YEAR_MS) return `${Math.floor(elapsed / MONTH_MS)}mo ago`;
+  return `${Math.floor(elapsed / YEAR_MS)}y ago`;
+}
+
+export function formatExactTime(timestamp: number): string {
+  return new Intl.DateTimeFormat(undefined, { dateStyle: 'medium', timeStyle: 'short' }).format(timestamp);
+}

apps/dashboard/src/features/media/filters.ts

@@ -23,11 +23,13 @@ export function filterMedia(items: MediaItem[], filters: MediaFilters, now: numb
     '30d': 30 * 86_400_000,
   }[filters.dateRange];
 
-  return items.filter((item) => {
+  return items
+    .filter((item) => {
       if (filters.conversation !== 'all' && mediaConversation(item) !== filters.conversation) return false;
       if (filters.sender !== 'all' && item.sender !== filters.sender) return false;
       if (filters.type !== 'all' && mediaType(item) !== filters.type) return false;
       if (rangeMs !== null && item.timestamp < now - rangeMs) return false;
       return true;
-  });
+    })
+    .sort((left, right) => right.timestamp - left.timestamp);
 }

src/bootstrap.ts

@@ -12,6 +12,7 @@ import {
   ConversationStateRepository,
   ConversationOutcomesRepository,
   DeliveryOutboxRepository,
+  RecipientHistoryRepository,
 } from './database/repositories.js';
 import { BrowserClient } from './browser/client.js';
 import { RedditApiClient } from './reddit/api.js';
@@ -46,6 +47,7 @@ import { ChatCache } from './services/chat/cache.js';
 import { RedditAccountRuntimeManager } from './services/reddit-account-runtime.js';
 import { createConcreteRedditAccountRuntimeFactory } from './services/reddit-account-runtime-builder.js';
 import { importLegacyAccountContent } from './database/legacy-content-import.js';
+import { RecipientDeduplicator } from './services/recipient-deduplicator.js';
 
 export interface AppContainer {
   config: Config;
@@ -63,6 +65,7 @@ export interface AppContainer {
   deliveryOutboxRepo: DeliveryOutboxRepository;
   conversationStateRepo: ConversationStateRepository;
   conversationOutcomesRepo: ConversationOutcomesRepository;
+  recipientDeduplicator: RecipientDeduplicator;
 
   redditApi: RedditApiClient;
   aiClient: OpenRouterClient;
@@ -119,6 +122,7 @@ export async function bootstrap(
   const deliveryOutboxRepo = new DeliveryOutboxRepository(db, bootstrapAccountId);
   const conversationStateRepo = new ConversationStateRepository(db, bootstrapAccountId);
   const conversationOutcomesRepo = new ConversationOutcomesRepository(db, bootstrapAccountId);
+  const recipientDeduplicator = new RecipientDeduplicator(new RecipientHistoryRepository(db));
   const redditAccountsRepo = bootstrapAccountsRepo;
   const accountContentRepo = new AccountContentRepository(db);
   const legacyImport = importLegacyAccountContent(db);
@@ -163,7 +167,7 @@ export async function bootstrap(
 
   // AI + services
   const aiClient = new OpenRouterClient(config, logger);
-  const monitorService = new MonitorService(redditApi, postsRepo, messagesRepo, config, logger);
+  const monitorService = new MonitorService(redditApi, postsRepo, recipientDeduplicator, config, logger);
   const processorService = new ProcessorService(redditApi, aiClient, config, logger);
   const strategySelector = new StrategySelector(config, messagesRepo, logger);
   processorService.setStrategySelector(strategySelector);
@@ -436,6 +440,7 @@ export async function bootstrap(
     deliveryOutboxRepo,
     conversationStateRepo,
     conversationOutcomesRepo,
+    recipientDeduplicator,
     redditApi,
     aiClient,
     monitorService,

src/database/repositories.ts

@@ -109,6 +109,24 @@ export interface DeliveryOutboxRecord {
   sentMessageId: number | null;
 }
 
+/** Read-only recipient history shared by every Reddit account runtime. */
+export class RecipientHistoryRepository {
+  private readonly hasSentToStmt: Database.Statement;
+
+  constructor(db: Database.Database) {
+    this.hasSentToStmt = db.prepare(`
+      SELECT 1
+      FROM sent_messages
+      WHERE recipient = ? COLLATE NOCASE
+      LIMIT 1
+    `);
+  }
+
+  hasSentTo(recipient: string): boolean {
+    return this.hasSentToStmt.get(recipient) !== undefined;
+  }
+}
+
 /**
  * Durable state for an outbound delivery. The caller must only perform the
  * remote send after claiming an item, then acknowledge it using the same

src/main-loop.ts

@@ -85,6 +85,7 @@ export async function runMainLoop(app: AppContainer): Promise<void> {
     accountAuth,
     postsRepo,
     messagesRepo,
+    recipientDeduplicator,
     redditApi,
     monitorService,
     processorService,
@@ -290,17 +291,35 @@ export async function runMainLoop(app: AppContainer): Promise<void> {
 
           await rateLimiter.throttle(
             async () => {
+              if (!recipientDeduplicator.tryReserve(post.author)) {
+                const reason = 'User already contacted across accounts';
+                logger.info(`Skipping u/${post.author} - ${reason.toLowerCase()}`);
+                postsRepo.setError(post.id, reason);
+                webServer?.logActivity(
+                  'skipped',
+                  `Skipped u/${post.author} (already contacted across accounts)`,
+                  post.author,
+                );
+                return false;
+              }
+
               logger.info(`Sending message to u/${post.author}...`);
               webServer?.pushLog('info', `Sending message to u/${post.author}...`);
 
-              const chat = await chatService.startConversation(
+              let chat;
+              try {
+                chat = await chatService.startConversation(
                   post.author,
                   processed.generatedMessage,
                   post.author_fullname,
                 );
+              } catch (error) {
+                recipientDeduplicator.release(post.author);
+                throw error;
+              }
               const success = chat !== null;
 
-              if (success) {
+              if (chat) {
                 postsRepo.markMessageSent(post.id);
 
                 // Refresh top chats in background so dashboard is up-to-date.
@@ -340,6 +359,7 @@ export async function runMainLoop(app: AppContainer): Promise<void> {
                   });
                 }
               } else {
+                recipientDeduplicator.release(post.author);
                 postsRepo.setError(post.id, 'Failed to send message');
                 webServer?.logActivity(
                   'error',

src/services/chat/matrix/client.ts

@@ -14,6 +14,18 @@ export class MatrixAuthError extends Error {
   }
 }
 
+/**
+ * Thrown when Reddit's homeserver explicitly disables a Matrix endpoint.
+ * Callers can remember the missing capability instead of retrying it for
+ * every room while still using the remaining Matrix API normally.
+ */
+export class MatrixFeatureDisabledError extends Error {
+  constructor(message: string) {
+    super(message);
+    this.name = 'MatrixFeatureDisabledError';
+  }
+}
+
 /**
  * Thrown when Reddit's homeserver returns a 429 with a `retry_after_ms`
  * longer than we're willing to block on. Caller (typically ChatService)
@@ -201,6 +213,11 @@ export class MatrixClient {
             `Matrix ${method} ${path} → ${res.status} ${failure.errcode ?? ''} (token rejected)`,
           );
         }
+        if (res.status === 403 && isFeatureDisabledFailure(failure.text)) {
+          throw new MatrixFeatureDisabledError(
+            `Matrix ${method} ${path} → 403 (disabled by configuration)`,
+          );
+        }
         throw new Error(`Matrix ${method} ${path} → ${res.status}: ${failure.text.slice(0, 300)}`);
       }
 
@@ -626,6 +643,16 @@ function isMatrixAuthenticationFailure(status: number, errcode?: string): boolea
   return status === 401 || errcode === 'M_UNKNOWN_TOKEN' || errcode === 'M_MISSING_TOKEN';
 }
 
+function isFeatureDisabledFailure(responseText: string): boolean {
+  try {
+    const parsed = JSON.parse(responseText) as { message?: unknown };
+    return typeof parsed.message === 'string'
+      && parsed.message.toLowerCase() === 'disabled by configuration';
+  } catch {
+    return false;
+  }
+}
+
 function parseMxc(mxc: string): { serverName: string; mediaId: string } | null {
   const m = mxc.match(/^mxc:\/\/([^/]+)\/(.+)$/);
   if (!m) return null;

src/services/chat/service.ts

@@ -7,7 +7,12 @@ import type {
 } from '../../database/repositories.js';
 import type { MediaService } from '../media.js';
 import { ChatCache } from './cache.js';
-import { MatrixClient, MatrixAuthError, MatrixRateLimitError } from './matrix/client.js';
+import {
+  MatrixClient,
+  MatrixAuthError,
+  MatrixFeatureDisabledError,
+  MatrixRateLimitError,
+} from './matrix/client.js';
 import type { MatrixJoinedRoom, MatrixTimelineEvent } from './matrix/types.js';
 import type { ActiveChat, ChatMessage, ScrapedChatMessage, InvitationCooldown } from './types.js';
 
@@ -128,6 +133,7 @@ export class ChatService {
   private readonly t2ToUsername = new Map<string, string>();
   /** Rooms whose /joined_members lookup has already failed — don't retry. */
   private readonly unresolvableRooms = new Set<string>();
+  private roomStateLookupAvailable = true;
   private syncingKind: 'full' | 'delta' | null = null;
   private progress: SyncProgress | null = null;
   private progressListener: SyncProgressListener | null = null;
@@ -1341,6 +1347,7 @@ export class ChatService {
         chat.username.startsWith('@');
       if (!needsLookup) continue;
       let t2: string | undefined;
+      if (this.roomStateLookupAvailable) {
         try {
           const state = await this.withAuth(() => this.matrix.getRoomFullState(chat.roomId!));
           const otherMember = state.find((e) => {
@@ -1359,8 +1366,14 @@ export class ChatService {
             this.logger.warn('[chat] username enrichment paused until Reddit login is restored');
             return;
           }
+          if (err instanceof MatrixFeatureDisabledError) {
+            this.roomStateLookupAvailable = false;
+            this.logger.debug('[chat] room state lookup is disabled upstream; using message history instead');
+          } else {
             this.logger.debug(`[chat] /state lookup failed for ${chat.roomId}:`, err);
           }
+        }
+      }
       if (!t2) {
         try {
           const res = await this.withAuth(() =>

src/services/monitor.ts

@@ -1,5 +1,5 @@
 import { RedditRateLimitError, type RedditApiClient, type RedditPost } from '../reddit/api.js';
-import type { PostsRepository, MessagesRepository } from '../database/repositories.js';
+import type { PostsRepository } from '../database/repositories.js';
 import type { Config } from '../config/index.js';
 import type { Logger } from '../utils/logger.js';
 import { parseGenderTag } from '../utils/gender-tag.js';
@@ -13,7 +13,7 @@ export class MonitorService {
   constructor(
     private redditApi: RedditApiClient,
     private postsRepo: PostsRepository,
-    private messagesRepo: MessagesRepository,
+    private recipientHistory: { hasSentTo(recipient: string): boolean },
     private config: Config,
     private logger: Logger,
     private delayBetweenFetchesMs: number = 1000,
@@ -46,7 +46,7 @@ export class MonitorService {
             continue;
           }
 
-          if (this.messagesRepo.hasSentTo(post.author)) {
+          if (this.recipientHistory.hasSentTo(post.author)) {
             this.logger.debug(`Skipping post ${post.id} from u/${post.author} - already messaged this user`);
             continue;
           }

src/services/recipient-deduplicator.ts

@@ -0,0 +1,39 @@
+export interface RecipientHistory {
+  hasSentTo(recipient: string): boolean;
+}
+
+/**
+ * Coordinates recipient selection across account runtimes.
+ *
+ * SQLite history prevents duplicates across restarts. The in-memory
+ * reservation closes the smaller race where two live runtimes both pass the
+ * history check before either has persisted its successful send.
+ */
+export class RecipientDeduplicator {
+  private readonly reservations = new Set<string>();
+
+  constructor(private readonly history: RecipientHistory) {}
+
+  hasSentTo(recipient: string): boolean {
+    const key = normalizeRecipient(recipient);
+    return !key || this.reservations.has(key) || this.history.hasSentTo(recipient);
+  }
+
+  tryReserve(recipient: string): boolean {
+    const key = normalizeRecipient(recipient);
+    if (!key || this.reservations.has(key) || this.history.hasSentTo(recipient)) {
+      return false;
+    }
+    this.reservations.add(key);
+    return true;
+  }
+
+  release(recipient: string): void {
+    const key = normalizeRecipient(recipient);
+    if (key) this.reservations.delete(key);
+  }
+}
+
+function normalizeRecipient(recipient: string): string {
+  return recipient.trim().toLocaleLowerCase('en-US');
+}

src/services/reddit-account-runtime-builder.ts

@@ -9,6 +9,7 @@ import {
   DeliveryOutboxRepository, ConversationStateRepository,
   ConversationOutcomesRepository, RedditUsersRepository,
   ActivityLogRepository,
+  RecipientHistoryRepository,
 } from '../database/repositories.js';
 import { AccountContentRepository } from '../database/account-repositories.js';
 import { RedditApiClient } from '../reddit/api.js';
@@ -36,6 +37,7 @@ import {
   accountBrowserProfileDir, type RedditAccountRuntimeResources,
   type VerifiedAccountSession,
 } from './reddit-account-runtime.js';
+import { RecipientDeduplicator } from './recipient-deduplicator.js';
 
 export interface ConcreteRuntimeFactoryOptions {
   config: Config;
@@ -47,12 +49,18 @@ export interface ConcreteRuntimeFactoryOptions {
 export function createConcreteRedditAccountRuntimeFactory(
   options: ConcreteRuntimeFactoryOptions,
 ): RedditAccountRuntimeFactory {
-  return new RedditAccountRuntimeFactory((session) => buildRuntime(options, session));
+  const recipientDeduplicator = new RecipientDeduplicator(
+    new RecipientHistoryRepository(options.db),
+  );
+  return new RedditAccountRuntimeFactory(
+    (session) => buildRuntime(options, session, recipientDeduplicator),
+  );
 }
 
 async function buildRuntime(
   { config, logger, db, isBotRunning = () => true }: ConcreteRuntimeFactoryOptions,
   session: VerifiedAccountSession,
+  recipientDeduplicator: RecipientDeduplicator,
 ): Promise<RedditAccountRuntime> {
   const browserProfileDir = accountBrowserProfileDir(
     path.resolve(process.cwd(), config.browser.sessionDir),
@@ -103,7 +111,9 @@ async function buildRuntime(
     redditApi.setBrowserContext(browserClient.getContext()!);
     const chatPage = await browserClient.getContext()!.newPage();
     const aiClient = new OpenRouterClient(accountConfig, logger);
-    const monitorService = new MonitorService(redditApi, postsRepo, messagesRepo, accountConfig, logger);
+    const monitorService = new MonitorService(
+      redditApi, postsRepo, recipientDeduplicator, accountConfig, logger,
+    );
     const processorService = new ProcessorService(redditApi, aiClient, accountConfig, logger);
     processorService.setStrategySelector(new StrategySelector(accountConfig, messagesRepo, logger));
     processorService.setChatStrategySelector(new StrategySelector(accountConfig, messagesRepo, logger, 'chatStrategies'));
@@ -146,7 +156,9 @@ async function buildRuntime(
       monitorService, processorService, responseChecker, chatService, mediaService,
       mediaSyncService, rateLimiter,
     };
-    const lifecycle = new AccountRuntimeLoop(resources, accountConfig, logger, isBotRunning);
+    const lifecycle = new AccountRuntimeLoop(
+      resources, accountConfig, logger, isBotRunning, recipientDeduplicator,
+    );
     return new RedditAccountRuntime(session, resources, lifecycle);
   } catch (error) {
     await browserClient.close();
@@ -175,6 +187,7 @@ class AccountRuntimeLoop {
     private readonly config: Config,
     private readonly logger: Logger,
     private readonly isBotRunning: () => boolean,
+    private readonly recipientDeduplicator: RecipientDeduplicator,
   ) {}
 
   start(): void {
@@ -257,8 +270,26 @@ class AccountRuntimeLoop {
         }
         postsRepo.updateAnalysis(post.id, processed.imageAnalysis, processed.generatedMessage);
         await rateLimiter.throttle(async () => {
-          const chat = await chatService.startConversation(post.author, processed.generatedMessage, post.author_fullname);
+          if (!this.recipientDeduplicator.tryReserve(post.author)) {
-          if (!chat) return false;
+            postsRepo.setError(post.id, 'User already contacted across accounts');
+            this.resources.activityLogRepo.insert({
+              timestamp: Date.now(), type: 'skipped',
+              message: `Skipped u/${post.author} (already contacted across accounts)`,
+              recipient: post.author,
+            });
+            return false;
+          }
+          let chat;
+          try {
+            chat = await chatService.startConversation(post.author, processed.generatedMessage, post.author_fullname);
+          } catch (error) {
+            this.recipientDeduplicator.release(post.author);
+            throw error;
+          }
+          if (!chat) {
+            this.recipientDeduplicator.release(post.author);
+            return false;
+          }
           postsRepo.markMessageSent(post.id);
           messagesRepo.insert({
             postId: post.id, recipient: post.author, subject: post.author,

src/web/events/express-sse-adapter.ts

@@ -197,6 +197,14 @@ export function createExpressSseHandler(
     }
 
     try {
+      // A first-time subscriber repairs authoritative dashboard snapshots on
+      // open and only needs events published from this point onwards. Replaying
+      // the entire buffer here can overflow the bounded response queue and
+      // force EventSource into a reconnect loop. A genuine reconnect supplies
+      // Last-Event-ID and still receives every buffered event after its cursor.
+      const requestedLastEventId = request.get('Last-Event-ID');
+      const replayCursor = requestedLastEventId
+        ?? options.hub.recent(1).at(-1)?.id;
       subscription = options.hub.subscribe(
         (event) => {
           if (!active) {
@@ -208,7 +216,7 @@ export function createExpressSseHandler(
             close(true);
           }
         },
-        { lastEventId: request.get('Last-Event-ID') },
+        { lastEventId: replayCursor },
       );
     } catch {
       close(true);

tests/chat-service-username-persist.test.ts

@@ -6,7 +6,11 @@ import { runMigrations } from '../src/database/client.js';
 import { RedditUsersRepository } from '../src/database/repositories.js';
 import { ChatService } from '../src/services/chat/service.js';
 import { ChatCache } from '../src/services/chat/cache.js';
-import { MatrixAuthError, MatrixClient } from '../src/services/chat/matrix/client.js';
+import {
+  MatrixAuthError,
+  MatrixClient,
+  MatrixFeatureDisabledError,
+} from '../src/services/chat/matrix/client.js';
 import { createMockLogger } from './mockLogger.js';
 import { authenticatedAccountAuth } from './testUtils.js';
 
@@ -232,4 +236,54 @@ describe('ChatService username persistence', () => {
     expect(matrix.getRoomFullState).toHaveBeenCalledOnce();
     expect(matrix.getRoomMessages).not.toHaveBeenCalled();
   });
+
+  it('stops room state lookups after the homeserver reports the feature is disabled', async () => {
+    const logger = createMockLogger();
+    const cache = tmpCache(logger);
+    cache.set(['first', 'second'].map((name) => ({
+      username: 'unknown',
+      roomName: 'unknown',
+      lastMessageTime: Date.now(),
+      lastMessageSnippet: '',
+      isFromUs: false,
+      unread: false,
+      roomId: `!${name}:reddit.com`,
+      messages: [],
+    })));
+
+    const matrix = buildMatrix();
+    matrix.getRoomFullState = vi.fn().mockRejectedValue(
+      new MatrixFeatureDisabledError('disabled by configuration'),
+    );
+    matrix.getRoomMessages = vi.fn().mockImplementation(async (roomId: string) => ({
+      start: 'start',
+      chunk: [{
+        event_id: `$${roomId}`,
+        type: 'm.room.message',
+        sender: `@t2_${roomId.includes('first') ? 'first' : 'second'}:reddit.com`,
+        origin_server_ts: Date.now(),
+        content: { msgtype: 'm.text', body: 'hello' },
+      }],
+    }));
+    const usernameResolver = { resolveT2Ids: vi.fn().mockResolvedValue({}) };
+    const svc = new ChatService(
+      matrix,
+      logger,
+      undefined, undefined, undefined, usernameResolver,
+      cache,
+      undefined,
+      undefined,
+      authenticatedAccountAuth,
+    );
+
+    await svc.enrichUsernames();
+
+    expect(matrix.getRoomFullState).toHaveBeenCalledOnce();
+    expect(matrix.getRoomMessages).toHaveBeenCalledTimes(2);
+    expect(logger.logs.filter((entry) =>
+      entry.message.includes('room state lookup is disabled upstream'),
+    )).toHaveLength(1);
+    expect((await svc.getCachedConversations()).map((chat) => chat.username))
+      .toEqual(['t2_first', 't2_second']);
+  });
 });

tests/dashboard/conversations.test.tsx

@@ -12,6 +12,7 @@ import { ConversationsPage } from '../../apps/dashboard/src/features/conversatio
 interface ChatFixtureOptions {
   username: string;
   roomId: string;
+  lastMessageTime?: number;
   unread?: boolean;
   isFromUs?: boolean;
   lastMessageSnippet?: string;
@@ -24,7 +25,7 @@ function chatFixture(options: ChatFixtureOptions) {
     roomName: options.username,
     roomId: options.roomId,
     url: `https://chat.reddit.com/room/${options.roomId}`,
-    lastMessageTime: 1_786_000_000_000,
+    lastMessageTime: options.lastMessageTime ?? 1_786_000_000_000,
     lastMessageSnippet: options.lastMessageSnippet ?? `Latest from ${options.username}`,
     isFromUs: options.isFromUs ?? false,
     unread: options.unread ?? false,
@@ -141,6 +142,36 @@ describe('ConversationsPage', () => {
     );
   });
 
+  it('orders conversations by latest message activity', async () => {
+    const oldest = chatFixture({ username: 'oldest', roomId: 'room-oldest', lastMessageTime: 100 });
+    const newest = chatFixture({ username: 'newest', roomId: 'room-newest', lastMessageTime: 300 });
+    const middle = chatFixture({ username: 'middle', roomId: 'room-middle', lastMessageTime: 200 });
+    server.use(http.get('/api/conversations', () => HttpResponse.json([oldest, newest, middle])));
+    renderConversations();
+
+    await screen.findByRole('button', { name: /u\/newest/ });
+    expect(screen.getAllByRole('button', { name: /u\/(?:oldest|newest|middle)/ }).map((button) => button.getAttribute('aria-label')))
+      .toEqual([
+        expect.stringContaining('u/newest'),
+        expect.stringContaining('u/middle'),
+        expect.stringContaining('u/oldest'),
+      ]);
+  });
+
+  it('shows short relative times for the latest message', async () => {
+    const now = Date.now();
+    const minutesAgo = chatFixture({ username: 'minutes', roomId: 'room-minutes', lastMessageTime: now - (5 * 60_000) });
+    const daysAgo = chatFixture({ username: 'days', roomId: 'room-days', lastMessageTime: now - (2 * 86_400_000) });
+    server.use(http.get('/api/conversations', () => HttpResponse.json([daysAgo, minutesAgo])));
+    renderConversations();
+
+    const recentTime = await screen.findByText('5m ago');
+    expect(recentTime.tagName).toBe('TIME');
+    expect(recentTime).toHaveAttribute('dateTime', new Date(minutesAgo.lastMessageTime).toISOString());
+    expect(recentTime).toHaveAttribute('title');
+    expect(screen.getByText('2d ago')).toBeInTheDocument();
+  });
+
   it('marks and filters conversations with received images and renders the images in chat', async () => {
     const imageChat = chatFixture({
       username: 'alice',

tests/dashboard/media.test.tsx

@@ -150,6 +150,20 @@ describe('media page', () => {
     expect(screen.getByText('No media matches these filters.')).toBeInTheDocument();
   });
 
+  it('orders media by received time', async () => {
+    server.use(
+      http.get('/api/media', () => HttpResponse.json([mediaItems[2], mediaItems[0], mediaItems[1]])),
+      http.get('/api/media/sync', () => HttpResponse.json(idleStatus)),
+    );
+    renderMedia();
+
+    expect((await screen.findAllByRole('img')).map((item) => item.getAttribute('alt'))).toEqual([
+      'Media from alice',
+      'Media from charlie',
+      'Media from dave',
+    ]);
+  });
+
   it('shows empty and recoverable error states', async () => {
     let requests = 0;
     server.use(

tests/matrix-client.test.ts

@@ -2,6 +2,7 @@ import { describe, it, expect, vi } from 'vitest';
 import {
   MatrixAuthError,
   MatrixClient,
+  MatrixFeatureDisabledError,
   MatrixRateLimitError,
 } from '../src/services/chat/matrix/client.js';
 import { createMockLogger } from './mockLogger.js';
@@ -153,6 +154,18 @@ describe('MatrixClient direct room registration', () => {
 });
 
 describe('MatrixClient authentication classification', () => {
+  it('classifies an explicitly disabled endpoint as an unavailable feature', async () => {
+    const client = new MatrixClient(creds, createMockLogger(), {
+      minRequestIntervalMs: 0,
+      fetchImpl: vi.fn().mockResolvedValue(new Response(JSON.stringify({
+        message: 'disabled by configuration',
+      }), { status: 403, headers: { 'content-type': 'application/json' } })),
+    });
+
+    await expect(client.getRoomFullState('!room:example.test'))
+      .rejects.toBeInstanceOf(MatrixFeatureDisabledError);
+  });
+
   it('does not classify a room-level 403 as an expired account token', async () => {
     const client = new MatrixClient(creds, createMockLogger(), {
       minRequestIntervalMs: 0,

tests/recipient-deduplicator.test.ts

@@ -0,0 +1,29 @@
+import { describe, expect, it, vi } from 'vitest';
+import { RecipientDeduplicator } from '../src/services/recipient-deduplicator.js';
+
+describe('RecipientDeduplicator', () => {
+  it('reserves a recipient once across username casing variants', () => {
+    const history = { hasSentTo: vi.fn(() => false) };
+    const deduplicator = new RecipientDeduplicator(history);
+
+    expect(deduplicator.tryReserve('Some_User')).toBe(true);
+    expect(deduplicator.hasSentTo('some_user')).toBe(true);
+    expect(deduplicator.tryReserve('SOME_USER')).toBe(false);
+  });
+
+  it('rejects recipients found in persisted cross-account history', () => {
+    const history = { hasSentTo: vi.fn((recipient: string) => recipient === 'contacted') };
+    const deduplicator = new RecipientDeduplicator(history);
+
+    expect(deduplicator.tryReserve('contacted')).toBe(false);
+    expect(deduplicator.tryReserve('new-user')).toBe(true);
+  });
+
+  it('allows another account to retry after a failed send releases its reservation', () => {
+    const deduplicator = new RecipientDeduplicator({ hasSentTo: () => false });
+
+    expect(deduplicator.tryReserve('retry-user')).toBe(true);
+    deduplicator.release('RETRY-USER');
+    expect(deduplicator.tryReserve('retry-user')).toBe(true);
+  });
+});

tests/repository-account-isolation.test.ts

@@ -9,6 +9,7 @@ import {
   DeliveryOutboxRepository,
   MessagesRepository,
   PostsRepository,
+  RecipientHistoryRepository,
   SuccessfulMessagesRepository,
 } from '../src/database/repositories.js';
 import { buildConversationState } from '../src/services/conversation-state.js';
@@ -75,6 +76,8 @@ describe('account-bound domain repositories', () => {
     expect(messagesB.getByPostId('same-post')).toMatchObject({ id: messageB, message: 'from B' });
     expect(messagesA.hasSentTo('only-a')).toBe(true);
     expect(messagesB.hasSentTo('only-a')).toBe(false);
+    const recipientHistory = new RecipientHistoryRepository(db);
+    expect(recipientHistory.hasSentTo('ONLY-A')).toBe(true);
     expect(messagesA.getByChatRoomId('same-room')?.recipient).toBe('only-a');
     expect(messagesB.getByChatRoomId('same-room')).toBeUndefined();
 

tests/web/events/express-sse-adapter.test.ts

@@ -122,7 +122,7 @@ describe('createExpressSseHandler', () => {
     ]);
   });
 
-  it('replays the full available window when Last-Event-ID is absent', () => {
+  it('starts at the live edge when Last-Event-ID is absent', () => {
     const hub = createHub();
     hub.publish('log.created', { level: 'info', message: 'one' });
     hub.publish('log.created', { level: 'warn', message: 'two' });
@@ -134,10 +134,12 @@ describe('createExpressSseHandler', () => {
       vi.fn(),
     );
 
+    expect(response.frames).toEqual([': connected\n\n']);
+
+    hub.publish('log.created', { level: 'info', message: 'live' });
     expect(response.frames.map((frame) => frame.split('\n')[0])).toEqual([
       ': connected',
-      'id: event-1',
+      'id: event-3',
-      'id: event-2',
     ]);
   });