feat: persist settings and enrich conversation context

agents.md

@@ -19,20 +19,11 @@ Refactor code to improve maintainability, testability, and clarity. Break down l
 - **Zod Validation**: Use `zod` (already in deps) to validate external data (config files, API responses).
 - **Async/Await**: properly handle promises. Use `p-queue` or `p-retry` for rate-limited operations.
 
-### 4. Test-Driven Development (TDD) — REQUIRED
-All new functionality and bug fixes MUST follow the red-green-refactor cycle. This is non-negotiable.
-
-- **Red**: Write a failing test FIRST that describes the desired behavior. Run it and confirm it fails for the expected reason.
-- **Green**: Write the minimum production code needed to make the test pass. No extra features, no speculative abstractions.
-- **Refactor**: With tests green, clean up implementation and tests. Re-run the suite after each change.
-
-**Rules**:
-- Never commit production code without an accompanying test that fails without it.
+### 4. Testing
+- TDD is not required. Agents may implement changes before writing or updating tests.
+- Add or update tests when they provide useful coverage for new functionality or bug fixes.
 - Tests live in `tests/` (mirroring `src/` structure) and run via `vitest` (`npm test`).
-- Use dependency injection so collaborators (DB, HTTP, browser, clock) can be faked — do not mock what you don't own; wrap third-party APIs in a thin interface and fake the interface.
 - Prefer behavior-focused tests (inputs → outputs / observable side effects) over tests that pin internal structure.
-- Bug fixes start with a regression test that reproduces the bug.
-- If a change is genuinely untestable (e.g. a one-line config tweak), state that explicitly in the PR/commit rather than skipping silently.
 
 ### 5. Project Specifics
 - **Tech Stack**: Node.js, TypeScript, Playwright, Express, SQLite, Vitest.
@@ -45,10 +36,10 @@ All new functionality and bug fixes MUST follow the red-green-refactor cycle. Th
 
 ## Workflow for Agents
 1. **Analyze**: Before writing code, read the file and understand the context.
-2. **Plan**: Identify what needs to change. Check if the change violates SRP. Identify the test(s) that will drive the change.
-3. **Write failing test (Red)**: Add a vitest spec that captures the new behavior or reproduces the bug. Run `npm test` and confirm it fails for the right reason.
-4. **Implement (Green)**: Write the smallest change that makes the test pass. Create new small files when SRP calls for it.
-5. **Refactor**: Tidy the implementation and the test with the suite green. Re-run tests after each refactor step.
-6. **Verify**: Ensure the full suite passes (`npm test`) and types check (`npm run build` or `tsc --noEmit`).
+2. **Plan**: Identify what needs to change and check if the change violates SRP.
+3. **Implement**: Make the scoped change. Create new small files when SRP calls for it.
+4. **Test**: Add or update useful tests as appropriate for the change.
+5. **Refactor**: Tidy the implementation and tests while preserving behavior.
+6. **Verify**: Run the relevant tests and type checks (`npm run build` or `tsc --noEmit`) in proportion to the change.
 
-You must use the dokploy credentials in .env for access to dokploy
+You must use the dokploy credentials in .env for access to dokploy

apps/dashboard/src/components/origin-post.tsx

@@ -0,0 +1,72 @@
+import { useEffect, useRef, useState, type ReactNode } from 'react';
+
+export interface OriginPost {
+  title: string;
+  url: string;
+  imageUrl?: string | null;
+  subreddit?: string;
+}
+
+export function OriginPostCard({ post }: { post: OriginPost }) {
+  return (
+    <a aria-label={post.title} className="origin-post-card" href={post.url} rel="noreferrer" target="_blank">
+      {post.imageUrl ? <img alt={`Source post: ${post.title}`} loading="lazy" src={post.imageUrl} /> : null}
+      <span>
+        <small>Started from {post.subreddit ? `r/${post.subreddit}` : 'Reddit'}</small>
+        <strong>{post.title}</strong>
+        <span>Open original post</span>
+      </span>
+    </a>
+  );
+}
+
+export function OriginPostButton({ children, post }: { children: ReactNode; post: OriginPost }) {
+  const [isOpen, setIsOpen] = useState(false);
+  const triggerRef = useRef<HTMLButtonElement>(null);
+  const closeRef = useRef<HTMLButtonElement>(null);
+
+  useEffect(() => {
+    if (!isOpen) return;
+    closeRef.current?.focus();
+    const closeOnEscape = (event: KeyboardEvent) => {
+      if (event.key === 'Escape') setIsOpen(false);
+    };
+    document.addEventListener('keydown', closeOnEscape);
+    return () => document.removeEventListener('keydown', closeOnEscape);
+  }, [isOpen]);
+
+  function close() {
+    setIsOpen(false);
+    queueMicrotask(() => triggerRef.current?.focus());
+  }
+
+  return (
+    <>
+      <button className="origin-post-trigger" onClick={() => setIsOpen(true)} ref={triggerRef} type="button">
+        {children}
+      </button>
+      {isOpen ? (
+        <div
+          aria-labelledby="origin-post-dialog-title"
+          aria-modal="true"
+          className="origin-post-backdrop"
+          onMouseDown={(event) => { if (event.target === event.currentTarget) close(); }}
+          role="dialog"
+        >
+          <article className="origin-post-dialog">
+            <div className="origin-post-dialog-heading">
+              <span>Conversation origin</span>
+              <button aria-label="Close source post" onClick={close} ref={closeRef} type="button">×</button>
+            </div>
+            {post.imageUrl ? <img alt={`Source post: ${post.title}`} loading="lazy" src={post.imageUrl} /> : null}
+            <div className="origin-post-dialog-copy">
+              {post.subreddit ? <small>r/{post.subreddit}</small> : null}
+              <h2 id="origin-post-dialog-title">{post.title}</h2>
+              <a className="button primary" href={post.url} rel="noreferrer" target="_blank">Open Reddit post</a>
+            </div>
+          </article>
+        </div>
+      ) : null}
+    </>
+  );
+}

apps/dashboard/src/components/reddit-user-text.tsx

@@ -0,0 +1,16 @@
+import { Fragment } from 'react';
+import { RedditUsernameLink } from './reddit-username-link.js';
+
+const USER_MENTION = /(u\/[A-Za-z0-9_-]+|@?t2_[A-Za-z0-9]+(?::reddit\.com)?)/gi;
+
+export function RedditUserText({ children }: { children: string }) {
+  return children.split(USER_MENTION).map((part, index) => {
+    if (/^u\/(?!t2_)[A-Za-z0-9_-]+$/i.test(part)) {
+      return <RedditUsernameLink key={`${part}-${index}`} username={part} />;
+    }
+    if (/^(?:@?t2_)/i.test(part) || /^u\/t2_/i.test(part)) {
+      return <Fragment key={`${part}-${index}`}>Reddit user</Fragment>;
+    }
+    return <Fragment key={`${part}-${index}`}>{part}</Fragment>;
+  });
+}

apps/dashboard/src/components/reddit-username-link.tsx

@@ -0,0 +1,42 @@
+export interface RedditUsernameLinkProps {
+  username: string;
+  showPrefix?: boolean;
+}
+
+export function normalizeRedditUsername(username: string): string {
+  return username.trim().replace(/^\/?u\//i, '');
+}
+
+export function isDisplayableRedditUsername(username: string): boolean {
+  const normalized = normalizeRedditUsername(username);
+  return normalized.length > 0
+    && !/^(?:me|you|unknown|unknown reddit user)$/i.test(normalized)
+    && !/^t2_/i.test(normalized)
+    && !/^@t2_/i.test(normalized);
+}
+
+export function redditUsernameLabel(username: string, showPrefix = true): string {
+  if (!isDisplayableRedditUsername(username)) return 'Unknown Reddit user';
+  const normalized = normalizeRedditUsername(username);
+  return showPrefix ? `u/${normalized}` : normalized;
+}
+
+export function RedditUsernameLink({ username, showPrefix = true }: RedditUsernameLinkProps) {
+  const normalizedUsername = normalizeRedditUsername(username);
+  const label = redditUsernameLabel(username, showPrefix);
+
+  if (!isDisplayableRedditUsername(username)) {
+    return <span className="reddit-username-link is-unresolved">{label}</span>;
+  }
+
+  return (
+    <a
+      className="reddit-username-link"
+      href={`https://www.reddit.com/u/${encodeURIComponent(normalizedUsername)}`}
+      rel="noreferrer"
+      target="_blank"
+    >
+      {label}
+    </a>
+  );
+}

apps/dashboard/src/features/conversations/conversation-api.ts

@@ -44,7 +44,10 @@ export function createConversationApi(fetchImplementation?: typeof fetch): Conve
 
   return {
     async list() {
-      return parseResponse(await request('/api/conversations'), ConversationsResponseSchema);
+      return parseResponse(
+        await request('/api/conversations?includeImageMetadata=true'),
+        ConversationsResponseSchema,
+      );
     },
     async detail(id) {
       return parseResponse(await request(conversationPath(id)), ConversationDetailResponseSchema);

apps/dashboard/src/features/conversations/conversation-detail.tsx

@@ -1,5 +1,7 @@
 import { useCallback, useRef, useState } from 'react';
 import type { ConversationDetailResponse } from '../../../../../packages/api-contracts/src/index.js';
+import { RedditUsernameLink, redditUsernameLabel } from '../../components/reddit-username-link.js';
+import { OriginPostCard } from '../../components/origin-post.js';
 import { useConversationDetailQuery, useSendReplyMutation, useSuggestMediaAskMutation, useSuggestReplyMutation } from './conversation-queries.js';
 import { SendConfirmationDialog } from './send-confirmation-dialog.js';
 
@@ -12,6 +14,10 @@ function formatMessageTime(timestamp: number): string {
   return new Intl.DateTimeFormat(undefined, { dateStyle: 'medium', timeStyle: 'short' }).format(timestamp);
 }
 
+function mediaPath(localPath: string): string {
+  return `/media/${localPath.split('/').map(encodeURIComponent).join('/')}`;
+}
+
 function MessageHistory({ conversation }: { conversation: ConversationDetailResponse }) {
   if (!conversation.messages || conversation.messages.length === 0) {
     return <div className="conversation-empty-detail">No messages have been loaded for this conversation.</div>;
@@ -22,10 +28,22 @@ function MessageHistory({ conversation }: { conversation: ConversationDetailResp
       {conversation.messages.map((message) => (
         <li className={message.isSelf ? 'is-self' : 'is-recipient'} key={`${message.timestamp}-${message.sender}-${message.text}`}>
           <div>
-            <strong>{message.isSelf ? 'You' : `u/${conversation.username}`}</strong>
+            <strong>{message.isSelf ? 'You' : <RedditUsernameLink username={conversation.username} />}</strong>
             <time dateTime={new Date(message.timestamp).toISOString()}>{formatMessageTime(message.timestamp)}</time>
           </div>
           <p>{message.text}</p>
+          {message.media?.length ? (
+            <div className="conversation-message-images">
+              {message.media.map((media) => (
+                <img
+                  alt={`Image ${message.isSelf ? 'sent by you' : `received from ${redditUsernameLabel(conversation.username)}`}`}
+                  key={`${message.timestamp}-${media.localPath}`}
+                  loading="lazy"
+                  src={mediaPath(media.localPath)}
+                />
+              ))}
+            </div>
+          ) : null}
         </li>
       ))}
     </ol>
@@ -79,7 +97,7 @@ function ConversationComposer({ conversation }: { conversation: ConversationDeta
           {mediaAskMutation.isPending ? 'Generating media ask…' : 'Suggest media ask'}
         </button>
       </div>
-      <label className="sr-only" htmlFor="conversation-reply">Reply to u/{conversation.username}</label>
+      <label className="sr-only" htmlFor="conversation-reply">Reply to {redditUsernameLabel(conversation.username)}</label>
       <textarea
         id="conversation-reply"
         onChange={(event) => {
@@ -94,7 +112,7 @@ function ConversationComposer({ conversation }: { conversation: ConversationDeta
       {mediaAskMutation.isError ? <div className="conversation-inline-error" role="alert">{mediaAskMutation.error.message}</div> : null}
       {sendMutation.isError ? <div className="conversation-inline-error" role="alert">{sendMutation.error.message}</div> : null}
       {wasSent ? (
-        <div aria-label="Reply sent" className="conversation-inline-success" role="status">Reply sent to u/{conversation.username}</div>
+        <div aria-label="Reply sent" className="conversation-inline-success" role="status">Reply sent to <RedditUsernameLink username={conversation.username} /></div>
       ) : null}
       <div className="conversation-actions">
         <span>{draft.length} characters</span>
@@ -143,7 +161,7 @@ export function ConversationDetail({ conversationId, onClose }: ConversationDeta
       <header>
         <div>
           <span className="conversation-eyebrow">Conversation</span>
-          <h2>u/{conversation.username}</h2>
+          <h2><RedditUsernameLink username={conversation.username} /></h2>
           {conversation.unread ? <span className="conversation-badge">Unread</span> : null}
         </div>
         <button aria-label="Close conversation" onClick={onClose} type="button">Close</button>
@@ -154,16 +172,14 @@ export function ConversationDetail({ conversationId, onClose }: ConversationDeta
         </div>
       ) : null}
       {conversation.triggeringPost ? (
-        <a
-          aria-label={conversation.triggeringPost.title ?? `Open triggering post ${conversation.triggeringPost.id}`}
-          className="triggering-post"
-          href={conversation.triggeringPost.url}
-          rel="noreferrer"
-          target="_blank"
-        >
-          <span>Started from {conversation.triggeringPost.subreddit ? `r/${conversation.triggeringPost.subreddit}` : 'Reddit'}</span>
-          <strong>{conversation.triggeringPost.title ?? conversation.triggeringPost.id}</strong>
-        </a>
+        <div className="triggering-post">
+          <OriginPostCard post={{
+            title: conversation.triggeringPost.title ?? conversation.triggeringPost.id,
+            url: conversation.triggeringPost.url,
+            imageUrl: conversation.triggeringPost.imageUrl,
+            subreddit: conversation.triggeringPost.subreddit,
+          }} />
+        </div>
       ) : null}
       <MessageHistory conversation={conversation} />
       <ConversationComposer conversation={conversation} />

apps/dashboard/src/features/conversations/conversation-route.tsx

@@ -8,7 +8,12 @@ export function ConversationRoute() {
   const filterValue = searchParams.get('filter');
   const filters: ConversationFilters = {
     search: searchParams.get('q') ?? '',
-    filter: filterValue === 'unread' || filterValue === 'awaiting-reply' ? filterValue : 'all',
+    filter:
+      filterValue === 'unread'
+      || filterValue === 'awaiting-reply'
+      || filterValue === 'received-images'
+        ? filterValue
+        : 'all',
   };
 
   function selectConversation(nextConversationId: string | null) {

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

@@ -1,12 +1,13 @@
 import { 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';
 import { useConversationsQuery } from './conversation-queries.js';
 import { StartConversationForm } from './start-conversation-form.js';
 import { ProcessedUserLookup } from './processed-user-lookup.js';
 import './conversations.css';
 
-export type ConversationFilter = 'all' | 'unread' | 'awaiting-reply';
+export type ConversationFilter = 'all' | 'unread' | 'awaiting-reply' | 'received-images';
 
 export interface ConversationFilters {
   search: string;
@@ -27,6 +28,7 @@ function conversationId(conversation: ActiveChat): string {
 function matchesFilter(conversation: ActiveChat, filter: ConversationFilter): boolean {
   if (filter === 'unread') return conversation.unread;
   if (filter === 'awaiting-reply') return conversation.isFromUs;
+  if (filter === 'received-images') return conversation.hasReceivedImages === true;
   return true;
 }
 
@@ -37,17 +39,17 @@ function ConversationListItem({ conversation, isSelected, onSelect }: {
 }) {
   const state = conversation.unread ? 'Unread' : conversation.isFromUs ? 'Awaiting reply' : 'Up to date';
   return (
-    <li>
+    <li className={isSelected ? 'conversation-list-item is-selected' : 'conversation-list-item'}>
       <button
-        aria-label={`u/${conversation.username}, ${state}`}
+        aria-label={`${redditUsernameLabel(conversation.username)}, ${state}${conversation.hasReceivedImages ? ', Image received' : ''}`}
         aria-pressed={isSelected}
-        className={isSelected ? 'conversation-list-item is-selected' : 'conversation-list-item'}
+        className="conversation-list-target"
         onClick={onSelect}
         type="button"
-      >
-        <span className="conversation-list-heading"><strong>u/{conversation.username}</strong><small>{state}</small></span>
-        <span>{conversation.lastMessageSnippet || 'No message preview'}</span>
-      </button>
+      />
+      <span className="conversation-list-heading"><strong><RedditUsernameLink username={conversation.username} /></strong><small>{state}</small></span>
+      {conversation.hasReceivedImages ? <span className="conversation-image-marker">Image received</span> : null}
+      <span>{conversation.lastMessageSnippet || 'No message preview'}</span>
     </li>
   );
 }
@@ -121,6 +123,7 @@ export function ConversationsPage({ selectedConversationId, onSelectedConversati
               <option value="all">All</option>
               <option value="unread">Unread</option>
               <option value="awaiting-reply">Awaiting reply</option>
+              <option value="received-images">Received images</option>
             </select>
           </div>
           {conversationsQuery.isPending ? (

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

@@ -33,12 +33,17 @@
 .conversation-master, .conversation-detail-panel { min-width: 0; background: var(--surface); border: 1px solid var(--border); border-radius: .9rem; overflow: hidden; }
 .conversation-toolbar { display: grid; grid-template-columns: minmax(0, 1fr) auto; gap: .5rem; padding: .75rem; border-bottom: 1px solid var(--border); }
 .conversation-list { display: grid; gap: .35rem; max-height: 46rem; padding: .5rem; margin: 0; overflow: auto; list-style: none; }
-.conversation-list-item { display: grid; gap: .4rem; width: 100%; padding: .8rem !important; text-align: left; background: transparent !important; border-color: transparent !important; }
-.conversation-list-item:hover { background: var(--surface-raised) !important; }
-.conversation-list-item.is-selected { background: var(--accent-dark) !important; border-color: #28593d !important; }
+.conversation-list-item { position: relative; display: grid; gap: .4rem; width: 100%; padding: .8rem; text-align: left; background: transparent; border: 1px solid transparent; border-radius: .6rem; }
+.conversation-list-item:hover { background: var(--surface-raised); }
+.conversation-list-item.is-selected { background: var(--accent-dark); border-color: #28593d; }
+.conversation-list-target { position: absolute; inset: 0; z-index: 0; min-height: 0 !important; padding: 0 !important; background: transparent !important; border: 0 !important; }
+.conversation-list-target:focus-visible { outline: 2px solid var(--accent); outline-offset: -2px; }
+.conversation-list-item > span { position: relative; z-index: 1; pointer-events: none; }
+.conversation-list-item .reddit-username-link { pointer-events: auto; }
 .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-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; }
 .conversation-detail { min-height: 32rem; }
@@ -46,8 +51,7 @@
 .conversation-detail h2 { display: inline; margin-right: .6rem; }
 .conversation-badge { display: inline-flex; padding: .2rem .45rem; color: #aaf0c4; background: #163a26; border-radius: 999px; font-size: .7rem; font-weight: 800; }
 .conversation-sync-notice { padding: .75rem 1rem; color: #ffe1a0; background: #2a2111; border-bottom: 1px solid #59451e; }
-.triggering-post { display: grid; gap: .2rem; margin: 1rem; padding: .75rem; color: inherit; background: var(--surface-raised); border: 1px solid var(--border); border-radius: .65rem; text-decoration: none; }
-.triggering-post span { color: var(--muted); font-size: .75rem; }
+.triggering-post { margin: 1rem; padding: .75rem; background: var(--surface-raised); border: 1px solid var(--border); border-radius: .65rem; }
 .conversation-messages { display: grid; gap: .75rem; max-height: 30rem; padding: 1rem; margin: 0; overflow: auto; list-style: none; }
 .conversation-messages li { max-width: 85%; padding: .7rem .8rem; border-radius: .8rem; }
 .conversation-messages li.is-self { justify-self: end; background: var(--accent-dark); }
@@ -55,6 +59,8 @@
 .conversation-messages li > div { display: flex; justify-content: space-between; gap: 1rem; margin-bottom: .35rem; }
 .conversation-messages time { color: var(--muted); font-size: .7rem; }
 .conversation-messages p { margin: 0; line-height: 1.45; white-space: pre-wrap; }
+.conversation-message-images { display: grid; grid-template-columns: repeat(auto-fit, minmax(min(12rem, 100%), 1fr)); gap: .5rem; margin-top: .65rem; }
+.conversation-message-images img { display: block; width: 100%; max-width: 28rem; max-height: 32rem; object-fit: contain; background: #08100c; border: 1px solid var(--border); border-radius: .6rem; }
 .conversation-empty-detail { padding: 2rem; color: var(--muted); text-align: center; }
 .conversation-composer { display: grid; gap: .65rem; padding: 1rem; border-top: 1px solid var(--border); }
 .conversation-section-heading, .conversation-actions { display: flex; align-items: center; justify-content: space-between; gap: .75rem; }

apps/dashboard/src/features/conversations/processed-user-lookup.tsx

@@ -1,4 +1,5 @@
 import { useState } from 'react';
+import { RedditUsernameLink, redditUsernameLabel } from '../../components/reddit-username-link.js';
 import { useProcessedPostsQuery } from './conversation-queries.js';
 
 export function ProcessedUserLookup() {
@@ -17,8 +18,8 @@ export function ProcessedUserLookup() {
       {postsQuery.isPending && username ? <p role="status">Looking up processed posts…</p> : null}
       {postsQuery.isError ? <p role="alert">{postsQuery.error.message}</p> : null}
       {postsQuery.data ? (
-        postsQuery.data.length === 0 ? <p>No processed posts found for u/{username}.</p> : (
-          <ol aria-label={`Processed posts for u/${username}`}>
+        postsQuery.data.length === 0 ? <p>No processed posts found for <RedditUsernameLink username={username} />.</p> : (
+          <ol aria-label={`Processed posts for ${redditUsernameLabel(username)}`}>
             {postsQuery.data.map((post) => <li key={post.id}><strong>{post.title}</strong><span>r/{post.subreddit} · {post.messageSent ? 'Message sent' : post.error ?? 'Processed'}</span></li>)}
           </ol>
         )

apps/dashboard/src/features/conversations/start-conversation-form.tsx

@@ -1,4 +1,5 @@
 import { useState } from 'react';
+import { RedditUsernameLink } from '../../components/reddit-username-link.js';
 import { useStartConversationMutation } from './conversation-queries.js';
 
 interface StartConversationFormProps {
@@ -53,7 +54,7 @@ export function StartConversationForm({ onStarted }: StartConversationFormProps)
       {mutation.isError ? <div className="conversation-inline-error" role="alert">{mutation.error.message}</div> : null}
       {successUsername ? (
         <div aria-label="Conversation started" className="conversation-inline-success" role="status">
-          Conversation started with u/{successUsername}
+          Conversation started with <RedditUsernameLink username={successUsername} />
         </div>
       ) : null}
       <button className="conversation-primary" disabled={!canSubmit} type="submit">

apps/dashboard/src/features/media/media-card.tsx

@@ -1,4 +1,5 @@
 import type { MediaItem } from '../../../../../packages/api-contracts/src/index.js';
+import { RedditUsernameLink } from '../../components/reddit-username-link.js';
 import { mediaConversation, mediaType } from './filters.js';
 
 interface MediaCardProps {
@@ -29,8 +30,10 @@ export function MediaCard({ item, isRevealed, onToggleReveal, onOpenPreview }: M
       </div>
       <div className="media-card-body">
         <div>
-          <strong>{item.sender}</strong>
-          <span>{mediaConversation(item)}</span>
+          <strong><RedditUsernameLink showPrefix={false} username={item.sender} /></strong>
+          <span>{item.chatUsername
+            ? <RedditUsernameLink showPrefix={false} username={item.chatUsername} />
+            : mediaConversation(item)}</span>
         </div>
         <dl>
           <div><dt>Type</dt><dd>{mediaType(item) === 'gif' ? 'GIF' : 'Image'}</dd></div>

apps/dashboard/src/features/media/media.css

@@ -25,9 +25,9 @@
 .media-card-body dt { color: var(--muted); }
 .media-card-body dd { margin: 0; text-align: right; }
 .media-reveal { width: 100%; }
-.media-preview-dialog-backdrop { position: fixed; inset: 0; z-index: 70; display: grid; place-items: center; padding: 1rem; background: rgba(0, 0, 0, .88); }
-.media-preview-dialog-content { position: relative; display: grid; place-items: center; width: min(100%, 90rem); height: min(100%, 90rem); }
-.media-preview-dialog-image { display: block; max-width: 100%; max-height: 100%; object-fit: contain; }
+.media-preview-dialog-backdrop { position: fixed; inset: 0; z-index: 70; display: flex; align-items: center; justify-content: center; padding: 1rem; background: rgba(0, 0, 0, .88); }
+.media-preview-dialog-content { position: relative; display: flex; align-items: center; justify-content: center; width: 100%; height: 100%; }
+.media-preview-dialog-image { display: block; width: auto; height: auto; max-width: 100%; max-height: 100%; object-fit: contain; }
 .media-preview-dialog-close { position: absolute; top: .5rem; right: .5rem; width: 2.75rem; height: 2.75rem; padding: 0; border: 1px solid rgba(255, 255, 255, .5); border-radius: 50%; color: white; background: rgba(0, 0, 0, .7); font-size: 2rem; line-height: 1; cursor: pointer; }
 .media-preview-dialog-close:focus-visible { outline: 2px solid var(--accent); outline-offset: 3px; }
 

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

@@ -1,6 +1,9 @@
 import { useEffect, useReducer, useRef, useState } from 'react';
 import type { ActivityItem, ChatSyncStatus, DashboardEvent } from '../../../../../packages/api-contracts/src/index.js';
 import { useDashboardRealtime } from '../../app/realtime-provider.js';
+import { RedditUsernameLink } from '../../components/reddit-username-link.js';
+import { RedditUserText } from '../../components/reddit-user-text.js';
+import { OriginPostButton } from '../../components/origin-post.js';
 import {
   createLiveConsoleState,
   reduceLiveConsoleState,
@@ -27,7 +30,11 @@ function ActivityView({ items }: { items: readonly ActivityItem[] }) {
       {items.map((item) => (
         <li key={`${item.timestamp}-${item.message}`}>
           <span className={`activity-marker ${item.type}`} aria-hidden="true" />
-          <div><strong>{item.message}</strong><small>{formatTimestamp(item.timestamp)}{item.recipient ? ` · u/${item.recipient}` : ''}</small></div>
+          <div><strong>{item.postUrl && item.postTitle ? (
+            <OriginPostButton post={{ title: item.postTitle, url: item.postUrl, imageUrl: item.imageUrl }}>
+              {item.message}
+            </OriginPostButton>
+          ) : <RedditUserText>{item.message}</RedditUserText>}</strong><small>{formatTimestamp(item.timestamp)}{item.recipient && !item.message.includes(`u/${item.recipient}`) ? <> · <RedditUsernameLink username={item.recipient} /></> : null}</small></div>
         </li>
       ))}
     </ol>
@@ -167,7 +174,7 @@ export function OperationsPage({ realtimeEnabled = true }: OperationsPageProps)
         {consoleClearNotice ? <p role="status">Cleared from this browser view. Server logs were not deleted.</p> : null}
         <div aria-live="polite" className="live-console" role="log">
           {logsQuery.isPending ? <p>Loading logs…</p> : visibleEntries.length === 0 ? <p>No logs match the current filters.</p> : visibleEntries.map((entry) => (
-            <article className={`console-entry ${entry.level}`} key={entry.id}><time dateTime={entry.occurredAt}>{formatTimestamp(entry.occurredAt)}</time><strong>{entry.level.toUpperCase()}</strong><span>{entry.message}</span></article>
+            <article className={`console-entry ${entry.level}`} key={entry.id}><time dateTime={entry.occurredAt}>{formatTimestamp(entry.occurredAt)}</time><strong>{entry.level.toUpperCase()}</strong><span><RedditUserText>{entry.message}</RedditUserText></span></article>
           ))}
           <div ref={consoleEnd} />
         </div>

apps/dashboard/src/features/operations/realtime-client.ts

@@ -124,9 +124,11 @@ export function queryKeysForDashboardEvent(event: DashboardEvent): readonly Quer
       return [['conversations'], ['operations', 'activity']];
     case 'sync.started':
     case 'sync.progress':
+      return [['operations', 'sync-status']];
     case 'sync.completed':
-    case 'sync.failed':
       return [['operations', 'sync-status'], ['conversations'], ['media']];
+    case 'sync.failed':
+      return [['operations', 'sync-status']];
     case 'reddit.session.changed':
       return [['dashboard', 'login', 'status']];
     case 'log.created':

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

@@ -3,6 +3,8 @@ import { useQueryClient } from '@tanstack/react-query';
 import { dashboardQueryKeys, useSetRunningMutation, useStatsQuery, useTimersQuery } from '../../api/queries.js';
 import type { BotStats, Timers } from '../../api/contracts.js';
 import { ConfirmationDialog } from '../../components/confirmation-dialog.js';
+import { RedditUserText } from '../../components/reddit-user-text.js';
+import { OriginPostButton } from '../../components/origin-post.js';
 import { RecentMessagesPanel } from './recent-messages.js';
 
 function errorMessage(error: Error | null): string {
@@ -71,7 +73,11 @@ function ActivityPanel({ stats }: { stats: BotStats }) {
           {stats.recentActivity.map((item) => (
             <li key={`${item.timestamp}-${item.message}`}>
               <span className={`activity-marker ${item.type}`} aria-hidden="true" />
-              <div><strong>{item.message}</strong><small>{formatTime(item.timestamp)}</small></div>
+              <div><strong>{item.postUrl && item.postTitle ? (
+                <OriginPostButton post={{ title: item.postTitle, url: item.postUrl, imageUrl: item.imageUrl }}>
+                  {item.message}
+                </OriginPostButton>
+              ) : <RedditUserText>{item.message}</RedditUserText>}</strong><small>{formatTime(item.timestamp)}</small></div>
             </li>
           ))}
         </ol>

apps/dashboard/src/features/overview/recent-messages.tsx

@@ -1,6 +1,7 @@
 import { useQuery } from '@tanstack/react-query';
 import { MessagesResponseSchema, type SentMessage } from '../../../../../packages/api-contracts/src/index.js';
 import { dashboardRequest } from '../../api/request.js';
+import { RedditUsernameLink } from '../../components/reddit-username-link.js';
 
 async function loadRecentMessages(): Promise<SentMessage[]> {
   const response = await dashboardRequest('/api/messages');
@@ -24,7 +25,7 @@ export function RecentMessagesPanel() {
       {query.data && query.data.length > 0 ? (
         <ol aria-label="Recent sent messages" className="activity-list">
           {query.data.map((message) => (
-            <li key={message.id}><div><strong>u/{message.recipient}</strong><span>{message.message}</span><small>{formatSentAt(message.sentAt)} · {message.gotResponse ? 'Responded' : 'No response recorded'}</small></div></li>
+            <li key={message.id}><div><strong><RedditUsernameLink username={message.recipient} /></strong><span>{message.message}</span><small>{formatSentAt(message.sentAt)} · {message.gotResponse ? 'Responded' : 'No response recorded'}</small></div></li>
           ))}
         </ol>
       ) : null}

apps/dashboard/src/features/settings/access-panel.tsx

@@ -1,4 +1,5 @@
 import { useRef } from 'react';
+import { RedditUsernameLink } from '../../components/reddit-username-link.js';
 import { useImportRedditSessionMutation, useLoginStatusQuery } from './settings-queries.js';
 
 function errorMessage(error: Error | null): string {
@@ -52,7 +53,7 @@ export function AccessPanel() {
     <section aria-labelledby="access-heading" className="panel settings-section">
       <div className="panel-heading"><div><span className="eyebrow">Reddit session</span><h2 id="access-heading">Access</h2></div><span className={session.ready && 'status' in session && session.loggedIn ? 'pill success' : 'pill warning'}>{sessionLabel(session)}</span></div>
       <p className="settings-copy">When Reddit is logged out, account work is paused and waiting for a fresh session dump from the extension.</p>
-      {username ? <p className="settings-copy">Signed in as <strong>u/{username}</strong>.</p> : null}
+      {username ? <p className="settings-copy">Signed in as <strong><RedditUsernameLink username={username} /></strong>.</p> : null}
       <div className="access-actions">
         <input accept="application/json" aria-label="Reddit session export" className="sr-only" onChange={(event) => void importSession(event.target.files?.[0])} ref={importInput} type="file" />
         <button className="button primary" disabled={importMutation.isPending} onClick={() => importInput.current?.click()} type="button">{importMutation.isPending ? 'Importing session…' : 'Import Reddit session'}</button>

apps/dashboard/src/features/settings/settings-editor.tsx

@@ -44,6 +44,7 @@ export function SettingsEditor({ config, section }: SettingsEditorProps) {
       ...response.config,
       subreddits: response.subreddits,
       tones: config.tones,
+      advanced: response.advanced ?? config.advanced,
     };
     const nextDraft = createSettingsDraft(nextConfig);
     setPersistedDraft(nextDraft);

apps/dashboard/src/features/settings/settings-model.ts

@@ -23,6 +23,7 @@ export interface SettingsDraft {
   prioritizeRecentPosts: boolean;
   recentWindowMinutes: string;
   subreddits: SubredditDraft[];
+  advancedConfigJson: string;
 }
 
 export interface ValidatedSettings {
@@ -71,6 +72,7 @@ export function createSettingsDraft(config: ConfigResponse): SettingsDraft {
       tone: subreddit.tone,
       scripted: subreddit.scripted ?? '',
     })),
+    advancedConfigJson: config.advanced ? JSON.stringify(config.advanced, null, 2) : '',
   };
 }
 
@@ -88,6 +90,19 @@ export function validateSettingsDraft(draft: SettingsDraft): SettingsValidationR
   });
   if (Object.keys(requiredErrors).length > 0) return { errors: requiredErrors };
 
+  let advanced: Record<string, unknown> | undefined;
+  if (draft.advancedConfigJson.trim() !== '') {
+    try {
+      const value: unknown = JSON.parse(draft.advancedConfigJson);
+      if (!value || typeof value !== 'object' || Array.isArray(value)) {
+        return { errors: { advancedConfigJson: 'Advanced configuration must be a JSON object.' } };
+      }
+      advanced = value as Record<string, unknown>;
+    } catch {
+      return { errors: { advancedConfigJson: 'Advanced configuration is not valid JSON.' } };
+    }
+  }
+
   const parsed = ValidatedSettingsSchema.safeParse({
     minDelayMinutes: Number(draft.minDelayMinutes),
     maxMessagesPerHour: Number(draft.maxMessagesPerHour),
@@ -125,6 +140,7 @@ export function validateSettingsDraft(draft: SettingsDraft): SettingsValidationR
       recentWindowMinutes: parsed.data.recentWindowMinutes,
     },
     subreddits: parsed.data.subreddits,
+    ...(advanced ? { advanced } : {}),
   });
 
   return {

apps/dashboard/src/features/settings/settings-queries.ts

@@ -20,6 +20,7 @@ export function useSaveSettingsMutation() {
         ...response.config,
         subreddits: response.subreddits,
         tones: current?.tones ?? [],
+        advanced: response.advanced ?? current?.advanced,
       }));
     },
   });

apps/dashboard/src/features/settings/settings-sections.tsx

@@ -204,6 +204,23 @@ export function BehaviourSection({ config, draft, errors, onChange }: SectionPro
           </fieldset>
         ))}
       </div>
+      {config.advanced ? (
+        <div className="advanced-settings">
+          <div><h3>Advanced application configuration</h3><p>Models, prompts, filtering, media sync, and strategy settings. Some changes take effect after a restart.</p></div>
+          <label className="settings-field">
+            <span>Advanced configuration (JSON)</span>
+            <textarea
+              aria-invalid={errors.advancedConfigJson ? 'true' : undefined}
+              aria-label="Advanced configuration JSON"
+              onChange={(event) => onChange({ ...draft, advancedConfigJson: event.target.value })}
+              rows={24}
+              spellCheck={false}
+              value={draft.advancedConfigJson}
+            />
+            {errors.advancedConfigJson ? <small className="field-error">{errors.advancedConfigJson}</small> : null}
+          </label>
+        </div>
+      ) : null}
     </section>
   );
 }

apps/dashboard/src/styles.css

@@ -20,6 +20,8 @@ button, input { font: inherit; }
 button { cursor: pointer; }
 button:disabled { cursor: wait; opacity: .6; }
 a { color: inherit; }
+.reddit-username-link { color: var(--accent); text-decoration: underline; text-decoration-thickness: .08em; text-underline-offset: .16em; }
+.reddit-username-link:hover { color: #aaf0c4; }
 
 .skip-link { position: fixed; left: 1rem; top: -5rem; z-index: 100; background: white; color: black; padding: .75rem 1rem; border-radius: .5rem; }
 .skip-link:focus { top: 1rem; }
@@ -86,6 +88,22 @@ h2 { margin-bottom: 0; font-size: 1.1rem; }
 .activity-list li { display: flex; align-items: flex-start; gap: .75rem; }
 .activity-list li div { display: grid; gap: .15rem; }
 .activity-list small { color: var(--muted); }
+.origin-post-trigger { padding: 0; color: inherit; background: transparent; border: 0; font: inherit; font-weight: inherit; text-align: left; text-decoration: underline; text-decoration-color: var(--accent); text-underline-offset: .2em; cursor: pointer; }
+.origin-post-trigger:focus-visible { outline: 2px solid var(--accent); outline-offset: 3px; }
+.origin-post-backdrop { position: fixed; inset: 0; z-index: 80; display: grid; place-items: center; padding: 1rem; background: rgba(0, 0, 0, .82); }
+.origin-post-dialog { width: min(34rem, 100%); max-height: calc(100vh - 2rem); overflow: auto; background: var(--surface-raised); border: 1px solid var(--border); border-radius: 1rem; box-shadow: 0 2rem 5rem rgba(0, 0, 0, .5); }
+.origin-post-dialog > img { display: block; width: 100%; max-height: 28rem; object-fit: contain; background: #050907; }
+.origin-post-dialog-heading { display: flex; align-items: center; justify-content: space-between; padding: .65rem .8rem; color: var(--muted); border-bottom: 1px solid var(--border); font-size: .75rem; font-weight: 800; letter-spacing: .08em; text-transform: uppercase; }
+.origin-post-dialog-heading button { width: 2.25rem; height: 2.25rem; padding: 0; color: inherit; background: transparent; border: 0; font-size: 1.6rem; cursor: pointer; }
+.origin-post-dialog-copy { display: grid; gap: .7rem; padding: 1rem; }
+.origin-post-dialog-copy h2 { margin: 0; font-size: 1.25rem; }
+.origin-post-dialog-copy small { color: var(--muted); }
+.origin-post-dialog-copy a { justify-self: start; text-decoration: none; }
+.origin-post-card { display: grid; grid-template-columns: auto minmax(0, 1fr); gap: .8rem; align-items: center; color: inherit; text-decoration: none; }
+.origin-post-card > img { width: 5rem; height: 5rem; object-fit: cover; background: #050907; border-radius: .45rem; }
+.origin-post-card > span { display: grid; gap: .2rem; min-width: 0; }
+.origin-post-card small, .origin-post-card span span { color: var(--muted); font-size: .75rem; }
+.origin-post-card strong { overflow-wrap: anywhere; }
 .activity-marker { flex: 0 0 auto; width: .55rem; height: .55rem; margin-top: .3rem; border-radius: 50%; background: var(--muted); }
 .activity-marker.sent, .activity-marker.response { background: var(--accent); }
 .activity-marker.error { background: var(--danger); }

docs/api.md

@@ -761,8 +761,8 @@ GET /api/config
     "jitterMs": 15000
   },
   "browser": {
-    "headless": true,
-    "userDataDir": "./data/browser"
+    "sessionDir": "./data/browser-session",
+    "dryRun": false
   },
   "database": {
     "path": "./data/reddit-bot.db"

docs/architecture.md

@@ -182,8 +182,7 @@ RedditBot/
     ├── ai/
     │   └── openrouter.ts  # OpenRouter AI client (image analysis, message gen) (307 lines)
     ├── browser/
-    │   ├── client.ts      # Playwright persistent context + login (302 lines)
-    │   ├── message-page.ts # DM compose page automation + shadow DOM (560 lines)
+    │   ├── client.ts      # Managed Playwright context + imported cookies
     │   └── media-downloader.ts # Playwright-based media downloader (29 lines)
     ├── services/
     │   ├── monitor.ts       # Post discovery service (72 lines)
@@ -319,14 +318,7 @@ Playwright persistent context manager.
 
 - Browser session persistence (cookies/storage)
 - Login verification (multiple UI checks + API fallback)
-- Automated login flow (form fill, 2FA/captcha detection)
-- Debug screenshot capture on login failure
-
-#### MessagePage (`src/browser/message-page.ts`)
-
-Reddit DM compose page automation.
-
-- Fills recipient/subject/body fields
+- Extension-dump cookie import; no login form automation
 - Extensive Shadow DOM support for `faceplate-*` components
 - Detects recipient errors, verifies submission success
 - Supports dry-run mode for testing
@@ -653,9 +645,7 @@ All endpoints are served by the Express server at `http://localhost:{port}`.
 1. **`config.yaml`** - Primary configuration file (project root)
 2. **Environment Variables** - Override specific fields:
    - `OPENROUTER_API_KEY` - OpenRouter API key
-   - `REDDIT_USERNAME` - Reddit username
-   - `REDDIT_PASSWORD` - Reddit password
-   - `BROWSER_HEADLESS` - Browser headless mode (`true`/`false`)
+   - `WEB_DASHBOARD_TOKEN` - Dashboard access token
 
 ### Configuration Schema (Zod-Validated)
 
@@ -680,8 +670,8 @@ All endpoints are served by the Express server at `http://localhost:{port}`.
     jitterMs: number            // Random jitter range
   }
   browser: {
-    headless: boolean           // Headless mode
-    userDataDir: string         // Persistent session directory
+    sessionDir: string          // Persistent imported session directory
+    dryRun: boolean             // Prevent outbound delivery
   }
   database: {
     path: string                // SQLite database path
@@ -866,7 +856,7 @@ class RateLimiter {
 
 The project includes full Docker support:
 
-- **`Dockerfile`** - Playwright image with browser, VNC, and frontend/server build tooling
+- **`Dockerfile`** - Playwright image with frontend/server build tooling; no VNC or interactive Chrome process
 - **`docker-compose.yml`** - Service orchestration
 - **`.dockerignore`** - Excludes unnecessary files
 
@@ -879,9 +869,7 @@ Deployment documentation is provided in `DOKPLOY_DEPLOY.md`.
 | Variable | Required | Description |
 |---|---|---|
 | `OPENROUTER_API_KEY` | Yes | OpenRouter API key for AI |
-| `REDDIT_USERNAME` | Yes | Reddit username |
-| `REDDIT_PASSWORD` | Yes | Reddit password |
-| `BROWSER_HEADLESS` | No | Browser headless mode (default: `true`) |
+| `WEB_DASHBOARD_TOKEN` | Yes when dashboard enabled | Dashboard access token |
 
 ### Pre-Deployment Checklist
 

docs/configuration.md

@@ -7,9 +7,9 @@ Complete reference for configuring RedditBot.
 ## Table of Contents
 
 1. [Configuration Overview](#configuration-overview)
-2. [Configuration Files](#configuration-files)
+2. [Configuration Storage](#configuration-storage)
 3. [Environment Variables](#environment-variables)
-4. [config.yaml Reference](#configyaml-reference)
+4. [Application Settings](#application-settings)
 5. [Runtime Configuration](#runtime-configuration)
 6. [Configuration Validation](#configuration-validation)
 7. [Troubleshooting](#troubleshooting)
@@ -25,7 +25,7 @@ RedditBot uses a layered configuration approach:
 │                    Priority Order (High → Low)                │
 ├──────────────────────────────────────────────────────────────┤
 │ 1. Environment Variables                                     │
-│    (OPENROUTER_API_KEY, REDDIT_USERNAME, etc.)               │
+│    (OPENROUTER_API_KEY, WEB_DASHBOARD_TOKEN)                 │
 │                                                              │
 │ 2. config.yaml                                               │
 │    (Primary configuration file)                              │
@@ -37,18 +37,20 @@ RedditBot uses a layered configuration approach:
 
 Configuration is loaded at startup by `loadConfig()` in `src/config/index.ts`, which:
 
-1. Reads `config.yaml` from the project root
-2. Merges environment variable overrides
+1. Reads the singleton `app_config` record from SQLite
+2. Imports `config.yaml` only when upgrading an existing database that has no settings record
 3. Validates the entire configuration tree using Zod
 4. Returns a strongly-typed `Config` object
 
+Application-owned settings are edited from the dashboard and saved to SQLite. `OPENROUTER_API_KEY`, `WEB_DASHBOARD_TOKEN`, and `DATABASE_PATH` remain environment-owned bootstrap values and are never stored in `app_config`.
+
 ---
 
-## Configuration Files
+## Configuration Storage
 
-### config.yaml
+### Legacy config.yaml
 
-The primary configuration file, located at the project root:
+`config.yaml` is retained temporarily as a one-time migration source for existing installations. Once every deployed database contains an `app_config` row, it can be removed in a follow-up release.
 
 ```
 RedditBot/
@@ -79,14 +81,13 @@ data/
 
 ## Environment Variables
 
-Environment variables override corresponding values in `config.yaml`.
+Environment variables provide secrets and bootstrap settings that are intentionally excluded from SQLite.
 
 | Variable | Required | Type | Description | Example |
 |---|---|---|---|---|
 | `OPENROUTER_API_KEY` | Yes | string | OpenRouter API key for AI services | `sk-or-v1-abc123...` |
-| `REDDIT_USERNAME` | Yes | string | Reddit username for authentication | `MyBotUser` |
-| `REDDIT_PASSWORD` | Yes | string | Reddit password for authentication | `secret123` |
-| `BROWSER_HEADLESS` | No | boolean | Run browser in headless mode | `true` or `false` |
+| `WEB_DASHBOARD_TOKEN` | Yes when dashboard enabled | string | Dashboard access token | `long-random-secret` |
+| `DATABASE_PATH` | No | string | SQLite database location | `./data/reddit-bot.db` |
 
 ### Setting Environment Variables
 
@@ -96,9 +97,7 @@ Create a `.env` file in the project root:
 
 ```env
 OPENROUTER_API_KEY=sk-or-v1-abc123...
-REDDIT_USERNAME=MyBotUser
-REDDIT_PASSWORD=secret123
-BROWSER_HEADLESS=true
+WEB_DASHBOARD_TOKEN=long-random-secret
 ```
 
 > **Note**: Add `.env` to `.gitignore` - never commit credentials.
@@ -107,8 +106,7 @@ BROWSER_HEADLESS=true
 
 ```bash
 export OPENROUTER_API_KEY=sk-or-v1-abc123...
-export REDDIT_USERNAME=MyBotUser
-export REDDIT_PASSWORD=secret123
+export WEB_DASHBOARD_TOKEN=long-random-secret
 ```
 
 **Option 3: Docker**
@@ -118,13 +116,16 @@ Pass via `docker-compose.yml` or Docker CLI:
 ```yaml
 environment:
   - OPENROUTER_API_KEY=sk-or-v1-abc123...
-  - REDDIT_USERNAME=MyBotUser
-  - REDDIT_PASSWORD=secret123
+  - WEB_DASHBOARD_TOKEN=long-random-secret
 ```
 
 ---
 
-## config.yaml Reference
+## Application Settings
+
+Use **Settings** in the dashboard for monitoring, rate limits, dry-run behaviour, subreddits, models, prompts, filtering, media sync, and strategy configuration. The advanced JSON editor exposes settings that do not yet have dedicated controls; its payload is validated by the server before it is saved.
+
+The YAML examples below document the legacy field layout used during one-time migration.
 
 Complete reference for every configuration option.
 
@@ -235,13 +236,9 @@ Max messages: 20 per hour
 
 ```yaml
 browser:
-  # Run browser in headless mode (no UI)
-  # Set to false for debugging
-  headless: true
-
-  # Directory for persistent browser data
-  # Cookies and session storage are saved here
-  userDataDir: "./data/browser"
+  # Persistent managed-browser data populated only by verified imports
+  sessionDir: "./data/browser-session"
+  dryRun: false
 ```
 
 **Browser session persistence:**
@@ -412,8 +409,8 @@ All configuration is validated using Zod at startup. Invalid configuration will
 | `rateLimit.minDelayMs` | Must be positive integer |
 | `rateLimit.maxMessagesPerHour` | Must be positive integer |
 | `rateLimit.jitterMs` | Must be non-negative integer |
-| `browser.headless` | Must be boolean |
-| `browser.userDataDir` | Must be non-empty string |
+| `browser.sessionDir` | Must be non-empty string |
+| `browser.dryRun` | Must be boolean |
 | `database.path` | Must be non-empty string |
 | `mediaSync.enabled` | Must be boolean |
 | `mediaSync.intervalMinutes` | Must be positive integer (if enabled) |
@@ -432,8 +429,8 @@ All configuration is validated using Zod at startup. Invalid configuration will
 **Error**: `Invalid config: reddit.subreddits must be a non-empty array`
 **Fix**: Add at least one subreddit to `reddit.subreddits` in `config.yaml`
 
-**Error**: `Invalid config: browser.userDataDir must be a string`
-**Fix**: Ensure `browser.userDataDir` is set in `config.yaml`
+**Error**: `Invalid config: browser.sessionDir must be a string`
+**Fix**: Ensure `browser.sessionDir` is set in `config.yaml`
 
 ---
 
@@ -449,15 +446,15 @@ All configuration is validated using Zod at startup. Invalid configuration will
 3. Verify environment variables are set correctly
 4. Check bot logs for specific validation errors
 
-### Credentials Not Working
+### Account Authentication Not Working
 
-**Symptom**: Browser login fails.
+**Symptom**: Account work remains paused.
 
 **Steps**:
-1. Verify `REDDIT_USERNAME` and `REDDIT_PASSWORD` are correct
-2. Check that the account is not locked or requires 2FA
-3. Try manual login via `npm run login`
-4. Ensure `BROWSER_HEADLESS=false` for debugging login issues
+1. Sign in to Reddit in local Chrome
+2. Open Reddit Chat and wait for the extension badge to show `OK`
+3. Export and upload a fresh combined session dump
+4. Check dashboard logs for Reddit or Matrix identity verification errors
 
 ### AI Not Working
 
@@ -475,9 +472,9 @@ All configuration is validated using Zod at startup. Invalid configuration will
 **Symptom**: Bot stops with "Browser session expired" error.
 
 **Steps**:
-1. Delete `data/browser/` directory
-2. Run `npm run login` to re-authenticate
-3. Restart the bot
+1. Open Reddit Chat in the local Chrome profile containing the extension
+2. Export and upload a fresh session dump
+3. Delete the downloaded dump after verification
 
 ### Port Already in Use
 

docs/data-flow.md

@@ -791,21 +791,14 @@ The historical diagram below is retained for migration context only.
            └─► Continue to next subreddit
 ```
 
-### Browser Session Recovery
+### Account Session Recovery
 
 ```
-1. BrowserClient.verifySession() returns false
+1. Reddit or Matrix authentication is rejected
    │
-   ├─► Check for expired cookies
-   │
-   ├─► Attempt automated re-login
-   │   ├─► BrowserClient.login()
-   │   └─► If success: continue
-   │
-   └─► If re-login fails:
-       ├─► Log error: "Browser session expired"
-       ├─► Stop bot
-       └─► Require manual login (scripts/login.ts)
+   ├─► Invalidate the shared account-auth gate
+   ├─► Stop account-bound schedulers
+   └─► Wait for a fresh combined dump from the Chrome extension
 ```
 
 ---

docs/deployment.md

@@ -74,8 +74,8 @@ rateLimit:
   jitterMs: 15000
 
 browser:
-  headless: true
-  userDataDir: "./data/browser"
+  sessionDir: "./data/browser-session"
+  dryRun: true
 
 database:
   path: "./data/reddit-bot.db"
@@ -89,23 +89,13 @@ dryRun: true  # Start in dry run mode
 Set environment variables:
 
 ```bash
-export REDDIT_USERNAME="your-username"
-export REDDIT_PASSWORD="your-password"
+export OPENROUTER_API_KEY="sk-or-v1-your-key"
+export WEB_DASHBOARD_TOKEN="long-random-secret"
 ```
 
-### 3. Initial Login
+### 3. Import account session
 
-Run the login script to establish a browser session:
-
-```bash
-npm run login
-```
-
-This will:
-1. Open a browser window
-2. Navigate to Reddit login
-3. Wait for you to complete login (including 2FA if enabled)
-4. Save cookies to `data/browser/`
+Start the dashboard, then upload a combined Reddit and Matrix dump created by the local Chrome extension. Until both identities verify, account work remains paused.
 
 ### 4. Start the Bot
 
@@ -144,23 +134,19 @@ docker run -d \
   -p 3000:3000 \
   -v $(pwd)/data:/app/data \
   -e OPENROUTER_API_KEY=sk-or-v1-your-key \
-  -e REDDIT_USERNAME=your-username \
-  -e REDDIT_PASSWORD=your-password \
-  -e BROWSER_HEADLESS=true \
+  -e WEB_DASHBOARD_TOKEN=long-random-secret \
   reddit-bot:latest
 ```
 
 ### Dockerfile behavior
 
-The image is based on the Playwright Jammy image rather than Alpine because the
-runtime needs Chromium and its system libraries. It installs Xvfb, x11vnc,
-noVNC, Fluxbox, and Websockify for interactive Reddit login; installs the locked
-Node dependencies; copies the repository; and runs `npm run build`.
+The image is based on the Playwright Jammy image because the remaining
+authenticated browser operations need Chromium and its system libraries. It
+does not install a display server, VNC, or consumer Google Chrome.
 
 That build produces both `dist/` for the Express server and
-`apps/dashboard/dist/` for Vite assets. Ports 3000 (dashboard/API) and 6080
-(noVNC) are exposed, and `docker/entrypoint.sh` starts the display services and
-application. This is a single-stage image and retains development dependencies
+`apps/dashboard/dist/` for Vite assets. Port 3000 serves the dashboard/API and
+the container starts the Node process directly. This is a single-stage image and retains development dependencies
 needed by the current build/runtime layout.
 
 ---
@@ -182,9 +168,7 @@ services:
       - ./data:/app/data
     environment:
       - OPENROUTER_API_KEY=${OPENROUTER_API_KEY}
-      - REDDIT_USERNAME=${REDDIT_USERNAME}
-      - REDDIT_PASSWORD=${REDDIT_PASSWORD}
-      - BROWSER_HEADLESS=true
+      - WEB_DASHBOARD_TOKEN=${WEB_DASHBOARD_TOKEN}
     restart: unless-stopped
     healthcheck:
       test: ["CMD", "wget", "--spider", "http://localhost:3000/api/stats"]
@@ -225,9 +209,7 @@ Dokploy is a self-hosted platform for deploying applications. See `DOKPLOY_DEPLO
 1. **Create Application**: In Dokploy dashboard, create a new Docker application
 2. **Set Environment Variables**:
    - `OPENROUTER_API_KEY`
-   - `REDDIT_USERNAME`
-   - `REDDIT_PASSWORD`
-   - `BROWSER_HEADLESS`
+   - `WEB_DASHBOARD_TOKEN`
 3. **Mount Volume**: Mount `./data` for persistent storage
 4. **Set Port**: Map container port 3000 to host port
 5. **Deploy**: Push to repository and trigger deployment
@@ -244,9 +226,7 @@ app:
   
   environment:
     OPENROUTER_API_KEY: $OPENROUTER_API_KEY
-    REDDIT_USERNAME: $REDDIT_USERNAME
-    REDDIT_PASSWORD: $REDDIT_PASSWORD
-    BROWSER_HEADLESS: "true"
+    WEB_DASHBOARD_TOKEN: $WEB_DASHBOARD_TOKEN
   
   ports:
     - container: 3000
@@ -276,7 +256,7 @@ app:
 
 ### Performance
 
-1. **Browser Headless**: Always use headless mode in production
+1. **Account dumps**: Delete downloaded dumps after the dashboard verifies them
 2. **WAL Mode**: SQLite WAL mode is enabled by default for concurrent reads
 3. **Rate Limiting**: Adjust based on Reddit account age and trust level
 4. **Message Volume**: Start low (10-20/hour) and increase gradually
@@ -359,15 +339,15 @@ docker compose start
 3. Verify environment variables are set
 4. Check for Zod validation errors in logs
 
-### Browser Login Fails
+### Account Import Fails
 
-**Symptom**: "Browser session expired" or login fails.
+**Symptom**: Account work stays paused or import verification fails.
 
 **Steps**:
-1. Delete browser data: `rm -rf data/browser/`
-2. Re-run login: `npm run login`
-3. Check Reddit account is not locked
-4. Try `BROWSER_HEADLESS=false` for debugging
+1. Sign in to Reddit in local Chrome
+2. Open Reddit Chat and wait for the extension badge to show `OK`
+3. Export and upload a new combined session dump
+4. Check logs for Reddit or Matrix identity errors
 
 ### AI Analysis Fails
 

docs/development.md

@@ -45,8 +45,7 @@ RedditBot/
     ├── ai/
     │   └── openrouter.ts    # OpenRouter AI client
     ├── browser/
-    │   ├── client.ts        # Playwright browser manager
-    │   ├── message-page.ts  # DM compose automation
+    │   ├── client.ts        # Managed Playwright context
     │   └── media-downloader.ts # Media download
     ├── services/
     │   ├── monitor.ts           # Post discovery
@@ -87,17 +86,13 @@ cp config.yaml config.yaml.backup  # Backup existing
 ### 3. Set Environment Variables
 
 ```bash
-export REDDIT_USERNAME="your-username"
-export REDDIT_PASSWORD="your-password"
 export OPENROUTER_API_KEY="sk-or-v1-your-key"
+export WEB_DASHBOARD_TOKEN="long-random-secret"
 ```
 
-### 4. Initial Login
+### 4. Account authentication
 
-```bash
-# Open browser for manual login
-npm run login
-```
+Start the app, then import a combined Reddit and Matrix session dump from the local Chrome extension under **Settings > Access**.
 
 ### 5. Start Development Server
 
@@ -357,21 +352,9 @@ curl http://localhost:3000/api/analytics/by-strategy
 
 ## Debugging
 
-### Browser Debugging
+### Account debugging
 
-Run with visible browser:
-
-```yaml
-# config.yaml
-browser:
-  headless: false
-```
-
-Or set environment variable:
-
-```bash
-BROWSER_HEADLESS=false npm run dev
-```
+Use dashboard session status and structured logs. The backend does not expose or launch an interactive login browser.
 
 ### DOM Inspection
 

docs/services.md

@@ -690,7 +690,7 @@ Generate a similar message for this image..."
 
 ### Purpose
 
-Manages the Playwright browser session with persistent cookies/storage. Handles automated login, session verification, and 2FA/captcha detection.
+Manages the headless Playwright context used after an extension dump is imported. It accepts Reddit cookies, verifies account identity, and supplies authenticated context to the remaining browser-backed operations. It never performs login.
 
 ### Public Methods
 
@@ -704,8 +704,8 @@ class BrowserClient {
   /** Verify browser session is active */
   verifySession(): Promise<boolean>
 
-  /** Perform automated login */
-  login(): Promise<void>
+  /** Import Reddit cookies from a validated extension dump */
+  importRedditCookies(cookies: Cookie[]): Promise<void>
 
   /** Get page context for operations */
   getPage(): Promise<Page>
@@ -715,93 +715,20 @@ class BrowserClient {
 }
 ```
 
-### Login Flow
+### Import Flow
 
-```
-1. Navigate to Reddit login page
-2. Fill username and password
-3. Submit form
-4. Check for 2FA prompt
-   └─► If present: wait for manual input (with timeout)
-5. Check for captcha
-   └─► If present: log warning, wait
-6. Verify login success:
-   └─► Check for user menu indicator
-   └─► Check for profile avatar
-   └─► Fallback: API request to /api/me
-7. Save cookies to persistent directory
-8. On failure: capture debug screenshot
-```
+The dashboard validates a combined extension dump, verifies Matrix with `whoami`, imports Reddit cookies, verifies Reddit identity, and only then marks the shared account gate authenticated.
 
 ### Session Persistence
 
 - Cookies and storage are saved to `config.browser.userDataDir`
 - Subsequent launches restore the session automatically
-- Session expires when Reddit cookies expire (requires re-login)
+- Session expiry pauses account work until a fresh extension dump is imported
 
 ### Dependencies
 
-- `Config` - Credentials, headless mode, user data dir
-- `Logger` - Login progress, errors
-
----
-
-## MessagePage
-
-**File**: `src/browser/message-page.ts`  
-**Lines**: 560  
-**Responsibility**: Reddit DM compose page automation
-
-### Purpose
-
-Automates the Reddit DM compose page: filling recipient/subject/body fields, handling shadow DOM components, submitting messages, and verifying success.
-
-### Public Methods
-
-```typescript
-class MessagePage {
-  constructor(
-    private browser: BrowserClient,
-    private config: Config,
-    private logger: Logger
-  )
-
-  /** Send a DM to a recipient */
-  sendDM(recipient: string, subject: string, body: string): Promise<boolean>
-
-  /** Check if recipient field shows an error */
-  hasRecipientError(page: Page): Promise<boolean>
-}
-```
-
-### Shadow DOM Handling
-
-Reddit's compose form uses `faceplate-*` web components:
-
-```javascript
-// Fill shadow DOM input fields
-page.evaluate(({ selector, value }) => {
-  const shadowInput = document.querySelector(`${selector} input`);
-  if (shadowInput) {
-    shadowInput.value = value;
-    shadowInput.dispatchEvent(new Event('input', { bubbles: true }));
-  }
-}, { selector: 'faceplate-textarea[name="body"]', value: body });
-```
-
-### Dry Run Mode
-
-When `config.dryRun` is enabled:
-- All fields are filled as normal
-- Submit button is NOT clicked
-- Message is logged but not sent
-- Returns `true` (simulates success)
-
-### Dependencies
-
-- `BrowserClient` - Playwright page access
-- `Config` - Dry run mode
-- `Logger` - Send activity
+- `Config` - Persistent session directory
+- `Logger` - Import verification progress and errors
 
 ---
 

packages/api-contracts/src/activity.ts

@@ -15,6 +15,8 @@ export const ActivityItemSchema = z.strictObject({
   message: z.string(),
   recipient: z.string().optional(),
   imageUrl: z.string().optional(),
+  postTitle: z.string().optional(),
+  postUrl: z.string().optional(),
 });
 
 export const ActivityResponseSchema = z.array(ActivityItemSchema);

packages/api-contracts/src/chats.ts

@@ -24,6 +24,7 @@ export const ActiveChatSchema = z.strictObject({
   roomId: z.string().optional(),
   messages: z.array(ChatMessageSchema).optional(),
   originMessage: z.string().optional(),
+  hasReceivedImages: z.boolean().optional(),
 });
 export const ChatsResponseSchema = z.array(ActiveChatSchema);
 export const ConversationsResponseSchema = ChatsResponseSchema;
@@ -62,6 +63,7 @@ export const ConversationDetailResponseSchema = ActiveChatSchema.extend({
     subreddit: z.string().optional(),
     title: z.string().optional(),
     url: z.string(),
+    imageUrl: z.string().nullable().optional(),
     sentAt: z.number(),
   }).nullable(),
   syncInProgress: z.strictObject({

packages/api-contracts/src/config.ts

@@ -35,17 +35,20 @@ export const SubredditConfigSchema = z.strictObject({
 export const ConfigResponseSchema = RuntimeConfigSchema.extend({
   subreddits: z.array(SubredditConfigSchema),
   tones: z.array(ToneKeySchema),
+  advanced: z.record(z.string(), z.unknown()).optional(),
 });
 export const ConfigUpdateRequestSchema = z.strictObject({
   rateLimit: RateLimitConfigSchema.partial().optional(),
   browser: z.strictObject({ dryRun: z.boolean().optional() }).optional(),
   reddit: RuntimeRedditConfigSchema.partial().optional(),
   subreddits: z.array(SubredditConfigSchema).min(1).optional(),
+  advanced: z.record(z.string(), z.unknown()).optional(),
 });
 export const ConfigUpdateResponseSchema = z.strictObject({
   success: z.literal(true),
   config: RuntimeConfigSchema,
   subreddits: z.array(SubredditConfigSchema),
+  advanced: z.record(z.string(), z.unknown()).optional(),
 });
 
 export type RuntimeConfig = z.infer<typeof RuntimeConfigSchema>;

packages/api-contracts/src/messages.ts

@@ -13,6 +13,7 @@ export const SentMessageSchema = z.strictObject({
   chatRoomId: z.string().nullable(),
   subreddit: z.string().optional(),
   postTitle: z.string().optional(),
+  postUrl: z.string().optional(),
   postImageUrl: z.string().optional(),
   postImageAnalysis: z.string().optional(),
 });
@@ -23,6 +24,7 @@ export const ProcessedPostSchema = z.strictObject({
   subreddit: z.string(),
   author: z.string(),
   title: z.string(),
+  postUrl: z.string().nullable().optional(),
   imageUrl: z.string().nullable(),
   imageAnalysis: z.string().nullable(),
   generatedMessage: z.string().nullable(),

packages/api-contracts/tests/contracts.test.ts

@@ -106,6 +106,7 @@ describe('dashboard endpoint contracts', () => {
     const processedPost = {
       id: 'post-1', subreddit: 'example', author: 'alice', title: 'Example',
       imageUrl: null, imageAnalysis: null, generatedMessage: 'Hello',
+      postUrl: 'https://www.reddit.com/r/example/comments/post-1/',
       processedAt: 1_700_000_000_000, messageSent: true, error: null,
     };
     expect(ProcessedPostsResponseSchema.safeParse([processedPost]).success).toBe(true);
@@ -136,7 +137,7 @@ describe('dashboard endpoint contracts', () => {
     expect(ConfigResponseSchema.parse(payload)).toEqual(payload);
     expect(ConfigResponseSchema.safeParse({ ...payload, tones: [1] }).success).toBe(false);
     expect(ConfigUpdateRequestSchema.safeParse({
-      rateLimit: { maxMessagesPerHour: 10 }, browser: { dryRun: true },
+      rateLimit: { maxMessagesPerHour: 10 }, browser: { dryRun: true }, advanced: { media: { syncEnabled: false } },
     }).success).toBe(true);
     expect(ConfigUpdateRequestSchema.safeParse({ browser: { dryRun: 'yes' } }).success).toBe(false);
   });
@@ -160,7 +161,7 @@ describe('dashboard endpoint contracts', () => {
       ...chat,
       triggeringPost: {
         id: 'post-1', subreddit: 'example', title: 'Example',
-        url: 'https://www.reddit.com/r/example/comments/post-1/', sentAt: 1_700_000_000_000,
+        url: 'https://www.reddit.com/r/example/comments/post-1/', imageUrl: 'https://i.redd.it/example.jpg', sentAt: 1_700_000_000_000,
       },
       syncInProgress: null,
     }).success).toBe(true);

src/bootstrap.ts

@@ -24,6 +24,7 @@ import {
   ChatService,
   MatrixClient,
   MatrixMediaDownloader,
+  MatrixUsernameResolver,
   MatrixTokenRefresher,
   loadCachedCredentials,
   saveCredentials,
@@ -33,11 +34,11 @@ import {
 import { MediaService } from './services/media.js';
 import { MediaSyncService } from './services/media-sync.js';
 import { RateLimiter } from './utils/rate-limiter.js';
-import { fetchWithTimeout } from './utils/fetch-with-timeout.js';
 import { WebServer } from './web/server.js';
 import { reportReply } from './web/event-reporting.js';
 import { RedditSessionImporter } from './services/reddit-session-importer.js';
 import { AccountAuthContext } from './services/account-auth-context.js';
+import { ConfigStore } from './config/persistence.js';
 
 export interface AppContainer {
   config: Config;
@@ -81,7 +82,11 @@ export interface AppContainer {
  * Returns a populated container. Caller owns lifecycle (start loop, handle
  * shutdown).
  */
-export async function bootstrap(config: Config, logger: Logger): Promise<AppContainer> {
+export async function bootstrap(
+  config: Config,
+  logger: Logger,
+  existingDatabase?: Database.Database,
+): Promise<AppContainer> {
   // Wire winston → dashboard log buffer immediately so the matrix-token
   // sniff and other early bootstrap diagnostics are visible in /api/logs.
   const broadcaster = new LogBroadcaster();
@@ -90,7 +95,7 @@ export async function bootstrap(config: Config, logger: Logger): Promise<AppCont
   }
 
   // Database
-  const db = createDatabase(config);
+  const db = existingDatabase ?? createDatabase(config);
   runMigrations(db);
   const postsRepo = new PostsRepository(db);
   const messagesRepo = new MessagesRepository(db);
@@ -186,35 +191,12 @@ export async function bootstrap(config: Config, logger: Logger): Promise<AppCont
   // or token-sniff flow.
   const tokenRefresher = new MatrixTokenRefresher();
 
-  // 4. Username resolver — turns t2 IDs into real Reddit usernames so the
-  //    dashboard isn't full of `t2_abc123`. Uses Reddit's bulk endpoint.
+  // 4. Username resolver — Matrix profiles expose Reddit display names using
+  //    the same authenticated session that powers chat sync.
+  const matrixUsernameResolver = new MatrixUsernameResolver(activeMatrixClient);
   const usernameResolver: UsernameResolver = {
-    async resolveT2Ids(ids) {
-      if (ids.length === 0) return {};
-      const out: Record<string, string> = {};
-      for (let i = 0; i < ids.length; i += 100) {
-        const chunk = ids.slice(i, i + 100).join(',');
-        try {
-          const res = await fetchWithTimeout(
-            // www.reddit.com serves this unauthenticated; the api.reddit.com
-            // host 404s the same path without an OAuth token.
-            `https://www.reddit.com/api/user_data_by_account_ids.json?ids=${encodeURIComponent(chunk)}`,
-            { headers: { 'User-Agent': config.reddit.userAgent }, timeoutMs: 15_000 },
-          );
-          if (!res.ok) {
-            logger.debug(`user_data_by_account_ids → ${res.status}`);
-            continue;
-          }
-          const json = (await res.json()) as Record<string, { name?: string }>;
-          for (const [t2, info] of Object.entries(json)) {
-            if (info?.name) out[t2] = info.name;
-          }
-        } catch (err) {
-          logger.debug('user_data_by_account_ids failed:', err);
-        }
-      }
-      return out;
-    },
+    resolveT2Ids: (ids) => matrixUsernameResolver.resolveT2Ids(ids),
+    resolveUsernameToT2: (username) => redditApi.resolveUsernameToT2(username),
   };
 
   const chatService = new ChatService(
@@ -244,6 +226,8 @@ export async function bootstrap(config: Config, logger: Logger): Promise<AppCont
       setMatrixClient(client) {
         activeMatrixClient = client;
         chatService.setMatrixClient(client);
+        mediaDownloader.setMatrixClient(client);
+        matrixUsernameResolver.setMatrixClient(client);
       },
     },
     (credentials) => new MatrixClient(credentials, logger),
@@ -268,7 +252,7 @@ export async function bootstrap(config: Config, logger: Logger): Promise<AppCont
     // Stream sync-progress frames over the dashboard's SSE channel so the
     // full-sync UI can show live phase + per-room progress.
     let lastSyncProgress: { kind: 'full' | 'delta'; current: number; startedAt: number } | null = null;
-    chatService.setProgressListener((progress) => {
+    chatService.setProgressListener((progress, completion) => {
       webServer!.broadcastSyncProgress(progress as Record<string, unknown> | null);
       if (progress) {
         const syncId = `chat-${progress.startedAt}`;
@@ -286,12 +270,22 @@ export async function bootstrap(config: Config, logger: Logger): Promise<AppCont
         }
         lastSyncProgress = progress;
       } else if (lastSyncProgress) {
-        broadcaster.dashboardEvents.sync({
-          phase: 'completed',
-          id: `chat-${lastSyncProgress.startedAt}`,
-          kind: lastSyncProgress.kind,
-          processed: lastSyncProgress.current,
-        });
+        const id = `chat-${lastSyncProgress.startedAt}`;
+        if (completion?.status === 'failed') {
+          broadcaster.dashboardEvents.sync({
+            phase: 'failed',
+            id,
+            kind: lastSyncProgress.kind,
+            error: completion.error,
+          });
+        } else {
+          broadcaster.dashboardEvents.sync({
+            phase: 'completed',
+            id,
+            kind: lastSyncProgress.kind,
+            processed: lastSyncProgress.current,
+          });
+        }
         lastSyncProgress = null;
       }
     });
@@ -319,6 +313,7 @@ export async function bootstrap(config: Config, logger: Logger): Promise<AppCont
     webServer.setSessionImporter(sessionImporter);
     webServer.setAccountAuth(accountAuth);
     webServer.setConversationStateRepository(conversationStateRepo);
+    webServer.setConfigStore(new ConfigStore(db));
     webServer.setOnConfigChange(() => logger.info('Runtime config updated via dashboard'));
   }
 

src/browser/client.ts

@@ -175,8 +175,12 @@ export class BrowserClient {
           const res = await fetch('https://www.reddit.com/api/me.json', { credentials: 'include' });
           if (!res.ok) return null;
           const data: unknown = await res.json();
-          if (!data || typeof data !== 'object' || !('name' in data) || typeof data.name !== 'string') return null;
-          const username = data.name.trim();
+          if (!data || typeof data !== 'object') return null;
+          const account = 'data' in data && data.data && typeof data.data === 'object'
+            ? data.data
+            : data;
+          if (!('name' in account) || typeof account.name !== 'string') return null;
+          const username = account.name.trim();
           return username || null;
         } catch {
           return null;

src/config/index.ts

@@ -157,7 +157,20 @@ export const ConfigSchema = z.object({
 
 export type Config = z.infer<typeof ConfigSchema>;
 
-export function loadConfig(): Config {
+export interface ConfigPersistence {
+  load(environment?: NodeJS.ProcessEnv): Config | null;
+  save(config: Config): void;
+}
+
+/**
+ * Loads the database-backed configuration. A legacy YAML file is imported
+ * exactly once when the database has not yet been seeded, which makes the
+ * migration safe for existing installations.
+ */
+export function loadConfig(store?: ConfigPersistence): Config {
+  const storedConfig = store?.load(process.env);
+  if (storedConfig) return storedConfig;
+
   const configPath = path.resolve(process.cwd(), 'config.yaml');
 
   if (!fs.existsSync(configPath)) {
@@ -173,6 +186,11 @@ export function loadConfig(): Config {
   }
   rawConfig.openrouter.apiKey = process.env.OPENROUTER_API_KEY || rawConfig.openrouter.apiKey;
 
+  if (!rawConfig.database) rawConfig.database = {};
+  // The database must be located before application settings can be read, so
+  // its path is an environment-owned bootstrap value rather than app config.
+  rawConfig.database.path = process.env.DATABASE_PATH ?? './data/reddit-bot.db';
+
   if (process.env.WEB_DASHBOARD_TOKEN !== undefined) {
     if (!rawConfig.web) rawConfig.web = {};
     rawConfig.web.authToken = process.env.WEB_DASHBOARD_TOKEN;
@@ -195,5 +213,6 @@ export function loadConfig(): Config {
     throw new Error('WEB_DASHBOARD_TOKEN environment variable or web.authToken configuration is required when the dashboard is enabled');
   }
 
+  store?.save(result.data);
   return result.data;
 }

src/config/persistence.ts

@@ -1,74 +1,83 @@
-import fs from 'fs';
-import path from 'path';
-import YAML from 'yaml';
-import type { SubredditConfig } from './index.js';
+import type Database from 'better-sqlite3';
+import { ConfigSchema, type Config } from './index.js';
+
+type StoredConfig = Omit<Config, 'database' | 'openrouter' | 'web'> & {
+  openrouter: Omit<Config['openrouter'], 'apiKey'>;
+  web: Omit<Config['web'], 'authToken'>;
+};
 
 /**
- * Writes an updated subreddit list back to `config.yaml`, preserving the
- * surrounding YAML structure, comment blocks, and per-row inline comments
- * for entries that survive the update.
- *
- * Strategy:
- *   - Parse with `YAML.parseDocument` so the CST (including comments) is
- *     intact.
- *   - For each updated entry that matches an existing row by name, mutate
- *     the existing node's fields in place — its `.comment` (the trailing
- *     `# ...` annotation on the line) is preserved.
- *   - New entries become fresh flow-style maps appended in the caller's
- *     order; entries no longer in the list are dropped (and their comments
- *     go with them, since the comment is attached to the row).
- *   - Atomic write via tmp file + rename so a crash mid-write can't leave
- *     a half-written config on disk.
+ * Persists application-owned configuration in SQLite. Secrets and the
+ * database location remain environment-owned bootstrap settings and are
+ * deliberately never written to the settings record.
  */
-export function persistSubreddits(
-  subreddits: SubredditConfig[],
-  configPath: string = path.resolve(process.cwd(), 'config.yaml'),
-): void {
-  const raw = fs.readFileSync(configPath, 'utf-8');
-  const doc = YAML.parseDocument(raw);
+export class ConfigStore {
+  constructor(private readonly db: Database.Database) {}
 
-  const seq = doc.getIn(['reddit', 'subreddits']) as YAML.YAMLSeq | undefined;
-  if (!seq || !YAML.isSeq(seq)) {
-    throw new Error('reddit.subreddits is not a sequence in config.yaml');
-  }
+  load(environment: NodeJS.ProcessEnv = process.env): Config | null {
+    const row = this.db.prepare('SELECT config_json FROM app_config WHERE id = 1').get() as
+      | { config_json: string }
+      | undefined;
+    if (!row) return null;
 
-  // Map existing items by their `name` so we can reuse YAMLMap nodes
-  // (and the trailing comments attached to them).
-  const existingByName = new Map<string, YAML.YAMLMap>();
-  for (const item of seq.items) {
-    if (!YAML.isMap(item)) continue;
-    const name = item.get('name');
-    if (typeof name === 'string') existingByName.set(name, item);
-  }
-
-  const nextItems: YAML.YAMLMap[] = [];
-  for (const sub of subreddits) {
-    const existing = existingByName.get(sub.name);
-    const node = existing ?? new YAML.YAMLMap();
-    if (!existing) {
-      // Match the on-disk style: flow-mapped, single-quoted strings.
-      node.flow = true;
-      node.set('name', sub.name);
+    let stored: unknown;
+    try {
+      stored = JSON.parse(row.config_json);
+    } catch (error) {
+      throw new Error(`Stored application configuration is not valid JSON: ${String(error)}`);
     }
-    setOrDelete(node, 'type', sub.type === 'image' ? undefined : sub.type);
-    setOrDelete(node, 'weight', sub.weight);
-    setOrDelete(node, 'tone', sub.tone === 'default' ? undefined : sub.tone);
-    setOrDelete(node, 'scripted', sub.scripted);
-    nextItems.push(node);
+
+    return validateConfig(withBootstrapSettings(stored, environment));
   }
 
-  seq.items = nextItems;
-
-  const out = doc.toString();
-  const tmp = configPath + '.tmp';
-  fs.writeFileSync(tmp, out, 'utf-8');
-  fs.renameSync(tmp, configPath);
-}
-
-function setOrDelete(node: YAML.YAMLMap, key: string, value: unknown): void {
-  if (value === undefined || value === null || value === '') {
-    if (node.has(key)) node.delete(key);
-    return;
+  save(config: Config): void {
+    const stored = toStoredConfig(config);
+    this.db.prepare(`
+      INSERT INTO app_config (id, config_json, updated_at)
+      VALUES (1, ?, ?)
+      ON CONFLICT(id) DO UPDATE SET
+        config_json = excluded.config_json,
+        updated_at = excluded.updated_at
+    `).run(JSON.stringify(stored), Date.now());
   }
-  node.set(key, value);
+}
+
+function toStoredConfig(config: Config): StoredConfig {
+  const { database: _database, ...applicationConfig } = config;
+  const { apiKey: _apiKey, ...openrouter } = applicationConfig.openrouter;
+  const { authToken: _authToken, ...web } = applicationConfig.web;
+  return { ...applicationConfig, openrouter, web };
+}
+
+function withBootstrapSettings(stored: unknown, environment: NodeJS.ProcessEnv): unknown {
+  if (!stored || typeof stored !== 'object' || Array.isArray(stored)) return stored;
+  const record = stored as Record<string, unknown>;
+  const openrouter = objectValue(record.openrouter);
+  const web = objectValue(record.web);
+  return {
+    ...record,
+    database: { path: environment.DATABASE_PATH ?? './data/reddit-bot.db' },
+    openrouter: { ...openrouter, apiKey: environment.OPENROUTER_API_KEY },
+    web: { ...web, authToken: environment.WEB_DASHBOARD_TOKEN },
+  };
+}
+
+function objectValue(value: unknown): Record<string, unknown> {
+  return value && typeof value === 'object' && !Array.isArray(value)
+    ? value as Record<string, unknown>
+    : {};
+}
+
+function validateConfig(raw: unknown): Config {
+  const result = ConfigSchema.safeParse(raw);
+  if (!result.success) {
+    const errors = result.error.issues
+      .map((issue) => `  - ${String(issue.path.join('.'))}: ${issue.message}`)
+      .join('\n');
+    throw new Error(`Invalid stored configuration:\n${errors}`);
+  }
+  if (result.data.web.enabled && !result.data.web.authToken) {
+    throw new Error('WEB_DASHBOARD_TOKEN environment variable is required when the dashboard is enabled');
+  }
+  return result.data;
 }

src/database/client.ts

@@ -3,7 +3,7 @@ import type { Config } from '../config/index.js';
 import path from 'path';
 import fs from 'fs';
 
-export function createDatabase(config: Config): Database.Database {
+export function createDatabase(config: Pick<Config, 'database'>): Database.Database {
   const dbPath = config.database.path === ':memory:'
     ? ':memory:'
     : path.resolve(process.cwd(), config.database.path);
@@ -142,6 +142,56 @@ export function runMigrations(db: Database.Database): void {
         FOREIGN KEY (sent_message_id) REFERENCES sent_messages(id)
       );
     `),
+    () => {
+      addColumnIfNotExists(db, 'processed_posts', 'post_url', 'TEXT');
+      addColumnIfNotExists(db, 'activity_log', 'post_title', 'TEXT');
+      addColumnIfNotExists(db, 'activity_log', 'post_url', 'TEXT');
+      db.exec(`
+        UPDATE processed_posts
+        SET post_url = 'https://www.reddit.com/r/' || subreddit || '/comments/' || id || '/'
+        WHERE post_url IS NULL;
+
+        UPDATE activity_log
+        SET
+          post_title = (
+            SELECT pp.title
+            FROM sent_messages sm
+            JOIN processed_posts pp ON pp.id = sm.post_id
+            WHERE sm.recipient = activity_log.recipient COLLATE NOCASE
+              AND sm.sent_at <= activity_log.timestamp
+            ORDER BY sm.sent_at DESC
+            LIMIT 1
+          ),
+          post_url = (
+            SELECT pp.post_url
+            FROM sent_messages sm
+            JOIN processed_posts pp ON pp.id = sm.post_id
+            WHERE sm.recipient = activity_log.recipient COLLATE NOCASE
+              AND sm.sent_at <= activity_log.timestamp
+            ORDER BY sm.sent_at DESC
+            LIMIT 1
+          ),
+          image_url = COALESCE(image_url, (
+            SELECT pp.image_url
+            FROM sent_messages sm
+            JOIN processed_posts pp ON pp.id = sm.post_id
+            WHERE sm.recipient = activity_log.recipient COLLATE NOCASE
+              AND sm.sent_at <= activity_log.timestamp
+            ORDER BY sm.sent_at DESC
+            LIMIT 1
+          ))
+        WHERE type = 'sent'
+          AND recipient IS NOT NULL
+          AND post_url IS NULL;
+      `);
+    },
+    () => db.exec(`
+      CREATE TABLE IF NOT EXISTS app_config (
+        id INTEGER PRIMARY KEY CHECK(id = 1),
+        config_json TEXT NOT NULL,
+        updated_at INTEGER NOT NULL
+      );
+    `),
   ];
 
   let currentVersion = db.pragma('user_version', { simple: true }) as number;

src/database/repositories.ts

@@ -11,6 +11,7 @@ export interface ProcessedPostRecord {
   subreddit: string;
   author: string;
   title: string;
+  postUrl: string | null;
   imageUrl: string | null;
   imageAnalysis: string | null;
   generatedMessage: string | null;
@@ -32,6 +33,7 @@ export interface SentMessageRecord {
   chatRoomId: string | null;
   subreddit?: string;
   postTitle?: string;
+  postUrl?: string;
   postImageUrl?: string;
   postImageAnalysis?: string;
 }
@@ -74,6 +76,8 @@ export interface ActivityLogRecord {
   message: string;
   recipient: string | null;
   imageUrl: string | null;
+  postTitle: string | null;
+  postUrl: string | null;
 }
 
 export type DeliveryStatus = 'discovered' | 'prepared' | 'sending' | 'sent' | 'failed';
@@ -233,12 +237,12 @@ export class ActivityLogRepository {
 
   constructor(private db: Database.Database) {
     this.insertStmt = db.prepare(`
-      INSERT INTO activity_log (timestamp, type, message, recipient, image_url)
-      VALUES (?, ?, ?, ?, ?)
+      INSERT INTO activity_log (timestamp, type, message, recipient, image_url, post_title, post_url)
+      VALUES (?, ?, ?, ?, ?, ?, ?)
     `);
 
     this.getRecentStmt = db.prepare(`
-      SELECT timestamp, type, message, recipient, image_url
+      SELECT timestamp, type, message, recipient, image_url, post_title, post_url
       FROM activity_log
       ORDER BY id DESC
       LIMIT ?
@@ -260,6 +264,8 @@ export class ActivityLogRepository {
     message: string;
     recipient?: string;
     imageUrl?: string;
+    postTitle?: string;
+    postUrl?: string;
   }): void {
     this.insertStmt.run(
       item.timestamp,
@@ -267,6 +273,8 @@ export class ActivityLogRepository {
       item.message,
       item.recipient ?? null,
       item.imageUrl ?? null,
+      item.postTitle ?? null,
+      item.postUrl ?? null,
     );
   }
 
@@ -278,6 +286,8 @@ export class ActivityLogRepository {
       message: row.message as string,
       recipient: (row.recipient as string) ?? null,
       imageUrl: (row.image_url as string) ?? null,
+      postTitle: (row.post_title as string) ?? null,
+      postUrl: (row.post_url as string) ?? null,
     }));
   }
 
@@ -302,8 +312,8 @@ export class PostsRepository {
 
   constructor(private db: Database.Database) {
     this.insertStmt = db.prepare(`
-      INSERT INTO processed_posts (id, subreddit, author, title, image_url, processed_at)
-      VALUES (?, ?, ?, ?, ?, ?)
+      INSERT INTO processed_posts (id, subreddit, author, title, post_url, image_url, processed_at)
+      VALUES (?, ?, ?, ?, ?, ?, ?)
     `);
 
     this.existsStmt = db.prepare(`SELECT 1 FROM processed_posts WHERE id = ?`);
@@ -334,6 +344,7 @@ export class PostsRepository {
     subreddit: string;
     author: string;
     title: string;
+    postUrl?: string | null;
     imageUrl: string | null;
     processedAt: number;
   }): void {
@@ -342,6 +353,7 @@ export class PostsRepository {
       post.subreddit,
       post.author,
       post.title,
+      post.postUrl ?? null,
       post.imageUrl,
       post.processedAt
     );
@@ -368,6 +380,7 @@ export class PostsRepository {
       subreddit: row.subreddit as string,
       author: row.author as string,
       title: row.title as string,
+      postUrl: (row.post_url as string | null) ?? null,
       imageUrl: row.image_url as string | null,
       imageAnalysis: row.image_analysis as string | null,
       generatedMessage: row.generated_message as string | null,
@@ -384,6 +397,7 @@ export class PostsRepository {
       subreddit: row.subreddit as string,
       author: row.author as string,
       title: row.title as string,
+      postUrl: (row.post_url as string | null) ?? null,
       imageUrl: row.image_url as string | null,
       imageAnalysis: row.image_analysis as string | null,
       generatedMessage: row.generated_message as string | null,
@@ -408,8 +422,8 @@ export class MessagesRepository {
 
   constructor(private db: Database.Database) {
     this.insertStmt = db.prepare(`
-      INSERT INTO sent_messages (post_id, recipient, subject, message, sent_at, strategy_id)
-      VALUES (?, ?, ?, ?, ?, ?)
+      INSERT INTO sent_messages (post_id, recipient, subject, message, sent_at, strategy_id, chat_room_id)
+      VALUES (?, ?, ?, ?, ?, ?, ?)
     `);
 
     this.insertChatStmt = db.prepare(`
@@ -418,18 +432,19 @@ export class MessagesRepository {
     `);
 
     this.getByChatRoomIdStmt = db.prepare(`
-      SELECT sm.*, pp.subreddit, pp.title AS post_title, pp.image_url AS post_image_url,
+      SELECT sm.*, pp.subreddit, pp.title AS post_title, pp.post_url, pp.image_url AS post_image_url,
         pp.image_analysis AS post_image_analysis
       FROM sent_messages sm
       LEFT JOIN processed_posts pp ON sm.post_id = pp.id
       WHERE sm.chat_room_id = ?
+      ORDER BY sm.post_id IS NULL ASC, sm.sent_at DESC
       LIMIT 1
     `);
 
     this.getByPostIdStmt = db.prepare(`SELECT * FROM sent_messages WHERE post_id = ?`);
 
     this.getLatestByRecipientStmt = db.prepare(`
-      SELECT sm.*, pp.subreddit, pp.title AS post_title, pp.image_url AS post_image_url,
+      SELECT sm.*, pp.subreddit, pp.title AS post_title, pp.post_url, pp.image_url AS post_image_url,
         pp.image_analysis AS post_image_analysis
       FROM sent_messages sm
       LEFT JOIN processed_posts pp ON sm.post_id = pp.id
@@ -439,7 +454,7 @@ export class MessagesRepository {
     `);
 
     this.getRecentStmt = db.prepare(`
-      SELECT sm.*, pp.subreddit, pp.title AS post_title, pp.image_url AS post_image_url,
+      SELECT sm.*, pp.subreddit, pp.title AS post_title, pp.post_url, pp.image_url AS post_image_url,
         pp.image_analysis AS post_image_analysis
       FROM sent_messages sm
       LEFT JOIN processed_posts pp ON sm.post_id = pp.id
@@ -476,6 +491,7 @@ export class MessagesRepository {
     message: string;
     sentAt: number;
     strategyId?: string | null;
+    chatRoomId?: string | null;
   }): number {
     const result = this.insertStmt.run(
       message.postId,
@@ -483,7 +499,8 @@ export class MessagesRepository {
       message.subject,
       message.message,
       message.sentAt,
-      message.strategyId || null
+      message.strategyId || null,
+      message.chatRoomId ?? null,
     );
     return result.lastInsertRowid as number;
   }
@@ -608,6 +625,7 @@ export class MessagesRepository {
         SUM(CASE WHEN got_response = 1 THEN 1 ELSE 0 END) as total_responses
       FROM sent_messages
       WHERE sent_at > ?
+        AND (post_id IS NOT NULL OR strategy_id IS NOT NULL)
       GROUP BY day
       ORDER BY day ASC
     `).all(cutoff) as Record<string, unknown>[];
@@ -636,6 +654,7 @@ export class MessagesRepository {
       chatRoomId: (row.chat_room_id as string) ?? null,
       subreddit: (row.subreddit as string) || undefined,
       postTitle: (row.post_title as string) || undefined,
+      postUrl: (row.post_url as string) || undefined,
       postImageUrl: (row.post_image_url as string) || undefined,
       postImageAnalysis: (row.post_image_analysis as string) || undefined,
     };

src/index.ts

@@ -2,6 +2,8 @@ import { loadConfig } from './config/index.js';
 import { createLogger } from './utils/logger.js';
 import { bootstrap } from './bootstrap.js';
 import { runMainLoop } from './main-loop.js';
+import { createDatabase, runMigrations } from './database/client.js';
+import { ConfigStore } from './config/persistence.js';
 
 async function main(): Promise<void> {
   const logger = createLogger();
@@ -11,15 +13,19 @@ async function main(): Promise<void> {
   logger.info('='.repeat(60));
 
   let config;
+  const db = createDatabase({
+    database: { path: process.env.DATABASE_PATH ?? './data/reddit-bot.db' },
+  });
+  runMigrations(db);
   try {
-    config = loadConfig();
+    config = loadConfig(new ConfigStore(db));
     logger.info(`Loaded configuration for ${config.reddit.subreddits.length} subreddits`);
   } catch (error) {
     logger.error('Failed to load configuration:', error);
     process.exit(1);
   }
 
-  const app = await bootstrap(config, logger);
+  const app = await bootstrap(config, logger, db);
   await runMainLoop(app);
 }
 

src/main-loop.ts

@@ -242,11 +242,13 @@ export async function runMainLoop(app: AppContainer): Promise<void> {
           );
           const isChatSub = subredditEntry?.type === 'chat';
           const postImageUrl = isChatSub ? null : redditApi.getImageUrl(post);
+          const postUrl = redditApi.getPostUrl(post);
           postsRepo.insert({
             id: post.id,
             subreddit: post.subreddit,
             author: post.author,
             title: post.title,
+            postUrl,
             imageUrl: postImageUrl,
             processedAt: Date.now(),
           });
@@ -309,7 +311,11 @@ export async function runMainLoop(app: AppContainer): Promise<void> {
               logger.info(`Sending message to u/${post.author}...`);
               webServer?.pushLog('info', `Sending message to u/${post.author}...`);
 
-              const chat = await chatService.startConversation(post.author, processed.generatedMessage);
+              const chat = await chatService.startConversation(
+                post.author,
+                processed.generatedMessage,
+                post.author_fullname,
+              );
               const success = chat !== null;
 
               if (success) {
@@ -327,6 +333,7 @@ export async function runMainLoop(app: AppContainer): Promise<void> {
                   message: processed.generatedMessage,
                   sentAt: Date.now(),
                   strategyId: processed.strategyId,
+                  chatRoomId: chat.roomId,
                 });
 
                 const currentCount = currentHourlySendCount(rateLimiter);
@@ -338,6 +345,7 @@ export async function runMainLoop(app: AppContainer): Promise<void> {
                   `Sent message to u/${post.author} (r/${post.subreddit})`,
                   post.author,
                   postImageUrl ?? undefined,
+                  { postTitle: post.title, postUrl },
                 );
                 webServer?.pushLog('info', `✅ Message sent to u/${post.author} (${currentCount}/${config.rateLimit.maxMessagesPerHour} this hour)`);
                 webServer?.updateStats(currentCount);

src/reddit/api.ts

@@ -8,6 +8,7 @@ export interface RedditPost {
   name: string; // fullname like "t3_xxxxx"
   subreddit: string;
   author: string;
+  author_fullname?: string; // account fullname like "t2_xxxxx"
   title: string;
   url: string;
   permalink: string;
@@ -83,6 +84,26 @@ export class RedditApiClient {
     }
   }
 
+  /** Resolve a Reddit username through the authenticated browser session. */
+  async resolveUsernameToT2(username: string): Promise<string | null> {
+    const cookieHeader = await this.getCookieHeader();
+    const headers: Record<string, string> = {};
+    if (cookieHeader) headers.Cookie = cookieHeader;
+
+    try {
+      const response = await this.client.get(
+        `/user/${encodeURIComponent(username)}/about.json`,
+        { params: { raw_json: 1 }, headers },
+      );
+      const id = response.data?.data?.id;
+      if (typeof id !== 'string' || id.length === 0) return null;
+      return id.startsWith('t2_') ? id : `t2_${id}`;
+    } catch (error) {
+      if (axios.isAxiosError(error) && error.response?.status === 404) return null;
+      throw error;
+    }
+  }
+
   async getNewPosts(subreddit: string, limit = 25, type: 'image' | 'chat' = 'image'): Promise<RedditPost[]> {
     try {
       const cookieHeader = await this.getCookieHeader();

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;
 }
 
 /**

src/services/response-checker.ts

@@ -57,7 +57,17 @@ export class ResponseCheckerService {
         results.push(result);
 
         if (result.gotResponse) {
-          // Mark as got response
+          const hasPerformanceContext = Boolean(
+            message.postId || message.strategyId || message.subreddit,
+          );
+          if (!hasPerformanceContext) {
+            this.messagesRepo.markChecked(message.id);
+            this.logger.info(
+              `Response from u/${message.recipient} excluded from performance: no post, strategy, or subreddit context.`,
+            );
+            continue;
+          }
+
           this.messagesRepo.markGotResponse(message.id);
 
           // Get the original post info

src/web/activity-log.ts

@@ -20,12 +20,20 @@ export class ActivityLog {
         message: r.message,
         recipient: r.recipient ?? undefined,
         imageUrl: r.imageUrl ?? undefined,
+        postTitle: r.postTitle ?? undefined,
+        postUrl: r.postUrl ?? undefined,
       }))
       .reverse();
   }
 
-  push(type: ActivityItem['type'], message: string, recipient?: string, imageUrl?: string): void {
-    const item: ActivityItem = { timestamp: Date.now(), type, message, recipient, imageUrl };
+  push(
+    type: ActivityItem['type'],
+    message: string,
+    recipient?: string,
+    imageUrl?: string,
+    origin?: { postTitle: string; postUrl: string },
+  ): void {
+    const item: ActivityItem = { timestamp: Date.now(), type, message, recipient, imageUrl, ...origin };
     this.items.push(item);
     if (this.items.length > MAX_ITEMS) {
       this.items = this.items.slice(-MAX_ITEMS);

src/web/context.ts

@@ -19,6 +19,7 @@ import type { LogBroadcaster } from './log-broadcaster.js';
 import type { RuntimeConfig } from './types.js';
 import type { RedditSessionImporter } from '../services/reddit-session-importer.js';
 import type { AccountAuthContext } from '../services/account-auth-context.js';
+import type { ConfigStore } from '../config/persistence.js';
 
 /** Bag of everything the route modules might need. */
 export interface WebContext {
@@ -46,6 +47,7 @@ export interface WebContext {
     sessionImporter?: RedditSessionImporter;
     accountAuth?: AccountAuthContext;
     conversationState?: ConversationStateRepository;
+    configStore?: ConfigStore;
   };
 
   /** Bot pause/resume toggle read by the main loop. */

src/web/reddit-identities.ts

@@ -0,0 +1,39 @@
+import type { ActivityItem } from './types.js';
+
+const INTERNAL_REDDIT_ID = /@?t2_[a-z0-9]+(?::reddit\.com)?/gi;
+
+export interface RedditIdentityResolver {
+  resolveSenderDisplay(identity: string): string;
+}
+
+function isInternalIdentity(value: string): boolean {
+  return value === 'unknown' || value.startsWith('t2_') || /^@t2_[^:]+:/i.test(value);
+}
+
+export function resolveRedditUsername(
+  identity: string | null | undefined,
+  resolver?: RedditIdentityResolver,
+): string | null {
+  if (!identity) return null;
+  const candidate = resolver?.resolveSenderDisplay(identity) ?? identity;
+  if (isInternalIdentity(candidate)) return null;
+  return candidate.replace(/^\/?u\//i, '');
+}
+
+export function redactInternalRedditIds(message: string, username?: string | null): string {
+  return message
+    .replace(/u\/@?t2_[a-z0-9]+(?::reddit\.com)?/gi, username ? `u/${username}` : 'Reddit user')
+    .replace(INTERNAL_REDDIT_ID, username ?? 'Reddit user');
+}
+
+export function presentActivityItem(
+  item: ActivityItem,
+  resolver?: RedditIdentityResolver,
+): ActivityItem {
+  const recipient = resolveRedditUsername(item.recipient, resolver);
+  return {
+    ...item,
+    message: redactInternalRedditIds(item.message, recipient),
+    ...(recipient ? { recipient } : { recipient: undefined }),
+  };
+}

src/web/routes/config.ts

@@ -1,11 +1,36 @@
 import { Router } from 'express';
 import type { WebContext } from '../context.js';
-import { SubredditConfigSchema, type SubredditConfig } from '../../config/index.js';
+import { ConfigSchema, SubredditConfigSchema, type SubredditConfig } from '../../config/index.js';
 import { TONE_KEYS } from '../../config/tone-profiles.js';
-import { persistSubreddits } from '../../config/persistence.js';
 import { z } from 'zod';
 
 const SubredditsUpdateSchema = z.array(SubredditConfigSchema).min(1);
+const AdvancedConfigSchema = z.strictObject({
+  reddit: ConfigSchema.shape.reddit.omit({
+    subreddits: true,
+    prioritizeRecentPosts: true,
+    recentWindowMinutes: true,
+  }),
+  openrouter: ConfigSchema.shape.openrouter.omit({ apiKey: true }),
+  browser: z.strictObject({ sessionDir: z.string() }),
+  media: ConfigSchema.shape.media,
+  strategies: ConfigSchema.shape.strategies,
+  chatStrategies: ConfigSchema.shape.chatStrategies,
+});
+
+function advancedConfig(ctx: WebContext): z.infer<typeof AdvancedConfigSchema> {
+  const { subreddits: _subreddits, prioritizeRecentPosts: _prioritize, recentWindowMinutes: _window, ...reddit } = ctx.config.reddit;
+  const { apiKey: _apiKey, ...openrouter } = ctx.config.openrouter;
+  const { dryRun: _dryRun, ...browser } = ctx.config.browser;
+  return {
+    reddit,
+    openrouter,
+    browser,
+    media: ctx.config.media,
+    strategies: ctx.config.strategies,
+    chatStrategies: ctx.config.chatStrategies,
+  };
+}
 
 export function createConfigRouter(ctx: WebContext): Router {
   const router = Router();
@@ -17,12 +42,30 @@ export function createConfigRouter(ctx: WebContext): Router {
       reddit: ctx.runtimeConfig.reddit,
       subreddits: ctx.config.reddit.subreddits,
       tones: TONE_KEYS,
+      advanced: advancedConfig(ctx),
     });
   });
 
   router.put('/config', (req, res) => {
     try {
       const updates = req.body;
+      const configStore = ctx.services.configStore;
+      if (!configStore) throw new Error('Configuration persistence is unavailable');
+
+      const parsedSubreddits = updates.subreddits === undefined
+        ? null
+        : SubredditsUpdateSchema.safeParse(updates.subreddits);
+      if (parsedSubreddits && !parsedSubreddits.success) {
+        res.status(400).json({ error: 'Invalid subreddits payload', detail: parsedSubreddits.error.format() });
+        return;
+      }
+      const parsedAdvanced = updates.advanced === undefined
+        ? null
+        : AdvancedConfigSchema.safeParse(updates.advanced);
+      if (parsedAdvanced && !parsedAdvanced.success) {
+        res.status(400).json({ error: 'Invalid advanced configuration', detail: parsedAdvanced.error.format() });
+        return;
+      }
 
       if (updates.rateLimit) {
         if (typeof updates.rateLimit.minDelayBetweenMessagesMs === 'number') {
@@ -65,13 +108,8 @@ export function createConfigRouter(ctx: WebContext): Router {
       ctx.config.reddit.prioritizeRecentPosts = ctx.runtimeConfig.reddit.prioritizeRecentPosts;
       ctx.config.reddit.recentWindowMinutes = ctx.runtimeConfig.reddit.recentWindowMinutes;
 
-      if (updates.subreddits !== undefined) {
-        const parsed = SubredditsUpdateSchema.safeParse(updates.subreddits);
-        if (!parsed.success) {
-          res.status(400).json({ error: 'Invalid subreddits payload', detail: parsed.error.format() });
-          return;
-        }
-        const next: SubredditConfig[] = parsed.data;
+      if (parsedSubreddits?.success) {
+        const next: SubredditConfig[] = parsedSubreddits.data;
         const seen = new Set<string>();
         for (const s of next) {
           const key = s.name.toLowerCase();
@@ -81,10 +119,20 @@ export function createConfigRouter(ctx: WebContext): Router {
           }
           seen.add(key);
         }
-        persistSubreddits(next);
         ctx.config.reddit.subreddits = next;
       }
 
+      if (parsedAdvanced?.success) {
+        Object.assign(ctx.config.reddit, parsedAdvanced.data.reddit);
+        Object.assign(ctx.config.openrouter, parsedAdvanced.data.openrouter);
+        Object.assign(ctx.config.browser, parsedAdvanced.data.browser);
+        ctx.config.media = parsedAdvanced.data.media;
+        ctx.config.strategies = parsedAdvanced.data.strategies;
+        ctx.config.chatStrategies = parsedAdvanced.data.chatStrategies;
+      }
+
+      configStore.save(ctx.config);
+
       ctx.getOnConfigChange()?.(ctx.runtimeConfig);
 
       ctx.activity.push('info', 'Config updated via dashboard');
@@ -94,6 +142,7 @@ export function createConfigRouter(ctx: WebContext): Router {
         success: true,
         config: ctx.runtimeConfig,
         subreddits: ctx.config.reddit.subreddits,
+        advanced: advancedConfig(ctx),
       });
     } catch (error) {
       ctx.logger.error('Failed to update config:', error);

src/web/routes/conversations.ts

@@ -30,16 +30,45 @@ export function createConversationsRouter(ctx: WebContext): Router {
     return { messages, state, intent: chooseConversationIntent(messages, state, requestedIntent) };
   }
 
-  router.get('/conversations', async (_req, res) => {
+  router.get('/conversations', async (req, res) => {
     if (!ctx.services.chat) {
-      res.json([]);
+      res.status(503).json({ error: 'Chat service not initialized' });
       return;
     }
     try {
-      res.json(await ctx.services.chat.getCachedConversations());
+      const conversations = await ctx.services.chat.getCachedConversations();
+      if (req.query.includeImageMetadata !== 'true') {
+        res.json(conversations);
+        return;
+      }
+      const receivedMediaRooms = new Set<string>();
+      const receivedMediaUsers = new Set<string>();
+
+      if (ctx.services.media) {
+        try {
+          const mediaItems = await ctx.services.media.getMediaItems();
+          for (const item of mediaItems) {
+            if (item.sender.toLowerCase() === 'me') continue;
+            if (item.chatRoomId) receivedMediaRooms.add(item.chatRoomId);
+            if (item.chatUsername) receivedMediaUsers.add(item.chatUsername.toLowerCase());
+          }
+        } catch (error) {
+          ctx.logger.warn('Failed to read media index for conversation markers:', error);
+        }
+      }
+
+      res.json(conversations.map((conversation) => ({
+        ...conversation,
+        hasReceivedImages:
+          receivedMediaRooms.has(conversation.roomId ?? '')
+          || receivedMediaUsers.has(conversation.username.toLowerCase())
+          || (conversation.messages ?? []).some(
+            (message) => !message.isSelf && (message.media?.length ?? 0) > 0,
+          ),
+      })));
     } catch (error) {
       ctx.logger.error('Failed to fetch conversations:', error);
-      res.json([]);
+      res.status(500).json({ error: 'Failed to fetch conversations' });
     }
   });
 
@@ -49,21 +78,10 @@ export function createConversationsRouter(ctx: WebContext): Router {
       return;
     }
     try {
-      // If a sync is already in flight (e.g. a Full sync the user kicked off
-      // from the dashboard), don't queue *another* delta + lazy-load behind it
-      // — that's what makes the modal sit on "Loading…" for minutes. Render
-      // from cache and let the frontend show a "sync in progress" banner; the
-      // user can reopen once it's done.
+      // Conversation reads never initiate a sync. Sync lifecycle events can
+      // invalidate this query, so starting a sync here would create a loop.
       const syncStatus = ctx.services.chat.getSyncStatus();
       const syncInFlight = syncStatus.syncing;
-
-      if (!syncInFlight) {
-        try {
-          await ctx.services.chat.refreshTopChats();
-        } catch (err) {
-          ctx.logger.warn('Pre-open delta sync failed:', err);
-        }
-      }
       const conversation = await findConversation(decodeURIComponent(req.params.id));
       if (!conversation) {
         res.status(404).json({ error: 'Conversation not found' });
@@ -94,19 +112,24 @@ export function createConversationsRouter(ctx: WebContext): Router {
         subreddit?: string;
         title?: string;
         url: string;
+        imageUrl: string | null;
         sentAt: number;
       } | null = null;
       try {
-        const sent = ctx.repos.messages.getLatestByRecipient(conversation.username);
+        const sent = conversation.roomId
+          ? ctx.repos.messages.getByChatRoomId(conversation.roomId)
+            ?? ctx.repos.messages.getLatestByRecipient(conversation.username)
+          : ctx.repos.messages.getLatestByRecipient(conversation.username);
         if (sent && sent.postId) {
-          const url = sent.subreddit
+          const url = sent.postUrl ?? (sent.subreddit
             ? `https://www.reddit.com/r/${sent.subreddit}/comments/${sent.postId}/`
-            : `https://redd.it/${sent.postId}`;
+            : `https://redd.it/${sent.postId}`);
           triggeringPost = {
             id: sent.postId,
             subreddit: sent.subreddit,
             title: sent.postTitle,
             url,
+            imageUrl: sent.postImageUrl ?? null,
             sentAt: sent.sentAt,
           };
         }

src/web/routes/media.ts

@@ -1,5 +1,6 @@
 import { Router } from 'express';
 import type { WebContext } from '../context.js';
+import { resolveRedditUsername } from '../reddit-identities.js';
 
 export function createMediaRouter(ctx: WebContext): Router {
   const router = Router();
@@ -23,11 +24,17 @@ export function createMediaRouter(ctx: WebContext): Router {
 
       res.json(items.map((item) => {
         const live = item.chatRoomId ? byRoom.get(item.chatRoomId) : undefined;
-        const liveName = live?.username && live.username !== 'unknown' ? live.username : null;
-        const username = liveName ?? item.chatUsername ?? null;
+        const username = resolveRedditUsername(
+          live?.username ?? item.chatUsername,
+          ctx.services.chat,
+        );
+        const sender = /^(me|you)$/i.test(item.sender)
+          ? 'You'
+          : resolveRedditUsername(item.sender, ctx.services.chat) ?? username ?? 'Unknown Reddit user';
         return {
           ...item,
           chatUsername: username,
+          sender,
           urlPath: `/media/${encodeURIComponent(item.relativePath)}`,
         };
       }));

src/web/routes/stats.ts

@@ -1,10 +1,15 @@
 import { Router } from 'express';
 import type { WebContext } from '../context.js';
 import type { BotStats } from '../types.js';
+import { presentActivityItem } from '../reddit-identities.js';
 
 export function createStatsRouter(ctx: WebContext): Router {
   const router = Router();
 
+  const recentActivity = (limit: number) => ctx.activity
+    .recent(limit)
+    .map((item) => presentActivityItem(item, ctx.services.chat));
+
   router.get('/stats', (_req, res) => {
     const messages = ctx.repos.messages.getRecent(1000);
     const totalSent = messages.length;
@@ -23,7 +28,7 @@ export function createStatsRouter(ctx: WebContext): Router {
       maxMessagesPerHour: ctx.config.rateLimit.maxMessagesPerHour,
       subreddits: ctx.config.reddit.subreddits.map((s) => ({ name: s.name, type: s.type })),
       targetGenders: ctx.config.reddit.targetGenders,
-      recentActivity: ctx.activity.recent(10),
+      recentActivity: recentActivity(10),
       invitationCooldown: cooldown
         ? { until: cooldown.until, reason: cooldown.reason, redditCode: cooldown.redditCode }
         : null,
@@ -33,7 +38,7 @@ export function createStatsRouter(ctx: WebContext): Router {
   });
 
   router.get('/activity', (_req, res) => {
-    res.json(ctx.activity.recent(50));
+    res.json(recentActivity(50));
   });
 
   router.get('/posts/by-author/:username', (req, res) => {

src/web/server.ts

@@ -21,6 +21,7 @@ import type { StrategySelector } from '../services/strategy-selector.js';
 import type { BrowserClient } from '../browser/client.js';
 import type { RedditSessionImporter } from '../services/reddit-session-importer.js';
 import type { AccountAuthContext } from '../services/account-auth-context.js';
+import type { ConfigStore } from '../config/persistence.js';
 import { ActivityLog } from './activity-log.js';
 import { LogBroadcaster } from './log-broadcaster.js';
 import type { WebContext } from './context.js';
@@ -214,8 +215,18 @@ export class WebServer {
     this.services.conversationState = conversationState;
   }
 
-  logActivity(type: ActivityItem['type'], message: string, recipient?: string, imageUrl?: string): void {
-    this.activity.push(type, message, recipient, imageUrl);
+  setConfigStore(configStore: ConfigStore): void {
+    this.services.configStore = configStore;
+  }
+
+  logActivity(
+    type: ActivityItem['type'],
+    message: string,
+    recipient?: string,
+    imageUrl?: string,
+    origin?: { postTitle: string; postUrl: string },
+  ): void {
+    this.activity.push(type, message, recipient, imageUrl, origin);
   }
 
   pushLog(level: LogEntry['level'], message: string, data?: unknown): void {

src/web/types.ts

@@ -24,6 +24,8 @@ export interface ActivityItem {
   message: string;
   recipient?: string;
   imageUrl?: string;
+  postTitle?: string;
+  postUrl?: string;
 }
 
 export interface LogEntry {

tests/activity-log-origin.test.ts

@@ -0,0 +1,30 @@
+import { describe, expect, it } from 'vitest';
+import { ActivityLogRepository } from '../src/database/repositories.js';
+import { ActivityLog } from '../src/web/activity-log.js';
+import { createTestDb } from './testUtils.js';
+
+describe('activity origin context', () => {
+  it('persists and hydrates the source post title, URL, and image', () => {
+    const db = createTestDb();
+    const repository = new ActivityLogRepository(db);
+    const activity = new ActivityLog(repository);
+
+    activity.push(
+      'sent',
+      'Sent message to u/alice (r/example)',
+      'alice',
+      'https://i.redd.it/source.jpg',
+      {
+        postTitle: 'Source title',
+        postUrl: 'https://www.reddit.com/r/example/comments/source/source_title/',
+      },
+    );
+
+    expect(new ActivityLog(repository).recent(1)).toEqual([expect.objectContaining({
+      imageUrl: 'https://i.redd.it/source.jpg',
+      postTitle: 'Source title',
+      postUrl: 'https://www.reddit.com/r/example/comments/source/source_title/',
+    })]);
+    db.close();
+  });
+});

tests/browser-client.test.ts

@@ -1,5 +1,5 @@
 import { describe, expect, it, vi } from 'vitest';
-import type { BrowserContext } from 'playwright';
+import type { BrowserContext, Page } from 'playwright';
 import { BrowserClient, type BrowserRuntime } from '../src/browser/client.js';
 import type { Logger } from '../src/utils/logger.js';
 import { getTestConfig } from './testUtils.js';
@@ -35,4 +35,25 @@ describe('BrowserClient', () => {
     expect(client.getSessionState()).toBe('unknown');
     expect(JSON.stringify(logger)).not.toContain('secret');
   });
+
+  it('reads the username from Reddit\'s nested me.json account response', async () => {
+    const fetchMock = vi.fn().mockResolvedValue({
+      ok: true,
+      json: async () => ({ kind: 't2', data: { name: 'bot-account' } }),
+    });
+    vi.stubGlobal('fetch', fetchMock);
+    const page = {
+      evaluate: async (pageFunction: () => Promise<string | null>) => pageFunction(),
+    } as unknown as Page;
+    const context = { pages: () => [page] } as unknown as BrowserContext;
+    const runtime: BrowserRuntime = { launchPersistentContext: vi.fn().mockResolvedValue(context) };
+    const client = new BrowserClient(getTestConfig(), createLogger(), runtime);
+
+    await expect(client.getAuthenticatedUsername()).resolves.toBe('bot-account');
+    expect(fetchMock).toHaveBeenCalledWith(
+      'https://www.reddit.com/api/me.json',
+      { credentials: 'include' },
+    );
+    vi.unstubAllGlobals();
+  });
 });

tests/chat-service-auth-gate.test.ts

@@ -34,8 +34,79 @@ describe('ChatService account authentication gate', () => {
       auth,
     );
 
-    await service.refreshTopChats();
+    await expect(service.refreshTopChats()).rejects.toThrow(
+      'Matrix authentication could not be restored',
+    );
 
     expect(matrix.sync).not.toHaveBeenCalled();
   });
+
+  it('coalesces concurrent delta refresh requests before they reach Matrix', async () => {
+    const logger = createMockLogger();
+    const matrix = new MatrixClient({
+      homeserver: 'https://matrix.example.test',
+      accessToken: 'verified',
+      userId: '@t2_account:reddit.com',
+      capturedAt: 1,
+    }, logger, { minRequestIntervalMs: 0 });
+    let finishSync!: (value: { next_batch: string }) => void;
+    matrix.sync = vi.fn(() => new Promise((resolve) => {
+      finishSync = resolve;
+    })) as typeof matrix.sync;
+    const cache = new ChatCache(
+      logger,
+      path.join(os.tmpdir(), `chat-auth-${Date.now()}-${Math.random()}.json`),
+    );
+    const service = new ChatService(
+      matrix,
+      logger,
+      undefined,
+      undefined,
+      undefined,
+      undefined,
+      cache,
+      undefined,
+      undefined,
+      { isFullyAuthenticated: () => true, invalidate: vi.fn() },
+    );
+
+    const first = service.refreshTopChats();
+    const second = service.refreshTopChats();
+    await vi.waitFor(() => expect(matrix.sync).toHaveBeenCalledOnce());
+    finishSync({ next_batch: 's1' });
+
+    await expect(Promise.all([first, second])).resolves.toEqual([undefined, undefined]);
+    expect(matrix.sync).toHaveBeenCalledOnce();
+  });
+
+  it('reports failed sync termination to progress listeners', async () => {
+    const logger = createMockLogger();
+    const matrix = new MatrixClient({
+      homeserver: 'https://matrix.example.test',
+      accessToken: 'unverified',
+      userId: '@t2_account:reddit.com',
+      capturedAt: 1,
+    }, logger, { minRequestIntervalMs: 0 });
+    const service = new ChatService(
+      matrix,
+      logger,
+      undefined,
+      undefined,
+      undefined,
+      undefined,
+      new ChatCache(logger, path.join(os.tmpdir(), `chat-auth-${Date.now()}-${Math.random()}.json`)),
+      undefined,
+      undefined,
+      { isFullyAuthenticated: () => false, invalidate: vi.fn() },
+    );
+    const listener = vi.fn();
+    service.setProgressListener(listener);
+
+    await expect(service.refreshTopChats()).rejects.toThrow();
+
+    expect(listener).toHaveBeenLastCalledWith(null, {
+      status: 'failed',
+      error: 'Matrix authentication could not be restored',
+    });
+  });
 });

tests/chat-service-progressive-backfill.test.ts

@@ -0,0 +1,197 @@
+import fs from 'fs/promises';
+import os from 'os';
+import path from 'path';
+import { describe, expect, it, vi } from 'vitest';
+import { ChatCache } from '../src/services/chat/cache.js';
+import { MatrixClient } from '../src/services/chat/matrix/client.js';
+import type { MatrixMessagesResponse } from '../src/services/chat/matrix/types.js';
+import { ChatService } from '../src/services/chat/service.js';
+import { createMockLogger } from './mockLogger.js';
+import { authenticatedAccountAuth, createTestDb, createTestRepositories } from './testUtils.js';
+
+const credentials = {
+  homeserver: 'https://matrix.example.test',
+  accessToken: 'token',
+  userId: '@me:reddit.com',
+  capturedAt: Date.now(),
+};
+
+describe('ChatService progressive full backfill', () => {
+  it('records replies for performance only when the room has source context', async () => {
+    const logger = createMockLogger();
+    const tmpDir = await fs.mkdtemp(path.join(os.tmpdir(), 'chat-performance-context-'));
+    const db = createTestDb();
+    const repos = createTestRepositories(db);
+
+    try {
+      repos.postsRepo.insert({
+        id: 'post-alice',
+        subreddit: 'example',
+        author: 'alice',
+        title: 'Source post',
+        imageUrl: null,
+        processedAt: 1_000,
+      });
+      repos.messagesRepo.insert({
+        postId: 'post-alice',
+        recipient: 'alice',
+        subject: 'alice',
+        message: 'Hello Alice',
+        sentAt: Date.now(),
+        strategyId: 'direct',
+        chatRoomId: '!alice:reddit.com',
+      });
+
+      const matrix = new MatrixClient(credentials, logger, { minRequestIntervalMs: 0 });
+      matrix.sync = vi.fn(async () => ({ next_batch: 's1', rooms: { join: {} } })) as typeof matrix.sync;
+      matrix.getJoinedRooms = vi.fn(async () => ['!alice:reddit.com', '!bob:reddit.com']);
+      matrix.getRoomMessages = vi.fn(async (roomId: string) => ({
+        chunk: [
+          {
+            event_id: `$reply-${roomId}`,
+            type: 'm.room.message',
+            sender: roomId === '!alice:reddit.com' ? '@t2_alice:reddit.com' : '@t2_bob:reddit.com',
+            origin_server_ts: 2_000,
+            content: { body: 'Hi there' },
+          },
+          {
+            event_id: `$first-${roomId}`,
+            type: 'm.room.message',
+            sender: '@me:reddit.com',
+            origin_server_ts: 1_000,
+            content: { body: roomId === '!alice:reddit.com' ? 'Hello Alice' : 'Hello Bob' },
+          },
+        ],
+        start: 'start',
+      }));
+
+      const service = new ChatService(
+        matrix,
+        logger,
+        repos.successfulMessagesRepo,
+        undefined,
+        undefined,
+        { resolveT2Ids: vi.fn(async () => ({ t2_alice: 'alice', t2_bob: 'bob' })) },
+        new ChatCache(logger, path.join(tmpDir, 'chat-cache.json')),
+        repos.messagesRepo,
+        undefined,
+        authenticatedAccountAuth,
+      );
+
+      await service.fetchAllMessages();
+
+      expect(repos.messagesRepo.getByChatRoomId('!alice:reddit.com')?.gotResponse).toBe(true);
+      expect(repos.messagesRepo.getByChatRoomId('!bob:reddit.com')).toBeUndefined();
+      expect(repos.messagesRepo.getResponseRateTrend()).toEqual([
+        expect.objectContaining({ totalSent: 1, totalResponses: 1, responseRate: 100 }),
+      ]);
+      expect(repos.successfulMessagesRepo.getRecent()).toEqual([
+        expect.objectContaining({
+          originalMessage: 'Hello Alice',
+          postTitle: 'Source post',
+          subreddit: 'example',
+        }),
+      ]);
+    } finally {
+      db.close();
+      await fs.rm(tmpDir, { recursive: true, force: true });
+    }
+  });
+
+  it('publishes room summaries and recent timeline messages before deep history finishes', async () => {
+    const logger = createMockLogger();
+    const tmpDir = await fs.mkdtemp(path.join(os.tmpdir(), 'chat-progressive-backfill-'));
+    let finishHistory!: (response: MatrixMessagesResponse) => void;
+    const pendingHistory = new Promise<MatrixMessagesResponse>((resolve) => {
+      finishHistory = resolve;
+    });
+    let finishUsernameResolution!: (usernames: Record<string, string>) => void;
+    const pendingUsernames = new Promise<Record<string, string>>((resolve) => {
+      finishUsernameResolution = resolve;
+    });
+
+    try {
+      const matrix = new MatrixClient(credentials, logger, { minRequestIntervalMs: 0 });
+      matrix.sync = vi.fn(async () => ({
+        next_batch: 's1',
+        rooms: {
+          join: {
+            '!alice:reddit.com': {
+              summary: { 'm.heroes': ['@t2_alice:reddit.com'] },
+              timeline: {
+                events: [
+                  {
+                    event_id: '$first',
+                    type: 'm.room.message',
+                    sender: '@me:reddit.com',
+                    origin_server_ts: 1_000,
+                    content: { body: 'Hello Alice' },
+                  },
+                  {
+                    event_id: '$reply',
+                    type: 'm.room.message',
+                    sender: '@t2_alice:reddit.com',
+                    origin_server_ts: 2_000,
+                    content: { body: 'Hi there' },
+                  },
+                ],
+              },
+            },
+          },
+        },
+      })) as typeof matrix.sync;
+      matrix.getJoinedRooms = vi.fn(async () => ['!alice:reddit.com']);
+      matrix.getRoomMessages = vi.fn(() => pendingHistory);
+      const usernameResolver = {
+        resolveT2Ids: vi.fn(() => pendingUsernames),
+      };
+
+      const cachePath = path.join(tmpDir, 'chat-cache.json');
+      const service = new ChatService(
+        matrix,
+        logger,
+        undefined,
+        undefined,
+        undefined,
+        usernameResolver,
+        new ChatCache(logger, cachePath),
+        undefined,
+        undefined,
+        authenticatedAccountAuth,
+      );
+
+      const backfill = service.fetchAllMessages();
+      await vi.waitFor(() => expect(usernameResolver.resolveT2Ids).toHaveBeenCalledOnce());
+
+      const visibleChats = await service.getCachedConversations();
+      expect(visibleChats).toHaveLength(1);
+      expect(visibleChats[0]).toMatchObject({
+        roomId: '!alice:reddit.com',
+        username: 't2_alice',
+        lastMessageSnippet: 'Hi there',
+        messages: [
+          { text: 'Hello Alice', isSelf: true },
+          { text: 'Hi there', isSelf: false },
+        ],
+      });
+      expect(usernameResolver.resolveT2Ids).toHaveBeenCalledWith(['t2_alice']);
+
+      const persisted = JSON.parse(await fs.readFile(cachePath, 'utf-8')) as { chats: unknown[] };
+      expect(persisted.chats).toHaveLength(1);
+
+      finishUsernameResolution({ t2_alice: 'alice' });
+      await vi.waitFor(() => expect(matrix.getRoomMessages).toHaveBeenCalledOnce());
+      await vi.waitFor(async () => {
+        const enrichedChats = await service.getCachedConversations();
+        expect(enrichedChats[0].username).toBe('alice');
+      });
+
+      finishHistory({ chunk: [], start: 'start' });
+      await backfill;
+    } finally {
+      finishUsernameResolution({});
+      finishHistory({ chunk: [], start: 'start' });
+      await fs.rm(tmpDir, { recursive: true, force: true });
+    }
+  });
+});

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

@@ -70,6 +70,73 @@ describe('ChatService username persistence', () => {
     expect(svc.resolveSenderDisplay('@t2_unknown:reddit.com')).toBe('t2_unknown');
   });
 
+  it('starts a conversation with the t2 ID supplied by the Reddit listing', async () => {
+    const logger = createMockLogger();
+    const matrix = buildMatrix();
+    matrix.sendInitialDirectMessage = vi.fn().mockResolvedValue({
+      roomId: '!room:reddit.com',
+      eventId: '$event',
+    });
+    const usernameResolver = {
+      resolveT2Ids: vi.fn().mockResolvedValue({}),
+      resolveUsernameToT2: vi.fn().mockRejectedValue(new Error('profile lookup returned 403')),
+    };
+    const svc = new ChatService(
+      matrix,
+      logger,
+      undefined, undefined, undefined, usernameResolver,
+      tmpCache(logger),
+      undefined,
+      undefined,
+      authenticatedAccountAuth,
+    );
+
+    const chat = await svc.startConversation('alice', 'hello', 't2_abc123');
+
+    expect(chat?.username).toBe('alice');
+    expect(usernameResolver.resolveUsernameToT2).not.toHaveBeenCalled();
+    expect(matrix.sendInitialDirectMessage).toHaveBeenCalledWith(
+      '@t2_abc123:reddit.com',
+      'hello',
+    );
+  });
+
+  it('uses the durable username mapping before a live profile lookup', async () => {
+    const db = new Database(':memory:');
+    runMigrations(db);
+    const repo = new RedditUsersRepository(db);
+    repo.upsert({ t2Id: 't2_cached', username: 'alice' });
+    const logger = createMockLogger();
+    const matrix = buildMatrix();
+    matrix.sendInitialDirectMessage = vi.fn().mockResolvedValue({
+      roomId: '!room:reddit.com',
+      eventId: '$event',
+    });
+    const usernameResolver = {
+      resolveT2Ids: vi.fn().mockResolvedValue({}),
+      resolveUsernameToT2: vi.fn().mockRejectedValue(new Error('profile lookup returned 403')),
+    };
+    const svc = new ChatService(
+      matrix,
+      logger,
+      undefined, undefined, undefined, usernameResolver,
+      tmpCache(logger),
+      undefined,
+      repo,
+      authenticatedAccountAuth,
+    );
+
+    const chat = await svc.startConversation('ALICE', 'hello');
+
+    expect(chat?.username).toBe('ALICE');
+    expect(usernameResolver.resolveUsernameToT2).not.toHaveBeenCalled();
+    expect(matrix.sendInitialDirectMessage).toHaveBeenCalledWith(
+      '@t2_cached:reddit.com',
+      'hello',
+    );
+    db.close();
+  });
+
   it('upgrades cached chats with t2_ usernames from the db map on loadCache', async () => {
     const db = new Database(':memory:');
     runMigrations(db);

tests/config-persistence.test.ts

@@ -1,128 +1,93 @@
-import fs from 'fs';
-import os from 'os';
-import path from 'path';
-import YAML from 'yaml';
-import { describe, it, expect, beforeEach, afterEach } from 'vitest';
-import { persistSubreddits } from '../src/config/persistence.js';
+import Database from 'better-sqlite3';
+import fs from 'node:fs';
+import os from 'node:os';
+import path from 'node:path';
+import { afterEach, beforeEach, describe, expect, it } from 'vitest';
+import { ConfigStore } from '../src/config/persistence.js';
+import { loadConfig } from '../src/config/index.js';
+import { runMigrations } from '../src/database/client.js';
+import { getTestConfig } from './testUtils.js';
 
-const SAMPLE = `# top-level note that must survive
-reddit:
-  # weights bias picking
-  subreddits:
-    - { name: AverageNudes, weight: 4, tone: 'direct' }    # validation seekers
-    - { name: gonewild40plus, weight: 4, tone: 'gentle' }  # mature
-    - { name: normalnudes, weight: 3 }                     # real bodies
-    - { name: tightandtoned, weight: 1 }
-
-  pollIntervalMs: 30000
-  userAgent: "ua"
-`;
-
-describe('persistSubreddits', () => {
-  let tmpDir: string;
-  let configPath: string;
+describe('ConfigStore', () => {
+  let db: Database.Database;
+  let store: ConfigStore;
 
   beforeEach(() => {
-    tmpDir = fs.mkdtempSync(path.join(os.tmpdir(), 'rb-config-'));
-    configPath = path.join(tmpDir, 'config.yaml');
-    fs.writeFileSync(configPath, SAMPLE, 'utf-8');
+    db = new Database(':memory:');
+    runMigrations(db);
+    store = new ConfigStore(db);
   });
 
-  afterEach(() => {
-    fs.rmSync(tmpDir, { recursive: true, force: true });
-  });
+  afterEach(() => db.close());
 
-  it('mutates an existing row in place and preserves its inline comment', () => {
-    persistSubreddits(
-      [
-        { name: 'AverageNudes', type: 'image', weight: 4, tone: 'playful' },
-        { name: 'gonewild40plus', type: 'image', weight: 4, tone: 'gentle' },
-        { name: 'normalnudes', type: 'image', weight: 3, tone: 'default' },
-        { name: 'tightandtoned', type: 'image', weight: 1, tone: 'default' },
-      ],
-      configPath,
-    );
-    const out = fs.readFileSync(configPath, 'utf-8');
-    expect(out).toMatch(/tone:\s*['"]?playful['"]?/);
-    expect(out).toContain('# validation seekers');
-    expect(out).toContain('# top-level note that must survive');
-    expect(out).toContain('# weights bias picking');
-    expect(out).toContain('# mature');
-    expect(out).toContain('pollIntervalMs: 30000');
-  });
-
-  it('drops removed rows (and their attached comments)', () => {
-    persistSubreddits(
-      [
-        { name: 'AverageNudes', type: 'image', weight: 4, tone: 'direct' },
-        { name: 'tightandtoned', type: 'image', weight: 1, tone: 'default' },
-      ],
-      configPath,
-    );
-    const out = fs.readFileSync(configPath, 'utf-8');
-    expect(out).not.toContain('gonewild40plus');
-    expect(out).not.toContain('normalnudes');
-    expect(out).not.toContain('# mature');
-    expect(out).toContain('AverageNudes');
-    expect(out).toContain('tightandtoned');
-    expect(out).toContain('# validation seekers');
-  });
-
-  it('appends new rows in caller order', () => {
-    persistSubreddits(
-      [
-        { name: 'AverageNudes', type: 'image', weight: 4, tone: 'direct' },
-        { name: 'gonewild40plus', type: 'image', weight: 4, tone: 'gentle' },
-        { name: 'normalnudes', type: 'image', weight: 3, tone: 'default' },
-        { name: 'tightandtoned', type: 'image', weight: 1, tone: 'default' },
-        { name: 'NewSub', type: 'chat', weight: 2, tone: 'playful' },
-      ],
-      configPath,
-    );
-    const parsed = YAML.parse(fs.readFileSync(configPath, 'utf-8'));
-    const subs = parsed.reddit.subreddits;
-    expect(subs[subs.length - 1]).toMatchObject({
-      name: 'NewSub',
-      type: 'chat',
-      weight: 2,
-      tone: 'playful',
+  it('round-trips application configuration through SQLite', () => {
+    const config = getTestConfig({
+      rateLimit: { minDelayBetweenMessagesMs: 42, maxMessagesPerHour: 7, jitterMs: 3 },
     });
+    store.save(config);
+
+    const loaded = store.load({
+      OPENROUTER_API_KEY: 'environment-key',
+      WEB_DASHBOARD_TOKEN: 'environment-dashboard-token',
+      DATABASE_PATH: './data/from-environment.db',
+    });
+
+    expect(loaded?.rateLimit).toEqual(config.rateLimit);
+    expect(loaded?.openrouter.apiKey).toBe('environment-key');
+    expect(loaded?.web.authToken).toBe('environment-dashboard-token');
+    expect(loaded?.database.path).toBe('./data/from-environment.db');
   });
 
-  it("omits 'default' tone and 'image' type on write to match on-disk style", () => {
-    persistSubreddits(
-      [{ name: 'OnlyOne', type: 'image', weight: 1, tone: 'default' }],
-      configPath,
-    );
-    const out = fs.readFileSync(configPath, 'utf-8');
-    expect(out).not.toMatch(/tone:\s*default/);
-    expect(out).not.toMatch(/type:\s*image/);
+  it('never stores secrets in the database record', () => {
+    const config = getTestConfig();
+    config.openrouter.apiKey = 'database-must-not-contain-this';
+    config.web.authToken = 'also-secret';
+    store.save(config);
+
+    const row = db.prepare('SELECT config_json FROM app_config WHERE id = 1').get() as { config_json: string };
+    expect(row.config_json).not.toContain('database-must-not-contain-this');
+    expect(row.config_json).not.toContain('also-secret');
+    expect(JSON.parse(row.config_json)).not.toHaveProperty('database');
   });
 
-  it('atomic write — tmp file not left behind on success', () => {
-    persistSubreddits(
-      [{ name: 'OnlyOne', type: 'image', weight: 1, tone: 'direct' }],
-      configPath,
-    );
-    expect(fs.existsSync(configPath + '.tmp')).toBe(false);
+  it('updates the singleton record instead of appending versions', () => {
+    store.save(getTestConfig());
+    store.save(getTestConfig({ browser: { sessionDir: './data/browser-session', dryRun: true } }));
+
+    expect(db.prepare('SELECT COUNT(*) AS count FROM app_config').get()).toEqual({ count: 1 });
+    expect(store.load({
+      OPENROUTER_API_KEY: 'key',
+      WEB_DASHBOARD_TOKEN: 'dashboard-token',
+    })?.browser.dryRun).toBe(true);
   });
 
-  it('reorders rows according to input order', () => {
-    persistSubreddits(
-      [
-        { name: 'tightandtoned', type: 'image', weight: 1, tone: 'default' },
-        { name: 'AverageNudes', type: 'image', weight: 4, tone: 'direct' },
-        { name: 'gonewild40plus', type: 'image', weight: 4, tone: 'gentle' },
-        { name: 'normalnudes', type: 'image', weight: 3, tone: 'default' },
-      ],
-      configPath,
-    );
-    const parsed = YAML.parse(fs.readFileSync(configPath, 'utf-8'));
-    expect(parsed.reddit.subreddits.map((s: { name: string }) => s.name)).toEqual([
-      'tightandtoned',
-      'AverageNudes',
-      'gonewild40plus',
-      'normalnudes',
-    ]);
+  it('imports legacy YAML once and then starts without the file', () => {
+    const originalDirectory = process.cwd();
+    const tempDirectory = fs.mkdtempSync(path.join(os.tmpdir(), 'redditbot-config-import-'));
+    const previousApiKey = process.env.OPENROUTER_API_KEY;
+    const previousDashboardToken = process.env.WEB_DASHBOARD_TOKEN;
+    try {
+      process.chdir(tempDirectory);
+      process.env.OPENROUTER_API_KEY = 'environment-key';
+      process.env.WEB_DASHBOARD_TOKEN = 'environment-dashboard-token';
+      fs.writeFileSync('config.yaml', `
+reddit:
+  subreddits: [example]
+openrouter:
+  imageAnalysisPrompt: analyze
+  messageGenerationPrompt: compose
+`);
+
+      expect(loadConfig(store).reddit.subreddits[0].name).toBe('example');
+      fs.rmSync('config.yaml');
+      expect(loadConfig(store).reddit.subreddits[0].name).toBe('example');
+    } finally {
+      process.chdir(originalDirectory);
+      fs.rmSync(tempDirectory, { recursive: true, force: true });
+      if (previousApiKey === undefined) delete process.env.OPENROUTER_API_KEY;
+      else process.env.OPENROUTER_API_KEY = previousApiKey;
+      if (previousDashboardToken === undefined) delete process.env.WEB_DASHBOARD_TOKEN;
+      else process.env.WEB_DASHBOARD_TOKEN = previousDashboardToken;
+    }
   });
 });

tests/dashboard/app.test.tsx

@@ -171,6 +171,7 @@ describe('dashboard foundation', () => {
     expect(screen.getByText('Dry run')).toBeInTheDocument();
     expect(await screen.findByRole('list', { name: 'Recent sent messages' })).toHaveTextContent('A recent opener');
     expect(screen.getByRole('list', { name: 'Recent sent messages' })).toHaveTextContent('Responded');
+    expect(screen.getByRole('link', { name: 'u/alice' })).toHaveAttribute('href', 'https://www.reddit.com/u/alice');
   });
 
   it('keeps stats visible when timers fail and retries only the failed panel', async () => {
@@ -200,6 +201,52 @@ describe('dashboard foundation', () => {
     expect(timerRequests).toBe(2);
   });
 
+  it('makes usernames in recent activity clickable', async () => {
+    installSuccessfulApi({
+      recentActivity: [{
+        timestamp: Date.now(),
+        type: 'response',
+        message: 'Reply from u/alice',
+        recipient: 'alice',
+      }],
+    });
+    renderDashboard();
+
+    const activity = await screen.findByRole('heading', { name: 'Recent activity' });
+    const panel = activity.closest('section');
+    expect(panel).not.toBeNull();
+    expect(within(panel!).getByRole('link', { name: 'u/alice' })).toHaveAttribute(
+      'href',
+      'https://www.reddit.com/u/alice',
+    );
+  });
+
+  it('opens saved source-post context from a sent activity entry', async () => {
+    installSuccessfulApi({
+      recentActivity: [{
+        timestamp: Date.now(),
+        type: 'sent',
+        message: 'Sent message to u/alice (r/example)',
+        recipient: 'alice',
+        imageUrl: 'https://i.redd.it/source.jpg',
+        postTitle: 'The source post title',
+        postUrl: 'https://www.reddit.com/r/example/comments/source/the_source_post_title/',
+      }],
+    });
+    const user = userEvent.setup();
+    renderDashboard();
+
+    await user.click(await screen.findByRole('button', { name: 'Sent message to u/alice (r/example)' }));
+
+    const dialog = screen.getByRole('dialog', { name: 'The source post title' });
+    expect(within(dialog).getByRole('img', { name: 'Source post: The source post title' })).toHaveAttribute(
+      'src', 'https://i.redd.it/source.jpg',
+    );
+    expect(within(dialog).getByRole('link', { name: 'Open Reddit post' })).toHaveAttribute(
+      'href', 'https://www.reddit.com/r/example/comments/source/the_source_post_title/',
+    );
+  });
+
   it('styles the recent-messages retry control when its request fails', async () => {
     installSuccessfulApi();
     server.use(http.get('/api/messages', () => HttpResponse.json({ error: 'Messages unavailable' }, { status: 503 })));

tests/dashboard/conversations.test.tsx

@@ -15,6 +15,7 @@ interface ChatFixtureOptions {
   unread?: boolean;
   isFromUs?: boolean;
   lastMessageSnippet?: string;
+  hasReceivedImages?: boolean;
 }
 
 function chatFixture(options: ChatFixtureOptions) {
@@ -27,6 +28,7 @@ function chatFixture(options: ChatFixtureOptions) {
     lastMessageSnippet: options.lastMessageSnippet ?? `Latest from ${options.username}`,
     isFromUs: options.isFromUs ?? false,
     unread: options.unread ?? false,
+    ...(options.hasReceivedImages === undefined ? {} : { hasReceivedImages: options.hasReceivedImages }),
   };
 }
 
@@ -45,6 +47,7 @@ function detailFixture(chat = alice) {
       subreddit: 'casualconversation',
       title: 'Looking for a chat',
       url: 'https://reddit.com/r/casualconversation/comments/post-1',
+      imageUrl: 'https://i.redd.it/source-post.jpg',
       sentAt: 1_785_999_800_000,
     },
     syncInProgress: null,
@@ -123,8 +126,59 @@ describe('ConversationsPage', () => {
 
     await user.click(screen.getByRole('button', { name: /u\/alice/ }));
     expect(await screen.findByRole('heading', { name: 'u/alice' })).toBeInTheDocument();
+    expect(screen.getAllByRole('link', { name: 'u/alice' })).not.toHaveLength(0);
+    for (const profileLink of screen.getAllByRole('link', { name: 'u/alice' })) {
+      expect(profileLink).toHaveAttribute('href', 'https://www.reddit.com/u/alice');
+    }
     expect(screen.getByText('Good to hear from you')).toBeInTheDocument();
     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',
+      'https://i.redd.it/source-post.jpg',
+    );
+  });
+
+  it('marks and filters conversations with received images and renders the images in chat', async () => {
+    const imageChat = chatFixture({
+      username: 'alice',
+      roomId: 'room-alice',
+      hasReceivedImages: true,
+      lastMessageSnippet: '[Image]',
+    });
+    server.use(
+      http.get('/api/conversations', () => HttpResponse.json([imageChat, bob])),
+      http.get('/api/conversations/room-alice', () => HttpResponse.json({
+        ...detailFixture(imageChat),
+        messages: [
+          {
+            sender: 'alice',
+            text: '[Image]',
+            timestamp: 1_786_000_000_000,
+            isSelf: false,
+            media: [{
+              originalUrl: 'mxc://reddit.com/image-one',
+              localPath: 'received image.jpg',
+              fileName: 'received image.jpg',
+            }],
+          },
+        ],
+      })),
+    );
+    const user = userEvent.setup();
+    renderConversations();
+
+    const aliceItem = await screen.findByRole('button', { name: /u\/alice/ });
+    expect(screen.getByText('Image received')).toBeInTheDocument();
+
+    await user.selectOptions(screen.getByRole('combobox', { name: 'Filter conversations' }), 'received-images');
+    expect(screen.getByRole('button', { name: /u\/alice/ })).toBeInTheDocument();
+    expect(screen.queryByRole('button', { name: /u\/bob/ })).not.toBeInTheDocument();
+
+    await user.click(screen.getByRole('button', { name: /u\/alice/ }));
+    expect(await screen.findByRole('img', { name: 'Image received from u/alice' })).toHaveAttribute(
+      'src',
+      '/media/received%20image.jpg',
+    );
   });
 
   it('turns a suggestion into an editable draft and confirms sending without losing failed input', async () => {
@@ -230,6 +284,8 @@ describe('ConversationsPage', () => {
     );
     await user.click(screen.getByRole('button', { name: 'Start conversation' }));
     expect(await screen.findByRole('status', { name: 'Conversation started' })).toHaveTextContent('Conversation started with u/charlie');
+    expect(within(screen.getByRole('status', { name: 'Conversation started' })).getByRole('link', { name: 'u/charlie' }))
+      .toHaveAttribute('href', 'https://www.reddit.com/u/charlie');
     expect(username).toHaveValue('');
     expect(message).toHaveValue('');
     expect(startRequests).toBe(2);

tests/dashboard/media.test.tsx

@@ -89,6 +89,9 @@ describe('media page', () => {
 
     const aliceImage = await screen.findByRole('img', { name: 'Media from alice' });
     const charlieImage = screen.getByRole('img', { name: 'Media from charlie' });
+    for (const profileLink of screen.getAllByRole('link', { name: 'alice' })) {
+      expect(profileLink).toHaveAttribute('href', 'https://www.reddit.com/u/alice');
+    }
     expect(aliceImage).toHaveClass('is-blurred');
     expect(charlieImage).toHaveClass('is-blurred');
     expect(credentials.every((value) => value === 'same-origin')).toBe(true);

tests/dashboard/performance-operations.test.tsx

@@ -124,7 +124,9 @@ describe('OperationsPage', () => {
 
     expect(await screen.findByRole('heading', { name: 'Operations' })).toBeInTheDocument();
     const activityRegion = screen.getByRole('region', { name: 'Activity' });
-    expect(await within(activityRegion).findByText('Reply from u/alex')).toBeInTheDocument();
+    expect(await within(activityRegion).findByRole('link', { name: 'u/alex' })).toBeInTheDocument();
+    expect(within(activityRegion).getByText((_content, element) => element?.tagName === 'STRONG' && element.textContent === 'Reply from u/alex')).toBeInTheDocument();
+    expect(within(activityRegion).getByRole('link', { name: 'u/alex' })).toHaveAttribute('href', 'https://www.reddit.com/u/alex');
     const jobsRegion = screen.getByRole('region', { name: 'Sync jobs' });
     expect(await within(jobsRegion).findByText('4 of 10')).toBeInTheDocument();
     for (const name of ['Sync latest chats', 'Full cache sync', 'Fetch all chats']) {

tests/dashboard/realtime-client.test.ts

@@ -83,6 +83,16 @@ describe('dashboard realtime client', () => {
         type: 'sync.progress',
         payload: { syncId: 'sync-1', kind: 'media', completed: 2, total: 5 },
       }),
+    ).toEqual([
+      ['operations', 'sync-status'],
+    ]);
+    expect(
+      queryKeysForDashboardEvent({
+        id: 'completed',
+        occurredAt: '2026-08-08T12:00:01.000Z',
+        type: 'sync.completed',
+        payload: { syncId: 'sync-1', kind: 'conversations', processed: 5 },
+      }),
     ).toEqual([
       ['operations', 'sync-status'],
       ['conversations'],

tests/dashboard/reddit-username-link.test.tsx

@@ -0,0 +1,48 @@
+// @vitest-environment jsdom
+
+import '@testing-library/jest-dom/vitest';
+import { render, screen } from '@testing-library/react';
+import { describe, expect, it } from 'vitest';
+import { RedditUsernameLink } from '../../apps/dashboard/src/components/reddit-username-link.js';
+import { RedditUserText } from '../../apps/dashboard/src/components/reddit-user-text.js';
+
+describe('RedditUsernameLink', () => {
+  it('normalizes a username and opens its Reddit profile in a new tab', () => {
+    render(<RedditUsernameLink username="u/example user" />);
+
+    expect(screen.getByRole('link', { name: 'u/example user' })).toHaveAttribute(
+      'href',
+      'https://www.reddit.com/u/example%20user',
+    );
+    expect(screen.getByRole('link', { name: 'u/example user' })).toHaveAttribute('target', '_blank');
+    expect(screen.getByRole('link', { name: 'u/example user' })).toHaveAttribute('rel', 'noreferrer');
+  });
+
+  it('can preserve an existing unprefixed display label', () => {
+    render(<RedditUsernameLink showPrefix={false} username="alice" />);
+
+    expect(screen.getByRole('link', { name: 'alice' })).toHaveAttribute(
+      'href',
+      'https://www.reddit.com/u/alice',
+    );
+  });
+
+  it('never exposes or links an internal t2 identity', () => {
+    const view = render(<RedditUsernameLink username="@t2_private123:reddit.com" />);
+
+    expect(view.container).not.toHaveTextContent('t2_private123');
+    expect(view.container.querySelector('a')).toBeNull();
+    expect(view.container).toHaveTextContent('Unknown Reddit user');
+  });
+
+  it('links username mentions embedded in activity text and redacts raw ids', () => {
+    render(<RedditUserText>Reply from u/alice after syncing t2_private123</RedditUserText>);
+
+    expect(screen.getByRole('link', { name: 'u/alice' })).toHaveAttribute(
+      'href',
+      'https://www.reddit.com/u/alice',
+    );
+    expect(screen.queryByText(/t2_private123/)).not.toBeInTheDocument();
+    expect(screen.getByText(/after syncing Reddit user/)).toBeInTheDocument();
+  });
+});

tests/dashboard/route-filters.test.tsx

@@ -32,10 +32,10 @@ describe('route-friendly filters', () => {
   it('hydrates and writes conversation search and status filters', async () => {
     server.use(http.get('/api/conversations', () => HttpResponse.json([])));
     const user = userEvent.setup();
-    renderRoute('/conversations?q=alice&filter=unread', <ConversationRoute />);
+    renderRoute('/conversations?q=alice&filter=received-images', <ConversationRoute />);
     const search = await screen.findByRole('searchbox', { name: 'Search conversations' });
     expect(search).toHaveValue('alice');
-    expect(screen.getByRole('combobox', { name: 'Filter conversations' })).toHaveValue('unread');
+    expect(screen.getByRole('combobox', { name: 'Filter conversations' })).toHaveValue('received-images');
     await user.clear(search);
     await user.type(search, 'bob');
     expect(screen.getByLabelText('Current URL')).toHaveTextContent('q=bob');

tests/dashboard/settings.test.tsx

@@ -16,6 +16,7 @@ const config = {
   reddit: { prioritizeRecentPosts: false, recentWindowMinutes: 60 },
   subreddits: [{ name: 'casualconversation', type: 'chat', weight: 2, tone: 'default' }],
   tones: ['default', 'dominant', 'submissive', 'playful', 'direct', 'gentle', 'kink-friendly', 'teasing'],
+  advanced: { openrouter: { chatModel: 'example/chat-model' } },
 };
 
 const server = setupServer();
@@ -228,6 +229,25 @@ describe('settings and access', () => {
     expect(updateRequests).toBe(1);
   });
 
+  it('validates advanced application JSON before saving', async () => {
+    installConfigApi();
+    let updateRequests = 0;
+    server.use(http.put('/api/config', () => {
+      updateRequests += 1;
+      return HttpResponse.json({ success: true, config, subreddits: config.subreddits });
+    }));
+    const user = userEvent.setup();
+    renderSettings('/settings?section=behaviour');
+
+    const editor = await screen.findByRole('textbox', { name: 'Advanced configuration JSON' });
+    await user.clear(editor);
+    await user.type(editor, 'invalid');
+    await user.click(screen.getByRole('button', { name: 'Save settings' }));
+
+    expect(screen.getByText('Advanced configuration is not valid JSON.')).toBeInTheDocument();
+    expect(updateRequests).toBe(0);
+  });
+
   it('confirms unusually large hourly limits', async () => {
     installConfigApi();
     let updateRequests = 0;
@@ -287,6 +307,10 @@ describe('settings and access', () => {
     expect(importRequests).toBe(1);
     expect(await screen.findByText('Authenticated')).toBeInTheDocument();
     expect(screen.getByText(/u\/example-account/)).toBeInTheDocument();
+    expect(screen.getByRole('link', { name: 'u/example-account' })).toHaveAttribute(
+      'href',
+      'https://www.reddit.com/u/example-account',
+    );
 
     await user.click(screen.getByRole('button', { name: 'Recheck session' }));
     expect(statusRequests).toBeGreaterThanOrEqual(2);

tests/database.test.ts

@@ -105,16 +105,18 @@ describe('Database Client', () => {
       const tables = db
         .prepare("SELECT name FROM sqlite_master WHERE type='table' AND name NOT LIKE 'sqlite_%'")
         .all() as { name: string }[];
-      // processed_posts, sent_messages, successful_messages, activity_log, reddit_users, delivery_outbox, conversation_states, conversation_outcomes
-      expect(tables.length).toBe(8);
+      // Eight domain tables plus the singleton application configuration table.
+      expect(tables.length).toBe(9);
     });
 
     it('tracks schema version and migrates a legacy sent_messages table transactionally', () => {
       db.exec(`
         CREATE TABLE processed_posts (id TEXT PRIMARY KEY, subreddit TEXT NOT NULL, author TEXT NOT NULL, title TEXT NOT NULL, image_url TEXT, image_analysis TEXT, generated_message TEXT, processed_at INTEGER NOT NULL, message_sent INTEGER DEFAULT 0, error TEXT);
         CREATE TABLE sent_messages (id INTEGER PRIMARY KEY AUTOINCREMENT, post_id TEXT NOT NULL, recipient TEXT NOT NULL, subject TEXT NOT NULL, message TEXT NOT NULL, sent_at INTEGER NOT NULL);
+        CREATE TABLE activity_log (id INTEGER PRIMARY KEY AUTOINCREMENT, timestamp INTEGER NOT NULL, type TEXT NOT NULL, message TEXT NOT NULL, recipient TEXT, image_url TEXT);
         INSERT INTO processed_posts VALUES ('post-1', 'test', 'author', 'title', NULL, NULL, NULL, 1, 0, NULL);
         INSERT INTO sent_messages (post_id, recipient, subject, message, sent_at) VALUES ('post-1', 'recipient', 'subject', 'message', 2);
+        INSERT INTO activity_log (timestamp, type, message, recipient) VALUES (2, 'sent', 'Sent message to u/recipient (r/test)', 'recipient');
       `);
 
       runMigrations(db);
@@ -124,6 +126,10 @@ describe('Database Client', () => {
       const postId = db.prepare('PRAGMA table_info(sent_messages)').all().find((column: { name: string }) => column.name === 'post_id') as { notnull: number };
       expect(postId.notnull).toBe(0);
       expect(db.prepare("SELECT name FROM sqlite_master WHERE type = 'table' AND name = 'delivery_outbox'").get()).toBeDefined();
+      expect(db.prepare('SELECT post_title, post_url FROM activity_log').get()).toEqual({
+        post_title: 'title',
+        post_url: 'https://www.reddit.com/r/test/comments/post-1/',
+      });
     });
 
     it('processed_posts has correct schema', () => {

tests/matrix-client.test.ts

@@ -1,5 +1,9 @@
-import { describe, it, expect } from 'vitest';
-import { MatrixClient, MatrixRateLimitError } from '../src/services/chat/matrix/client.js';
+import { describe, it, expect, vi } from 'vitest';
+import {
+  MatrixAuthError,
+  MatrixClient,
+  MatrixRateLimitError,
+} from '../src/services/chat/matrix/client.js';
 import { createMockLogger } from './mockLogger.js';
 
 const creds = {
@@ -10,6 +14,31 @@ const creds = {
 };
 
 describe('MatrixClient HTTP timeout', () => {
+  it('loads an encoded Matrix user profile with bearer authentication', async () => {
+    let requestedUrl = '';
+    let authorization = '';
+    const fetchImpl = ((url: string | URL | Request, init?: RequestInit) => {
+      requestedUrl = String(url);
+      authorization = new Headers(init?.headers).get('Authorization') ?? '';
+      return Promise.resolve(new Response(JSON.stringify({ displayname: 'MilkyBabe_10' }), {
+        status: 200,
+        headers: { 'content-type': 'application/json' },
+      }));
+    }) as typeof fetch;
+    const client = new MatrixClient(creds, createMockLogger(), {
+      minRequestIntervalMs: 0,
+      fetchImpl,
+    });
+
+    await expect(client.getUserProfile('@t2_26q364ua7n:reddit.com')).resolves.toEqual({
+      displayname: 'MilkyBabe_10',
+    });
+    expect(requestedUrl).toBe(
+      'https://matrix.example.test/_matrix/client/v3/profile/%40t2_26q364ua7n%3Areddit.com',
+    );
+    expect(authorization).toBe('Bearer tok');
+  });
+
   it('aborts a hanging fetch and surfaces a timeout error rather than blocking forever', async () => {
     // A fetch impl that never resolves on its own — only the AbortSignal can
     // end it. If the client lacked an AbortSignal, this test would hang.
@@ -64,6 +93,36 @@ describe('MatrixClient HTTP timeout', () => {
   }, 10_000);
 });
 
+describe('MatrixClient authentication classification', () => {
+  it('does not classify a room-level 403 as an expired account token', async () => {
+    const client = new MatrixClient(creds, createMockLogger(), {
+      minRequestIntervalMs: 0,
+      fetchImpl: vi.fn().mockResolvedValue(new Response('', { status: 403 })),
+    });
+
+    const error = await client.getRoomFullState('!left-room:example.test').catch((cause) => cause);
+
+    expect(error).toBeInstanceOf(Error);
+    expect(error).not.toBeInstanceOf(MatrixAuthError);
+    expect((error as Error).message).toMatch(/403/);
+  });
+
+  it('still classifies an explicit unknown-token 403 as authentication failure', async () => {
+    const client = new MatrixClient(creds, createMockLogger(), {
+      minRequestIntervalMs: 0,
+      fetchImpl: vi.fn().mockResolvedValue(new Response(JSON.stringify({
+        errcode: 'M_UNKNOWN_TOKEN',
+        error: 'Access token has expired',
+      }), {
+        status: 403,
+        headers: { 'content-type': 'application/json' },
+      })),
+    });
+
+    await expect(client.whoami()).rejects.toBeInstanceOf(MatrixAuthError);
+  });
+});
+
 describe('MatrixClient 429 handling', () => {
   it('throws MatrixRateLimitError on a long retry_after rather than sleeping it out', async () => {
     const fetchImpl = (() =>

tests/matrix-http-media-downloader.test.ts

@@ -0,0 +1,25 @@
+import { describe, expect, it, vi } from 'vitest';
+import { MatrixMediaDownloader } from '../src/services/chat/matrix/http-media-downloader.js';
+import { createMockLogger } from './mockLogger.js';
+
+describe('MatrixMediaDownloader', () => {
+  it('uses replacement Matrix credentials for subsequent media downloads', async () => {
+    const staleClient = { downloadMedia: vi.fn().mockRejectedValue(new Error('expired')) };
+    const freshClient = {
+      downloadMedia: vi.fn().mockResolvedValue({
+        bytes: Buffer.from('fresh-image'),
+        contentType: 'image/jpeg',
+      }),
+    };
+    const downloader = new MatrixMediaDownloader(staleClient as never, createMockLogger());
+
+    downloader.setMatrixClient(freshClient as never);
+
+    await expect(downloader.fetch('mxc://reddit.com/image')).resolves.toEqual({
+      buffer: Buffer.from('fresh-image'),
+      contentType: 'image/jpeg',
+    });
+    expect(staleClient.downloadMedia).not.toHaveBeenCalled();
+    expect(freshClient.downloadMedia).toHaveBeenCalledWith('mxc://reddit.com/image');
+  });
+});

tests/matrix-username-resolver.test.ts

@@ -0,0 +1,50 @@
+import { describe, expect, it, vi } from 'vitest';
+import { MatrixUsernameResolver } from '../src/services/chat/matrix/username-resolver.js';
+
+describe('MatrixUsernameResolver', () => {
+  it('resolves Reddit t2 IDs from authenticated Matrix profile display names', async () => {
+    const getUserProfile = vi.fn(async (mxid: string) => {
+      const profiles: Record<string, { displayname?: string }> = {
+        '@t2_26q364ua7n:reddit.com': { displayname: 'MilkyBabe_10' },
+        '@t2_j8e83d38:reddit.com': { displayname: 'IssueLesss' },
+      };
+      return profiles[mxid] ?? {};
+    });
+    const resolver = new MatrixUsernameResolver({ getUserProfile });
+
+    await expect(
+      resolver.resolveT2Ids(['t2_26q364ua7n', 'j8e83d38']),
+    ).resolves.toEqual({
+      t2_26q364ua7n: 'MilkyBabe_10',
+      t2_j8e83d38: 'IssueLesss',
+    });
+    expect(getUserProfile).toHaveBeenCalledWith('@t2_26q364ua7n:reddit.com');
+    expect(getUserProfile).toHaveBeenCalledWith('@t2_j8e83d38:reddit.com');
+  });
+
+  it('ignores missing and t2-shaped display names without failing the batch', async () => {
+    const getUserProfile = vi.fn(async (mxid: string) => {
+      if (mxid === '@t2_missing:reddit.com') throw new Error('not found');
+      return { displayname: 't2_unresolved' };
+    });
+    const resolver = new MatrixUsernameResolver({ getUserProfile });
+
+    await expect(
+      resolver.resolveT2Ids(['t2_missing', 't2_unresolved']),
+    ).resolves.toEqual({});
+  });
+
+  it('uses replacement Matrix credentials for subsequent profile requests', async () => {
+    const staleClient = { getUserProfile: vi.fn().mockRejectedValue(new Error('expired')) };
+    const freshClient = {
+      getUserProfile: vi.fn().mockResolvedValue({ displayname: 'alice' }),
+    };
+    const resolver = new MatrixUsernameResolver(staleClient);
+
+    resolver.setMatrixClient(freshClient);
+
+    await expect(resolver.resolveT2Ids(['t2_alice'])).resolves.toEqual({ t2_alice: 'alice' });
+    expect(staleClient.getUserProfile).not.toHaveBeenCalled();
+    expect(freshClient.getUserProfile).toHaveBeenCalledWith('@t2_alice:reddit.com');
+  });
+});

tests/reddit-api.test.ts

@@ -1,5 +1,7 @@
 import { describe, it, expect, vi, beforeEach } from 'vitest';
 import axios from 'axios';
+import type { AxiosInstance } from 'axios';
+import type { BrowserContext } from 'playwright';
 import { RedditApiClient } from '../src/reddit/api.js';
 import type { RedditPost } from '../src/reddit/api.js';
 import { createMockLogger } from '../tests/mockLogger.js';
@@ -394,6 +396,44 @@ describe('RedditApiClient', () => {
     });
   });
 
+  describe('resolveUsernameToT2', () => {
+    it('uses the imported Reddit session and normalizes the account ID', async () => {
+      const mockAxios = {
+        get: vi.fn().mockResolvedValue({ data: { data: { id: 'abc123' } } }),
+      };
+      vi.mocked(axios.create).mockReturnValue(mockAxios as unknown as AxiosInstance);
+      const client2 = new RedditApiClient(getTestConfig(), logger);
+      const cookies = vi.fn().mockResolvedValue([
+        { name: 'reddit_session', value: 'session-value' },
+      ]);
+      client2.setBrowserContext({ cookies } as unknown as BrowserContext);
+
+      await expect(client2.resolveUsernameToT2('alice')).resolves.toBe('t2_abc123');
+      expect(mockAxios.get).toHaveBeenCalledWith('/user/alice/about.json', {
+        params: { raw_json: 1 },
+        headers: { Cookie: 'reddit_session=session-value' },
+      });
+    });
+
+    it('returns null only when Reddit confirms the user is missing', async () => {
+      const error = { isAxiosError: true, response: { status: 404 } };
+      const mockAxios = { get: vi.fn().mockRejectedValue(error) };
+      vi.mocked(axios.create).mockReturnValue(mockAxios as unknown as AxiosInstance);
+      const client2 = new RedditApiClient(getTestConfig(), logger);
+
+      await expect(client2.resolveUsernameToT2('missing')).resolves.toBeNull();
+    });
+
+    it('does not misclassify a 403 as an unknown user', async () => {
+      const error = { isAxiosError: true, response: { status: 403 } };
+      const mockAxios = { get: vi.fn().mockRejectedValue(error) };
+      vi.mocked(axios.create).mockReturnValue(mockAxios as unknown as AxiosInstance);
+      const client2 = new RedditApiClient(getTestConfig(), logger);
+
+      await expect(client2.resolveUsernameToT2('alice')).rejects.toBe(error);
+    });
+  });
+
   describe('getNewPosts', () => {
     it('returns empty array for 404 subreddit', async () => {
       const error = { isAxiosError: true, response: { status: 404 } };

tests/repositories.test.ts

@@ -27,6 +27,7 @@ describe('PostsRepository', () => {
       subreddit: 'test',
       author: 'user1',
       title: 'Test Post',
+      postUrl: 'https://www.reddit.com/r/test/comments/post1/test_post/',
       imageUrl: 'http://example.com/img.jpg',
       processedAt: Date.now(),
     });
@@ -37,6 +38,7 @@ describe('PostsRepository', () => {
     expect(post!.subreddit).toBe('test');
     expect(post!.author).toBe('user1');
     expect(post!.title).toBe('Test Post');
+    expect(post!.postUrl).toBe('https://www.reddit.com/r/test/comments/post1/test_post/');
     expect(post!.imageUrl).toBe('http://example.com/img.jpg');
     expect(post!.messageSent).toBe(false);
     expect(post!.imageAnalysis).toBeNull();
@@ -203,7 +205,7 @@ describe('MessagesRepository', () => {
     expect(updated!.gotResponse).toBe(true);
   });
 
-  it('chat-originated rows appear in getRecent and contribute to stats', () => {
+  it('keeps unassociated chat history out of performance trends', () => {
     messagesRepo.insertChat({
       recipient: 'bob',
       subject: 'bob',
@@ -213,6 +215,7 @@ describe('MessagesRepository', () => {
     });
     const recent = messagesRepo.getRecent(10);
     expect(recent.some((m) => m.chatRoomId === '!r1:reddit.com')).toBe(true);
+    expect(messagesRepo.getResponseRateTrend()).toEqual([]);
   });
 
   it('inserts and retrieves a message', () => {
@@ -305,19 +308,22 @@ describe('MessagesRepository', () => {
       subreddit: 'gonewild',
       author: 'alice',
       title: 'Second post',
+      postUrl: 'https://www.reddit.com/r/gonewild/comments/post-b/second_post/',
       imageUrl: null,
       processedAt: Date.now(),
     });
 
     const base = Date.now();
     messagesRepo.insert({ postId: 'post-a', recipient: 'alice', subject: 's', message: 'm', sentAt: base });
-    messagesRepo.insert({ postId: 'post-b', recipient: 'alice', subject: 's', message: 'm', sentAt: base + 1000 });
+    messagesRepo.insert({ postId: 'post-b', recipient: 'alice', subject: 's', message: 'm', sentAt: base + 1000, chatRoomId: 'room-b' });
 
     const latest = messagesRepo.getLatestByRecipient('alice');
     expect(latest).toBeDefined();
     expect(latest!.postId).toBe('post-b');
     expect(latest!.subreddit).toBe('gonewild');
     expect(latest!.postTitle).toBe('Second post');
+    expect(latest!.postUrl).toBe('https://www.reddit.com/r/gonewild/comments/post-b/second_post/');
+    expect(messagesRepo.getByChatRoomId('room-b')).toMatchObject({ postId: 'post-b', postTitle: 'Second post' });
 
     expect(messagesRepo.getLatestByRecipient('ALICE')).toBeDefined();
     expect(messagesRepo.getLatestByRecipient('nobody')).toBeUndefined();

tests/response-checker.test.ts

@@ -161,6 +161,39 @@ describe('ResponseCheckerService', () => {
       expect(messagesRepo.markChecked).toHaveBeenCalled();
     });
 
+    it('does not track an unassociated reply as performance', async () => {
+      const message: SentMessageRecord = {
+        id: 1,
+        postId: null,
+        recipient: 'user1',
+        subject: 'Hello',
+        message: 'Hey!',
+        sentAt: Date.now() - 2 * 3600000,
+        gotResponse: false,
+        responseCheckedAt: null,
+        strategyId: null,
+        chatRoomId: '!room:reddit.com',
+      };
+      messagesRepo = createMockMessagesRepo([message]);
+      checker = new ResponseCheckerService(page, messagesRepo, successfulMessagesRepo, postsRepo, logger);
+      const mockItem = {
+        $: vi.fn(async (selector: string) => selector.includes('author') || selector.includes('sender')
+          ? { textContent: vi.fn(async () => 'user1') }
+          : { textContent: vi.fn(async () => 'Hi there') }),
+        evaluate: vi.fn(async () => true),
+      };
+      vi.mocked(page.$$).mockResolvedValue([mockItem as any]);
+
+      const results = await checker.checkForResponses();
+
+      expect(results).toEqual([
+        expect.objectContaining({ messageId: 1, gotResponse: true }),
+      ]);
+      expect(messagesRepo.markGotResponse).not.toHaveBeenCalled();
+      expect(messagesRepo.markChecked).toHaveBeenCalledWith(1);
+      expect(successfulMessagesRepo.insert).not.toHaveBeenCalled();
+    });
+
     it('stores successful messages for learning', async () => {
       const post: ProcessedPostRecord = {
         id: 'post1',

tests/web/conversations-route.test.ts

@@ -0,0 +1,180 @@
+import express from 'express';
+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';
+
+const servers: Array<ReturnType<express.Express['listen']>> = [];
+
+async function request(app: express.Express, path: string): Promise<Response> {
+  const server = app.listen(0);
+  servers.push(server);
+  await new Promise<void>((resolve) => server.once('listening', resolve));
+  const { port } = server.address() as AddressInfo;
+  return fetch(`http://127.0.0.1:${port}${path}`);
+}
+
+afterEach(async () => {
+  await Promise.all(servers.splice(0).map((server) => new Promise<void>((resolve) => server.close(() => resolve()))));
+});
+
+describe('conversations route', () => {
+  it('reports an unavailable chat service instead of presenting it as an empty inbox', async () => {
+    const context = {
+      logger: { error: vi.fn() },
+      services: {},
+    } as unknown as WebContext;
+    const app = express().use('/api', createConversationsRouter(context));
+
+    const response = await request(app, '/api/conversations');
+
+    expect(response.status).toBe(503);
+    expect(await response.json()).toEqual({ error: 'Chat service not initialized' });
+  });
+
+  it('reports a cache read failure instead of presenting it as an empty inbox', async () => {
+    const logger = { error: vi.fn() };
+    const context = {
+      logger,
+      services: {
+        chat: {
+          getCachedConversations: vi.fn().mockRejectedValue(new Error('cache unavailable')),
+        },
+      },
+    } as unknown as WebContext;
+    const app = express().use('/api', createConversationsRouter(context));
+
+    const response = await request(app, '/api/conversations');
+
+    expect(response.status).toBe(500);
+    expect(await response.json()).toEqual({ error: 'Failed to fetch conversations' });
+    expect(logger.error).toHaveBeenCalledWith('Failed to fetch conversations:', expect.any(Error));
+  });
+
+  it('marks conversations that have received images in the durable media index', async () => {
+    const conversation = {
+      username: 'alice',
+      roomName: 'alice',
+      roomId: 'room-alice',
+      lastMessageTime: 1_786_000_000_000,
+      lastMessageSnippet: '[Image]',
+      isFromUs: false,
+      unread: true,
+    };
+    const context = {
+      logger: { error: vi.fn() },
+      services: {
+        chat: { getCachedConversations: vi.fn().mockResolvedValue([conversation]) },
+        media: {
+          getMediaItems: vi.fn().mockResolvedValue([
+            {
+              id: 'image-one',
+              chatUsername: 'alice',
+              chatRoomId: 'room-alice',
+              sender: 'alice',
+              timestamp: 1_786_000_000_000,
+              originalUrl: 'mxc://reddit.com/image-one',
+              fileName: 'image-one.jpg',
+              relativePath: 'image-one.jpg',
+              createdAt: 1_786_000_000_100,
+            },
+          ]),
+        },
+      },
+    } as unknown as WebContext;
+    const app = express().use('/api', createConversationsRouter(context));
+
+    const legacyResponse = await request(app, '/api/conversations');
+    const response = await request(app, '/api/conversations?includeImageMetadata=true');
+
+    expect(legacyResponse.status).toBe(200);
+    expect(await legacyResponse.json()).toEqual([conversation]);
+    expect(response.status).toBe(200);
+    expect(await response.json()).toEqual([{ ...conversation, hasReceivedImages: true }]);
+  });
+
+  it('serves conversation details without starting a delta sync', async () => {
+    const conversation = {
+      username: 'alice',
+      roomName: 'alice',
+      roomId: 'room-alice',
+      lastMessageTime: 1_786_000_000_000,
+      lastMessageSnippet: 'Hello',
+      isFromUs: false,
+      unread: false,
+      messages: [{
+        sender: 'alice',
+        text: 'Hello',
+        timestamp: 1_786_000_000_000,
+        isSelf: false,
+      }],
+    };
+    const refreshTopChats = vi.fn();
+    const loadConversationDetails = vi.fn();
+    const context = {
+      logger: { error: vi.fn(), warn: vi.fn() },
+      repos: {
+        messages: { getLatestByRecipient: vi.fn().mockReturnValue(undefined) },
+      },
+      services: {
+        chat: {
+          getSyncStatus: vi.fn().mockReturnValue({
+            syncing: false,
+            syncingKind: null,
+            progress: null,
+          }),
+          getCachedConversations: vi.fn().mockResolvedValue([conversation]),
+          refreshTopChats,
+          loadConversationDetails,
+          saveCacheExternal: vi.fn(),
+        },
+      },
+    } as unknown as WebContext;
+    const app = express().use('/api', createConversationsRouter(context));
+
+    const response = await request(app, '/api/conversations/room-alice');
+
+    expect(response.status).toBe(200);
+    expect((await response.json()).username).toBe('alice');
+    expect(refreshTopChats).not.toHaveBeenCalled();
+    expect(loadConversationDetails).not.toHaveBeenCalled();
+  });
+
+  it('attaches the exact room origin with its saved URL, title, and image', async () => {
+    const conversation = {
+      username: 'alice', roomName: 'alice', roomId: 'room-alice',
+      lastMessageTime: 10, lastMessageSnippet: 'Hello', isFromUs: true, unread: false,
+      messages: [{ sender: 'me', text: 'Hello', timestamp: 10, isSelf: true }],
+    };
+    const roomOrigin = {
+      id: 7, postId: 'post-exact', recipient: 'alice', subject: 'alice', message: 'Hello',
+      sentAt: 9, gotResponse: false, responseCheckedAt: null, strategyId: null,
+      chatRoomId: 'room-alice', subreddit: 'example', postTitle: 'Exact source post',
+      postUrl: 'https://www.reddit.com/r/example/comments/post-exact/exact_source_post/',
+      postImageUrl: 'https://i.redd.it/exact-source.jpg',
+    };
+    const latestRecipientOrigin = { ...roomOrigin, postId: 'wrong-latest-post', postTitle: 'Wrong post' };
+    const context = {
+      logger: { error: vi.fn(), warn: vi.fn() },
+      repos: { messages: {
+        getByChatRoomId: vi.fn().mockReturnValue(roomOrigin),
+        getLatestByRecipient: vi.fn().mockReturnValue(latestRecipientOrigin),
+      } },
+      services: { chat: {
+        getSyncStatus: vi.fn().mockReturnValue({ syncing: false, syncingKind: null, progress: null }),
+        getCachedConversations: vi.fn().mockResolvedValue([conversation]),
+        loadConversationDetails: vi.fn(), saveCacheExternal: vi.fn(),
+      } },
+    } as unknown as WebContext;
+    const app = express().use('/api', createConversationsRouter(context));
+
+    const response = await request(app, '/api/conversations/room-alice');
+
+    expect(response.status).toBe(200);
+    expect((await response.json()).triggeringPost).toEqual({
+      id: 'post-exact', subreddit: 'example', title: 'Exact source post',
+      url: roomOrigin.postUrl, imageUrl: roomOrigin.postImageUrl, sentAt: 9,
+    });
+    expect(context.repos.messages.getLatestByRecipient).not.toHaveBeenCalled();
+  });
+});

tests/web/media-route.test.ts

@@ -0,0 +1,66 @@
+import express from 'express';
+import type { AddressInfo } from 'node:net';
+import { afterEach, describe, expect, it, vi } from 'vitest';
+import type { WebContext } from '../../src/web/context.js';
+import { createMediaRouter } from '../../src/web/routes/media.js';
+
+const servers: Array<ReturnType<express.Express['listen']>> = [];
+
+async function request(app: express.Express, path: string): Promise<Response> {
+  const server = app.listen(0);
+  servers.push(server);
+  await new Promise<void>((resolve) => server.once('listening', resolve));
+  const { port } = server.address() as AddressInfo;
+  return fetch(`http://127.0.0.1:${port}${path}`);
+}
+
+afterEach(async () => {
+  await Promise.all(servers.splice(0).map((server) => new Promise<void>((resolve) => server.close(() => resolve()))));
+});
+
+describe('media route username presentation', () => {
+  it('upgrades historical t2 fields through the chat username map', async () => {
+    const context = {
+      logger: { error: vi.fn() },
+      services: {
+        media: { getMediaItems: vi.fn().mockResolvedValue([{
+          id: 'one', chatUsername: 't2_known', chatRoomId: 'room-one', sender: 't2_known',
+          timestamp: 1, originalUrl: 'mxc://one', fileName: 'one.jpg', relativePath: 'one.jpg', createdAt: 2,
+        }]) },
+        chat: {
+          getCachedConversations: vi.fn().mockResolvedValue([]),
+          resolveSenderDisplay: vi.fn((identity: string) => identity === 't2_known' ? 'alice' : identity),
+        },
+      },
+    } as unknown as WebContext;
+    const app = express().use('/api', createMediaRouter(context));
+
+    const response = await request(app, '/api/media');
+
+    expect(response.status).toBe(200);
+    expect(await response.json()).toEqual([expect.objectContaining({ chatUsername: 'alice', sender: 'alice' })]);
+  });
+
+  it('uses a safe fallback when no username mapping exists', async () => {
+    const context = {
+      logger: { error: vi.fn() },
+      services: {
+        media: { getMediaItems: vi.fn().mockResolvedValue([{
+          id: 'one', chatUsername: 't2_missing', chatRoomId: 'room-one', sender: '@t2_missing:reddit.com',
+          timestamp: 1, originalUrl: 'mxc://one', fileName: 'one.jpg', relativePath: 'one.jpg', createdAt: 2,
+        }]) },
+        chat: {
+          getCachedConversations: vi.fn().mockResolvedValue([]),
+          resolveSenderDisplay: vi.fn((identity: string) => identity),
+        },
+      },
+    } as unknown as WebContext;
+    const app = express().use('/api', createMediaRouter(context));
+
+    const response = await request(app, '/api/media');
+    const body = await response.json();
+
+    expect(JSON.stringify(body)).not.toContain('t2_missing');
+    expect(body[0]).toMatchObject({ chatUsername: null, sender: 'Unknown Reddit user' });
+  });
+});

tests/web/reddit-identities.test.ts

@@ -0,0 +1,41 @@
+import { describe, expect, it } from 'vitest';
+import { presentActivityItem, resolveRedditUsername } from '../../src/web/reddit-identities.js';
+
+const resolver = {
+  resolveSenderDisplay(identity: string) {
+    return identity.replace(/^@?t2_known(?::reddit\.com)?$/, 'alice');
+  },
+};
+
+describe('Reddit identity presentation', () => {
+  it('resolves internal ids and rejects unresolved ids', () => {
+    expect(resolveRedditUsername('@t2_known:reddit.com', resolver)).toBe('alice');
+    expect(resolveRedditUsername('t2_missing', resolver)).toBeNull();
+  });
+
+  it('upgrades both the activity recipient and its persisted message text', () => {
+    expect(presentActivityItem({
+      timestamp: 1,
+      type: 'response',
+      message: 'Reply from u/t2_known',
+      recipient: 't2_known',
+    }, resolver)).toEqual({
+      timestamp: 1,
+      type: 'response',
+      message: 'Reply from u/alice',
+      recipient: 'alice',
+    });
+  });
+
+  it('redacts unresolved ids instead of exposing them', () => {
+    const item = presentActivityItem({
+      timestamp: 1,
+      type: 'response',
+      message: 'Reply from @t2_missing:reddit.com',
+      recipient: 't2_missing',
+    }, resolver);
+
+    expect(item.message).toBe('Reply from Reddit user');
+    expect(item.recipient).toBeUndefined();
+  });
+});