Bump to v2026.9.4

Co-Authored-By: Claude Sonnet 5 <noreply@anthropic.com>

.claude/launch.json

@@ -1,17 +0,0 @@
-{
-  "version": "0.0.1",
-  "configurations": [
-    {
-      "name": "frontend",
-      "runtimeExecutable": "npm",
-      "runtimeArgs": ["--prefix", "frontend", "run", "dev"],
-      "port": 5173
-    },
-    {
-      "name": "frontend-preview",
-      "runtimeExecutable": "npm",
-      "runtimeArgs": ["--prefix", "frontend", "run", "preview"],
-      "port": 4173
-    }
-  ]
-}

.gitignore

@@ -17,6 +17,7 @@ dist-ssr/
 ## Editors / OS
 .vscode/
 .idea/
+.claude/
 .DS_Store
 
 ## Test / coverage

ARCHITECTURE.md

@@ -28,7 +28,7 @@ database and Redis; the other runs the application and serves the frontend.
 | Frontend | React + Vite, vite-plugin-pwa | Generates the manifest and service worker for install + push |
 | Reverse proxy / TLS | External Nginx Proxy Manager (pre-existing infra, not deployed by this project) | Terminates TLS, forwards REST + WebSocket traffic to the app server's one port. The app itself serves the built static frontend directly — no separate static-asset server needed |
 | Process management | systemd | No Docker — native to the target Linux distro, no extra install |
-| Auth | Session cookies (httpOnly, secure) | Simplest to carry through a WebSocket handshake automatically |
+| Auth | Session cookies (httpOnly, secure), backed by a server-side session table | Cookie carries only an opaque session id — simplest way to carry auth through a WebSocket handshake automatically, while still allowing server-side revocation (see §4/§10) |
 
 ## 3. System architecture
 
@@ -85,17 +85,31 @@ users
   id, username, email, password_hash, is_bot, is_site_admin, created_at
 
 rooms
-  id, name, description, is_private, owner_id, created_at
+  id, name, description, is_private, is_dm, is_archived, owner_id, created_at
 
 room_memberships
-  room_id, user_id, role (owner | admin | member), joined_at
+  room_id, user_id, role (owner | admin | member), joined_at, last_read_at,
+  hidden_at (DM-only: hides it from one participant's sidebar),
+  email_notifications (opt-in, non-DM rooms only)
 
 room_invites
   id, room_id, invited_by, token, target_user_id or target_email,
   expires_at, status (pending | accepted | revoked)
 
 messages
-  id, room_id, user_id, content, created_at, edited_at, deleted_at
+  id, room_id, user_id, content, image_id, file_id, created_at, edited_at,
+  deleted_at
+
+message_reactions
+  id, message_id, user_id, emoji (unicode glyph or a custom emoji's
+  `:shortcode:`)
+
+custom_emoji
+  id, shortcode (unique, site-wide), storage_filename, content_type,
+  uploaded_by, created_at
+
+sessions
+  id, user_id, ip_address, user_agent, created_at, last_seen_at, revoked_at
 
 push_subscriptions
   id, user_id, endpoint, p256dh_key, auth_key, created_at
@@ -114,6 +128,13 @@ admin_audit_log
   id, actor_id, action, target_type, target_id, metadata, created_at
 ```
 
+Not shown above (present in the implementation, omitted here for brevity):
+`message_images`, `message_files`, `message_mentions`,
+`message_room_references`, `link_previews`, `custom_themes`,
+`upload_settings`, `smtp_settings`, `site_invites`, `password_resets` — see
+`backend/README.md` for the full, current model list and per-feature
+detail on all of these.
+
 ## 5. Permission model
 
 - **Room visibility**: `open` (any authenticated user can find and join) or
@@ -133,7 +154,13 @@ admin_audit_log
 4. Every app instance subscribed to that channel forwards it to its own connected
    members over WebSocket.
 5. For members with no active connection, the server looks up
-   `push_subscriptions` and sends a Web Push notification via `pywebpush`.
+   `push_subscriptions` and sends a Web Push notification via `pywebpush`,
+   and a native desktop notification over the socket if the client is DS
+   Chat Desktop.
+6. Separately, a genuinely-offline DM recipient always gets an email; a
+   regular room's member gets one too if they've opted in for that room
+   (first unread message, or any `@mention` regardless of debounce) — see
+   `backend/README.md`'s "Email notifications for missed messages".
 
 ## 7. Extension system: bots and AI agents
 

CONTRIBUTING.md

@@ -0,0 +1,51 @@
+# Contributing to DS Chat
+
+Thanks for considering a contribution.
+
+## Reporting bugs and requesting features
+
+Open an issue on this project's issue tracker. Include steps to reproduce
+for a bug, or the problem you're trying to solve for a feature request —
+that's usually more useful than a proposed solution.
+
+## Development setup
+
+See the root [README.md](README.md)'s Quickstart, plus
+[backend/README.md](backend/README.md) and
+[frontend/README.md](frontend/README.md) for the full local dev setup
+(Postgres, Redis, Python venv, migrations, the Vite dev server).
+[ARCHITECTURE.md](ARCHITECTURE.md) covers the overall system design if
+you're orienting yourself before a larger change.
+
+## Before opening a pull request
+
+- **Tests**: run `pytest` in `backend/` for any backend change, and add
+  tests for new behavior rather than just the happy path — see
+  `backend/README.md`'s "Run tests" section. For frontend changes, run
+  `npx tsc -b` in `frontend/` and confirm `npm run build` succeeds.
+- **Style**: match the conventions already in the file you're editing
+  rather than introducing a new pattern — this codebase doesn't have a
+  separate style guide beyond "look at what's already there."
+- **Scope**: smaller, focused PRs are easier to review than large ones
+  that mix unrelated changes.
+
+## Contributor terms
+
+By submitting a contribution (a pull request, patch, or similar), you
+agree that:
+
+1. Your contribution is licensed under the project's own license,
+   AGPL-3.0-or-later ([LICENSE](LICENSE)), and
+2. You grant the project's maintainer(s) a perpetual, worldwide,
+   non-exclusive right to also relicense your contribution under different
+   terms — for example, as part of a separately-licensed commercial
+   offering built on this project.
+
+This keeps the option of a future dual-licensed (open-source +
+commercial) version of the project available, without requiring a
+separate signed agreement for every contribution.
+
+*This is a lightweight starting point, not a substitute for legal advice —
+if you're contributing something substantial, or maintaining a fork with
+your own commercial plans, it's worth having this reviewed by a lawyer
+rather than relying on the paragraph above alone.*

DEPLOYMENT.md

@@ -132,35 +132,45 @@ sudo -u ds-chat ssh-keygen -t ed25519 -f /srv/ds-chat/.ssh/id_ed25519 -N ""
 sudo cat /srv/ds-chat/.ssh/id_ed25519.pub
 ```
 
-Add that public key as a **read-only deploy key** on the Gitea repo
+This project is hosted at
-(Settings → Deploy Keys), then:
+**[github.com/ds-ksmith/DS-Chat](https://github.com/ds-ksmith/DS-Chat)**.
+Add that public key there as a **read-only deploy key** (Settings → Deploy
+Keys on the repo), then:
 
 ```bash
-sudo -u ds-chat ssh-keyscan git.darksingularity.org >> /srv/ds-chat/.ssh/known_hosts
+sudo -u ds-chat ssh-keyscan github.com >> /srv/ds-chat/.ssh/known_hosts
-sudo -u ds-chat git clone git@git.darksingularity.org:DarkSingularity/ds-chat.git /srv/ds-chat
+sudo -u ds-chat git clone git@github.com:ds-ksmith/DS-Chat.git /srv/ds-chat
 ```
 
-(If your Gitea's SSH is on a non-default port, adjust the clone URL and
+(Deploying from your own fork instead? Substitute its clone URL — the same
-`ssh-keyscan -p <port>` accordingly.)
+deploy-key/access-token steps work the same way on GitHub, GitLab, Gitea,
+and most other git hosts.)
 
 **Alternative: a personal/deployment-user access token instead of a deploy
 key** — skip the `.ssh`/`ssh-keygen`/`ssh-keyscan` commands above entirely
 and clone over HTTPS with the token embedded in the URL:
 
 ```bash
-sudo -u ds-chat git clone https://<TOKEN>@git.darksingularity.org/DarkSingularity/ds-chat.git /srv/ds-chat
+sudo -u ds-chat git clone https://<TOKEN>@github.com/ds-ksmith/DS-Chat.git /srv/ds-chat
 ```
 
 The token then lives in plaintext in `/srv/ds-chat/.git/config` (`git
 remote -v` shows it) — readable by root and the `ds-chat` user, not by
 anyone else under normal file permissions. `deploy/upgrade.sh`'s later
-`git pull`s reuse this same authenticated URL automatically, no extra
+`git fetch`es reuse this same authenticated URL automatically, no extra
 setup needed. Fine as long as the token is scoped to read-only access on
 just this repo.
 
-Either way, now that the repo is cloned:
+Either way, now that the repo is cloned, check out the latest release tag
+rather than deploying whatever the default branch's tip happens to be —
+`deploy/upgrade.sh` follows the same rule on every later upgrade (see §6),
+so this keeps the very first deploy consistent with all the ones after it:
 
 ```bash
+cd /srv/ds-chat
+sudo -u ds-chat git fetch --tags
+LATEST_TAG="$(sudo -u ds-chat git tag --sort=-creatordate | head -n1)"
+sudo -u ds-chat git checkout --detach "$LATEST_TAG"
 sudo -u ds-chat mkdir -p /srv/ds-chat/uploads
 ```
 
@@ -232,7 +242,16 @@ admin sets it up.
 `/ws`) whenever that directory exists — that's what lets Nginx Proxy
 Manager forward the whole domain to one port with no custom path routing.
 
+Before building, copy `frontend/.env.example` to `frontend/.env.production`
+and set `VITE_SOURCE_URL` to wherever *your* copy of the repo lives — see
+that file's own comment for why this matters (AGPL-3.0 source-availability
+compliance). Vite bakes this in at build time, so it needs to be in place
+before `npm run build` runs, and needs re-running after any future change
+to it.
+
 ```bash
+sudo -u ds-chat cp /srv/ds-chat/frontend/.env.example /srv/ds-chat/frontend/.env.production
+sudo -u ds-chat nano /srv/ds-chat/frontend/.env.production  # set VITE_SOURCE_URL
 sudo -u ds-chat bash -c 'cd /srv/ds-chat/frontend && npm ci && npm run build'
 ```
 
@@ -320,12 +339,15 @@ This is config in NPM's own UI/database, not a file this repo ships:
 sudo -u ds-chat /srv/ds-chat/deploy/upgrade.sh
 ```
 
-Pulls latest `main`, reinstalls backend deps, runs `alembic upgrade head`,
+Fetches tags and checks out whichever one sorts newest (`git tag
-rebuilds the frontend, restarts `ds-chat`, and curls `/api/health` to
+--sort=-creatordate`) — deliberately not the default branch's tip, so
-confirm it came back up. Fails loudly (`set -euo pipefail`) and stops
+running this between releases is a safe no-op rather than pulling in
-before restarting anything if an earlier step — most importantly a failed
+whatever's mid-flight on `main`. Then reinstalls backend deps, runs
-migration — errors out, so a bad deploy doesn't take down the previously
+`alembic upgrade head`, rebuilds the frontend, restarts `ds-chat`, and
-working one.
+curls `/api/health` to confirm it came back up. Fails loudly
+(`set -euo pipefail`) and stops before restarting anything if an earlier
+step — most importantly a failed migration — errors out, so a bad deploy
+doesn't take down the previously working one.
 
 Active users get disconnected for a few seconds during the restart and
 reconnect automatically (same reconnect logic as §4's NPM-timeout note) —
@@ -345,11 +367,12 @@ producing a gzipped `pg_dump` in `/var/backups/ds-chat/` with 14-day local
 rotation. Off-box shipping is a placeholder in that script (commented-out
 rsync/S3 examples) — decide where those need to go and fill it in.
 
-That script covers Postgres only. Uploaded chat images and file attachments
+That script covers Postgres only. Uploaded chat images, file/video
-both live on the **app** server's disk (`/srv/ds-chat/uploads`, created in
+attachments, avatars, and custom emoji all live on the **app** server's
-§3a) — a separate machine from the data server this script runs on — and
+disk (`/srv/ds-chat/uploads`, created in §3a) — a separate machine from
-currently have no backup mechanism at all. Whatever off-box destination you
+the data server this script runs on — and currently have no backup
-pick above, include `/srv/ds-chat/uploads` in it too (e.g. a second `rsync`
+mechanism at all. Whatever off-box destination you pick above, include
+`/srv/ds-chat/uploads` in it too (e.g. a second `rsync`
 line run from the app server).
 
 **Test a restore** (against a scratch database, never directly onto
@@ -389,13 +412,13 @@ Carried forward from earlier phases (see `backend/README.md`'s own "Notes /
 scope decisions" for the full detail on each):
 - No rate limiting on human or bot API traffic.
 - No CSRF token (relies on `SameSite=Lax` cookies).
-- No server-side session revocation (signed cookies only).
 - SSRF protection on outgoing webhooks is creation-time only, not
   re-validated per delivery (DNS-rebinding gap).
 - Backup off-box shipping is a placeholder — decide a destination and fill
   in `deploy/backup-postgres.sh`.
-- Uploaded chat images and file attachments (`/srv/ds-chat/uploads` on the
+- Uploaded chat images, file/video attachments, and custom emoji
-  app server) have no backup coverage at all yet, on-box or off — see §7.
+  (`/srv/ds-chat/uploads` on the app server) have no backup coverage at
+  all yet, on-box or off — see §7.
 - Uploaded-but-never-sent images or files (a user attaches one, then never
   hits Send) leak an orphaned file on disk — no cleanup job for this yet.
   Not a security issue (still gated by room membership to view), just an

LICENSE

@@ -629,8 +629,8 @@ to attach them to the start of each source file to most effectively
 state the exclusion of warranty; and each file should have at least
 the "copyright" line and a pointer to where the full notice is found.
 
-    <one line to give the program's name and a brief idea of what it does.>
+    DS Chat, a self-hosted, real-time team chat service.
-    Copyright (C) <year>  <name of author>
+    Copyright (C) 2026  Keith Smith
 
     This program is free software: you can redistribute it and/or modify
     it under the terms of the GNU Affero General Public License as published by

README.md

@@ -18,21 +18,26 @@ build plan.
 
 ## Features
 
-- **Auth & accounts** — session-based auth, invite-only signup (admin-issued
+- **Auth & accounts** — server-side, revocable sessions (see every device
-  site invites or room invites, both delivered by email), password reset,
+  you're logged in from and sign one out remotely), invite-only signup
-  per-user light/dark/midnight/sunset presets plus a live theme builder for
+  (admin-issued site invites or room invites, both delivered by email),
-  fully custom, named, savable color themes.
+  password reset, per-user light/dark/midnight/sunset presets plus a live
-- **Rooms** — open and private rooms, owner/admin/member roles, invites,
+  theme builder for fully custom, named, savable color themes.
-  room browsing/search, file/image galleries per room.
+- **Rooms & direct messages** — open and private rooms, owner/admin/member
+  roles, invites (with resend), room browsing/search, file/image galleries
+  per room, plus 1:1 direct messages with a collapsible sidebar section.
 - **Real-time chat** — WebSocket-based messaging with automatic reconnect
-  and backoff, Markdown rendering, @mentions with autocomplete and inline
+  and backoff, Markdown rendering (headings with custom anchors, sub/
-  highlighting, emoji reactions, message editing, image and file
+  superscript, tables, and more), @mentions and #room-reference links with
-  attachments (drag-and-drop, paste, or picker) with inline previews for
+  autocomplete and inline highlighting, emoji reactions and shortcodes plus
-  images/PDFs/text/Markdown, unread indicators, and presence (online/away/
+  site-wide custom/uploaded emoji, message editing and deletion, image/
+  video/file attachments (drag-and-drop, paste, or picker) with inline
+  previews and playback, unread indicators, and presence (online/away/
   offline, with a manual "appear offline" override).
-- **Notifications** — Web Push for offline/backgrounded members, with
+- **Notifications** — Web Push and native desktop notifications for
-  per-type opt-in/out (mentions vs. all messages), plus in-app unread
+  offline/backgrounded members, plus email: always-on for direct messages,
-  badges.
+  opt-in per room (first unread message and every mention), all alongside
+  in-app unread badges.
 - **PWA** — installable, offline-capable (cached room/message data, a
   dedicated offline banner), with automatic update detection that prompts
   a reload as soon as a new deploy goes live.

USER_GUIDE.md

@@ -7,15 +7,17 @@ attachments, notifications, and personalizing your account.
 
 - [Getting started](#getting-started)
 - [Rooms](#rooms)
+- [Direct messages](#direct-messages)
 - [Sending messages](#sending-messages)
 - [Formatting](#formatting)
 - [Mentions and room links](#mentions-and-room-links)
 - [Attachments](#attachments)
-- [Reactions](#reactions)
+- [Reactions and custom emoji](#reactions-and-custom-emoji)
-- [Editing a message](#editing-a-message)
+- [Editing and deleting a message](#editing-and-deleting-a-message)
 - [Presence and notifications](#presence-and-notifications)
 - [Your profile](#your-profile)
 - [Room details](#room-details)
+- [Active sessions](#active-sessions)
 - [Staying up to date](#staying-up-to-date)
 
 ## Getting started
@@ -45,6 +47,21 @@ search box at the top to filter by name.
 - **Unread indicators**: a room with new activity shows a dot next to its
   name — a plain dot for unread messages, a highlighted dot if you were
   specifically @mentioned.
+- **Collapsible sections**: the **Direct Messages** and **Rooms** headers in
+  the sidebar can be collapsed to hide their contents — click the header to
+  toggle. Your choice is remembered.
+
+## Direct messages
+
+Click **People** to see everyone on the site and start a 1:1 conversation
+with someone — it opens (or reopens, if you've messaged them before)
+under **Direct Messages** in the sidebar. There's only ever one
+conversation per pair of people, however many times you start it.
+
+You can hide a conversation you're done with (its own menu, or from its
+**Room details** panel) without deleting anything — it drops out of your
+sidebar but reappears automatically the moment the other person sends a
+new message, or if you message them again yourself.
 
 ## Sending messages
 
@@ -61,7 +78,9 @@ Messages support Markdown:
 - `-` or `1.` for bulleted/numbered lists
 - `[link text](https://example.com)` — or just paste a bare URL and it
   becomes clickable automatically
-- `#`, `##`, `###` for headings
+- `#`, `##`, `###` for headings — add `{#custom-id}` at the end of a
+  heading line to control its link anchor instead of the auto-generated one
+- `~sub~` and `^sup^` for subscript and superscript
 
 Pasting a link on its own often also generates a preview card underneath
 your message, pulled from that page's title/description/image, when the
@@ -69,7 +88,9 @@ page provides one.
 
 Emoji: click the 🙂 button in the composer to open the emoji picker, or
 type a shortcode like `:tada:` and it's converted automatically once you
-send. The picker remembers your recently-used emoji and has a search box.
+send. The picker remembers your recently-used emoji and has a search box —
+see [Reactions and custom emoji](#reactions-and-custom-emoji) for uploading
+your own.
 
 ## Mentions and room links
 
@@ -87,26 +108,39 @@ can see the message (and is a member of that room) straight to it.
 
 Click the paperclip icon to attach a file, or just drag a file onto the
 message box and drop it. Images show as an inline thumbnail — click one
-to view it full-size. Other files show as a small card with the
+to view it full-size. Common video formats (MP4, WebM, Ogg) play inline
-filename and size; `.txt`, `.md`, and `.pdf` files open in a preview
+too, with a button to expand to a larger view; other files show as a
-without leaving the room, everything else downloads when clicked.
+small card with the filename and size — `.txt`, `.md`, and `.pdf` files
+open in a preview without leaving the room, everything else downloads
+when clicked.
 
 There's a server-configured maximum file size — if a file is too large,
 you'll see an error before it uploads.
 
-## Reactions
+## Reactions and custom emoji
 
 Hover over a message and click the 🙂 icon in its action row to react
 with an emoji. Reactions from everyone appear as small pills under the
 message with a count; click an existing pill to add or remove your own
 reaction to it. Hovering a pill shows who reacted.
 
-## Editing a message
+Anyone can add a custom emoji: open the emoji picker (the 🙂 button, either
+in the composer or on a message) and click **+ Add** in the **Custom**
+section. Give it a short name and an image — it's then usable by everyone,
+both as a reaction and inline in message text via `:your-name:`, right
+alongside the built-in picker. You can remove a custom emoji you uploaded
+(or any of them, if you're a site admin) from the same picker.
+
+## Editing and deleting a message
 
 You can edit any message you sent: hover it and click **Edit**, make your
 changes, then press **Enter** to save or **Escape** to cancel. Clicking
 away also saves. Edited messages are marked *(edited)*.
 
+To delete a message you sent, hover it and click **Delete**. It's replaced
+with a "message deleted" placeholder rather than disappearing outright, so
+the conversation doesn't visibly shift for anyone else reading it.
+
 ## Presence and notifications
 
 Everyone's avatar shows a small status dot — green for online, grey for
@@ -124,6 +158,12 @@ The same menu has a notifications toggle:
   get a notification whenever the app is minimized *or* simply not the
   focused window, even if it's still open somewhere on screen.
 
+You'll also get an email if someone messages you in a direct conversation
+while you're genuinely offline — no setup needed. For regular rooms,
+email is opt-in per room: open a room's **Room details** panel and turn
+on **Email notifications** to get emailed on that room's first unread
+message and on every `@mention`, while you're offline.
+
 ## Your profile
 
 Open your account menu and choose **Profile settings** to:
@@ -135,12 +175,22 @@ Open your account menu and choose **Profile settings** to:
   live)
 - Change your password
 
+## Active sessions
+
+Profile settings also lists **Active sessions** — every device/browser
+currently logged into your account, with its approximate location (IP
+address) and when it was last active. If you see one you don't
+recognize, click **Revoke** to sign it out immediately. Revoking your own
+current device signs you out too.
+
 ## Room details
 
 Click the info icon in a room's header to open its details panel, where
 you can:
 
 - See who else is in the room and their role (member/admin/owner)
+- Turn on **Email notifications** for that room (see
+  [Presence and notifications](#presence-and-notifications))
 - Browse and re-download every file and image ever shared in the room,
   without scrolling back through history
 - Leave the room — unless you're the owner, in which case ownership has

backend/README.md

@@ -1,18 +1,22 @@
-# DS Chat backend (Phase 1 + 2 + 4 + 5 + 6 + 7 + 8, image uploads, file attachments, admin-configurable upload size limits, emoji & reactions, user profiles, site invites & email, password reset)
+# DS Chat backend (Phase 1 + 2 + 4 + 5 + 6 + 7 + 8, image uploads, file attachments, admin-configurable upload size limits, emoji & reactions, user profiles, site invites & email, password reset, direct messages, active sessions)
 
-FastAPI + SQLAlchemy 2.0 (async) + PostgreSQL + Redis. Implements auth, room
+FastAPI + SQLAlchemy 2.0 (async) + PostgreSQL + Redis. Implements auth
-CRUD (open and private), room roles (owner/admin/member) and direct
+(server-side, revocable sessions — see Active sessions below), room CRUD
-membership management, a WebSocket chat endpoint that fans out across
+(open and private), room roles (owner/admin/member) and direct membership
-multiple app-server instances via Redis pub/sub, Web Push notifications for
+management, direct messages, a WebSocket chat endpoint that fans out across
-offline room members, a site-admin portal (user/room/bot management + an
+multiple app-server instances via Redis pub/sub, Web Push and email
-audit log), a bot/extension layer (scoped API tokens, live bot WebSocket
+notifications for offline room members (plus a native desktop-notification
-access, incoming and outgoing webhooks, message editing), image uploads and
+bridge for DS Chat Desktop), a site-admin portal (user/room/bot management +
-generic file attachments in chat messages, emoji reactions on messages,
+an audit log), a bot/extension layer (scoped API tokens, live bot WebSocket
-self-service user profiles
+access, incoming and outgoing webhooks, message editing), image uploads,
-(display name, avatar), self-service password change and a token-based
+inline-playable video attachments, and generic file attachments in chat
-forgot-password flow, and admin-issued email invites for new accounts
+messages, message deletion, emoji reactions (built-in Unicode plus
-plus email notifications when a user is added to a room. See
+site-wide custom/uploaded emoji, both usable in reactions and inline in
-`../ARCHITECTURE.md` for the full system design and the phased build plan.
+message text), self-service user profiles (display name, avatar),
+self-service password change and a token-based forgot-password flow, and
+admin-issued email invites for new accounts plus email notifications when a
+user is added to a room. See `../ARCHITECTURE.md` for the full system
+design and the phased build plan.
 
 This is an **invite-only site**: there is no public registration endpoint.
 Accounts are created by an operator on the app server — see step 4 below.
@@ -129,10 +133,14 @@ app/
                              on-disk save/read -- see Image uploads below
   cli.py                  `python -m app.cli create-user` / `generate-vapid-keys`
   models/                 SQLAlchemy models (users, rooms, room_memberships,
-                             messages, message_images, message_reactions,
+                             messages, message_images, message_files,
+                             message_reactions, message_mentions,
+                             message_room_references, link_previews,
+                             custom_emoji, custom_themes, sessions,
                              site_invites, password_resets, smtp_settings,
-                             push_subscriptions, admin_audit_log, api_tokens,
+                             upload_settings, push_subscriptions,
-                             webhooks_incoming, event_subscriptions)
+                             admin_audit_log, api_tokens, webhooks_incoming,
+                             event_subscriptions)
   schemas/                 Pydantic request/response models
   routers/                  auth, rooms, users, signup, push, admin,
                                bots, webhooks, health
@@ -345,6 +353,36 @@ No `User`/`PushSubscription` schema change was needed for this feature —
 the only backend change is the new `desktop_notification` envelope type,
 covered by `backend/tests/test_desktop_notifications.py`.
 
+## Email notifications for missed messages
+
+Two related, separately-scoped email triggers layered on top of Web Push/
+desktop notifications, both in `app/services/message_events.py`:
+
+**DMs** (`_maybe_email_dm_notification`) — always on, no opt-in toggle.
+Emails a DM's other participant when they're *genuinely* offline
+(`GlobalPresence.is_online`, not just "not connected to this room's own
+channel" the way the Web Push/desktop-notification audience is computed —
+someone actively using the app in a different room shouldn't get emailed
+for a DM) or have `appear_offline` set. Debounced to the first unread
+message in the conversation, not one email per message in a burst, by
+checking whether any other unread message already exists in the room
+since the recipient's `last_read_at`.
+
+**Regular rooms** (`_maybe_email_room_notifications`) — opt-in per
+member, per room (`RoomMembership.email_notifications`, toggled via `PATCH
+/api/rooms/{id}/notifications`; rejected for a DM — `CannotModifyDmError`
+→ 400 — since DMs already get the always-on behavior above). Two triggers,
+not one: the room's first unread message debounces the same way DMs do,
+*but* a message that `@mentions` the subscriber always emails regardless
+of that debounce — a mention is a stronger, individually-addressed signal
+that shouldn't get silently absorbed by an earlier plain message in the
+same burst already having used up the "first unread" email.
+
+Both paths go through the same `email_service.send_email` used by
+invites/room-membership notifications above, so they're silently skipped
+if SMTP isn't configured and never block message delivery on an SMTP
+outage.
+
 ## Room roles and membership (Phase 2)
 
 Rooms can be `open` (anyone can join via `POST /api/rooms/{id}/join`) or
@@ -365,6 +403,47 @@ since nothing meaningful was gained by making the target confirm first.
 `GET /api/rooms/mine` lists every room (open + private) the current user
 belongs to, alongside their role.
 
+## Direct messages
+
+A DM is a `Room` with `is_dm=True` and a deterministic, never-shown
+internal `name` (`dm_room_name(user_a, user_b)` — the two user ids sorted
+and joined, so it's the same string regardless of who initiates), not a
+separate model — `POST /api/rooms/dm` (`find_or_create_dm`) looks up an
+existing DM by that name and creates one (`is_private=True`, both
+participants as plain `member`) only if none exists yet, so starting a DM
+with the same person twice always resolves to the one conversation. The
+frontend never renders `Room.name` for a DM; `MyRoomItem.dm_partner`
+(`DmPartnerInfo`: the *other* participant's id/username/display
+name/avatar/status) is precomputed server-side instead, batched per
+request rather than N+1.
+
+**Hiding a DM**: `RoomMembership.hidden_at` lets one participant remove a
+DM from their own sidebar without touching the other participant's copy or
+deleting anything — a DM has no sensible "leave" (it would violate
+`find_or_create_dm`'s exactly-two-members assumption). `POST
+/api/rooms/{id}/hide` sets it; it's cleared automatically (un-hiding the
+DM) whenever a new message arrives in it or `find_or_create_dm` resolves
+back to an already-hidden one — both count as the conversation being
+active again, matching how a re-opened DM in Slack/Discord reappears on
+its own rather than needing an explicit "unhide."
+
+## Message deletion
+
+`DELETE`-shaped over WS (`{"type": "delete", "room_id", "message_id"}`,
+`message_service.delete_message`) — author-only (`NotMessageAuthorError` →
+error frame otherwise, no admin/moderator override yet). A real delete of
+content, not a UI-only hide: `content`, `image_id`, `file_id`, and
+`preview_url` are all cleared and any attached `MessageImage`/`MessageFile`
+row (plus its on-disk file) is actually removed, only `deleted_at` (and
+`id`/`room_id`/`user_id`/`created_at`, so the tombstone still occupies its
+place in history) survives. The attachment's storage filename is read and
+the DB row/file only unlinked *after* a successful commit — same ordering
+`delete_room` already uses, so a rolled-back transaction never leaves an
+already-destroyed file with no way back. Broadcasts
+`{"type": "message_deleted", "id", "room_id"}`; the frontend renders a
+"message deleted" placeholder rather than removing the row, so the
+conversation doesn't visibly shift when someone deletes something above.
+
 ## Image uploads
 
 A message can carry an image (`Message.image_id`, nullable), a caption
@@ -432,6 +511,18 @@ share them; `ImageTooLargeError` was likewise renamed to
 
 Same orphaned-upload disk-space caveat as images applies here too.
 
+**Inline video playback**: a browser-natively-playable video attachment
+(`INLINE_SAFE_VIDEO_CONTENT_TYPES` in `app/storage.py` — a strict allowlist,
+`video/mp4`/`video/webm`/`video/ogg`, deliberately not "every `video/*`
+type") is served *without* the `filename=` param above, so it plays inline
+in a `<video>` tag instead of forcing a download — the same reasoning
+`MessageImage`'s own always-inline endpoint already relies on: these are
+content types a browser only ever interprets as media, never as something
+that could execute script, so the `Content-Disposition: attachment`
+mitigation doesn't need to apply to them. Anything outside that allowlist
+(e.g. `.mov`/`video/quicktime`) still forces a download like any other
+file.
+
 ## Upload size limits
 
 The 8 MB image/file/avatar cap is no longer hardcoded — it's an
@@ -462,14 +553,17 @@ returning `None`.
 
 ## Emoji & reactions
 
-An emoji picker in the frontend composer is purely client-side (a static
+The built-in emoji picker in the frontend composer is purely client-side (a
-curated unicode list, no backend involvement). Message **reactions** are
+static curated unicode list, no backend involvement). Message **reactions**
-full-stack: `message_reactions` (`app/models/message_reaction.py`) has
+are full-stack: `message_reactions` (`app/models/message_reaction.py`) has
 `message_id`, `user_id`, `emoji`, and a `UniqueConstraint` on all three
 backing toggle semantics — the same user reacting with the same emoji on
 the same message twice removes it (Slack/Mattermost convention).
 `message_service.toggle_reaction` is a plain select-then-delete-or-insert,
-no upsert needed.
+no upsert needed. `emoji` is `String(32)`, sized to hold either a raw
+unicode glyph or a custom emoji's `:shortcode:` reference (see Custom emoji
+below) — the WS reaction envelope's own length check matches this exactly,
+not an arbitrary smaller cap.
 
 WS `"reaction"` envelope (`room_id`, `message_id`, `emoji`) toggles a
 reaction; the server broadcasts the message's **full recomputed** reaction
@@ -482,8 +576,42 @@ reload doesn't lose reaction state that only ever arrived over WS.
 
 Scope cuts: no outgoing-webhook event type for reactions (`VALID_EVENT_TYPES`
 in `webhook_service.py` is unchanged — same restraint as image uploads), no
-reaction-count limit or rate limiting, no custom/uploaded emoji (unicode
+reaction-count limit or rate limiting.
-only, curated client-side list in `frontend/src/lib/emoji.ts`).
+
+## Custom emoji
+
+Site-wide (not room-scoped), uploadable by any authenticated user —
+distinct from the built-in Unicode picker above. `CustomEmoji`
+(`app/models/custom_emoji.py`): `shortcode` (unique, 30 chars max — sized
+so a `:shortcode:` reference fits `MessageReaction.emoji`'s column
+alongside its own colons with zero width change), `storage_filename`,
+`content_type`, `uploaded_by`.
+
+- `POST /api/custom-emoji` (multipart: `shortcode` form field + `file`) —
+  reuses `app/storage.py`'s upload primitives (`read_capped`,
+  `process_image(..., square=True, max_dimension=128)`, `save_file`), same
+  pattern as avatars. Shortcode format (`^[a-z0-9_-]{2,30}$`) and
+  uniqueness are checked *before* processing/saving the image, so a
+  rejected upload never orphans a file on disk.
+- `GET /api/custom-emoji` — full list, any authenticated user.
+- `DELETE /api/custom-emoji/{id}` — the uploader or a site admin only
+  (`NotEmojiOwnerError` → 403 otherwise).
+- `GET /api/custom-emoji/{shortcode}/image` — serves the file,
+  `Cache-Control: private, no-cache` (not `immutable`, and deliberately
+  *not* a long `max-age` either — a shortcode can be deleted and
+  re-uploaded with different image data under the same URL, and a timed
+  cache let a browser keep serving the old image for its full duration
+  after that happened; `no-cache` forces revalidation on every use, still
+  cheap since `FileResponse`'s own `ETag`/`Last-Modified` make an
+  unchanged file a 304, not a full re-transfer).
+
+A `:shortcode:` reference is stored/sent as literal text everywhere (message
+content, reaction values) and resolved to an image only at render time on
+the frontend — the same convention the built-in Unicode shortcode
+autocomplete already used for glyphs, extended to a case with no unicode
+codepoint to substitute. No server-side collision check against the ~950
+built-in shortcode names (that list only exists in the frontend); the
+upload UI warns about a colliding name but doesn't hard-block it.
 
 ## User profiles
 
@@ -530,15 +658,21 @@ the Admin portal; being added directly to a room (see Room roles and
 membership above) sends a "you've been added" email too.
 
 **Email sending** (`app/services/email_service.py`, using `aiosmtplib`):
-`send_email(db, to, subject, body)` is the fire-and-forget path used by
+`send_email(db, to, subject, paragraphs, *, cta_label=None, cta_url=None,
-invite flows — if `SmtpSettings` isn't configured yet it logs at debug and
+theme_user=None)` is the fire-and-forget path used by invite/notification
-returns (same "silently skip if unconfigured" UX push notifications already
+flows — if `SmtpSettings` isn't configured yet it logs (at `.warning`, not
-use for a missing VAPID key), and it never raises on delivery failure (an
+`.debug` — this app has no logging config lowering the root level below
-SMTP outage must not block an invite/membership action that already
+Python's own `WARNING` default, so anything below that is silently
-succeeded in the database). `send_test_email(db, to)` is the one exception —
+invisible in production) and returns, and it never raises on delivery
-used only by the admin "send test email" button, it raises so the UI can
+failure (an SMTP outage must not block an invite/membership/notification
-show *why* it failed instead of a silent no-op. Plain-text bodies only, no
+action that already succeeded in the database). `send_test_email(db, to)`
-HTML templates, matching this codebase's existing minimalism.
+is the one exception — used only by the admin "send test email" button, it
+raises so the UI can show *why* it failed instead of a silent no-op.
+`paragraphs` (a `list[str]`, not a flat `body: str`) renders both an HTML
+email — styled with `theme_user`'s own selected theme palette when given,
+falling back to the default palette — and a plain-text fallback part from
+the same source, rather than a single pre-formatted string that can't
+cleanly become HTML without re-parsing it.
 
 **SMTP configuration** (`app/models/smtp_settings.py`, `app/routers/admin.py`'s
 `/settings/smtp` endpoints) lives in the database, not the env file — the
@@ -558,19 +692,25 @@ tokens use — it's a bearer secret looked up by itself). `POST /api/signup`
 (`app/routers/signup.py`) is the first genuinely public,
 unauthenticated endpoint in this app that creates a `User` row — it calls
 the existing `auth_service.register_user` directly for identical
-hashing/uniqueness handling, and logs the new user in immediately (same
+hashing/uniqueness handling, then `session_service.start_session` (see
-session-cookie line `auth.py`'s `login()` uses) so they land in the app
+Active sessions below) so they land in the app already signed in. No new
-already signed in. No new rate limiting on it — the unguessable, single-use,
+rate limiting on it — the unguessable, single-use, expiring token is the
-expiring token is the actual protection, inheriting the same "no rate
+actual protection, inheriting the same "no rate limiting on human/bot
-limiting on human/bot traffic" gap already documented below, not a new one.
+traffic" gap already documented below, not a new one.
+
+`POST /api/admin/invites/{id}/resend` (site-admin only,
+`resend_site_invite`) issues a fresh token and resets the 7-day expiry
+rather than re-sending the original link — the old link stops working the
+moment this runs, and it means resending something close to expiring buys
+the full week again, not just whatever was left. Only valid for a still-
+`pending` invite (`SiteInviteNotPendingError` otherwise).
 
 **Room-membership email**: `room_service.add_member` sends one email to
 the target user after creating the `RoomMembership`, using the live
 request's `base_url` for the link — no new "public URL" config needed.
 
 Scope cuts: no outgoing-webhook event type for these (matching image
-uploads/reactions), no resend for a site invite (revoke + re-invite covers
+uploads/reactions).
-it), no HTML email templates.
 
 ## Self-service password change and reset
 
@@ -581,10 +721,11 @@ password, and a "forgot password" flow for someone locked out.
 `current_password` + `new_password`; verifies the current one with
 `security.verify_password` before setting `password_hash =
 hash_password(new_password)`. Same self-service shape as `PATCH /api/auth/me`
-(profile update): mutate `current_user`, commit, done. No session
+(profile update): mutate `current_user`, commit, done. Doesn't proactively
-invalidation elsewhere (there's no server-side session table to invalidate
+revoke any other logged-in session for that account — a session table now
-against — see Notes below), so other logged-in sessions for that account
+exists (see Active sessions below), but changing your password doesn't
-stay valid until they expire naturally.
+walk it and revoke everything else; if you suspect a specific device, use
+Active sessions to revoke it directly instead.
 
 **Forgot password** (`app/models/password_reset.py`,
 `app/services/password_service.py`) — same hashed-token-with-expiry shape as
@@ -597,8 +738,8 @@ registered, so a miss is a silent no-op (no row created, no email sent) after
 a single `SELECT`. `GET /api/auth/reset-password/validate` lets the frontend
 show a "this link is invalid" state before rendering the password form.
 `POST /api/auth/reset-password` completes it and — like signup — logs the
-user in immediately (`request.session["user_id"]`), since they've just proven
+user in immediately (`session_service.start_session`, see Active sessions
-they control the account's email.
+below), since they've just proven they control the account's email.
 
 Scope cuts: no rate limiting on `/forgot-password` (inherits the same
 documented gap as every other endpoint below, not a new one — the
@@ -606,6 +747,50 @@ unguessable expiring token is the actual protection once a request is made),
 no cleanup job for expired/used `password_resets` rows (same as
 `site_invites`, which has never had one either).
 
+## Active sessions
+
+Replaces the previously-stateless signed cookie (a bare `user_id`) with a
+real server-side `Session` table (`app/models/session.py`) — the cookie
+now only ever carries an opaque session id, resolved against this table
+via `session_service.resolve_session` on *every* request (`get_current_user`
+in `app/dependencies.py`, and the WS handshake in `app/ws/chat.py`), which
+is the single choke point that makes revocation actually take effect on a
+session's very next request rather than only once its cookie happens to
+expire.
+
+Each row records `ip_address` (`X-Forwarded-For`'s first entry, since
+production sits behind Nginx Proxy Manager — falls back to the direct peer
+address with nothing in front locally), `user_agent`, `created_at`, and a
+throttled `last_seen_at` (only bumped if stale by more than 5 minutes —
+`get_current_user` resolves a session on every authenticated request, so
+writing on every single one would turn a read into a write storm for no
+real benefit). `session_service.start_session` is the one place every
+"log this browser in" call site (login, signup completion, password-reset
+completion) creates the row and stashes its id in the cookie.
+
+- `GET /api/auth/sessions` — every non-revoked session for the current
+  user, newest-last-seen first, with a parsed "Browser on OS" label
+  (`app/services/user_agent_service.py` — plain substring checks against
+  the User-Agent header, no new dependency; special-cases an `Electron/`
+  token as "DS Chat Desktop" rather than the underlying Chromium version)
+  and `is_current` (compares against `request.state.session_id`, set by
+  `get_current_user`) so the frontend can label "this device" and treat
+  revoking it as a self-logout.
+- `DELETE /api/auth/sessions/{id}` — any of the current user's own
+  sessions, including their own current one (a remote sign-out of the
+  same device is a legitimate thing to do); 404 if it belongs to someone
+  else or is already revoked.
+- `POST /api/auth/logout` also revokes the session row, not just clears
+  the cookie (`revoke_session_unchecked` — no ownership check needed,
+  since a session can only ever log itself out, and never fails even if
+  the row is already gone).
+
+Scope cuts: changing your password doesn't proactively revoke other
+sessions (see Self-service password change and reset above) — this is a
+deliberate scope boundary, not an oversight, since it's a meaningfully
+different feature (auto-revoke-everywhere-on-password-change) from
+"let a user see and manually revoke what's logged in."
+
 ## Link previews
 
 Slack/Discord-style unfurling: the first `http(s)://` URL found in a
@@ -637,10 +822,13 @@ preview card fetched from that page's Open Graph tags (`og:title`,
   `Content-Type` is `text/html`.
 - **Cached by URL, not by message** (`link_previews` table, unique on
   `url`) — a URL posted by five different people in five different rooms
-  fetches once. A row also gets written on a *failed* fetch
+  within the same short window fetches once. A row also gets written on a
-  (`fetch_failed=True`) so a URL that genuinely doesn't unfurl (SSRF
+  *failed* fetch (`fetch_failed=True`) so a URL that genuinely doesn't
-  rejection, timeout, no usable title) isn't re-attempted on every message
+  unfurl (SSRF rejection, timeout, no usable title) isn't re-attempted on
-  that references it; both kinds expire after 7 days (`_CACHE_TTL`).
+  every message that references it; both kinds expire after 5 minutes
+  (`_CACHE_TTL` — #70: was 7 days, confirmed live as far too long, a
+  re-posted URL whose title/content had genuinely changed kept showing
+  the stale first-fetch preview for up to a week).
 - Parsed with stdlib `html.parser.HTMLParser`, not a new dependency — only
   meta-tag scraping is needed, not general HTML parsing.
 - Editing a message re-extracts the URL; if it changed or was removed, the
@@ -656,13 +844,16 @@ preview card fetched from that page's Open Graph tags (`og:title`,
 
 - Invite-only site registration: no `POST /api/auth/register`. Accounts are
   provisioned with `python -m app.cli create-user` (see step 4 above), or via
-  a site invite (see Site invites & email below). This is separate from
+  a site invite (see Site invites & email above). This is separate from
   adding an existing user to a private room — site accounts vs. room
   membership.
-- Sessions are signed cookies (Starlette `SessionMiddleware`), not a server-side
+- Sessions are backed by a real server-side table (`app/models/session.py`,
-  session table — see `ARCHITECTURE.md`'s rationale (simplest way to carry auth
+  see Active sessions above) — the signed cookie (Starlette
-  through a WebSocket handshake). This means there's currently no way to force-
+  `SessionMiddleware`) now only ever carries an opaque session id, resolved
-  revoke a session server-side; that needs a real session table later.
+  against that table on every request, which is what makes revocation
+  possible. Carrying auth through the WebSocket handshake automatically is
+  still why it's cookie-based at all, per `ARCHITECTURE.md`'s original
+  rationale.
 - No CSRF token yet — `SameSite=Lax` cookies plus a same-origin frontend dev
   proxy (see `../frontend/vite.config.ts`) is the accepted phase-1 mitigation.
 - Deleting a room explicitly deletes its messages/memberships first

backend/alembic/versions/05b28b0a2261_room_email_notifications_opt_in.py

@@ -0,0 +1,32 @@
+"""room email notifications opt-in
+
+Revision ID: 05b28b0a2261
+Revises: e2fc4d65f93e
+Create Date: 2026-08-28 19:34:23.507200
+
+"""
+from typing import Sequence, Union
+
+from alembic import op
+import sqlalchemy as sa
+
+
+# revision identifiers, used by Alembic.
+revision: str = '05b28b0a2261'
+down_revision: Union[str, Sequence[str], None] = 'e2fc4d65f93e'
+branch_labels: Union[str, Sequence[str], None] = None
+depends_on: Union[str, Sequence[str], None] = None
+
+
+def upgrade() -> None:
+    """Upgrade schema."""
+    # ### commands auto generated by Alembic - please adjust! ###
+    op.add_column('room_memberships', sa.Column('email_notifications', sa.Boolean(), server_default='false', nullable=False))
+    # ### end Alembic commands ###
+
+
+def downgrade() -> None:
+    """Downgrade schema."""
+    # ### commands auto generated by Alembic - please adjust! ###
+    op.drop_column('room_memberships', 'email_notifications')
+    # ### end Alembic commands ###

backend/alembic/versions/319c30e24cd9_add_sessions_table_for_active_sessions_.py

@@ -0,0 +1,44 @@
+"""add sessions table for active-sessions feature
+
+Revision ID: 319c30e24cd9
+Revises: 05b28b0a2261
+Create Date: 2026-08-28 19:59:51.475384
+
+"""
+from typing import Sequence, Union
+
+from alembic import op
+import sqlalchemy as sa
+
+
+# revision identifiers, used by Alembic.
+revision: str = '319c30e24cd9'
+down_revision: Union[str, Sequence[str], None] = '05b28b0a2261'
+branch_labels: Union[str, Sequence[str], None] = None
+depends_on: Union[str, Sequence[str], None] = None
+
+
+def upgrade() -> None:
+    """Upgrade schema."""
+    # ### commands auto generated by Alembic - please adjust! ###
+    op.create_table('sessions',
+    sa.Column('id', sa.Uuid(), nullable=False),
+    sa.Column('user_id', sa.Uuid(), nullable=False),
+    sa.Column('ip_address', sa.String(length=45), nullable=True),
+    sa.Column('user_agent', sa.String(length=500), nullable=True),
+    sa.Column('created_at', sa.DateTime(timezone=True), server_default=sa.text('now()'), nullable=False),
+    sa.Column('last_seen_at', sa.DateTime(timezone=True), server_default=sa.text('now()'), nullable=False),
+    sa.Column('revoked_at', sa.DateTime(timezone=True), nullable=True),
+    sa.ForeignKeyConstraint(['user_id'], ['users.id'], ),
+    sa.PrimaryKeyConstraint('id')
+    )
+    op.create_index(op.f('ix_sessions_user_id'), 'sessions', ['user_id'], unique=False)
+    # ### end Alembic commands ###
+
+
+def downgrade() -> None:
+    """Downgrade schema."""
+    # ### commands auto generated by Alembic - please adjust! ###
+    op.drop_index(op.f('ix_sessions_user_id'), table_name='sessions')
+    op.drop_table('sessions')
+    # ### end Alembic commands ###

backend/alembic/versions/339b78011a4f_add_user_text_scale_preference.py

@@ -0,0 +1,32 @@
+"""add user text_scale preference
+
+Revision ID: 339b78011a4f
+Revises: a318850726ee
+Create Date: 2026-08-30 18:03:16.159924
+
+"""
+from typing import Sequence, Union
+
+from alembic import op
+import sqlalchemy as sa
+
+
+# revision identifiers, used by Alembic.
+revision: str = '339b78011a4f'
+down_revision: Union[str, Sequence[str], None] = 'a318850726ee'
+branch_labels: Union[str, Sequence[str], None] = None
+depends_on: Union[str, Sequence[str], None] = None
+
+
+def upgrade() -> None:
+    """Upgrade schema."""
+    # ### commands auto generated by Alembic - please adjust! ###
+    op.add_column('users', sa.Column('text_scale', sa.String(length=20), nullable=True))
+    # ### end Alembic commands ###
+
+
+def downgrade() -> None:
+    """Downgrade schema."""
+    # ### commands auto generated by Alembic - please adjust! ###
+    op.drop_column('users', 'text_scale')
+    # ### end Alembic commands ###

backend/alembic/versions/9ca717f837c2_room_is_dm_flag_for_direct_messages.py

@@ -0,0 +1,35 @@
+"""room is_dm flag for direct messages
+
+Revision ID: 9ca717f837c2
+Revises: 9484fbd1cb3a
+Create Date: 2026-08-19 15:50:25.781735
+
+"""
+from typing import Sequence, Union
+
+from alembic import op
+import sqlalchemy as sa
+
+
+# revision identifiers, used by Alembic.
+revision: str = '9ca717f837c2'
+down_revision: Union[str, Sequence[str], None] = '9484fbd1cb3a'
+branch_labels: Union[str, Sequence[str], None] = None
+depends_on: Union[str, Sequence[str], None] = None
+
+
+def upgrade() -> None:
+    """Upgrade schema."""
+    # server_default backfills existing rows; dropped right after since the
+    # model itself only sets a Python-side default (see is_archived above).
+    op.add_column(
+        'rooms', sa.Column('is_dm', sa.Boolean(), nullable=False, server_default=sa.false())
+    )
+    op.alter_column('rooms', 'is_dm', server_default=None)
+
+
+def downgrade() -> None:
+    """Downgrade schema."""
+    # ### commands auto generated by Alembic - please adjust! ###
+    op.drop_column('rooms', 'is_dm')
+    # ### end Alembic commands ###

backend/alembic/versions/a318850726ee_add_custom_emoji.py

@@ -0,0 +1,43 @@
+"""add custom emoji
+
+Revision ID: a318850726ee
+Revises: 319c30e24cd9
+Create Date: 2026-08-28 20:34:27.293658
+
+"""
+from typing import Sequence, Union
+
+from alembic import op
+import sqlalchemy as sa
+
+
+# revision identifiers, used by Alembic.
+revision: str = 'a318850726ee'
+down_revision: Union[str, Sequence[str], None] = '319c30e24cd9'
+branch_labels: Union[str, Sequence[str], None] = None
+depends_on: Union[str, Sequence[str], None] = None
+
+
+def upgrade() -> None:
+    """Upgrade schema."""
+    # ### commands auto generated by Alembic - please adjust! ###
+    op.create_table('custom_emoji',
+    sa.Column('id', sa.Uuid(), nullable=False),
+    sa.Column('shortcode', sa.String(length=30), nullable=False),
+    sa.Column('storage_filename', sa.String(length=64), nullable=False),
+    sa.Column('content_type', sa.String(length=50), nullable=False),
+    sa.Column('uploaded_by', sa.Uuid(), nullable=False),
+    sa.Column('created_at', sa.DateTime(timezone=True), server_default=sa.text('now()'), nullable=False),
+    sa.ForeignKeyConstraint(['uploaded_by'], ['users.id'], ),
+    sa.PrimaryKeyConstraint('id')
+    )
+    op.create_index(op.f('ix_custom_emoji_shortcode'), 'custom_emoji', ['shortcode'], unique=True)
+    # ### end Alembic commands ###
+
+
+def downgrade() -> None:
+    """Downgrade schema."""
+    # ### commands auto generated by Alembic - please adjust! ###
+    op.drop_index(op.f('ix_custom_emoji_shortcode'), table_name='custom_emoji')
+    op.drop_table('custom_emoji')
+    # ### end Alembic commands ###

backend/alembic/versions/e2fc4d65f93e_allow_deleted_messages_to_clear_content_.py

@@ -0,0 +1,39 @@
+"""allow deleted messages to clear content and attachments
+
+Revision ID: e2fc4d65f93e
+Revises: f3f255da9c96
+Create Date: 2026-08-28 16:20:02.114630
+
+"""
+from typing import Sequence, Union
+
+from alembic import op
+import sqlalchemy as sa
+
+
+# revision identifiers, used by Alembic.
+revision: str = 'e2fc4d65f93e'
+down_revision: Union[str, Sequence[str], None] = 'f3f255da9c96'
+branch_labels: Union[str, Sequence[str], None] = None
+depends_on: Union[str, Sequence[str], None] = None
+
+
+def upgrade() -> None:
+    """Upgrade schema."""
+    op.drop_constraint('messages_content_or_attachment_required', 'messages', type_='check')
+    op.create_check_constraint(
+        'messages_content_or_attachment_required',
+        'messages',
+        'content IS NOT NULL OR image_id IS NOT NULL OR file_id IS NOT NULL '
+        'OR deleted_at IS NOT NULL',
+    )
+
+
+def downgrade() -> None:
+    """Downgrade schema."""
+    op.drop_constraint('messages_content_or_attachment_required', 'messages', type_='check')
+    op.create_check_constraint(
+        'messages_content_or_attachment_required',
+        'messages',
+        'content IS NOT NULL OR image_id IS NOT NULL OR file_id IS NOT NULL',
+    )

backend/alembic/versions/e81c9bcc82b9_add_user_emoji_scale_preference.py

@@ -0,0 +1,32 @@
+"""add user emoji_scale preference
+
+Revision ID: e81c9bcc82b9
+Revises: 339b78011a4f
+Create Date: 2026-08-30 18:14:26.045186
+
+"""
+from typing import Sequence, Union
+
+from alembic import op
+import sqlalchemy as sa
+
+
+# revision identifiers, used by Alembic.
+revision: str = 'e81c9bcc82b9'
+down_revision: Union[str, Sequence[str], None] = '339b78011a4f'
+branch_labels: Union[str, Sequence[str], None] = None
+depends_on: Union[str, Sequence[str], None] = None
+
+
+def upgrade() -> None:
+    """Upgrade schema."""
+    # ### commands auto generated by Alembic - please adjust! ###
+    op.add_column('users', sa.Column('emoji_scale', sa.String(length=20), nullable=True))
+    # ### end Alembic commands ###
+
+
+def downgrade() -> None:
+    """Downgrade schema."""
+    # ### commands auto generated by Alembic - please adjust! ###
+    op.drop_column('users', 'emoji_scale')
+    # ### end Alembic commands ###

backend/alembic/versions/f3f255da9c96_hide_dm_conversations_per_participant.py

@@ -0,0 +1,32 @@
+"""hide DM conversations per-participant
+
+Revision ID: f3f255da9c96
+Revises: 9ca717f837c2
+Create Date: 2026-08-19 16:36:28.332581
+
+"""
+from typing import Sequence, Union
+
+from alembic import op
+import sqlalchemy as sa
+
+
+# revision identifiers, used by Alembic.
+revision: str = 'f3f255da9c96'
+down_revision: Union[str, Sequence[str], None] = '9ca717f837c2'
+branch_labels: Union[str, Sequence[str], None] = None
+depends_on: Union[str, Sequence[str], None] = None
+
+
+def upgrade() -> None:
+    """Upgrade schema."""
+    # ### commands auto generated by Alembic - please adjust! ###
+    op.add_column('room_memberships', sa.Column('hidden_at', sa.DateTime(timezone=True), nullable=True))
+    # ### end Alembic commands ###
+
+
+def downgrade() -> None:
+    """Downgrade schema."""
+    # ### commands auto generated by Alembic - please adjust! ###
+    op.drop_column('room_memberships', 'hidden_at')
+    # ### end Alembic commands ###

backend/app/dependencies.py

@@ -8,6 +8,7 @@ from sqlalchemy.orm import selectinload
 from app.database import get_db
 from app.models import RoomMembership, RoomRole, User
 from app.services.bot_service import resolve_token
+from app.services.session_service import resolve_session
 
 _ROLE_RANK = {RoomRole.member: 0, RoomRole.admin: 1, RoomRole.owner: 2}
 
@@ -29,16 +30,26 @@ async def get_current_user(
         request.state.api_token = token
         return user
 
-    user_id = request.session.get("user_id")
+    session_id = request.session.get("session_id")
-    if not user_id:
+    if not session_id:
         raise HTTPException(status_code=401, detail="Not authenticated")
 
+    # #69: a session row, not a bare user_id -- resolve_session is also
+    # where a revoked session (this endpoint's own DELETE, or another
+    # device's "sign out") actually takes effect, since there's no other
+    # per-request check of that state.
+    session = await resolve_session(db, uuid.UUID(session_id))
+    if session is None:
+        request.session.clear()
+        raise HTTPException(status_code=401, detail="Not authenticated")
+    request.state.session_id = session.id
+
     # Eager-loaded so UserRead.active_custom_theme (app/schemas/user.py) can
     # be read without a MissingGreenlet -- selectinload skips the second
     # query entirely when active_custom_theme_id is null (the common case),
     # so this costs nothing for users who've never set a custom theme.
     user = await db.get(
-        User, uuid.UUID(user_id), options=[selectinload(User.active_custom_theme)]
+        User, session.user_id, options=[selectinload(User.active_custom_theme)]
     )
     if user is None or not user.is_active:
         request.session.clear()

backend/app/main.py

@@ -15,6 +15,7 @@ from app.routers import (
     admin,
     auth,
     bots,
+    custom_emoji,
     custom_themes,
     health,
     push,
@@ -27,6 +28,7 @@ from app.routers import (
 from app.ws.broadcaster import Broadcaster
 from app.ws.chat import router as ws_router
 from app.ws.connection_manager import ConnectionManager
+from app.ws.focus_presence import FocusPresence
 from app.ws.global_presence import GlobalPresence
 from app.ws.presence import Presence
 
@@ -82,6 +84,7 @@ def create_app() -> FastAPI:
     app.state.redis = Redis.from_url(settings.redis_url, decode_responses=True)
     app.state.presence = Presence(app.state.redis)
     app.state.global_presence = GlobalPresence(app.state.redis)
+    app.state.focus_presence = FocusPresence(app.state.redis)
     app.state.broadcaster = Broadcaster(app.state.redis, app.state.connection_manager)
 
     app.include_router(health.router)
@@ -91,6 +94,7 @@ def create_app() -> FastAPI:
     app.include_router(users.router)
     app.include_router(push.router)
     app.include_router(custom_themes.router)
+    app.include_router(custom_emoji.router)
     app.include_router(uploads.router)
     app.include_router(admin.router)
     app.include_router(bots.router)

backend/app/models/__init__.py

@@ -1,6 +1,7 @@
 from app.models.admin_audit_log import AdminAuditLog
 from app.models.api_token import ApiToken
 from app.models.base import Base
+from app.models.custom_emoji import CustomEmoji
 from app.models.custom_theme import CustomTheme
 from app.models.event_subscription import EventSubscription
 from app.models.invite import InviteStatus
@@ -15,6 +16,7 @@ from app.models.message_room_reference import MessageRoomReference
 from app.models.password_reset import PasswordReset
 from app.models.push_subscription import PushSubscription
 from app.models.room import Room
+from app.models.session import Session
 from app.models.site_invite import SiteInvite
 from app.models.smtp_settings import SmtpSettings
 from app.models.upload_settings import UploadSettings
@@ -35,6 +37,7 @@ __all__ = [
     "MessageRoomReference",
     "InviteStatus",
     "PasswordReset",
+    "Session",
     "SiteInvite",
     "SmtpSettings",
     "UploadSettings",
@@ -44,5 +47,6 @@ __all__ = [
     "WebhookIncoming",
     "EventSubscription",
     "CustomTheme",
+    "CustomEmoji",
     "LinkPreview",
 ]

backend/app/models/custom_emoji.py

@@ -0,0 +1,28 @@
+import uuid
+from datetime import datetime
+
+from sqlalchemy import DateTime, ForeignKey, String, func
+from sqlalchemy.orm import Mapped, mapped_column, relationship
+
+from app.models.base import Base
+
+
+class CustomEmoji(Base):
+    __tablename__ = "custom_emoji"
+
+    id: Mapped[uuid.UUID] = mapped_column(primary_key=True, default=uuid.uuid4)
+    # #18: site-wide, not room-scoped -- kept globally unique so a bare
+    # `:shortcode:` in any message/reaction is unambiguous without also
+    # knowing which room it was posted in. 30 chars, not 32 -- the stored
+    # *reference* in MessageReaction.emoji (String(32)) is the shortcode
+    # wrapped in colons, so this is sized to leave room for both without
+    # widening that column.
+    shortcode: Mapped[str] = mapped_column(String(30), unique=True, index=True, nullable=False)
+    storage_filename: Mapped[str] = mapped_column(String(64), nullable=False)
+    content_type: Mapped[str] = mapped_column(String(50), nullable=False)
+    uploaded_by: Mapped[uuid.UUID] = mapped_column(ForeignKey("users.id"), nullable=False)
+    created_at: Mapped[datetime] = mapped_column(
+        DateTime(timezone=True), server_default=func.now(), nullable=False
+    )
+
+    uploader = relationship("User")

backend/app/models/membership.py

@@ -2,7 +2,7 @@ import enum
 import uuid
 from datetime import datetime
 
-from sqlalchemy import DateTime, Enum, ForeignKey, PrimaryKeyConstraint, func
+from sqlalchemy import Boolean, DateTime, Enum, ForeignKey, PrimaryKeyConstraint, func
 from sqlalchemy.orm import Mapped, mapped_column, relationship
 
 from app.models.base import Base
@@ -33,6 +33,23 @@ class RoomMembership(Base):
     last_read_at: Mapped[datetime] = mapped_column(
         DateTime(timezone=True), server_default=func.now(), nullable=False
     )
+    # #52 follow-up: lets a DM be hidden from one participant's own sidebar
+    # without touching the other participant's copy or deleting anything --
+    # a DM has no sensible "leave" (it would corrupt find_or_create_dm's
+    # exactly-two-members assumption), so this is deliberately a per-viewer
+    # display flag on their own membership row, not a membership deletion.
+    # Cleared automatically (see message_events.py) whenever a new message
+    # arrives in the room, or when find_or_create_dm resolves back to it --
+    # both count as the conversation being active again.
+    hidden_at: Mapped[datetime | None] = mapped_column(DateTime(timezone=True))
+    # #67: opt-in, per-member -- email while offline on the room's first
+    # unread message, plus every mention regardless of that debounce (see
+    # message_events.py's _maybe_email_room_notifications). Deliberately
+    # separate from #66's DM emails (always-on, no toggle) rather than a
+    # shared flag, since DMs are explicitly out of scope for this setting.
+    email_notifications: Mapped[bool] = mapped_column(
+        Boolean, default=False, server_default="false", nullable=False
+    )
 
     room = relationship("Room", back_populates="memberships")
     user = relationship("User")

backend/app/models/message.py

@@ -10,8 +10,12 @@ from app.models.base import Base
 class Message(Base):
     __tablename__ = "messages"
     __table_args__ = (
+        # #53: a deleted message clears content/image_id/file_id entirely
+        # (see message_service.delete_message) -- the "must have something"
+        # rule only applies while the message is actually live.
         CheckConstraint(
-            "content IS NOT NULL OR image_id IS NOT NULL OR file_id IS NOT NULL",
+            "content IS NOT NULL OR image_id IS NOT NULL OR file_id IS NOT NULL "
+            "OR deleted_at IS NOT NULL",
             name="messages_content_or_attachment_required",
         ),
     )

backend/app/models/room.py

@@ -15,6 +15,10 @@ class Room(Base):
     description: Mapped[str | None] = mapped_column(Text)
     is_private: Mapped[bool] = mapped_column(Boolean, default=False, nullable=False)
     is_archived: Mapped[bool] = mapped_column(Boolean, default=False, nullable=False)
+    # #52: a DM is a Room whose `name` is an internal, never-displayed
+    # deterministic token (see room_service.dm_room_name) rather than a
+    # user-chosen name -- see that function's docstring for the scheme.
+    is_dm: Mapped[bool] = mapped_column(Boolean, default=False, nullable=False)
     owner_id: Mapped[uuid.UUID] = mapped_column(ForeignKey("users.id"), nullable=False)
     created_at: Mapped[datetime] = mapped_column(
         DateTime(timezone=True), server_default=func.now(), nullable=False

backend/app/models/session.py

@@ -0,0 +1,43 @@
+import uuid
+from datetime import datetime
+
+from sqlalchemy import DateTime, ForeignKey, String, func
+from sqlalchemy.orm import Mapped, mapped_column, relationship
+
+from app.models.base import Base
+
+
+class Session(Base):
+    __tablename__ = "sessions"
+
+    # #69: the row's own id doubles as the opaque value stored in the
+    # signed session cookie (see app/dependencies.py) -- no separate
+    # generate_token()/hash_token() pair like ApiToken needs. A bearer API
+    # token has to be looked up *by itself* from a plaintext string a bot
+    # pastes into an Authorization header (real leak risk, hence hashing
+    # it at rest); this id only ever travels inside itsdangerous's signed,
+    # tamper-proof cookie payload, so a plain UUID primary key carries the
+    # same security properties the stateless cookie already had before
+    # this table existed.
+    id: Mapped[uuid.UUID] = mapped_column(primary_key=True, default=uuid.uuid4)
+    user_id: Mapped[uuid.UUID] = mapped_column(ForeignKey("users.id"), index=True, nullable=False)
+    # 45 chars fits the longest possible IPv6 text representation.
+    ip_address: Mapped[str | None] = mapped_column(String(45))
+    user_agent: Mapped[str | None] = mapped_column(String(500))
+    created_at: Mapped[datetime] = mapped_column(
+        DateTime(timezone=True), server_default=func.now(), nullable=False
+    )
+    # Bumped (throttled, not on every request -- see session_service.py) so
+    # "active sessions" can be sorted/labeled by actual recent use, not just
+    # login time -- a session opened once a week ago and used constantly
+    # since should not look identical to one opened once and abandoned.
+    last_seen_at: Mapped[datetime] = mapped_column(
+        DateTime(timezone=True), server_default=func.now(), nullable=False
+    )
+    # Null while active. Set on explicit logout or a deliberate "sign out
+    # this device" from another session -- never deleted outright, so a
+    # revoked row still means something if anyone ever needs to ask "was
+    # this session valid at time X."
+    revoked_at: Mapped[datetime | None] = mapped_column(DateTime(timezone=True))
+
+    user = relationship("User")

backend/app/models/user.py

@@ -19,6 +19,17 @@ class User(Base):
     is_active: Mapped[bool] = mapped_column(Boolean, default=True, nullable=False)
     display_name: Mapped[str | None] = mapped_column(String(50))
     theme: Mapped[str | None] = mapped_column(String(20))
+    # #71: null means "normal" (the pre-existing default before this
+    # setting existed) -- a preset name, not a raw scale factor, so it's
+    # validated/enumerable the same way `theme` already is rather than
+    # accepting an arbitrary float.
+    text_scale: Mapped[str | None] = mapped_column(String(20))
+    # #71: independent of text_scale above -- scales emoji rendered in
+    # message text specifically, not the whole UI (see
+    # frontend/src/components/MessageContent.tsx's --emoji-scale, scoped
+    # to message content only so it can't also inflate the emoji picker's
+    # grid or reaction pills).
+    emoji_scale: Mapped[str | None] = mapped_column(String(20))
     # Only meaningful when theme == "custom" -- which of this user's saved
     # CustomTheme rows (app/models/custom_theme.py) is currently active.
     # Cleared explicitly (not via a DB-level ON DELETE) whenever that theme

backend/app/routers/admin.py

@@ -38,6 +38,7 @@ from app.services.site_invite_service import (
     SiteInviteNotPendingError,
     create_site_invite,
     list_site_invites,
+    resend_site_invite,
     revoke_site_invite,
 )
 from app.services.smtp_settings_service import get_smtp_settings, upsert_smtp_settings
@@ -322,6 +323,22 @@ async def revoke_site_invite_endpoint(
         raise HTTPException(status_code=400, detail="Invite is no longer pending")
 
 
+@router.post("/invites/{invite_id}/resend", response_model=SiteInviteRead)
+async def resend_site_invite_endpoint(
+    invite_id: uuid.UUID,
+    request: Request,
+    current_user: User = Depends(get_current_user),
+    db: AsyncSession = Depends(get_db),
+):
+    require_site_admin(current_user)
+    try:
+        return await resend_site_invite(db, current_user, str(request.base_url), invite_id)
+    except SiteInviteNotFoundError:
+        raise HTTPException(status_code=404, detail="Invite not found")
+    except SiteInviteNotPendingError:
+        raise HTTPException(status_code=400, detail="Invite is no longer pending")
+
+
 @router.get("/settings/smtp", response_model=SmtpSettingsRead | None)
 async def get_smtp_settings_endpoint(
     current_user: User = Depends(get_current_user),
@@ -376,7 +393,7 @@ async def test_smtp_settings_endpoint(
 ):
     require_site_admin(current_user)
     try:
-        await send_test_email(db, current_user.email)
+        await send_test_email(db, current_user.email, theme_user=current_user)
     except SmtpNotConfiguredError:
         raise HTTPException(status_code=400, detail="SMTP is not configured yet")
     except Exception as exc:

backend/app/routers/auth.py

@@ -1,3 +1,5 @@
+import uuid
+
 from fastapi import APIRouter, Depends, File, HTTPException, Query, Request, Response, UploadFile
 from sqlalchemy.ext.asyncio import AsyncSession
 from sqlalchemy.orm import selectinload
@@ -7,6 +9,7 @@ from app.dependencies import get_current_user
 from app.models import User
 from app.schemas.auth import LoginRequest
 from app.schemas.password import ForgotPasswordRequest, PasswordChange, ResetPasswordComplete
+from app.schemas.session import SessionRead
 from app.schemas.user import ProfileUpdate, UserRead
 from app.services.auth_service import (
     AccountDeactivatedError,
@@ -22,7 +25,15 @@ from app.services.password_service import (
     request_password_reset,
     validate_reset_token,
 )
+from app.services.session_service import (
+    SessionNotFoundError,
+    list_sessions,
+    revoke_session,
+    revoke_session_unchecked,
+    start_session,
+)
 from app.services.upload_settings_service import format_mb, get_upload_settings
+from app.services.user_agent_service import describe_user_agent
 from app.storage import (
     ALLOWED_IMAGE_CONTENT_TYPES,
     InvalidImageError,
@@ -55,12 +66,15 @@ async def login(
     except AccountDeactivatedError:
         raise HTTPException(status_code=401, detail="Account is deactivated")
 
-    request.session["user_id"] = str(user.id)
+    await start_session(request, db, user.id)
     return user
 
 
 @router.post("/logout", status_code=204)
-async def logout(request: Request) -> Response:
+async def logout(request: Request, db: AsyncSession = Depends(get_db)) -> Response:
+    session_id = request.session.get("session_id")
+    if session_id:
+        await revoke_session_unchecked(db, uuid.UUID(session_id))
     request.session.clear()
     return Response(status_code=204)
 
@@ -86,6 +100,10 @@ async def update_profile(
         current_user.display_name = display_name or None
     if "theme" in updates:
         current_user.theme = updates["theme"]
+    if "text_scale" in updates:
+        current_user.text_scale = updates["text_scale"]
+    if "emoji_scale" in updates:
+        current_user.emoji_scale = updates["emoji_scale"]
     if "appear_offline" in updates:
         current_user.appear_offline = updates["appear_offline"]
     await db.commit()
@@ -218,5 +236,37 @@ async def complete_reset_password_endpoint(
     except PasswordResetInvalidError:
         raise HTTPException(status_code=400, detail="This reset link is invalid or has expired")
 
-    request.session["user_id"] = str(user.id)
+    await start_session(request, db, user.id)
     return user
+
+
+@router.get("/sessions", response_model=list[SessionRead])
+async def list_sessions_endpoint(
+    request: Request,
+    current_user: User = Depends(get_current_user),
+    db: AsyncSession = Depends(get_db),
+):
+    sessions = await list_sessions(db, current_user.id)
+    return [
+        SessionRead(
+            id=s.id,
+            ip_address=s.ip_address,
+            device_label=describe_user_agent(s.user_agent),
+            created_at=s.created_at,
+            last_seen_at=s.last_seen_at,
+            is_current=s.id == request.state.session_id,
+        )
+        for s in sessions
+    ]
+
+
+@router.delete("/sessions/{session_id}", status_code=204)
+async def revoke_session_endpoint(
+    session_id: uuid.UUID,
+    current_user: User = Depends(get_current_user),
+    db: AsyncSession = Depends(get_db),
+):
+    try:
+        await revoke_session(db, current_user.id, session_id)
+    except SessionNotFoundError:
+        raise HTTPException(status_code=404, detail="Session not found")

backend/app/routers/custom_emoji.py

@@ -0,0 +1,139 @@
+import uuid
+
+from fastapi import APIRouter, Depends, File, Form, HTTPException, UploadFile
+from fastapi.responses import FileResponse
+from sqlalchemy.ext.asyncio import AsyncSession
+
+from app.database import get_db
+from app.dependencies import get_current_user
+from app.models import User
+from app.schemas.custom_emoji import CustomEmojiRead
+from app.services.custom_emoji_service import (
+    SHORTCODE_PATTERN,
+    CustomEmojiNotFoundError,
+    DuplicateShortcodeError,
+    InvalidShortcodeError,
+    NotEmojiOwnerError,
+    create_custom_emoji,
+    delete_custom_emoji,
+    get_custom_emoji_by_shortcode,
+    list_custom_emoji,
+)
+from app.services.upload_settings_service import format_mb, get_upload_settings
+from app.storage import (
+    ALLOWED_IMAGE_CONTENT_TYPES,
+    UPLOADS_DIR,
+    InvalidImageError,
+    UploadTooLargeError,
+    process_image,
+    read_capped,
+    save_file,
+)
+
+# Small and square -- these render inline in message text/reaction pills at
+# roughly text size, nowhere near message-image or avatar dimensions.
+CUSTOM_EMOJI_MAX_DIMENSION = 128
+
+router = APIRouter(prefix="/api/custom-emoji", tags=["custom-emoji"])
+
+
+@router.post("", response_model=CustomEmojiRead, status_code=201)
+async def upload_custom_emoji_endpoint(
+    shortcode: str = Form(...),
+    file: UploadFile = File(...),
+    current_user: User = Depends(get_current_user),
+    db: AsyncSession = Depends(get_db),
+):
+    shortcode = shortcode.strip().lower()
+    # Checked here, before any file processing/saving, so the common
+    # rejection cases (bad format, name taken) never leave an orphaned
+    # file on disk -- create_custom_emoji below still re-checks both
+    # (the actual source of truth, and the only thing that closes the
+    # TOCTOU race on the uniqueness check).
+    if not SHORTCODE_PATTERN.match(shortcode):
+        raise HTTPException(
+            status_code=400,
+            detail="Shortcode must be 2-30 characters: lowercase letters, numbers, hyphens, underscores",
+        )
+    if await get_custom_emoji_by_shortcode(db, shortcode) is not None:
+        raise HTTPException(status_code=409, detail="An emoji with that shortcode already exists")
+
+    if file.content_type not in ALLOWED_IMAGE_CONTENT_TYPES:
+        raise HTTPException(status_code=400, detail="Unsupported image type")
+
+    upload_settings = await get_upload_settings(db)
+    try:
+        data = await read_capped(file, cap=upload_settings.max_upload_bytes)
+    except UploadTooLargeError:
+        raise HTTPException(
+            status_code=413,
+            detail=f"Image exceeds {format_mb(upload_settings.max_upload_bytes)} limit",
+        )
+
+    try:
+        data, ext = process_image(
+            data, file.content_type, square=True, max_dimension=CUSTOM_EMOJI_MAX_DIMENSION
+        )
+    except InvalidImageError:
+        raise HTTPException(status_code=400, detail="File is not a valid image")
+
+    storage_filename = save_file(data, ext)
+    try:
+        return await create_custom_emoji(
+            db, current_user.id, shortcode, storage_filename, file.content_type
+        )
+    except (InvalidShortcodeError, DuplicateShortcodeError):
+        # Already checked above -- only reachable via the uniqueness
+        # check's TOCTOU race (two uploads of the same new shortcode at
+        # once), not the common case.
+        raise HTTPException(status_code=409, detail="An emoji with that shortcode already exists")
+
+
+@router.get("", response_model=list[CustomEmojiRead])
+async def list_custom_emoji_endpoint(
+    current_user: User = Depends(get_current_user),
+    db: AsyncSession = Depends(get_db),
+):
+    return await list_custom_emoji(db)
+
+
+@router.delete("/{emoji_id}", status_code=204)
+async def delete_custom_emoji_endpoint(
+    emoji_id: uuid.UUID,
+    current_user: User = Depends(get_current_user),
+    db: AsyncSession = Depends(get_db),
+):
+    try:
+        await delete_custom_emoji(db, emoji_id, current_user)
+    except CustomEmojiNotFoundError:
+        raise HTTPException(status_code=404, detail="Custom emoji not found")
+    except NotEmojiOwnerError:
+        raise HTTPException(status_code=403, detail="Only the uploader or a site admin can remove this")
+
+
+@router.get("/{shortcode}/image")
+async def get_custom_emoji_image_endpoint(
+    shortcode: str,
+    current_user: User = Depends(get_current_user),
+    db: AsyncSession = Depends(get_db),
+):
+    emoji = await get_custom_emoji_by_shortcode(db, shortcode)
+    if emoji is None:
+        raise HTTPException(status_code=404, detail="Custom emoji not found")
+    return FileResponse(
+        UPLOADS_DIR / emoji.storage_filename,
+        media_type=emoji.content_type,
+        # #18 follow-up: `max-age=300` (the avatar endpoint's own
+        # convention) meant a browser that had already fetched this
+        # shortcode's image kept serving it from cache for up to 5 minutes
+        # after a delete-and-reupload under the same name swapped in a
+        # genuinely different file underneath the same URL -- confirmed
+        # live, re-adding an emoji with a just-deleted shortcode showed the
+        # old image. `no-cache` (despite the name, still cacheable) forces
+        # a revalidation round trip on every use instead of trusting a
+        # timed cache -- FileResponse already sets ETag/Last-Modified from
+        # the file's own mtime+size (see Starlette's set_stat_headers), so
+        # an unchanged file still gets served as a cheap 304 and only an
+        # actually-different one (any re-upload) returns fresh bytes.
+        headers={"Cache-Control": "private, no-cache"},
+    )

backend/app/routers/rooms.py

@@ -17,6 +17,7 @@ from app.schemas.message import LinkPreviewInfo, MessageFileInfo, MessageRead
 from app.schemas.message_file import MessageFileCreated
 from app.schemas.message_image import MessageImageCreated
 from app.schemas.room import (
+    DmPartnerInfo,
     MyRoomItem,
     RoomAttachmentRead,
     RoomCreate,
@@ -24,8 +25,10 @@ from app.schemas.room import (
     RoomMemberAdd,
     RoomMemberRead,
     RoomMemberRoleUpdate,
+    RoomNotificationSettingsUpdate,
     RoomRead,
     RoomUpdate,
+    StartDmRequest,
     TransferOwnershipRequest,
 )
 from app.schemas.webhook import (
@@ -36,19 +39,24 @@ from app.schemas.webhook import (
     WebhookIncomingRead,
 )
 from app.services.link_preview_service import get_link_previews_for_urls
-from app.services.message_events import broadcast_room_added
+from app.services.message_events import broadcast_new_message, broadcast_room_added
 from app.services.message_service import (
+    create_message,
     get_reactions_for_messages,
     list_recent_messages,
     list_room_attachments,
 )
+from app.services.system_user_service import get_or_create_system_user
 from app.services.upload_settings_service import format_mb, get_upload_settings
 from app.services.room_service import (
     AlreadyMemberError,
+    CannotDmSelfError,
+    CannotModifyDmError,
     CannotRemoveOwnerError,
     DuplicateRoomError,
     InsufficientRoleError,
     MembershipNotFoundError,
+    NotADmError,
     OwnerMustTransferError,
     RoomIsPrivateError,
     RoomNotFoundError,
@@ -57,7 +65,9 @@ from app.services.room_service import (
     change_member_role,
     create_room,
     delete_room,
+    find_or_create_dm,
     get_room,
+    hide_dm,
     join_room,
     leave_room,
     list_member_rooms,
@@ -65,6 +75,7 @@ from app.services.room_service import (
     list_room_members,
     mark_room_read,
     remove_member,
+    set_room_email_notifications,
     transfer_ownership,
     update_room,
 )
@@ -82,6 +93,7 @@ from app.services.webhook_service import (
 from app.services.ssrf import UnsafeUrlError
 from app.storage import (
     ALLOWED_IMAGE_CONTENT_TYPES,
+    INLINE_SAFE_VIDEO_CONTENT_TYPES,
     UPLOADS_DIR,
     InvalidImageError,
     UploadTooLargeError,
@@ -105,6 +117,28 @@ async def create_room_endpoint(
         raise HTTPException(status_code=409, detail="A room with this name already exists")
 
 
+@router.post("/dm", response_model=RoomRead, status_code=201)
+async def start_dm_endpoint(
+    data: StartDmRequest,
+    request: Request,
+    current_user: User = Depends(get_current_user),
+    db: AsyncSession = Depends(get_db),
+):
+    try:
+        room = await find_or_create_dm(db, current_user.id, data.other_user_id)
+    except CannotDmSelfError:
+        raise HTTPException(status_code=400, detail="Cannot start a DM with yourself")
+    except TargetUserNotFoundError:
+        raise HTTPException(status_code=404, detail="No user with that ID")
+    # Same signal add_member sends -- without it, the other participant's
+    # already-open client has no way to know this DM exists until they
+    # reload: GET /rooms/mine is only fetched once at app mount. Sent
+    # unconditionally (not just on genuine creation) since re-finding an
+    # existing DM and refreshing their room list again is harmless.
+    await broadcast_room_added(request.app.state.broadcaster, data.other_user_id, room)
+    return room
+
+
 @router.get("", response_model=list[RoomListItem])
 async def list_rooms_endpoint(
     current_user: User = Depends(get_current_user),
@@ -117,6 +151,8 @@ async def list_rooms_endpoint(
             name=room.name,
             description=room.description,
             is_private=room.is_private,
+            is_dm=room.is_dm,
+            is_archived=room.is_archived,
             owner_id=room.owner_id,
             created_at=room.created_at,
             is_member=is_member,
@@ -127,23 +163,40 @@ async def list_rooms_endpoint(
 
 @router.get("/mine", response_model=list[MyRoomItem])
 async def list_my_rooms_endpoint(
+    request: Request,
     current_user: User = Depends(get_current_user),
     db: AsyncSession = Depends(get_db),
 ):
     rooms = await list_member_rooms(db, current_user.id)
+    partner_ids = [partner.id for *_, partner in rooms if partner is not None]
+    online_ids = await request.app.state.global_presence.online_user_ids(partner_ids)
     return [
         MyRoomItem(
             id=room.id,
             name=room.name,
             description=room.description,
             is_private=room.is_private,
+            is_dm=room.is_dm,
+            is_archived=room.is_archived,
             owner_id=room.owner_id,
             created_at=room.created_at,
             role=role,
             has_unread=has_unread,
             has_mention=has_mention,
+            email_notifications=email_notifications,
+            dm_partner=(
+                DmPartnerInfo(
+                    user_id=partner.id,
+                    username=partner.username,
+                    display_name=partner.display_name,
+                    avatar_filename=partner.avatar_filename,
+                    status=_member_status(partner, online_ids),
                 )
-        for room, role, has_unread, has_mention in rooms
+                if partner is not None
+                else None
+            ),
+        )
+        for room, role, has_unread, has_mention, email_notifications, partner in rooms
     ]
 
 
@@ -167,6 +220,8 @@ async def update_room_endpoint(
         raise HTTPException(status_code=404, detail="Room not found")
     except DuplicateRoomError:
         raise HTTPException(status_code=409, detail="A room with this name already exists")
+    except CannotModifyDmError:
+        raise HTTPException(status_code=400, detail="DMs can't be edited")
 
 
 @router.delete("/{room_id}", status_code=204)
@@ -215,6 +270,24 @@ async def leave_room_endpoint(
         raise HTTPException(status_code=404, detail="Not a member of this room")
 
 
+@router.post("/{room_id}/hide", status_code=204)
+async def hide_dm_endpoint(
+    room_id: uuid.UUID,
+    current_user: User = Depends(get_current_user),
+    db: AsyncSession = Depends(get_db),
+):
+    await require_room_member(room_id, current_user, db)
+    try:
+        room = await get_room(db, room_id)
+        await hide_dm(db, room, current_user.id)
+    except RoomNotFoundError:
+        raise HTTPException(status_code=404, detail="Room not found")
+    except NotADmError:
+        raise HTTPException(status_code=400, detail="Only DMs can be hidden")
+    except MembershipNotFoundError:
+        raise HTTPException(status_code=404, detail="Not a member of this room")
+
+
 @router.post("/{room_id}/read", status_code=204)
 async def mark_room_read_endpoint(
     room_id: uuid.UUID,
@@ -225,6 +298,20 @@ async def mark_room_read_endpoint(
     await mark_room_read(db, room_id, current_user.id)
 
 
+@router.patch("/{room_id}/notifications", status_code=204)
+async def update_room_notifications_endpoint(
+    room_id: uuid.UUID,
+    data: RoomNotificationSettingsUpdate,
+    current_user: User = Depends(get_current_user),
+    db: AsyncSession = Depends(get_db),
+):
+    await require_room_member(room_id, current_user, db)
+    try:
+        await set_room_email_notifications(db, room_id, current_user.id, data.email_notifications)
+    except CannotModifyDmError:
+        raise HTTPException(status_code=400, detail="Email notifications aren't available for DMs")
+
+
 def _member_status(user: User, online_ids: set[uuid.UUID]) -> str:
     # appear_offline always wins, regardless of actual connection -- that's
     # the whole point of the override (lurking in a room undetected).
@@ -366,6 +453,7 @@ async def get_room_messages_endpoint(
             reactions=reactions_by_message.get(m.id, []),
             created_at=m.created_at,
             edited_at=m.edited_at,
+            deleted_at=m.deleted_at,
         )
         for m in messages
     ]
@@ -480,12 +568,25 @@ async def get_room_file_endpoint(
     message_file = await db.get(MessageFile, file_id)
     if message_file is None or message_file.room_id != room_id:
         raise HTTPException(status_code=404, detail="File not found")
+    # #65: a browser-playable video is served inline (no filename=) so a
+    # <video> tag can actually play it instead of triggering a download --
+    # gated to a strict allowlist (INLINE_SAFE_VIDEO_CONTENT_TYPES), the
+    # same reasoning MessageImage's own endpoint already relies on: these
+    # are content types a browser only ever interprets as media, never as
+    # something that could execute script, so the attachment-disposition
+    # mitigation below doesn't need to apply to them.
+    if message_file.content_type in INLINE_SAFE_VIDEO_CONTENT_TYPES:
+        return FileResponse(
+            UPLOADS_DIR / message_file.storage_filename,
+            media_type=message_file.content_type,
+            headers={"Cache-Control": "private, max-age=31536000, immutable"},
+        )
     # `filename=` makes Starlette set Content-Disposition: attachment,
     # forcing a download instead of an inline render regardless of
     # content-type -- the mitigation for a same-origin-served, user-
     # uploaded file (e.g. .html/.svg) executing script in this app's own
     # origin if opened directly. No content-type allowlist needed on top
-    # of this; see backend/README.md.
+    # of this beyond the video carve-out above; see backend/README.md.
     return FileResponse(
         UPLOADS_DIR / message_file.storage_filename,
         media_type=message_file.content_type,
@@ -556,7 +657,37 @@ async def add_member_endpoint(
         raise HTTPException(status_code=404, detail="No user with that ID")
     except AlreadyMemberError:
         raise HTTPException(status_code=409, detail="That user is already a member")
+
+    # room_added first -- the new member's client needs to know this room
+    # exists before it can make sense of an unread_update for it, which the
+    # welcome message below would otherwise trigger out of order.
     await broadcast_room_added(request.app.state.broadcaster, data.user_id, room)
+
+    # #74: posted as the auto-provisioned System account, not the admin who
+    # did the adding -- "Welcome, bob!" reads as coming from the room/app
+    # itself, not as something the admin personally typed.
+    system_user = await get_or_create_system_user(db)
+    welcome_name = membership.user.display_name or membership.user.username
+    welcome_message = await create_message(
+        db, room.id, system_user.id, f"Welcome to #{room.name}, {welcome_name}!"
+    )
+    # Same "sending implies having seen the room" reasoning as ws/chat.py's
+    # own live-message path -- the admin is the one who caused this message,
+    # and is presumably already looking at this room's member management, so
+    # without this their own client would show it as unread regardless.
+    await mark_room_read(db, room.id, current_user.id)
+    await broadcast_new_message(
+        db,
+        request.app.state.broadcaster,
+        request.app.state.presence,
+        request.app.state.focus_presence,
+        request.app.state.global_presence,
+        str(request.base_url),
+        room.id,
+        welcome_message,
+        system_user,
+    )
+
     online_ids = await request.app.state.global_presence.online_user_ids([membership.user_id])
     return RoomMemberRead(
         user_id=membership.user_id,

backend/app/routers/signup.py

@@ -5,6 +5,7 @@ from app.database import get_db
 from app.schemas.site_invite import SignupComplete, SignupValidateRead
 from app.schemas.user import UserRead
 from app.services.auth_service import DuplicateUserError
+from app.services.session_service import start_session
 from app.services.site_invite_service import (
     SiteInviteInvalidError,
     complete_signup,
@@ -39,5 +40,5 @@ async def complete_signup_endpoint(
     except DuplicateUserError:
         raise HTTPException(status_code=409, detail="That username or email is already taken")
 
-    request.session["user_id"] = str(user.id)
+    await start_session(request, db, user.id)
     return user

backend/app/routers/webhooks.py

@@ -4,7 +4,7 @@ from sqlalchemy.ext.asyncio import AsyncSession
 from app.database import get_db
 from app.schemas.webhook import IncomingWebhookPost
 from app.services.message_events import broadcast_new_message
-from app.services.webhook_service import WebhookNotFoundError, post_via_webhook
+from app.services.webhook_service import RoomArchivedError, WebhookNotFoundError, post_via_webhook
 
 router = APIRouter(prefix="/api/webhooks", tags=["webhooks"])
 
@@ -22,7 +22,21 @@ async def incoming_webhook_endpoint(
         message, room, sender = await post_via_webhook(db, token, data.content)
     except WebhookNotFoundError:
         raise HTTPException(status_code=404, detail="Unknown webhook")
+    except RoomArchivedError:
+        raise HTTPException(status_code=403, detail="This room has been archived and is read-only")
 
     broadcaster = request.app.state.broadcaster
     presence = request.app.state.presence
-    await broadcast_new_message(db, broadcaster, presence, room.id, message, sender)
+    focus_presence = request.app.state.focus_presence
+    global_presence = request.app.state.global_presence
+    await broadcast_new_message(
+        db,
+        broadcaster,
+        presence,
+        focus_presence,
+        global_presence,
+        str(request.base_url),
+        room.id,
+        message,
+        sender,
+    )

backend/app/schemas/custom_emoji.py

@@ -0,0 +1,13 @@
+import uuid
+from datetime import datetime
+
+from pydantic import BaseModel, ConfigDict
+
+
+class CustomEmojiRead(BaseModel):
+    model_config = ConfigDict(from_attributes=True)
+
+    id: uuid.UUID
+    shortcode: str
+    uploaded_by: uuid.UUID
+    created_at: datetime

backend/app/schemas/message.py

@@ -44,3 +44,9 @@ class MessageRead(BaseModel):
     reactions: list[ReactionSummary]
     created_at: datetime
     edited_at: datetime | None
+    # #53: null for a live message; set once deleted, at which point
+    # content/image_id/file/link_preview are all already cleared
+    # server-side (see message_service.delete_message). `reactions` isn't
+    # cleared server-side -- the frontend just doesn't render them once
+    # deleted_at is set, same as it doesn't render the rest of a tombstone.
+    deleted_at: datetime | None

backend/app/schemas/room.py

@@ -26,6 +26,12 @@ class RoomRead(BaseModel):
     name: str
     description: str | None
     is_private: bool
+    is_dm: bool
+    # #57: previously only exposed on the admin-only AdminRoom schema, so a
+    # member of an archived room had no way to even know it was archived --
+    # the flag was set server-side but had no effect on their own view of
+    # the room at all.
+    is_archived: bool
     owner_id: uuid.UUID
     created_at: datetime
 
@@ -34,6 +40,14 @@ class RoomListItem(RoomRead):
     is_member: bool
 
 
+class DmPartnerInfo(BaseModel):
+    user_id: uuid.UUID
+    username: str
+    display_name: str | None
+    avatar_filename: str | None
+    status: Literal["online", "offline"]
+
+
 class MyRoomItem(RoomRead):
     role: RoomRole
     # Whether this room has a message newer than the caller's last_read_at --
@@ -44,6 +58,25 @@ class MyRoomItem(RoomRead):
     # over has_unread in the sidebar (see RoomRow.tsx), not shown alongside
     # it.
     has_mention: bool
+    # #52: populated only when is_dm is true -- the *other* participant,
+    # precomputed here so the sidebar can render a DM row (their name +
+    # avatar, not this room's internal `name`) without a second fetch per
+    # row. None for a regular room.
+    dm_partner: DmPartnerInfo | None = None
+    # #67: this viewer's own opt-in for email while offline -- the room's
+    # first unread message plus every mention (see message_events.py's
+    # _maybe_email_room_notifications for the exact debounce shape). Always
+    # false for a DM, deliberately out of scope -- DMs already get #66's
+    # automatic offline email.
+    email_notifications: bool = False
+
+
+class StartDmRequest(BaseModel):
+    other_user_id: uuid.UUID
+
+
+class RoomNotificationSettingsUpdate(BaseModel):
+    email_notifications: bool
 
 
 class RoomMemberRead(BaseModel):

backend/app/schemas/session.py

@@ -0,0 +1,20 @@
+import uuid
+from datetime import datetime
+
+from pydantic import BaseModel
+
+
+class SessionRead(BaseModel):
+    id: uuid.UUID
+    ip_address: str | None
+    # Parsed from the stored user_agent by the router (see
+    # user_agent_service.describe_user_agent) -- not a stored column, so a
+    # future improvement to the parser applies retroactively to old rows
+    # too.
+    device_label: str
+    created_at: datetime
+    last_seen_at: datetime
+    # Whether this is the session the request making this call is itself
+    # authenticated with -- lets the UI mark "this device" and treat
+    # revoking it as a self-logout rather than just another row.
+    is_current: bool

backend/app/schemas/user.py

@@ -23,6 +23,8 @@ class UserRead(BaseModel):
     is_site_admin: bool
     display_name: str | None
     theme: str | None
+    text_scale: str | None
+    emoji_scale: str | None
     # Resolved, not just an id -- the frontend needs the actual palette to
     # paint on load without a second round trip (see lib/theme.ts).
     active_custom_theme: CustomThemeRead | None
@@ -57,6 +59,10 @@ class ProfileUpdate(BaseModel):
     # ownership check; that's POST /api/custom-themes/{id}/activate, not a
     # bare theme name with nothing to point it at.
     theme: Literal["dark", "light", "midnight", "sunset"] | None = Field(default=None)
+    # #71: kept in sync with frontend/src/lib/theme.ts's TEXT_SCALE_PERCENT map.
+    text_scale: Literal["small", "normal", "large", "xlarge"] | None = Field(default=None)
+    # #71: kept in sync with MessageContent.tsx's EMOJI_SCALE_MULTIPLIER map.
+    emoji_scale: Literal["small", "normal", "large", "xlarge"] | None = Field(default=None)
     appear_offline: bool | None = Field(default=None)
 
 

backend/app/services/admin_service.py

@@ -93,9 +93,14 @@ async def set_user_site_admin(
 
 
 async def list_rooms_admin(db: AsyncSession) -> list[tuple[Room, int]]:
+    # #52: DMs are fully private, not just unlisted -- excluded here rather
+    # than merely omitted from the response, so there's no admin-portal
+    # surface (this list, or the audit log via anything that touches this
+    # query) that reveals a DM even exists between two users.
     result = await db.execute(
         select(Room, func.count(RoomMembership.user_id))
         .outerjoin(RoomMembership, RoomMembership.room_id == Room.id)
+        .where(Room.is_dm.is_(False))
         .group_by(Room.id)
         .order_by(Room.created_at)
     )

backend/app/services/custom_emoji_service.py

@@ -0,0 +1,80 @@
+import re
+import uuid
+
+from sqlalchemy import select
+from sqlalchemy.exc import IntegrityError
+from sqlalchemy.ext.asyncio import AsyncSession
+
+from app.models import CustomEmoji, User
+from app.storage import delete_file
+
+# Deliberately stricter than the built-in Unicode shortcode set's charset
+# (see frontend/src/lib/emojiShortcodes.ts, which also allows '+') -- this
+# is validating a *new name being chosen*, not matching against an
+# existing fixed list, so there's no reason to allow anything a person
+# wouldn't naturally type. Max 30 chars matches CustomEmoji.shortcode's
+# column width exactly (see that model's comment for why).
+SHORTCODE_PATTERN = re.compile(r"^[a-z0-9_-]{2,30}$")
+
+
+class InvalidShortcodeError(Exception):
+    pass
+
+
+class DuplicateShortcodeError(Exception):
+    pass
+
+
+class CustomEmojiNotFoundError(Exception):
+    pass
+
+
+class NotEmojiOwnerError(Exception):
+    pass
+
+
+async def create_custom_emoji(
+    db: AsyncSession,
+    uploaded_by: uuid.UUID,
+    shortcode: str,
+    storage_filename: str,
+    content_type: str,
+) -> CustomEmoji:
+    if not SHORTCODE_PATTERN.match(shortcode):
+        raise InvalidShortcodeError()
+
+    emoji = CustomEmoji(
+        shortcode=shortcode,
+        storage_filename=storage_filename,
+        content_type=content_type,
+        uploaded_by=uploaded_by,
+    )
+    db.add(emoji)
+    try:
+        await db.commit()
+    except IntegrityError as exc:
+        await db.rollback()
+        raise DuplicateShortcodeError() from exc
+    await db.refresh(emoji)
+    return emoji
+
+
+async def list_custom_emoji(db: AsyncSession) -> list[CustomEmoji]:
+    result = await db.execute(select(CustomEmoji).order_by(CustomEmoji.shortcode))
+    return list(result.scalars().all())
+
+
+async def get_custom_emoji_by_shortcode(db: AsyncSession, shortcode: str) -> CustomEmoji | None:
+    result = await db.execute(select(CustomEmoji).where(CustomEmoji.shortcode == shortcode))
+    return result.scalar_one_or_none()
+
+
+async def delete_custom_emoji(db: AsyncSession, emoji_id: uuid.UUID, current_user: User) -> None:
+    emoji = await db.get(CustomEmoji, emoji_id)
+    if emoji is None:
+        raise CustomEmojiNotFoundError()
+    if emoji.uploaded_by != current_user.id and not current_user.is_site_admin:
+        raise NotEmojiOwnerError()
+    delete_file(emoji.storage_filename)
+    await db.delete(emoji)
+    await db.commit()

backend/app/services/email_service.py

@@ -1,3 +1,4 @@
+import html
 import logging
 from email.message import EmailMessage
 
@@ -5,7 +6,7 @@ import aiosmtplib
 from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.crypto import decrypt
-from app.models import SmtpSettings
+from app.models import CustomTheme, SmtpSettings, User
 from app.services.smtp_settings_service import get_smtp_settings
 
 logger = logging.getLogger(__name__)
@@ -15,14 +16,156 @@ class SmtpNotConfiguredError(Exception):
     pass
 
 
-async def _deliver(cfg: SmtpSettings, to_address: str, subject: str, body: str) -> None:
+# #68: the 6 tokens actually used by the email template below, out of the
+# full ~12-token palette themes.css defines per preset -- an email has no
+# equivalent of --ds-surface-2/--ds-void-2/--ds-highlight/--ds-danger, it's
+# one card on one background with one accent. Kept in sync by hand with
+# frontend/src/styles/tokens.css (the default) and themes.css (the other
+# three presets) -- there's no way to share the source of truth across the
+# Python/CSS boundary, so if either changes the other needs updating too.
+DEFAULT_PALETTE = {
+    "void": "#07080f",
+    "surface": "#101030",
+    "border": "#242478",
+    "text": "#fce4fc",
+    "muted": "#c0ccd8",
+    "accent": "#60d8fc",
+}
+_PRESET_PALETTES: dict[str, dict[str, str]] = {
+    "dark": DEFAULT_PALETTE,
+    "light": {
+        "void": "#f5f3fb",
+        "surface": "#ffffff",
+        "border": "#d8d2ee",
+        "text": "#1a1030",
+        "muted": "#675f80",
+        "accent": "#0891b2",
+    },
+    "midnight": {
+        "void": "#000000",
+        "surface": "#0a0a14",
+        "border": "#262640",
+        "text": "#ffffff",
+        "muted": "#a8b0c0",
+        "accent": "#00f0ff",
+    },
+    "sunset": {
+        "void": "#120a07",
+        "surface": "#241408",
+        "border": "#4a2c14",
+        "text": "#fce8d8",
+        "muted": "#c8b0a0",
+        "accent": "#fca050",
+    },
+}
+
+
+async def _resolve_palette(db: AsyncSession, theme_user: User | None) -> dict[str, str]:
+    """#68: an email addressed to an existing user is styled with *their*
+    selected theme (mirroring the app itself), not a fixed look -- but
+    there's no such thing as "their theme" for someone who doesn't have an
+    account yet (site invites), so theme_user is None there and this falls
+    back to the default DarkSingularity palette, same as a logged-out page.
+    """
+    if theme_user is None or theme_user.theme is None:
+        return DEFAULT_PALETTE
+    if theme_user.theme == "custom":
+        if theme_user.active_custom_theme_id is not None:
+            # A fresh PK fetch, not `theme_user.active_custom_theme` --
+            # that relationship is essentially never eager-loaded by
+            # whatever query got this User row in the first place, and
+            # touching it lazily here would raise MissingGreenlet in
+            # async SQLAlchemy.
+            custom = await db.get(CustomTheme, theme_user.active_custom_theme_id)
+            if custom is not None:
+                colors = custom.colors
+                return {key: colors[key] for key in DEFAULT_PALETTE}
+        return DEFAULT_PALETTE
+    return _PRESET_PALETTES.get(theme_user.theme, DEFAULT_PALETTE)
+
+
+def _render_text(paragraphs: list[str], cta_label: str | None, cta_url: str | None) -> str:
+    body = "\n\n".join(paragraphs)
+    if cta_label and cta_url:
+        body += f"\n\n{cta_label}: {cta_url}"
+    return body
+
+
+def _render_html(
+    palette: dict[str, str],
+    subject: str,
+    paragraphs: list[str],
+    cta_label: str | None,
+    cta_url: str | None,
+) -> str:
+    # Table-based layout with everything inlined -- not the app's own CSS
+    # custom properties (email clients strip <style> blocks and don't
+    # support :root variables), just their resolved hex values baked in
+    # per send. Deliberately plain: one card, one accent color, no imagery
+    # that could get blocked by a client's "show images" gate and leave
+    # the email looking broken instead of just plain.
+    paragraphs_html = "".join(
+        f'<p style="margin:0 0 16px;color:{palette["muted"]};font-size:15px;'
+        f'line-height:1.6;">{html.escape(p)}</p>'
+        for p in paragraphs
+    )
+    cta_html = ""
+    if cta_label and cta_url:
+        cta_html = f"""
+        <table role="presentation" cellpadding="0" cellspacing="0" style="margin:24px 0 4px;">
+          <tr>
+            <td style="border-radius:8px;background:{palette["accent"]};">
+              <a href="{html.escape(cta_url)}" style="display:inline-block;padding:12px 22px;
+                font-size:15px;font-weight:700;color:{palette["void"]};text-decoration:none;
+                border-radius:8px;">{html.escape(cta_label)}</a>
+            </td>
+          </tr>
+        </table>
+        """
+    return f"""<!doctype html>
+<html>
+  <body style="margin:0;padding:0;background:{palette["void"]};">
+    <table role="presentation" width="100%" cellpadding="0" cellspacing="0"
+      style="background:{palette["void"]};padding:32px 16px;">
+      <tr>
+        <td align="center">
+          <table role="presentation" width="480" cellpadding="0" cellspacing="0"
+            style="max-width:480px;width:100%;background:{palette["surface"]};
+            border:1px solid {palette["border"]};border-radius:12px;padding:32px;
+            font-family:-apple-system,BlinkMacSystemFont,'Segoe UI',Helvetica,Arial,sans-serif;">
+            <tr>
+              <td>
+                <div style="font-size:13px;font-weight:800;letter-spacing:0.06em;
+                  text-transform:uppercase;color:{palette["accent"]};margin:0 0 20px;">DS Chat</div>
+                <h1 style="margin:0 0 16px;font-size:20px;font-weight:800;
+                  color:{palette["text"]};">{html.escape(subject)}</h1>
+                {paragraphs_html}
+                {cta_html}
+              </td>
+            </tr>
+          </table>
+        </td>
+      </tr>
+    </table>
+  </body>
+</html>"""
+
+
+async def _deliver(
+    cfg: SmtpSettings, to_address: str, subject: str, html_body: str, text_body: str
+) -> None:
     """Raises on failure -- internal helper only. Callers decide whether to
     swallow (send_email) or surface (send_test_email) the error."""
     message = EmailMessage()
     message["From"] = cfg.from_address
     message["To"] = to_address
     message["Subject"] = subject
-    message.set_content(body)
+    # Plain-text part first, HTML as the alternative -- standard
+    # multipart/alternative ordering (least to most preferred), so a
+    # client with no HTML support (or a spam filter) still gets a normal
+    # readable email instead of raw markup.
+    message.set_content(text_body)
+    message.add_alternative(html_body, subtype="html")
 
     password = decrypt(cfg.password_encrypted) if cfg.password_encrypted else None
 
@@ -55,29 +198,56 @@ async def _deliver(cfg: SmtpSettings, to_address: str, subject: str, body: str)
     )
 
 
-async def send_email(db: AsyncSession, to_address: str, subject: str, body: str) -> None:
+async def send_email(
+    db: AsyncSession,
+    to_address: str,
+    subject: str,
+    paragraphs: list[str],
+    *,
+    cta_label: str | None = None,
+    cta_url: str | None = None,
+    theme_user: User | None = None,
+) -> None:
     """Best-effort -- used by invite/notification flows. Never raises: an
     SMTP outage or missing configuration must never block an action (an
-    invite, a room membership) that already succeeded in the database."""
+    invite, a room membership) that already succeeded in the database.
+
+    `paragraphs` replaces the old flat `body: str` (#68) -- each entry
+    renders as its own paragraph in both the HTML and plain-text parts,
+    which a single pre-formatted string can't cleanly become HTML from
+    without re-parsing it. `theme_user`, when given, styles the email with
+    that user's own selected theme (default palette if they haven't picked
+    one, or don't have an account at all -- see _resolve_palette).
+    """
     cfg = await get_smtp_settings(db)
     if cfg is None:
-        logger.debug("SMTP not configured; skipping email to %s", to_address)
+        # WARNING, not .debug -- this app has no logging config lowering
+        # the root level below Python's own WARNING default, so anything
+        # below that is silently invisible in production (confirmed live:
+        # a real "no emails arriving" report produced nothing in the logs
+        # at all, this line included, even though it was relevant).
+        logger.warning("SMTP not configured; skipping email to %s", to_address)
         return
+    palette = await _resolve_palette(db, theme_user)
+    html_body = _render_html(palette, subject, paragraphs, cta_label, cta_url)
+    text_body = _render_text(paragraphs, cta_label, cta_url)
     try:
-        await _deliver(cfg, to_address, subject, body)
+        await _deliver(cfg, to_address, subject, html_body, text_body)
     except Exception:
         logger.warning("Failed to send email to %s", to_address, exc_info=True)
 
 
-async def send_test_email(db: AsyncSession, to_address: str) -> None:
+async def send_test_email(db: AsyncSession, to_address: str, theme_user: User | None = None) -> None:
     """Used only by the admin 'send test email' button -- raises so the
-    admin UI can show why it failed instead of a silent no-op."""
+    admin UI can show why it failed instead of a silent no-op. theme_user
+    is the admin themselves (see routers/admin.py) -- the preview shows
+    them their own emails' real look, not a generic default."""
     cfg = await get_smtp_settings(db)
     if cfg is None:
         raise SmtpNotConfiguredError()
-    await _deliver(
+    subject = "DS Chat test email"
-        cfg,
+    paragraphs = ["This is a test email from DS Chat to confirm your SMTP settings are working."]
-        to_address,
+    palette = await _resolve_palette(db, theme_user)
-        "DS Chat test email",
+    html_body = _render_html(palette, subject, paragraphs, None, None)
-        "This is a test email from DS Chat to confirm your SMTP settings are working.",
+    text_body = _render_text(paragraphs, None, None)
-    )
+    await _deliver(cfg, to_address, subject, html_body, text_body)

backend/app/services/link_preview_service.py

@@ -27,8 +27,18 @@ _TRAILING_PUNCTUATION = ".,;:!?)'\">"
 _FETCH_TIMEOUT_SECONDS = 5.0
 _MAX_BYTES = 512 * 1024
 _MAX_REDIRECTS = 3
+# #70: was 7 days -- confirmed live as too long for how this app actually
+# gets used: re-posting a URL whose title/content had genuinely changed
+# kept showing the stale first-fetch preview for up to a week. Short
+# enough that it's effectively "always fresh" for any realistic human
+# posting cadence, while still doing the one thing a cache here is
+# actually for -- collapsing a burst of near-simultaneous fetches of the
+# same URL (several people pasting the same link within moments of each
+# other, or the same person's message history being loaded repeatedly)
+# into one, and not hammering a URL that just failed on every message
+# that references it.
 _USER_AGENT = "ds-chat-link-preview/1.0"
-_CACHE_TTL = timedelta(days=7)
+_CACHE_TTL = timedelta(minutes=5)
 
 
 def extract_first_url(content: str | None) -> str | None:

backend/app/services/message_events.py

@@ -1,22 +1,30 @@
 import asyncio
+import logging
 import uuid
 
-from sqlalchemy import select
+from sqlalchemy import select, update
 from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.models import Message, MessageFile, MessageMention, Room, RoomMembership, User
 from app.schemas.message import ReactionSummary
+from app.services.email_service import send_email
 from app.services.link_preview_service import fetch_and_broadcast_link_preview
 from app.services.push_service import send_push_to_user
+from app.services.room_service import list_dm_partner_ids
 from app.services.webhook_service import dispatch_event
 from app.ws.broadcaster import Broadcaster
+from app.ws.focus_presence import FocusPresence
+from app.ws.global_presence import GlobalPresence
 from app.ws.presence import Presence
 
+logger = logging.getLogger(__name__)
+
 
 async def _notify_offline_members(
     db: AsyncSession,
     broadcaster: Broadcaster,
     presence: Presence,
+    focus_presence: FocusPresence,
     room_id: uuid.UUID,
     sender: User,
     message: Message,
@@ -25,12 +33,28 @@ async def _notify_offline_members(
         select(RoomMembership.user_id).where(RoomMembership.room_id == room_id)
     )
     member_ids = {row[0] for row in result.all()}
+    connected_ids = await presence.connected_user_ids(room_id)
     # Subtract the sender explicitly rather than relying on them being
     # "connected" (true for the WS path, since they just sent this over an
     # active connection -- not true for the incoming-webhook REST path,
     # which has no WS connection for the attributed sender at all).
-    offline_ids = member_ids - await presence.connected_user_ids(room_id) - {sender.id}
+    offline_ids = member_ids - connected_ids - {sender.id}
-    if not offline_ids:
+
+    # #59: a desktop-mode member can be *connected* to this room's channel
+    # (it's open on screen, live messages are rendering) while their window
+    # sits unfocused behind something else -- still exactly the situation a
+    # desktop notification should fire for, same as #49's original intent.
+    # This used to be handled by the client faking "offline" (leaving the
+    # room's channel on blur), which also silently stopped live delivery to
+    # that room; FocusPresence is a separate signal so notification
+    # eligibility no longer has to ride on room-connection state at all.
+    connected_but_unfocused_ids = {
+        user_id
+        for user_id in connected_ids - {sender.id}
+        if await focus_presence.is_unfocused(user_id)
+    }
+    notify_ids = offline_ids | connected_but_unfocused_ids
+    if not notify_ids:
         return
 
     result = await db.execute(
@@ -38,12 +62,10 @@ async def _notify_offline_members(
     )
     mentioned_ids = {row[0] for row in result.all()}
 
-    # This is also exactly the right audience for "give this room an unread
+    # Unread-dot audience stays exactly offline_ids, not notify_ids: a
-    # dot": presence.connected_user_ids(room_id) means "has this room's
+    # connected-but-unfocused member still has the room open and rendering
-    # channel joined right now" -- which the client only does while the tab
+    # on screen right now, so it isn't actually "unread" for them the way a
-    # is genuinely foregrounded (see useChatSocket.ts's visibility-gated
+    # room they haven't got open at all is.
-    # join/leave), so a backgrounded-but-open room correctly lands here too,
-    # not just rooms that aren't open at all.
     for user_id in offline_ids:
         await broadcaster.publish_to_user(
             user_id,
@@ -56,7 +78,7 @@ async def _notify_offline_members(
 
     room = await db.get(Room, room_id)
     title = f"#{room.name}" if room else "New message"
-    for user_id in offline_ids:
+    for user_id in notify_ids:
         mentioned = user_id in mentioned_ids
         if message.content:
             prefix = f"{sender.username} mentioned you: " if mentioned else f"{sender.username}: "
@@ -117,6 +139,10 @@ async def _message_payload(db: AsyncSession, message: Message, username: str) ->
         "reactions": [],
         "created_at": message.created_at.isoformat(),
         "edited_at": message.edited_at.isoformat() if message.edited_at else None,
+        # Always null here -- a message just being created can't already be
+        # deleted -- but included for wire-format parity with MessageRead
+        # and message_deleted (#53).
+        "deleted_at": None,
     }
 
 
@@ -127,10 +153,199 @@ def _maybe_fetch_link_preview(broadcaster: Broadcaster, room_id: uuid.UUID, mess
         )
 
 
+async def _maybe_email_dm_notification(
+    db: AsyncSession,
+    global_presence: GlobalPresence,
+    base_url: str,
+    room_id: uuid.UUID,
+    sender: User,
+    message: Message,
+) -> None:
+    """#66: DMs only, deliberately narrower than _notify_offline_members'
+    own "offline" -- that one means "not connected to this room's channel
+    right now," which fires on every message and is fine for a lightweight
+    channel (push/desktop). Email is heavier-weight and a DM's other
+    participant could easily be actively using the app in a different room,
+    so this uses GlobalPresence (genuinely no open connection anywhere)
+    instead -- the same "is this user actually offline" logic as
+    rooms.py's private _member_status (not importable from here), just
+    re-derived.
+    """
+    # #68 follow-up: this whole function used to have zero logging on any
+    # of its early-return paths, which made "why didn't an email go out"
+    # completely undiagnosable from the outside -- confirmed live, a real
+    # report of "no emails" produced nothing in the logs at all, not even
+    # at the level that turned out to be the actual cause. logger.warning
+    # (not .info/.debug) is deliberate: this app has no logging config
+    # setting the root level below Python's own WARNING default, so
+    # anything logged lower than that is silently invisible in production
+    # regardless of what it's actually about -- these aren't really
+    # warnings, they're the only level guaranteed to reach journalctl
+    # today.
+    room = await db.get(Room, room_id)
+    if room is None or not room.is_dm:
+        return
+
+    result = await db.execute(
+        select(RoomMembership).where(
+            RoomMembership.room_id == room_id, RoomMembership.user_id != sender.id
+        )
+    )
+    membership = result.scalar_one_or_none()
+    if membership is None:
+        logger.warning("DM email skipped for room %s: no other participant found", room_id)
+        return
+    recipient = await db.get(User, membership.user_id)
+    if recipient is None:
+        logger.warning(
+            "DM email skipped for room %s: recipient user %s not found", room_id, membership.user_id
+        )
+        return
+    # appear_offline is a manual "always look offline" override -- treated
+    # the same as genuinely offline here, same as everywhere else it's
+    # checked in this codebase.
+    if not recipient.appear_offline and await global_presence.is_online(recipient.id):
+        logger.warning(
+            "DM email skipped for room %s: recipient %s is online", room_id, recipient.id
+        )
+        return
+
+    # Debounced to the first unread message in this conversation, not
+    # every single one -- a burst of DMs while someone's asleep should be
+    # one email, not one per message.
+    already_unread = await db.execute(
+        select(Message.id)
+        .where(
+            Message.room_id == room_id,
+            Message.id != message.id,
+            Message.created_at > membership.last_read_at,
+        )
+        .limit(1)
+    )
+    if already_unread.scalar_one_or_none() is not None:
+        logger.warning(
+            "DM email skipped for room %s: recipient %s already has unread messages",
+            room_id,
+            recipient.id,
+        )
+        return
+
+    if message.content:
+        body_line = f"{sender.username}: {message.content[:200]}"
+    elif message.file_id:
+        body_line = f"{sender.username} sent a file"
+    else:
+        body_line = f"{sender.username} sent an image"
+    link = f"{base_url.rstrip('/')}/rooms/{room_id}"
+    logger.warning("Sending DM email to %s for room %s", recipient.email, room_id)
+    await send_email(
+        db,
+        recipient.email,
+        f"New message from {sender.username}",
+        [body_line],
+        cta_label="Open conversation",
+        cta_url=link,
+        theme_user=recipient,
+    )
+
+
+async def _maybe_email_room_notifications(
+    db: AsyncSession,
+    global_presence: GlobalPresence,
+    base_url: str,
+    room_id: uuid.UUID,
+    sender: User,
+    message: Message,
+) -> None:
+    """#67: opt-in, per-room email -- deliberately scoped to regular rooms
+    only (see set_room_email_notifications: DMs already get #66's
+    always-on offline email, no separate toggle).
+
+    Two triggers, not one: the room's first unread message debounces the
+    same way #66 does (one email per unread burst, not one per message),
+    but a mention always emails regardless of that debounce -- a mention
+    is a stronger, individually-addressed signal that shouldn't get
+    silently swallowed just because an earlier plain message in the same
+    burst already used up the "first unread" email.
+    """
+    room = await db.get(Room, room_id)
+    if room is None or room.is_dm:
+        return
+
+    result = await db.execute(
+        select(MessageMention.user_id).where(MessageMention.message_id == message.id)
+    )
+    mentioned_ids = {row[0] for row in result.all()}
+
+    result = await db.execute(
+        select(RoomMembership).where(
+            RoomMembership.room_id == room_id,
+            RoomMembership.user_id != sender.id,
+            RoomMembership.email_notifications.is_(True),
+        )
+    )
+    subscribed_memberships = result.scalars().all()
+    if not subscribed_memberships:
+        return
+
+    for membership in subscribed_memberships:
+        user_id = membership.user_id
+        recipient = await db.get(User, user_id)
+        if recipient is None:
+            continue
+        # appear_offline always wins here too, same as _maybe_email_dm_notification.
+        if not recipient.appear_offline and await global_presence.is_online(recipient.id):
+            continue
+
+        mentioned = user_id in mentioned_ids
+        if not mentioned:
+            already_unread = await db.execute(
+                select(Message.id)
+                .where(
+                    Message.room_id == room_id,
+                    Message.id != message.id,
+                    Message.created_at > membership.last_read_at,
+                )
+                .limit(1)
+            )
+            if already_unread.scalar_one_or_none() is not None:
+                continue
+
+        if mentioned:
+            subject = f"New mention in #{room.name}"
+            body_line = (
+                f"{sender.username} mentioned you: {message.content[:200]}"
+                if message.content
+                else f"{sender.username} mentioned you"
+            )
+        else:
+            subject = f"New message in #{room.name}"
+            if message.content:
+                body_line = f"{sender.username}: {message.content[:200]}"
+            elif message.file_id:
+                body_line = f"{sender.username} sent a file"
+            else:
+                body_line = f"{sender.username} sent an image"
+
+        link = f"{base_url.rstrip('/')}/rooms/{room_id}"
+        await send_email(
+            db,
+            recipient.email,
+            subject,
+            [body_line],
+            cta_label="Open room",
+            cta_url=link,
+            theme_user=recipient,
+        )
+
+
 async def broadcast_new_message(
     db: AsyncSession,
     broadcaster: Broadcaster,
     presence: Presence,
+    focus_presence: FocusPresence,
+    global_presence: GlobalPresence,
+    base_url: str,
     room_id: uuid.UUID,
     message: Message,
     sender: User,
@@ -140,7 +355,30 @@ async def broadcast_new_message(
     trigger identical fan-out/push/event behavior."""
     payload = await _message_payload(db, message, sender.username)
     await broadcaster.publish(room_id, payload)
-    await _notify_offline_members(db, broadcaster, presence, room_id, sender, message)
+    # A no-op for a regular room (hidden_at is only ever set on a DM's
+    # membership row -- see RoomMembership.hidden_at) -- new activity
+    # un-hiding a DM someone closed matches find_or_create_dm's own
+    # un-hide-on-reopen behavior. `.returning` so we know exactly who was
+    # un-hidden -- their client needs the same room_added signal a brand
+    # new DM does (see broadcast_room_added's docstring): the room wasn't
+    # in their already-loaded room list at all, so unread_update's plain
+    # setRooms(prev => prev.map(...)) can't make it reappear -- there's
+    # nothing in `prev` for it to match.
+    unhidden_result = await db.execute(
+        update(RoomMembership)
+        .where(RoomMembership.room_id == room_id, RoomMembership.hidden_at.is_not(None))
+        .values(hidden_at=None)
+        .returning(RoomMembership.user_id)
+    )
+    unhidden_user_ids = list(unhidden_result.scalars().all())
+    await db.commit()
+    for unhidden_user_id in unhidden_user_ids:
+        await broadcaster.publish_to_user(
+            unhidden_user_id, {"type": "room_added", "room_id": str(room_id)}
+        )
+    await _notify_offline_members(db, broadcaster, presence, focus_presence, room_id, sender, message)
+    await _maybe_email_dm_notification(db, global_presence, base_url, room_id, sender, message)
+    await _maybe_email_room_notifications(db, global_presence, base_url, room_id, sender, message)
     await dispatch_event(db, "message.created", room_id, payload)
     _maybe_fetch_link_preview(broadcaster, room_id, message)
 
@@ -165,6 +403,16 @@ async def broadcast_message_update(
     _maybe_fetch_link_preview(broadcaster, room_id, message)
 
 
+async def broadcast_message_delete(broadcaster: Broadcaster, room_id: uuid.UUID, message_id: uuid.UUID) -> None:
+    # #53: no dispatch_event() call, deliberately -- same scope cut as
+    # broadcast_reaction_update's, and for the same reason (see
+    # backend/README.md): message.deleted isn't an outgoing-webhook event
+    # type here.
+    await broadcaster.publish(
+        room_id, {"type": "message_deleted", "id": str(message_id), "room_id": str(room_id)}
+    )
+
+
 async def broadcast_reaction_update(
     broadcaster: Broadcaster,
     room_id: uuid.UUID,
@@ -199,6 +447,29 @@ async def broadcast_member_updated(db: AsyncSession, broadcaster: Broadcaster, u
         )
 
 
+async def broadcast_dm_presence_update(
+    db: AsyncSession, broadcaster: Broadcaster, user_id: uuid.UUID, online: bool
+) -> None:
+    """Tells every one of user_id's DM partners that their online/offline
+    status just changed (#63) -- on each partner's own per-user channel,
+    not the DM room's channel. The room channel alone doesn't reach the
+    sidebar: Presence gates room-channel delivery on actually having that
+    specific room's channel joined right now, which is only ever the one
+    room currently open in the UI -- so a DM sitting unopened in the
+    sidebar (which is the normal case; the sidebar shows every DM's status
+    at once) never saw its partner's status change until something else
+    forced a full room-list refetch."""
+    for partner_id in await list_dm_partner_ids(db, user_id):
+        await broadcaster.publish_to_user(
+            partner_id,
+            {
+                "type": "dm_presence_update",
+                "user_id": str(user_id),
+                "status": "online" if online else "offline",
+            },
+        )
+
+
 async def broadcast_room_added(broadcaster: Broadcaster, user_id: uuid.UUID, room: Room) -> None:
     """The only signal a user's open client gets that they were just added
     to a room -- without it, GET /rooms/mine is only ever fetched once at

backend/app/services/message_service.py

@@ -6,11 +6,19 @@ from sqlalchemy import or_, select
 from sqlalchemy.ext.asyncio import AsyncSession
 from sqlalchemy.orm import selectinload
 
-from app.models import Message, MessageMention, MessageReaction, MessageRoomReference
+from app.models import (
+    Message,
+    MessageFile,
+    MessageImage,
+    MessageMention,
+    MessageReaction,
+    MessageRoomReference,
+)
 from app.schemas.message import ReactionSummary
 from app.services.link_preview_service import extract_first_url
 from app.services.mention_service import extract_mentioned_user_ids
 from app.services.room_reference_service import extract_referenced_room_ids
+from app.storage import delete_file
 
 
 class MessageNotFoundError(Exception):
@@ -56,7 +64,9 @@ async def edit_message(
     db: AsyncSession, message_id: uuid.UUID, editor_id: uuid.UUID, content: str
 ) -> Message:
     message = await db.get(Message, message_id)
-    if message is None:
+    # A deleted message might as well not exist for editing purposes --
+    # same MessageNotFoundError a genuinely missing id would raise.
+    if message is None or message.deleted_at is not None:
         raise MessageNotFoundError()
     if message.user_id != editor_id:
         raise NotMessageAuthorError()
@@ -69,6 +79,50 @@ async def edit_message(
     return message
 
 
+async def delete_message(db: AsyncSession, message_id: uuid.UUID, deleter_id: uuid.UUID) -> Message:
+    message = await db.get(Message, message_id)
+    if message is None or message.deleted_at is not None:
+        raise MessageNotFoundError()
+    if message.user_id != deleter_id:
+        raise NotMessageAuthorError()
+
+    # Fetch the attachment's storage filename (if any) before clearing the
+    # message's own FK to it -- the file is only unlinked from disk after a
+    # successful commit below, mirroring delete_room's identical ordering:
+    # a rolled-back transaction should never leave us having destroyed
+    # something we couldn't get back.
+    image_filename: str | None = None
+    file_filename: str | None = None
+    if message.image_id is not None:
+        image = await db.get(MessageImage, message.image_id)
+        if image is not None:
+            image_filename = image.storage_filename
+            await db.delete(image)
+    if message.file_id is not None:
+        message_file = await db.get(MessageFile, message.file_id)
+        if message_file is not None:
+            file_filename = message_file.storage_filename
+            await db.delete(message_file)
+
+    # #53: a real delete, not just a UI hide -- content and any attachment
+    # are actually gone, not merely unlinked-but-still-fetchable. Only
+    # deleted_at (plus id/room_id/user_id/created_at, kept so the tombstone
+    # still occupies its place in history) survives.
+    message.content = None
+    message.image_id = None
+    message.file_id = None
+    message.preview_url = None
+    message.deleted_at = datetime.now(timezone.utc)
+    await db.commit()
+    await db.refresh(message)
+
+    for filename in (image_filename, file_filename):
+        if filename is not None:
+            delete_file(filename)
+
+    return message
+
+
 async def list_recent_messages(
     db: AsyncSession, room_id: uuid.UUID, limit: int = 50
 ) -> list[Message]:

backend/app/services/password_service.py

@@ -46,10 +46,13 @@ async def request_password_reset(db: AsyncSession, email: str, base_url: str) ->
         db,
         email,
         "Reset your DS Chat password",
-        f"Someone requested a password reset for this account.\n\n"
+        [
-        f"Reset it here:\n{reset_link}\n\n"
+            "Someone requested a password reset for this account.",
-        f"This link expires in 15 minutes. If you didn't request this, "
+            "This link expires in 15 minutes. If you didn't request this, you can ignore this email.",
-        f"you can ignore this email.",
+        ],
+        cta_label="Reset password",
+        cta_url=reset_link,
+        theme_user=user,
     )
 
 

backend/app/services/push_service.py

@@ -2,6 +2,7 @@ import asyncio
 import json
 import logging
 import uuid
+from urllib.parse import urlparse
 
 from pywebpush import WebPushException, webpush
 from sqlalchemy import delete, select
@@ -53,7 +54,23 @@ async def unsubscribe(db: AsyncSession, user_id: uuid.UUID, endpoint: str) -> No
     await db.commit()
 
 
+# #56 correction: bumping to pywebpush's latest release (2.4.0) turned out
+# not to actually fix WNS -- checked the installed package's own source
+# directly and it has no WNS-specific code anywhere; the upstream
+# discussion (web-push-libs/pywebpush#162) apparently never shipped.
+# Worked around here instead, using the `headers` param webpush() already
+# exposes for exactly this: WNS (Windows/Edge push,
+# *.notify.windows.com) has required this header since April 2024, or it
+# 400s with no useful body -- "cache" for a non-zero TTL, "no-cache" for
+# zero (this app never sets a TTL, so always the latter).
+def _is_wns_endpoint(endpoint: str) -> bool:
+    return urlparse(endpoint).hostname is not None and urlparse(endpoint).hostname.endswith(
+        "notify.windows.com"
+    )
+
+
 def _send_one(subscription: PushSubscription, payload: dict) -> None:
+    extra_headers = {"X-WNS-Cache-Policy": "no-cache"} if _is_wns_endpoint(subscription.endpoint) else None
     webpush(
         subscription_info={
             "endpoint": subscription.endpoint,
@@ -62,6 +79,7 @@ def _send_one(subscription: PushSubscription, payload: dict) -> None:
         data=json.dumps(payload),
         vapid_private_key=settings.vapid_private_key,
         vapid_claims={"sub": settings.vapid_subject},
+        headers=extra_headers,
     )
 
 
@@ -95,4 +113,17 @@ async def send_push_to_user(db: AsyncSession, user_id: uuid.UUID, payload: dict)
                 )
                 await db.commit()
             else:
-                logger.warning("Push delivery failed for %s: %s", subscription.id, exc)
+                # #56: WNS's own 400s carry the actual reason in a response
+                # *header* ("Ttl value conflicts with X-WNS-Cache-Policy"),
+                # not the body -- pywebpush's own exception message only
+                # ever surfaces the body, so that specific bug still would
+                # have needed a full journalctl+DB-dump investigation to
+                # diagnose even with a body-only log line. Logging headers
+                # too is the difference between "something is broken" and
+                # this log line alone being enough next time, for any push
+                # provider's failure, not just WNS's.
+                response = exc.response
+                detail = ""
+                if response is not None:
+                    detail = f" | response: {response.text!r} | headers: {dict(response.headers)!r}"
+                logger.warning("Push delivery failed for %s: %s%s", subscription.id, exc, detail)

backend/app/services/room_service.py

@@ -1,13 +1,27 @@
 import uuid
 
-from sqlalchemy import delete, func, select
+from sqlalchemy import delete, func, or_, select
 from sqlalchemy.exc import IntegrityError
 from sqlalchemy.ext.asyncio import AsyncSession
 from sqlalchemy.orm import selectinload
 
-from app.models import Message, MessageMention, Room, RoomMembership, RoomRole, User
+from app.models import (
+    EventSubscription,
+    Message,
+    MessageFile,
+    MessageImage,
+    MessageMention,
+    MessageReaction,
+    MessageRoomReference,
+    Room,
+    RoomMembership,
+    RoomRole,
+    User,
+    WebhookIncoming,
+)
 from app.schemas.room import RoomCreate, RoomUpdate
 from app.services.email_service import send_email
+from app.storage import delete_file
 
 
 class DuplicateRoomError(Exception):
@@ -46,6 +60,50 @@ class AlreadyMemberError(Exception):
     pass
 
 
+class CannotDmSelfError(Exception):
+    pass
+
+
+class CannotModifyDmError(Exception):
+    pass
+
+
+class NotADmError(Exception):
+    pass
+
+
+def dm_room_name(user_a_id: uuid.UUID, user_b_id: uuid.UUID) -> str:
+    """Deterministic, internal-only name for the DM room between these two
+    users -- same canonical string regardless of argument order, so
+    find_or_create_dm can look up an existing DM with a single indexed
+    query (Room.name is already unique+indexed) instead of a membership-set
+    join. Never shown to a user -- the frontend renders a DM's dm_partner
+    info instead of its `name` (see MyRoomItem)."""
+    ids = sorted((str(user_a_id), str(user_b_id)))
+    return f"dm:{ids[0]}:{ids[1]}"
+
+
+async def _unhide(db: AsyncSession, room_id: uuid.UUID, user_id: uuid.UUID) -> None:
+    membership = (
+        await db.execute(
+            select(RoomMembership).where(
+                RoomMembership.room_id == room_id, RoomMembership.user_id == user_id
+            )
+        )
+    ).scalar_one_or_none()
+    if membership is not None and membership.hidden_at is not None:
+        membership.hidden_at = None
+        await db.commit()
+
+
+async def hide_dm(db: AsyncSession, room: Room, user_id: uuid.UUID) -> None:
+    if not room.is_dm:
+        raise NotADmError()
+    membership = await _get_membership(db, room.id, user_id)
+    membership.hidden_at = func.now()
+    await db.commit()
+
+
 async def create_room(db: AsyncSession, owner_id: uuid.UUID, data: RoomCreate) -> Room:
     room = Room(
         name=data.name,
@@ -66,10 +124,53 @@ async def create_room(db: AsyncSession, owner_id: uuid.UUID, data: RoomCreate) -
     return room
 
 
+async def find_or_create_dm(db: AsyncSession, user_id: uuid.UUID, other_user_id: uuid.UUID) -> Room:
+    if user_id == other_user_id:
+        raise CannotDmSelfError()
+    other = await db.get(User, other_user_id)
+    if other is None:
+        raise TargetUserNotFoundError()
+
+    name = dm_room_name(user_id, other_user_id)
+    result = await db.execute(select(Room).where(Room.name == name))
+    room = result.scalar_one_or_none()
+    if room is not None:
+        await _unhide(db, room.id, user_id)
+        return room
+
+    # is_private=True is belt-and-suspenders here -- list_open_rooms also
+    # excludes is_dm directly -- but it's also just semantically correct: a
+    # DM genuinely is a private room. Both participants get the plain
+    # `member` role (there's no meaningful owner/admin distinction for a
+    # 1:1 DM); `owner_id` still has to be someone to satisfy the column,
+    # but nothing reads it as meaningful for a DM.
+    room = Room(name=name, is_private=True, is_dm=True, owner_id=user_id)
+    db.add(room)
+    try:
+        await db.flush()
+    except IntegrityError:
+        # Lost a race with a concurrent find_or_create_dm for the same pair
+        # (e.g. both people click "message" on each other at once) -- the
+        # unique constraint on `name` is exactly what caught it, same
+        # pattern as create_room's DuplicateRoomError. The row that won the
+        # race is the room we actually want.
+        await db.rollback()
+        result = await db.execute(select(Room).where(Room.name == name))
+        room = result.scalar_one()
+        await _unhide(db, room.id, user_id)
+        return room
+
+    db.add(RoomMembership(room_id=room.id, user_id=user_id, role=RoomRole.member))
+    db.add(RoomMembership(room_id=room.id, user_id=other_user_id, role=RoomRole.member))
+    await db.commit()
+    await db.refresh(room)
+    return room
+
+
 async def list_open_rooms(db: AsyncSession, user_id: uuid.UUID) -> list[tuple[Room, bool]]:
     result = await db.execute(
         select(Room)
-        .where(Room.is_private.is_(False), Room.is_archived.is_(False))
+        .where(Room.is_private.is_(False), Room.is_archived.is_(False), Room.is_dm.is_(False))
         .options(selectinload(Room.memberships))
         .order_by(Room.created_at, Room.id)
     )
@@ -81,7 +182,7 @@ async def list_open_rooms(db: AsyncSession, user_id: uuid.UUID) -> list[tuple[Ro
 
 async def list_member_rooms(
     db: AsyncSession, user_id: uuid.UUID
-) -> list[tuple[Room, RoomRole, bool, bool]]:
+) -> list[tuple[Room, RoomRole, bool, bool, bool, User | None]]:
     last_message_at = (
         select(func.max(Message.created_at))
         .where(Message.room_id == Room.id)
@@ -104,10 +205,15 @@ async def list_member_rooms(
     )
     result = await db.execute(
         select(
-            Room, RoomMembership.role, RoomMembership.last_read_at, last_message_at, has_unread_mention
+            Room,
+            RoomMembership.role,
+            RoomMembership.last_read_at,
+            last_message_at,
+            has_unread_mention,
+            RoomMembership.email_notifications,
         )
         .join(RoomMembership, RoomMembership.room_id == Room.id)
-        .where(RoomMembership.user_id == user_id)
+        .where(RoomMembership.user_id == user_id, RoomMembership.hidden_at.is_(None))
         # A secondary key on the primary key -- without it, Postgres has no
         # obligation to return two same-instant rooms (a plausible tie:
         # bulk-created/migrated rooms, or just two created in quick
@@ -116,12 +222,55 @@ async def list_member_rooms(
         # device's fetch and another's.
         .order_by(Room.created_at, Room.id)
     )
+    rows = result.all()
+
+    # #52: one batched follow-up query for every DM room's *other*
+    # participant, rather than a fetch per row -- a DM only ever has
+    # exactly two members, so "the other one" is unambiguous.
+    dm_room_ids = [room.id for room, *_ in rows if room.is_dm]
+    partners_by_room: dict[uuid.UUID, User] = {}
+    if dm_room_ids:
+        partner_result = await db.execute(
+            select(RoomMembership.room_id, User)
+            .join(User, User.id == RoomMembership.user_id)
+            .where(RoomMembership.room_id.in_(dm_room_ids), RoomMembership.user_id != user_id)
+        )
+        partners_by_room = {room_id: user for room_id, user in partner_result.all()}
+
     return [
-        (room, role, last_message_at is not None and last_message_at > last_read_at, has_mention)
+        (
-        for room, role, last_read_at, last_message_at, has_mention in result.all()
+            room,
+            role,
+            last_message_at is not None and last_message_at > last_read_at,
+            has_mention,
+            email_notifications,
+            partners_by_room.get(room.id),
+        )
+        for room, role, last_read_at, last_message_at, has_mention, email_notifications in rows
     ]
 
 
+async def list_dm_partner_ids(db: AsyncSession, user_id: uuid.UUID) -> list[uuid.UUID]:
+    """Every user this user_id shares a DM with (#63) -- used to know who
+    needs telling about a global online/offline transition, since Presence
+    gates room-channel delivery on actually having that specific room
+    joined right now (only ever the one room currently open in the UI), so
+    a DM sitting unopened in the sidebar would otherwise never hear about
+    its partner's status changing at all."""
+    result = await db.execute(
+        select(RoomMembership.user_id)
+        .join(Room, Room.id == RoomMembership.room_id)
+        .where(
+            Room.is_dm.is_(True),
+            RoomMembership.user_id != user_id,
+            RoomMembership.room_id.in_(
+                select(RoomMembership.room_id).where(RoomMembership.user_id == user_id)
+            ),
+        )
+    )
+    return [row[0] for row in result.all()]
+
+
 async def get_room(db: AsyncSession, room_id: uuid.UUID) -> Room:
     room = await db.get(Room, room_id)
     if room is None:
@@ -173,8 +322,10 @@ async def add_member(
         db,
         target.email,
         f"You've been added to #{room.name}",
-        f"You've been added to the #{room.name} room on DS Chat.\n\n"
+        [f"You've been added to the #{room.name} room on DS Chat."],
-        f"Open the app: {base_url.rstrip('/')}",
+        cta_label="Open DS Chat",
+        cta_url=base_url.rstrip("/"),
+        theme_user=target,
     )
 
     result = await db.execute(
@@ -186,6 +337,14 @@ async def add_member(
 
 
 async def update_room(db: AsyncSession, room: Room, data: RoomUpdate) -> Room:
+    # A DM's `name` is an internal token find_or_create_dm's lookup depends
+    # on being stable -- renaming it (even via the #48 site-admin bypass in
+    # the router) would silently orphan that invariant, not just leak a
+    # detail that's supposed to stay private. Blocked here, not just in the
+    # UI, since it's a correctness issue for every caller, not a permission
+    # one.
+    if room.is_dm:
+        raise CannotModifyDmError()
     if data.name is not None:
         room.name = data.name
     if data.description is not None:
@@ -203,12 +362,60 @@ async def update_room(db: AsyncSession, room: Room, data: RoomUpdate) -> Room:
 
 async def delete_room(db: AsyncSession, room: Room) -> None:
     # Explicit deletes rather than relying on ORM cascade + eager-loading —
-    # simpler and more predictable in async code.
+    # simpler and more predictable in async code. None of these FKs are
+    # declared ON DELETE CASCADE at the DB level (confirmed across every
+    # migration that added one), so every table referencing this room --
+    # directly, or indirectly via one of its messages -- has to be cleared
+    # explicitly, in dependency order, or the final room delete 500s on
+    # whichever one it happens to hit first (originally surfaced as a
+    # message_room_references FK violation, but every table below has the
+    # exact same gap).
+    room_message_ids = select(Message.id).where(Message.room_id == room.id).scalar_subquery()
+
+    # Message-child tables first -- these reference message_id, so they'd
+    # block deleting this room's own messages otherwise.
+    await db.execute(delete(MessageMention).where(MessageMention.message_id.in_(room_message_ids)))
+    await db.execute(delete(MessageReaction).where(MessageReaction.message_id.in_(room_message_ids)))
+    # Both directions: a reference *from* one of this room's own messages,
+    # and a reference *to* this room from a message in a completely
+    # different room (the case that originally surfaced this bug).
+    await db.execute(
+        delete(MessageRoomReference).where(
+            or_(
+                MessageRoomReference.message_id.in_(room_message_ids),
+                MessageRoomReference.room_id == room.id,
+            )
+        )
+    )
+
+    # Fetch attachment storage filenames before deleting their rows -- the
+    # actual files are only unlinked after a successful commit below, so a
+    # rolled-back transaction never leaves us having destroyed something we
+    # couldn't get back.
+    image_filenames = (
+        await db.execute(select(MessageImage.storage_filename).where(MessageImage.room_id == room.id))
+    ).scalars().all()
+    file_filenames = (
+        await db.execute(select(MessageFile.storage_filename).where(MessageFile.room_id == room.id))
+    ).scalars().all()
+
+    # Messages themselves, now that nothing still references them.
     await db.execute(delete(Message).where(Message.room_id == room.id))
+
+    # Room-scoped attachments/integrations -- messages.image_id/file_id
+    # reference these, so they must come after the message delete above.
+    await db.execute(delete(MessageImage).where(MessageImage.room_id == room.id))
+    await db.execute(delete(MessageFile).where(MessageFile.room_id == room.id))
+    await db.execute(delete(WebhookIncoming).where(WebhookIncoming.room_id == room.id))
+    await db.execute(delete(EventSubscription).where(EventSubscription.room_id == room.id))
+
     await db.execute(delete(RoomMembership).where(RoomMembership.room_id == room.id))
     await db.delete(room)
     await db.commit()
 
+    for filename in (*image_filenames, *file_filenames):
+        delete_file(filename)
+
 
 async def list_room_members(db: AsyncSession, room_id: uuid.UUID) -> list[RoomMembership]:
     result = await db.execute(
@@ -285,6 +492,22 @@ async def mark_room_read(db: AsyncSession, room_id: uuid.UUID, user_id: uuid.UUI
     await db.commit()
 
 
+async def set_room_email_notifications(
+    db: AsyncSession, room_id: uuid.UUID, user_id: uuid.UUID, enabled: bool
+) -> None:
+    """#67: DMs are deliberately excluded -- they already get #66's
+    automatic offline email with no opt-in needed, and this setting only
+    makes sense for a regular room's mention-based notifications."""
+    room = await db.get(Room, room_id)
+    if room is None:
+        raise RoomNotFoundError()
+    if room.is_dm:
+        raise CannotModifyDmError()
+    membership = await _get_membership(db, room_id, user_id)
+    membership.email_notifications = enabled
+    await db.commit()
+
+
 async def leave_room(db: AsyncSession, room_id: uuid.UUID, user_id: uuid.UUID) -> None:
     membership = await _get_membership(db, room_id, user_id)
     if membership.role == RoomRole.owner:

backend/app/services/session_service.py

@@ -0,0 +1,100 @@
+import uuid
+from datetime import datetime, timedelta, timezone
+
+from fastapi import Request
+from sqlalchemy import select
+from sqlalchemy.ext.asyncio import AsyncSession
+
+from app.models import Session
+
+# #69: how stale last_seen_at has to be before a request bothers updating
+# it. get_current_user resolves a session on *every* authenticated
+# request (dozens per minute per active browser tab, between message
+# polling, presence, etc.) -- writing+committing on every single one would
+# turn a read into a write storm for no real benefit, since "active
+# sessions" only needs last-seen accurate to within a few minutes, not to
+# the second.
+LAST_SEEN_THROTTLE = timedelta(minutes=5)
+
+
+class SessionNotFoundError(Exception):
+    pass
+
+
+def get_client_ip(request_or_websocket) -> str | None:
+    # X-Forwarded-For's first entry is the original client -- everything
+    # after it was appended by intermediate proxies. Production runs
+    # behind Nginx Proxy Manager (see backend/README.md's "Admin portal"
+    # section preamble), which sets this; local dev has nothing in front
+    # of the app, so this falls back to the direct peer address.
+    forwarded = request_or_websocket.headers.get("x-forwarded-for")
+    if forwarded:
+        return forwarded.split(",")[0].strip()
+    client = request_or_websocket.client
+    return client.host if client else None
+
+
+async def create_session(
+    db: AsyncSession, user_id: uuid.UUID, ip_address: str | None, user_agent: str | None
+) -> Session:
+    session = Session(user_id=user_id, ip_address=ip_address, user_agent=user_agent)
+    db.add(session)
+    await db.commit()
+    await db.refresh(session)
+    return session
+
+
+async def start_session(request: Request, db: AsyncSession, user_id: uuid.UUID) -> Session:
+    """Every "log this browser in" call site (login, reset-password
+    completion, signup completion) needs the exact same three steps --
+    read the request's IP/UA, create the row, stash its id in the signed
+    cookie -- so this is the one place that combination lives."""
+    session = await create_session(db, user_id, get_client_ip(request), request.headers.get("user-agent"))
+    request.session["session_id"] = str(session.id)
+    return session
+
+
+async def resolve_session(db: AsyncSession, session_id: uuid.UUID) -> Session | None:
+    """Returns the session iff it exists and hasn't been revoked -- the
+    single choke point get_current_user and the WS handshake both go
+    through, so revoking a session (this endpoint or another device's
+    "sign out") takes effect on that session's very next request rather
+    than only once its signed cookie happens to expire."""
+    session = await db.get(Session, session_id)
+    if session is None or session.revoked_at is not None:
+        return None
+
+    now = datetime.now(timezone.utc)
+    if now - session.last_seen_at > LAST_SEEN_THROTTLE:
+        session.last_seen_at = now
+        await db.commit()
+    return session
+
+
+async def list_sessions(db: AsyncSession, user_id: uuid.UUID) -> list[Session]:
+    result = await db.execute(
+        select(Session)
+        .where(Session.user_id == user_id, Session.revoked_at.is_(None))
+        .order_by(Session.last_seen_at.desc())
+    )
+    return list(result.scalars().all())
+
+
+async def revoke_session(db: AsyncSession, user_id: uuid.UUID, session_id: uuid.UUID) -> None:
+    session = await db.get(Session, session_id)
+    if session is None or session.user_id != user_id or session.revoked_at is not None:
+        raise SessionNotFoundError()
+    session.revoked_at = datetime.now(timezone.utc)
+    await db.commit()
+
+
+async def revoke_session_unchecked(db: AsyncSession, session_id: uuid.UUID) -> None:
+    """Logout's own path -- no ownership check needed (a session can only
+    ever log itself out) and silently does nothing for a session that's
+    missing or already revoked, since "sign this browser out" should
+    never itself fail."""
+    session = await db.get(Session, session_id)
+    if session is None or session.revoked_at is not None:
+        return
+    session.revoked_at = datetime.now(timezone.utc)
+    await db.commit()

backend/app/services/site_invite_service.py

@@ -7,6 +7,7 @@ from sqlalchemy.ext.asyncio import AsyncSession
 from sqlalchemy.orm import selectinload
 
 from app.models import InviteStatus, SiteInvite, User
+from app.models.site_invite import DEFAULT_SITE_INVITE_LIFETIME
 from app.schemas.user import UserCreate
 from app.security import hash_token
 from app.services.audit import record_audit_log
@@ -26,6 +27,24 @@ class SiteInviteInvalidError(Exception):
     pass
 
 
+async def _send_invite_email(db: AsyncSession, inviter_username: str, base_url: str, email: str, raw_token: str) -> None:
+    signup_link = f"{base_url.rstrip('/')}/signup?token={raw_token}"
+    # No theme_user -- the invitee doesn't have an account yet, so there's
+    # no theme of theirs to use (#68). Default palette, same as any
+    # logged-out page.
+    await send_email(
+        db,
+        email,
+        "You're invited to join DS Chat",
+        [
+            f"You've been invited to join DS Chat by {inviter_username}.",
+            "This link expires in 7 days.",
+        ],
+        cta_label="Set up your account",
+        cta_url=signup_link,
+    )
+
+
 async def create_site_invite(
     db: AsyncSession, actor: User, base_url: str, email: str
 ) -> SiteInvite:
@@ -39,21 +58,19 @@ async def create_site_invite(
     await db.commit()
     await db.refresh(invite)
 
-    signup_link = f"{base_url.rstrip('/')}/signup?token={raw_token}"
+    await _send_invite_email(db, actor.username, base_url, email, raw_token)
-    await send_email(
-        db,
-        email,
-        "You're invited to join DS Chat",
-        f"You've been invited to join DS Chat by {actor.username}.\n\n"
-        f"Set up your account here:\n{signup_link}\n\n"
-        f"This link expires in 7 days.",
-    )
     return invite
 
 
 async def list_site_invites(db: AsyncSession) -> list[SiteInvite]:
+    # Pending only (#61) -- the admin UI's only consumer of this list labels
+    # it "Pending invites" and had no way to drop a row once it was accepted
+    # or revoked, since the backend returned every invite ever sent forever.
+    # An accepted/revoked invite has nothing further to act on here; its
+    # history already lives in the audit log ("user.invite"/"invite.revoke").
     result = await db.execute(
         select(SiteInvite)
+        .where(SiteInvite.status == InviteStatus.pending)
         .options(selectinload(SiteInvite.inviter))
         .order_by(SiteInvite.created_at.desc())
     )
@@ -74,6 +91,31 @@ async def revoke_site_invite(db: AsyncSession, actor: User, invite_id: uuid.UUID
     return invite
 
 
+async def resend_site_invite(
+    db: AsyncSession, actor: User, base_url: str, invite_id: uuid.UUID
+) -> SiteInvite:
+    invite = await db.get(SiteInvite, invite_id)
+    if invite is None:
+        raise SiteInviteNotFoundError()
+    if invite.status != InviteStatus.pending:
+        raise SiteInviteNotPendingError()
+
+    # A fresh token and a reset 7-day expiry, not just re-sending the same
+    # link -- the old link stops working the moment this runs (same
+    # "rotate, don't just repeat" instinct as a password-reset resend), and
+    # it means resending something close to expiring actually buys the
+    # full week again instead of whatever was left.
+    raw_token = secrets.token_urlsafe(32)
+    invite.token_hash = hash_token(raw_token)
+    invite.expires_at = datetime.now(timezone.utc) + DEFAULT_SITE_INVITE_LIFETIME
+    record_audit_log(db, actor, "invite.resend", "invite", invite.id, {"email": invite.email})
+    await db.commit()
+    await db.refresh(invite)
+
+    await _send_invite_email(db, actor.username, base_url, invite.email, raw_token)
+    return invite
+
+
 async def _get_pending_invite_by_token(db: AsyncSession, token: str) -> SiteInvite:
     result = await db.execute(
         select(SiteInvite).where(SiteInvite.token_hash == hash_token(token))

backend/app/services/system_user_service.py

@@ -0,0 +1,45 @@
+from sqlalchemy import select
+from sqlalchemy.exc import IntegrityError
+from sqlalchemy.ext.asyncio import AsyncSession
+
+from app.models import User
+from app.security import generate_token, hash_password
+
+# #74: one well-known, auto-provisioned bot account the app itself posts as
+# for automated first-party messages (the #72 welcome message, and whatever
+# comes next) -- distinct from bot_service.py's admin-created integration
+# bots, which each need a human actor and audit-log entry for creating them.
+# There's no actor here: this account is provisioned lazily, the first time
+# something needs to post as it.
+SYSTEM_USERNAME = "system"
+
+
+async def get_or_create_system_user(db: AsyncSession) -> User:
+    result = await db.execute(select(User).where(User.username == SYSTEM_USERNAME))
+    user = result.scalar_one_or_none()
+    if user is not None:
+        return user
+
+    # Same placeholder-email/discarded-password shape as bot_service.create_bot
+    # -- this account never logs in, email just satisfies the NOT NULL/unique
+    # column.
+    user = User(
+        username=SYSTEM_USERNAME,
+        email=f"{SYSTEM_USERNAME}@bots.example.com",
+        password_hash=hash_password(generate_token()),
+        is_bot=True,
+    )
+    db.add(user)
+    try:
+        await db.flush()
+    except IntegrityError:
+        # Two concurrent requests both found no existing row and raced to
+        # create one -- the loser just reads back the winner's row instead
+        # of erroring.
+        await db.rollback()
+        result = await db.execute(select(User).where(User.username == SYSTEM_USERNAME))
+        return result.scalar_one()
+
+    await db.commit()
+    await db.refresh(user)
+    return user

backend/app/services/user_agent_service.py

@@ -0,0 +1,46 @@
+def describe_user_agent(user_agent: str | None) -> str:
+    """A short, human-readable "Browser on OS" label for the sessions list
+    -- no dependency pulled in for this (the app has stayed on a
+    zero-subdependency-when-possible diet, see MessageContent.tsx's
+    markdown-to-jsx choice), just substring checks against the handful of
+    tokens that actually distinguish the browsers/platforms this app's
+    users run. Order matters: Electron and Edge both also contain
+    "Chrome/", and Chrome-on-iOS/Safari-on-iOS both contain "Safari/", so
+    the more specific token has to be checked first.
+    """
+    if not user_agent:
+        return "Unknown device"
+
+    if "Electron/" in user_agent:
+        browser = "DS Chat Desktop"
+    elif "Edg/" in user_agent:
+        browser = "Edge"
+    elif "OPR/" in user_agent:
+        browser = "Opera"
+    elif "Firefox/" in user_agent:
+        browser = "Firefox"
+    elif "Chrome/" in user_agent:
+        browser = "Chrome"
+    elif "CriOS/" in user_agent:
+        browser = "Chrome"
+    elif "Safari/" in user_agent:
+        browser = "Safari"
+    else:
+        browser = "Unknown browser"
+
+    if "Windows" in user_agent:
+        os_name = "Windows"
+    elif "Mac OS X" in user_agent and ("iPhone" in user_agent or "iPad" in user_agent):
+        os_name = "iOS"
+    elif "Mac OS X" in user_agent:
+        os_name = "macOS"
+    elif "Android" in user_agent:
+        os_name = "Android"
+    elif "Linux" in user_agent:
+        os_name = "Linux"
+    else:
+        os_name = "Unknown OS"
+
+    if browser == "DS Chat Desktop":
+        return f"{browser} ({os_name})"
+    return f"{browser} on {os_name}"

backend/app/services/webhook_service.py

@@ -27,6 +27,10 @@ class SubscriptionNotFoundError(Exception):
     pass
 
 
+class RoomArchivedError(Exception):
+    pass
+
+
 async def create_incoming_webhook(
     db: AsyncSession, actor: User, room_id: uuid.UUID, description: str | None
 ) -> WebhookIncoming:
@@ -82,6 +86,11 @@ async def post_via_webhook(db: AsyncSession, token: str, content: str) -> tuple[
     webhook = result.scalar_one_or_none()
     if webhook is None:
         raise WebhookNotFoundError()
+    # #57: same read-only rule as a human posting from the composer -- an
+    # archived room shouldn't gain new messages through a bot integration
+    # either.
+    if webhook.room.is_archived:
+        raise RoomArchivedError()
 
     message = await create_message(db, webhook.room_id, webhook.created_by, content)
     return message, webhook.room, webhook.creator

backend/app/storage.py

@@ -25,6 +25,19 @@ ALLOWED_IMAGE_CONTENT_TYPES: dict[str, tuple[str, str]] = {
     "image/webp": (".webp", "WEBP"),
 }
 
+# #65: browser-natively-playable video formats -- used to decide whether a
+# stored MessageFile gets served inline (a <video> tag can actually play
+# it) or forced to download like every other non-image attachment (see
+# rooms.py's file-serve endpoint). Deliberately a strict allowlist, not
+# "every video/* type": .mov (video/quicktime) has spotty <video> support
+# outside Safari, and more importantly this is the one thing standing
+# between "serve with the browser trusting our declared Content-Type" and
+# reopening the same-origin-script-execution risk Content-Disposition:
+# attachment exists to close off for arbitrary uploads -- it must only
+# ever contain types a <video> tag renders as media, never as something
+# that could execute script.
+INLINE_SAFE_VIDEO_CONTENT_TYPES = frozenset({"video/mp4", "video/webm", "video/ogg"})
+
 
 class UploadTooLargeError(Exception):
     pass

backend/app/ws/chat.py

@@ -6,10 +6,12 @@ from sqlalchemy import select
 from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.database import get_db
-from app.models import ApiToken, Message, MessageFile, MessageImage, RoomMembership, User
+from app.models import ApiToken, Message, MessageFile, MessageImage, Room, RoomMembership, User
 from app.services.bot_service import resolve_token
 from app.services.message_events import (
+    broadcast_dm_presence_update,
     broadcast_member_updated,
+    broadcast_message_delete,
     broadcast_message_update,
     broadcast_new_message,
     broadcast_reaction_update,
@@ -18,10 +20,12 @@ from app.services.message_service import (
     MessageNotFoundError,
     NotMessageAuthorError,
     create_message,
+    delete_message,
     edit_message,
     toggle_reaction,
 )
 from app.services.room_service import mark_room_read
+from app.services.session_service import resolve_session
 
 router = APIRouter(tags=["ws"])
 
@@ -36,6 +40,7 @@ class ClientEnvelope(BaseModel):
     file_id: uuid.UUID | None = None
     message_id: uuid.UUID | None = None
     emoji: str | None = None
+    focused: bool | None = None
 
 
 async def _is_room_member(db: AsyncSession, room_id: uuid.UUID, user_id: uuid.UUID) -> bool:
@@ -47,6 +52,11 @@ async def _is_room_member(db: AsyncSession, room_id: uuid.UUID, user_id: uuid.UU
     return result.scalar_one_or_none() is not None
 
 
+async def _is_room_archived(db: AsyncSession, room_id: uuid.UUID) -> bool:
+    room = await db.get(Room, room_id)
+    return room is not None and room.is_archived
+
+
 def _missing_scope(api_token: ApiToken | None, scope: str) -> bool:
     return api_token is not None and scope not in api_token.scopes
 
@@ -66,11 +76,15 @@ async def chat_endpoint(websocket: WebSocket, db: AsyncSession = Depends(get_db)
             return
         user, api_token = resolved
     else:
-        user_id_raw = websocket.session.get("user_id")
+        session_id_raw = websocket.session.get("session_id")
-        if not user_id_raw:
+        if not session_id_raw:
             await websocket.close(code=WS_UNAUTHENTICATED)
             return
-        user = await db.get(User, uuid.UUID(user_id_raw))
+        session = await resolve_session(db, uuid.UUID(session_id_raw))
+        if session is None:
+            await websocket.close(code=WS_UNAUTHENTICATED)
+            return
+        user = await db.get(User, session.user_id)
         if user is None or not user.is_active:
             await websocket.close(code=WS_UNAUTHENTICATED)
             return
@@ -79,8 +93,14 @@ async def chat_endpoint(websocket: WebSocket, db: AsyncSession = Depends(get_db)
     manager = websocket.app.state.connection_manager
     presence = websocket.app.state.presence
     global_presence = websocket.app.state.global_presence
+    focus_presence = websocket.app.state.focus_presence
     broadcaster = websocket.app.state.broadcaster
     joined_rooms: set[uuid.UUID] = set()
+    # Tracks this connection's last-reported focus state (see the "focus"
+    # envelope below) so the disconnect cleanup can release FocusPresence's
+    # refcount if the socket closes while still blurred -- mirroring how
+    # joined_rooms tracks per-connection room membership for its own cleanup.
+    is_blurred = False
     manager.register_user(user.id, websocket)
     # Only broadcast on a genuine offline->online transition (this user's
     # first open connection), not for every extra tab -- broadcast_member_
@@ -89,10 +109,23 @@ async def chat_endpoint(websocket: WebSocket, db: AsyncSession = Depends(get_db)
     # visible.
     if await global_presence.connect(user.id):
         await broadcast_member_updated(db, broadcaster, user.id)
+        await broadcast_dm_presence_update(db, broadcaster, user.id, online=True)
+    # This session is shared for the connection's entire lifetime (which can
+    # be hours) -- SQLAlchemy opens a transaction implicitly on first use,
+    # and every read above (the auth lookup, broadcast_member_updated's own
+    # query) leaves it open with nothing to ever close it otherwise. Left
+    # uncommitted, that transaction sits "idle in transaction" holding locks
+    # for as long as the socket stays open -- confirmed in production
+    # blocking unrelated schema migrations on the same tables for 30+
+    # minutes. Committing here, and again after every frame below, means
+    # the connection is never sitting on an open transaction while merely
+    # waiting for the next one.
+    await db.commit()
 
     try:
         while True:
             raw = await websocket.receive_json()
+            try:
                 try:
                     envelope = ClientEnvelope.model_validate(raw)
                 except ValidationError:
@@ -121,6 +154,25 @@ async def chat_endpoint(websocket: WebSocket, db: AsyncSession = Depends(get_db)
                     await presence.leave(envelope.room_id, user.id)
                     joined_rooms.discard(envelope.room_id)
 
+                elif envelope.type == "focus":
+                    # Sent only by the desktop client (#59), independent of
+                    # room join/leave -- see FocusPresence's docstring for
+                    # why widening desktop_notification eligibility this
+                    # way no longer needs to touch live room delivery at
+                    # all, unlike the "leave the room's channel on blur"
+                    # approach this replaced.
+                    if envelope.focused is None:
+                        await websocket.send_json({"type": "error", "detail": "focused required"})
+                        continue
+                    if envelope.focused:
+                        if is_blurred:
+                            await focus_presence.mark_focused(user.id)
+                            is_blurred = False
+                    else:
+                        if not is_blurred:
+                            await focus_presence.mark_blurred(user.id)
+                            is_blurred = True
+
                 elif envelope.type == "message":
                     if envelope.room_id is None or (
                         not envelope.content
@@ -146,6 +198,15 @@ async def chat_endpoint(websocket: WebSocket, db: AsyncSession = Depends(get_db)
                             {"type": "error", "detail": "Not a member of this room"}
                         )
                         continue
+                    if await _is_room_archived(db, envelope.room_id):
+                        # #57: history stays fully readable (joining/reading
+                        # an archived room's channel is untouched above),
+                        # this is the one gate that actually makes archiving
+                        # do something for people who were already members.
+                        await websocket.send_json(
+                            {"type": "error", "detail": "This room has been archived and is read-only"}
+                        )
+                        continue
                     image_id = None
                     if envelope.image_id is not None:
                         image = await db.get(MessageImage, envelope.image_id)
@@ -163,16 +224,27 @@ async def chat_endpoint(websocket: WebSocket, db: AsyncSession = Depends(get_db)
                     message = await create_message(
                         db, envelope.room_id, user.id, envelope.content, image_id, file_id
                     )
-                # Sending implies having seen the room as of now -- without
+                    # Sending implies having seen the room as of now --
-                # this, GET /rooms/mine would show the sender's own room as
+                    # without this, GET /rooms/mine would show the sender's
-                # unread the instant they send into it (last_read_at isn't
+                    # own room as unread the instant they send into it
-                # otherwise bumped until the frontend's own message echo
+                    # (last_read_at isn't otherwise bumped until the
-                # triggers a mark-read call, which is a real but avoidable
+                    # frontend's own message echo triggers a mark-read
-                # race). Deliberately not done in create_message() itself:
+                    # call, which is a real but avoidable race).
-                # the incoming-webhook path also calls it, and a webhook's
+                    # Deliberately not done in create_message() itself: the
+                    # incoming-webhook path also calls it, and a webhook's
                     # attributed sender may not actually be watching.
                     await mark_room_read(db, envelope.room_id, user.id)
-                await broadcast_new_message(db, broadcaster, presence, envelope.room_id, message, user)
+                    await broadcast_new_message(
+                        db,
+                        broadcaster,
+                        presence,
+                        focus_presence,
+                        global_presence,
+                        str(websocket.base_url),
+                        envelope.room_id,
+                        message,
+                        user,
+                    )
 
                 elif envelope.type == "edit":
                     if envelope.room_id is None or envelope.message_id is None or not envelope.content:
@@ -204,12 +276,46 @@ async def chat_endpoint(websocket: WebSocket, db: AsyncSession = Depends(get_db)
                         continue
                     await broadcast_message_update(db, broadcaster, envelope.room_id, message)
 
+                elif envelope.type == "delete":
+                    if envelope.room_id is None or envelope.message_id is None:
+                        await websocket.send_json(
+                            {"type": "error", "detail": "room_id and message_id required"}
+                        )
+                        continue
+                    if _missing_scope(api_token, "write:messages"):
+                        await websocket.send_json(
+                            {"type": "error", "detail": "Token missing required scope: write:messages"}
+                        )
+                        continue
+                    if envelope.room_id not in joined_rooms or not await _is_room_member(
+                        db, envelope.room_id, user.id
+                    ):
+                        await websocket.send_json(
+                            {"type": "error", "detail": "Not a member of this room"}
+                        )
+                        continue
+                    try:
+                        await delete_message(db, envelope.message_id, user.id)
+                    except MessageNotFoundError:
+                        await websocket.send_json({"type": "error", "detail": "Message not found"})
+                        continue
+                    except NotMessageAuthorError:
+                        await websocket.send_json(
+                            {"type": "error", "detail": "You can only delete your own messages"}
+                        )
+                        continue
+                    await broadcast_message_delete(broadcaster, envelope.room_id, envelope.message_id)
+
                 elif envelope.type == "reaction":
                     if (
                         envelope.room_id is None
                         or envelope.message_id is None
                         or not envelope.emoji
-                    or len(envelope.emoji) > 8
+                        # #18: a raw unicode glyph never gets close to this,
+                        # but a custom emoji reaction is stored as its
+                        # literal `:shortcode:` text (see MessageReaction.emoji's
+                        # String(32) column, which this matches exactly).
+                        or len(envelope.emoji) > 32
                     ):
                         await websocket.send_json(
                             {"type": "error", "detail": "room_id, message_id, and emoji required"}
@@ -228,7 +334,11 @@ async def chat_endpoint(websocket: WebSocket, db: AsyncSession = Depends(get_db)
                         )
                         continue
                     target_message = await db.get(Message, envelope.message_id)
-                if target_message is None or target_message.room_id != envelope.room_id:
+                    if (
+                        target_message is None
+                        or target_message.room_id != envelope.room_id
+                        or target_message.deleted_at is not None
+                    ):
                         await websocket.send_json({"type": "error", "detail": "Message not found"})
                         continue
                     reactions = await toggle_reaction(db, envelope.message_id, user.id, envelope.emoji)
@@ -240,6 +350,13 @@ async def chat_endpoint(websocket: WebSocket, db: AsyncSession = Depends(get_db)
                     await websocket.send_json(
                         {"type": "error", "detail": f"Unknown message type: {envelope.type}"}
                     )
+            finally:
+                # See the comment on the pre-loop commit above -- guarantees
+                # every single frame, on every exit path (including the
+                # many `continue`s above, which still run a `finally`
+                # before actually looping), leaves nothing open while this
+                # blocks on the next receive_json().
+                await db.commit()
 
     except WebSocketDisconnect:
         pass
@@ -248,5 +365,8 @@ async def chat_endpoint(websocket: WebSocket, db: AsyncSession = Depends(get_db)
         manager.unregister_user(user.id, websocket)
         for room_id in joined_rooms:
             await presence.leave(room_id, user.id)
+        if is_blurred:
+            await focus_presence.mark_focused(user.id)
         if await global_presence.disconnect(user.id):
             await broadcast_member_updated(db, broadcaster, user.id)
+            await broadcast_dm_presence_update(db, broadcaster, user.id, online=False)

backend/app/ws/focus_presence.py

@@ -0,0 +1,45 @@
+import uuid
+
+from redis.asyncio import Redis
+
+
+class FocusPresence:
+    """Cross-instance "is this desktop-mode user's window currently
+    unfocused," used only to widen desktop_notification/push eligibility
+    beyond plain room-connection state (#59). A Redis hash (field =
+    user_id, value = refcount of that user's currently-blurred desktop
+    connections), parallel to Presence/GlobalPresence.
+
+    Absence from this hash is the default and means "focused." That default
+    is also exactly right for every browser-tab connection: only the
+    desktop client ever sends focus/blur frames at all (see chat.py's
+    "focus" envelope handling), so a browser user never appears here --
+    their attention is already fully captured by Presence's room-connection
+    state, which stays visibility-gated with no separate focus signal.
+
+    Refcounted for the same multi-connection reason as Presence/
+    GlobalPresence, with the same known simplification: two desktop windows
+    for one user, one focused and one blurred, count as "unfocused" here
+    (refcount > 0) even though the user does have attention somewhere. That
+    errs toward notifying rather than silently missing one, which is the
+    safer failure mode for a notification.
+    """
+
+    def __init__(self, redis: Redis) -> None:
+        self._redis = redis
+
+    def _key(self) -> str:
+        return "presence:unfocused"
+
+    async def mark_blurred(self, user_id: uuid.UUID) -> None:
+        await self._redis.hincrby(self._key(), str(user_id), 1)
+
+    async def mark_focused(self, user_id: uuid.UUID) -> None:
+        key = self._key()
+        field = str(user_id)
+        remaining = await self._redis.hincrby(key, field, -1)
+        if remaining <= 0:
+            await self._redis.hdel(key, field)
+
+    async def is_unfocused(self, user_id: uuid.UUID) -> bool:
+        return await self._redis.hexists(self._key(), str(user_id))

backend/pyproject.toml

@@ -1,6 +1,6 @@
 [project]
 name = "ds-chat"
-version = "1.0.0"
+version = "2026.9.4"
 description = "DS Chat backend service"
 license = { text = "AGPL-3.0-or-later" }
 requires-python = ">=3.11"
@@ -15,7 +15,14 @@ dependencies = [
     "pydantic-settings>=2.6",
     "argon2-cffi>=23.1",
     "itsdangerous>=2.2",
-    "pywebpush>=2.0",
+    # #56: >=2.0 let the production venv sit on an old 2.0.x with no real
+    # downside to bumping the floor -- worth keeping current regardless.
+    # Doesn't by itself fix WNS (Windows/Edge push): despite
+    # web-push-libs/pywebpush#162's discussion, even the latest release
+    # (2.4.0) has no WNS-specific header handling in its own source. The
+    # actual fix is app/services/push_service.py adding the required
+    # X-WNS-Cache-Policy header itself via webpush()'s `headers` param.
+    "pywebpush>=2.4.0",
     "redis>=5.0",
     "httpx>=0.27",
     "gunicorn>=23.0",

backend/tests/test_archive.py

@@ -0,0 +1,121 @@
+import uuid
+
+from app.models import User
+from app.schemas.user import UserCreate
+from app.services.auth_service import register_user
+from tests.conftest import register_and_login
+
+
+def _unique(prefix: str) -> str:
+    return f"{prefix}-{uuid.uuid4().hex[:8]}"
+
+
+async def _make_admin(db_session, user_id: str) -> None:
+    user = await db_session.get(User, uuid.UUID(user_id))
+    user.is_site_admin = True
+    await db_session.commit()
+
+
+def _make_admin_ws(ws_client, user_id: str) -> None:
+    async def _promote():
+        async with ws_client.session_factory() as session:
+            user = await session.get(User, uuid.UUID(user_id))
+            user.is_site_admin = True
+            await session.commit()
+
+    ws_client.portal.call(_promote)
+
+
+def _register_ws(ws_client, username: str) -> dict:
+    async def _seed():
+        async with ws_client.session_factory() as session:
+            await register_user(
+                session,
+                UserCreate(username=username, email=f"{username}@example.com", password="password123"),
+            )
+
+    ws_client.portal.call(_seed)
+    resp = ws_client.post(
+        "/api/auth/login", json={"username_or_email": username, "password": "password123"}
+    )
+    assert resp.status_code == 200, resp.text
+    return resp.json()
+
+
+async def test_archived_room_flag_reaches_existing_members(client, db_session):
+    # #57: is_archived used to only ever reach the admin portal's own
+    # AdminRoom schema -- a member's own view of the room (GET /rooms/mine)
+    # had no way to know it was archived at all.
+    admin = await register_and_login(client, db_session, username=_unique("admin"))
+    await _make_admin(db_session, admin["id"])
+    room = (await client.post("/api/rooms", json={"name": _unique("general")})).json()
+
+    resp = await client.post(f"/api/admin/rooms/{room['id']}/archive")
+    assert resp.status_code == 200
+
+    mine = (await client.get("/api/rooms/mine")).json()
+    entry = next(r for r in mine if r["id"] == room["id"])
+    assert entry["is_archived"] is True
+
+    # History stays fully readable for an existing member.
+    messages_resp = await client.get(f"/api/rooms/{room['id']}/messages")
+    assert messages_resp.status_code == 200
+
+    resp = await client.post(f"/api/admin/rooms/{room['id']}/unarchive")
+    assert resp.status_code == 200
+    mine = (await client.get("/api/rooms/mine")).json()
+    entry = next(r for r in mine if r["id"] == room["id"])
+    assert entry["is_archived"] is False
+
+
+def test_ws_message_rejected_in_archived_room(ws_client_factory, db_session):
+    admin_ws = ws_client_factory()
+    admin = _register_ws(admin_ws, _unique("admin"))
+    _make_admin_ws(admin_ws, admin["id"])
+    room = admin_ws.post("/api/rooms", json={"name": _unique("general")}).json()
+
+    archive_resp = admin_ws.post(f"/api/admin/rooms/{room['id']}/archive")
+    assert archive_resp.status_code == 200
+
+    with admin_ws.websocket_connect("/ws/chat") as ws:
+        ws.send_json({"type": "join", "room_id": room["id"]})
+        assert ws.receive_json()["type"] == "joined"
+
+        ws.send_json({"type": "message", "room_id": room["id"], "content": "should not send"})
+        received = ws.receive_json()
+        assert received["type"] == "error"
+        assert "archived" in received["detail"].lower()
+
+
+def test_ws_message_allowed_again_after_unarchive(ws_client_factory):
+    admin_ws = ws_client_factory()
+    admin = _register_ws(admin_ws, _unique("admin"))
+    _make_admin_ws(admin_ws, admin["id"])
+    room = admin_ws.post("/api/rooms", json={"name": _unique("general")}).json()
+
+    admin_ws.post(f"/api/admin/rooms/{room['id']}/archive")
+    admin_ws.post(f"/api/admin/rooms/{room['id']}/unarchive")
+
+    with admin_ws.websocket_connect("/ws/chat") as ws:
+        ws.send_json({"type": "join", "room_id": room["id"]})
+        assert ws.receive_json()["type"] == "joined"
+
+        ws.send_json({"type": "message", "room_id": room["id"], "content": "back online"})
+        received = ws.receive_json()
+        assert received["type"] == "message"
+        assert received["content"] == "back online"
+
+
+async def test_incoming_webhook_rejected_in_archived_room(client, db_session):
+    admin = await register_and_login(client, db_session, username=_unique("admin"))
+    await _make_admin(db_session, admin["id"])
+    room = (await client.post("/api/rooms", json={"name": _unique("general")})).json()
+    webhook = (await client.post(f"/api/rooms/{room['id']}/webhooks/incoming", json={})).json()
+
+    await client.post(f"/api/admin/rooms/{room['id']}/archive")
+
+    resp = await client.post(
+        f"/api/webhooks/incoming/{webhook['token']}", json={"content": "should not post"}
+    )
+    assert resp.status_code == 403
+    assert "archived" in resp.json()["detail"].lower()

backend/tests/test_broadcast.py

@@ -8,21 +8,25 @@ def _unique(prefix: str) -> str:
     return f"{prefix}-{uuid.uuid4().hex[:8]}"
 
 
+_NOISE_TYPES = {"member_updated", "dm_presence_update"}
+
+
 def _recv(ws) -> dict:
-    """Reads the next frame, transparently discarding member_updated
+    """Reads the next frame, transparently discarding presence-change
-    presence-change broadcasts -- another connection in the same room going
+    broadcasts (member_updated, and #63's dm_presence_update) -- another
-    online/offline is real, expected noise these tests aren't about."""
+    connection sharing a room or a DM going online/offline is real,
+    expected noise these tests aren't about."""
     while True:
         msg = ws.receive_json()
-        if msg.get("type") != "member_updated":
+        if msg.get("type") not in _NOISE_TYPES:
             return msg
 
 
 def _fake_send_email(monkeypatch):
     calls = []
 
-    async def fake(db, to, subject, body):
+    async def fake(db, to, subject, paragraphs, **kwargs):
-        calls.append({"to": to, "subject": subject, "body": body})
+        calls.append({"to": to, "subject": subject, "paragraphs": paragraphs, **kwargs})
 
     monkeypatch.setattr("app.services.room_service.send_email", fake)
     return calls
@@ -146,6 +150,65 @@ def test_add_member_notifies_target_user_via_websocket(ws_client_factory, monkey
         assert received == {"type": "room_added", "room_id": room["id"]}
 
 
+def test_start_dm_notifies_other_participant_via_websocket(ws_client_factory):
+    # A production report: bob had no idea a DM existed until he reloaded --
+    # find_or_create_dm was creating the room/membership correctly but never
+    # sending this signal, unlike every other "you're now in a room" path
+    # (add_member, above). Same shape as that test: bob is only ever
+    # "connected," never "joined," proving the signal alone is what tells
+    # his client the room exists at all.
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    alice = _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+
+    with instance2.websocket_connect("/ws/chat") as bob_ws:
+        resp = instance1.post("/api/rooms/dm", json={"other_user_id": bob["id"]})
+        assert resp.status_code == 201, resp.text
+        room = resp.json()
+
+        received = bob_ws.receive_json()
+        assert received == {"type": "room_added", "room_id": room["id"]}
+
+
+def test_new_message_notifies_recipient_who_hid_the_dm_via_websocket(ws_client_factory):
+    # A second production report on the same underlying gap: hiding a DM
+    # correctly clears out of GET /rooms/mine, but when the other person
+    # messages again, the *only* existing signal for that (unread_update)
+    # does `setRooms(prev => prev.map(...))` -- a no-op for a room that
+    # isn't in `prev` at all, which a hidden DM by definition isn't. Needs
+    # the same room_added signal a brand new DM gets, not just a DB-level
+    # un-hide.
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    alice = _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+
+    room = instance1.post("/api/rooms/dm", json={"other_user_id": bob["id"]}).json()
+    resp = instance2.post(f"/api/rooms/{room['id']}/hide")
+    assert resp.status_code == 204
+
+    with instance2.websocket_connect("/ws/chat") as bob_ws:
+        with instance1.websocket_connect("/ws/chat") as alice_ws:
+            alice_ws.send_json({"type": "join", "room_id": room["id"]})
+            assert alice_ws.receive_json()["type"] == "joined"
+            alice_ws.send_json({"type": "message", "room_id": room["id"], "content": "you there?"})
+            alice_ws.receive_json()
+            # Sync barrier (see test_mentions.py's identical helper): the
+            # message ack only proves the room-level broadcast happened,
+            # not that broadcast_new_message's own continuation (which
+            # un-hides the room and publishes room_added) has finished --
+            # a second frame's own ack proves that before this connection
+            # closes underneath it.
+            alice_ws.send_json({"type": "join", "room_id": room["id"]})
+            assert alice_ws.receive_json()["type"] == "joined"
+
+        received = _recv(bob_ws)
+        assert received == {"type": "room_added", "room_id": room["id"]}
+
+
 def test_profile_update_notifies_room_members_via_websocket(ws_client_factory, monkeypatch):
     # Only reaches clients that have the room's own channel joined --
     # exactly the case where a stale avatar/display name would actually be

backend/tests/test_custom_emoji.py

@@ -0,0 +1,275 @@
+import io
+import uuid
+
+from PIL import Image
+
+from app.models import User
+from tests.conftest import register_and_login
+
+
+def _unique(prefix: str) -> str:
+    return f"{prefix}-{uuid.uuid4().hex[:8]}"
+
+
+def _png_bytes(size: tuple[int, int] = (10, 10), color: tuple[int, int, int] = (255, 0, 0)) -> bytes:
+    buf = io.BytesIO()
+    Image.new("RGB", size, color=color).save(buf, format="PNG")
+    return buf.getvalue()
+
+
+async def _make_admin(db_session, user_id: str) -> None:
+    user = await db_session.get(User, uuid.UUID(user_id))
+    user.is_site_admin = True
+    await db_session.commit()
+
+
+async def test_upload_custom_emoji_succeeds(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+    resp = await client.post(
+        "/api/custom-emoji",
+        data={"shortcode": "party-parrot"},
+        files={"file": ("parrot.png", _png_bytes(), "image/png")},
+    )
+    assert resp.status_code == 201, resp.text
+    body = resp.json()
+    assert body["shortcode"] == "party-parrot"
+    assert "id" in body
+    assert "created_at" in body
+
+
+async def test_upload_normalizes_shortcode_case(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+    resp = await client.post(
+        "/api/custom-emoji",
+        data={"shortcode": "  PartyParrot  "},
+        files={"file": ("parrot.png", _png_bytes(), "image/png")},
+    )
+    assert resp.status_code == 201, resp.text
+    assert resp.json()["shortcode"] == "partyparrot"
+
+
+async def test_upload_rejects_invalid_shortcode(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+    resp = await client.post(
+        "/api/custom-emoji",
+        data={"shortcode": "a"},  # too short
+        files={"file": ("x.png", _png_bytes(), "image/png")},
+    )
+    assert resp.status_code == 400
+
+
+async def test_upload_rejects_duplicate_shortcode(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+    first = await client.post(
+        "/api/custom-emoji",
+        data={"shortcode": "dupe-test"},
+        files={"file": ("a.png", _png_bytes(), "image/png")},
+    )
+    assert first.status_code == 201, first.text
+
+    second = await client.post(
+        "/api/custom-emoji",
+        data={"shortcode": "dupe-test"},
+        files={"file": ("b.png", _png_bytes(), "image/png")},
+    )
+    assert second.status_code == 409
+
+
+async def test_upload_rejects_non_image(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+    resp = await client.post(
+        "/api/custom-emoji",
+        data={"shortcode": "not-an-image"},
+        files={"file": ("x.txt", b"hello", "text/plain")},
+    )
+    assert resp.status_code == 400
+
+
+async def test_upload_rejects_oversized(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+    oversized = b"0" * (9 * 1024 * 1024)
+    resp = await client.post(
+        "/api/custom-emoji",
+        data={"shortcode": "too-big"},
+        files={"file": ("huge.png", oversized, "image/png")},
+    )
+    assert resp.status_code == 413
+
+
+async def test_list_custom_emoji(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+    await client.post(
+        "/api/custom-emoji",
+        data={"shortcode": _unique("listed")},
+        files={"file": ("a.png", _png_bytes(), "image/png")},
+    )
+    resp = await client.get("/api/custom-emoji")
+    assert resp.status_code == 200
+    assert len(resp.json()) >= 1
+
+
+async def test_serve_custom_emoji_image_by_shortcode(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+    shortcode = _unique("served")
+    upload = await client.post(
+        "/api/custom-emoji",
+        data={"shortcode": shortcode},
+        files={"file": ("a.png", _png_bytes(), "image/png")},
+    )
+    assert upload.status_code == 201
+
+    resp = await client.get(f"/api/custom-emoji/{shortcode}/image")
+    assert resp.status_code == 200
+    assert resp.headers["content-type"] == "image/png"
+
+
+async def test_serve_custom_emoji_image_forces_revalidation(client, db_session):
+    # A timed cache (the original `max-age=300`) meant a browser that had
+    # already fetched a shortcode's image kept serving those bytes for up
+    # to 5 minutes after a delete-and-reupload swapped in a different file
+    # under the same URL -- confirmed live: re-adding an emoji under a
+    # just-deleted shortcode showed the old image. `no-cache` forces
+    # revalidation on every use instead (still cheap: FileResponse's own
+    # ETag/Last-Modified make an actually-unchanged file a 304, not a full
+    # re-transfer).
+    await register_and_login(client, db_session, username=_unique("alice"))
+    shortcode = _unique("revalidated")
+    await client.post(
+        "/api/custom-emoji",
+        data={"shortcode": shortcode},
+        files={"file": ("a.png", _png_bytes(), "image/png")},
+    )
+    resp = await client.get(f"/api/custom-emoji/{shortcode}/image")
+    assert "no-cache" in resp.headers["cache-control"]
+    assert "max-age" not in resp.headers["cache-control"]
+
+
+async def test_reuploading_a_deleted_shortcode_serves_the_new_image(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+    shortcode = _unique("reused")
+    first = await client.post(
+        "/api/custom-emoji",
+        data={"shortcode": shortcode},
+        files={"file": ("red.png", _png_bytes(color=(255, 0, 0)), "image/png")},
+    )
+    assert first.status_code == 201
+    await client.delete(f"/api/custom-emoji/{first.json()['id']}")
+
+    second = await client.post(
+        "/api/custom-emoji",
+        data={"shortcode": shortcode},
+        files={"file": ("blue.png", _png_bytes(color=(0, 0, 255)), "image/png")},
+    )
+    assert second.status_code == 201
+
+    resp = await client.get(f"/api/custom-emoji/{shortcode}/image")
+    served = Image.open(io.BytesIO(resp.content)).convert("RGB")
+    assert served.getpixel((0, 0)) == (0, 0, 255)
+
+
+async def test_serve_unknown_shortcode_404s(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+    resp = await client.get("/api/custom-emoji/no-such-emoji/image")
+    assert resp.status_code == 404
+
+
+async def test_uploader_can_delete_own_emoji(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+    upload = await client.post(
+        "/api/custom-emoji",
+        data={"shortcode": _unique("deleteme")},
+        files={"file": ("a.png", _png_bytes(), "image/png")},
+    )
+    emoji_id = upload.json()["id"]
+
+    resp = await client.delete(f"/api/custom-emoji/{emoji_id}")
+    assert resp.status_code == 204
+
+    listed = (await client.get("/api/custom-emoji")).json()
+    assert emoji_id not in [e["id"] for e in listed]
+
+
+async def test_non_uploader_non_admin_cannot_delete(client, app, db_session):
+    from httpx import ASGITransport, AsyncClient
+
+    await register_and_login(client, db_session, username=_unique("alice"))
+    upload = await client.post(
+        "/api/custom-emoji",
+        data={"shortcode": _unique("guarded")},
+        files={"file": ("a.png", _png_bytes(), "image/png")},
+    )
+    emoji_id = upload.json()["id"]
+
+    async with AsyncClient(transport=ASGITransport(app=app), base_url="http://test") as bob_client:
+        await register_and_login(bob_client, db_session, username=_unique("bob"))
+        resp = await bob_client.delete(f"/api/custom-emoji/{emoji_id}")
+        assert resp.status_code == 403
+
+    listed = (await client.get("/api/custom-emoji")).json()
+    assert emoji_id in [e["id"] for e in listed]
+
+
+async def test_site_admin_can_delete_others_emoji(client, app, db_session):
+    from httpx import ASGITransport, AsyncClient
+
+    alice = await register_and_login(client, db_session, username=_unique("alice"))
+    upload = await client.post(
+        "/api/custom-emoji",
+        data={"shortcode": _unique("admin-deletable")},
+        files={"file": ("a.png", _png_bytes(), "image/png")},
+    )
+    emoji_id = upload.json()["id"]
+
+    async with AsyncClient(transport=ASGITransport(app=app), base_url="http://test") as admin_client:
+        admin = await register_and_login(admin_client, db_session, username=_unique("admin"))
+        await _make_admin(db_session, admin["id"])
+        resp = await admin_client.delete(f"/api/custom-emoji/{emoji_id}")
+        assert resp.status_code == 204
+
+    assert alice["id"]
+
+
+def _register_ws(ws_client, username: str) -> dict:
+    from app.schemas.user import UserCreate
+    from app.services.auth_service import register_user
+
+    async def _seed():
+        async with ws_client.session_factory() as session:
+            await register_user(
+                session,
+                UserCreate(username=username, email=f"{username}@example.com", password="password123"),
+            )
+
+    ws_client.portal.call(_seed)
+    resp = ws_client.post(
+        "/api/auth/login", json={"username_or_email": username, "password": "password123"}
+    )
+    assert resp.status_code == 200, resp.text
+    return resp.json()
+
+
+def test_reaction_accepts_custom_emoji_shortcode_reference(ws_client_factory):
+    instance = ws_client_factory()
+    _register_ws(instance, _unique("alice"))
+    room = instance.post("/api/rooms", json={"name": _unique("general")}).json()
+
+    with instance.websocket_connect("/ws/chat") as ws:
+        ws.send_json({"type": "join", "room_id": room["id"]})
+        assert ws.receive_json()["type"] == "joined"
+        ws.send_json({"type": "message", "room_id": room["id"], "content": "hello"})
+        message = ws.receive_json()
+
+        # A custom emoji reaction is stored as its literal `:shortcode:`
+        # text (14 chars here) -- well past the old 8-char cap that only
+        # ever needed to fit a raw unicode glyph.
+        ws.send_json(
+            {
+                "type": "reaction",
+                "room_id": room["id"],
+                "message_id": message["id"],
+                "emoji": ":party-parrot:",
+            }
+        )
+        reaction_update = ws.receive_json()
+        assert reaction_update["type"] == "reaction_update"
+        assert reaction_update["reactions"][0]["emoji"] == ":party-parrot:"

backend/tests/test_desktop_notifications.py

@@ -128,6 +128,87 @@ def test_desktop_notification_not_sent_to_room_member_who_is_present(ws_client_f
         assert live_message["type"] == "message"
 
 
+def test_desktop_notification_sent_to_connected_but_blurred_member(ws_client_factory):
+    # #59: bob keeps the room's channel joined (so live delivery to a room
+    # actually open on screen never stops) but reports his desktop window
+    # as unfocused via a "focus" frame -- the whole point of this fix is
+    # that notification eligibility no longer needs the client to fake
+    # "offline" by leaving the room's channel, which used to also break
+    # live delivery until the room was manually left and rejoined.
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    alice = _register_ws(instance1, _unique("alice"))
+    room = instance1.post("/api/rooms", json={"name": _unique("general")}).json()
+
+    _register_ws(instance2, _unique("bob"))
+    instance2.post(f"/api/rooms/{room['id']}/join")
+
+    with instance2.websocket_connect("/ws/chat") as bob_ws:
+        bob_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert bob_ws.receive_json()["type"] == "joined"
+
+        bob_ws.send_json({"type": "focus", "focused": False})
+        # Sync barrier -- see test_mentions.py's identical pattern: a
+        # second (idempotent) join only acks once the prior "focus"
+        # frame's own handling (and commit) has completed.
+        bob_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert bob_ws.receive_json()["type"] == "joined"
+
+        with instance1.websocket_connect("/ws/chat") as alice_ws:
+            alice_ws.send_json({"type": "join", "room_id": room["id"]})
+            assert alice_ws.receive_json()["type"] == "joined"
+            message = _send_and_sync(alice_ws, room["id"], "you awake?")
+            assert message["type"] == "message"
+
+        # Live delivery still works -- bob's room channel was never left.
+        live_message = _recv(bob_ws)
+        assert live_message["type"] == "message"
+        assert live_message["content"] == "you awake?"
+
+        # ...and he's still notified, despite being "connected" to the room.
+        desktop_note = _recv(bob_ws)
+        assert desktop_note == {
+            "type": "desktop_notification",
+            "id": message["id"],
+            "room_id": room["id"],
+            "title": f"#{room['name']}",
+            "body": f"{alice['username']}: you awake?",
+        }
+
+
+def test_desktop_notification_not_sent_after_refocus(ws_client_factory):
+    # Proves the "focus" signal is a live toggle, not one-way -- blurring
+    # and then refocusing before the message arrives must fully cancel out.
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    alice = _register_ws(instance1, _unique("alice"))
+    room = instance1.post("/api/rooms", json={"name": _unique("general")}).json()
+
+    _register_ws(instance2, _unique("bob"))
+    instance2.post(f"/api/rooms/{room['id']}/join")
+
+    with instance2.websocket_connect("/ws/chat") as bob_ws:
+        bob_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert bob_ws.receive_json()["type"] == "joined"
+
+        bob_ws.send_json({"type": "focus", "focused": False})
+        bob_ws.send_json({"type": "focus", "focused": True})
+        bob_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert bob_ws.receive_json()["type"] == "joined"
+
+        with instance1.websocket_connect("/ws/chat") as alice_ws:
+            alice_ws.send_json({"type": "join", "room_id": room["id"]})
+            assert alice_ws.receive_json()["type"] == "joined"
+            _send_and_sync(alice_ws, room["id"], "hello again")
+
+        # Refocused before the message arrived -- only the live broadcast,
+        # same as test_desktop_notification_not_sent_to_room_member_who_is_present.
+        live_message = _recv(bob_ws)
+        assert live_message["type"] == "message"
+
+
 def test_desktop_notification_not_sent_to_non_member(ws_client_factory):
     instance1 = ws_client_factory()
     instance2 = ws_client_factory()

backend/tests/test_direct_messages.py

@@ -0,0 +1,342 @@
+import uuid
+
+from sqlalchemy import select
+
+from app.models import Room, RoomMembership
+from app.schemas.user import UserCreate
+from app.services.auth_service import register_user
+from app.services.room_service import dm_room_name
+from tests.conftest import login_as, register_and_login
+
+
+def _unique(prefix: str) -> str:
+    return f"{prefix}-{uuid.uuid4().hex[:8]}"
+
+
+def _register_ws(ws_client, username: str) -> dict:
+    async def _seed():
+        async with ws_client.session_factory() as session:
+            await register_user(
+                session,
+                UserCreate(username=username, email=f"{username}@example.com", password="password123"),
+            )
+
+    ws_client.portal.call(_seed)
+    resp = ws_client.post(
+        "/api/auth/login", json={"username_or_email": username, "password": "password123"}
+    )
+    assert resp.status_code == 200, resp.text
+    return resp.json()
+
+
+async def test_start_dm_creates_private_room_with_both_members(client, db_session):
+    alice = await register_and_login(client, db_session, username="alice")
+    await client.post("/api/auth/logout")
+    bob = await register_and_login(client, db_session, username="bob")
+    await client.post("/api/auth/logout")
+    await login_as(client, "alice")
+
+    resp = await client.post("/api/rooms/dm", json={"other_user_id": bob["id"]})
+    assert resp.status_code == 201, resp.text
+    room = resp.json()
+    assert room["is_dm"] is True
+    assert room["is_private"] is True
+    # The internal name is never meant to be shown, but its scheme is part
+    # of the contract find_or_create_dm relies on -- pin it here so a
+    # future refactor can't silently change it without this test noticing.
+    assert room["name"] == dm_room_name(uuid.UUID(alice["id"]), uuid.UUID(bob["id"]))
+
+    result = await db_session.execute(
+        select(RoomMembership.user_id).where(RoomMembership.room_id == uuid.UUID(room["id"]))
+    )
+    member_ids = {str(row[0]) for row in result.all()}
+    assert member_ids == {alice["id"], bob["id"]}
+
+
+async def test_start_dm_is_idempotent_regardless_of_who_initiates(client, db_session):
+    alice = await register_and_login(client, db_session, username="alice")
+    await client.post("/api/auth/logout")
+    bob = await register_and_login(client, db_session, username="bob")
+
+    resp1 = await client.post("/api/rooms/dm", json={"other_user_id": alice["id"]})
+    assert resp1.status_code == 201
+    room_id = resp1.json()["id"]
+
+    # bob -> alice again should return the same room, not create a second one.
+    resp2 = await client.post("/api/rooms/dm", json={"other_user_id": alice["id"]})
+    assert resp2.status_code == 201
+    assert resp2.json()["id"] == room_id
+
+    await client.post("/api/auth/logout")
+    await login_as(client, "alice")
+    # alice -> bob (reversed direction) should also find the same room.
+    resp3 = await client.post("/api/rooms/dm", json={"other_user_id": bob["id"]})
+    assert resp3.status_code == 201
+    assert resp3.json()["id"] == room_id
+
+
+async def test_start_dm_rejects_self(client, db_session):
+    alice = await register_and_login(client, db_session, username="alice")
+    resp = await client.post("/api/rooms/dm", json={"other_user_id": alice["id"]})
+    assert resp.status_code == 400
+
+
+async def test_start_dm_404s_for_unknown_user(client, db_session):
+    await register_and_login(client, db_session, username="alice")
+    resp = await client.post("/api/rooms/dm", json={"other_user_id": str(uuid.uuid4())})
+    assert resp.status_code == 404
+
+
+async def test_dm_excluded_from_browse_rooms(client, db_session):
+    alice = await register_and_login(client, db_session, username="alice")
+    await client.post("/api/auth/logout")
+    bob = await register_and_login(client, db_session, username="bob")
+    await client.post("/api/rooms/dm", json={"other_user_id": alice["id"]})
+
+    # A third user should never see the DM in the open-rooms listing, even
+    # though find_or_create_dm sets is_private=True (which alone would
+    # already exclude it) -- confirms the belt-and-suspenders is_dm filter
+    # in list_open_rooms is doing something, not just is_private.
+    await client.post("/api/auth/logout")
+    await register_and_login(client, db_session, username="carol")
+    resp = await client.get("/api/rooms")
+    assert resp.status_code == 200
+    assert all(not r["is_dm"] for r in resp.json())
+
+
+async def test_dm_excluded_from_admin_room_list(client, db_session):
+    alice = await register_and_login(client, db_session, username="alice")
+    await client.post("/api/auth/logout")
+    bob = await register_and_login(client, db_session, username="bob")
+    await client.post("/api/rooms/dm", json={"other_user_id": alice["id"]})
+
+    await client.post("/api/auth/logout")
+    admin = await register_and_login(client, db_session, username="dave")
+    from app.models import User
+
+    user = await db_session.get(User, uuid.UUID(admin["id"]))
+    user.is_site_admin = True
+    await db_session.commit()
+
+    resp = await client.get("/api/admin/rooms")
+    assert resp.status_code == 200
+    names = [r["name"] for r in resp.json()]
+    assert dm_room_name(uuid.UUID(alice["id"]), uuid.UUID(bob["id"])) not in names
+
+
+async def test_dm_appears_in_mine_with_partner_info(client, db_session):
+    alice = await register_and_login(client, db_session, username="alice")
+    await client.post("/api/auth/logout")
+    bob = await register_and_login(client, db_session, username="bob", password="password123")
+    # Give bob a display name so the partner payload's precedence is checked
+    # for something other than the fallback username.
+    await client.patch("/api/auth/me", json={"display_name": "Bobby"})
+
+    dm = (await client.post("/api/rooms/dm", json={"other_user_id": alice["id"]})).json()
+
+    await client.post("/api/auth/logout")
+    await login_as(client, "alice")
+    mine = (await client.get("/api/rooms/mine")).json()
+    dm_entry = next(r for r in mine if r["id"] == dm["id"])
+    assert dm_entry["is_dm"] is True
+    assert dm_entry["dm_partner"]["user_id"] == bob["id"]
+    assert dm_entry["dm_partner"]["username"] == "bob"
+    assert dm_entry["dm_partner"]["display_name"] == "Bobby"
+
+    # A regular room's dm_partner is always null.
+    room = (await client.post("/api/rooms", json={"name": "general"})).json()
+    mine = (await client.get("/api/rooms/mine")).json()
+    room_entry = next(r for r in mine if r["id"] == room["id"])
+    assert room_entry["is_dm"] is False
+    assert room_entry["dm_partner"] is None
+
+
+async def test_dm_cannot_be_updated(client, db_session):
+    alice = await register_and_login(client, db_session, username="alice")
+    await client.post("/api/auth/logout")
+    bob = await register_and_login(client, db_session, username="bob")
+    dm = (await client.post("/api/rooms/dm", json={"other_user_id": alice["id"]})).json()
+
+    # bob is a plain 'member' of the DM (no admin/owner role exists for a
+    # DM), so this 403s on the ordinary role gate before ever reaching
+    # update_room's own is_dm guard.
+    resp = await client.patch(f"/api/rooms/{dm['id']}", json={"name": "renamed"})
+    assert resp.status_code == 403
+
+    # A site admin bypasses that role gate (see #48) -- confirms the
+    # explicit is_dm guard inside update_room itself is what stops this,
+    # not just incidental role-based protection.
+    await client.post("/api/auth/logout")
+    admin = await register_and_login(client, db_session, username="carol")
+    from app.models import User
+
+    user = await db_session.get(User, uuid.UUID(admin["id"]))
+    user.is_site_admin = True
+    await db_session.commit()
+    resp = await client.patch(f"/api/rooms/{dm['id']}", json={"name": "renamed"})
+    assert resp.status_code == 400
+
+
+async def test_dm_rejects_add_member_and_join(client, db_session):
+    alice = await register_and_login(client, db_session, username="alice")
+    await client.post("/api/auth/logout")
+    bob = await register_and_login(client, db_session, username="bob")
+    dm = (await client.post("/api/rooms/dm", json={"other_user_id": alice["id"]})).json()
+
+    await client.post("/api/auth/logout")
+    carol = await register_and_login(client, db_session, username="carol")
+
+    # Neither participant has admin/owner role in a DM, so adding a third
+    # person 403s on the existing role gate.
+    await client.post("/api/auth/logout")
+    await login_as(client, "bob")
+    resp = await client.post(f"/api/rooms/{dm['id']}/members", json={"user_id": carol["id"]})
+    assert resp.status_code == 403
+
+    # is_private=True on the DM already blocks the plain join endpoint too.
+    await client.post("/api/auth/logout")
+    await login_as(client, "carol")
+    resp = await client.post(f"/api/rooms/{dm['id']}/join")
+    assert resp.status_code == 400
+
+
+async def test_hide_dm_removes_it_from_mine_for_that_user_only(client, db_session):
+    alice = await register_and_login(client, db_session, username="alice")
+    await client.post("/api/auth/logout")
+    bob = await register_and_login(client, db_session, username="bob")
+    dm = (await client.post("/api/rooms/dm", json={"other_user_id": alice["id"]})).json()
+
+    resp = await client.post(f"/api/rooms/{dm['id']}/hide")
+    assert resp.status_code == 204
+
+    mine = (await client.get("/api/rooms/mine")).json()
+    assert all(r["id"] != dm["id"] for r in mine)
+
+    # Alice never hid it -- still sees it, proving this is per-viewer, not
+    # something that touched the room or bob's membership for everyone.
+    await client.post("/api/auth/logout")
+    await login_as(client, "alice")
+    mine = (await client.get("/api/rooms/mine")).json()
+    assert any(r["id"] == dm["id"] for r in mine)
+
+
+async def test_hide_dm_rejects_regular_rooms(client, db_session):
+    await register_and_login(client, db_session, username="alice")
+    room = (await client.post("/api/rooms", json={"name": "general"})).json()
+    resp = await client.post(f"/api/rooms/{room['id']}/hide")
+    assert resp.status_code == 400
+
+
+async def test_starting_a_dm_again_unhides_it(client, db_session):
+    alice = await register_and_login(client, db_session, username="alice")
+    await client.post("/api/auth/logout")
+    bob = await register_and_login(client, db_session, username="bob")
+    dm = (await client.post("/api/rooms/dm", json={"other_user_id": alice["id"]})).json()
+
+    await client.post(f"/api/rooms/{dm['id']}/hide")
+    mine = (await client.get("/api/rooms/mine")).json()
+    assert all(r["id"] != dm["id"] for r in mine)
+
+    # bob clicking alice in the People list again -- find_or_create_dm
+    # resolves to the same room and un-hides it for him.
+    resp = await client.post("/api/rooms/dm", json={"other_user_id": alice["id"]})
+    assert resp.status_code == 201
+    assert resp.json()["id"] == dm["id"]
+
+    mine = (await client.get("/api/rooms/mine")).json()
+    assert any(r["id"] == dm["id"] for r in mine)
+
+
+def test_new_message_unhides_dm_for_both_participants(ws_client):
+    alice = _register_ws(ws_client, _unique("alice"))
+    bob = _register_ws(ws_client, _unique("bob"))  # ws_client is now logged in as bob
+    dm = ws_client.post("/api/rooms/dm", json={"other_user_id": alice["id"]}).json()
+
+    ws_client.post(f"/api/rooms/{dm['id']}/hide")
+    assert all(r["id"] != dm["id"] for r in ws_client.get("/api/rooms/mine").json())
+
+    ws_client.post(
+        "/api/auth/login", json={"username_or_email": alice["username"], "password": "password123"}
+    )
+    with ws_client.websocket_connect("/ws/chat") as ws:
+        ws.send_json({"type": "join", "room_id": dm["id"]})
+        assert ws.receive_json()["type"] == "joined"
+        ws.send_json({"type": "message", "room_id": dm["id"], "content": "you there?"})
+        ws.receive_json()
+        # Sync barrier (see test_mentions.py's identical helper): the
+        # message ack only proves the room-level broadcast happened, not
+        # that broadcast_new_message's own continuation (which un-hides
+        # the room) has finished -- a second frame's own ack proves that.
+        ws.send_json({"type": "join", "room_id": dm["id"]})
+        assert ws.receive_json()["type"] == "joined"
+
+    # bob never re-opened the DM himself -- alice's message alone unhid it.
+    ws_client.post(
+        "/api/auth/login", json={"username_or_email": bob["username"], "password": "password123"}
+    )
+    assert any(r["id"] == dm["id"] for r in ws_client.get("/api/rooms/mine").json())
+
+
+def test_dm_partner_presence_update_delivered_without_room_open(ws_client_factory):
+    # #63: alice never joins the DM's own room channel anywhere in this
+    # test -- exactly the normal state for a DM sitting in the sidebar that
+    # isn't the currently open room. member_updated's room-channel broadcast
+    # would never reach her in that state (Presence gates it on having that
+    # specific room joined); this signal has to arrive on her own per-user
+    # channel instead, same as room_added.
+    #
+    # Only the connect ("online") side is exercised here, not disconnect --
+    # see test_presence.py's module docstring for why the offline half
+    # isn't reliably testable via a `with websocket_connect(...)` block
+    # closing (TestClient cancels the server task rather than delivering a
+    # real disconnect, which can interrupt a `finally` block's own awaits
+    # in tests only, never in production).
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    alice = _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+    instance1.post("/api/rooms/dm", json={"other_user_id": bob["id"]})
+
+    with instance1.websocket_connect("/ws/chat") as alice_ws:
+        # Sync barrier: alice's own websocket_connect() returning only
+        # proves the handshake completed, not that chat.py's connection
+        # setup (register_user, in particular -- required before bob's
+        # connect can reach her per-user channel at all) has finished.
+        # Any reply -- even an error -- proves the connection has reached
+        # its main frame loop, which setup always completes before.
+        alice_ws.send_json({"type": "__sync_barrier__"})
+        assert alice_ws.receive_json()["type"] == "error"
+
+        with instance2.websocket_connect("/ws/chat"):
+            online_update = alice_ws.receive_json()
+            assert online_update == {
+                "type": "dm_presence_update",
+                "user_id": bob["id"],
+                "status": "online",
+            }
+
+
+def test_dm_presence_update_not_sent_to_non_partner(ws_client_factory):
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+    instance3 = ws_client_factory()
+
+    alice = _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+    _register_ws(instance3, _unique("outsider"))
+    instance1.post("/api/rooms/dm", json={"other_user_id": bob["id"]})
+
+    with instance3.websocket_connect("/ws/chat") as outsider_ws:
+        with instance2.websocket_connect("/ws/chat"):
+            pass
+
+        # Nothing should ever arrive for an outsider who shares no DM with
+        # bob. Prove the socket stayed quiet the same way
+        # test_desktop_notifications.py's non-member test does: a harmless
+        # self-targeted join, whose prompt "joined" ack proves nothing else
+        # was already queued ahead of it.
+        room = instance3.post("/api/rooms", json={"name": _unique("outsiders-room")}).json()
+        outsider_ws.send_json({"type": "join", "room_id": room["id"]})
+        joined = outsider_ws.receive_json()
+        assert joined == {"type": "joined", "room_id": room["id"]}

backend/tests/test_dm_email_notifications.py

@@ -0,0 +1,207 @@
+import uuid
+
+from app.models import SmtpSettings
+from app.schemas.user import UserCreate
+from app.services.auth_service import register_user
+
+
+def _unique(prefix: str) -> str:
+    return f"{prefix}-{uuid.uuid4().hex[:8]}"
+
+
+def _fake_smtp(monkeypatch):
+    calls = []
+
+    async def fake_send(message, **kwargs):
+        calls.append({"message": message, **kwargs})
+
+    monkeypatch.setattr("app.services.email_service.aiosmtplib.send", fake_send)
+
+    # Monkeypatches get_smtp_settings directly rather than configuring it
+    # for real through the admin endpoint (like test_smtp_settings.py's own
+    # _configure_smtp does) -- ws_client_factory-based tests commit for
+    # real, no rollback, and SmtpSettings is a genuine single global row.
+    # Configuring it for real here previously leaked into every later test
+    # in the same run, breaking test_smtp_settings.py's "starts
+    # unconfigured" assumption. This never touches the DB at all.
+    fake_settings = SmtpSettings(
+        host="smtp.example.com",
+        port=587,
+        username="bot",
+        password_encrypted=None,
+        from_address="noreply@example.com",
+        use_tls=True,
+    )
+
+    async def fake_get_smtp_settings(db):
+        return fake_settings
+
+    monkeypatch.setattr("app.services.email_service.get_smtp_settings", fake_get_smtp_settings)
+    return calls
+
+
+def _register_ws(ws_client, username: str) -> dict:
+    async def _seed():
+        async with ws_client.session_factory() as session:
+            await register_user(
+                session,
+                UserCreate(username=username, email=f"{username}@example.com", password="password123"),
+            )
+
+    ws_client.portal.call(_seed)
+    resp = ws_client.post(
+        "/api/auth/login", json={"username_or_email": username, "password": "password123"}
+    )
+    assert resp.status_code == 200, resp.text
+    return resp.json()
+
+
+def _send_and_sync(ws, room_id: str, content: str) -> dict:
+    """Sync barrier -- see test_mentions.py's identical helper. The
+    "message" ack fires the instant broadcaster.publish() runs, the very
+    first line of broadcast_new_message -- it proves nothing about whether
+    _maybe_email_dm_notification (awaited afterward, in the same handler)
+    has finished. A second, idempotent join's own ack only arrives once
+    the whole prior frame's handling -- including the email step -- is
+    done, since one connection processes frames strictly sequentially."""
+    ws.send_json({"type": "message", "room_id": room_id, "content": content})
+    message = ws.receive_json()
+    ws.send_json({"type": "join", "room_id": room_id})
+    assert ws.receive_json()["type"] == "joined"
+    return message
+
+
+def test_dm_message_emails_globally_offline_recipient(ws_client_factory, monkeypatch):
+    calls = _fake_smtp(monkeypatch)
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    alice = _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+
+    dm = instance1.post("/api/rooms/dm", json={"other_user_id": bob["id"]}).json()
+
+    # bob never connects via WS at all -- genuinely offline, not just
+    # absent from this room's own channel.
+    with instance1.websocket_connect("/ws/chat") as alice_ws:
+        alice_ws.send_json({"type": "join", "room_id": dm["id"]})
+        assert alice_ws.receive_json()["type"] == "joined"
+        _send_and_sync(alice_ws, dm["id"], "hey, you there?")
+
+    assert len(calls) == 1
+    email = calls[0]["message"]
+    assert email["To"] == bob["email"]
+    assert f"New message from {alice['username']}" in email["Subject"]
+    # #68: the email is now multipart/alternative (HTML + plain-text
+    # fallback) -- get_body(preferencelist=...) reaches a specific part,
+    # unlike get_content() which has no handler for the multipart itself.
+    body = email.get_body(preferencelist=("plain",)).get_content()
+    assert f"{alice['username']}: hey, you there?" in body
+    assert f"/rooms/{dm['id']}" in body
+
+
+def test_dm_message_does_not_email_online_recipient(ws_client_factory, monkeypatch):
+    calls = _fake_smtp(monkeypatch)
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    alice = _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+
+    dm = instance1.post("/api/rooms/dm", json={"other_user_id": bob["id"]}).json()
+
+    with instance2.websocket_connect("/ws/chat"):
+        # bob has an open connection -- genuinely online -- even though he
+        # never joins the DM's own room channel.
+        with instance1.websocket_connect("/ws/chat") as alice_ws:
+            alice_ws.send_json({"type": "join", "room_id": dm["id"]})
+            assert alice_ws.receive_json()["type"] == "joined"
+            _send_and_sync(alice_ws, dm["id"], "hey")
+
+    assert calls == []
+
+
+def test_dm_message_emails_appear_offline_recipient_even_when_connected(ws_client_factory, monkeypatch):
+    calls = _fake_smtp(monkeypatch)
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    alice = _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+
+    dm = instance1.post("/api/rooms/dm", json={"other_user_id": bob["id"]}).json()
+
+    resp = instance2.patch("/api/auth/me", json={"appear_offline": True})
+    assert resp.status_code == 200
+
+    with instance2.websocket_connect("/ws/chat"):
+        # bob is connected (genuinely online) but lurking -- appear_offline
+        # should still count as "email me," matching how it already
+        # overrides the presence dot everywhere else.
+        with instance1.websocket_connect("/ws/chat") as alice_ws:
+            alice_ws.send_json({"type": "join", "room_id": dm["id"]})
+            assert alice_ws.receive_json()["type"] == "joined"
+            _send_and_sync(alice_ws, dm["id"], "hey")
+
+    assert len(calls) == 1
+    assert calls[0]["message"]["To"] == bob["email"]
+
+
+def test_regular_room_message_does_not_email_offline_member(ws_client_factory, monkeypatch):
+    calls = _fake_smtp(monkeypatch)
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    _register_ws(instance1, _unique("alice"))
+    room = instance1.post("/api/rooms", json={"name": _unique("general")}).json()
+
+    _register_ws(instance2, _unique("bob"))
+    instance2.post(f"/api/rooms/{room['id']}/join")
+    # bob never connects -- genuinely offline, same as the DM case -- but
+    # this isn't a DM, so #66's email notification is out of scope here.
+
+    with instance1.websocket_connect("/ws/chat") as alice_ws:
+        alice_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert alice_ws.receive_json()["type"] == "joined"
+        _send_and_sync(alice_ws, room["id"], "hello room")
+
+    assert calls == []
+
+
+def test_dm_email_debounced_to_first_unread_then_resets_after_read(ws_client_factory, monkeypatch):
+    calls = _fake_smtp(monkeypatch)
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    alice = _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+
+    dm = instance1.post("/api/rooms/dm", json={"other_user_id": bob["id"]}).json()
+
+    with instance1.websocket_connect("/ws/chat") as alice_ws:
+        alice_ws.send_json({"type": "join", "room_id": dm["id"]})
+        assert alice_ws.receive_json()["type"] == "joined"
+
+        _send_and_sync(alice_ws, dm["id"], "message one")
+        assert len(calls) == 1
+
+        # A second message while bob still hasn't read the first -- no
+        # second email for the same burst.
+        _send_and_sync(alice_ws, dm["id"], "message two")
+        assert len(calls) == 1
+
+    # bob "reads" the conversation via REST -- he never has to have been
+    # connected via WS for this to be meaningful, mark-read is independent
+    # of live connection state.
+    instance2.post(
+        "/api/auth/login", json={"username_or_email": bob["username"], "password": "password123"}
+    )
+    read_resp = instance2.post(f"/api/rooms/{dm['id']}/read")
+    assert read_resp.status_code == 204
+
+    with instance1.websocket_connect("/ws/chat") as alice_ws:
+        alice_ws.send_json({"type": "join", "room_id": dm["id"]})
+        assert alice_ws.receive_json()["type"] == "joined"
+        _send_and_sync(alice_ws, dm["id"], "message three")
+
+    assert len(calls) == 2

backend/tests/test_files.py

@@ -99,6 +99,43 @@ async def test_serve_file_forces_download(client, db_session):
     assert "notes.txt" in disposition
 
 
+async def test_serve_allowlisted_video_inline(client, db_session):
+    # #65: a <video> tag can't play something the browser is forced to
+    # download instead -- browser-playable video types are the one carve-
+    # out from test_serve_file_forces_download's rule above.
+    await register_and_login(client, db_session, username=_unique("alice"))
+    room = (await client.post("/api/rooms", json={"name": _unique("general")})).json()
+    upload = await client.post(
+        f"/api/rooms/{room['id']}/files",
+        files={"file": ("clip.mp4", b"not a real mp4", "video/mp4")},
+    )
+    file_id = upload.json()["id"]
+
+    resp = await client.get(f"/api/rooms/{room['id']}/files/{file_id}")
+    assert resp.status_code == 200
+    assert "content-disposition" not in resp.headers
+    assert resp.headers["content-type"] == "video/mp4"
+
+
+async def test_serve_non_allowlisted_video_still_forces_download(client, db_session):
+    # video/quicktime (.mov) has spotty <video> support outside Safari, and
+    # more importantly this proves the carve-out is a strict allowlist, not
+    # "every video/* content type" -- the security-relevant boundary from
+    # test_serve_file_forces_download must still hold for anything not on
+    # INLINE_SAFE_VIDEO_CONTENT_TYPES.
+    await register_and_login(client, db_session, username=_unique("alice"))
+    room = (await client.post("/api/rooms", json={"name": _unique("general")})).json()
+    upload = await client.post(
+        f"/api/rooms/{room['id']}/files",
+        files={"file": ("clip.mov", b"not a real mov", "video/quicktime")},
+    )
+    file_id = upload.json()["id"]
+
+    resp = await client.get(f"/api/rooms/{room['id']}/files/{file_id}")
+    assert resp.status_code == 200
+    assert "attachment" in resp.headers["content-disposition"]
+
+
 def _register_ws(ws_client, username: str) -> dict:
     from app.schemas.user import UserCreate
     from app.services.auth_service import register_user

backend/tests/test_link_previews.py

@@ -1,9 +1,13 @@
 import asyncio
 import uuid
+from datetime import datetime, timedelta, timezone
 
 import pytest_asyncio
+from sqlalchemy import select
 
+from app.database import async_session_factory
 from app.database import engine as _link_preview_engine
+from app.models import LinkPreview
 from app.schemas.user import UserCreate
 from app.services.auth_service import register_user
 from app.services.link_preview_service import extract_first_url
@@ -294,3 +298,66 @@ async def test_link_preview_reused_across_messages_with_same_url(client, db_sess
     history = (await client.get(f"/api/rooms/{room['id']}/messages")).json()
     assert len(history) == 2
     assert all(m["link_preview"]["title"] == "Example Article" for m in history)
+
+
+async def test_link_preview_refetches_after_cache_expires(client, db_session, monkeypatch):
+    # #70: a real report -- re-posting a URL whose title had genuinely
+    # changed kept showing the stale first-fetch preview, because the
+    # cache TTL used to be 7 days. Simulates that expiry directly (rather
+    # than actually sleeping 5+ minutes) by backdating the cached row's
+    # fetched_at past the TTL, then confirms a second post of the same URL
+    # picks up new content instead of the stale cached title.
+    captured_tasks: list[asyncio.Task] = []
+    real_create_task = asyncio.create_task
+
+    def fake_create_task(coro):
+        task = real_create_task(coro)
+        captured_tasks.append(task)
+        return task
+
+    monkeypatch.setattr("app.services.message_events.asyncio.create_task", fake_create_task)
+    calls: list[str] = []
+    monkeypatch.setattr(
+        "app.services.link_preview_service.httpx.AsyncClient",
+        _fake_client_factory(call_log=calls),
+    )
+    url = _unique_url()
+
+    await register_and_login(client, db_session, username="alice")
+    room = (await client.post("/api/rooms", json={"name": "general"})).json()
+    webhook = (await client.post(f"/api/rooms/{room['id']}/webhooks/incoming", json={})).json()
+
+    resp1 = await client.post(
+        f"/api/webhooks/incoming/{webhook['token']}", json={"content": f"see {url}"}
+    )
+    assert resp1.status_code == 204
+    await asyncio.gather(*captured_tasks)
+    captured_tasks.clear()
+
+    async with async_session_factory() as session:
+        row = (
+            await session.execute(select(LinkPreview).where(LinkPreview.url == url))
+        ).scalar_one()
+        row.fetched_at = datetime.now(timezone.utc) - timedelta(minutes=10)
+        await session.commit()
+
+    updated_html = _OG_HTML.replace(b"Example Article", b"Updated Article")
+    monkeypatch.setattr(
+        "app.services.link_preview_service.httpx.AsyncClient",
+        _fake_client_factory(html=updated_html, call_log=calls),
+    )
+
+    resp2 = await client.post(
+        f"/api/webhooks/incoming/{webhook['token']}", json={"content": f"again: {url}"}
+    )
+    assert resp2.status_code == 204
+    await asyncio.gather(*captured_tasks)
+
+    assert len(calls) == 2  # the expired cache forced a second real fetch
+
+    # Cached by URL, not by message (see link_preview_service.py) -- the
+    # row was refreshed in place, so *both* messages referencing this URL
+    # now show the new title on a history reload, not one each.
+    history = (await client.get(f"/api/rooms/{room['id']}/messages")).json()
+    assert len(history) == 2
+    assert all(m["link_preview"]["title"] == "Updated Article" for m in history)

backend/tests/test_message_delete.py

@@ -0,0 +1,222 @@
+import io
+import uuid
+
+from PIL import Image
+
+from app.schemas.user import UserCreate
+from app.services.auth_service import register_user
+
+
+def _unique(prefix: str) -> str:
+    return f"{prefix}-{uuid.uuid4().hex[:8]}"
+
+
+_NOISE_TYPES = {"member_updated", "desktop_notification", "unread_update"}
+
+
+def _recv(ws) -> dict:
+    """Reads the next frame, transparently discarding presence/offline-
+    notify noise -- see test_message_edit.py's identical helper."""
+    while True:
+        msg = ws.receive_json()
+        if msg.get("type") not in _NOISE_TYPES:
+            return msg
+
+
+def _register_ws(ws_client, username: str) -> dict:
+    async def _seed():
+        async with ws_client.session_factory() as session:
+            await register_user(
+                session,
+                UserCreate(username=username, email=f"{username}@example.com", password="password123"),
+            )
+
+    ws_client.portal.call(_seed)
+    resp = ws_client.post(
+        "/api/auth/login", json={"username_or_email": username, "password": "password123"}
+    )
+    assert resp.status_code == 200, resp.text
+    return resp.json()
+
+
+def _png_bytes() -> bytes:
+    buf = io.BytesIO()
+    Image.new("RGB", (10, 10), color=(255, 0, 0)).save(buf, format="PNG")
+    return buf.getvalue()
+
+
+def test_ws_delete_clears_content_and_broadcasts(ws_client):
+    username = _unique("alice")
+    _register_ws(ws_client, username=username)
+    room = ws_client.post("/api/rooms", json={"name": _unique("general")}).json()
+
+    with ws_client.websocket_connect("/ws/chat") as ws:
+        ws.send_json({"type": "join", "room_id": room["id"]})
+        assert ws.receive_json()["type"] == "joined"
+
+        ws.send_json({"type": "message", "room_id": room["id"], "content": "hello"})
+        message = ws.receive_json()
+
+        ws.send_json({"type": "delete", "room_id": room["id"], "message_id": message["id"]})
+        deleted = ws.receive_json()
+        assert deleted == {"type": "message_deleted", "id": message["id"], "room_id": room["id"]}
+
+    resp = ws_client.get(f"/api/rooms/{room['id']}/messages")
+    history = resp.json()
+    tombstone = next(m for m in history if m["id"] == message["id"])
+    assert tombstone["content"] is None
+    assert tombstone["deleted_at"] is not None
+    assert tombstone["image_id"] is None
+    assert tombstone["file"] is None
+
+
+def test_ws_delete_rejects_non_author(ws_client):
+    alice = _register_ws(ws_client, username=_unique("alice"))
+    room = ws_client.post("/api/rooms", json={"name": _unique("general")}).json()
+
+    bob = _register_ws(ws_client, username=_unique("bob"))
+    ws_client.post(f"/api/rooms/{room['id']}/join")
+
+    ws_client.post(
+        "/api/auth/login", json={"username_or_email": alice["username"], "password": "password123"}
+    )
+    with ws_client.websocket_connect("/ws/chat") as alice_ws:
+        alice_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert alice_ws.receive_json()["type"] == "joined"
+        alice_ws.send_json({"type": "message", "room_id": room["id"], "content": "hello"})
+        message = alice_ws.receive_json()
+
+        ws_client.post(
+            "/api/auth/login",
+            json={"username_or_email": bob["username"], "password": "password123"},
+        )
+        with ws_client.websocket_connect("/ws/chat") as bob_ws:
+            bob_ws.send_json({"type": "join", "room_id": room["id"]})
+            assert _recv(bob_ws)["type"] == "joined"
+            bob_ws.send_json(
+                {"type": "delete", "room_id": room["id"], "message_id": message["id"]}
+            )
+            resp = bob_ws.receive_json()
+            assert resp["type"] == "error"
+            assert "own messages" in resp["detail"]
+
+    resp = ws_client.get(f"/api/rooms/{room['id']}/messages")
+    history = resp.json()
+    still_there = next(m for m in history if m["id"] == message["id"])
+    assert still_there["deleted_at"] is None
+    assert still_there["content"] == "hello"
+
+
+def test_ws_delete_of_unknown_message_errors(ws_client):
+    _register_ws(ws_client, username=_unique("alice"))
+    room = ws_client.post("/api/rooms", json={"name": _unique("general")}).json()
+
+    with ws_client.websocket_connect("/ws/chat") as ws:
+        ws.send_json({"type": "join", "room_id": room["id"]})
+        assert ws.receive_json()["type"] == "joined"
+
+        ws.send_json(
+            {"type": "delete", "room_id": room["id"], "message_id": str(uuid.uuid4())}
+        )
+        resp = ws.receive_json()
+        assert resp == {"type": "error", "detail": "Message not found"}
+
+
+def test_deleted_message_cannot_be_edited_or_reacted_to(ws_client):
+    _register_ws(ws_client, username=_unique("alice"))
+    room = ws_client.post("/api/rooms", json={"name": _unique("general")}).json()
+
+    with ws_client.websocket_connect("/ws/chat") as ws:
+        ws.send_json({"type": "join", "room_id": room["id"]})
+        assert ws.receive_json()["type"] == "joined"
+
+        ws.send_json({"type": "message", "room_id": room["id"], "content": "hello"})
+        message = ws.receive_json()
+
+        ws.send_json({"type": "delete", "room_id": room["id"], "message_id": message["id"]})
+        assert ws.receive_json()["type"] == "message_deleted"
+
+        ws.send_json(
+            {
+                "type": "edit",
+                "room_id": room["id"],
+                "message_id": message["id"],
+                "content": "resurrected",
+            }
+        )
+        assert ws.receive_json() == {"type": "error", "detail": "Message not found"}
+
+        ws.send_json(
+            {
+                "type": "reaction",
+                "room_id": room["id"],
+                "message_id": message["id"],
+                "emoji": "👍",
+            }
+        )
+        assert ws.receive_json() == {"type": "error", "detail": "Message not found"}
+
+
+def test_delete_fans_out_across_instances(ws_client_factory):
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    alice = _register_ws(instance1, _unique("alice"))
+    room = instance1.post("/api/rooms", json={"name": _unique("general")}).json()
+
+    bob = _register_ws(instance2, _unique("bob"))
+    instance2.post(f"/api/rooms/{room['id']}/join")
+
+    with instance2.websocket_connect("/ws/chat") as bob_ws:
+        bob_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert _recv(bob_ws)["type"] == "joined"
+
+        with instance1.websocket_connect("/ws/chat") as alice_ws:
+            alice_ws.send_json({"type": "join", "room_id": room["id"]})
+            assert alice_ws.receive_json()["type"] == "joined"
+            alice_ws.send_json({"type": "message", "room_id": room["id"], "content": "hi"})
+            message = alice_ws.receive_json()
+            assert _recv(bob_ws)["type"] == "message"
+
+            alice_ws.send_json(
+                {"type": "delete", "room_id": room["id"], "message_id": message["id"]}
+            )
+            assert alice_ws.receive_json()["type"] == "message_deleted"
+
+            deleted = _recv(bob_ws)
+            assert deleted == {"type": "message_deleted", "id": message["id"], "room_id": room["id"]}
+
+
+def test_delete_removes_underlying_image_from_disk(ws_client):
+    username = _unique("alice")
+    _register_ws(ws_client, username=username)
+    room = ws_client.post("/api/rooms", json={"name": _unique("general")}).json()
+
+    upload = ws_client.post(
+        f"/api/rooms/{room['id']}/images",
+        files={"file": ("test.png", _png_bytes(), "image/png")},
+    ).json()
+    image_id = upload["id"]
+
+    with ws_client.websocket_connect("/ws/chat") as ws:
+        ws.send_json({"type": "join", "room_id": room["id"]})
+        assert ws.receive_json()["type"] == "joined"
+
+        ws.send_json({"type": "message", "room_id": room["id"], "image_id": image_id})
+        message = ws.receive_json()
+        assert message["image_id"] == image_id
+
+        # Confirm the image actually serves before deleting, so a false
+        # pass (it was never reachable to begin with) can't hide as a true
+        # one below.
+        get_resp = ws_client.get(f"/api/rooms/{room['id']}/images/{image_id}")
+        assert get_resp.status_code == 200
+
+        ws.send_json({"type": "delete", "room_id": room["id"], "message_id": message["id"]})
+        assert ws.receive_json()["type"] == "message_deleted"
+
+    # The image is gone -- both the DB row (via the now-404ing serve
+    # endpoint) and, per #53's "delete the file too" choice, the file
+    # actually unlinked from disk (not just detached and orphaned).
+    get_resp = ws_client.get(f"/api/rooms/{room['id']}/images/{image_id}")
+    assert get_resp.status_code == 404

backend/tests/test_message_edit.py

@@ -8,13 +8,19 @@ def _unique(prefix: str) -> str:
     return f"{prefix}-{uuid.uuid4().hex[:8]}"
 
 
+_NOISE_TYPES = {"member_updated", "desktop_notification", "unread_update"}
+
+
 def _recv(ws) -> dict:
-    """Reads the next frame, transparently discarding member_updated
+    """Reads the next frame, transparently discarding presence/offline-
-    presence-change broadcasts -- another connection in the same room going
+    notify noise -- another connection in the same room going online/
-    online/offline is real, expected noise these tests aren't about."""
+    offline, or a per-user-channel side effect of an earlier offline
+    member's own message, can legitimately arrive right as a connection is
+    established, before its own "joined" ack. Not what these tests are
+    about."""
     while True:
         msg = ws.receive_json()
-        if msg.get("type") != "member_updated":
+        if msg.get("type") not in _NOISE_TYPES:
             return msg
 
 
@@ -90,7 +96,7 @@ def test_ws_edit_rejects_non_author(ws_client):
         )
         with ws_client.websocket_connect("/ws/chat") as bob_ws:
             bob_ws.send_json({"type": "join", "room_id": room["id"]})
-            assert bob_ws.receive_json()["type"] == "joined"
+            assert _recv(bob_ws)["type"] == "joined"
             bob_ws.send_json(
                 {
                     "type": "edit",
@@ -116,7 +122,7 @@ def test_edit_fans_out_across_instances(ws_client_factory):
 
     with instance2.websocket_connect("/ws/chat") as bob_ws:
         bob_ws.send_json({"type": "join", "room_id": room["id"]})
-        assert bob_ws.receive_json()["type"] == "joined"
+        assert _recv(bob_ws)["type"] == "joined"
 
         with instance1.websocket_connect("/ws/chat") as alice_ws:
             alice_ws.send_json({"type": "join", "room_id": room["id"]})

backend/tests/test_password.py

@@ -10,8 +10,17 @@ from tests.conftest import register_and_login
 def _fake_send_email(monkeypatch):
     calls = []
 
-    async def fake(db, to, subject, body):
+    async def fake(db, to, subject, paragraphs, *, cta_label=None, cta_url=None, theme_user=None):
-        calls.append({"to": to, "subject": subject, "body": body})
+        calls.append(
+            {
+                "to": to,
+                "subject": subject,
+                "paragraphs": paragraphs,
+                "cta_label": cta_label,
+                "cta_url": cta_url,
+                "theme_user": theme_user,
+            }
+        )
 
     monkeypatch.setattr("app.services.password_service.send_email", fake)
     return calls
@@ -91,7 +100,7 @@ async def test_reset_password_flow_end_to_end(client, db_session, monkeypatch):
     await client.post("/api/auth/logout")
 
     await client.post("/api/auth/forgot-password", json={"email": "alice@example.com"})
-    token = _extract_token(calls[0]["body"])
+    token = _extract_token(calls[0]["cta_url"])
 
     validate = await client.get(f"/api/auth/reset-password/validate?token={token}")
     assert validate.status_code == 204
@@ -133,7 +142,7 @@ async def test_reset_password_expired_token_rejected(client, db_session, monkeyp
     await register_and_login(client, db_session, username="alice")
     await client.post("/api/auth/logout")
     await client.post("/api/auth/forgot-password", json={"email": "alice@example.com"})
-    token = _extract_token(calls[0]["body"])
+    token = _extract_token(calls[0]["cta_url"])
 
     reset = (await db_session.execute(select(PasswordReset))).scalar_one()
     reset.expires_at = datetime.now(timezone.utc) - timedelta(minutes=1)
@@ -150,7 +159,7 @@ async def test_reset_password_used_token_cannot_be_reused(client, db_session, mo
     await register_and_login(client, db_session, username="alice")
     await client.post("/api/auth/logout")
     await client.post("/api/auth/forgot-password", json={"email": "alice@example.com"})
-    token = _extract_token(calls[0]["body"])
+    token = _extract_token(calls[0]["cta_url"])
 
     first = await client.post(
         "/api/auth/reset-password", json={"token": token, "new_password": "firstpass123"}

backend/tests/test_profile.py

@@ -102,6 +102,62 @@ async def test_theme_custom_rejected_on_generic_profile_update(client, db_sessio
     assert resp.status_code == 422
 
 
+async def test_update_text_scale_persists(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+
+    resp = await client.patch("/api/auth/me", json={"text_scale": "large"})
+    assert resp.status_code == 200, resp.text
+    assert resp.json()["text_scale"] == "large"
+
+    me = await client.get("/api/auth/me")
+    assert me.json()["text_scale"] == "large"
+
+
+async def test_invalid_text_scale_rejected(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+
+    resp = await client.patch("/api/auth/me", json={"text_scale": "huge"})
+    assert resp.status_code == 422
+
+
+async def test_updating_text_scale_does_not_clobber_theme(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+    await client.patch("/api/auth/me", json={"theme": "sunset"})
+
+    resp = await client.patch("/api/auth/me", json={"text_scale": "xlarge"})
+    assert resp.status_code == 200
+    assert resp.json()["theme"] == "sunset"
+    assert resp.json()["text_scale"] == "xlarge"
+
+
+async def test_update_emoji_scale_persists(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+
+    resp = await client.patch("/api/auth/me", json={"emoji_scale": "xlarge"})
+    assert resp.status_code == 200, resp.text
+    assert resp.json()["emoji_scale"] == "xlarge"
+
+    me = await client.get("/api/auth/me")
+    assert me.json()["emoji_scale"] == "xlarge"
+
+
+async def test_invalid_emoji_scale_rejected(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+
+    resp = await client.patch("/api/auth/me", json={"emoji_scale": "huge"})
+    assert resp.status_code == 422
+
+
+async def test_updating_emoji_scale_does_not_clobber_text_scale(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+    await client.patch("/api/auth/me", json={"text_scale": "large"})
+
+    resp = await client.patch("/api/auth/me", json={"emoji_scale": "small"})
+    assert resp.status_code == 200
+    assert resp.json()["text_scale"] == "large"
+    assert resp.json()["emoji_scale"] == "small"
+
+
 async def test_avatar_upload_succeeds_and_persists(client, db_session):
     await register_and_login(client, db_session, username=_unique("alice"))
 

backend/tests/test_push.py

@@ -218,3 +218,115 @@ def test_expired_subscription_is_cleaned_up(ws_client, monkeypatch):
         assert ws.receive_json()["type"] == "joined"
 
     assert _fetch_subscriptions(ws_client, bob["id"]) == []
+
+
+def test_non_gone_push_failure_logs_response_detail_and_keeps_subscription(ws_client, monkeypatch):
+    # #56: a real WNS 400 carries its actual reason in a response *header*,
+    # not the body -- str(WebPushException) alone (what used to be logged)
+    # would have shown neither, which is exactly why that bug took a DB
+    # dump + journalctl correlation to diagnose instead of one log line.
+    class FakeResponse:
+        status_code = 400
+        text = "Bad Request"
+        headers = {"X-WNS-Error-Description": "Ttl value conflicts with X-WNS-Cache-Policy"}
+
+    def fake_webpush(**kwargs):
+        raise WebPushException("Push failed: 400 Bad Request", response=FakeResponse())
+
+    monkeypatch.setattr("app.services.push_service.webpush", fake_webpush)
+
+    # caplog's handler capture isn't reliable here -- the actual push send
+    # (and its logger.warning call) runs on ws_client_factory's background
+    # portal thread (see that fixture's own docstring), not pytest's main
+    # thread. Patching the logger call directly sidesteps that instead of
+    # depending on cross-thread log propagation.
+    calls = []
+    monkeypatch.setattr(
+        "app.services.push_service.logger.warning",
+        lambda msg, *args: calls.append(msg % args),
+    )
+
+    alice = _register_ws(ws_client, _unique("alice"))
+    room = ws_client.post("/api/rooms", json={"name": _unique("general")}).json()
+
+    bob = _register_ws(ws_client, _unique("bob"))
+    ws_client.post(f"/api/rooms/{room['id']}/join")
+    ws_client.post("/api/push/subscribe", json=_subscription_payload(_unique("bob")))
+    assert len(_fetch_subscriptions(ws_client, bob["id"])) == 1
+
+    ws_client.post(
+        "/api/auth/login", json={"username_or_email": alice["username"], "password": "password123"}
+    )
+    with ws_client.websocket_connect("/ws/chat") as ws:
+        ws.send_json({"type": "join", "room_id": room["id"]})
+        assert ws.receive_json()["type"] == "joined"
+        ws.send_json({"type": "message", "room_id": room["id"], "content": "hello"})
+        assert ws.receive_json()["type"] == "message"
+        ws.send_json({"type": "join", "room_id": room["id"]})
+        assert ws.receive_json()["type"] == "joined"
+
+    # A 400 isn't "gone" (404/410) -- the subscription stays, unlike the
+    # expired-subscription case above.
+    assert len(_fetch_subscriptions(ws_client, bob["id"])) == 1
+
+    assert len(calls) == 1
+    assert "Bad Request" in calls[0]
+    assert "Ttl value conflicts with X-WNS-Cache-Policy" in calls[0]
+
+
+def test_wns_endpoint_gets_cache_policy_header(ws_client, monkeypatch):
+    calls = []
+    monkeypatch.setattr("app.services.push_service.webpush", lambda **kw: calls.append(kw))
+
+    alice = _register_ws(ws_client, _unique("alice"))
+    room = ws_client.post("/api/rooms", json={"name": _unique("general")}).json()
+
+    bob = _register_ws(ws_client, _unique("bob"))
+    ws_client.post(f"/api/rooms/{room['id']}/join")
+    ws_client.post(
+        "/api/push/subscribe",
+        json={
+            "endpoint": f"https://wns2-by3p.notify.windows.com/w/{_unique('bob')}",
+            "keys": {"p256dh": "p256dh-bob", "auth": "auth-bob"},
+        },
+    )
+
+    ws_client.post(
+        "/api/auth/login", json={"username_or_email": alice["username"], "password": "password123"}
+    )
+    with ws_client.websocket_connect("/ws/chat") as ws:
+        ws.send_json({"type": "join", "room_id": room["id"]})
+        assert ws.receive_json()["type"] == "joined"
+        ws.send_json({"type": "message", "room_id": room["id"], "content": "hello"})
+        assert ws.receive_json()["type"] == "message"
+        ws.send_json({"type": "join", "room_id": room["id"]})
+        assert ws.receive_json()["type"] == "joined"
+
+    assert len(calls) == 1
+    assert calls[0]["headers"] == {"X-WNS-Cache-Policy": "no-cache"}
+
+
+def test_non_wns_endpoint_gets_no_extra_headers(ws_client, monkeypatch):
+    calls = []
+    monkeypatch.setattr("app.services.push_service.webpush", lambda **kw: calls.append(kw))
+
+    alice = _register_ws(ws_client, _unique("alice"))
+    room = ws_client.post("/api/rooms", json={"name": _unique("general")}).json()
+
+    bob = _register_ws(ws_client, _unique("bob"))
+    ws_client.post(f"/api/rooms/{room['id']}/join")
+    ws_client.post("/api/push/subscribe", json=_subscription_payload(_unique("bob")))
+
+    ws_client.post(
+        "/api/auth/login", json={"username_or_email": alice["username"], "password": "password123"}
+    )
+    with ws_client.websocket_connect("/ws/chat") as ws:
+        ws.send_json({"type": "join", "room_id": room["id"]})
+        assert ws.receive_json()["type"] == "joined"
+        ws.send_json({"type": "message", "room_id": room["id"], "content": "hello"})
+        assert ws.receive_json()["type"] == "message"
+        ws.send_json({"type": "join", "room_id": room["id"]})
+        assert ws.receive_json()["type"] == "joined"
+
+    assert len(calls) == 1
+    assert calls[0]["headers"] is None

backend/tests/test_reactions.py

@@ -9,13 +9,19 @@ def _unique(prefix: str) -> str:
     return f"{prefix}-{uuid.uuid4().hex[:8]}"
 
 
+_NOISE_TYPES = {"member_updated", "desktop_notification", "unread_update"}
+
+
 def _recv(ws) -> dict:
-    """Reads the next frame, transparently discarding member_updated
+    """Reads the next frame, transparently discarding presence/offline-
-    presence-change broadcasts -- another connection in the same room going
+    notify noise -- another connection in the same room going online/
-    online/offline is real, expected noise these tests aren't about."""
+    offline, or a per-user-channel side effect of an earlier offline
+    member's own message, can legitimately arrive right as a connection is
+    established, before its own "joined" ack. Not what these tests are
+    about."""
     while True:
         msg = ws.receive_json()
-        if msg.get("type") != "member_updated":
+        if msg.get("type") not in _NOISE_TYPES:
             return msg
 
 
@@ -122,7 +128,7 @@ def test_reaction_broadcasts_to_other_room_members(ws_client):
         )
         with ws_client.websocket_connect("/ws/chat") as bob_ws:
             bob_ws.send_json({"type": "join", "room_id": room["id"]})
-            assert bob_ws.receive_json()["type"] == "joined"
+            assert _recv(bob_ws)["type"] == "joined"
 
             ws_client.post(
                 "/api/auth/login",

backend/tests/test_room_mention_email_notifications.py

@@ -0,0 +1,255 @@
+import uuid
+
+from app.models import SmtpSettings
+from app.schemas.user import UserCreate
+from app.services.auth_service import register_user
+
+
+def _unique(prefix: str) -> str:
+    return f"{prefix}-{uuid.uuid4().hex[:8]}"
+
+
+def _fake_smtp(monkeypatch):
+    calls = []
+
+    async def fake_send(message, **kwargs):
+        calls.append({"message": message, **kwargs})
+
+    monkeypatch.setattr("app.services.email_service.aiosmtplib.send", fake_send)
+
+    # See test_dm_email_notifications.py's identical helper for why this
+    # monkeypatches get_smtp_settings directly instead of configuring a real
+    # row through the admin endpoint.
+    fake_settings = SmtpSettings(
+        host="smtp.example.com",
+        port=587,
+        username="bot",
+        password_encrypted=None,
+        from_address="noreply@example.com",
+        use_tls=True,
+    )
+
+    async def fake_get_smtp_settings(db):
+        return fake_settings
+
+    monkeypatch.setattr("app.services.email_service.get_smtp_settings", fake_get_smtp_settings)
+    return calls
+
+
+def _register_ws(ws_client, username: str) -> dict:
+    async def _seed():
+        async with ws_client.session_factory() as session:
+            await register_user(
+                session,
+                UserCreate(username=username, email=f"{username}@example.com", password="password123"),
+            )
+
+    ws_client.portal.call(_seed)
+    resp = ws_client.post(
+        "/api/auth/login", json={"username_or_email": username, "password": "password123"}
+    )
+    assert resp.status_code == 200, resp.text
+    return resp.json()
+
+
+def _send_and_sync(ws, room_id: str, content: str) -> dict:
+    """See test_dm_email_notifications.py's identical helper -- the
+    "message" ack alone proves nothing about whether the email step
+    (awaited afterward in the same handler) has finished; a second,
+    idempotent join's ack only arrives once the whole frame is done."""
+    ws.send_json({"type": "message", "room_id": room_id, "content": content})
+    message = ws.receive_json()
+    ws.send_json({"type": "join", "room_id": room_id})
+    assert ws.receive_json()["type"] == "joined"
+    return message
+
+
+def _subscribe(ws_client, room_id: str, username: str, password: str = "password123") -> None:
+    login = ws_client.post(
+        "/api/auth/login", json={"username_or_email": username, "password": password}
+    )
+    assert login.status_code == 200, login.text
+    resp = ws_client.patch(f"/api/rooms/{room_id}/notifications", json={"email_notifications": True})
+    assert resp.status_code == 204, resp.text
+
+
+def test_room_first_message_emails_offline_subscribed_member(ws_client_factory, monkeypatch):
+    calls = _fake_smtp(monkeypatch)
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    alice = _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+    room = instance1.post("/api/rooms", json={"name": _unique("general")}).json()
+    instance2.post(f"/api/rooms/{room['id']}/join")
+    _subscribe(instance2, room["id"], bob["username"])
+    # bob never connects via WS -- genuinely offline.
+
+    with instance1.websocket_connect("/ws/chat") as alice_ws:
+        alice_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert alice_ws.receive_json()["type"] == "joined"
+        _send_and_sync(alice_ws, room["id"], "no mention here, just a plain message")
+
+    assert len(calls) == 1
+    email = calls[0]["message"]
+    assert email["To"] == bob["email"]
+    assert f"New message in #{room['name']}" in email["Subject"]
+    body = email.get_body(preferencelist=("plain",)).get_content()
+    assert alice["username"] in body
+    assert f"/rooms/{room['id']}" in body
+
+
+def test_room_second_plain_message_does_not_reemail_before_read(ws_client_factory, monkeypatch):
+    calls = _fake_smtp(monkeypatch)
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+    room = instance1.post("/api/rooms", json={"name": _unique("general")}).json()
+    instance2.post(f"/api/rooms/{room['id']}/join")
+    _subscribe(instance2, room["id"], bob["username"])
+
+    with instance1.websocket_connect("/ws/chat") as alice_ws:
+        alice_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert alice_ws.receive_json()["type"] == "joined"
+
+        _send_and_sync(alice_ws, room["id"], "message one")
+        assert len(calls) == 1
+
+        # A second plain message while bob still hasn't read the first --
+        # no second email for the same unread burst.
+        _send_and_sync(alice_ws, room["id"], "message two")
+        assert len(calls) == 1
+
+
+def test_room_mention_always_emails_even_mid_unread_burst(ws_client_factory, monkeypatch):
+    calls = _fake_smtp(monkeypatch)
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    alice = _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+    room = instance1.post("/api/rooms", json={"name": _unique("general")}).json()
+    instance2.post(f"/api/rooms/{room['id']}/join")
+    _subscribe(instance2, room["id"], bob["username"])
+
+    with instance1.websocket_connect("/ws/chat") as alice_ws:
+        alice_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert alice_ws.receive_json()["type"] == "joined"
+
+        # First unread message (plain) -- emails once, uses up the debounce.
+        _send_and_sync(alice_ws, room["id"], "hey everyone")
+        assert len(calls) == 1
+
+        # A mention arriving while that first message is still unread --
+        # must email anyway, unlike a second plain message.
+        _send_and_sync(alice_ws, room["id"], f"@{bob['username']} specifically you")
+        assert len(calls) == 2
+
+    mention_email = calls[1]["message"]
+    assert mention_email["To"] == bob["email"]
+    assert f"New mention in #{room['name']}" in mention_email["Subject"]
+    body = mention_email.get_body(preferencelist=("plain",)).get_content()
+    assert f"{alice['username']} mentioned you" in body
+
+
+def test_room_mention_does_not_email_unsubscribed_member(ws_client_factory, monkeypatch):
+    calls = _fake_smtp(monkeypatch)
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+    room = instance1.post("/api/rooms", json={"name": _unique("general")}).json()
+    instance2.post(f"/api/rooms/{room['id']}/join")
+    # bob never opts in -- email_notifications defaults to False.
+
+    with instance1.websocket_connect("/ws/chat") as alice_ws:
+        alice_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert alice_ws.receive_json()["type"] == "joined"
+        _send_and_sync(alice_ws, room["id"], f"hey @{bob['username']}")
+
+    assert calls == []
+
+
+def test_room_message_does_not_email_online_subscribed_member(ws_client_factory, monkeypatch):
+    calls = _fake_smtp(monkeypatch)
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+    room = instance1.post("/api/rooms", json={"name": _unique("general")}).json()
+    instance2.post(f"/api/rooms/{room['id']}/join")
+    _subscribe(instance2, room["id"], bob["username"])
+
+    with instance2.websocket_connect("/ws/chat"):
+        # bob has an open connection -- genuinely online -- even though he
+        # never joins this room's own channel.
+        with instance1.websocket_connect("/ws/chat") as alice_ws:
+            alice_ws.send_json({"type": "join", "room_id": room["id"]})
+            assert alice_ws.receive_json()["type"] == "joined"
+            _send_and_sync(alice_ws, room["id"], f"hey @{bob['username']}")
+
+    assert calls == []
+
+
+def test_room_notifications_reset_after_read(ws_client_factory, monkeypatch):
+    calls = _fake_smtp(monkeypatch)
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+    room = instance1.post("/api/rooms", json={"name": _unique("general")}).json()
+    instance2.post(f"/api/rooms/{room['id']}/join")
+    _subscribe(instance2, room["id"], bob["username"])
+
+    with instance1.websocket_connect("/ws/chat") as alice_ws:
+        alice_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert alice_ws.receive_json()["type"] == "joined"
+        _send_and_sync(alice_ws, room["id"], "message one")
+        assert len(calls) == 1
+
+    instance2.post(
+        "/api/auth/login", json={"username_or_email": bob["username"], "password": "password123"}
+    )
+    read_resp = instance2.post(f"/api/rooms/{room['id']}/read")
+    assert read_resp.status_code == 204
+
+    with instance1.websocket_connect("/ws/chat") as alice_ws:
+        alice_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert alice_ws.receive_json()["type"] == "joined"
+        _send_and_sync(alice_ws, room["id"], "message two")
+
+    assert len(calls) == 2
+
+
+def test_enabling_notifications_rejected_for_dm(ws_client_factory):
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+    dm = instance1.post("/api/rooms/dm", json={"other_user_id": bob["id"]}).json()
+
+    resp = instance1.patch(f"/api/rooms/{dm['id']}/notifications", json={"email_notifications": True})
+    assert resp.status_code == 400
+
+
+def test_notifications_setting_reflected_in_my_rooms(ws_client_factory):
+    instance1 = ws_client_factory()
+    _register_ws(instance1, _unique("alice"))
+    room = instance1.post("/api/rooms", json={"name": _unique("general")}).json()
+
+    rooms = instance1.get("/api/rooms/mine").json()
+    mine = next(r for r in rooms if r["id"] == room["id"])
+    assert mine["email_notifications"] is False
+
+    resp = instance1.patch(f"/api/rooms/{room['id']}/notifications", json={"email_notifications": True})
+    assert resp.status_code == 204
+
+    rooms = instance1.get("/api/rooms/mine").json()
+    mine = next(r for r in rooms if r["id"] == room["id"])
+    assert mine["email_notifications"] is True

backend/tests/test_rooms.py

@@ -1,11 +1,52 @@
+import io
 import uuid
 
+from PIL import Image
 from sqlalchemy import select
 
-from app.models import Room, RoomMembership, RoomRole, User
+from app.models import (
+    EventSubscription,
+    MessageFile,
+    MessageImage,
+    MessageRoomReference,
+    Room,
+    RoomMembership,
+    RoomRole,
+    User,
+    WebhookIncoming,
+)
+from app.schemas.user import UserCreate
+from app.services.auth_service import register_user
+from app.storage import UPLOADS_DIR
 from tests.conftest import login_as, register_and_login
 
 
+def _unique(prefix: str) -> str:
+    return f"{prefix}-{uuid.uuid4().hex[:8]}"
+
+
+def _png_bytes() -> bytes:
+    buf = io.BytesIO()
+    Image.new("RGB", (10, 10), color=(255, 0, 0)).save(buf, format="PNG")
+    return buf.getvalue()
+
+
+def _register_ws(ws_client, username: str) -> dict:
+    async def _seed():
+        async with ws_client.session_factory() as session:
+            await register_user(
+                session,
+                UserCreate(username=username, email=f"{username}@example.com", password="password123"),
+            )
+
+    ws_client.portal.call(_seed)
+    resp = ws_client.post(
+        "/api/auth/login", json={"username_or_email": username, "password": "password123"}
+    )
+    assert resp.status_code == 200, resp.text
+    return resp.json()
+
+
 async def test_create_room_requires_auth(client):
     resp = await client.post("/api/rooms", json={"name": "general"})
     assert resp.status_code == 401
@@ -210,6 +251,88 @@ async def test_delete_room_owner_only(client, db_session):
     assert result.scalar_one_or_none() is None
 
 
+def test_delete_room_with_attachments_integrations_and_cross_room_reference(ws_client):
+    # Reproduces #55: every table below has a room_id (or message_id, for a
+    # room being deleted) foreign key with no ON DELETE CASCADE at the DB
+    # level, so a room that's ever had an attachment, an integration, or
+    # been #referenced from another room's message used to 500 on delete.
+    # This sets up one of each and confirms delete_room cleans all of them
+    # up, not just whichever one originally surfaced the bug.
+    _register_ws(ws_client, _unique("alice"))
+    target_name = _unique("target-room")
+    other_name = _unique("other-room")
+    target = ws_client.post("/api/rooms", json={"name": target_name}).json()
+    other = ws_client.post("/api/rooms", json={"name": other_name}).json()
+
+    image_id = ws_client.post(
+        f"/api/rooms/{target['id']}/images",
+        files={"file": ("test.png", _png_bytes(), "image/png")},
+    ).json()["id"]
+    file_upload = ws_client.post(
+        f"/api/rooms/{target['id']}/files",
+        files={"file": ("report.pdf", b"%PDF-1.4 not real", "application/pdf")},
+    ).json()
+    file_id = file_upload["id"]
+
+    webhook = ws_client.post(f"/api/rooms/{target['id']}/webhooks/incoming", json={}).json()
+    sub = ws_client.post(
+        f"/api/rooms/{target['id']}/event-subscriptions",
+        json={"event_types": ["message.created"], "target_url": "http://8.8.8.8/hook"},
+    ).json()
+
+    with ws_client.websocket_connect("/ws/chat") as ws:
+        ws.send_json({"type": "join", "room_id": target["id"]})
+        assert ws.receive_json()["type"] == "joined"
+        ws.send_json({"type": "message", "room_id": target["id"], "image_id": image_id})
+        ws.receive_json()
+        ws.send_json({"type": "message", "room_id": target["id"], "file_id": file_id})
+        ws.receive_json()
+
+        ws.send_json({"type": "join", "room_id": other["id"]})
+        assert ws.receive_json()["type"] == "joined"
+        # References target-room from a message that belongs to a
+        # *different* room -- the direction that originally 500'd, since
+        # it's keyed by the referenced room's id, not the message's room.
+        ws.send_json({"type": "message", "room_id": other["id"], "content": f"check out #{target_name}"})
+        other_message = ws.receive_json()
+
+    async def _storage_filenames():
+        async with ws_client.session_factory() as session:
+            image = await session.get(MessageImage, uuid.UUID(image_id))
+            file = await session.get(MessageFile, uuid.UUID(file_id))
+            return image.storage_filename, file.storage_filename
+
+    image_filename, file_filename = ws_client.portal.call(_storage_filenames)
+    assert (UPLOADS_DIR / image_filename).exists()
+    assert (UPLOADS_DIR / file_filename).exists()
+
+    resp = ws_client.delete(f"/api/rooms/{target['id']}")
+    assert resp.status_code == 204, resp.text
+
+    async def _assert_cleaned_up():
+        async with ws_client.session_factory() as session:
+            target_id = uuid.UUID(target["id"])
+            for model in (MessageImage, MessageFile, WebhookIncoming, EventSubscription):
+                result = await session.execute(select(model).where(model.room_id == target_id))
+                assert result.scalar_one_or_none() is None, model.__name__
+            result = await session.execute(
+                select(MessageRoomReference).where(MessageRoomReference.room_id == target_id)
+            )
+            assert result.scalar_one_or_none() is None
+
+    ws_client.portal.call(_assert_cleaned_up)
+
+    # The physical files were unlinked too, not just the DB rows.
+    assert not (UPLOADS_DIR / image_filename).exists()
+    assert not (UPLOADS_DIR / file_filename).exists()
+
+    # Sanity: deleting target-room didn't touch the unrelated other-room or
+    # its message -- the cross-room reference cleanup is scoped correctly.
+    history = ws_client.get(f"/api/rooms/{other['id']}/messages").json()
+    assert any(m["id"] == other_message["id"] for m in history)
+    assert webhook["id"] and sub["id"]  # created successfully, not otherwise asserted above
+
+
 async def test_leave_room(client, db_session):
     await register_and_login(client, db_session, username="alice")
     room_id = (await client.post("/api/rooms", json={"name": "general"})).json()["id"]
@@ -327,8 +450,8 @@ async def test_change_member_role_owner_only(client, db_session):
 def _fake_send_email(monkeypatch):
     calls = []
 
-    async def fake(db, to, subject, body):
+    async def fake(db, to, subject, paragraphs, **kwargs):
-        calls.append({"to": to, "subject": subject, "body": body})
+        calls.append({"to": to, "subject": subject, "paragraphs": paragraphs, **kwargs})
 
     monkeypatch.setattr("app.services.room_service.send_email", fake)
     return calls
@@ -361,6 +484,27 @@ async def test_add_member_directly(client, db_session, monkeypatch):
     assert "added" in calls[0]["subject"].lower()
 
 
+async def test_add_member_posts_welcome_message(client, db_session, monkeypatch):
+    # #74: posted as the auto-provisioned "system" account, not the admin
+    # who added them -- mirrors test_add_member_directly's setup.
+    _fake_send_email(monkeypatch)
+    await register_and_login(client, db_session, username="alice")
+    room_id = (await client.post("/api/rooms", json={"name": "general"})).json()["id"]
+
+    await client.post("/api/auth/logout")
+    bob = await register_and_login(client, db_session, username="bob")
+
+    await client.post("/api/auth/logout")
+    await login_as(client, "alice")
+    resp = await client.post(f"/api/rooms/{room_id}/members", json={"user_id": bob["id"]})
+    assert resp.status_code == 201, resp.text
+
+    history = (await client.get(f"/api/rooms/{room_id}/messages")).json()
+    welcome_messages = [m for m in history if m["username"] == "system"]
+    assert len(welcome_messages) == 1
+    assert welcome_messages[0]["content"] == "Welcome to #general, bob!"
+
+
 async def test_add_member_requires_admin_role(client, db_session, monkeypatch):
     _fake_send_email(monkeypatch)
     await register_and_login(client, db_session, username="alice")

backend/tests/test_sessions.py

@@ -0,0 +1,112 @@
+import uuid
+
+from httpx import ASGITransport, AsyncClient
+
+from app.schemas.user import UserCreate
+from app.services.auth_service import register_user
+from tests.conftest import login_as, register_and_login
+
+
+def _unique(prefix: str) -> str:
+    return f"{prefix}-{uuid.uuid4().hex[:8]}"
+
+
+async def test_login_creates_a_session(client, db_session):
+    username = _unique("alice")
+    await register_user(
+        db_session, UserCreate(username=username, email=f"{username}@example.com", password="password123")
+    )
+    resp = await client.post(
+        "/api/auth/login",
+        json={"username_or_email": username, "password": "password123"},
+        headers={"User-Agent": "Mozilla/5.0 (Windows NT 10.0; Win64; x64) Chrome/120.0 Safari/537.36"},
+    )
+    assert resp.status_code == 200, resp.text
+
+    sessions = (await client.get("/api/auth/sessions")).json()
+    assert len(sessions) == 1
+    assert sessions[0]["is_current"] is True
+    assert sessions[0]["device_label"] == "Chrome on Windows"
+    assert sessions[0]["ip_address"]
+
+
+async def test_logout_revokes_the_session(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+    assert len((await client.get("/api/auth/sessions")).json()) == 1
+
+    await client.post("/api/auth/logout")
+    # The important part is server-side: the session row itself is gone
+    # from the active list (this request also 401s since this client's own
+    # cookie was cleared, but that alone wouldn't prove the *row* is dead).
+    resp = await client.get("/api/auth/sessions")
+    assert resp.status_code == 401
+
+
+async def test_x_forwarded_for_takes_priority_over_direct_peer(client, db_session):
+    username = _unique("alice")
+    await register_user(
+        db_session, UserCreate(username=username, email=f"{username}@example.com", password="password123")
+    )
+    await client.post(
+        "/api/auth/login",
+        json={"username_or_email": username, "password": "password123"},
+        headers={"X-Forwarded-For": "203.0.113.7, 10.0.0.1"},
+    )
+
+    sessions = (await client.get("/api/auth/sessions")).json()
+    assert sessions[0]["ip_address"] == "203.0.113.7"
+
+
+async def test_revoking_another_session_logs_it_out(client, app, db_session):
+    username = _unique("alice")
+    await register_and_login(client, db_session, username=username)
+
+    # A second "device" -- a separate client hitting the same app instance
+    # (so it shares the DB-override wiring), its own independent cookie.
+    async with AsyncClient(transport=ASGITransport(app=app), base_url="http://test") as other_device:
+        await login_as(other_device, username)
+        assert len((await other_device.get("/api/auth/sessions")).json()) == 2
+
+        mine = (await client.get("/api/auth/sessions")).json()
+        assert len(mine) == 2
+        not_current = next(s for s in mine if not s["is_current"])
+
+        revoke = await client.delete(f"/api/auth/sessions/{not_current['id']}")
+        assert revoke.status_code == 204
+
+        # The other device's own cookie is now dead.
+        resp = await other_device.get("/api/auth/sessions")
+        assert resp.status_code == 401
+
+    # And the revoked session no longer shows up for the account at all.
+    remaining = (await client.get("/api/auth/sessions")).json()
+    assert len(remaining) == 1
+    assert remaining[0]["is_current"] is True
+
+
+async def test_cannot_revoke_another_users_session(client, app, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+    my_session_id = (await client.get("/api/auth/sessions")).json()[0]["id"]
+
+    async with AsyncClient(transport=ASGITransport(app=app), base_url="http://test") as bob_client:
+        await register_and_login(bob_client, db_session, username=_unique("bob"))
+        resp = await bob_client.delete(f"/api/auth/sessions/{my_session_id}")
+        assert resp.status_code == 404
+
+    # Untouched -- still exactly one active session for alice.
+    assert len((await client.get("/api/auth/sessions")).json()) == 1
+
+
+async def test_revoking_own_current_session_works_then_logs_this_client_out(client, db_session):
+    await register_and_login(client, db_session, username=_unique("alice"))
+    session_id = (await client.get("/api/auth/sessions")).json()[0]["id"]
+
+    # Revoking your own *current* session is allowed (a remote sign-out of
+    # this same device is a legitimate, if odd, thing to do).
+    first = await client.delete(f"/api/auth/sessions/{session_id}")
+    assert first.status_code == 204
+
+    # A second call with the same (now-dead) cookie can't even reach the
+    # revoke check -- get_current_user itself already 401s.
+    second = await client.delete(f"/api/auth/sessions/{session_id}")
+    assert second.status_code == 401

backend/tests/test_site_invites.py

@@ -43,6 +43,14 @@ def _extract_token(body: str) -> str:
     return match.group(1)
 
 
+def _plain_text(message) -> str:
+    # #68: the email is now multipart/alternative (HTML + plain-text
+    # fallback) -- .get_content() has no handler for a multipart message
+    # itself, get_body(preferencelist=...) is the standard way to reach a
+    # specific alternative part.
+    return message.get_body(preferencelist=("plain",)).get_content()
+
+
 async def test_create_site_invite_requires_admin(client, db_session):
     await register_and_login(client, db_session, username="alice")
     resp = await client.post("/api/admin/invites", json={"email": "newperson@example.com"})
@@ -62,7 +70,7 @@ async def test_signup_flow_end_to_end(client, db_session, monkeypatch):
     assert invite["status"] == "pending"
 
     assert len(calls) == 1
-    token = _extract_token(calls[0]["message"].get_content())
+    token = _extract_token(_plain_text(calls[0]["message"]))
 
     validate = await client.get(f"/api/signup/validate?token={token}")
     assert validate.status_code == 200
@@ -87,7 +95,7 @@ async def test_signup_rejects_mismatched_password_confirmation(client, db_sessio
     await _configure_smtp(client)
 
     await client.post("/api/admin/invites", json={"email": "typo@example.com"})
-    token = _extract_token(calls[0]["message"].get_content())
+    token = _extract_token(_plain_text(calls[0]["message"]))
 
     complete = await client.post(
         "/api/signup",
@@ -127,7 +135,7 @@ async def test_expired_token_rejected(client, db_session, monkeypatch):
 
     resp = await client.post("/api/admin/invites", json={"email": "late@example.com"})
     invite_id = resp.json()["id"]
-    token = _extract_token(calls[0]["message"].get_content())
+    token = _extract_token(_plain_text(calls[0]["message"]))
 
     db_invite = await db_session.get(SiteInvite, uuid.UUID(invite_id))
     db_invite.expires_at = datetime.now(timezone.utc) - timedelta(days=1)
@@ -147,7 +155,7 @@ async def test_used_token_cannot_be_reused(client, db_session, monkeypatch):
     await _configure_smtp(client)
 
     await client.post("/api/admin/invites", json={"email": "once@example.com"})
-    token = _extract_token(calls[0]["message"].get_content())
+    token = _extract_token(_plain_text(calls[0]["message"]))
 
     first = await client.post(
         "/api/signup",
@@ -170,7 +178,7 @@ async def test_revoke_site_invite_prevents_signup(client, db_session, monkeypatc
 
     resp = await client.post("/api/admin/invites", json={"email": "revoked@example.com"})
     invite_id = resp.json()["id"]
-    token = _extract_token(calls[0]["message"].get_content())
+    token = _extract_token(_plain_text(calls[0]["message"]))
 
     revoke = await client.delete(f"/api/admin/invites/{invite_id}")
     assert revoke.status_code == 200
@@ -183,6 +191,79 @@ async def test_revoke_site_invite_prevents_signup(client, db_session, monkeypatc
     assert complete.status_code == 400
 
 
+async def test_resend_site_invite_requires_admin(client, db_session):
+    await register_and_login(client, db_session, username="alice")
+    resp = await client.post(f"/api/admin/invites/{uuid.uuid4()}/resend")
+    assert resp.status_code == 403
+
+
+async def test_resend_site_invite_unknown_id_404s(client, db_session):
+    admin = await register_and_login(client, db_session, username="admin1")
+    await _make_admin(db_session, admin["id"])
+    resp = await client.post(f"/api/admin/invites/{uuid.uuid4()}/resend")
+    assert resp.status_code == 404
+
+
+async def test_resend_site_invite_new_link_works_and_old_one_doesnt(client, db_session, monkeypatch):
+    calls = _fake_smtp(monkeypatch)
+    admin = await register_and_login(client, db_session, username="admin1")
+    await _make_admin(db_session, admin["id"])
+    await _configure_smtp(client)
+
+    resp = await client.post("/api/admin/invites", json={"email": "resend-me@example.com"})
+    invite_id = resp.json()["id"]
+    original_expires_at = datetime.fromisoformat(resp.json()["expires_at"])
+    old_token = _extract_token(_plain_text(calls[0]["message"]))
+
+    resend = await client.post(f"/api/admin/invites/{invite_id}/resend")
+    assert resend.status_code == 200, resend.text
+    assert resend.json()["id"] == invite_id
+    assert resend.json()["status"] == "pending"
+    # A fresh 7-day window, not whatever was left on the original.
+    new_expires_at = datetime.fromisoformat(resend.json()["expires_at"])
+    assert new_expires_at > original_expires_at
+
+    assert len(calls) == 2
+    new_token = _extract_token(_plain_text(calls[1]["message"]))
+    assert new_token != old_token
+
+    # The old link is dead -- resending rotates the token, it doesn't just
+    # repeat it.
+    old_validate = await client.get(f"/api/signup/validate?token={old_token}")
+    assert old_validate.status_code == 400
+
+    new_validate = await client.get(f"/api/signup/validate?token={new_token}")
+    assert new_validate.status_code == 200
+    assert new_validate.json()["email"] == "resend-me@example.com"
+
+    complete = await client.post(
+        "/api/signup",
+        json={
+            "token": new_token,
+            "username": "resentuser",
+            "password": "password123",
+            "password_confirm": "password123",
+        },
+    )
+    assert complete.status_code == 200, complete.text
+
+
+async def test_resend_site_invite_rejects_non_pending(client, db_session, monkeypatch):
+    _fake_smtp(monkeypatch)
+    admin = await register_and_login(client, db_session, username="admin1")
+    await _make_admin(db_session, admin["id"])
+    await _configure_smtp(client)
+
+    resp = await client.post("/api/admin/invites", json={"email": "already-revoked@example.com"})
+    invite_id = resp.json()["id"]
+
+    revoke = await client.delete(f"/api/admin/invites/{invite_id}")
+    assert revoke.status_code == 200
+
+    resend = await client.post(f"/api/admin/invites/{invite_id}/resend")
+    assert resend.status_code == 400
+
+
 async def test_list_site_invites(client, db_session, monkeypatch):
     _fake_smtp(monkeypatch)
     admin = await register_and_login(client, db_session, username="admin1")
@@ -194,3 +275,54 @@ async def test_list_site_invites(client, db_session, monkeypatch):
     assert resp.status_code == 200
     emails = [i["email"] for i in resp.json()]
     assert "listed@example.com" in emails
+
+
+async def test_list_site_invites_excludes_revoked_invite(client, db_session, monkeypatch):
+    # #61: the admin UI labels this list "Pending invites" -- a revoked
+    # invite has nothing left to act on and must actually drop out of it,
+    # not just get relabeled in place.
+    _fake_smtp(monkeypatch)
+    admin = await register_and_login(client, db_session, username="admin1")
+    await _make_admin(db_session, admin["id"])
+    await _configure_smtp(client)
+
+    resp = await client.post("/api/admin/invites", json={"email": "revoked-from-list@example.com"})
+    invite_id = resp.json()["id"]
+
+    revoke = await client.delete(f"/api/admin/invites/{invite_id}")
+    assert revoke.status_code == 200
+
+    listed = await client.get("/api/admin/invites")
+    emails = [i["email"] for i in listed.json()]
+    assert "revoked-from-list@example.com" not in emails
+
+
+async def test_list_site_invites_excludes_accepted_invite(client, db_session, monkeypatch):
+    # Same gap, the other trigger: completing signup accepts the invite
+    # out-of-band from the admin's own session, but it must still be gone
+    # from the pending list on the admin's next fetch.
+    calls = _fake_smtp(monkeypatch)
+    admin = await register_and_login(client, db_session, username="admin1")
+    await _make_admin(db_session, admin["id"])
+    await _configure_smtp(client)
+
+    await client.post("/api/admin/invites", json={"email": "accepted-from-list@example.com"})
+    token = _extract_token(_plain_text(calls[0]["message"]))
+
+    complete = await client.post(
+        "/api/signup",
+        json={
+            "token": token,
+            "username": "acceptedfromlist",
+            "password": "password123",
+            "password_confirm": "password123",
+        },
+    )
+    assert complete.status_code == 200, complete.text
+
+    # Signup logs the new user's session in on `client` -- switch back to
+    # the admin to check the list the way the admin actually would.
+    await login_as(client, "admin1")
+    listed = await client.get("/api/admin/invites")
+    emails = [i["email"] for i in listed.json()]
+    assert "accepted-from-list@example.com" not in emails

backend/tests/test_system_user.py

@@ -0,0 +1,13 @@
+from app.services.system_user_service import SYSTEM_USERNAME, get_or_create_system_user
+
+
+async def test_get_or_create_system_user_creates_bot_account(db_session):
+    user = await get_or_create_system_user(db_session)
+    assert user.username == SYSTEM_USERNAME
+    assert user.is_bot is True
+
+
+async def test_get_or_create_system_user_is_idempotent(db_session):
+    first = await get_or_create_system_user(db_session)
+    second = await get_or_create_system_user(db_session)
+    assert first.id == second.id

deploy/upgrade.sh

@@ -16,9 +16,18 @@ BACKEND_DIR="${REPO_DIR}/backend"
 FRONTEND_DIR="${REPO_DIR}/frontend"
 ENV_FILE="/etc/ds-chat/env"
 
-echo "==> Pulling latest code"
+echo "==> Fetching latest release"
 cd "$REPO_DIR"
-git pull --ff-only
+git fetch --tags --force
+LATEST_TAG="$(git tag --sort=-creatordate | head -n1)"
+if [[ -z "$LATEST_TAG" ]]; then
+  echo "No tags found -- nothing to deploy" >&2
+  exit 1
+fi
+echo "Deploying $LATEST_TAG"
+# Detached HEAD, not a branch checkout -- this directory only ever runs a
+# tagged release, never whatever the default branch's tip happens to be.
+git checkout --quiet --detach "$LATEST_TAG"
 
 echo "==> Installing backend dependencies"
 cd "$BACKEND_DIR"

frontend/.env.example

@@ -0,0 +1,7 @@
+# Shown as the "Source code" link in the app's About screen -- required
+# for AGPL-3.0 section 13 compliance once you deploy this (a link so users
+# interacting with the app over the network can get the actual source,
+# including any modifications you've made). The default below points at
+# the upstream project -- fine if you're running it unmodified, but if
+# you've forked or patched the code, point this at *your* copy instead.
+VITE_SOURCE_URL=https://github.com/ds-ksmith/DS-Chat

frontend/README.md

@@ -1,13 +1,15 @@
 # DS Chat frontend
 
 React 19 + TypeScript + Vite PWA. The full client for DS Chat: auth and
-invite-based signup, room CRUD with roles/invites, real-time WebSocket chat
+invite-based signup, room CRUD with roles/invites, direct messages,
-(Markdown, @mentions, reactions, image/file attachments with previews,
+real-time WebSocket chat (Markdown, @mentions, reactions, built-in and
-message editing), unread indicators and presence, per-user theming
+custom emoji, image/video/file attachments with previews, message editing
-(presets plus a custom theme builder), Web Push notifications, offline
+and deletion), unread indicators and presence, per-user theming (presets
-caching and an auto-update banner via a custom service worker, and a
+plus a custom theme builder), Web Push/email notifications and a desktop-
-site-admin portal — wired to the backend's REST API and `/ws/chat` WebSocket
+notification bridge, an active-sessions view for managing where you're
-endpoint. See [`../README.md`](../README.md) and
+logged in, offline caching and an auto-update banner via a custom service
+worker, and a site-admin portal — wired to the backend's REST API and
+`/ws/chat` WebSocket endpoint. See [`../README.md`](../README.md) and
 [`../backend/README.md`](../backend/README.md) for full local setup.
 
 ## Dev
@@ -39,20 +41,24 @@ worker.
 ```
 src/
   main.tsx, App.tsx        routes: /login, /signup, /forgot-password, /reset-password,
-                             /rooms, /rooms/:roomId, /admin (AdminRoute-gated); mounts
+                             /rooms, /rooms/:roomId, /admin (AdminRoute-gated), /help;
-                             UpdateBanner globally and ChatSocketProvider once authed
+                             mounts UpdateBanner globally, ChatSocketProvider and
+                             CustomEmojiProvider once authed
   types.ts                  shared request/response/WS-envelope types, mirroring the
                              backend's Pydantic schemas
 
   api/                      fetch wrappers, one file per backend resource: client
-                              (base fetch/error handling), auth, signup, rooms, users,
+                              (base fetch/error handling), auth (incl. active sessions),
-                              bots, webhooks, push, admin, customThemes, uploads
+                              signup, rooms (incl. DMs), users, bots, webhooks, push,
+                              admin, customThemes, customEmoji, uploads
   ws/useChatSocket.ts        the WebSocket hook: connect/reconnect with backoff,
-                              join/leave rooms, send/edit/react, visibility-gated
+                              join/leave rooms, send/edit/delete/react, visibility-gated
                               presence, triggers an SW update check on reconnect
   context/
     AuthContext.tsx            current-user state, hydrated via GET /api/auth/me
     ChatSocketContext.tsx      shares one useChatSocket instance across the app
+    CustomEmojiContext.tsx     fetches the site's custom emoji once, exposes a
+                                 shortcode lookup + a refresh() called after upload/delete
 
   lib/
     avatar.ts                  deterministic accent-color cycling for avatars
@@ -61,7 +67,9 @@ src/
     fileSize.ts                 human-readable byte formatting
     lastUser.ts                 cached "who was I last logged in as" for offline shell render
     messageGrouping.ts          groups consecutive messages by sender/time, presence lookup
-    push.ts                     PushManager subscribe/unsubscribe, VAPID key conversion
+    push.ts                     PushManager subscribe/unsubscribe, VAPID key conversion,
+                                  timeout-guarded so a browser that never settles the
+                                  permission prompt can't leave the UI stuck forever
     swUpdate.ts                  bridges the SW registration to useChatSocket's reconnect hook
     theme.ts                     applies preset/custom themes as CSS custom properties
 
@@ -73,26 +81,38 @@ src/
 
   components/
     ProtectedRoute.tsx, AdminRoute.tsx        auth/site-admin route guards
-    TopBar.tsx, Sidebar.tsx, RoomRow.tsx        room list chrome
+    TopBar.tsx, Sidebar.tsx, RoomRow.tsx        room list chrome (DMs and Rooms as
+                                                  independently collapsible sections)
     ChatPane.tsx, MessageList.tsx, Composer.tsx    chat view: history+live merge,
-                                                     message rendering, composer/attach/send
+                                                     message rendering (incl. deleted-message
-    MessageContent.tsx, MentionAutocomplete.tsx    Markdown rendering + @mention highlighting/autocomplete
+                                                     tombstones), composer/attach/send
-    ImageLightbox.tsx, FilePreviewModal.tsx        attachment viewers (image/PDF/text/Markdown)
+    MessageContent.tsx, MentionAutocomplete.tsx    Markdown rendering (mentions, room
-    EmojiPicker.tsx                                reaction/composer emoji picker
+                                                     links, custom emoji `:shortcode:`,
-    RoomInfoPanel.tsx                              room details/members/roles panel
+                                                     heading ids, sub/superscript) +
-    NewRoomModal.tsx, BrowseRoomsModal.tsx, UserPicker.tsx    room creation/discovery, member picking
+                                                     @mention highlighting/autocomplete
+    ImageLightbox.tsx, VideoLightbox.tsx,
+    FilePreviewModal.tsx                           attachment viewers (image/video/PDF/
+                                                     text/Markdown)
+    EmojiPicker.tsx, CustomEmojiUploadModal.tsx     reaction/composer emoji picker
+                                                      (built-in + site's custom emoji) and
+                                                      its upload dialog
+    RoomInfoPanel.tsx                              room details/members/roles/email-
+                                                     notification-toggle panel
+    NewRoomModal.tsx, BrowseRoomsModal.tsx, UserPicker.tsx    room creation/discovery, member
+                                                                picking (also how a DM starts)
     ProfileModal.tsx, ThemeBuilderModal.tsx, CustomThemePreview.tsx
-                                                    profile settings + the custom theme editor
+                                                    profile settings (incl. active-sessions
-                                                    (opened in its own wide dialog) with a live,
+                                                    list) + the custom theme editor (opened
+                                                    in its own wide dialog) with a live,
                                                     hoverable mockup of the real UI
     RoomAvatar.tsx, UserAvatar.tsx                 avatar rendering (incl. presence dot)
     OfflineBanner.tsx, UpdateBanner.tsx            connectivity state / new-version-available prompt
 
   pages/
     LoginPage.tsx, SignupPage.tsx, ForgotPasswordPage.tsx, ResetPasswordPage.tsx
-    ChatShellPage.tsx, AdminPage.tsx
+    ChatShellPage.tsx, AdminPage.tsx, HelpPage.tsx
 
-  styles/tokens.css          design tokens (DarkSingularity theme: colors, spacing, etc.)
+  styles/tokens.css          design tokens (default theme: colors, spacing, etc.)
   sw.ts                      custom service worker (injectManifest): app-shell
                                precache + NetworkFirst runtime caching, push/notificationclick
                                handlers, SKIP_WAITING messaging for the update-prompt flow

frontend/index.html

@@ -2,7 +2,7 @@
 <html lang="en">
   <head>
     <meta charset="UTF-8" />
-    <link rel="icon" type="image/svg+xml" href="/favicon.svg" />
+    <link rel="icon" type="image/png" href="/favicon.png" />
     <meta name="viewport" content="width=device-width, initial-scale=1.0" />
     <title>DS Chat</title>
   </head>

frontend/package.json

@@ -1,7 +1,7 @@
 {
   "name": "frontend",
   "private": true,
-  "version": "1.0.0",
+  "version": "2026.9.4",
   "license": "AGPL-3.0-or-later",
   "type": "module",
   "scripts": {

frontend/src/App.tsx

@@ -1,6 +1,7 @@
 import { Navigate, Route, Routes } from 'react-router-dom'
 import { AuthProvider, useAuth } from './context/AuthContext'
 import { ChatSocketProvider } from './context/ChatSocketContext'
+import { CustomEmojiProvider } from './context/CustomEmojiContext'
 import { AdminRoute } from './components/AdminRoute'
 import { DesktopNotificationBridge } from './components/DesktopNotificationBridge'
 import { ProtectedRoute } from './components/ProtectedRoute'
@@ -67,8 +68,10 @@ function AppRoutes() {
   if (!user) return routes
   return (
     <ChatSocketProvider key={user.id}>
+      <CustomEmojiProvider>
         <DesktopNotificationBridge />
         {routes}
+      </CustomEmojiProvider>
     </ChatSocketProvider>
   )
 }

frontend/src/api/admin.ts

@@ -83,6 +83,13 @@ export function revokeSiteInvite(inviteId: string): Promise<SiteInvite> {
   return apiFetch<SiteInvite>(`/api/admin/invites/${inviteId}`, { method: 'DELETE' })
 }
 
+// #60: same invite row, not a new one -- a fresh token/expiry, and the old
+// link stops working the moment this is called (see the backend's own
+// resend_site_invite for why).
+export function resendSiteInvite(inviteId: string): Promise<SiteInvite> {
+  return apiFetch<SiteInvite>(`/api/admin/invites/${inviteId}/resend`, { method: 'POST' })
+}
+
 export function getSmtpSettings(): Promise<SmtpSettings | null> {
   return apiFetch<SmtpSettings | null>('/api/admin/settings/smtp')
 }

frontend/src/api/auth.ts

@@ -1,5 +1,5 @@
 import { apiFetch, ApiError, NetworkError } from './client'
-import type { User } from '../types'
+import type { EmojiScale, TextScale, User, UserSession } from '../types'
 
 // No register() here: this is an invite-only site. Accounts are created by
 // an operator via the backend CLI (`python -m app.cli create-user`), not
@@ -16,6 +16,16 @@ export function logout(): Promise<void> {
   return apiFetch<void>('/api/auth/logout', { method: 'POST' })
 }
 
+// #69: every device/browser currently logged into this account, newest
+// last-seen first -- see backend's app/schemas/session.py.
+export function listSessions(): Promise<UserSession[]> {
+  return apiFetch<UserSession[]>('/api/auth/sessions')
+}
+
+export function revokeSession(sessionId: string): Promise<void> {
+  return apiFetch<void>(`/api/auth/sessions/${sessionId}`, { method: 'DELETE' })
+}
+
 export function me(): Promise<User> {
   return apiFetch<User>('/api/auth/me')
 }
@@ -40,6 +50,23 @@ export function updateTheme(theme: 'dark' | 'light' | 'midnight' | 'sunset'): Pr
   })
 }
 
+// #71: its own call, same reasoning as updateTheme above -- the backend
+// only applies fields actually present in the request body, so this can't
+// clobber theme (or vice versa).
+export function updateTextScale(textScale: TextScale): Promise<User> {
+  return apiFetch<User>('/api/auth/me', {
+    method: 'PATCH',
+    body: JSON.stringify({ text_scale: textScale }),
+  })
+}
+
+export function updateEmojiScale(emojiScale: EmojiScale): Promise<User> {
+  return apiFetch<User>('/api/auth/me', {
+    method: 'PATCH',
+    body: JSON.stringify({ emoji_scale: emojiScale }),
+  })
+}
+
 export function removeAvatar(): Promise<User> {
   return apiFetch<User>('/api/auth/me/avatar', { method: 'DELETE' })
 }

frontend/src/api/customEmoji.ts

@@ -0,0 +1,47 @@
+import { apiFetch, ApiError, NetworkError } from './client'
+import type { CustomEmoji } from '../types'
+
+export function listCustomEmoji(): Promise<CustomEmoji[]> {
+  return apiFetch<CustomEmoji[]>('/api/custom-emoji')
+}
+
+export function getCustomEmojiUrl(shortcode: string): string {
+  return `/api/custom-emoji/${encodeURIComponent(shortcode)}/image`
+}
+
+export function deleteCustomEmoji(id: string): Promise<void> {
+  return apiFetch<void>(`/api/custom-emoji/${id}`, { method: 'DELETE' })
+}
+
+// Raw fetch, not apiFetch -- same multipart-boundary reason as
+// uploadAvatar/uploadRoomImage (a manually-set Content-Type header would
+// omit the boundary the browser generates for FormData).
+export async function uploadCustomEmoji(shortcode: string, file: File): Promise<CustomEmoji> {
+  const formData = new FormData()
+  formData.append('shortcode', shortcode)
+  formData.append('file', file)
+
+  let response: Response
+  try {
+    response = await fetch('/api/custom-emoji', {
+      method: 'POST',
+      credentials: 'include',
+      body: formData,
+    })
+  } catch {
+    throw new NetworkError()
+  }
+
+  if (!response.ok) {
+    let detail = response.statusText
+    try {
+      const body = await response.json()
+      detail = body.detail ?? detail
+    } catch {
+      // response had no JSON body
+    }
+    throw new ApiError(response.status, detail)
+  }
+
+  return (await response.json()) as CustomEmoji
+}

frontend/src/api/rooms.ts

@@ -29,6 +29,15 @@ export function createRoom(
   })
 }
 
+// #52: find-or-create -- returns the existing DM with this person if one
+// already exists, rather than always creating a new room.
+export function startDm(otherUserId: string): Promise<Room> {
+  return apiFetch<Room>('/api/rooms/dm', {
+    method: 'POST',
+    body: JSON.stringify({ other_user_id: otherUserId }),
+  })
+}
+
 export function updateRoom(
   roomId: string,
   data: { name?: string; description?: string; is_private?: boolean },
@@ -51,6 +60,25 @@ export function leaveRoom(roomId: string): Promise<void> {
   return apiFetch<void>(`/api/rooms/${roomId}/leave`, { method: 'POST' })
 }
 
+// #52 follow-up: only for DMs -- hides it from this user's own sidebar
+// without touching the other participant's copy. Reversible: messaging
+// again (startDm, above) or a new message from the other person un-hides
+// it automatically.
+export function hideDm(roomId: string): Promise<void> {
+  return apiFetch<void>(`/api/rooms/${roomId}/hide`, { method: 'POST' })
+}
+
+// #67: per-viewer opt-in for email on this room's first unread message
+// and every mention. 400s for a DM (backend rejects it -- see
+// set_room_email_notifications), so callers should only expose the
+// toggle for a non-DM room.
+export function updateRoomNotifications(roomId: string, emailNotifications: boolean): Promise<void> {
+  return apiFetch<void>(`/api/rooms/${roomId}/notifications`, {
+    method: 'PATCH',
+    body: JSON.stringify({ email_notifications: emailNotifications }),
+  })
+}
+
 export function listRoomMembers(roomId: string): Promise<RoomMember[]> {
   return apiFetch<RoomMember[]>(`/api/rooms/${roomId}/members`)
 }

frontend/src/components/AboutModal.tsx

@@ -10,8 +10,10 @@ interface AboutModalProps {
 // users remotely through a computer network, you should also make sure
 // that it provides a way for users to get its source... its interface
 // could display a 'Source' link" -- this modal is that link, not just a
-// courtesy credits screen.
+// courtesy credits screen. Deliberately not a hardcoded URL: whoever
-const SOURCE_URL = 'https://git.darksingularity.org/DarkSingularity/ds-chat'
+// deploys this needs to point it at *their* copy of the repo (including
+// any modifications), not the upstream project -- see frontend/.env.example.
+const SOURCE_URL = import.meta.env.VITE_SOURCE_URL as string | undefined
 
 export function AboutModal({ onClose }: AboutModalProps) {
   return (
@@ -39,11 +41,13 @@ export function AboutModal({ onClose }: AboutModalProps) {
           </a>
           .
         </p>
+        {SOURCE_URL && (
           <p className="about-modal-line">
             <a href={SOURCE_URL} target="_blank" rel="noopener noreferrer">
               Source code
             </a>
           </p>
+        )}
 
         <div className="modal-actions" style={{ marginTop: '1rem' }}>
           <button type="button" className="btn-secondary" onClick={onClose}>

frontend/src/components/ChatPane.tsx

@@ -171,6 +171,21 @@ export function ChatPane({
           setLive((prev) =>
             prev.map((m) => (m.id === envelope.id ? { ...m, reactions: envelope.reactions } : m)),
           )
+        } else if (envelope.type === 'message_deleted' && envelope.room_id === room.id) {
+          // Mirrors what the server already did to the row (see
+          // message_service.delete_message) -- content/image/file/preview
+          // cleared, deleted_at set. `reactions` is left alone; MessageList
+          // just doesn't render it once deleted_at is set, same as it
+          // doesn't render anything else here.
+          const tombstone = {
+            content: null,
+            image_id: null,
+            file: null,
+            link_preview: null,
+            deleted_at: new Date().toISOString(),
+          }
+          setHistory((prev) => prev.map((m) => (m.id === envelope.id ? { ...m, ...tombstone } : m)))
+          setLive((prev) => prev.map((m) => (m.id === envelope.id ? { ...m, ...tombstone } : m)))
         } else if (envelope.type === 'error') {
           setWsError(envelope.detail)
         }
@@ -212,6 +227,10 @@ export function ChatPane({
     (messageId: string, emoji: string) => socket.sendReaction(room.id, messageId, emoji),
     [socket, room.id],
   )
+  const sendDelete = useCallback(
+    (messageId: string) => socket.sendDelete(room.id, messageId),
+    [socket, room.id],
+  )
 
   return (
     <section className="chat-pane">
@@ -224,8 +243,16 @@ export function ChatPane({
           </button>
         )}
         <div className="chat-pane-title-block">
-          <div className="chat-pane-title">#{room.name}</div>
+          <div className="chat-pane-title">
-          <div className="chat-pane-subtitle">{members.length} member{members.length === 1 ? '' : 's'}</div>
+            {room.dm_partner ? room.dm_partner.display_name || room.dm_partner.username : `#${room.name}`}
+          </div>
+          <div className="chat-pane-subtitle">
+            {room.dm_partner
+              ? room.dm_partner.status === 'online'
+                ? 'Online'
+                : 'Offline'
+              : `${members.length} member${members.length === 1 ? '' : 's'}`}
+          </div>
         </div>
         <button
           type="button"
@@ -256,13 +283,16 @@ export function ChatPane({
         myRooms={myRooms}
         onEdit={sendEdit}
         onReact={sendReaction}
+        onDelete={sendDelete}
       />
       <Composer
         roomId={room.id}
-        roomName={room.name}
+        roomName={room.dm_partner ? room.dm_partner.display_name || room.dm_partner.username : room.name}
+        isDm={room.is_dm}
         members={members}
         rooms={rooms}
         disabled={!connected}
+        archived={room.is_archived}
         onSend={send}
       />
     </section>

frontend/src/components/Composer.tsx

@@ -12,9 +12,13 @@ import { useEscapeKey } from '../hooks/useEscapeKey'
 import { useOnlineStatus } from '../hooks/useOnlineStatus'
 import { uploadRoomFile, uploadRoomImage } from '../api/rooms'
 import { getUploadLimit } from '../api/uploads'
+import { useCustomEmoji } from '../context/CustomEmojiContext'
+import { EMOJI_SHORTCODES, SHORTCODE_BY_GLYPH } from '../lib/emojiShortcodes'
 import { formatFileSize } from '../lib/fileSize'
+import { getRecentEmoji, recordEmojiUsed } from '../lib/recentEmoji'
 import type { MyRoomItem, RoomMember } from '../types'
 import { EmojiPicker } from './EmojiPicker'
+import { EmojiShortcodeAutocomplete, type EmojiShortcodeMatch } from './EmojiShortcodeAutocomplete'
 import { MentionAutocomplete } from './MentionAutocomplete'
 import { RoomReferenceAutocomplete } from './RoomReferenceAutocomplete'
 import './Composer.css'
@@ -22,6 +26,7 @@ import './Composer.css'
 interface ComposerProps {
   roomId: string
   roomName: string
+  isDm?: boolean
   members: RoomMember[]
   // #47: rooms this user belongs to, for the #roomname autocomplete --
   // deliberately the same list ChatPane already resolves message-display
@@ -29,6 +34,12 @@ interface ComposerProps {
   // while typing and what actually renders as a link later agree.
   rooms: MyRoomItem[]
   disabled?: boolean
+  // #57: an archived room is permanently read-only, not just transiently
+  // disconnected -- kept as its own prop rather than folded into `disabled`
+  // so the placeholder/status text can say why, instead of the connecting/
+  // offline copy below (which would be actively misleading here: waiting
+  // won't ever re-enable this).
+  archived?: boolean
   onSend: (content: string, imageId?: string, fileId?: string) => void
 }
 
@@ -62,6 +73,19 @@ function detectRoomReferenceQuery(text: string, cursor: number): TriggerQuery |
   return detectTriggerQuery(text, cursor, '#')
 }
 
+// #54: a dedicated scan rather than detectTriggerQuery(text, cursor, ':')
+// -- shortcode names (see emojiShortcodes.ts) can contain '+'/'-' (':+1:',
+// ':t-rex:') but never '.', the reverse of what the shared @/# charset
+// allows, so it doesn't fit that helper's single fixed charset.
+function detectEmojiQuery(text: string, cursor: number): TriggerQuery | null {
+  let i = cursor - 1
+  while (i >= 0 && /[a-zA-Z0-9_+-]/.test(text[i])) i--
+  if (i < 0 || text[i] !== ':') return null
+  const prevChar = text[i - 1]
+  if (prevChar && /\w/.test(prevChar)) return null
+  return { start: i, end: cursor, text: text.slice(i + 1, cursor) }
+}
+
 interface AttachMenuProps {
   onPickPhoto: () => void
   onPickFile: () => void
@@ -89,7 +113,12 @@ function AttachMenu({ onPickPhoto, onPickFile, onClose }: AttachMenuProps) {
   )
 }
 
-export function Composer({ roomId, roomName, members, rooms, disabled, onSend }: ComposerProps) {
+export function Composer({ roomId, roomName, isDm, members, rooms, disabled, archived, onSend }: ComposerProps) {
+  // Every gate below (attach/emoji buttons, textarea, send button) reads
+  // this instead of the raw `disabled` prop -- an archived room must be
+  // just as unwritable as a disconnected one, it just says why differently
+  // (see the placeholder/status text further down).
+  const isDisabled = disabled || archived
   const [value, setValue] = useState('')
   const [pendingImage, setPendingImage] = useState<{ id: string; previewUrl: string } | null>(null)
   const [pendingFile, setPendingFile] = useState<{ id: string; filename: string; size: number } | null>(
@@ -103,8 +132,11 @@ export function Composer({ roomId, roomName, members, rooms, disabled, onSend }:
   const [mentionActiveIndex, setMentionActiveIndex] = useState(0)
   const [roomQuery, setRoomQuery] = useState<TriggerQuery | null>(null)
   const [roomActiveIndex, setRoomActiveIndex] = useState(0)
+  const [emojiQuery, setEmojiQuery] = useState<TriggerQuery | null>(null)
+  const [emojiActiveIndex, setEmojiActiveIndex] = useState(0)
   const [dragActive, setDragActive] = useState(false)
   const [attachMenuOpen, setAttachMenuOpen] = useState(false)
+  const { byShortcode: customEmojiByShortcode } = useCustomEmoji()
   const textareaRef = useRef<HTMLTextAreaElement>(null)
   const fileInputRef = useRef<HTMLInputElement>(null)
   // #29: a separate input with an image/video accept hint, so mobile
@@ -135,6 +167,39 @@ export function Composer({ roomId, roomName, members, rooms, disabled, onSend }:
     return rooms.filter((r) => r.name.toLowerCase().startsWith(q)).slice(0, 8)
   }, [roomQuery, rooms])
 
+  const emojiMatches = useMemo((): EmojiShortcodeMatch[] => {
+    if (!emojiQuery) return []
+    const q = emojiQuery.text.toLowerCase()
+    // A bare ":" with nothing typed yet -- suggest recently-used emoji
+    // (already capped to 8, see recentEmoji.ts) rather than an arbitrary
+    // slice of the ~950 known shortcodes. A recent custom-emoji pick is
+    // stored as its literal `:shortcode:` (see recordEmojiUsed's call
+    // sites) -- resolved against the live registry the same way, so a
+    // since-deleted one just doesn't show up here.
+    if (!q) {
+      return getRecentEmoji()
+        .map((value) => {
+          const customMatch = /^:([a-z0-9_-]+):$/.exec(value)
+          if (customMatch && customEmojiByShortcode.has(customMatch[1])) {
+            return { shortcode: customMatch[1], glyph: null }
+          }
+          const shortcode = SHORTCODE_BY_GLYPH[value]
+          return shortcode ? { shortcode, glyph: value } : null
+        })
+        .filter((match): match is EmojiShortcodeMatch => match !== null)
+    }
+    // Custom emoji surface first -- a smaller, more specific set, and the
+    // whole reason this app has an upload feature at all is for them to be
+    // reachable as easily as the built-in set.
+    const customMatches: EmojiShortcodeMatch[] = [...customEmojiByShortcode.keys()]
+      .filter((shortcode) => shortcode.startsWith(q))
+      .map((shortcode) => ({ shortcode, glyph: null }))
+    const builtinMatches: EmojiShortcodeMatch[] = Object.keys(EMOJI_SHORTCODES)
+      .filter((shortcode) => shortcode.startsWith(q))
+      .map((shortcode) => ({ shortcode, glyph: EMOJI_SHORTCODES[shortcode] }))
+    return [...customMatches, ...builtinMatches].slice(0, 8)
+  }, [emojiQuery, customEmojiByShortcode])
+
   useEffect(() => {
     getUploadLimit()
       .then((limit) => setMaxUploadBytes(limit.max_upload_bytes))
@@ -158,6 +223,7 @@ export function Composer({ roomId, roomName, members, rooms, disabled, onSend }:
     setValue('')
     setMentionQuery(null)
     setRoomQuery(null)
+    setEmojiQuery(null)
     removePendingImage()
     setPendingFile(null)
     requestAnimationFrame(autoGrow)
@@ -195,6 +261,34 @@ export function Composer({ roomId, roomName, members, rooms, disabled, onSend }:
     })
   }
 
+  function selectEmojiShortcode(shortcode: string) {
+    const query = emojiQuery
+    if (!query) return
+    // A custom emoji has no unicode glyph to substitute -- its literal
+    // `:shortcode:` text is what actually gets stored/rendered (see
+    // MessageContent.tsx's convertCustomEmojiShortcodes), so that's what
+    // goes in the textarea instead of a glyph.
+    const isCustom = customEmojiByShortcode.has(shortcode)
+    const glyph = EMOJI_SHORTCODES[shortcode]
+    if (!isCustom && !glyph) return
+    const inserted = isCustom ? `:${shortcode}:` : glyph
+    // Matches EmojiPicker's own insertEmoji -- a shortcode-completed emoji
+    // counts as "used" the same as one picked from the picker, so it
+    // shows up there too next time.
+    recordEmojiUsed(inserted)
+    const el = textareaRef.current
+    const next = value.slice(0, query.start) + inserted + ' ' + value.slice(query.end)
+    setValue(next)
+    setEmojiQuery(null)
+    requestAnimationFrame(() => {
+      if (!el) return
+      el.focus()
+      const cursor = query.start + inserted.length + 1 // inserted text + trailing space
+      el.setSelectionRange(cursor, cursor)
+      autoGrow()
+    })
+  }
+
   function handleKeyDown(e: KeyboardEvent<HTMLTextAreaElement>) {
     if (mentionQuery && mentionMatches.length > 0) {
       if (e.key === 'ArrowDown') {
@@ -240,6 +334,28 @@ export function Composer({ roomId, roomName, members, rooms, disabled, onSend }:
         return
       }
     }
+    if (emojiQuery && emojiMatches.length > 0) {
+      if (e.key === 'ArrowDown') {
+        e.preventDefault()
+        setEmojiActiveIndex((i) => (i + 1) % emojiMatches.length)
+        return
+      }
+      if (e.key === 'ArrowUp') {
+        e.preventDefault()
+        setEmojiActiveIndex((i) => (i - 1 + emojiMatches.length) % emojiMatches.length)
+        return
+      }
+      if (e.key === 'Enter' || e.key === 'Tab') {
+        e.preventDefault()
+        selectEmojiShortcode(emojiMatches[emojiActiveIndex].shortcode)
+        return
+      }
+      if (e.key === 'Escape') {
+        e.preventDefault()
+        setEmojiQuery(null)
+        return
+      }
+    }
     if (e.key === 'Enter' && !e.shiftKey) {
       e.preventDefault()
       handleSend()
@@ -257,6 +373,8 @@ export function Composer({ roomId, roomName, members, rooms, disabled, onSend }:
     setMentionActiveIndex(0)
     setRoomQuery(detectRoomReferenceQuery(el.value, cursor))
     setRoomActiveIndex(0)
+    setEmojiQuery(detectEmojiQuery(el.value, cursor))
+    setEmojiActiveIndex(0)
   }
 
   async function handleFile(file: File) {
@@ -294,7 +412,7 @@ export function Composer({ roomId, roomName, members, rooms, disabled, onSend }:
 
   function handleDragEnter(e: DragEvent<HTMLDivElement>) {
     e.preventDefault()
-    if (disabled) return
+    if (isDisabled) return
     dragCounterRef.current++
     setDragActive(true)
   }
@@ -316,7 +434,7 @@ export function Composer({ roomId, roomName, members, rooms, disabled, onSend }:
     e.preventDefault()
     dragCounterRef.current = 0
     setDragActive(false)
-    if (disabled) return
+    if (isDisabled) return
     // Only the first dropped file, matching the existing single-attachment-
     // per-message limit (the button-triggered file input isn't `multiple`
     // either).
@@ -418,7 +536,7 @@ export function Composer({ roomId, roomName, members, rooms, disabled, onSend }:
             type="button"
             className="composer-attach"
             onClick={() => setAttachMenuOpen((v) => !v)}
-            disabled={disabled || uploading}
+            disabled={isDisabled || uploading}
             aria-label="Attach a photo or file"
             aria-expanded={attachMenuOpen}
           >
@@ -457,7 +575,7 @@ export function Composer({ roomId, roomName, members, rooms, disabled, onSend }:
             type="button"
             className="composer-emoji-trigger"
             onClick={() => setEmojiPickerOpen((v) => !v)}
-            disabled={disabled}
+            disabled={isDisabled}
             aria-label="Insert an emoji"
           >
             🙂
@@ -476,7 +594,7 @@ export function Composer({ roomId, roomName, members, rooms, disabled, onSend }:
             ref={textareaRef}
             rows={1}
             value={value}
-            disabled={disabled}
+            disabled={isDisabled}
             onChange={(e) => {
               setValue(e.target.value)
               autoGrow()
@@ -485,10 +603,20 @@ export function Composer({ roomId, roomName, members, rooms, disabled, onSend }:
               setMentionActiveIndex(0)
               setRoomQuery(detectRoomReferenceQuery(e.target.value, cursor))
               setRoomActiveIndex(0)
+              setEmojiQuery(detectEmojiQuery(e.target.value, cursor))
+              setEmojiActiveIndex(0)
             }}
             onSelect={handleSelectionChange}
             onKeyDown={handleKeyDown}
-            placeholder={disabled ? (online ? 'Connecting…' : "You're offline") : `Message #${roomName}`}
+            placeholder={
+              archived
+                ? 'This room has been archived'
+                : disabled
+                  ? online
+                    ? 'Connecting…'
+                    : "You're offline"
+                  : `Message ${isDm ? roomName : `#${roomName}`}`
+            }
             spellCheck
           />
           {mentionQuery && mentionMatches.length > 0 && (
@@ -507,12 +635,20 @@ export function Composer({ roomId, roomName, members, rooms, disabled, onSend }:
               onHover={setRoomActiveIndex}
             />
           )}
+          {emojiQuery && emojiMatches.length > 0 && (
+            <EmojiShortcodeAutocomplete
+              matches={emojiMatches}
+              activeIndex={emojiActiveIndex}
+              onPick={selectEmojiShortcode}
+              onHover={setEmojiActiveIndex}
+            />
+          )}
         </div>
         <button
           type="button"
           className="composer-send"
           onClick={handleSend}
-          disabled={disabled || (!value.trim() && !pendingImage && !pendingFile)}
+          disabled={isDisabled || (!value.trim() && !pendingImage && !pendingFile)}
           aria-label="Send message"
         >
           <svg width="15" height="15" viewBox="0 0 20 20" aria-hidden="true">
@@ -520,8 +656,12 @@ export function Composer({ roomId, roomName, members, rooms, disabled, onSend }:
           </svg>
         </button>
       </div>
-      {disabled && (
+      {archived ? (
+        <div className="composer-status">This room has been archived and is read-only</div>
+      ) : (
+        disabled && (
           <div className="composer-status">{online ? 'Connecting…' : "You're offline — messages can't be sent right now"}</div>
+        )
       )}
     </div>
   )

frontend/src/components/ComposerAutocomplete.css

@@ -40,6 +40,18 @@
   color: var(--ds-accent);
 }
 
+.composer-autocomplete-emoji-glyph {
+  font-size: 1rem;
+  line-height: 1;
+}
+
+.composer-autocomplete-custom-emoji {
+  display: block;
+  width: 1rem;
+  height: 1rem;
+  object-fit: contain;
+}
+
 .composer-autocomplete-secondary {
   font-size: 0.76rem;
   color: var(--ds-muted);

frontend/src/components/CustomEmojiManageModal.tsx

@@ -0,0 +1,99 @@
+import { useState } from 'react'
+import { deleteCustomEmoji } from '../api/customEmoji'
+import { useAuth } from '../context/AuthContext'
+import { useCustomEmoji } from '../context/CustomEmojiContext'
+import type { CustomEmoji } from '../types'
+import { CustomEmojiUploadModal } from './CustomEmojiUploadModal'
+import { EmojiGlyph } from './MessageContent'
+import './Modal.css'
+
+interface CustomEmojiManageModalProps {
+  onClose: () => void
+}
+
+// Moved out of the reaction/composer emoji picker -- that grid packs items
+// 9-to-a-row with a delete "x" overlapping the glyph itself, which on a
+// touch screen is far too easy to hit by accident while just trying to
+// react. A dedicated list with a normal-sized "Delete" button (plus the
+// same confirm() every other destructive action in this app uses) needs a
+// deliberate tap to actually delete something.
+export function CustomEmojiManageModal({ onClose }: CustomEmojiManageModalProps) {
+  const { user } = useAuth()
+  const { list, refresh } = useCustomEmoji()
+  const [uploadOpen, setUploadOpen] = useState(false)
+  const [deletingId, setDeletingId] = useState<string | null>(null)
+
+  async function handleDelete(emoji: CustomEmoji) {
+    if (!confirm(`Delete :${emoji.shortcode}:? This can't be undone.`)) return
+    setDeletingId(emoji.id)
+    try {
+      await deleteCustomEmoji(emoji.id)
+      await refresh()
+    } finally {
+      setDeletingId(null)
+    }
+  }
+
+  return (
+    <div className="modal-scrim" onClick={onClose}>
+      <div className="modal" onClick={(e) => e.stopPropagation()}>
+        <div className="modal-header">
+          <h2>Custom emoji</h2>
+          <button type="button" className="modal-close" onClick={onClose} aria-label="Close">
+            &times;
+          </button>
+        </div>
+
+        <div className="modal-field-label">Site emoji</div>
+        {list.length === 0 ? (
+          <p className="modal-empty">No custom emoji yet.</p>
+        ) : (
+          list.map((emoji) => {
+            const canDelete = user?.id === emoji.uploaded_by || user?.is_site_admin
+            return (
+              <div key={emoji.id} className="modal-list-row">
+                <div className="modal-list-row-body">
+                  <div className="modal-list-row-title">
+                    <EmojiGlyph value={`:${emoji.shortcode}:`} /> :{emoji.shortcode}:
+                  </div>
+                  <div className="modal-list-row-sub">
+                    Added {new Date(emoji.created_at).toLocaleDateString()}
+                  </div>
+                </div>
+                {canDelete && (
+                  <button
+                    type="button"
+                    className="modal-list-row-action"
+                    disabled={deletingId === emoji.id}
+                    onClick={() => handleDelete(emoji)}
+                  >
+                    {deletingId === emoji.id ? 'Deleting…' : 'Delete'}
+                  </button>
+                )}
+              </div>
+            )
+          })
+        )}
+
+        <div className="modal-actions">
+          <button type="button" className="btn-secondary" onClick={onClose}>
+            Close
+          </button>
+          <button type="button" className="btn-primary" onClick={() => setUploadOpen(true)}>
+            Add emoji
+          </button>
+        </div>
+      </div>
+
+      {uploadOpen && (
+        <CustomEmojiUploadModal
+          onClose={() => setUploadOpen(false)}
+          onUploaded={() => {
+            refresh()
+            setUploadOpen(false)
+          }}
+        />
+      )}
+    </div>
+  )
+}

frontend/src/components/CustomEmojiUploadModal.tsx

@@ -0,0 +1,108 @@
+import { useState, type ChangeEvent, type FormEvent } from 'react'
+import { uploadCustomEmoji } from '../api/customEmoji'
+import { ApiError } from '../api/client'
+import { EMOJI_SHORTCODES } from '../lib/emojiShortcodes'
+import './Modal.css'
+
+interface CustomEmojiUploadModalProps {
+  onClose: () => void
+  onUploaded: () => void
+}
+
+// Mirrors the shortcode charset the backend actually enforces (see
+// backend/app/services/custom_emoji_service.py's SHORTCODE_PATTERN) --
+// checked here too so a bad name shows up immediately next to the field
+// instead of only after a round trip.
+const SHORTCODE_PATTERN = /^[a-z0-9_-]{2,30}$/
+
+export function CustomEmojiUploadModal({ onClose, onUploaded }: CustomEmojiUploadModalProps) {
+  const [shortcode, setShortcode] = useState('')
+  const [file, setFile] = useState<File | null>(null)
+  const [previewUrl, setPreviewUrl] = useState<string | null>(null)
+  const [error, setError] = useState<string | null>(null)
+  const [submitting, setSubmitting] = useState(false)
+
+  function handleFileSelected(e: ChangeEvent<HTMLInputElement>) {
+    const selected = e.target.files?.[0] ?? null
+    if (previewUrl) URL.revokeObjectURL(previewUrl)
+    setFile(selected)
+    setPreviewUrl(selected ? URL.createObjectURL(selected) : null)
+  }
+
+  function handleClose() {
+    if (previewUrl) URL.revokeObjectURL(previewUrl)
+    onClose()
+  }
+
+  const normalizedShortcode = shortcode.trim().toLowerCase()
+  const shortcodeValid = SHORTCODE_PATTERN.test(normalizedShortcode)
+  // A built-in shortcode always wins when :name: is typed in a message
+  // (see MessageContent.tsx's convertShortcodes, which runs first) -- a
+  // custom emoji uploaded under a colliding name would still upload fine,
+  // but could never actually be *reached* by typing its shortcode. Not a
+  // hard block (site-admin-free upload means no server-side authority to
+  // enforce this against ~950 names), just steered away from here.
+  const collidesWithBuiltin = shortcodeValid && normalizedShortcode in EMOJI_SHORTCODES
+
+  async function handleSubmit(e: FormEvent) {
+    e.preventDefault()
+    if (!file || !shortcodeValid) return
+    setSubmitting(true)
+    setError(null)
+    try {
+      await uploadCustomEmoji(normalizedShortcode, file)
+      onUploaded()
+    } catch (err) {
+      setError(err instanceof ApiError ? err.message : String(err))
+      setSubmitting(false)
+    }
+  }
+
+  return (
+    <div className="modal-scrim" onClick={handleClose}>
+      <div className="modal" onClick={(e) => e.stopPropagation()}>
+        <div className="modal-header">
+          <h2>Add custom emoji</h2>
+          <button type="button" className="modal-close" onClick={handleClose} aria-label="Close">
+            &times;
+          </button>
+        </div>
+        <form onSubmit={handleSubmit}>
+          <div className="modal-field-label">Shortcode</div>
+          <input
+            type="text"
+            value={shortcode}
+            onChange={(e) => setShortcode(e.target.value)}
+            placeholder="party-parrot"
+            autoFocus
+          />
+          {shortcode && !shortcodeValid && (
+            <p className="modal-error">
+              2-30 characters: lowercase letters, numbers, hyphens, underscores
+            </p>
+          )}
+          {collidesWithBuiltin && (
+            <p className="modal-error">
+              :{normalizedShortcode}: is already a built-in emoji -- typing it will always show that
+              one instead of yours
+            </p>
+          )}
+          <div className="modal-field-label">Image</div>
+          <input type="file" accept="image/png,image/jpeg,image/gif,image/webp" onChange={handleFileSelected} />
+          {previewUrl && (
+            <img src={previewUrl} alt="Preview" className="custom-emoji-upload-preview" />
+          )}
+          {error && <p className="modal-error">{error}</p>}
+          <div className="modal-actions">
+            <button type="button" className="btn-secondary" onClick={handleClose}>
+              Cancel
+            </button>
+            <button type="submit" className="btn-primary" disabled={submitting || !file || !shortcodeValid}>
+              {submitting ? 'Uploading…' : 'Add emoji'}
+            </button>
+          </div>
+        </form>
+      </div>
+    </div>
+  )
+}

frontend/src/components/EmojiPicker.tsx

@@ -1,8 +1,10 @@
 import { useMemo, useState } from 'react'
+import { useCustomEmoji } from '../context/CustomEmojiContext'
 import { useEscapeKey } from '../hooks/useEscapeKey'
 import { ALL_EMOJI, EMOJI_CATEGORIES } from '../lib/emoji'
 import { EMOJI_NAMES } from '../lib/emojiNames'
 import { getRecentEmoji, recordEmojiUsed } from '../lib/recentEmoji'
+import { EmojiGlyph } from './MessageContent'
 import './EmojiPicker.css'
 
 interface EmojiPickerProps {
@@ -17,7 +19,17 @@ interface EmojiPickerProps {
 // available viewport space) need this to know how much room to check for.
 export const EMOJI_PICKER_MAX_HEIGHT = 380
 
-function searchEmoji(query: string): string[] {
+// Every emoji this picker deals with -- built-in or custom -- is just a
+// string from here on: a raw unicode glyph, or a custom emoji's literal
+// `:shortcode:` reference (see EmojiGlyph in MessageContent.tsx, which
+// resolves either into the right thing to render). Keeping both kinds in
+// the same list/search/recent machinery means there's exactly one grid
+// rendering path instead of a parallel one for custom emoji.
+function titleFor(value: string): string {
+  return EMOJI_NAMES[value]?.name ?? value
+}
+
+function searchEmoji(query: string, customShortcodes: string[]): string[] {
   const q = query.trim().toLowerCase()
   if (!q) return []
   const seen = new Set<string>()
@@ -32,13 +44,18 @@ function searchEmoji(query: string): string[] {
       results.push(emoji)
     }
   }
+  for (const shortcode of customShortcodes) {
+    if (shortcode.toLowerCase().includes(q)) results.push(`:${shortcode}:`)
+  }
   return results
 }
 
 export function EmojiPicker({ onPick, onClose, placement = 'below', align = 'left' }: EmojiPickerProps) {
   useEscapeKey(onClose)
+  const { list: customEmoji } = useCustomEmoji()
   const [query, setQuery] = useState('')
-  const searchResults = useMemo(() => searchEmoji(query), [query])
+  const customShortcodes = useMemo(() => customEmoji.map((e) => e.shortcode), [customEmoji])
+  const searchResults = useMemo(() => searchEmoji(query, customShortcodes), [query, customShortcodes])
   const searching = query.trim().length > 0
   // A snapshot taken once when the picker opens, not live-updating as picks
   // happen within this same session -- picking an emoji always closes the
@@ -75,10 +92,10 @@ export function EmojiPicker({ onPick, onClose, placement = 'below', align = 'lef
                   type="button"
                   role="menuitem"
                   className="emoji-picker-item"
-                  title={EMOJI_NAMES[emoji]?.name}
+                  title={titleFor(emoji)}
                   onClick={() => pick(emoji)}
                 >
-                  {emoji}
+                  <EmojiGlyph value={emoji} />
                 </button>
               ))}
             </div>
@@ -87,6 +104,25 @@ export function EmojiPicker({ onPick, onClose, placement = 'below', align = 'lef
           )
         ) : (
           <>
+            {customEmoji.length > 0 && (
+              <div className="emoji-picker-category">
+                <div className="emoji-picker-category-label">Custom</div>
+                <div className="emoji-picker-grid">
+                  {customEmoji.map((e) => (
+                    <button
+                      key={e.id}
+                      type="button"
+                      role="menuitem"
+                      className="emoji-picker-item"
+                      title={`:${e.shortcode}:`}
+                      onClick={() => pick(`:${e.shortcode}:`)}
+                    >
+                      <EmojiGlyph value={`:${e.shortcode}:`} />
+                    </button>
+                  ))}
+                </div>
+              </div>
+            )}
             {recent.length > 0 && (
               <div className="emoji-picker-category">
                 <div className="emoji-picker-category-label">Recently used</div>
@@ -97,10 +133,10 @@ export function EmojiPicker({ onPick, onClose, placement = 'below', align = 'lef
                       type="button"
                       role="menuitem"
                       className="emoji-picker-item"
-                      title={EMOJI_NAMES[emoji]?.name}
+                      title={titleFor(emoji)}
                       onClick={() => pick(emoji)}
                     >
-                      {emoji}
+                      <EmojiGlyph value={emoji} />
                     </button>
                   ))}
                 </div>
@@ -116,10 +152,10 @@ export function EmojiPicker({ onPick, onClose, placement = 'below', align = 'lef
                       type="button"
                       role="menuitem"
                       className="emoji-picker-item"
-                      title={EMOJI_NAMES[emoji]?.name}
+                      title={titleFor(emoji)}
                       onClick={() => pick(emoji)}
                     >
-                      {emoji}
+                      <EmojiGlyph value={emoji} />
                     </button>
                   ))}
                 </div>

frontend/src/components/EmojiShortcodeAutocomplete.tsx

@@ -0,0 +1,54 @@
+import { getCustomEmojiUrl } from '../api/customEmoji'
+import './ComposerAutocomplete.css'
+
+export interface EmojiShortcodeMatch {
+  shortcode: string
+  // null for a custom emoji -- there's no unicode glyph to show, so the
+  // row renders its uploaded image instead (see getCustomEmojiUrl below).
+  glyph: string | null
+}
+
+interface EmojiShortcodeAutocompleteProps {
+  matches: EmojiShortcodeMatch[]
+  activeIndex: number
+  onPick: (shortcode: string) => void
+  onHover: (index: number) => void
+}
+
+export function EmojiShortcodeAutocomplete({
+  matches,
+  activeIndex,
+  onPick,
+  onHover,
+}: EmojiShortcodeAutocompleteProps) {
+  return (
+    <div className="composer-autocomplete" role="listbox">
+      {matches.map((match, i) => (
+        <button
+          key={match.shortcode}
+          type="button"
+          role="option"
+          aria-selected={i === activeIndex}
+          className={`composer-autocomplete-item${i === activeIndex ? ' composer-autocomplete-item-active' : ''}`}
+          // Selecting must survive the textarea's blur (which would
+          // otherwise fire first and could dismiss the dropdown) --
+          // onMouseDown fires before blur, onClick fires after.
+          onMouseDown={(e) => e.preventDefault()}
+          onClick={() => onPick(match.shortcode)}
+          onMouseEnter={() => onHover(i)}
+        >
+          <span className="composer-autocomplete-emoji-glyph">
+            {match.glyph ?? (
+              <img
+                src={getCustomEmojiUrl(match.shortcode)}
+                alt=""
+                className="composer-autocomplete-custom-emoji"
+              />
+            )}
+          </span>
+          <span className="composer-autocomplete-primary">:{match.shortcode}:</span>
+        </button>
+      ))}
+    </div>
+  )
+}

frontend/src/components/FilePreviewModal.tsx

@@ -1,9 +1,9 @@
-import { useEffect, useState } from 'react'
+import { useEffect, useMemo, useState } from 'react'
 import Markdown from 'markdown-to-jsx'
 import { getRoomFileUrl } from '../api/rooms'
 import { useEscapeKey } from '../hooks/useEscapeKey'
 import type { MessageFileInfo } from '../types'
-import { MARKDOWN_OPTIONS } from './MessageContent'
+import { createMarkdownOptions, preprocessMarkdown } from './MessageContent'
 import './FilePreviewModal.css'
 
 export type PreviewKind = 'markdown' | 'text' | 'pdf'
@@ -33,6 +33,12 @@ export function FilePreviewModal({ roomId, file, kind, onClose }: FilePreviewMod
   const [pdfUrl, setPdfUrl] = useState<string | null>(null)
   const [error, setError] = useState<string | null>(null)
   const fileUrl = getRoomFileUrl(roomId, file.id)
+  // #21: subscript/superscript and heading-id support -- see MessageContent
+  // for why this needs to run before the Markdown component sees the text.
+  const markdownPreview = useMemo(
+    () => (content !== null ? preprocessMarkdown(content) : null),
+    [content],
+  )
 
   useEffect(() => {
     let cancelled = false
@@ -102,9 +108,11 @@ export function FilePreviewModal({ roomId, file, kind, onClose }: FilePreviewMod
         <div className={`file-preview-body${kind === 'pdf' ? ' file-preview-body-pdf' : ''}`}>
           {error && <p className="file-preview-error">{error}</p>}
           {!error && kind !== 'pdf' && content === null && <p className="file-preview-loading">Loading…</p>}
-          {!error && content !== null && kind === 'markdown' && (
+          {!error && kind === 'markdown' && markdownPreview && (
             <div className="message-text file-preview-markdown">
-              <Markdown options={MARKDOWN_OPTIONS}>{content}</Markdown>
+              <Markdown options={createMarkdownOptions(markdownPreview.headingIds)}>
+                {markdownPreview.text}
+              </Markdown>
             </div>
           )}
           {!error && content !== null && kind === 'text' && <pre className="file-preview-text">{content}</pre>}

frontend/src/components/MessageContent.css

@@ -0,0 +1,28 @@
+/* #18: em-relative, deliberately -- renders correctly inline in message
+   text, inside a reaction pill, and inside the emoji picker's grid without
+   a separate override per context, since each of those already sets its
+   own font-size and this just tracks it. Kept in this file (imported
+   directly by MessageContent.tsx) rather than MessageList.css so it's
+   loaded wherever MessageContent renders -- FilePreviewModal and HelpPage
+   included, not just the message list.
+
+   #71: also multiplied by --emoji-scale, the manual "make emoji bigger"
+   preference -- but that variable is only ever set on MessageContent's own
+   wrapper div (inline style, scoped to that element and its descendants),
+   never at :root, so var(..., 1) correctly falls back to a no-op multiplier
+   everywhere else this class is reused (the picker's grid, reaction pills)
+   instead of also inflating those and breaking their fixed-size layout. */
+.message-custom-emoji {
+  height: calc(1.2em * var(--emoji-scale, 1));
+  width: calc(1.2em * var(--emoji-scale, 1));
+  object-fit: contain;
+  vertical-align: -0.25em;
+}
+
+/* #71: a raw unicode emoji wrapped by wrapEmojiGlyphs -- same --emoji-scale
+   multiplier as the custom-emoji image above, so "make emoji bigger"
+   applies uniformly regardless of which kind of emoji it is. */
+.inline-emoji {
+  display: inline-block;
+  font-size: calc(1em * var(--emoji-scale, 1));
+}

frontend/src/components/MessageContent.tsx

@@ -1,7 +1,11 @@
 import Markdown from 'markdown-to-jsx'
-import type { ReactNode } from 'react'
+import type { CSSProperties, ReactNode } from 'react'
 import { Link } from 'react-router-dom'
+import { getCustomEmojiUrl } from '../api/customEmoji'
+import { useAuth } from '../context/AuthContext'
+import { useCustomEmoji } from '../context/CustomEmojiContext'
 import { EMOJI_SHORTCODES } from '../lib/emojiShortcodes'
+import './MessageContent.css'
 
 interface MessageContentProps {
   content: string
@@ -49,8 +53,11 @@ interface MarkdownLinkProps {
 // span instead of an actual anchor. highlightRoomReferences does the same
 // trick for #roomname, but a room reference *is* meant to be navigable, so
 // it becomes a real (client-side-routed) Link instead of an inert span.
-// Everything else renders as a real external link, same as before mentions
+// convertSubSuperscript (#21) reuses the identical trick for `~sub~`/`^sup^`
-// existed.
+// -- markdown-to-jsx has no plugin hook for new inline syntax, but a link is
+// something it already parses correctly, so `sub:`/`sup:` "URLs" are just
+// another carrier for meaning the parser was never told about. Everything
+// else renders as a real external link, same as before mentions existed.
 function MarkdownLink({ href, children }: MarkdownLinkProps) {
   if (href?.startsWith('mention:')) {
     return <span className="message-mention">{children}</span>
@@ -62,6 +69,31 @@ function MarkdownLink({ href, children }: MarkdownLinkProps) {
       </Link>
     )
   }
+  if (href === 'sub:') {
+    return <sub>{children}</sub>
+  }
+  if (href === 'sup:') {
+    return <sup>{children}</sup>
+  }
+  if (href?.startsWith('emoji:')) {
+    const shortcode = href.slice('emoji:'.length)
+    return (
+      <img
+        src={getCustomEmojiUrl(shortcode)}
+        alt={`:${shortcode}:`}
+        title={`:${shortcode}:`}
+        className="message-custom-emoji"
+      />
+    )
+  }
+  // #71: a raw unicode emoji has no element of its own to size independently
+  // of the surrounding text -- it's just characters in a string. Wrapping
+  // each one individually (see wrapEmojiGlyphs below) gives it one, purely
+  // so the emoji-size preference can scale it via CSS the same way it
+  // already scales a custom emoji's <img>.
+  if (href === 'glyph:') {
+    return <span className="inline-emoji">{children}</span>
+  }
   return (
     <a href={href} target="_blank" rel="noopener noreferrer">
       {children}
@@ -101,6 +133,137 @@ function convertShortcodes(text: string): string {
     .join('\n')
 }
 
+// #21: single tilde/caret delimiters, no spaces inside, and not doubled --
+// `~~text~~` is strikethrough (already natively supported) so a leading or
+// trailing extra `~` excludes the match, matching markdownguide.org's
+// extended syntax for both constructs. Converts a complete `~sub~`/`^sup^`
+// span to `[sub](sub:)`/`[sup](sup:)` -- see MarkdownLink's comment for why
+// a link is the carrier.
+const SUBSCRIPT_PATTERN = /(?<!~)~([^~\s]+)~(?!~)/g
+const SUPERSCRIPT_PATTERN = /\^([^^\s]+)\^/g
+
+function convertSubSuperscript(text: string): string {
+  const lines = text.split('\n')
+  let inFence = false
+  return lines
+    .map((line) => {
+      if (/^\s*```/.test(line)) {
+        inFence = !inFence
+        return line
+      }
+      if (inFence) return line
+      return line
+        .split(/(`+[^`]*`+)/g)
+        .map((part, i) =>
+          i % 2 === 0
+            ? part
+                .replace(SUBSCRIPT_PATTERN, (_match, inner: string) => `[${inner}](sub:)`)
+                .replace(SUPERSCRIPT_PATTERN, (_match, inner: string) => `[${inner}](sup:)`)
+            : part,
+        )
+        .join('')
+    })
+    .join('\n')
+}
+
+// #21: markdown-to-jsx has no option for an explicit heading anchor --
+// every heading already gets an auto-generated slug from its own text
+// (useful for linking within a message), and `{#custom-id}` is meant to
+// *override* that slug, not add a second id next to it. There's no plugin
+// hook for new block syntax either, so this strips the marker from the
+// heading's own text (same fence-skipping convention as the functions
+// above) and remembers the association by that now-bare text -- the one
+// hook markdown-to-jsx *does* expose, `slugify` (see createMarkdownOptions
+// below), gets called with exactly that text, letting the requested id
+// stand in for the auto-generated one.
+const HEADING_ID_PATTERN = /^(#{1,6}\s+.*?)\s*\{#([a-zA-Z0-9_-]+)\}\s*$/
+
+function extractHeadingIds(text: string): { text: string; headingIds: Map<string, string> } {
+  const headingIds = new Map<string, string>()
+  const lines = text.split('\n')
+  let inFence = false
+  const nextLines = lines.map((line) => {
+    if (/^\s*```/.test(line)) {
+      inFence = !inFence
+      return line
+    }
+    if (inFence) return line
+    const match = line.match(HEADING_ID_PATTERN)
+    if (!match) return line
+    const [, headingLine, customId] = match
+    headingIds.set(headingLine.replace(/^#{1,6}\s+/, ''), customId)
+    return headingLine
+  })
+  return { text: nextLines.join('\n'), headingIds }
+}
+
+// #18: a *complete* `:name:` that survived convertShortcodes above (it only
+// replaces names it recognizes, so an unmatched one -- built-in or not --
+// passes through untouched) and matches a shortcode this install actually
+// has a custom emoji for. Turns it into `[​:name:​](emoji:name)`, the same
+// link-trick MarkdownLink's other branches use -- deliberately reusing the
+// exact fence/code-span-skip convention every other converter in this file
+// follows, for the same reason (a pasted `:some_key:` in code shouldn't
+// light up as an emoji any more than an unrelated one should).
+const CUSTOM_EMOJI_PATTERN = /:([a-z0-9_-]+):/g
+
+function convertCustomEmojiShortcodes(text: string, shortcodes: Set<string>): string {
+  if (shortcodes.size === 0) return text
+  const lines = text.split('\n')
+  let inFence = false
+  return lines
+    .map((line) => {
+      if (/^\s*```/.test(line)) {
+        inFence = !inFence
+        return line
+      }
+      if (inFence) return line
+      return line
+        .split(/(`+[^`]*`+)/g)
+        .map((part, i) =>
+          i % 2 === 0
+            ? part.replace(CUSTOM_EMOJI_PATTERN, (match, name) =>
+                shortcodes.has(name) ? `[${match}](emoji:${name})` : match,
+              )
+            : part,
+        )
+        .join('')
+    })
+    .join('\n')
+}
+
+// Reaction pills and the "recently used" emoji row don't go through the
+// markdown pipeline at all -- they render a single stored value directly.
+// A custom emoji's value there is its literal `:shortcode:` (see
+// backend's MessageReaction.emoji); this is the equivalent one-value
+// resolution for those spots, so a deleted-since-reacted-with custom
+// emoji degrades to plain `:shortcode:` text instead of a broken image.
+interface EmojiGlyphProps {
+  value: string
+}
+
+export function EmojiGlyph({ value }: EmojiGlyphProps) {
+  const { byShortcode } = useCustomEmoji()
+  const match = /^:([a-z0-9_-]+):$/.exec(value)
+  const shortcode = match?.[1]
+  if (shortcode && byShortcode.has(shortcode)) {
+    return (
+      <img
+        src={getCustomEmojiUrl(shortcode)}
+        alt={value}
+        title={value}
+        className="message-custom-emoji"
+      />
+    )
+  }
+  // Wrapped the same way wrapEmojiGlyphs wraps a raw emoji in message text
+  // (see .inline-emoji), so a --emoji-scale set on an ancestor (the
+  // reaction pill's own span in MessageList.tsx) scales this the same way
+  // it scales the .message-custom-emoji img above -- and falls back to a
+  // no-op 1x everywhere else (the picker) with no --emoji-scale set at all.
+  return <span className="inline-emoji">{value}</span>
+}
+
 const MENTION_PATTERN = /@([a-zA-Z0-9_.-]+)/g
 
 // Turns a validated @username into `[@username](mention:username)` --
@@ -194,9 +357,13 @@ function preserveLineBreaks(text: string): string {
 }
 
 // Shared with FilePreviewModal so both render paths carry the exact same
-// XSS mitigation (disableParsingRawHTML) -- duplicating this object would
+// XSS mitigation (disableParsingRawHTML) and #21's heading-id/sub/superscript
-// risk the two drifting out of sync if one gets edited later.
+// support -- duplicating this would risk the two drifting out of sync if
-export const MARKDOWN_OPTIONS = {
+// one gets edited later. A function, not a plain constant, since `slugify`
+// needs each render's own headingIds map (see extractHeadingIds above) --
+// there's no per-render state to close over in a module-level object.
+export function createMarkdownOptions(headingIds: Map<string, string>) {
+  return {
     // The core XSS mitigation: raw HTML in message content is escaped
     // and printed literally instead of being parsed into elements.
     disableParsingRawHTML: true,
@@ -204,10 +371,79 @@ export const MARKDOWN_OPTIONS = {
       a: { component: MarkdownLink },
       img: { component: MarkdownImageLink },
     },
+    slugify: (input: string, defaultFn: (input: string) => string) =>
+      headingIds.get(input) ?? defaultFn(input),
+  }
+}
+
+// #21: preprocessing shared by MessageContent and FilePreviewModal --
+// subscript/superscript and heading-id overrides are general markdown
+// features, not chat-specific like mentions/shortcodes/room-references, so
+// a plain file preview gets them too.
+export function preprocessMarkdown(text: string): { text: string; headingIds: Map<string, string> } {
+  return extractHeadingIds(convertSubSuperscript(text))
+}
+
+// #71: gives every individual unicode emoji its own element (see
+// MarkdownLink's `glyph:` branch) purely so the emoji-size preference can
+// scale it independently of the surrounding text -- a raw emoji is just
+// characters in a string otherwise, with nothing CSS can address on its
+// own. Runs after convertShortcodes so a built-in `:name:` that just
+// became a glyph is wrapped too ("all emoji", not just ones typed as
+// literal unicode); same fence/code-span skip convention as every other
+// converter here.
+const EMOJI_GLYPH_PATTERN = /\p{Extended_Pictographic}(?:\p{Emoji_Modifier}|\u200D\p{Extended_Pictographic}|\uFE0F)*/gu
+
+function wrapEmojiGlyphs(text: string): string {
+  const lines = text.split('\n')
+  let inFence = false
+  return lines
+    .map((line) => {
+      if (/^\s*```/.test(line)) {
+        inFence = !inFence
+        return line
+      }
+      if (inFence) return line
+      return line
+        .split(/(`+[^`]*`+)/g)
+        .map((part, i) => (i % 2 === 0 ? part.replace(EMOJI_GLYPH_PATTERN, (match) => `[${match}](glyph:)`) : part))
+        .join('')
+    })
+    .join('\n')
+}
+
+// Exported so MessageList's reaction pills can apply the same viewer
+// preference to their own EmojiGlyph -- reactions render outside the
+// markdown pipeline entirely (see EmojiGlyph's own comment above), so they
+// need this looked up independently rather than inheriting --emoji-scale
+// from this component's wrapper div.
+export const EMOJI_SCALE_MULTIPLIER: Record<string, number> = {
+  small: 0.8,
+  normal: 1,
+  large: 1.5,
+  xlarge: 2,
 }
 
 export function MessageContent({ content, memberUsernames, myRooms }: MessageContentProps) {
+  const { user } = useAuth()
+  const { byShortcode } = useCustomEmoji()
+  const customShortcodes = new Set(byShortcode.keys())
   const withMentions = memberUsernames ? highlightMentions(content, memberUsernames) : content
   const withRoomRefs = myRooms ? highlightRoomReferences(withMentions, myRooms) : withMentions
-  return <Markdown options={MARKDOWN_OPTIONS}>{preserveLineBreaks(convertShortcodes(withRoomRefs))}</Markdown>
+  const withCustomEmoji = convertCustomEmojiShortcodes(convertShortcodes(withRoomRefs), customShortcodes)
+  const withEmojiGlyphs = wrapEmojiGlyphs(withCustomEmoji)
+  const { text, headingIds } = preprocessMarkdown(withEmojiGlyphs)
+  // #71: scoped to this element (not a :root-level variable) so it only
+  // ever affects emoji rendered in message text -- not the same
+  // .message-custom-emoji/EmojiGlyph markup reused by the emoji picker's
+  // grid, where a bigger image would just break its fixed-size layout
+  // instead of doing anything useful. Reaction pills DO scale too, but via
+  // their own inline --emoji-scale in MessageList.tsx, not by inheriting
+  // this one -- a pill isn't a descendant of this wrapper div.
+  const emojiScale = EMOJI_SCALE_MULTIPLIER[user?.emoji_scale ?? 'normal']
+  return (
+    <div style={{ '--emoji-scale': emojiScale } as CSSProperties}>
+      <Markdown options={createMarkdownOptions(headingIds)}>{preserveLineBreaks(text)}</Markdown>
+    </div>
+  )
 }

frontend/src/components/MessageList.css

@@ -53,8 +53,13 @@
 
 .message-image {
   display: block;
-  max-width: min(320px, 100%);
+  /* #71: rem, not px -- scales with the text-size setting (see
-  max-height: 240px;
+     lib/theme.ts's applyTextScale), same as every other size in this app.
+     min(...) still caps against the viewport in absolute px, since a
+     percentage-of-viewport constraint isn't something a root font-size
+     change should affect. */
+  max-width: min(20rem, 100%);
+  max-height: 15rem;
   object-fit: contain;
   border-radius: var(--radius);
   border: 1px solid var(--ds-border);
@@ -62,6 +67,44 @@
   margin-bottom: 4px;
 }
 
+.message-video-wrap {
+  position: relative;
+  display: inline-block;
+  max-width: min(20rem, 100%);
+  margin-bottom: 4px;
+}
+
+.message-video {
+  display: block;
+  width: 100%;
+  max-height: 15rem;
+  border-radius: var(--radius);
+  border: 1px solid var(--ds-border);
+  background: var(--ds-void);
+}
+
+.message-video-expand {
+  position: absolute;
+  top: 6px;
+  right: 6px;
+  display: flex;
+  align-items: center;
+  justify-content: center;
+  padding: 5px;
+  background: rgba(0, 0, 0, 0.6);
+  border: none;
+  border-radius: 6px;
+  color: white;
+  cursor: pointer;
+  opacity: 0;
+  transition: opacity 0.15s ease;
+}
+
+.message-video-wrap:hover .message-video-expand,
+.message-video-expand:focus-visible {
+  opacity: 1;
+}
+
 .message-file-attachment {
   display: inline-flex;
   align-items: center;
@@ -73,7 +116,7 @@
   margin-bottom: 4px;
   color: var(--ds-text);
   text-decoration: none;
-  max-width: min(320px, 100%);
+  max-width: min(20rem, 100%);
 }
 
 .message-file-attachment:hover {
@@ -304,6 +347,25 @@
   border-color: var(--ds-accent);
 }
 
+.message-delete-link {
+  background: var(--ds-surface-2);
+  border: 1px solid var(--ds-border);
+  color: var(--ds-muted);
+  font-size: 0.68rem;
+  cursor: pointer;
+  padding: 2px 8px;
+  border-radius: 6px;
+}
+
+.message-delete-link:hover {
+  color: var(--ds-danger);
+  border-color: var(--ds-danger);
+}
+
+.message-deleted-text {
+  color: var(--ds-muted);
+}
+
 .message-reaction-wrap {
   position: relative;
 }

frontend/src/components/MessageList.tsx

@@ -1,3 +1,4 @@
+import type { CSSProperties } from 'react'
 import { useEffect, useMemo, useRef, useState } from 'react'
 import { getRoomFileUrl, getRoomImageUrl } from '../api/rooms'
 import { useAuth } from '../context/AuthContext'
@@ -8,8 +9,9 @@ import { EMOJI_PICKER_MAX_HEIGHT, EmojiPicker } from './EmojiPicker'
 import { FilePreviewModal, getPreviewKind } from './FilePreviewModal'
 import { ImageLightbox } from './ImageLightbox'
 import { LinkPreviewCard } from './LinkPreviewCard'
-import { MessageContent } from './MessageContent'
+import { EMOJI_SCALE_MULTIPLIER, EmojiGlyph, MessageContent } from './MessageContent'
 import { UserAvatar } from './UserAvatar'
+import { VideoLightbox } from './VideoLightbox'
 import './MessageList.css'
 
 export function FileAttachmentIcon() {
@@ -60,6 +62,58 @@ function FileAttachmentCard({ file, roomId, onPreview }: FileAttachmentCardProps
   )
 }
 
+// #65: kept in sync with backend/app/storage.py's INLINE_SAFE_VIDEO_
+// CONTENT_TYPES -- the server only ever serves these particular content
+// types without a forced download, so a <video> tag pointed at anything
+// else would just show a broken player instead of playing (or, worse,
+// trigger a download the moment the browser tries to fetch it).
+const PLAYABLE_VIDEO_CONTENT_TYPES = new Set(['video/mp4', 'video/webm', 'video/ogg'])
+
+// #73: Slack's own threshold for the same "still grouped, but it's been a
+// while" call -- past this gap a same-sender message starts a new group
+// (its own avatar/name/timestamp) even with nobody else posting in
+// between, so a message sent minutes later doesn't hide under a stale
+// timestamp from the start of the run.
+const GROUP_BREAK_MS = 5 * 60 * 1000
+
+interface VideoAttachmentProps {
+  file: MessageFileInfo
+  roomId: string
+  onExpand: () => void
+}
+
+// Plays inline via the browser's own <video controls> (no custom overlay
+// needed for play/pause/volume/seek) -- the one thing it doesn't give a
+// small inline player is an obvious way to go bigger. The expand button
+// opens a VideoLightbox (matching how images already expand) rather than
+// calling the Fullscreen API directly on the video element -- that API is
+// unreliable in embedded/packaged contexts (e.g. the Electron desktop
+// build), where a rejected requestFullscreen() promise just does nothing
+// with no visible error.
+function VideoAttachment({ file, roomId, onExpand }: VideoAttachmentProps) {
+  return (
+    <div className="message-video-wrap">
+      <video src={getRoomFileUrl(roomId, file.id)} controls className="message-video" />
+      <button
+        type="button"
+        className="message-video-expand"
+        onClick={onExpand}
+        aria-label="Expand video"
+      >
+        <svg width="14" height="14" viewBox="0 0 20 20" fill="none" aria-hidden="true">
+          <path
+            d="M7 3H3v4M13 3h4v4M3 13v4h4M17 13v4h-4"
+            stroke="currentColor"
+            strokeWidth="1.6"
+            strokeLinecap="round"
+            strokeLinejoin="round"
+          />
+        </svg>
+      </button>
+    </div>
+  )
+}
+
 interface MessageListProps {
   roomId: string
   messages: (Message | ChatMessageEnvelope)[]
@@ -67,10 +121,23 @@ interface MessageListProps {
   myRooms: Map<string, string>
   onEdit: (messageId: string, content: string) => void
   onReact: (messageId: string, emoji: string) => void
+  onDelete: (messageId: string) => void
 }
 
-export function MessageList({ roomId, messages, members, myRooms, onEdit, onReact }: MessageListProps) {
+export function MessageList({
+  roomId,
+  messages,
+  members,
+  myRooms,
+  onEdit,
+  onReact,
+  onDelete,
+}: MessageListProps) {
   const { user } = useAuth()
+  // #71: same viewer preference MessageContent applies to in-text emoji,
+  // looked up separately here since a reaction pill isn't a descendant of
+  // that component's wrapper div (see EmojiGlyph's own comment).
+  const emojiScale = EMOJI_SCALE_MULTIPLIER[user?.emoji_scale ?? 'normal']
   const containerRef = useRef<HTMLDivElement>(null)
   const bottomRef = useRef<HTMLDivElement>(null)
   // Whether the view should be pinned to the latest message -- true right
@@ -81,6 +148,7 @@ export function MessageList({ roomId, messages, members, myRooms, onEdit, onReac
   const [editingId, setEditingId] = useState<string | null>(null)
   const [draft, setDraft] = useState('')
   const [lightboxSrc, setLightboxSrc] = useState<string | null>(null)
+  const [videoLightbox, setVideoLightbox] = useState<{ src: string; filename: string } | null>(null)
   const [reactingId, setReactingId] = useState<string | null>(null)
   const [reactionPlacement, setReactionPlacement] = useState<'above' | 'below'>('below')
   const [previewFile, setPreviewFile] = useState<MessageFileInfo | null>(null)
@@ -133,6 +201,14 @@ export function MessageList({ roomId, messages, members, myRooms, onEdit, onReac
     setEditingId(null)
   }
 
+  function handleDelete(messageId: string) {
+    // Matches the confirm() pattern already used for other destructive
+    // actions in this app (RoomInfoPanel's leave/delete-room,
+    // ProfileModal's delete-theme) rather than a custom dialog.
+    if (!confirm("Delete this message? This can't be undone.")) return
+    onDelete(messageId)
+  }
+
   return (
     <div className="message-list" ref={containerRef}>
       {messages.map((msg, i) => {
@@ -141,9 +217,15 @@ export function MessageList({ roomId, messages, members, myRooms, onEdit, onReac
         // Mattermost-style grouping: every message shows who sent it, but
         // consecutive messages from the same sender only repeat the
         // avatar/name/timestamp header on the first one in the run --
-        // applies uniformly, including to your own messages.
+        // applies uniformly, including to your own messages. Also breaks on
-        const isGroupStart = !prev || prev.user_id !== msg.user_id
+        // a long gap (see GROUP_BREAK_MS) so a message sent well after the
+        // rest of the run still gets its own visible timestamp.
+        const isGroupStart =
+          !prev ||
+          prev.user_id !== msg.user_id ||
+          new Date(msg.created_at).getTime() - new Date(prev.created_at).getTime() > GROUP_BREAK_MS
         const editing = editingId === msg.id
+        const deleted = !!msg.deleted_at
 
         return (
           <div key={msg.id} className={`message-row${isGroupStart ? ' message-row-start' : ''}`}>
@@ -166,7 +248,11 @@ export function MessageList({ roomId, messages, members, myRooms, onEdit, onReac
                   </span>
                 </div>
               )}
-              {editing ? (
+              {deleted ? (
+                <div className="message-text message-deleted-text">
+                  <em>This message was deleted</em>
+                </div>
+              ) : editing ? (
                 <textarea
                   autoFocus
                   rows={Math.min(10, draft.split('\n').length)}
@@ -193,7 +279,19 @@ export function MessageList({ roomId, messages, members, myRooms, onEdit, onReac
                       onClick={() => setLightboxSrc(getRoomImageUrl(roomId, msg.image_id!))}
                     />
                   )}
-                  {msg.file && (
+                  {msg.file && PLAYABLE_VIDEO_CONTENT_TYPES.has(msg.file.content_type) && (
+                    <VideoAttachment
+                      file={msg.file}
+                      roomId={roomId}
+                      onExpand={() =>
+                        setVideoLightbox({
+                          src: getRoomFileUrl(roomId, msg.file!.id),
+                          filename: msg.file!.filename,
+                        })
+                      }
+                    />
+                  )}
+                  {msg.file && !PLAYABLE_VIDEO_CONTENT_TYPES.has(msg.file.content_type) && (
                     <FileAttachmentCard
                       file={msg.file}
                       roomId={roomId}
@@ -221,7 +319,12 @@ export function MessageList({ roomId, messages, members, myRooms, onEdit, onReac
                             title={r.user_ids.map(displayNameForUserId).join(', ')}
                             onClick={() => onReact(msg.id, r.emoji)}
                           >
-                            <span>{r.emoji}</span>
+                            {/* No .inline-emoji here -- EmojiGlyph's own fallback branch
+                                already applies it, and stacking it here too would double
+                                the font-size multiplication for a custom-emoji img. */}
+                            <span style={{ '--emoji-scale': emojiScale } as CSSProperties}>
+                              <EmojiGlyph value={r.emoji} />
+                            </span>
                             <span>{r.count}</span>
                           </button>
                         )
@@ -231,7 +334,7 @@ export function MessageList({ roomId, messages, members, myRooms, onEdit, onReac
                 </>
               )}
             </div>
-            {!editing && (
+            {!editing && !deleted && (
               <div className="message-row-actions">
                 <div className="message-reaction-wrap">
                   <button
@@ -277,6 +380,16 @@ export function MessageList({ roomId, messages, members, myRooms, onEdit, onReac
                     Edit
                   </button>
                 )}
+                {mine && (
+                  <button
+                    type="button"
+                    className="message-delete-link"
+                    onClick={() => handleDelete(msg.id)}
+                    aria-label="Delete message"
+                  >
+                    Delete
+                  </button>
+                )}
               </div>
             )}
           </div>
@@ -284,6 +397,13 @@ export function MessageList({ roomId, messages, members, myRooms, onEdit, onReac
       })}
       <div ref={bottomRef} />
       {lightboxSrc && <ImageLightbox src={lightboxSrc} onClose={() => setLightboxSrc(null)} />}
+      {videoLightbox && (
+        <VideoLightbox
+          src={videoLightbox.src}
+          filename={videoLightbox.filename}
+          onClose={() => setVideoLightbox(null)}
+        />
+      )}
       {previewFile && (
         <FilePreviewModal
           roomId={roomId}

frontend/src/components/Modal.css

@@ -230,6 +230,45 @@
   color: var(--ds-muted);
 }
 
+.text-scale-options {
+  display: grid;
+  grid-template-columns: repeat(4, 1fr);
+  gap: var(--sp-2);
+  margin-bottom: var(--sp-4);
+}
+
+.text-scale-option {
+  display: flex;
+  flex-direction: column;
+  align-items: center;
+  gap: 4px;
+  background: var(--ds-surface-2);
+  border: 1px solid var(--ds-border);
+  border-radius: var(--radius);
+  padding: 10px 4px;
+  cursor: pointer;
+}
+
+.text-scale-option:hover {
+  border-color: var(--ds-accent);
+}
+
+.text-scale-option-selected {
+  border-color: var(--ds-accent);
+  box-shadow: 0 0 0 1px var(--ds-accent);
+}
+
+.text-scale-option-preview {
+  font-weight: 700;
+  color: var(--ds-text);
+  line-height: 1;
+}
+
+.text-scale-option-label {
+  font-size: 0.7rem;
+  color: var(--ds-muted);
+}
+
 .theme-swatch-preview-new {
   background: transparent;
   border-style: dashed;
@@ -389,6 +428,28 @@
   border-bottom: none;
 }
 
+.modal-list-row-button {
+  width: 100%;
+  background: transparent;
+  border-left: none;
+  border-right: none;
+  border-top: none;
+  text-align: left;
+  font: inherit;
+  color: inherit;
+  cursor: pointer;
+  border-radius: var(--radius);
+}
+
+.modal-list-row-button:hover:not(:disabled) {
+  background: var(--ds-surface-2);
+}
+
+.modal-list-row-button:disabled {
+  cursor: not-allowed;
+  opacity: 0.7;
+}
+
 .modal-list-row-body {
   flex: 1;
   min-width: 0;
@@ -407,6 +468,36 @@
   color: var(--ds-muted);
 }
 
+.custom-emoji-upload-preview {
+  display: block;
+  width: 64px;
+  height: 64px;
+  object-fit: contain;
+  margin-top: var(--sp-2);
+  background: var(--ds-surface-2);
+  border-radius: var(--radius);
+  border: 1px solid var(--ds-border);
+}
+
+.modal-list-row-action {
+  flex: none;
+  background: transparent;
+  border: none;
+  color: var(--ds-danger);
+  font-size: 0.76rem;
+  cursor: pointer;
+  padding: 4px 6px;
+}
+
+.modal-list-row-action:hover:not(:disabled) {
+  text-decoration: underline;
+}
+
+.modal-list-row-action:disabled {
+  cursor: not-allowed;
+  opacity: 0.6;
+}
+
 .profile-modal-avatar-row {
   display: flex;
   align-items: center;