fix: volume

.env.example

@@ -1,5 +1,6 @@
 DATABASE_URL=postgres://postgres:postgres@localhost:5432/chattz
 PORT=3000
+APP_BASE_URL=http://localhost:3000
 
 # Authentik OIDC app values
 OIDC_CLIENT_ID=replace-me
@@ -16,6 +17,9 @@ TURN_URLS=turn:turn.example.com:3478?transport=udp,turn:turn.example.com:3478?tr
 TURN_USERNAME=replace-me
 TURN_PASSWORD=replace-me
 
-# 32+ random chars; used to sign session cookies
+# Cloudflare R2 media uploads
-SESSION_SECRET=replace-with-long-random-secret
+R2_ACCOUNT_ID=replace-me
-COOKIE_SECURE=false
+R2_ACCESS_KEY_ID=replace-me
+R2_SECRET_ACCESS_KEY=replace-me
+R2_BUCKET=chattz-media
+MEDIA_BASE_URL=https://media.example.com

.forgejo/workflows/pipeline.yaml

@@ -19,17 +19,6 @@ jobs:
           VERSION=${GITHUB_REF_NAME#v}
           echo "Bumping version to $VERSION"
           npm version $VERSION --no-git-tag-version
-          
-          # Configure Git
-          git config user.name "Forgejo Actions"
-          git config user.email "actions@noreply.flegr.me"
-          
-          # Commit and push back to main if version changed
-          if [ -n "$(git status --porcelain package.json)" ]; then
-            git add package.json package-lock.json
-            git commit -m "chore: bump version to $VERSION [skip ci]"
-            git push origin HEAD:main
-          fi
       - run: npm ci
       - run: npm run dist:linux
       - name: Build Windows installer with 32-bit Wine prefix
@@ -50,11 +39,20 @@ jobs:
               cp "$file" "static/installers/$out"
             fi
           }
+          # Copy versioned artifacts for electron-updater
+          cp dist/*.AppImage static/installers/ || true
+          cp dist/*.exe static/installers/ || true
+          cp dist/*.rpm static/installers/ || true
+          cp dist/*.deb static/installers/ || true
+          cp dist/*.msi static/installers/ || true
+
+          # Maintain generic names for stable website links
           copy_first '*.rpm' 'chattz-linux.rpm'
           copy_first '*.deb' 'chattz-linux.deb'
           copy_first '*.AppImage' 'chattz-linux.AppImage'
           copy_first '*.exe' 'chattz-windows.exe'
           copy_first '*.msi' 'chattz-windows.msi'
+
           # Metadata files for electron-updater
           copy_first 'latest-linux.yml' 'latest-linux.yml'
           copy_first 'latest.yml' 'latest.yml'

Cargo.toml

@@ -5,17 +5,20 @@ edition = "2024"
 
 [dependencies]
 anyhow = "1"
+aws-config = { version = "1", default-features = false, features = ["behavior-version-latest", "rt-tokio", "rustls"] }
+aws-sdk-s3 = { version = "1", default-features = false, features = ["rt-tokio", "rustls"] }
 axum = { version = "0.8", features = ["macros", "ws", "multipart"] }
 chrono = { version = "0.4", features = ["serde"] }
 dotenvy = "0.15"
-jsonwebtoken = "9"
 reqwest = { version = "0.12", default-features = false, features = ["json", "rustls-tls"] }
-sea-orm = { version = "1.1", default-features = false, features = ["sqlx-postgres", "runtime-tokio-rustls", "macros", "with-chrono", "with-uuid"] }
+sea-orm = { version = "1.1", default-features = false, features = ["sqlx-postgres", "runtime-tokio-rustls", "macros", "with-chrono", "with-uuid", "mock"] }
 sea-orm-migration = { version = "1.1", default-features = false, features = ["sqlx-postgres", "runtime-tokio-rustls"] }
 serde = { version = "1", features = ["derive"] }
 serde_json = "1"
+sha2 = "0.10"
 futures-util = "0.3"
-tokio = { version = "1", features = ["macros", "rt-multi-thread"] }
+tokio = { version = "1", features = ["fs", "io-util", "macros", "rt-multi-thread"] }
+tower = { version = "0.5", features = ["util"] }
 tower-http = { version = "0.6", features = ["trace", "fs"] }
 tracing = "0.1"
 tracing-subscriber = { version = "0.3", features = ["env-filter", "fmt"] }

README.md

@@ -8,7 +8,7 @@ A simple single-instance Discord-style monolith in Rust using:
 ## What this includes
 
 - OIDC login flow (`/auth/login`, `/auth/callback`, `/auth/logout`)
-- Signed session cookie auth
+- HttpOnly session cookie auth
 - Channel voice chat over WebRTC (P2P mesh) with server WebSocket signaling
 - Guild invite codes (create + join)
 - Direct messages (DM) between users
@@ -41,6 +41,11 @@ For voice reliability on restrictive networks, configure TURN in `.env`:
 - `TURN_USERNAME`
 - `TURN_PASSWORD`
 
+For production deployments:
+- `APP_BASE_URL` must be your public app origin and should use `https`
+- `MEDIA_BASE_URL` should be a separate media origin for user uploads
+- uploads and soundboard require R2/object storage to be configured
+
 3. Run app:
 
 ```bash
@@ -55,7 +60,7 @@ Web UI is available at `http://localhost:${PORT}/`.
 ## Authentik setup notes
 
 Create an Authentik OAuth2/OIDC provider + application and set:
-- Redirect URI: `http://localhost:3000/auth/callback`
+- Redirect URI: `${APP_BASE_URL}/auth/callback`
 - Scopes including at least: `openid profile email`
 
 If you change `PORT`, update `OIDC_REDIRECT_URL` and this redirect URI to match.
@@ -91,6 +96,7 @@ For Authentik these are commonly under `/application/o/...` for the app slug.
 - `GET /channels/:channel_id/voice/ws` (WebSocket signaling)
 
 All endpoints except health and auth flow require the session cookie from successful login.
+Authenticated WebSocket connections (`/ws`, `/channels/:channel_id/voice/ws`) also use the same cookie session.
 
 ## Notes
 
@@ -98,6 +104,7 @@ This is intentionally minimal and monolithic (single process, single Postgres in
 Voice is implemented as browser-to-browser WebRTC audio with signaling in this server.
 For two users behind strict NAT/firewall, you may need TURN for reliable connectivity.
 The web UI remembers the last selected guild in browser local storage and auto-selects it on reload.
+User uploads are served from the configured media origin, not from `/static`.
 
 Mic filter modes in the UI:
 - `NSNet2 (Compat)`: always-on denoising mode (implemented using DeepFilterNet3 with lighter suppression preset)

desktop/index.html

@@ -1,3 +1,4 @@
+<!-- Generated from shared-html/index.template.html. Do not edit directly. -->
 <!doctype html>
 <html lang="en">
 
@@ -5,12 +6,9 @@
   <meta charset="UTF-8" />
   <meta name="viewport" content="width=device-width, initial-scale=1.0, viewport-fit=cover" />
   <title>Chattz</title>
-  <link rel="preconnect" href="https://fonts.googleapis.com">
+  <link rel="stylesheet" href="../static/styles.css" />
-  <link rel="preconnect" href="https://fonts.gstatic.com" crossorigin>
-  <link href="https://fonts.googleapis.com/css2?family=Inter:wght@400;500;600;700;800&display=swap" rel="stylesheet">
-  <link rel="stylesheet" href="styles.css" />
   <!-- Lucide Icons -->
-  <script src="https://unpkg.com/lucide@latest"></script>
+  <script src="../static/vendor/lucide.min.js"></script>
 </head>
 
 <body>
@@ -116,8 +114,7 @@
           <div class="user-actions">
             <div id="update-notifier" class="update-notifier hidden">
               <button id="update-download-btn" title="Download Update"><i data-lucide="download"></i></button>
-              <button id="update-install-btn" title="Install Update" class="hidden"><i
+              <button id="update-install-btn" title="Install Update" class="hidden"><i data-lucide="arrow-up-circle"></i></button>
-                  data-lucide="arrow-up-circle"></i></button>
             </div>
             <button id="user-settings-btn" title="Settings"><i data-lucide="settings"></i></button>
             <button id="logout-btn" title="Logout"><i data-lucide="log-out"></i></button>
@@ -144,6 +141,10 @@
 
       <div class="chat-input-wrapper">
         <form id="message-form" class="message-form">
+          <input id="media-file-input" type="file" class="hidden-file-input" accept="image/*,video/*,audio/*,.pdf,.txt,.zip,.rar,.7z,.tar,.gz,.json,.csv,.md" />
+          <button type="button" id="media-upload-btn" class="input-action-btn" title="Upload File">
+            <i data-lucide="paperclip"></i>
+          </button>
           <button type="button" id="gif-btn" class="input-action-btn" title="Open GIF Picker">
             <i data-lucide="image"></i>
           </button>
@@ -265,7 +266,17 @@
     </div>
   </div>
 
-  <script src="app.js?v=20260225-voice-debug-1" defer></script>
+  <div id="upload-limit-modal" class="modal-container hidden">
+    <div class="modal">
+      <h2>Upload Too Large</h2>
+      <p id="upload-limit-message" class="modal-copy">Uploads are limited to 50 MB per file.</p>
+      <div class="modal-footer">
+        <button type="button" class="submit-btn" id="upload-limit-ok">OK</button>
+      </div>
+    </div>
+  </div>
+
+  <script type="module" src="app.js?v=20260227-shared-core-1"></script>
 </body>
 
-</html>
+</html>

desktop/preload.js

@@ -1,12 +1,20 @@
 const { contextBridge, ipcRenderer } = require('electron');
 
+function onIpc(channel, callback) {
+    const listener = (_event, payload) => callback(payload);
+    ipcRenderer.on(channel, listener);
+    return () => ipcRenderer.removeListener(channel, listener);
+}
+
 contextBridge.exposeInMainWorld('electronAPI', {
     copyToClipboard: (text) => ipcRenderer.invoke('clipboard-write', text),
-    getConfig: () => ipcRenderer.invoke('get-config'),
+    getUpdateState: () => ipcRenderer.invoke('get-update-state'),
+    checkForUpdatesNow: () => ipcRenderer.invoke('check-for-updates-now'),
     checkForUpdates: () => ipcRenderer.send('check-for-updates'),
     downloadUpdate: () => ipcRenderer.send('download-update'),
     quitAndInstall: () => ipcRenderer.send('quit-and-install'),
-    onUpdateAvailable: (callback) => ipcRenderer.on('update-available', (event, info) => callback(info)),
+    onUpdateState: (callback) => onIpc('update-state', callback),
-    onUpdateDownloaded: (callback) => ipcRenderer.on('update-downloaded', (event, info) => callback(info)),
+    onUpdateAvailable: (callback) => onIpc('update-available', callback),
-    onUpdateError: (callback) => ipcRenderer.on('update-error', (event, error) => callback(error))
+    onUpdateDownloaded: (callback) => onIpc('update-downloaded', callback),
+    onUpdateError: (callback) => onIpc('update-error', callback)
 });

main.js

@@ -1,11 +1,146 @@
 const { app, BrowserWindow, session, desktopCapturer, ipcMain, clipboard } = require('electron');
 const { autoUpdater } = require('electron-updater');
 const path = require('path');
-const url = require('url');
+const packageJson = require('./package.json');
+const PERIODIC_UPDATE_CHECK_INTERVAL_MS = 1 * 60 * 1000;
+
+const updateState = {
+    status: 'idle', // idle | checking | available | downloading | downloaded | installing | not-available | error
+    info: null,
+    error: null,
+};
+
+function broadcastUpdateState() {
+    const wins = BrowserWindow.getAllWindows();
+    for (const win of wins) {
+        if (!win.isDestroyed()) {
+            win.webContents.send('update-state', updateState);
+        }
+    }
+}
+
+function isNewerVersionAvailable(info) {
+    const next = info && typeof info.version === 'string' ? info.version : '';
+    return Boolean(next) && next !== app.getVersion();
+}
+
+let updateCheckInProgress = false;
+let installInProgress = false;
+let periodicUpdateTimer = null;
+
+function resolveBackendUrl() {
+    const configuredUrl = (process.env.CHATTZ_URL || process.env.APP_BASE_URL || '').trim();
+    if (configuredUrl) {
+        return configuredUrl.replace(/\/$/, '');
+    }
+
+    const packagedFallback = typeof packageJson.homepage === 'string'
+        ? packageJson.homepage.trim()
+        : '';
+    if (app.isPackaged && packagedFallback) {
+        return packagedFallback.replace(/\/$/, '');
+    }
+
+    return 'http://localhost:3000';
+}
+
+function webContentsOrigin(webContents) {
+    if (!webContents || typeof webContents.getURL !== 'function') {
+        return null;
+    }
+    return safeOrigin(webContents.getURL());
+}
+
+async function runUpdateCheck(reason = 'manual') {
+    if (installInProgress) {
+        console.log(`Update check skipped (${reason}): install already in progress`);
+        return;
+    }
+    if (updateCheckInProgress) {
+        console.log(`Update check skipped (${reason}): another check is already in progress`);
+        return;
+    }
+    updateCheckInProgress = true;
+    updateState.status = 'checking';
+    updateState.error = null;
+    try {
+        const result = await autoUpdater.checkForUpdates();
+        const info = result && result.updateInfo ? result.updateInfo : null;
+        if (isNewerVersionAvailable(info)) {
+            updateState.status = 'available';
+            updateState.info = info;
+            updateState.error = null;
+        } else {
+            updateState.status = 'not-available';
+            updateState.info = info;
+            updateState.error = null;
+        }
+    } catch (err) {
+        updateState.status = 'error';
+        updateState.error = err && err.message ? err.message : String(err);
+        console.error(`Update check failed (${reason})`, err);
+    } finally {
+        updateCheckInProgress = false;
+        broadcastUpdateState();
+    }
+}
+
+function installDownloadedUpdate() {
+    if (installInProgress) {
+        console.log('Update install already in progress');
+        return;
+    }
+
+    installInProgress = true;
+    updateState.status = 'installing';
+    updateState.error = null;
+    broadcastUpdateState();
+
+    const wins = BrowserWindow.getAllWindows();
+    for (const win of wins) {
+        if (win.isDestroyed()) continue;
+        try {
+            win.removeAllListeners('close');
+            win.destroy();
+        } catch (err) {
+            console.warn('Failed to destroy window before update install', err);
+        }
+    }
+
+    setImmediate(() => {
+        try {
+            autoUpdater.quitAndInstall(false, true);
+        } catch (err) {
+            installInProgress = false;
+            updateState.status = 'error';
+            updateState.error = err && err.message ? err.message : String(err);
+            broadcastUpdateState();
+            console.error('quitAndInstall failed', err);
+        }
+    });
+
+    setTimeout(() => {
+        if (installInProgress) {
+            console.warn('Update install is still waiting for app shutdown');
+        }
+    }, 15000);
+}
+
+function startPeriodicUpdateChecks() {
+    if (periodicUpdateTimer || !app.isPackaged) {
+        return;
+    }
+
+    periodicUpdateTimer = setInterval(() => {
+        void runUpdateCheck('periodic');
+    }, PERIODIC_UPDATE_CHECK_INTERVAL_MS);
+}
 
 function createWindow() {
-    // Create a persistent session for chattz to keep the user logged in
     const sess = session.fromPartition('persist:chattz');
+    const backendUrl = resolveBackendUrl();
+    const backendOrigin = new URL(backendUrl).origin;
+    console.log(`Desktop backend URL: ${backendUrl}`);
 
     const win = new BrowserWindow({
         width: 1200,
@@ -14,52 +149,41 @@ function createWindow() {
         webPreferences: {
             nodeIntegration: false,
             contextIsolation: true,
-            webSecurity: false, // Required for cross-origin fetch/ws from file:// with cookies
             session: sess,
             preload: path.join(__dirname, 'desktop', 'preload.js')
         }
     });
 
     win.setAutoHideMenuBar(true);
-    win.setMenuBarVisibility(false);
+    win.setMenuBarVisibility(true);
 
-    ipcMain.handle('get-config', () => {
-        return {
-            backendUrl: (process.env.CHATTZ_URL || 'https://discord.flegr.me').replace(/\/$/, '')
-        };
-    });
-
-    ipcMain.handle('clipboard-write', (event, text) => {
-        clipboard.writeText(text);
-        return true;
-    });
-
-    // Auto-approve media permissions (camera, microphone)
     sess.setPermissionCheckHandler((webContents, permission) => {
-        if (permission === 'media' || permission === 'clipboard-read' || permission === 'clipboard-write') {
+        const origin = webContentsOrigin(webContents);
-            return true;
+        if (origin !== backendOrigin) return false;
-        }
+        return permission === 'media' || permission === 'clipboard-write';
-        return false;
     });
 
     sess.setPermissionRequestHandler((webContents, permission, callback) => {
-        if (permission === 'media' || permission === 'clipboard-read' || permission === 'clipboard-write') {
+        const origin = webContentsOrigin(webContents);
+        if (origin === backendOrigin && (permission === 'media' || permission === 'clipboard-write')) {
             callback(true);
         } else {
             callback(false);
         }
     });
 
-    // Handle screen share requests
     sess.setDisplayMediaRequestHandler((request, callback) => {
+        const origin = safeOrigin(request.frame?.url || win.webContents.getURL());
+        if (origin !== backendOrigin) {
+            callback(null);
+            return;
+        }
         desktopCapturer.getSources({ types: ['screen', 'window'] }).then((sources) => {
-            // Provide the first screen source by default, or implement a picker window here
             if (sources && sources.length > 0) {
-                // We prefer a screen over a window if available, simple heuristic
                 const screenSource = sources.find(s => s.id.startsWith('screen')) || sources[0];
                 callback({ video: screenSource, audio: 'loopback' });
             } else {
-                callback(null); // Reject safely
+                callback(null);
             }
         }).catch(err => {
             console.error("Failed to get desktop sources for screen share", err);
@@ -67,50 +191,18 @@ function createWindow() {
         });
     });
 
-    const backendUrl = (process.env.CHATTZ_URL || 'https://discord.flegr.me').replace(/\/$/, '');
+    win.loadURL(backendUrl).catch((err) => {
-    const indexPath = path.join(__dirname, 'desktop', 'index.html');
+        console.error(`Failed to load desktop app: ${err}`);
-
-    const loadDesktopApp = (queryParams = '') => {
-        const options = {};
-        if (queryParams) {
-            try {
-                options.query = Object.fromEntries(new URLSearchParams(queryParams));
-            } catch (e) {
-                console.error("Failed to parse query params", e);
-            }
-        }
-
-        // Use setImmediate to ensure the current navigation tick is cleared,
-        // which prevents ERR_ABORTED (-3) on some platforms when interrupting a redirect.
-        setImmediate(() => {
-            if (win.isDestroyed()) return;
-            win.loadFile(indexPath, options).catch((err) => {
-                // Ignore aborted errors as they often happen during fast redirects
-                if (err.toString().includes('-3') || err.code === -3) return;
-                console.error(`Failed to load desktop file: ${err}`);
-            });
-        });
-    };
-
-    // Use a navigation listener to detect when the remote login is complete
-    win.webContents.on('will-navigate', (event, navigatedUrl) => {
-        try {
-            const urlObj = new URL(navigatedUrl);
-            const backendObj = new URL(backendUrl);
-            // Detect the redirect back to the home page with a token
-            if (urlObj.origin === backendObj.origin && urlObj.pathname === '/') {
-                if (urlObj.searchParams.has('token')) {
-                    console.log("Detected login success redirect, returning to desktop UI...");
-                    event.preventDefault();
-                    loadDesktopApp(urlObj.search.slice(1));
-                }
-            }
-        } catch (e) {
-            console.error(e);
-        }
     });
 
-    loadDesktopApp();
+    // Ensure renderer receives latest updater state after any (re)load.
+    // Delay broadcast by 300ms to give the renderer time to register its
+    // onUpdateState IPC listener before we push state.
+    win.webContents.on('did-finish-load', () => {
+        setTimeout(() => {
+            if (!win.isDestroyed()) broadcastUpdateState();
+        }, 300);
+    });
 
     // Uncomment to debug
     // win.webContents.openDevTools();
@@ -120,6 +212,17 @@ app.commandLine.appendSwitch('disable-webrtc-hw-encoding'); // Sometime helps re
 app.commandLine.appendSwitch('log-level', '3'); // Silences standard Chromium warning logs (like SRTP transport unprotect logs which are benign timing issues)
 
 app.whenReady().then(() => {
+    ipcMain.handle('clipboard-write', (event, text) => {
+        clipboard.writeText(text);
+        return true;
+    });
+
+    ipcMain.handle('get-update-state', () => ({ ...updateState }));
+    ipcMain.handle('check-for-updates-now', async () => {
+        await runUpdateCheck('renderer-direct');
+        return { ...updateState };
+    });
+
     createWindow();
 
     // Configure Auto-Updater
@@ -127,38 +230,59 @@ app.whenReady().then(() => {
     autoUpdater.logger = console;
 
     autoUpdater.on('update-available', (info) => {
+        updateState.status = 'available';
+        updateState.info = info;
+        updateState.error = null;
+        broadcastUpdateState();
         const wins = BrowserWindow.getAllWindows();
         if (wins.length > 0) wins[0].webContents.send('update-available', info);
     });
 
+    autoUpdater.on('update-not-available', (info) => {
+        updateState.status = 'not-available';
+        updateState.info = info || null;
+        updateState.error = null;
+        broadcastUpdateState();
+    });
+
     autoUpdater.on('update-downloaded', (info) => {
+        updateState.status = 'downloaded';
+        updateState.info = info;
+        updateState.error = null;
+        broadcastUpdateState();
         const wins = BrowserWindow.getAllWindows();
         if (wins.length > 0) wins[0].webContents.send('update-downloaded', info);
     });
 
     autoUpdater.on('error', (err) => {
+        updateState.status = 'error';
+        updateState.error = err.message;
+        broadcastUpdateState();
         const wins = BrowserWindow.getAllWindows();
         if (wins.length > 0) wins[0].webContents.send('update-error', err.message);
     });
 
     ipcMain.on('check-for-updates', () => {
-        autoUpdater.checkForUpdatesAndNotify().catch(err => {
+        void runUpdateCheck('manual');
-            console.error("Manual update check failed", err);
-        });
     });
 
     ipcMain.on('download-update', () => {
+        if (installInProgress) return;
+        updateState.status = 'downloading';
+        updateState.error = null;
+        broadcastUpdateState();
         autoUpdater.downloadUpdate();
     });
 
     ipcMain.on('quit-and-install', () => {
-        autoUpdater.quitAndInstall();
+        installDownloadedUpdate();
     });
 
     // Check once on startup
     setTimeout(() => {
-        autoUpdater.checkForUpdatesAndNotify().catch(() => { });
+        void runUpdateCheck('startup');
     }, 5000);
+    startPeriodicUpdateChecks();
 
     app.on('activate', () => {
         if (BrowserWindow.getAllWindows().length === 0) {
@@ -172,3 +296,18 @@ app.on('window-all-closed', () => {
         app.quit();
     }
 });
+
+app.on('before-quit', () => {
+    if (periodicUpdateTimer) {
+        clearInterval(periodicUpdateTimer);
+        periodicUpdateTimer = null;
+    }
+});
+
+function safeOrigin(value) {
+    try {
+        return new URL(value).origin;
+    } catch (_) {
+        return null;
+    }
+}

package-lock.json

@@ -1,12 +1,12 @@
 {
     "name": "chattz-electron",
-    "version": "0.0.46",
+    "version": "0.0.50",
     "lockfileVersion": 3,
     "requires": true,
     "packages": {
         "": {
             "name": "chattz-electron",
-            "version": "0.0.46",
+            "version": "0.0.50",
             "dependencies": {
                 "electron-updater": "^6.8.3"
             },

package.json

@@ -1,6 +1,6 @@
 {
     "name": "chattz-electron",
-    "version": "0.0.46",
+    "version": "0.0.50",
     "description": "Electron frontend for Chattz",
     "author": "Pavel Flegr <pavelflegr@gmail.com>",
     "homepage": "https://discord.flegr.me",
@@ -10,17 +10,19 @@
     },
     "main": "main.js",
     "scripts": {
-        "start": "electron .",
+        "build:html": "node scripts/generate-html.js",
-        "dev": "electron .",
+        "start": "npm run build:html && electron .",
-        "dist": "electron-builder --publish never",
+        "dev": "npm run build:html && electron .",
-        "dist:linux": "electron-builder --linux --publish never",
+        "dist": "npm run build:html && electron-builder --publish never",
-        "dist:win": "electron-builder --win --publish never"
+        "dist:linux": "npm run build:html && electron-builder --linux --publish never",
+        "dist:win": "npm run build:html && electron-builder --win --publish never"
     },
     "build": {
         "appId": "me.flegr.chattz",
         "productName": "Chattz",
         "linux": {
             "target": [
+                "AppImage",
                 "rpm"
             ],
             "category": "Chat",
@@ -56,4 +58,4 @@
     "dependencies": {
         "electron-updater": "^6.8.3"
     }
-}
+}

scripts/generate-html.js

@@ -0,0 +1,57 @@
+const fs = require('fs');
+const path = require('path');
+
+const root = path.resolve(__dirname, '..');
+const templatePath = path.join(root, 'shared-html', 'index.template.html');
+const template = fs.readFileSync(templatePath, 'utf8');
+
+const updaterMarkup = `<div id="update-notifier" class="update-notifier hidden">
+              <button id="update-download-btn" title="Download Update"><i data-lucide="download"></i></button>
+              <button id="update-install-btn" title="Install Update" class="hidden"><i data-lucide="arrow-up-circle"></i></button>
+            </div>`;
+
+const variants = {
+  web: {
+    styles_href: '/static/styles.css',
+    lucide_src: '/static/vendor/lucide.min.js',
+    app_src: '/static/app.js?v=20260227-shared-core-1',
+    web_downloads: `<div class="auth-downloads">
+        <span>Desktop downloads:</span>
+        <a href="/static/installers/chattz-windows.exe">Windows</a>
+        <a href="/static/installers/chattz-linux.rpm">Linux (RPM)</a>
+      </div>`,
+    desktop_updater: updaterMarkup,
+    outPath: path.join(root, 'static', 'index.html'),
+  },
+  desktop: {
+    styles_href: '../static/styles.css',
+    lucide_src: '../static/vendor/lucide.min.js',
+    app_src: 'app.js?v=20260227-shared-core-1',
+    web_downloads: '',
+    desktop_updater: updaterMarkup,
+    outPath: path.join(root, 'desktop', 'index.html'),
+  },
+};
+
+for (const variant of Object.values(variants)) {
+  let output = template;
+  for (const [key, value] of Object.entries(variant)) {
+    if (key === 'outPath') continue;
+    const token = `{{${key}}}`;
+    if (value === '') {
+      output = output.replace(new RegExp(`^[ \\t]*\\{\\{${key}\\}\\}[ \\t]*\\n?`, 'm'), '');
+      continue;
+    }
+    output = output.replaceAll(token, value);
+  }
+
+  if (/\{\{[a-z_]+\}\}/i.test(output)) {
+    throw new Error(`Unresolved template placeholders remain in ${variant.outPath}`);
+  }
+
+  fs.writeFileSync(
+    variant.outPath,
+    `<!-- Generated from shared-html/index.template.html. Do not edit directly. -->\n${output}`,
+    'utf8'
+  );
+}

shared-html/index.template.html

@@ -0,0 +1,279 @@
+<!doctype html>
+<html lang="en">
+
+<head>
+  <meta charset="UTF-8" />
+  <meta name="viewport" content="width=device-width, initial-scale=1.0, viewport-fit=cover" />
+  <title>Chattz</title>
+  <link rel="stylesheet" href="{{styles_href}}" />
+  <!-- Lucide Icons -->
+  <script src="{{lucide_src}}"></script>
+</head>
+
+<body>
+  <div class="auth-screen" id="auth-screen">
+    <div class="auth-card">
+      <div class="brand-large">C</div>
+      <h1>Chattz</h1>
+      <p>Sign in to open your servers.</p>
+      <button id="login-btn">Login with Authentik</button>
+      {{web_downloads}}
+      <p id="status" class="status-line"></p>
+    </div>
+  </div>
+
+  <div class="shell hidden" id="main">
+    <aside class="server-rail">
+      <div class="brand" title="Home">
+        <i data-lucide="message-square"></i>
+      </div>
+      <div class="separator"></div>
+      <div id="guild-list" class="guild-list"></div>
+      <button id="add-guild-btn" class="guild-pill action-pill" title="Add a Server">
+        <i data-lucide="plus"></i>
+      </button>
+    </aside>
+
+    <aside class="channel-sidebar">
+      <header class="sidebar-header clickable" id="guild-header">
+        <h2 id="guild-title">No server selected</h2>
+        <div class="sidebar-header-actions">
+          <span id="invite-copied-badge" class="copied-badge hidden">Copied!</span>
+          <button id="create-invite-btn" class="header-action-btn" title="Create Invite Link">
+            <i data-lucide="link-2"></i>
+          </button>
+          <i data-lucide="chevron-down"></i>
+        </div>
+      </header>
+
+      <div class="sidebar-scroll">
+        <section class="sidebar-group">
+          <div class="group-title">
+            <i data-lucide="chevron-down" class="group-toggle"></i>
+            <span>Text Channels</span>
+            <button id="add-text-btn" class="add-btn" type="button" title="Create Text Channel">
+              <i data-lucide="plus"></i>
+            </button>
+          </div>
+          <div id="channel-list" class="channel-list"></div>
+        </section>
+
+        <section class="sidebar-group">
+          <div class="group-title">
+            <i data-lucide="chevron-down" class="group-toggle"></i>
+            <span>Voice Channels</span>
+            <button id="add-voice-btn" class="add-btn" type="button" title="Create Voice Channel">
+              <i data-lucide="plus"></i>
+            </button>
+          </div>
+          <div id="voice-channel-list" class="channel-list"></div>
+        </section>
+
+        <section class="sidebar-group">
+          <div class="group-title">
+            <i data-lucide="chevron-down" class="group-toggle"></i>
+            <span>Direct Messages</span>
+          </div>
+          <div id="dm-list" class="channel-list"></div>
+        </section>
+      </div>
+
+      <div class="sidebar-footer">
+        <div id="voice-connection" class="voice-connection hidden">
+          <div class="vc-info">
+            <i data-lucide="signal-high" class="vc-icon"></i>
+            <div class="vc-text">
+              <span class="vc-status">Voice Connected</span>
+              <span id="vc-channel-name" class="vc-name">General</span>
+            </div>
+            <div class="vc-actions">
+              <button id="voice-video-btn" title="Turn on Camera"><i data-lucide="video-off"></i></button>
+              <button id="voice-screen-btn" title="Share Screen"><i data-lucide="monitor-off"></i></button>
+              <button id="voice-mute-btn" title="Mute"><i data-lucide="mic"></i></button>
+              <button id="voice-leave-btn" title="Disconnect"><i data-lucide="phone-off"></i></button>
+            </div>
+          </div>
+          <div id="soundboard" class="soundboard-container hidden">
+            <div class="soundboard-header">
+              <span>Sound Board</span>
+              <span id="add-sound-btn" class="btn-add-sound">+ Add Sound</span>
+            </div>
+            <div id="soundboard-grid" class="soundboard-grid"></div>
+          </div>
+        </div>
+
+        <div class="user-panel">
+          <div class="avatar-wrapper">
+            <div id="user-avatar" class="avatar">U</div>
+            <div class="status-dot online"></div>
+          </div>
+          <div class="user-info">
+            <div id="user-name" class="display-name">Username</div>
+            <div class="user-status">Online</div>
+          </div>
+          <div class="user-actions">
+            {{desktop_updater}}
+            <button id="user-settings-btn" title="Settings"><i data-lucide="settings"></i></button>
+            <button id="logout-btn" title="Logout"><i data-lucide="log-out"></i></button>
+          </div>
+        </div>
+      </div>
+    </aside>
+
+    <main class="chat-pane">
+      <header class="chat-header">
+        <button id="mobile-menu-btn" class="mobile-toggle-btn" title="Menu">
+          <i data-lucide="menu"></i>
+        </button>
+        <i data-lucide="hash" class="header-icon"></i>
+        <h3 id="channel-title">Select a channel</h3>
+        <div style="flex:1"></div>
+        <button id="mobile-members-btn" class="mobile-toggle-btn" title="Members">
+          <i data-lucide="users"></i>
+        </button>
+      </header>
+
+      <div id="video-grid" class="video-grid hidden"></div>
+      <div id="message-list" class="message-list"></div>
+
+      <div class="chat-input-wrapper">
+        <form id="message-form" class="message-form">
+          <input id="media-file-input" type="file" class="hidden-file-input" accept="image/*,video/*,audio/*,.pdf,.txt,.zip,.rar,.7z,.tar,.gz,.json,.csv,.md" />
+          <button type="button" id="media-upload-btn" class="input-action-btn" title="Upload File">
+            <i data-lucide="paperclip"></i>
+          </button>
+          <button type="button" id="gif-btn" class="input-action-btn" title="Open GIF Picker">
+            <i data-lucide="image"></i>
+          </button>
+          <input id="message-body" autocomplete="off" placeholder="Message #channel" maxlength="4000" required />
+          <button type="submit" class="hidden"></button>
+        </form>
+      </div>
+    </main>
+
+    <aside class="utility-sidebar" id="utility-sidebar">
+      <header class="sidebar-header">
+        <h2>Members</h2>
+      </header>
+      <div class="member-list-wrapper">
+        <div id="member-list" class="member-list"></div>
+      </div>
+    </aside>
+  </div>
+
+  <div id="overlay" class="overlay hidden"></div>
+
+  <!-- Modals -->
+  <div id="gif-picker" class="modal-container hidden">
+    <div class="modal gif-modal">
+      <div class="modal-header">
+        <h2>Select GIF</h2>
+        <button type="button" class="close-btn" id="gif-picker-close">
+          <i data-lucide="x"></i>
+        </button>
+      </div>
+      <div class="gif-search-wrapper">
+        <input type="text" id="gif-search-input" placeholder="Search for GIFs..." autocomplete="off">
+        <i data-lucide="search" class="search-icon"></i>
+      </div>
+      <div id="gif-results" class="gif-results-grid">
+        <!-- GIF results will be injected here -->
+        <div class="gif-loading hidden">Loading...</div>
+      </div>
+    </div>
+  </div>
+  <div id="modal-container" class="modal-container hidden">
+    <div class="modal">
+      <h2 id="modal-title">Create Server</h2>
+      <form id="guild-form" class="modal-form">
+        <div class="form-item">
+          <label for="guild-name">SERVER NAME</label>
+          <input id="guild-name" placeholder="My Awesome Server" maxlength="64" required />
+        </div>
+        <div class="modal-footer">
+          <button type="button" class="cancel-btn" id="modal-cancel">Cancel</button>
+          <button type="submit" class="submit-btn">Create</button>
+        </div>
+      </form>
+    </div>
+  </div>
+
+  <div id="channel-modal" class="modal-container hidden">
+    <div class="modal">
+      <h2>Create Channel</h2>
+      <form id="channel-form" class="modal-form">
+        <div class="form-item">
+          <label>CHANNEL TYPE</label>
+          <div class="radio-group">
+            <label class="radio-item">
+              <input type="radio" name="channel-kind" value="text" checked>
+              <div class="radio-box">
+                <i data-lucide="hash"></i>
+                <div class="radio-text">
+                  <strong>Text</strong>
+                  <span>Send messages, images, and GIFs.</span>
+                </div>
+              </div>
+            </label>
+            <label class="radio-item">
+              <input type="radio" name="channel-kind" value="voice">
+              <div class="radio-box">
+                <i data-lucide="volume-2"></i>
+                <div class="radio-text">
+                  <strong>Voice</strong>
+                  <span>Hang out together with voice and video.</span>
+                </div>
+              </div>
+            </label>
+          </div>
+        </div>
+        <div class="form-item">
+          <label for="channel-name">CHANNEL NAME</label>
+          <input id="channel-name" placeholder="new-channel" maxlength="64" required />
+        </div>
+        <div class="modal-footer">
+          <button type="button" class="cancel-btn" id="channel-modal-cancel">Cancel</button>
+          <button type="submit" class="submit-btn">Create Channel</button>
+        </div>
+      </form>
+    </div>
+  </div>
+
+  <div id="sound-modal" class="modal-container hidden">
+    <div class="modal">
+      <h2>Add Sound</h2>
+      <form id="sound-form" class="modal-form">
+        <div class="form-item">
+          <label for="sound-name">NAME</label>
+          <input id="sound-name" placeholder="Quack" maxlength="32" required />
+        </div>
+        <div class="form-item">
+          <label for="sound-icon">ICON (Emoji or Initials)</label>
+          <input id="sound-icon" placeholder="🦆" maxlength="4" required />
+        </div>
+        <div class="form-item">
+          <label for="sound-file">AUDIO FILE (MP3/WAV)</label>
+          <input id="sound-file" type="file" accept="audio/*" required />
+        </div>
+        <div class="modal-footer">
+          <button type="button" class="cancel-btn" id="sound-modal-cancel">Cancel</button>
+          <button type="submit" class="submit-btn" id="sound-submit-btn">Add Sound</button>
+        </div>
+      </form>
+    </div>
+  </div>
+
+  <div id="upload-limit-modal" class="modal-container hidden">
+    <div class="modal">
+      <h2>Upload Too Large</h2>
+      <p id="upload-limit-message" class="modal-copy">Uploads are limited to 50 MB per file.</p>
+      <div class="modal-footer">
+        <button type="button" class="submit-btn" id="upload-limit-ok">OK</button>
+      </div>
+    </div>
+  </div>
+
+  <script type="module" src="{{app_src}}"></script>
+</body>
+
+</html>

src/auth.rs

@@ -1,33 +1,25 @@
-use std::time::{Duration, SystemTime, UNIX_EPOCH};
+use anyhow::{Result, anyhow};
-
-use anyhow::{Context, Result, anyhow};
 use axum::{
     Json,
     extract::{FromRef, FromRequestParts},
-    http::{StatusCode, request::Parts},
+    http::{HeaderMap, StatusCode, request::Parts},
     response::{IntoResponse, Response},
 };
-use jsonwebtoken::{DecodingKey, EncodingKey, Header, Validation, decode, encode};
+use chrono::{Duration, Utc};
-use serde::{Deserialize, Serialize};
+use serde::Serialize;
+use sha2::{Digest, Sha256};
 use uuid::Uuid;
 
 use crate::{AppState, db};
 
-const OAUTH_STATE_COOKIE: &str = "chattz_oauth_state";
+pub const OAUTH_STATE_COOKIE: &str = "chattz_oauth_state";
-const SESSION_TTL_SECS: u64 = 60 * 15; // 15 minutes
+pub const SESSION_COOKIE: &str = "chattz_session";
-const REFRESH_TTL_SECS: u64 = 60 * 60 * 24 * 30; // 30 days
+const SESSION_TTL_DAYS: i64 = 30;
-
-#[derive(Debug, Serialize, Deserialize, Clone)]
-pub struct SessionClaims {
-    pub sub: String,
-    pub kind: String, // "access" or "refresh"
-    pub exp: usize,
-    pub iat: usize,
-}
 
 #[derive(Debug, Clone)]
 pub struct AuthUser {
     pub id: Uuid,
+    pub session_id: String,
 }
 
 #[derive(Debug)]
@@ -44,6 +36,13 @@ impl ApiError {
         }
     }
 
+    pub fn forbidden(msg: &str) -> Self {
+        Self {
+            status: StatusCode::FORBIDDEN,
+            message: msg.to_string(),
+        }
+    }
+
     pub fn bad_request(msg: &str) -> Self {
         Self {
             status: StatusCode::BAD_REQUEST,
@@ -57,6 +56,13 @@ impl ApiError {
             message: msg.to_string(),
         }
     }
+
+    pub fn service_unavailable(msg: &str) -> Self {
+        Self {
+            status: StatusCode::SERVICE_UNAVAILABLE,
+            message: msg.to_string(),
+        }
+    }
 }
 
 #[derive(Serialize)]
@@ -84,29 +90,25 @@ impl From<anyhow::Error> for ApiError {
 
 impl<S> FromRequestParts<S> for AuthUser
 where
-    AppState: axum::extract::FromRef<S>,
+    AppState: FromRef<S>,
     S: Send + Sync,
 {
     type Rejection = ApiError;
 
     async fn from_request_parts(parts: &mut Parts, state: &S) -> Result<Self, Self::Rejection> {
         let app = AppState::from_ref(state);
+        let session_id = read_cookie_from_headers(&parts.headers, SESSION_COOKIE)
+            .ok_or_else(|| ApiError::unauthorized("missing session cookie"))?;
 
-        let token = read_bearer_token(parts)
+        let user_id = db::touch_active_session(&app.db, &session_id)
-            .or_else(|| read_query_token(parts))
-            .ok_or_else(|| ApiError::unauthorized("missing jwt token"))?;
-
-        let user_id = verify_session(&token, &app.settings.session_secret, "access")
-            .map_err(|_| ApiError::unauthorized("invalid or expired token"))?;
-
-        let exists = db::user_exists(&app.db, user_id)
             .await
-            .map_err(|_| ApiError::unauthorized("session user not found"))?;
+            .map_err(|_| ApiError::unauthorized("invalid or expired session"))?
-        if !exists {
+            .ok_or_else(|| ApiError::unauthorized("invalid or expired session"))?;
-            return Err(ApiError::unauthorized("session user not found"));
-        }
 
-        Ok(Self { id: user_id })
+        Ok(Self {
+            id: user_id,
+            session_id,
+        })
     }
 }
 
@@ -114,6 +116,14 @@ pub fn new_oauth_state() -> String {
     Uuid::new_v4().to_string()
 }
 
+pub fn new_session_id() -> String {
+    Uuid::new_v4().simple().to_string()
+}
+
+pub fn session_expiry() -> chrono::DateTime<chrono::FixedOffset> {
+    (Utc::now() + Duration::days(SESSION_TTL_DAYS)).fixed_offset()
+}
+
 pub fn make_oauth_state_cookie(value: &str, secure: bool) -> String {
     format!(
         "{name}={value}; Path=/; HttpOnly; SameSite=Lax; Max-Age=600{secure_flag}",
@@ -123,76 +133,32 @@ pub fn make_oauth_state_cookie(value: &str, secure: bool) -> String {
 }
 
 pub fn clear_oauth_state_cookie(secure: bool) -> String {
+    clear_cookie(OAUTH_STATE_COOKIE, secure, "Lax")
+}
+
+pub fn make_session_cookie(value: &str, secure: bool) -> String {
     format!(
-        "{name}=; Path=/; HttpOnly; SameSite=Lax; Max-Age=0{secure_flag}",
+        "{name}={value}; Path=/; HttpOnly; SameSite=Strict; Max-Age={ttl}{secure_flag}",
-        name = OAUTH_STATE_COOKIE,
+        name = SESSION_COOKIE,
+        ttl = Duration::days(SESSION_TTL_DAYS).num_seconds(),
         secure_flag = if secure { "; Secure" } else { "" }
     )
 }
 
-pub fn read_oauth_state_from_headers(headers: &axum::http::HeaderMap) -> Option<String> {
+pub fn clear_session_cookie(secure: bool) -> String {
+    clear_cookie(SESSION_COOKIE, secure, "Strict")
+}
+
+pub fn read_cookie_from_headers(headers: &HeaderMap, cookie_name: &str) -> Option<String> {
     let raw = headers.get(axum::http::header::COOKIE)?.to_str().ok()?;
     raw.split(';').find_map(|pair| {
         let mut kv = pair.trim().splitn(2, '=');
         let key = kv.next()?;
         let value = kv.next()?;
-        (key == OAUTH_STATE_COOKIE).then(|| value.to_string())
+        (key == cookie_name).then(|| value.to_string())
     })
 }
 
-pub fn new_jwt_tokens(user_id: Uuid, secret: &str) -> Result<(String, String)> {
-    let now = now_ts();
-
-    let access_claims = SessionClaims {
-        sub: user_id.to_string(),
-        kind: "access".to_string(),
-        iat: now as usize,
-        exp: (now + SESSION_TTL_SECS) as usize,
-    };
-
-    let refresh_claims = SessionClaims {
-        sub: user_id.to_string(),
-        kind: "refresh".to_string(),
-        iat: now as usize,
-        exp: (now + REFRESH_TTL_SECS) as usize,
-    };
-
-    let access_token = encode(
-        &Header::default(),
-        &access_claims,
-        &EncodingKey::from_secret(secret.as_bytes()),
-    )
-    .context("failed to encode access token")?;
-
-    let refresh_token = encode(
-        &Header::default(),
-        &refresh_claims,
-        &EncodingKey::from_secret(secret.as_bytes()),
-    )
-    .context("failed to encode refresh token")?;
-
-    Ok((access_token, refresh_token))
-}
-
-pub fn verify_session(token: &str, secret: &str, expected_kind: &str) -> Result<Uuid> {
-    let mut validation = Validation::default();
-    validation.validate_exp = true;
-
-    let data = decode::<SessionClaims>(
-        token,
-        &DecodingKey::from_secret(secret.as_bytes()),
-        &validation,
-    )
-    .context("failed to decode session token")?;
-
-    if data.claims.kind != expected_kind {
-        return Err(anyhow!("invalid token kind"));
-    }
-
-    let user_id = Uuid::parse_str(&data.claims.sub).context("invalid sub in session token")?;
-    Ok(user_id)
-}
-
 pub fn validate_oauth_state(expected_cookie: Option<String>, query_state: &str) -> Result<()> {
     let expected = expected_cookie.ok_or_else(|| anyhow!("missing oauth state cookie"))?;
     if expected != query_state {
@@ -201,37 +167,113 @@ pub fn validate_oauth_state(expected_cookie: Option<String>, query_state: &str)
     Ok(())
 }
 
-fn read_bearer_token(parts: &Parts) -> Option<String> {
+pub fn user_agent_hash(headers: &HeaderMap) -> Option<String> {
-    let raw = parts
+    header_hash(headers, axum::http::header::USER_AGENT.as_str())
-        .headers
+}
-        .get(axum::http::header::AUTHORIZATION)?
+
-        .to_str()
+pub fn ip_hash(headers: &HeaderMap) -> Option<String> {
-        .ok()?;
+    headers
-    if raw.starts_with("Bearer ") {
+        .get("x-forwarded-for")
-        Some(raw["Bearer ".len()..].trim().to_string())
+        .and_then(|v| v.to_str().ok())
-    } else {
+        .and_then(|raw| raw.split(',').next().map(str::trim))
-        None
+        .filter(|value| !value.is_empty())
+        .map(hash_string)
+        .or_else(|| header_hash(headers, "x-real-ip"))
+}
+
+pub fn origin_matches(headers: &HeaderMap, expected_origin: &str) -> bool {
+    headers
+        .get(axum::http::header::ORIGIN)
+        .and_then(|value| value.to_str().ok())
+        .map(|origin| origin == expected_origin)
+        .unwrap_or(false)
+}
+
+fn header_hash(headers: &HeaderMap, header_name: &str) -> Option<String> {
+    headers
+        .get(header_name)
+        .and_then(|v| v.to_str().ok())
+        .filter(|value| !value.trim().is_empty())
+        .map(hash_string)
+}
+
+fn hash_string(value: &str) -> String {
+    let mut hasher = Sha256::new();
+    hasher.update(value.as_bytes());
+    let digest = hasher.finalize();
+    let mut out = String::with_capacity(digest.len() * 2);
+    for byte in digest {
+        out.push(nibble_to_hex(byte >> 4));
+        out.push(nibble_to_hex(byte & 0x0f));
+    }
+    out
+}
+
+fn nibble_to_hex(value: u8) -> char {
+    match value {
+        0..=9 => (b'0' + value) as char,
+        10..=15 => (b'a' + (value - 10)) as char,
+        _ => unreachable!(),
     }
 }
 
-fn read_query_token(parts: &Parts) -> Option<String> {
+fn clear_cookie(name: &str, secure: bool, same_site: &str) -> String {
-    let query = parts.uri.query()?;
+    format!(
+        "{name}=; Path=/; HttpOnly; SameSite={same_site}; Max-Age=0{secure_flag}",
+        secure_flag = if secure { "; Secure" } else { "" }
+    )
+}
 
-    // Simple query param parsing without pulling in url::Url overhead
+#[cfg(test)]
-    for pair in query.split('&') {
+mod tests {
-        let mut kv = pair.splitn(2, '=');
+    use super::{
-        let key = kv.next()?;
+        SESSION_COOKIE, clear_session_cookie, hash_string, make_session_cookie, origin_matches,
-        let value = kv.next()?;
+        read_cookie_from_headers,
-        if key == "token" {
+    };
-            return Some(value.to_string());
+    use axum::http::{HeaderMap, header};
-        }
+
+    #[test]
+    fn hash_string_is_stable() {
+        assert_eq!(
+            hash_string("example"),
+            "50d858e0985ecc7f60418aaf0cc5ab587f42c2570a884095a9e8ccacd0f6545c"
+        );
     }
-    None
-}
 
-fn now_ts() -> u64 {
+    #[test]
-    SystemTime::now()
+    fn reads_named_cookie_from_header() {
-        .duration_since(UNIX_EPOCH)
+        let mut headers = HeaderMap::new();
-        .unwrap_or_else(|_| Duration::from_secs(0))
+        headers.insert(
-        .as_secs()
+            header::COOKIE,
+            "other=value; chattz_session=session-123; another=ok"
+                .parse()
+                .unwrap(),
+        );
+
+        assert_eq!(
+            read_cookie_from_headers(&headers, SESSION_COOKIE),
+            Some("session-123".to_string())
+        );
+    }
+
+    #[test]
+    fn origin_match_requires_exact_origin() {
+        let mut headers = HeaderMap::new();
+        headers.insert(header::ORIGIN, "http://localhost:3000".parse().unwrap());
+
+        assert!(origin_matches(&headers, "http://localhost:3000"));
+        assert!(!origin_matches(&headers, "https://localhost:3000"));
+    }
+
+    #[test]
+    fn session_cookie_has_strict_policy_and_clear_cookie_expires() {
+        let session_cookie = make_session_cookie("session-123", false);
+        let cleared_cookie = clear_session_cookie(false);
+
+        assert!(session_cookie.contains("HttpOnly"));
+        assert!(session_cookie.contains("SameSite=Strict"));
+        assert!(session_cookie.contains("Max-Age="));
+        assert!(cleared_cookie.contains("SameSite=Strict"));
+        assert!(cleared_cookie.contains("Max-Age=0"));
+    }
 }

src/chat.rs

@@ -1,27 +1,30 @@
-use crate::AppState;
+use std::collections::HashMap;
+
 use axum::extract::ws::{Message, WebSocket};
 use futures_util::{SinkExt, StreamExt};
 use serde::{Deserialize, Serialize};
-use std::collections::HashMap;
 use tokio::sync::{RwLock, mpsc};
 use uuid::Uuid;
 
+use crate::{AppState, db};
+
 #[derive(Clone)]
 pub struct ChatClient {
     tx: mpsc::UnboundedSender<ServerEvent>,
     is_idle: bool,
 }
 
-#[derive(Serialize, Clone)]
+#[derive(Serialize, Clone, Debug, PartialEq, Eq)]
 pub struct OnlineUser {
     pub user_id: Uuid,
+    pub online: bool,
     pub idle: bool,
 }
 
 #[derive(Default)]
 pub struct ChatHub {
-    // user_id -> client
+    // user_id -> connection_id -> client
-    clients: RwLock<HashMap<Uuid, ChatClient>>,
+    clients: RwLock<HashMap<Uuid, HashMap<Uuid, ChatClient>>>,
 }
 
 #[derive(Serialize, Clone)]
@@ -45,85 +48,113 @@ pub enum ServerEvent {
 #[derive(Deserialize)]
 #[serde(tag = "type", rename_all = "snake_case")]
 enum ClientEvent {
-    // Currently no interactive client events for the general chat WS
     Ping,
     SetIdleStatus { is_idle: bool },
 }
 
 impl ChatHub {
-    pub async fn add_client(&self, user_id: Uuid, tx: mpsc::UnboundedSender<ServerEvent>) {
+    pub async fn add_client(
+        &self,
+        user_id: Uuid,
+        connection_id: Uuid,
+        tx: mpsc::UnboundedSender<ServerEvent>,
+    ) -> Option<OnlineUser> {
         let mut clients = self.clients.write().await;
-        clients.insert(user_id, ChatClient { tx, is_idle: false });
+        let previous = aggregate_presence(clients.get(&user_id), user_id);
-    }
 
-    pub async fn remove_client(&self, user_id: Uuid) {
-        let mut clients = self.clients.write().await;
-        clients.remove(&user_id);
-    }
-
-    pub async fn get_online_users(&self) -> Vec<OnlineUser> {
-        let clients = self.clients.read().await;
         clients
+            .entry(user_id)
+            .or_default()
+            .insert(connection_id, ChatClient { tx, is_idle: false });
+
+        let current = aggregate_presence(clients.get(&user_id), user_id);
+        presence_delta(previous, current)
+    }
+
+    pub async fn remove_client(&self, user_id: Uuid, connection_id: Uuid) -> Option<OnlineUser> {
+        let mut clients = self.clients.write().await;
+        let previous = aggregate_presence(clients.get(&user_id), user_id);
+
+        if let Some(connections) = clients.get_mut(&user_id) {
+            connections.remove(&connection_id);
+            if connections.is_empty() {
+                clients.remove(&user_id);
+            }
+        }
+
+        let current = aggregate_presence(clients.get(&user_id), user_id);
+        presence_delta(previous, current)
+    }
+
+    pub async fn get_online_users_for(&self, visible_user_ids: &[Uuid]) -> Vec<OnlineUser> {
+        let clients = self.clients.read().await;
+        visible_user_ids
             .iter()
-            .map(|(id, client)| OnlineUser {
+            .filter_map(|user_id| aggregate_presence(clients.get(user_id), *user_id))
-                user_id: *id,
+            .filter(|presence| presence.online)
-                idle: client.is_idle,
-            })
             .collect()
     }
 
-    pub async fn broadcast_all(&self, event: ServerEvent) {
-        let clients = self.clients.read().await;
-        for client in clients.values() {
-            let _ = client.tx.send(event.clone());
-        }
-    }
-
-    pub async fn broadcast_to_user(&self, user_id: Uuid, event: ServerEvent) {
-        let clients = self.clients.read().await;
-        if let Some(client) = clients.get(&user_id) {
-            let _ = client.tx.send(event);
-        }
-    }
-
     pub async fn broadcast_to_many(&self, user_ids: Vec<Uuid>, event: ServerEvent) {
         let clients = self.clients.read().await;
         for user_id in user_ids {
-            if let Some(client) = clients.get(&user_id) {
+            if let Some(connections) = clients.get(&user_id) {
+                for client in connections.values() {
+                    let _ = client.tx.send(event.clone());
+                }
+            }
+        }
+    }
+
+    pub async fn broadcast_to_user(&self, user_id: Uuid, event: ServerEvent) {
+        let clients = self.clients.read().await;
+        if let Some(connections) = clients.get(&user_id) {
+            for client in connections.values() {
                 let _ = client.tx.send(event.clone());
             }
         }
     }
 
-    pub async fn set_idle_status(&self, user_id: Uuid, is_idle: bool) {
+    pub async fn set_idle_status(
+        &self,
+        user_id: Uuid,
+        connection_id: Uuid,
+        is_idle: bool,
+    ) -> Option<OnlineUser> {
+        let mut clients = self.clients.write().await;
+        let previous = aggregate_presence(clients.get(&user_id), user_id);
+
+        if let Some(connections) = clients.get_mut(&user_id)
+            && let Some(client) = connections.get_mut(&connection_id)
         {
-            let mut clients = self.clients.write().await;
+            client.is_idle = is_idle;
-            if let Some(client) = clients.get_mut(&user_id) {
-                client.is_idle = is_idle;
-            }
         }
-        self.broadcast_all(ServerEvent::UserPresence {
+
-            user_id,
+        let current = aggregate_presence(clients.get(&user_id), user_id);
-            online: true,
+        presence_delta(previous, current)
-            idle: is_idle,
-        })
-        .await;
     }
 }
 
 pub async fn handle_socket(state: AppState, socket: WebSocket, user_id: Uuid) {
     let (mut ws_sender, mut ws_receiver) = socket.split();
     let (tx, mut rx) = mpsc::unbounded_channel::<ServerEvent>();
+    let connection_id = Uuid::new_v4();
 
-    state.chat.add_client(user_id, tx).await;
+    if let Some(presence) = state.chat.add_client(user_id, connection_id, tx).await {
-    state
+        if let Ok(visible_user_ids) = db::list_visible_user_ids(&state.db, user_id).await {
-        .chat
+            state
-        .broadcast_all(ServerEvent::UserPresence {
+                .chat
-            user_id,
+                .broadcast_to_many(
-            online: true,
+                    visible_user_ids,
-            idle: false,
+                    ServerEvent::UserPresence {
-        })
+                        user_id: presence.user_id,
-        .await;
+                        online: presence.online,
+                        idle: presence.idle,
+                    },
+                )
+                .await;
+        }
+    }
 
     let send_task = tokio::spawn(async move {
         while let Some(event) = rx.recv().await {
@@ -142,8 +173,24 @@ pub async fn handle_socket(state: AppState, socket: WebSocket, user_id: Uuid) {
             Message::Text(text) => {
                 if let Ok(ClientEvent::SetIdleStatus { is_idle }) =
                     serde_json::from_str::<ClientEvent>(&text)
+                    && let Some(presence) = state
+                        .chat
+                        .set_idle_status(user_id, connection_id, is_idle)
+                        .await
+                    && let Ok(visible_user_ids) =
+                        db::list_visible_user_ids(&state.db, user_id).await
                 {
-                    state.chat.set_idle_status(user_id, is_idle).await;
+                    state
+                        .chat
+                        .broadcast_to_many(
+                            visible_user_ids,
+                            ServerEvent::UserPresence {
+                                user_id: presence.user_id,
+                                online: presence.online,
+                                idle: presence.idle,
+                            },
+                        )
+                        .await;
                 }
             }
             _ => {}
@@ -151,13 +198,157 @@ pub async fn handle_socket(state: AppState, socket: WebSocket, user_id: Uuid) {
     }
 
     send_task.abort();
-    state.chat.remove_client(user_id).await;
+    if let Some(presence) = state.chat.remove_client(user_id, connection_id).await
-    state
+        && let Ok(visible_user_ids) = db::list_visible_user_ids(&state.db, user_id).await
-        .chat
+    {
-        .broadcast_all(ServerEvent::UserPresence {
+        state
-            user_id,
+            .chat
+            .broadcast_to_many(
+                visible_user_ids,
+                ServerEvent::UserPresence {
+                    user_id: presence.user_id,
+                    online: presence.online,
+                    idle: presence.idle,
+                },
+            )
+            .await;
+    }
+}
+
+fn aggregate_presence(
+    connections: Option<&HashMap<Uuid, ChatClient>>,
+    user_id: Uuid,
+) -> Option<OnlineUser> {
+    let connections = connections?;
+    if connections.is_empty() {
+        return None;
+    }
+
+    let idle = connections.values().all(|client| client.is_idle);
+    Some(OnlineUser {
+        user_id,
+        online: true,
+        idle,
+    })
+}
+
+fn presence_delta(previous: Option<OnlineUser>, current: Option<OnlineUser>) -> Option<OnlineUser> {
+    match (previous, current) {
+        (None, None) => None,
+        (Some(prev), Some(curr)) if prev == curr => None,
+        (Some(prev), None) => Some(OnlineUser {
+            user_id: prev.user_id,
             online: false,
             idle: false,
-        })
+        }),
-        .await;
+        (_, Some(curr)) => Some(curr),
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::{ChatHub, OnlineUser, ServerEvent};
+    use serde_json::json;
+    use tokio::sync::mpsc;
+    use uuid::Uuid;
+
+    #[tokio::test]
+    async fn multiple_connections_keep_user_online_until_last_disconnect() {
+        let hub = ChatHub::default();
+        let user_id = Uuid::new_v4();
+        let first_connection = Uuid::new_v4();
+        let second_connection = Uuid::new_v4();
+        let (tx1, _rx1) = mpsc::unbounded_channel();
+        let (tx2, _rx2) = mpsc::unbounded_channel();
+
+        let first_presence = hub.add_client(user_id, first_connection, tx1).await;
+        let second_presence = hub.add_client(user_id, second_connection, tx2).await;
+        let after_first_disconnect = hub.remove_client(user_id, first_connection).await;
+        let after_last_disconnect = hub.remove_client(user_id, second_connection).await;
+
+        assert_eq!(
+            first_presence,
+            Some(OnlineUser {
+                user_id,
+                online: true,
+                idle: false,
+            })
+        );
+        assert_eq!(second_presence, None);
+        assert_eq!(after_first_disconnect, None);
+        assert_eq!(
+            after_last_disconnect,
+            Some(OnlineUser {
+                user_id,
+                online: false,
+                idle: false,
+            })
+        );
+    }
+
+    #[tokio::test]
+    async fn idle_status_only_flips_when_all_connections_are_idle() {
+        let hub = ChatHub::default();
+        let user_id = Uuid::new_v4();
+        let first_connection = Uuid::new_v4();
+        let second_connection = Uuid::new_v4();
+        let (tx1, _rx1) = mpsc::unbounded_channel();
+        let (tx2, _rx2) = mpsc::unbounded_channel();
+
+        hub.add_client(user_id, first_connection, tx1).await;
+        hub.add_client(user_id, second_connection, tx2).await;
+
+        let first_idle = hub.set_idle_status(user_id, first_connection, true).await;
+        let second_idle = hub.set_idle_status(user_id, second_connection, true).await;
+        let active_again = hub.set_idle_status(user_id, first_connection, false).await;
+
+        assert_eq!(first_idle, None);
+        assert_eq!(
+            second_idle,
+            Some(OnlineUser {
+                user_id,
+                online: true,
+                idle: true,
+            })
+        );
+        assert_eq!(
+            active_again,
+            Some(OnlineUser {
+                user_id,
+                online: true,
+                idle: false,
+            })
+        );
+    }
+
+    #[tokio::test]
+    async fn broadcast_to_user_reaches_all_active_connections() {
+        let hub = ChatHub::default();
+        let user_id = Uuid::new_v4();
+        let first_connection = Uuid::new_v4();
+        let second_connection = Uuid::new_v4();
+        let (tx1, mut rx1) = mpsc::unbounded_channel();
+        let (tx2, mut rx2) = mpsc::unbounded_channel();
+
+        hub.add_client(user_id, first_connection, tx1).await;
+        hub.add_client(user_id, second_connection, tx2).await;
+
+        hub.broadcast_to_user(
+            user_id,
+            ServerEvent::DmCreated {
+                other_user_id: Uuid::new_v4(),
+                message: json!({ "body": "hello" }),
+            },
+        )
+        .await;
+
+        assert!(matches!(
+            rx1.try_recv(),
+            Ok(ServerEvent::DmCreated { message, .. }) if message["body"] == "hello"
+        ));
+        assert!(matches!(
+            rx2.try_recv(),
+            Ok(ServerEvent::DmCreated { message, .. }) if message["body"] == "hello"
+        ));
+    }
 }

src/config.rs

@@ -1,8 +1,11 @@
-use anyhow::{Context, Result};
+use anyhow::{Context, Result, anyhow};
+use reqwest::Url;
 
 #[derive(Clone, Debug)]
 pub struct Settings {
     pub port: u16,
+    pub app_base_url: String,
+    pub app_origin: String,
     pub database_url: String,
     pub oidc_client_id: String,
     pub oidc_client_secret: String,
@@ -11,21 +14,36 @@ pub struct Settings {
     pub oidc_userinfo_url: String,
     pub oidc_redirect_url: String,
     pub oidc_scopes: String,
-    pub session_secret: String,
+    pub session_cookie_secure: bool,
-    pub cookie_secure: bool,
     pub stun_urls: Vec<String>,
     pub turn_urls: Vec<String>,
     pub turn_username: Option<String>,
     pub turn_password: Option<String>,
+    pub media: Option<MediaSettings>,
+}
+
+#[derive(Clone, Debug)]
+pub struct MediaSettings {
+    pub account_id: String,
+    pub access_key_id: String,
+    pub secret_access_key: String,
+    pub bucket: String,
+    pub public_base_url: String,
 }
 
 impl Settings {
     pub fn from_env() -> Result<Self> {
+        let app_base_url = required("APP_BASE_URL")?;
+        let app_url = Url::parse(&app_base_url).context("APP_BASE_URL must be a valid URL")?;
+        let app_origin = origin_from_url(&app_url)?;
+
         Ok(Self {
             port: std::env::var("PORT")
                 .unwrap_or_else(|_| "3000".into())
                 .parse()
                 .context("PORT must be a valid u16")?,
+            app_base_url: trim_trailing_slash(&app_base_url),
+            app_origin,
             database_url: required("DATABASE_URL")?,
             oidc_client_id: required("OIDC_CLIENT_ID")?,
             oidc_client_secret: required("OIDC_CLIENT_SECRET")?,
@@ -33,20 +51,51 @@ impl Settings {
             oidc_token_url: required("OIDC_TOKEN_URL")?,
             oidc_userinfo_url: required("OIDC_USERINFO_URL")?,
             oidc_redirect_url: required("OIDC_REDIRECT_URL")?,
-            oidc_scopes: std::env::var("OIDC_SCOPES").unwrap_or_else(|_| "openid profile email".to_string()),
+            oidc_scopes: std::env::var("OIDC_SCOPES")
-            session_secret: required("SESSION_SECRET")?,
+                .unwrap_or_else(|_| "openid profile email".to_string()),
-            cookie_secure: std::env::var("COOKIE_SECURE")
+            session_cookie_secure: requires_secure_cookie(&app_url)?,
-                .unwrap_or_else(|_| "false".into())
-                .parse()
-                .context("COOKIE_SECURE must be true/false")?,
             stun_urls: parse_csv_env("STUN_URLS", "stun:stun.l.google.com:19302"),
             turn_urls: parse_csv_env("TURN_URLS", ""),
             turn_username: optional("TURN_USERNAME"),
             turn_password: optional("TURN_PASSWORD"),
+            media: MediaSettings::from_env()?,
         })
     }
 }
 
+impl MediaSettings {
+    fn from_env() -> Result<Option<Self>> {
+        let account_id = optional("R2_ACCOUNT_ID");
+        let access_key_id = optional("R2_ACCESS_KEY_ID");
+        let secret_access_key = optional("R2_SECRET_ACCESS_KEY");
+        let bucket = optional("R2_BUCKET");
+        let public_base_url = optional("MEDIA_BASE_URL").or_else(|| optional("R2_PUBLIC_BASE_URL"));
+
+        if account_id.is_none()
+            && access_key_id.is_none()
+            && secret_access_key.is_none()
+            && bucket.is_none()
+            && public_base_url.is_none()
+        {
+            return Ok(None);
+        }
+
+        Ok(Some(Self {
+            account_id: account_id.context("missing env var R2_ACCOUNT_ID")?,
+            access_key_id: access_key_id.context("missing env var R2_ACCESS_KEY_ID")?,
+            secret_access_key: secret_access_key.context("missing env var R2_SECRET_ACCESS_KEY")?,
+            bucket: bucket.context("missing env var R2_BUCKET")?,
+            public_base_url: trim_trailing_slash(
+                &public_base_url.context("missing env var MEDIA_BASE_URL")?,
+            ),
+        }))
+    }
+
+    pub fn endpoint_url(&self) -> String {
+        format!("https://{}.r2.cloudflarestorage.com", self.account_id)
+    }
+}
+
 fn required(name: &str) -> Result<String> {
     std::env::var(name).with_context(|| format!("missing env var {name}"))
 }
@@ -66,3 +115,105 @@ fn parse_csv_env(name: &str, default_value: &str) -> Vec<String> {
         .map(ToString::to_string)
         .collect()
 }
+
+fn origin_from_url(url: &Url) -> Result<String> {
+    let host = url
+        .host_str()
+        .ok_or_else(|| anyhow!("APP_BASE_URL must include a host"))?;
+    let mut origin = format!("{}://{}", url.scheme(), host);
+    if let Some(port) = url.port() {
+        origin.push(':');
+        origin.push_str(&port.to_string());
+    }
+    Ok(origin)
+}
+
+fn requires_secure_cookie(url: &Url) -> Result<bool> {
+    match url.scheme() {
+        "https" => Ok(true),
+        "http" => {
+            let host = url
+                .host_str()
+                .ok_or_else(|| anyhow!("APP_BASE_URL must include a host"))?;
+            if matches!(host, "localhost" | "127.0.0.1" | "::1") {
+                Ok(false)
+            } else {
+                Err(anyhow!(
+                    "APP_BASE_URL must use https outside localhost when session cookies are enabled"
+                ))
+            }
+        }
+        other => Err(anyhow!("APP_BASE_URL scheme {other} is not supported")),
+    }
+}
+
+fn trim_trailing_slash(value: &str) -> String {
+    value.trim_end_matches('/').to_string()
+}
+
+#[cfg(test)]
+mod tests {
+    use super::{MediaSettings, origin_from_url, requires_secure_cookie, trim_trailing_slash};
+    use reqwest::Url;
+
+    #[test]
+    fn origin_from_url_preserves_explicit_port() {
+        let url = Url::parse("https://chat.example.com:8443/app").unwrap();
+        let origin = origin_from_url(&url).unwrap();
+
+        assert_eq!(origin, "https://chat.example.com:8443");
+    }
+
+    #[test]
+    fn secure_cookie_is_required_for_https_origins() {
+        let url = Url::parse("https://chat.example.com").unwrap();
+
+        assert_eq!(requires_secure_cookie(&url).unwrap(), true);
+    }
+
+    #[test]
+    fn localhost_http_is_allowed_without_secure_cookie() {
+        let url = Url::parse("http://localhost:3000").unwrap();
+
+        assert_eq!(requires_secure_cookie(&url).unwrap(), false);
+    }
+
+    #[test]
+    fn non_localhost_http_is_rejected() {
+        let url = Url::parse("http://chat.example.com").unwrap();
+        let err = requires_secure_cookie(&url).unwrap_err();
+
+        assert!(
+            err.to_string()
+                .contains("APP_BASE_URL must use https outside localhost")
+        );
+    }
+
+    #[test]
+    fn trim_trailing_slash_removes_only_suffix_slashes() {
+        assert_eq!(
+            trim_trailing_slash("https://chat.example.com///"),
+            "https://chat.example.com"
+        );
+        assert_eq!(
+            trim_trailing_slash("https://chat.example.com/app"),
+            "https://chat.example.com/app"
+        );
+    }
+
+    #[test]
+    fn media_endpoint_url_uses_account_id() {
+        let media = MediaSettings {
+            account_id: "acct123".to_string(),
+            access_key_id: "key".to_string(),
+            secret_access_key: "secret".to_string(),
+            bucket: "bucket".to_string(),
+            public_base_url: "https://media.example.com".to_string(),
+        };
+
+        assert_eq!(
+            media.endpoint_url(),
+            "https://acct123.r2.cloudflarestorage.com"
+        );
+    }
+}

src/db.rs

@@ -1,20 +1,22 @@
+use std::collections::HashSet;
+
 use anyhow::{Result, anyhow};
 use chrono::{Duration, Utc};
 use sea_orm::{
     ActiveModelTrait, ActiveValue::Set, ColumnTrait, Condition, DatabaseConnection,
     DatabaseTransaction, EntityTrait, PaginatorTrait, QueryFilter, QueryOrder, QuerySelect,
-    TransactionTrait, sea_query::OnConflict,
+    Statement, TransactionTrait, sea_query::OnConflict,
 };
 use uuid::Uuid;
 
 use crate::{
     entity::{
-        channels, direct_messages, guild_members, guilds, invites, messages, soundboard_sounds,
+        attachments, channels, direct_messages, guild_members, guilds, invites, messages, sessions,
-        users,
+        soundboard_sounds, users,
     },
     models::{
-        BasicUser, Channel, DmConversation, DmMessageWithAuthor, Guild, Invite, MessageWithAuthor,
+        Attachment, BasicUser, Channel, DmConversation, DmMessageWithAuthor, Guild, Invite,
-        SoundboardSound, User,
+        MessageWithAuthor, SoundboardSound, User,
     },
 };
 
@@ -26,6 +28,88 @@ pub async fn user_exists(db: &DatabaseConnection, user_id: Uuid) -> Result<bool>
     Ok(count > 0)
 }
 
+pub async fn create_session(
+    db: &DatabaseConnection,
+    session_id: &str,
+    user_id: Uuid,
+    expires_at: chrono::DateTime<chrono::FixedOffset>,
+    user_agent_hash: Option<String>,
+    ip_hash: Option<String>,
+) -> Result<()> {
+    sessions::Entity::insert(sessions::ActiveModel {
+        id: Set(session_id.to_string()),
+        user_id: Set(user_id),
+        expires_at: Set(expires_at),
+        created_at: Set(Utc::now().fixed_offset()),
+        last_seen_at: Set(Utc::now().fixed_offset()),
+        revoked_at: Set(None),
+        user_agent_hash: Set(user_agent_hash),
+        ip_hash: Set(ip_hash),
+    })
+    .exec(db)
+    .await?;
+
+    Ok(())
+}
+
+pub async fn touch_active_session(
+    db: &DatabaseConnection,
+    session_id: &str,
+) -> Result<Option<Uuid>> {
+    let session = sessions::Entity::find_by_id(session_id.to_string())
+        .one(db)
+        .await?;
+
+    let Some(session) = session else {
+        return Ok(None);
+    };
+
+    if session.revoked_at.is_some() || session.expires_at <= Utc::now().fixed_offset() {
+        return Ok(None);
+    }
+
+    let user_id = session.user_id;
+    sessions::Entity::update_many()
+        .col_expr(
+            sessions::Column::LastSeenAt,
+            sea_orm::sea_query::Expr::value(Utc::now().fixed_offset()),
+        )
+        .filter(sessions::Column::Id.eq(session_id.to_string()))
+        .exec(db)
+        .await?;
+    Ok(Some(user_id))
+}
+
+pub async fn revoke_session(db: &DatabaseConnection, session_id: &str) -> Result<()> {
+    if let Some(session) = sessions::Entity::find_by_id(session_id.to_string())
+        .one(db)
+        .await?
+    {
+        sessions::Entity::update_many()
+            .col_expr(
+                sessions::Column::RevokedAt,
+                sea_orm::sea_query::Expr::value(Some(Utc::now().fixed_offset())),
+            )
+            .filter(sessions::Column::Id.eq(session.id))
+            .exec(db)
+            .await?;
+    }
+
+    Ok(())
+}
+
+pub async fn cleanup_sessions(db: &DatabaseConnection) -> Result<()> {
+    sessions::Entity::delete_many()
+        .filter(
+            Condition::any()
+                .add(sessions::Column::ExpiresAt.lte(Utc::now().fixed_offset()))
+                .add(sessions::Column::RevokedAt.is_not_null()),
+        )
+        .exec(db)
+        .await?;
+    Ok(())
+}
+
 pub async fn upsert_user_from_oidc(
     db: &DatabaseConnection,
     oidc_sub: &str,
@@ -106,18 +190,58 @@ pub async fn list_guilds_for_user(db: &DatabaseConnection, user_id: Uuid) -> Res
         .collect())
 }
 
+pub async fn list_visible_user_ids(db: &DatabaseConnection, user_id: Uuid) -> Result<Vec<Uuid>> {
+    let guild_ids: Vec<Uuid> = guild_members::Entity::find()
+        .filter(guild_members::Column::UserId.eq(user_id))
+        .select_only()
+        .column(guild_members::Column::GuildId)
+        .into_tuple()
+        .all(db)
+        .await?;
+
+    let mut visible = HashSet::from([user_id]);
+
+    if !guild_ids.is_empty() {
+        let guild_users = guild_members::Entity::find()
+            .filter(guild_members::Column::GuildId.is_in(guild_ids))
+            .all(db)
+            .await?;
+        visible.extend(guild_users.into_iter().map(|membership| membership.user_id));
+    }
+
+    let dm_rows = direct_messages::Entity::find()
+        .filter(
+            Condition::any()
+                .add(direct_messages::Column::SenderUserId.eq(user_id))
+                .add(direct_messages::Column::RecipientUserId.eq(user_id)),
+        )
+        .all(db)
+        .await?;
+
+    for row in dm_rows {
+        if row.sender_user_id == user_id {
+            visible.insert(row.recipient_user_id);
+        } else {
+            visible.insert(row.sender_user_id);
+        }
+    }
+
+    Ok(visible.into_iter().collect())
+}
+
 pub async fn create_guild(
     db: &DatabaseConnection,
     owner_user_id: Uuid,
     name: &str,
 ) -> Result<Guild> {
+    let txn = db.begin().await?;
     let guild = guilds::Entity::insert(guilds::ActiveModel {
         id: Set(Uuid::new_v4()),
         name: Set(name.to_string()),
         owner_user_id: Set(owner_user_id),
         ..Default::default()
     })
-    .exec_with_returning(db)
+    .exec_with_returning(&txn)
     .await?;
 
     guild_members::Entity::insert(guild_members::ActiveModel {
@@ -133,17 +257,13 @@ pub async fn create_guild(
         .do_nothing()
         .to_owned(),
     )
-    .exec(db)
+    .exec(&txn)
     .await?;
 
+    txn.commit().await?;
     Ok(map_guild(guild))
 }
 
-pub async fn get_guild_by_id(db: &DatabaseConnection, guild_id: Uuid) -> Result<Option<Guild>> {
-    let row = guilds::Entity::find_by_id(guild_id).one(db).await?;
-    Ok(row.map(map_guild))
-}
-
 pub async fn is_guild_owner(
     db: &DatabaseConnection,
     guild_id: Uuid,
@@ -197,7 +317,12 @@ pub async fn create_invite(
 pub async fn join_invite(db: &DatabaseConnection, code: &str, user_id: Uuid) -> Result<Guild> {
     let txn = db.begin().await?;
 
-    let invite = invites::Entity::find_by_id(code.to_string())
+    let invite = invites::Entity::find()
+        .from_raw_sql(Statement::from_sql_and_values(
+            sea_orm::DatabaseBackend::Postgres,
+            r#"SELECT * FROM invites WHERE code = $1 FOR UPDATE"#,
+            [code.into()],
+        ))
         .one(&txn)
         .await?
         .ok_or_else(|| anyhow!("invite not found"))?;
@@ -350,6 +475,63 @@ pub async fn create_message(
         author_user_id: model.author_user_id,
         author_display_name: user.display_name,
         body: model.body,
+        attachments: Vec::new(),
+        created_at: model.created_at,
+    })
+}
+
+pub async fn create_message_with_attachment(
+    db: &DatabaseConnection,
+    channel_id: Uuid,
+    author_user_id: Uuid,
+    body: &str,
+    object_key: &str,
+    media_url: &str,
+    mime_type: &str,
+    size_bytes: i64,
+    original_filename: &str,
+) -> Result<MessageWithAuthor> {
+    let txn = db.begin().await?;
+
+    let model = messages::Entity::insert(messages::ActiveModel {
+        id: Set(Uuid::new_v4()),
+        channel_id: Set(channel_id),
+        author_user_id: Set(author_user_id),
+        body: Set(body.to_string()),
+        ..Default::default()
+    })
+    .exec_with_returning(&txn)
+    .await?;
+
+    let attachment = attachments::Entity::insert(attachments::ActiveModel {
+        id: Set(Uuid::new_v4()),
+        channel_message_id: Set(Some(model.id)),
+        direct_message_id: Set(None),
+        uploader_user_id: Set(author_user_id),
+        object_key: Set(object_key.to_string()),
+        media_url: Set(media_url.to_string()),
+        mime_type: Set(mime_type.to_string()),
+        size_bytes: Set(size_bytes),
+        original_filename: Set(original_filename.to_string()),
+        ..Default::default()
+    })
+    .exec_with_returning(&txn)
+    .await?;
+
+    let user = users::Entity::find_by_id(author_user_id)
+        .one(&txn)
+        .await?
+        .ok_or_else(|| anyhow!("author not found"))?;
+
+    txn.commit().await?;
+
+    Ok(MessageWithAuthor {
+        id: model.id,
+        channel_id: model.channel_id,
+        author_user_id: model.author_user_id,
+        author_display_name: user.display_name,
+        body: model.body,
+        attachments: vec![map_attachment(attachment)],
         created_at: model.created_at,
     })
 }
@@ -367,6 +549,10 @@ pub async fn list_messages(
         .all(db)
         .await?;
 
+    let attachment_map =
+        list_attachments_for_channel_messages(db, rows.iter().map(|(msg, _)| msg.id).collect())
+            .await?;
+
     Ok(rows
         .into_iter()
         .map(|(msg, user)| {
@@ -379,6 +565,7 @@ pub async fn list_messages(
                 author_user_id: msg.author_user_id,
                 author_display_name,
                 body: msg.body,
+                attachments: attachment_map.get(&msg.id).cloned().unwrap_or_default(),
                 created_at: msg.created_at,
             }
         })
@@ -412,6 +599,63 @@ pub async fn create_direct_message(
         recipient_user_id: model.recipient_user_id,
         author_display_name: user.display_name,
         body: model.body,
+        attachments: Vec::new(),
+        created_at: model.created_at,
+    })
+}
+
+pub async fn create_direct_message_with_attachment(
+    db: &DatabaseConnection,
+    sender_user_id: Uuid,
+    recipient_user_id: Uuid,
+    body: &str,
+    object_key: &str,
+    media_url: &str,
+    mime_type: &str,
+    size_bytes: i64,
+    original_filename: &str,
+) -> Result<DmMessageWithAuthor> {
+    let txn = db.begin().await?;
+
+    let model = direct_messages::Entity::insert(direct_messages::ActiveModel {
+        id: Set(Uuid::new_v4()),
+        sender_user_id: Set(sender_user_id),
+        recipient_user_id: Set(recipient_user_id),
+        body: Set(body.to_string()),
+        ..Default::default()
+    })
+    .exec_with_returning(&txn)
+    .await?;
+
+    let attachment = attachments::Entity::insert(attachments::ActiveModel {
+        id: Set(Uuid::new_v4()),
+        channel_message_id: Set(None),
+        direct_message_id: Set(Some(model.id)),
+        uploader_user_id: Set(sender_user_id),
+        object_key: Set(object_key.to_string()),
+        media_url: Set(media_url.to_string()),
+        mime_type: Set(mime_type.to_string()),
+        size_bytes: Set(size_bytes),
+        original_filename: Set(original_filename.to_string()),
+        ..Default::default()
+    })
+    .exec_with_returning(&txn)
+    .await?;
+
+    let user = users::Entity::find_by_id(sender_user_id)
+        .one(&txn)
+        .await?
+        .ok_or_else(|| anyhow!("sender not found"))?;
+
+    txn.commit().await?;
+
+    Ok(DmMessageWithAuthor {
+        id: model.id,
+        author_user_id: model.sender_user_id,
+        recipient_user_id: model.recipient_user_id,
+        author_display_name: user.display_name,
+        body: model.body,
+        attachments: vec![map_attachment(attachment)],
         created_at: model.created_at,
     })
 }
@@ -454,6 +698,9 @@ pub async fn list_direct_messages(
         .map(|u| (u.id, u.display_name))
         .collect();
 
+    let attachment_map =
+        list_attachments_for_direct_messages(db, rows.iter().map(|msg| msg.id).collect()).await?;
+
     Ok(rows
         .into_iter()
         .map(|msg| DmMessageWithAuthor {
@@ -465,11 +712,64 @@ pub async fn list_direct_messages(
                 .cloned()
                 .unwrap_or_else(|| "Unknown User".to_string()),
             body: msg.body,
+            attachments: attachment_map.get(&msg.id).cloned().unwrap_or_default(),
             created_at: msg.created_at,
         })
         .collect())
 }
 
+async fn list_attachments_for_channel_messages(
+    db: &DatabaseConnection,
+    message_ids: Vec<Uuid>,
+) -> Result<std::collections::HashMap<Uuid, Vec<Attachment>>> {
+    if message_ids.is_empty() {
+        return Ok(std::collections::HashMap::new());
+    }
+
+    let rows = attachments::Entity::find()
+        .filter(attachments::Column::ChannelMessageId.is_in(message_ids))
+        .order_by_asc(attachments::Column::CreatedAt)
+        .all(db)
+        .await?;
+
+    let mut grouped = std::collections::HashMap::<Uuid, Vec<Attachment>>::new();
+    for row in rows {
+        if let Some(message_id) = row.channel_message_id {
+            grouped
+                .entry(message_id)
+                .or_default()
+                .push(map_attachment(row));
+        }
+    }
+    Ok(grouped)
+}
+
+async fn list_attachments_for_direct_messages(
+    db: &DatabaseConnection,
+    message_ids: Vec<Uuid>,
+) -> Result<std::collections::HashMap<Uuid, Vec<Attachment>>> {
+    if message_ids.is_empty() {
+        return Ok(std::collections::HashMap::new());
+    }
+
+    let rows = attachments::Entity::find()
+        .filter(attachments::Column::DirectMessageId.is_in(message_ids))
+        .order_by_asc(attachments::Column::CreatedAt)
+        .all(db)
+        .await?;
+
+    let mut grouped = std::collections::HashMap::<Uuid, Vec<Attachment>>::new();
+    for row in rows {
+        if let Some(message_id) = row.direct_message_id {
+            grouped
+                .entry(message_id)
+                .or_default()
+                .push(map_attachment(row));
+        }
+    }
+    Ok(grouped)
+}
+
 pub async fn list_dm_conversations(
     db: &DatabaseConnection,
     current_user_id: Uuid,
@@ -543,6 +843,16 @@ fn map_guild(model: guilds::Model) -> Guild {
     }
 }
 
+fn map_attachment(model: attachments::Model) -> Attachment {
+    Attachment {
+        id: model.id,
+        media_url: model.media_url,
+        mime_type: model.mime_type,
+        size_bytes: model.size_bytes,
+        original_filename: model.original_filename,
+    }
+}
+
 fn map_channel(model: channels::Model) -> Channel {
     Channel {
         id: model.id,
@@ -612,7 +922,10 @@ pub async fn create_sound(
     created_by_user_id: Uuid,
     name: &str,
     icon: &str,
-    file_path: &str,
+    object_key: &str,
+    media_url: &str,
+    mime_type: &str,
+    size_bytes: i64,
 ) -> Result<SoundboardSound> {
     let model = soundboard_sounds::Entity::insert(soundboard_sounds::ActiveModel {
         id: Set(Uuid::new_v4()),
@@ -620,7 +933,13 @@ pub async fn create_sound(
         created_by_user_id: Set(created_by_user_id),
         name: Set(name.to_string()),
         icon: Set(icon.to_string()),
-        file_path: Set(file_path.to_string()),
+        object_key: Set(Some(object_key.to_string())),
+        media_url: Set(media_url.to_string()),
+        mime_type: Set(Some(mime_type.to_string())),
+        size_bytes: Set(Some(size_bytes)),
+        // Keep the legacy column populated until every deployment has applied
+        // the nullable migration and old fallback paths are fully removed.
+        file_path: Set(Some(media_url.to_string())),
         ..Default::default()
     })
     .exec_with_returning(db)
@@ -634,6 +953,11 @@ pub async fn get_sound_by_id(db: &DatabaseConnection, id: Uuid) -> Result<Option
     Ok(row.map(map_sound))
 }
 
+pub async fn get_sound_object_key(db: &DatabaseConnection, id: Uuid) -> Result<Option<String>> {
+    let row = soundboard_sounds::Entity::find_by_id(id).one(db).await?;
+    Ok(row.and_then(|sound| sound.object_key))
+}
+
 pub async fn delete_sound(db: &DatabaseConnection, id: Uuid) -> Result<()> {
     soundboard_sounds::Entity::delete_by_id(id).exec(db).await?;
     Ok(())
@@ -645,8 +969,321 @@ fn map_sound(model: soundboard_sounds::Model) -> SoundboardSound {
         guild_id: model.guild_id,
         name: model.name,
         icon: model.icon,
-        file_path: model.file_path,
+        media_url: model.media_url,
+        mime_type: model.mime_type,
+        size_bytes: model.size_bytes,
         created_by_user_id: model.created_by_user_id,
         created_at: model.created_at,
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use super::{create_guild, create_sound, join_invite, list_visible_user_ids, validate_invite};
+    use crate::entity::{direct_messages, guild_members, guilds, invites, soundboard_sounds};
+    use chrono::{Duration, Utc};
+    use sea_orm::{DatabaseBackend, MockDatabase, MockExecResult, Value};
+    use std::collections::{BTreeMap, BTreeSet};
+    use uuid::Uuid;
+
+    #[tokio::test]
+    async fn visible_users_include_self_shared_guilds_and_dm_partners() {
+        let current_user_id = Uuid::new_v4();
+        let guild_a = Uuid::new_v4();
+        let guild_b = Uuid::new_v4();
+        let guild_peer = Uuid::new_v4();
+        let shared_dm_peer = Uuid::new_v4();
+
+        let db = MockDatabase::new(DatabaseBackend::Postgres)
+            .append_query_results([vec![
+                BTreeMap::from([("guild_id".to_string(), Value::from(guild_a))]),
+                BTreeMap::from([("guild_id".to_string(), Value::from(guild_b))]),
+            ]])
+            .append_query_results([vec![
+                guild_members::Model {
+                    guild_id: guild_a,
+                    user_id: current_user_id,
+                    created_at: Utc::now().fixed_offset(),
+                },
+                guild_members::Model {
+                    guild_id: guild_b,
+                    user_id: current_user_id,
+                    created_at: Utc::now().fixed_offset(),
+                },
+                guild_members::Model {
+                    guild_id: guild_a,
+                    user_id: guild_peer,
+                    created_at: Utc::now().fixed_offset(),
+                },
+            ]])
+            .append_query_results([vec![
+                direct_messages::Model {
+                    id: Uuid::new_v4(),
+                    sender_user_id: current_user_id,
+                    recipient_user_id: shared_dm_peer,
+                    body: "hello".to_string(),
+                    created_at: Utc::now().fixed_offset(),
+                },
+                direct_messages::Model {
+                    id: Uuid::new_v4(),
+                    sender_user_id: shared_dm_peer,
+                    recipient_user_id: current_user_id,
+                    body: "hi".to_string(),
+                    created_at: Utc::now().fixed_offset(),
+                },
+            ]])
+            .into_connection();
+
+        let visible = list_visible_user_ids(&db, current_user_id).await.unwrap();
+        let visible: BTreeSet<_> = visible.into_iter().collect();
+
+        assert_eq!(
+            visible,
+            BTreeSet::from([current_user_id, guild_peer, shared_dm_peer])
+        );
+    }
+
+    #[tokio::test]
+    async fn visible_users_returns_self_when_no_relationships_exist() {
+        let current_user_id = Uuid::new_v4();
+        let db = MockDatabase::new(DatabaseBackend::Postgres)
+            .append_query_results([Vec::<BTreeMap<String, Value>>::new()])
+            .append_query_results([Vec::<direct_messages::Model>::new()])
+            .into_connection();
+
+        let visible = list_visible_user_ids(&db, current_user_id).await.unwrap();
+
+        assert_eq!(visible, vec![current_user_id]);
+    }
+
+    #[test]
+    fn validate_invite_rejects_expired_invites() {
+        let invite = invites::Model {
+            code: "expired".to_string(),
+            guild_id: Uuid::new_v4(),
+            created_by_user_id: Uuid::new_v4(),
+            created_at: Utc::now().fixed_offset(),
+            expires_at: Some((Utc::now() - Duration::minutes(1)).fixed_offset()),
+            max_uses: Some(5),
+            use_count: 0,
+        };
+
+        let err = validate_invite(&invite).unwrap_err();
+        assert!(err.to_string().contains("invite expired"));
+    }
+
+    #[test]
+    fn validate_invite_rejects_exhausted_invites() {
+        let invite = invites::Model {
+            code: "used".to_string(),
+            guild_id: Uuid::new_v4(),
+            created_by_user_id: Uuid::new_v4(),
+            created_at: Utc::now().fixed_offset(),
+            expires_at: Some((Utc::now() + Duration::minutes(5)).fixed_offset()),
+            max_uses: Some(1),
+            use_count: 1,
+        };
+
+        let err = validate_invite(&invite).unwrap_err();
+        assert!(err.to_string().contains("invite exhausted"));
+    }
+
+    #[test]
+    fn validate_invite_accepts_active_invites() {
+        let invite = invites::Model {
+            code: "active".to_string(),
+            guild_id: Uuid::new_v4(),
+            created_by_user_id: Uuid::new_v4(),
+            created_at: Utc::now().fixed_offset(),
+            expires_at: Some((Utc::now() + Duration::minutes(5)).fixed_offset()),
+            max_uses: Some(3),
+            use_count: 1,
+        };
+
+        validate_invite(&invite).unwrap();
+    }
+
+    #[tokio::test]
+    async fn create_guild_runs_guild_and_membership_in_one_transaction() {
+        let owner_user_id = Uuid::new_v4();
+        let guild_id = Uuid::new_v4();
+        let created_at = Utc::now().fixed_offset();
+        let db = MockDatabase::new(DatabaseBackend::Postgres)
+            .append_query_results([vec![guilds::Model {
+                id: guild_id,
+                name: "Guild".to_string(),
+                owner_user_id,
+                created_at,
+            }]])
+            .append_exec_results([MockExecResult {
+                last_insert_id: 0,
+                rows_affected: 1,
+            }])
+            .into_connection();
+
+        let guild = create_guild(&db, owner_user_id, "Guild").await.unwrap();
+        let transaction_log = format!("{:?}", db.into_transaction_log());
+
+        assert_eq!(guild.id, guild_id);
+        assert!(transaction_log.contains("BEGIN"), "{transaction_log}");
+        assert!(transaction_log.contains("guilds"), "{transaction_log}");
+        assert!(
+            transaction_log.contains("guild_members"),
+            "{transaction_log}"
+        );
+        assert!(transaction_log.contains("COMMIT"), "{transaction_log}");
+
+        let guild_insert = transaction_log.find("guilds");
+        let membership_insert = transaction_log.find("guild_members");
+        assert!(guild_insert.is_some() && membership_insert.is_some());
+        assert!(guild_insert.unwrap() < membership_insert.unwrap());
+    }
+
+    #[tokio::test]
+    async fn join_invite_locks_invite_and_updates_use_count_in_one_transaction() {
+        let user_id = Uuid::new_v4();
+        let guild_id = Uuid::new_v4();
+        let created_by_user_id = Uuid::new_v4();
+        let created_at = Utc::now().fixed_offset();
+        let invite = invites::Model {
+            code: "invite123".to_string(),
+            guild_id,
+            created_by_user_id,
+            created_at,
+            expires_at: Some((Utc::now() + Duration::minutes(5)).fixed_offset()),
+            max_uses: Some(5),
+            use_count: 0,
+        };
+        let updated_invite = invites::Model {
+            use_count: 1,
+            ..invite.clone()
+        };
+        let guild = guilds::Model {
+            id: guild_id,
+            name: "Guild".to_string(),
+            owner_user_id: created_by_user_id,
+            created_at,
+        };
+
+        let db = MockDatabase::new(DatabaseBackend::Postgres)
+            .append_query_results([vec![invite]])
+            .append_query_results([Vec::<guild_members::Model>::new()])
+            .append_exec_results([MockExecResult {
+                last_insert_id: 0,
+                rows_affected: 1,
+            }])
+            .append_query_results([vec![updated_invite]])
+            .append_query_results([vec![guild]])
+            .into_connection();
+
+        let joined_guild = join_invite(&db, "invite123", user_id).await.unwrap();
+        let transaction_log = format!("{:?}", db.into_transaction_log());
+
+        assert_eq!(joined_guild.id, guild_id);
+        assert!(transaction_log.contains("BEGIN"), "{transaction_log}");
+        assert!(transaction_log.contains("FOR UPDATE"), "{transaction_log}");
+        assert!(
+            transaction_log.contains("guild_members"),
+            "{transaction_log}"
+        );
+        assert!(transaction_log.contains("UPDATE"), "{transaction_log}");
+        assert!(transaction_log.contains("invites"), "{transaction_log}");
+        assert!(transaction_log.contains("COMMIT"), "{transaction_log}");
+    }
+
+    #[tokio::test]
+    async fn join_invite_does_not_increment_use_count_for_existing_member() {
+        let user_id = Uuid::new_v4();
+        let guild_id = Uuid::new_v4();
+        let created_by_user_id = Uuid::new_v4();
+        let created_at = Utc::now().fixed_offset();
+        let invite = invites::Model {
+            code: "invite123".to_string(),
+            guild_id,
+            created_by_user_id,
+            created_at,
+            expires_at: Some((Utc::now() + Duration::minutes(5)).fixed_offset()),
+            max_uses: Some(5),
+            use_count: 3,
+        };
+        let existing_member = guild_members::Model {
+            guild_id,
+            user_id,
+            created_at,
+        };
+        let guild = guilds::Model {
+            id: guild_id,
+            name: "Guild".to_string(),
+            owner_user_id: created_by_user_id,
+            created_at,
+        };
+
+        let db = MockDatabase::new(DatabaseBackend::Postgres)
+            .append_query_results([vec![invite]])
+            .append_query_results([vec![existing_member]])
+            .append_exec_results([MockExecResult {
+                last_insert_id: 0,
+                rows_affected: 1,
+            }])
+            .append_query_results([vec![guild]])
+            .into_connection();
+
+        let joined_guild = join_invite(&db, "invite123", user_id).await.unwrap();
+        let transaction_log = format!("{:?}", db.into_transaction_log());
+
+        assert_eq!(joined_guild.id, guild_id);
+        assert!(transaction_log.contains("FOR UPDATE"), "{transaction_log}");
+        assert!(
+            transaction_log.contains("guild_members"),
+            "{transaction_log}"
+        );
+        assert!(transaction_log.contains("COMMIT"), "{transaction_log}");
+        assert!(
+            !transaction_log.contains("UPDATE \"invites\""),
+            "{transaction_log}"
+        );
+    }
+
+    #[tokio::test]
+    async fn create_sound_keeps_legacy_file_path_populated() {
+        let guild_id = Uuid::new_v4();
+        let sound_id = Uuid::new_v4();
+        let created_by_user_id = Uuid::new_v4();
+        let created_at = Utc::now().fixed_offset();
+        let media_url = "https://media.example.com/soundboard/test.mp3";
+        let db = MockDatabase::new(DatabaseBackend::Postgres)
+            .append_query_results([vec![soundboard_sounds::Model {
+                id: sound_id,
+                guild_id,
+                name: "Airhorn".to_string(),
+                icon: "AH".to_string(),
+                object_key: Some("soundboard/test.mp3".to_string()),
+                media_url: media_url.to_string(),
+                mime_type: Some("audio/mpeg".to_string()),
+                size_bytes: Some(1234),
+                file_path: Some(media_url.to_string()),
+                created_by_user_id,
+                created_at,
+            }]])
+            .into_connection();
+
+        let sound = create_sound(
+            &db,
+            guild_id,
+            created_by_user_id,
+            "Airhorn",
+            "AH",
+            "soundboard/test.mp3",
+            media_url,
+            "audio/mpeg",
+            1234,
+        )
+        .await
+        .unwrap();
+        let transaction_log = format!("{:?}", db.into_transaction_log());
+
+        assert_eq!(sound.id, sound_id);
+        assert!(transaction_log.contains("file_path"), "{transaction_log}");
+        assert!(transaction_log.contains(media_url), "{transaction_log}");
+    }
+}

src/entity/attachments.rs

@@ -0,0 +1,66 @@
+use sea_orm::entity::prelude::*;
+use serde::{Deserialize, Serialize};
+
+#[derive(Clone, Debug, PartialEq, DeriveEntityModel, Eq, Serialize, Deserialize)]
+#[sea_orm(table_name = "attachments")]
+pub struct Model {
+    #[sea_orm(primary_key, auto_increment = false)]
+    pub id: Uuid,
+    pub channel_message_id: Option<Uuid>,
+    pub direct_message_id: Option<Uuid>,
+    pub uploader_user_id: Uuid,
+    pub object_key: String,
+    pub media_url: String,
+    pub mime_type: String,
+    pub size_bytes: i64,
+    pub original_filename: String,
+    pub created_at: DateTimeWithTimeZone,
+}
+
+#[derive(Copy, Clone, Debug, EnumIter, DeriveRelation)]
+pub enum Relation {
+    #[sea_orm(
+        belongs_to = "super::messages::Entity",
+        from = "Column::ChannelMessageId",
+        to = "super::messages::Column::Id",
+        on_update = "NoAction",
+        on_delete = "Cascade"
+    )]
+    Messages,
+    #[sea_orm(
+        belongs_to = "super::direct_messages::Entity",
+        from = "Column::DirectMessageId",
+        to = "super::direct_messages::Column::Id",
+        on_update = "NoAction",
+        on_delete = "Cascade"
+    )]
+    DirectMessages,
+    #[sea_orm(
+        belongs_to = "super::users::Entity",
+        from = "Column::UploaderUserId",
+        to = "super::users::Column::Id",
+        on_update = "NoAction",
+        on_delete = "NoAction"
+    )]
+    Users,
+}
+
+impl Related<super::messages::Entity> for Entity {
+    fn to() -> RelationDef {
+        Relation::Messages.def()
+    }
+}
+
+impl Related<super::direct_messages::Entity> for Entity {
+    fn to() -> RelationDef {
+        Relation::DirectMessages.def()
+    }
+}
+
+impl Related<super::users::Entity> for Entity {
+    fn to() -> RelationDef {
+        Relation::Users.def()
+    }
+}
+
+impl ActiveModelBehavior for ActiveModel {}

src/entity/mod.rs

@@ -1,8 +1,10 @@
+pub mod attachments;
 pub mod channels;
 pub mod direct_messages;
 pub mod guild_members;
 pub mod guilds;
 pub mod invites;
 pub mod messages;
+pub mod sessions;
 pub mod soundboard_sounds;
 pub mod users;

src/entity/sessions.rs

@@ -0,0 +1,35 @@
+use sea_orm::entity::prelude::*;
+
+#[derive(Clone, Debug, PartialEq, Eq, DeriveEntityModel)]
+#[sea_orm(table_name = "sessions")]
+pub struct Model {
+    #[sea_orm(primary_key, auto_increment = false)]
+    pub id: String,
+    pub user_id: Uuid,
+    pub expires_at: DateTimeWithTimeZone,
+    pub created_at: DateTimeWithTimeZone,
+    pub last_seen_at: DateTimeWithTimeZone,
+    pub revoked_at: Option<DateTimeWithTimeZone>,
+    pub user_agent_hash: Option<String>,
+    pub ip_hash: Option<String>,
+}
+
+#[derive(Copy, Clone, Debug, EnumIter, DeriveRelation)]
+pub enum Relation {
+    #[sea_orm(
+        belongs_to = "super::users::Entity",
+        from = "Column::UserId",
+        to = "super::users::Column::Id",
+        on_update = "NoAction",
+        on_delete = "Cascade"
+    )]
+    Users,
+}
+
+impl Related<super::users::Entity> for Entity {
+    fn to() -> RelationDef {
+        Relation::Users.def()
+    }
+}
+
+impl ActiveModelBehavior for ActiveModel {}

src/entity/soundboard_sounds.rs

@@ -9,7 +9,11 @@ pub struct Model {
     pub guild_id: Uuid,
     pub name: String,
     pub icon: String,
-    pub file_path: String,
+    pub object_key: Option<String>,
+    pub media_url: String,
+    pub mime_type: Option<String>,
+    pub size_bytes: Option<i64>,
+    pub file_path: Option<String>,
     pub created_by_user_id: Uuid,
     pub created_at: DateTimeWithTimeZone,
 }

src/handlers.rs

@@ -1,10 +1,12 @@
 use axum::{
     Json, Router,
-    extract::{Path, Query, State, WebSocketUpgrade},
+    body::Bytes,
+    extract::{DefaultBodyLimit, Path, Query, State, WebSocketUpgrade},
     http::{HeaderMap, StatusCode, header},
     response::{Html, IntoResponse, Redirect},
     routing::{get, post},
 };
+use chrono::Datelike;
 use serde::{Deserialize, Serialize};
 use uuid::Uuid;
 
@@ -12,17 +14,15 @@ use crate::{
     AppState,
     auth::{self, ApiError, AuthUser},
     chat, db,
-    models::{Guild, SoundboardSound},
+    models::{DmMessageWithAuthor, Guild, MessageWithAuthor, SoundboardSound},
     voice,
 };
-use tracing::info;
 
 pub fn routes() -> Router<AppState> {
     Router::new()
         .route("/", get(index))
         .route("/auth/login", get(auth_login))
         .route("/auth/callback", get(auth_callback))
-        .route("/auth/refresh", post(auth_refresh))
         .route("/auth/logout", post(auth_logout))
         .route("/me", get(me))
         .route("/dms", get(list_dm_conversations))
@@ -30,6 +30,11 @@ pub fn routes() -> Router<AppState> {
             "/dms/{other_user_id}/messages",
             get(list_dm_messages).post(send_dm_message),
         )
+        .route(
+            "/dms/{other_user_id}/attachments",
+            post(upload_dm_attachment),
+        )
+        .layer(DefaultBodyLimit::max(MAX_MEDIA_UPLOAD_BYTES))
         .route("/presence", get(presence_list))
         .route("/rtc-config", get(rtc_config))
         .route("/guilds", get(list_guilds).post(create_guild))
@@ -45,6 +50,7 @@ pub fn routes() -> Router<AppState> {
             "/guilds/{guild_id}/sounds",
             get(list_sounds).post(upload_sound),
         )
+        .layer(DefaultBodyLimit::max(MAX_MEDIA_UPLOAD_BYTES))
         .route(
             "/guilds/{guild_id}/sounds/{sound_id}",
             post(delete_sound_post).delete(delete_sound),
@@ -54,6 +60,11 @@ pub fn routes() -> Router<AppState> {
             "/channels/{channel_id}/messages",
             get(list_messages).post(send_message),
         )
+        .route(
+            "/channels/{channel_id}/attachments",
+            post(upload_channel_attachment),
+        )
+        .layer(DefaultBodyLimit::max(MAX_MEDIA_UPLOAD_BYTES))
         .route("/channels/{channel_id}/voice/ws", get(voice_ws))
         .route("/ws", get(chat_ws))
 }
@@ -81,7 +92,7 @@ async fn auth_login(State(state): State<AppState>) -> Result<impl IntoResponse,
     let mut headers = HeaderMap::new();
     headers.insert(
         header::SET_COOKIE,
-        auth::make_oauth_state_cookie(&oauth_state, state.settings.cookie_secure)
+        auth::make_oauth_state_cookie(&oauth_state, state.settings.session_cookie_secure)
             .parse()
             .map_err(|_| ApiError::internal("failed to set oauth cookie"))?,
     );
@@ -147,8 +158,11 @@ async fn auth_callback(
     Query(query): Query<AuthCallbackQuery>,
     headers: HeaderMap,
 ) -> Result<impl IntoResponse, ApiError> {
-    auth::validate_oauth_state(auth::read_oauth_state_from_headers(&headers), &query.state)
+    auth::validate_oauth_state(
-        .map_err(|e| ApiError::bad_request(&e.to_string()))?;
+        auth::read_cookie_from_headers(&headers, auth::OAUTH_STATE_COOKIE),
+        &query.state,
+    )
+    .map_err(|e| ApiError::bad_request(&e.to_string()))?;
 
     let token_res = state
         .http
@@ -214,69 +228,51 @@ async fn auth_callback(
     .await
     .map_err(|e| ApiError::internal(&format!("failed to persist user: {e}")))?;
 
-    let (access_token, refresh_token) =
+    let session_id = auth::new_session_id();
-        auth::new_jwt_tokens(user.id, &state.settings.session_secret)
+    db::create_session(
-            .map_err(|e| ApiError::internal(&e.to_string()))?;
+        &state.db,
+        &session_id,
+        user.id,
+        auth::session_expiry(),
+        auth::user_agent_hash(&headers),
+        auth::ip_hash(&headers),
+    )
+    .await
+    .map_err(|e| ApiError::internal(&format!("failed to create session: {e}")))?;
 
     let mut headers = HeaderMap::new();
     headers.append(
         header::SET_COOKIE,
-        auth::clear_oauth_state_cookie(state.settings.cookie_secure)
+        auth::clear_oauth_state_cookie(state.settings.session_cookie_secure)
             .parse()
             .map_err(|_| ApiError::internal("failed to clear oauth state cookie"))?,
     );
+    headers.append(
+        header::SET_COOKIE,
+        auth::make_session_cookie(&session_id, state.settings.session_cookie_secure)
+            .parse()
+            .map_err(|_| ApiError::internal("failed to set session cookie"))?,
+    );
 
-    Ok((
+    Ok((headers, Redirect::to("/")))
-        headers,
-        Redirect::to(&format!(
-            "/?token={}&refresh_token={}",
-            access_token, refresh_token
-        )),
-    ))
 }
 
-#[derive(Deserialize)]
+async fn auth_logout(
-struct AuthRefreshBody {
-    refresh_token: String,
-}
-
-#[derive(Serialize)]
-struct AuthRefreshResponse {
-    access_token: String,
-    refresh_token: String,
-}
-
-async fn auth_refresh(
     State(state): State<AppState>,
-    Json(body): Json<AuthRefreshBody>,
+    user: AuthUser,
 ) -> Result<impl IntoResponse, ApiError> {
-    let user_id = auth::verify_session(
+    db::revoke_session(&state.db, &user.session_id)
-        &body.refresh_token,
-        &state.settings.session_secret,
-        "refresh",
-    )
-    .map_err(|_| ApiError::unauthorized("invalid or expired refresh token"))?;
-
-    let exists = db::user_exists(&state.db, user_id)
         .await
-        .map_err(|_| ApiError::internal("user verification failed"))?;
+        .map_err(|e| ApiError::internal(&format!("failed to revoke session: {e}")))?;
 
-    if !exists {
+    let mut headers = HeaderMap::new();
-        return Err(ApiError::unauthorized("user not found"));
+    headers.insert(
-    }
+        header::SET_COOKIE,
-
+        auth::clear_session_cookie(state.settings.session_cookie_secure)
-    let (access_token, refresh_token) =
+            .parse()
-        auth::new_jwt_tokens(user_id, &state.settings.session_secret)
+            .map_err(|_| ApiError::internal("failed to clear session cookie"))?,
-            .map_err(|e| ApiError::internal(&e.to_string()))?;
+    );
-
+    Ok((headers, StatusCode::NO_CONTENT))
-    Ok(Json(AuthRefreshResponse {
-        access_token,
-        refresh_token,
-    }))
-}
-
-async fn auth_logout() -> Result<impl IntoResponse, ApiError> {
-    Ok(StatusCode::NO_CONTENT)
 }
 
 #[derive(Serialize)]
@@ -337,9 +333,12 @@ async fn me(State(state): State<AppState>, user: AuthUser) -> Result<impl IntoRe
 
 async fn presence_list(
     State(state): State<AppState>,
-    _user: AuthUser,
+    user: AuthUser,
 ) -> Result<impl IntoResponse, ApiError> {
-    let users = state.chat.get_online_users().await;
+    let visible_user_ids = db::list_visible_user_ids(&state.db, user.id)
+        .await
+        .map_err(|e| ApiError::internal(&format!("failed to load visible users: {e}")))?;
+    let users = state.chat.get_online_users_for(&visible_user_ids).await;
     Ok(Json(users))
 }
 
@@ -680,11 +679,101 @@ async fn send_dm_message(
     Ok((StatusCode::CREATED, Json(SendMessageResponse { ok: true })))
 }
 
-async fn voice_ws(
+async fn upload_channel_attachment(
-    ws: WebSocketUpgrade,
     State(state): State<AppState>,
     user: AuthUser,
     Path(channel_id): Path<Uuid>,
+    headers: HeaderMap,
+    body: Bytes,
+) -> Result<impl IntoResponse, ApiError> {
+    ensure_channel_member(&state, channel_id, user.id).await?;
+    let uploaded = upload_media_from_request(
+        &state,
+        &headers,
+        body,
+        channel_object_key_prefix(channel_id),
+    )
+    .await?;
+
+    let message = db::create_message_with_attachment(
+        &state.db,
+        channel_id,
+        user.id,
+        "",
+        &uploaded.object_key,
+        &uploaded.media_url,
+        &uploaded.mime_type,
+        uploaded.size_bytes,
+        &uploaded.original_filename,
+    )
+    .await
+    .map_err(|e| ApiError::internal(&format!("failed to create message attachment: {e}")))?;
+
+    let guild_id = db::guild_id_for_channel(&state.db, channel_id)
+        .await
+        .map_err(|e| ApiError::internal(&format!("channel lookup failed: {e}")))?
+        .ok_or_else(|| ApiError::internal("channel not found after attachment upload"))?;
+
+    let members = db::list_guild_member_ids(&state.db, guild_id)
+        .await
+        .map_err(|e| ApiError::internal(&format!("failed to list guild members: {e}")))?;
+
+    broadcast_channel_message(&state, members, channel_id, &message).await;
+    Ok((StatusCode::CREATED, Json(message)))
+}
+
+async fn upload_dm_attachment(
+    State(state): State<AppState>,
+    user: AuthUser,
+    Path(other_user_id): Path<Uuid>,
+    headers: HeaderMap,
+    body: Bytes,
+) -> Result<impl IntoResponse, ApiError> {
+    if other_user_id == user.id {
+        return Err(ApiError::bad_request("cannot send dm to yourself"));
+    }
+
+    let other_user_exists = db::user_exists(&state.db, other_user_id)
+        .await
+        .map_err(|e| ApiError::internal(&format!("user check failed: {e}")))?;
+    if !other_user_exists {
+        return Err(ApiError {
+            status: StatusCode::NOT_FOUND,
+            message: "user not found".to_string(),
+        });
+    }
+
+    let uploaded = upload_media_from_request(
+        &state,
+        &headers,
+        body,
+        dm_object_key_prefix(user.id, other_user_id),
+    )
+    .await?;
+
+    let message = db::create_direct_message_with_attachment(
+        &state.db,
+        user.id,
+        other_user_id,
+        "",
+        &uploaded.object_key,
+        &uploaded.media_url,
+        &uploaded.mime_type,
+        uploaded.size_bytes,
+        &uploaded.original_filename,
+    )
+    .await
+    .map_err(|e| ApiError::internal(&format!("failed to create dm attachment: {e}")))?;
+
+    broadcast_dm_message(&state, user.id, other_user_id, &message).await;
+    Ok((StatusCode::CREATED, Json(message)))
+}
+
+async fn voice_ws(
+    State(state): State<AppState>,
+    user: AuthUser,
+    Path(channel_id): Path<Uuid>,
+    ws: WebSocketUpgrade,
 ) -> Result<impl IntoResponse, ApiError> {
     ensure_channel_member(&state, channel_id, user.id).await?;
 
@@ -706,9 +795,9 @@ async fn voice_ws(
 }
 
 async fn chat_ws(
-    ws: WebSocketUpgrade,
     State(state): State<AppState>,
     user: AuthUser,
+    ws: WebSocketUpgrade,
 ) -> Result<impl IntoResponse, ApiError> {
     Ok(ws.on_upgrade(move |socket| chat::handle_socket(state, socket, user.id)))
 }
@@ -772,28 +861,348 @@ async fn upload_sound(
         _ => return Err(ApiError::bad_request("missing fields")),
     };
 
-    let extension = std::path::Path::new(&file_name)
+    let validated = validate_sound_upload(&file_name, &file_data)
-        .extension()
+        .map_err(|e| ApiError::bad_request(&e.to_string()))?;
-        .and_then(|e| e.to_str())
-        .unwrap_or("mp3");
 
-    let safe_file_name = format!("{}.{}", Uuid::new_v4(), extension);
+    let storage = state
-    let upload_dir = std::path::Path::new("static/uploads/soundboard");
+        .media
-    tokio::fs::create_dir_all(upload_dir)
+        .as_ref()
+        .ok_or_else(|| ApiError::service_unavailable("media storage is not configured"))?;
+
+    let object_key = format!(
+        "soundboard/{guild_id}/{}-{}",
+        Uuid::new_v4(),
+        sanitize_file_name(&file_name)
+    );
+    let media_url = storage
+        .upload_object(
+            &object_key,
+            file_data.to_vec(),
+            &validated.mime_type,
+            &file_name,
+            false,
+        )
         .await
         .map_err(|e| ApiError::internal(&e.to_string()))?;
 
-    let file_path = upload_dir.join(&safe_file_name);
+    let sound = db::create_sound(
-    tokio::fs::write(&file_path, file_data)
+        &state.db,
-        .await
+        guild_id,
-        .map_err(|e| ApiError::internal(&e.to_string()))?;
+        user.id,
-
+        name.trim(),
-    let web_path = format!("/static/uploads/soundboard/{}", safe_file_name);
+        icon.trim(),
-
+        &object_key,
-    let sound = db::create_sound(&state.db, guild_id, user.id, &name, &icon, &web_path).await?;
+        &media_url,
+        &validated.mime_type,
+        validated.size_bytes,
+    )
+    .await?;
     Ok(Json(sound))
 }
 
+const MAX_MEDIA_UPLOAD_BYTES: usize = 50 * 1024 * 1024;
+
+struct UploadedMedia {
+    object_key: String,
+    media_url: String,
+    mime_type: String,
+    size_bytes: i64,
+    original_filename: String,
+}
+
+#[derive(Debug)]
+struct ValidatedUpload {
+    mime_type: String,
+    inline: bool,
+    size_bytes: i64,
+}
+
+async fn upload_media_from_request(
+    state: &AppState,
+    headers: &HeaderMap,
+    body: Bytes,
+    object_key_prefix: String,
+) -> Result<UploadedMedia, ApiError> {
+    let storage = state
+        .media
+        .as_ref()
+        .ok_or_else(|| ApiError::service_unavailable("media storage is not configured"))?;
+
+    let original_filename = headers
+        .get("x-file-name")
+        .and_then(|v| v.to_str().ok())
+        .map(str::trim)
+        .filter(|v| !v.is_empty())
+        .map(ToString::to_string)
+        .ok_or_else(|| ApiError::bad_request("missing x-file-name header"))?;
+
+    let raw_mime_type = headers
+        .get(header::CONTENT_TYPE)
+        .and_then(|v| v.to_str().ok())
+        .map(str::trim)
+        .filter(|v| !v.is_empty())
+        .unwrap_or("application/octet-stream")
+        .to_string();
+
+    if body.is_empty() {
+        return Err(ApiError::bad_request("missing file upload"));
+    }
+    if body.len() > MAX_MEDIA_UPLOAD_BYTES {
+        return Err(ApiError::bad_request("file exceeds 50MB upload limit"));
+    }
+
+    let validated = validate_general_upload(&original_filename, &body, &raw_mime_type)
+        .map_err(|e| ApiError::bad_request(&e.to_string()))?;
+    let safe_name = sanitize_file_name(&original_filename);
+    let object_key = format!("{}/{}-{}", object_key_prefix, Uuid::new_v4(), safe_name);
+    let size_bytes = body.len() as i64;
+    let media_url = storage
+        .upload_object(
+            &object_key,
+            body.to_vec(),
+            &validated.mime_type,
+            &original_filename,
+            validated.inline,
+        )
+        .await
+        .map_err(|e| ApiError::internal(&e.to_string()))?;
+
+    Ok(UploadedMedia {
+        object_key,
+        media_url,
+        mime_type: validated.mime_type,
+        size_bytes,
+        original_filename,
+    })
+}
+
+async fn broadcast_channel_message(
+    state: &AppState,
+    members: Vec<Uuid>,
+    channel_id: Uuid,
+    message: &MessageWithAuthor,
+) {
+    state
+        .chat
+        .broadcast_to_many(
+            members,
+            chat::ServerEvent::MessageCreated {
+                channel_id,
+                message: serde_json::to_value(message).unwrap_or_default(),
+            },
+        )
+        .await;
+}
+
+async fn broadcast_dm_message(
+    state: &AppState,
+    current_user_id: Uuid,
+    other_user_id: Uuid,
+    message: &DmMessageWithAuthor,
+) {
+    state
+        .chat
+        .broadcast_to_user(
+            current_user_id,
+            chat::ServerEvent::DmCreated {
+                other_user_id,
+                message: serde_json::to_value(message).unwrap_or_default(),
+            },
+        )
+        .await;
+    state
+        .chat
+        .broadcast_to_user(
+            other_user_id,
+            chat::ServerEvent::DmCreated {
+                other_user_id: current_user_id,
+                message: serde_json::to_value(message).unwrap_or_default(),
+            },
+        )
+        .await;
+}
+
+fn sanitize_file_name(file_name: &str) -> String {
+    let sanitized: String = file_name
+        .chars()
+        .map(|ch| {
+            if ch.is_ascii_alphanumeric() || matches!(ch, '.' | '-' | '_') {
+                ch
+            } else {
+                '_'
+            }
+        })
+        .collect();
+
+    let trimmed = sanitized.trim_matches(|ch| ch == '_' || ch == '.').trim();
+    if trimmed.is_empty() {
+        "upload.bin".to_string()
+    } else {
+        trimmed.to_string()
+    }
+}
+
+fn validate_general_upload(
+    file_name: &str,
+    bytes: &[u8],
+    claimed_mime: &str,
+) -> anyhow::Result<ValidatedUpload> {
+    let extension = lower_file_extension(file_name)
+        .ok_or_else(|| anyhow::anyhow!("file extension is required"))?;
+    let normalized_mime = sniff_upload_type(bytes, &extension, claimed_mime)
+        .ok_or_else(|| anyhow::anyhow!("unsupported upload type"))?;
+    let inline = is_inline_media_type(&normalized_mime);
+
+    Ok(ValidatedUpload {
+        mime_type: normalized_mime,
+        inline,
+        size_bytes: bytes.len() as i64,
+    })
+}
+
+fn validate_sound_upload(file_name: &str, bytes: &[u8]) -> anyhow::Result<ValidatedUpload> {
+    let extension = lower_file_extension(file_name)
+        .ok_or_else(|| anyhow::anyhow!("sound file extension is required"))?;
+    let Some(mime_type) = sniff_audio_type(bytes, &extension) else {
+        return Err(anyhow::anyhow!(
+            "only mp3, ogg, and wav sounds are supported"
+        ));
+    };
+
+    Ok(ValidatedUpload {
+        mime_type,
+        inline: false,
+        size_bytes: bytes.len() as i64,
+    })
+}
+
+fn lower_file_extension(file_name: &str) -> Option<String> {
+    std::path::Path::new(file_name)
+        .extension()
+        .and_then(|ext| ext.to_str())
+        .map(|ext| ext.to_ascii_lowercase())
+}
+
+fn sniff_upload_type(bytes: &[u8], extension: &str, claimed_mime: &str) -> Option<String> {
+    sniff_audio_type(bytes, extension)
+        .or_else(|| sniff_image_type(bytes, extension))
+        .or_else(|| sniff_video_type(bytes, extension))
+        .or_else(|| sniff_document_type(extension, claimed_mime))
+}
+
+fn sniff_audio_type(bytes: &[u8], extension: &str) -> Option<String> {
+    match extension {
+        "mp3" if bytes.starts_with(b"ID3") || bytes.first().copied() == Some(0xff) => {
+            Some("audio/mpeg".to_string())
+        }
+        "ogg" if bytes.starts_with(b"OggS") => Some("audio/ogg".to_string()),
+        "wav" if bytes.starts_with(b"RIFF") && bytes.get(8..12) == Some(b"WAVE") => {
+            Some("audio/wav".to_string())
+        }
+        _ => None,
+    }
+}
+
+fn sniff_image_type(bytes: &[u8], extension: &str) -> Option<String> {
+    match extension {
+        "png" if bytes.starts_with(b"\x89PNG\r\n\x1a\n") => Some("image/png".to_string()),
+        "jpg" | "jpeg" if bytes.starts_with(&[0xff, 0xd8, 0xff]) => Some("image/jpeg".to_string()),
+        "gif" if bytes.starts_with(b"GIF87a") || bytes.starts_with(b"GIF89a") => {
+            Some("image/gif".to_string())
+        }
+        "webp" if bytes.starts_with(b"RIFF") && bytes.get(8..12) == Some(b"WEBP") => {
+            Some("image/webp".to_string())
+        }
+        _ => None,
+    }
+}
+
+fn sniff_video_type(bytes: &[u8], extension: &str) -> Option<String> {
+    match extension {
+        "mp4"
+            if bytes
+                .windows(8)
+                .any(|window| window == b"ftypisom" || window == b"ftypmp42") =>
+        {
+            Some("video/mp4".to_string())
+        }
+        "webm" if bytes.starts_with(&[0x1a, 0x45, 0xdf, 0xa3]) => Some("video/webm".to_string()),
+        _ => None,
+    }
+}
+
+fn sniff_document_type(extension: &str, claimed_mime: &str) -> Option<String> {
+    match extension {
+        "pdf" => Some("application/pdf".to_string()),
+        "txt" => Some("text/plain".to_string()),
+        "json" => Some("application/json".to_string()),
+        "csv" => Some("text/csv".to_string()),
+        "md" => Some("text/markdown".to_string()),
+        "zip" => Some("application/zip".to_string()),
+        "gz" => Some("application/gzip".to_string()),
+        _ if matches!(
+            claimed_mime,
+            "application/pdf"
+                | "text/plain"
+                | "application/json"
+                | "text/csv"
+                | "text/markdown"
+                | "application/zip"
+                | "application/gzip"
+        ) =>
+        {
+            Some(claimed_mime.to_string())
+        }
+        _ => None,
+    }
+}
+
+fn is_inline_media_type(mime_type: &str) -> bool {
+    matches!(
+        mime_type,
+        "image/png"
+            | "image/jpeg"
+            | "image/gif"
+            | "image/webp"
+            | "video/mp4"
+            | "video/webm"
+            | "audio/mpeg"
+            | "audio/ogg"
+            | "audio/wav"
+            | "application/pdf"
+            | "text/plain"
+            | "application/json"
+            | "text/csv"
+            | "text/markdown"
+    )
+}
+
+fn channel_object_key_prefix(channel_id: Uuid) -> String {
+    let now = chrono::Utc::now();
+    format!(
+        "channels/{}/{:04}/{:02}",
+        channel_id,
+        now.year(),
+        now.month()
+    )
+}
+
+fn dm_object_key_prefix(user_a: Uuid, user_b: Uuid) -> String {
+    let now = chrono::Utc::now();
+    let (left, right) = if user_a <= user_b {
+        (user_a, user_b)
+    } else {
+        (user_b, user_a)
+    };
+    format!(
+        "dms/{}-{}/{:04}/{:02}",
+        left,
+        right,
+        now.year(),
+        now.month()
+    )
+}
+
 async fn delete_sound_post(
     state: State<AppState>,
     user: AuthUser,
@@ -832,10 +1241,15 @@ async fn delete_sound(
         });
     }
 
-    // Delete file from disk
+    let object_key = db::get_sound_object_key(&state.db, sound_id)
-    let relative_path = sound.file_path.trim_start_matches('/');
+        .await
-    if let Err(e) = tokio::fs::remove_file(relative_path).await {
+        .map_err(|e| ApiError::internal(&format!("failed to load sound storage key: {e}")))?;
-        info!("failed to delete sound file {}: {}", relative_path, e);
+
+    if let (Some(storage), Some(object_key)) = (state.media.as_ref(), object_key.as_deref()) {
+        storage
+            .delete_object(object_key)
+            .await
+            .map_err(|e| ApiError::internal(&format!("failed to delete sound media: {e}")))?;
     }
 
     db::delete_sound(&state.db, sound_id)
@@ -879,3 +1293,100 @@ async fn ensure_channel_member(
 
     ensure_guild_member(state, guild_id, user_id).await
 }
+
+#[cfg(test)]
+mod tests {
+    use super::{
+        sanitize_file_name, upload_media_from_request, validate_general_upload,
+        validate_sound_upload,
+    };
+    use crate::{AppState, chat::ChatHub, config::Settings, voice::VoiceHub};
+    use axum::{
+        body::Bytes,
+        http::{HeaderMap, StatusCode, header},
+    };
+    use sea_orm::{DatabaseBackend, MockDatabase};
+    use std::sync::Arc;
+
+    fn test_state() -> AppState {
+        AppState {
+            db: Arc::new(MockDatabase::new(DatabaseBackend::Postgres).into_connection()),
+            settings: Arc::new(Settings {
+                port: 3000,
+                app_base_url: "http://localhost:3000".to_string(),
+                app_origin: "http://localhost:3000".to_string(),
+                database_url: "postgres://localhost/test".to_string(),
+                oidc_client_id: "client".to_string(),
+                oidc_client_secret: "secret".to_string(),
+                oidc_authorize_url: "http://localhost:3000/oidc/authorize".to_string(),
+                oidc_token_url: "http://localhost:3000/oidc/token".to_string(),
+                oidc_userinfo_url: "http://localhost:3000/oidc/userinfo".to_string(),
+                oidc_redirect_url: "http://localhost:3000/auth/callback".to_string(),
+                oidc_scopes: "openid profile email".to_string(),
+                session_cookie_secure: false,
+                stun_urls: vec!["stun:stun.l.google.com:19302".to_string()],
+                turn_urls: Vec::new(),
+                turn_username: None,
+                turn_password: None,
+                media: None,
+            }),
+            http: reqwest::Client::new(),
+            voice: Arc::new(VoiceHub::default()),
+            chat: Arc::new(ChatHub::default()),
+            media: None,
+        }
+    }
+
+    #[test]
+    fn sanitize_file_name_replaces_unsafe_chars() {
+        assert_eq!(
+            sanitize_file_name("../../hello world?.mp3"),
+            "hello_world_.mp3"
+        );
+    }
+
+    #[test]
+    fn validates_png_uploads() {
+        let png = b"\x89PNG\r\n\x1a\nrest";
+        let upload = validate_general_upload("image.png", png, "image/png").unwrap();
+        assert_eq!(upload.mime_type, "image/png");
+        assert!(upload.inline);
+    }
+
+    #[test]
+    fn rejects_unknown_uploads() {
+        let err = validate_general_upload("payload.exe", b"MZ...", "application/octet-stream")
+            .unwrap_err();
+        assert!(err.to_string().contains("unsupported upload type"));
+    }
+
+    #[test]
+    fn validates_sound_uploads() {
+        let wav = b"RIFFdataWAVE";
+        let upload = validate_sound_upload("sound.wav", wav).unwrap();
+        assert_eq!(upload.mime_type, "audio/wav");
+    }
+
+    #[tokio::test]
+    async fn upload_helper_requires_configured_media_storage() {
+        let state = test_state();
+        let mut headers = HeaderMap::new();
+        headers.insert("x-file-name", "photo.png".parse().unwrap());
+        headers.insert(header::CONTENT_TYPE, "image/png".parse().unwrap());
+
+        let err = match upload_media_from_request(
+            &state,
+            &headers,
+            Bytes::from_static(b"\x89PNG\r\n\x1a\nrest"),
+            "channels/test".to_string(),
+        )
+        .await
+        {
+            Ok(_) => panic!("expected upload helper to reject missing media storage"),
+            Err(err) => err,
+        };
+
+        assert_eq!(err.status, StatusCode::SERVICE_UNAVAILABLE);
+        assert_eq!(err.message, "media storage is not configured");
+    }
+}

src/media.rs

@@ -0,0 +1,87 @@
+use anyhow::{Result, anyhow};
+use aws_config::BehaviorVersion;
+use aws_sdk_s3::{
+    Client,
+    config::{Credentials, Region},
+    primitives::ByteStream,
+};
+
+use crate::config::MediaSettings;
+
+#[derive(Clone)]
+pub struct MediaStorage {
+    client: Client,
+    bucket: String,
+    public_base_url: String,
+}
+
+impl MediaStorage {
+    pub async fn new(settings: &MediaSettings) -> Result<Self> {
+        let shared_config = aws_config::defaults(BehaviorVersion::latest())
+            .region(Region::new("auto"))
+            .credentials_provider(Credentials::new(
+                settings.access_key_id.clone(),
+                settings.secret_access_key.clone(),
+                None,
+                None,
+                "chattz-r2",
+            ))
+            .load()
+            .await;
+
+        let config = aws_sdk_s3::config::Builder::from(&shared_config)
+            .endpoint_url(settings.endpoint_url())
+            .force_path_style(true)
+            .build();
+
+        Ok(Self {
+            client: Client::from_conf(config),
+            bucket: settings.bucket.clone(),
+            public_base_url: settings.public_base_url.trim_end_matches('/').to_string(),
+        })
+    }
+
+    pub async fn upload_object(
+        &self,
+        object_key: &str,
+        bytes: Vec<u8>,
+        content_type: &str,
+        original_filename: &str,
+        inline: bool,
+    ) -> Result<String> {
+        self.client
+            .put_object()
+            .bucket(&self.bucket)
+            .key(object_key)
+            .body(ByteStream::from(bytes))
+            .content_type(content_type)
+            .content_disposition(format!(
+                "{}; filename=\"{}\"",
+                if inline { "inline" } else { "attachment" },
+                sanitize_header_value(original_filename)
+            ))
+            .send()
+            .await
+            .map_err(|e| anyhow!("failed to upload object to R2: {e}"))?;
+
+        Ok(format!("{}/{}", self.public_base_url, object_key))
+    }
+
+    pub async fn delete_object(&self, object_key: &str) -> Result<()> {
+        self.client
+            .delete_object()
+            .bucket(&self.bucket)
+            .key(object_key)
+            .send()
+            .await
+            .map_err(|e| anyhow!("failed to delete object from R2: {e}"))?;
+        Ok(())
+    }
+}
+
+fn sanitize_header_value(value: &str) -> String {
+    value
+        .chars()
+        .filter(|c| *c != '\\' && *c != '"' && !c.is_control())
+        .collect()
+}

src/migration/m20260213_000001_init.rs

@@ -11,13 +11,13 @@ impl MigrationTrait for Migration {
                 Table::create()
                     .table(Users::Table)
                     .if_not_exists()
+                    .col(ColumnDef::new(Users::Id).uuid().not_null().primary_key())
                     .col(
-                        ColumnDef::new(Users::Id)
+                        ColumnDef::new(Users::OidcSub)
-                            .uuid()
+                            .string()
                             .not_null()
-                            .primary_key(),
+                            .unique_key(),
                     )
-                    .col(ColumnDef::new(Users::OidcSub).string().not_null().unique_key())
                     .col(ColumnDef::new(Users::Email).string())
                     .col(ColumnDef::new(Users::DisplayName).string().not_null())
                     .col(ColumnDef::new(Users::AvatarUrl).string())
@@ -42,12 +42,7 @@ impl MigrationTrait for Migration {
                 Table::create()
                     .table(Guilds::Table)
                     .if_not_exists()
-                    .col(
+                    .col(ColumnDef::new(Guilds::Id).uuid().not_null().primary_key())
-                        ColumnDef::new(Guilds::Id)
-                            .uuid()
-                            .not_null()
-                            .primary_key(),
-                    )
                     .col(ColumnDef::new(Guilds::Name).string().not_null())
                     .col(ColumnDef::new(Guilds::OwnerUserId).uuid().not_null())
                     .col(
@@ -108,12 +103,7 @@ impl MigrationTrait for Migration {
                 Table::create()
                     .table(Channels::Table)
                     .if_not_exists()
-                    .col(
+                    .col(ColumnDef::new(Channels::Id).uuid().not_null().primary_key())
-                        ColumnDef::new(Channels::Id)
-                            .uuid()
-                            .not_null()
-                            .primary_key(),
-                    )
                     .col(ColumnDef::new(Channels::GuildId).uuid().not_null())
                     .col(ColumnDef::new(Channels::Name).string().not_null())
                     .col(
@@ -138,12 +128,7 @@ impl MigrationTrait for Migration {
                 Table::create()
                     .table(Messages::Table)
                     .if_not_exists()
-                    .col(
+                    .col(ColumnDef::new(Messages::Id).uuid().not_null().primary_key())
-                        ColumnDef::new(Messages::Id)
-                            .uuid()
-                            .not_null()
-                            .primary_key(),
-                    )
                     .col(ColumnDef::new(Messages::ChannelId).uuid().not_null())
                     .col(ColumnDef::new(Messages::AuthorUserId).uuid().not_null())
                     .col(ColumnDef::new(Messages::Body).text().not_null())

src/migration/m20260213_000002_invites.rs

@@ -11,7 +11,12 @@ impl MigrationTrait for Migration {
                 Table::create()
                     .table(Invites::Table)
                     .if_not_exists()
-                    .col(ColumnDef::new(Invites::Code).string().not_null().primary_key())
+                    .col(
+                        ColumnDef::new(Invites::Code)
+                            .string()
+                            .not_null()
+                            .primary_key(),
+                    )
                     .col(ColumnDef::new(Invites::GuildId).uuid().not_null())
                     .col(ColumnDef::new(Invites::CreatedByUserId).uuid().not_null())
                     .col(

src/migration/m20260213_000004_direct_messages.rs

@@ -17,8 +17,16 @@ impl MigrationTrait for Migration {
                             .not_null()
                             .primary_key(),
                     )
-                    .col(ColumnDef::new(DirectMessages::SenderUserId).uuid().not_null())
+                    .col(
-                    .col(ColumnDef::new(DirectMessages::RecipientUserId).uuid().not_null())
+                        ColumnDef::new(DirectMessages::SenderUserId)
+                            .uuid()
+                            .not_null(),
+                    )
+                    .col(
+                        ColumnDef::new(DirectMessages::RecipientUserId)
+                            .uuid()
+                            .not_null(),
+                    )
                     .col(ColumnDef::new(DirectMessages::Body).text().not_null())
                     .col(
                         ColumnDef::new(DirectMessages::CreatedAt)

src/migration/m20260227_000006_attachments.rs

@@ -0,0 +1,122 @@
+use sea_orm_migration::prelude::*;
+
+#[derive(DeriveMigrationName)]
+pub struct Migration;
+
+#[async_trait::async_trait]
+impl MigrationTrait for Migration {
+    async fn up(&self, manager: &SchemaManager) -> Result<(), DbErr> {
+        manager
+            .create_table(
+                Table::create()
+                    .table(Attachments::Table)
+                    .if_not_exists()
+                    .col(
+                        ColumnDef::new(Attachments::Id)
+                            .uuid()
+                            .not_null()
+                            .primary_key(),
+                    )
+                    .col(ColumnDef::new(Attachments::ChannelMessageId).uuid().null())
+                    .col(ColumnDef::new(Attachments::DirectMessageId).uuid().null())
+                    .col(ColumnDef::new(Attachments::UploaderUserId).uuid().not_null())
+                    .col(ColumnDef::new(Attachments::ObjectKey).string().not_null())
+                    .col(ColumnDef::new(Attachments::MediaUrl).string().not_null())
+                    .col(ColumnDef::new(Attachments::MimeType).string().not_null())
+                    .col(ColumnDef::new(Attachments::SizeBytes).big_integer().not_null())
+                    .col(ColumnDef::new(Attachments::OriginalFilename).string().not_null())
+                    .col(
+                        ColumnDef::new(Attachments::CreatedAt)
+                            .timestamp_with_time_zone()
+                            .not_null()
+                            .default(Expr::current_timestamp()),
+                    )
+                    .foreign_key(
+                        ForeignKey::create()
+                            .name("fk_attachments_channel_message")
+                            .from(Attachments::Table, Attachments::ChannelMessageId)
+                            .to(Messages::Table, Messages::Id)
+                            .on_delete(ForeignKeyAction::Cascade),
+                    )
+                    .foreign_key(
+                        ForeignKey::create()
+                            .name("fk_attachments_direct_message")
+                            .from(Attachments::Table, Attachments::DirectMessageId)
+                            .to(DirectMessages::Table, DirectMessages::Id)
+                            .on_delete(ForeignKeyAction::Cascade),
+                    )
+                    .foreign_key(
+                        ForeignKey::create()
+                            .name("fk_attachments_uploader")
+                            .from(Attachments::Table, Attachments::UploaderUserId)
+                            .to(Users::Table, Users::Id),
+                    )
+                    .check(
+                        Expr::cust(
+                            "(channel_message_id IS NOT NULL AND direct_message_id IS NULL) OR (channel_message_id IS NULL AND direct_message_id IS NOT NULL)",
+                        ),
+                    )
+                    .to_owned(),
+            )
+            .await?;
+
+        manager
+            .create_index(
+                Index::create()
+                    .name("idx_attachments_channel_message")
+                    .table(Attachments::Table)
+                    .col(Attachments::ChannelMessageId)
+                    .to_owned(),
+            )
+            .await?;
+
+        manager
+            .create_index(
+                Index::create()
+                    .name("idx_attachments_direct_message")
+                    .table(Attachments::Table)
+                    .col(Attachments::DirectMessageId)
+                    .to_owned(),
+            )
+            .await
+    }
+
+    async fn down(&self, manager: &SchemaManager) -> Result<(), DbErr> {
+        manager
+            .drop_table(Table::drop().table(Attachments::Table).to_owned())
+            .await
+    }
+}
+
+#[derive(DeriveIden)]
+enum Attachments {
+    Table,
+    Id,
+    ChannelMessageId,
+    DirectMessageId,
+    UploaderUserId,
+    ObjectKey,
+    MediaUrl,
+    MimeType,
+    SizeBytes,
+    OriginalFilename,
+    CreatedAt,
+}
+
+#[derive(DeriveIden)]
+enum Messages {
+    Table,
+    Id,
+}
+
+#[derive(DeriveIden)]
+enum DirectMessages {
+    Table,
+    Id,
+}
+
+#[derive(DeriveIden)]
+enum Users {
+    Table,
+    Id,
+}

src/migration/m20260227_000007_sessions.rs

@@ -0,0 +1,107 @@
+use sea_orm_migration::prelude::*;
+
+#[derive(DeriveMigrationName)]
+pub struct Migration;
+
+#[async_trait::async_trait]
+impl MigrationTrait for Migration {
+    async fn up(&self, manager: &SchemaManager) -> Result<(), DbErr> {
+        manager
+            .create_table(
+                Table::create()
+                    .table(Sessions::Table)
+                    .if_not_exists()
+                    .col(
+                        ColumnDef::new(Sessions::Id)
+                            .string()
+                            .not_null()
+                            .primary_key(),
+                    )
+                    .col(ColumnDef::new(Sessions::UserId).uuid().not_null())
+                    .col(
+                        ColumnDef::new(Sessions::ExpiresAt)
+                            .timestamp_with_time_zone()
+                            .not_null(),
+                    )
+                    .col(
+                        ColumnDef::new(Sessions::CreatedAt)
+                            .timestamp_with_time_zone()
+                            .not_null()
+                            .default(Expr::current_timestamp()),
+                    )
+                    .col(
+                        ColumnDef::new(Sessions::LastSeenAt)
+                            .timestamp_with_time_zone()
+                            .not_null()
+                            .default(Expr::current_timestamp()),
+                    )
+                    .col(ColumnDef::new(Sessions::RevokedAt).timestamp_with_time_zone())
+                    .col(ColumnDef::new(Sessions::UserAgentHash).string())
+                    .col(ColumnDef::new(Sessions::IpHash).string())
+                    .foreign_key(
+                        ForeignKey::create()
+                            .name("fk_sessions_user")
+                            .from(Sessions::Table, Sessions::UserId)
+                            .to(Users::Table, Users::Id)
+                            .on_delete(ForeignKeyAction::Cascade),
+                    )
+                    .to_owned(),
+            )
+            .await?;
+
+        manager
+            .create_index(
+                Index::create()
+                    .name("idx_sessions_user_id")
+                    .table(Sessions::Table)
+                    .col(Sessions::UserId)
+                    .to_owned(),
+            )
+            .await?;
+
+        manager
+            .create_index(
+                Index::create()
+                    .name("idx_sessions_expires_at")
+                    .table(Sessions::Table)
+                    .col(Sessions::ExpiresAt)
+                    .to_owned(),
+            )
+            .await?;
+
+        manager
+            .create_index(
+                Index::create()
+                    .name("idx_sessions_revoked_at")
+                    .table(Sessions::Table)
+                    .col(Sessions::RevokedAt)
+                    .to_owned(),
+            )
+            .await
+    }
+
+    async fn down(&self, manager: &SchemaManager) -> Result<(), DbErr> {
+        manager
+            .drop_table(Table::drop().table(Sessions::Table).to_owned())
+            .await
+    }
+}
+
+#[derive(DeriveIden)]
+enum Sessions {
+    Table,
+    Id,
+    UserId,
+    ExpiresAt,
+    CreatedAt,
+    LastSeenAt,
+    RevokedAt,
+    UserAgentHash,
+    IpHash,
+}
+
+#[derive(DeriveIden)]
+enum Users {
+    Table,
+    Id,
+}

src/migration/m20260227_000008_soundboard_media.rs

@@ -0,0 +1,72 @@
+use sea_orm_migration::prelude::*;
+
+#[derive(DeriveMigrationName)]
+pub struct Migration;
+
+#[async_trait::async_trait]
+impl MigrationTrait for Migration {
+    async fn up(&self, manager: &SchemaManager) -> Result<(), DbErr> {
+        manager
+            .alter_table(
+                Table::alter()
+                    .table(SoundboardSounds::Table)
+                    .add_column(ColumnDef::new(SoundboardSounds::ObjectKey).string().null())
+                    .add_column(ColumnDef::new(SoundboardSounds::MediaUrl).string().null())
+                    .add_column(ColumnDef::new(SoundboardSounds::MimeType).string().null())
+                    .add_column(
+                        ColumnDef::new(SoundboardSounds::SizeBytes)
+                            .big_integer()
+                            .null(),
+                    )
+                    .to_owned(),
+            )
+            .await?;
+
+        manager
+            .get_connection()
+            .execute_unprepared(
+                r#"
+                UPDATE soundboard_sounds
+                SET media_url = file_path
+                WHERE media_url IS NULL
+                "#,
+            )
+            .await?;
+
+        manager
+            .alter_table(
+                Table::alter()
+                    .table(SoundboardSounds::Table)
+                    .modify_column(
+                        ColumnDef::new(SoundboardSounds::MediaUrl)
+                            .string()
+                            .not_null(),
+                    )
+                    .to_owned(),
+            )
+            .await
+    }
+
+    async fn down(&self, manager: &SchemaManager) -> Result<(), DbErr> {
+        manager
+            .alter_table(
+                Table::alter()
+                    .table(SoundboardSounds::Table)
+                    .drop_column(SoundboardSounds::ObjectKey)
+                    .drop_column(SoundboardSounds::MediaUrl)
+                    .drop_column(SoundboardSounds::MimeType)
+                    .drop_column(SoundboardSounds::SizeBytes)
+                    .to_owned(),
+            )
+            .await
+    }
+}
+
+#[derive(DeriveIden)]
+enum SoundboardSounds {
+    Table,
+    ObjectKey,
+    MediaUrl,
+    MimeType,
+    SizeBytes,
+}

src/migration/m20260227_000009_soundboard_file_path_nullable.rs

@@ -0,0 +1,50 @@
+use sea_orm_migration::prelude::*;
+
+#[derive(DeriveMigrationName)]
+pub struct Migration;
+
+#[async_trait::async_trait]
+impl MigrationTrait for Migration {
+    async fn up(&self, manager: &SchemaManager) -> Result<(), DbErr> {
+        manager
+            .alter_table(
+                Table::alter()
+                    .table(SoundboardSounds::Table)
+                    .modify_column(ColumnDef::new(SoundboardSounds::FilePath).string().null())
+                    .to_owned(),
+            )
+            .await
+    }
+
+    async fn down(&self, manager: &SchemaManager) -> Result<(), DbErr> {
+        manager
+            .get_connection()
+            .execute_unprepared(
+                r#"
+                UPDATE soundboard_sounds
+                SET file_path = media_url
+                WHERE file_path IS NULL
+                "#,
+            )
+            .await?;
+
+        manager
+            .alter_table(
+                Table::alter()
+                    .table(SoundboardSounds::Table)
+                    .modify_column(
+                        ColumnDef::new(SoundboardSounds::FilePath)
+                            .string()
+                            .not_null(),
+                    )
+                    .to_owned(),
+            )
+            .await
+    }
+}
+
+#[derive(DeriveIden)]
+enum SoundboardSounds {
+    Table,
+    FilePath,
+}

src/migration/mod.rs

@@ -5,6 +5,10 @@ mod m20260213_000002_invites;
 mod m20260213_000003_channel_kind;
 mod m20260213_000004_direct_messages;
 mod m20260224_000005_soundboard;
+mod m20260227_000006_attachments;
+mod m20260227_000007_sessions;
+mod m20260227_000008_soundboard_media;
+mod m20260227_000009_soundboard_file_path_nullable;
 
 pub struct Migrator;
 
@@ -17,6 +21,10 @@ impl MigratorTrait for Migrator {
             Box::new(m20260213_000003_channel_kind::Migration),
             Box::new(m20260213_000004_direct_messages::Migration),
             Box::new(m20260224_000005_soundboard::Migration),
+            Box::new(m20260227_000006_attachments::Migration),
+            Box::new(m20260227_000007_sessions::Migration),
+            Box::new(m20260227_000008_soundboard_media::Migration),
+            Box::new(m20260227_000009_soundboard_file_path_nullable::Migration),
         ]
     }
 }

src/models.rs

@@ -31,12 +31,12 @@ pub struct Channel {
 }
 
 #[derive(Debug, Clone, Serialize)]
-pub struct Message {
+pub struct Attachment {
     pub id: Uuid,
-    pub channel_id: Uuid,
+    pub media_url: String,
-    pub author_user_id: Uuid,
+    pub mime_type: String,
-    pub body: String,
+    pub size_bytes: i64,
-    pub created_at: DateTimeWithTimeZone,
+    pub original_filename: String,
 }
 
 #[derive(Debug, Clone, Serialize)]
@@ -46,13 +46,14 @@ pub struct BasicUser {
     pub avatar_url: Option<String>,
 }
 
-#[derive(Debug, Clone, Serialize, sea_orm::FromQueryResult)]
+#[derive(Debug, Clone, Serialize)]
 pub struct MessageWithAuthor {
     pub id: Uuid,
     pub channel_id: Uuid,
     pub author_user_id: Uuid,
     pub author_display_name: String,
     pub body: String,
+    pub attachments: Vec<Attachment>,
     pub created_at: DateTimeWithTimeZone,
 }
 
@@ -71,6 +72,7 @@ pub struct DmMessageWithAuthor {
     pub recipient_user_id: Uuid,
     pub author_display_name: String,
     pub body: String,
+    pub attachments: Vec<Attachment>,
     pub created_at: DateTimeWithTimeZone,
 }
 
@@ -91,7 +93,9 @@ pub struct SoundboardSound {
     pub guild_id: Uuid,
     pub name: String,
     pub icon: String,
-    pub file_path: String,
+    pub media_url: String,
+    pub mime_type: Option<String>,
+    pub size_bytes: Option<i64>,
     pub created_by_user_id: Uuid,
     pub created_at: DateTimeWithTimeZone,
 }

src/voice.rs

@@ -10,7 +10,7 @@ use crate::{AppState, db};
 
 #[derive(Default)]
 pub struct VoiceHub {
-    rooms: RwLock<HashMap<Uuid, HashMap<Uuid, ClientHandle>>>,
+    rooms: RwLock<HashMap<Uuid, HashMap<Uuid, HashMap<Uuid, ClientHandle>>>>,
 }
 
 #[derive(Clone)]
@@ -72,7 +72,7 @@ enum ServerEvent {
     },
     PlaySound {
         user_id: Uuid,
-        sound_url: String,
+        media_url: String,
     },
 }
 
@@ -97,10 +97,20 @@ enum ClientEvent {
         is_muted: bool,
     },
     PlaySound {
-        sound_url: String,
+        sound_id: Uuid,
     },
 }
 
+#[derive(Default)]
+struct VoiceStateChange {
+    joined: Option<VoiceParticipant>,
+    left_user_id: Option<Uuid>,
+    video_changed: Option<(Uuid, bool)>,
+    screen_changed: Option<(Uuid, bool)>,
+    speaking_changed: Option<(Uuid, bool)>,
+    mute_changed: Option<(Uuid, bool)>,
+}
+
 impl VoiceHub {
     pub async fn participants(&self, room_id: Uuid) -> Vec<VoiceParticipant> {
         let rooms = self.rooms.read().await;
@@ -109,14 +119,7 @@ impl VoiceHub {
         };
 
         room.iter()
-            .map(|(user_id, handle)| VoiceParticipant {
+            .filter_map(|(user_id, connections)| aggregate_participant(Some(connections), *user_id))
-                user_id: *user_id,
-                display_name: handle.display_name.clone(),
-                is_sharing_video: handle.is_sharing_video,
-                is_sharing_screen: handle.is_sharing_screen,
-                is_speaking: handle.is_speaking,
-                is_muted: handle.is_muted,
-            })
             .collect()
     }
 
@@ -124,28 +127,23 @@ impl VoiceHub {
         &self,
         room_id: Uuid,
         user_id: Uuid,
+        connection_id: Uuid,
         display_name: String,
         tx: mpsc::UnboundedSender<ServerEvent>,
-    ) -> Vec<VoiceParticipant> {
+    ) -> (Vec<VoiceParticipant>, VoiceStateChange) {
         let mut rooms = self.rooms.write().await;
         let room = rooms.entry(room_id).or_default();
 
         let peers = room
             .iter()
-            .map(|(peer_id, peer)| VoiceParticipant {
+            .filter_map(|(peer_id, connections)| aggregate_participant(Some(connections), *peer_id))
-                user_id: *peer_id,
-                display_name: peer.display_name.clone(),
-                is_sharing_video: peer.is_sharing_video,
-                is_sharing_screen: peer.is_sharing_screen,
-                is_speaking: peer.is_speaking,
-                is_muted: peer.is_muted,
-            })
             .collect::<Vec<_>>();
 
-        room.insert(
+        let previous = aggregate_participant(room.get(&user_id), user_id);
-            user_id,
+        room.entry(user_id).or_default().insert(
+            connection_id,
             ClientHandle {
-                display_name: display_name.clone(),
+                display_name,
                 is_sharing_video: false,
                 is_sharing_screen: false,
                 is_speaking: false,
@@ -153,34 +151,31 @@ impl VoiceHub {
                 tx,
             },
         );
+        let current = aggregate_participant(room.get(&user_id), user_id);
 
-        for (peer_id, peer) in room.iter() {
+        (peers, diff_voice_state(previous, current))
-            if *peer_id != user_id {
-                let _ = peer.tx.send(ServerEvent::PeerJoined {
-                    user_id,
-                    display_name: display_name.clone(),
-                });
-            }
-        }
-
-        peers
     }
 
-    async fn leave(&self, room_id: Uuid, user_id: Uuid) {
+    async fn leave(&self, room_id: Uuid, user_id: Uuid, connection_id: Uuid) -> VoiceStateChange {
         let mut rooms = self.rooms.write().await;
         let Some(room) = rooms.get_mut(&room_id) else {
-            return;
+            return VoiceStateChange::default();
         };
 
-        room.remove(&user_id);
+        let previous = aggregate_participant(room.get(&user_id), user_id);
-
+        if let Some(connections) = room.get_mut(&user_id) {
-        for peer in room.values() {
+            connections.remove(&connection_id);
-            let _ = peer.tx.send(ServerEvent::PeerLeft { user_id });
+            if connections.is_empty() {
+                room.remove(&user_id);
+            }
         }
+        let current = aggregate_participant(room.get(&user_id), user_id);
 
         if room.is_empty() {
             rooms.remove(&room_id);
         }
+
+        diff_voice_state(previous, current)
     }
 
     pub async fn relay_signal(
@@ -196,7 +191,10 @@ impl VoiceHub {
             return;
         };
 
-        if let Some(target) = room.get(&to_user_id) {
+        if let Some(target) = room
+            .get(&to_user_id)
+            .and_then(|connections| connections.values().next())
+        {
             let _ = target.tx.send(ServerEvent::Signal {
                 from_user_id,
                 kind,
@@ -205,99 +203,185 @@ impl VoiceHub {
         }
     }
 
-    pub async fn set_video_status(&self, room_id: Uuid, user_id: Uuid, is_sharing_video: bool) {
+    async fn set_video_status(
+        &self,
+        room_id: Uuid,
+        user_id: Uuid,
+        connection_id: Uuid,
+        is_sharing_video: bool,
+    ) -> VoiceStateChange {
         let mut rooms = self.rooms.write().await;
         let Some(room) = rooms.get_mut(&room_id) else {
-            return;
+            return VoiceStateChange::default();
         };
 
-        if let Some(handle) = room.get_mut(&user_id) {
+        let previous = aggregate_participant(room.get(&user_id), user_id);
+        if let Some(handle) = room
+            .get_mut(&user_id)
+            .and_then(|connections| connections.get_mut(&connection_id))
+        {
             handle.is_sharing_video = is_sharing_video;
-
-            for (peer_id, peer) in room.iter() {
-                if *peer_id != user_id {
-                    let _ = peer.tx.send(ServerEvent::VideoStatusChanged {
-                        user_id,
-                        is_sharing_video,
-                    });
-                }
-            }
         }
+        let current = aggregate_participant(room.get(&user_id), user_id);
+        diff_voice_state(previous, current)
     }
 
-    pub async fn set_screen_status(&self, room_id: Uuid, user_id: Uuid, is_sharing_screen: bool) {
+    async fn set_screen_status(
+        &self,
+        room_id: Uuid,
+        user_id: Uuid,
+        connection_id: Uuid,
+        is_sharing_screen: bool,
+    ) -> VoiceStateChange {
         let mut rooms = self.rooms.write().await;
         let Some(room) = rooms.get_mut(&room_id) else {
-            return;
+            return VoiceStateChange::default();
         };
 
-        if let Some(handle) = room.get_mut(&user_id) {
+        let previous = aggregate_participant(room.get(&user_id), user_id);
+        if let Some(handle) = room
+            .get_mut(&user_id)
+            .and_then(|connections| connections.get_mut(&connection_id))
+        {
             handle.is_sharing_screen = is_sharing_screen;
-
-            for (peer_id, peer) in room.iter() {
-                if *peer_id != user_id {
-                    let _ = peer.tx.send(ServerEvent::ScreenStatusChanged {
-                        user_id,
-                        is_sharing_screen,
-                    });
-                }
-            }
         }
+        let current = aggregate_participant(room.get(&user_id), user_id);
+        diff_voice_state(previous, current)
     }
 
-    pub async fn set_speaking_status(&self, room_id: Uuid, user_id: Uuid, is_speaking: bool) {
+    async fn set_speaking_status(
+        &self,
+        room_id: Uuid,
+        user_id: Uuid,
+        connection_id: Uuid,
+        is_speaking: bool,
+    ) -> VoiceStateChange {
         let mut rooms = self.rooms.write().await;
         let Some(room) = rooms.get_mut(&room_id) else {
-            return;
+            return VoiceStateChange::default();
         };
 
-        if let Some(handle) = room.get_mut(&user_id) {
+        let previous = aggregate_participant(room.get(&user_id), user_id);
+        if let Some(handle) = room
+            .get_mut(&user_id)
+            .and_then(|connections| connections.get_mut(&connection_id))
+        {
             handle.is_speaking = is_speaking;
-
-            for (peer_id, peer) in room.iter() {
-                if *peer_id != user_id {
-                    let _ = peer.tx.send(ServerEvent::SpeakingStatusChanged {
-                        user_id,
-                        is_speaking,
-                    });
-                }
-            }
         }
+        let current = aggregate_participant(room.get(&user_id), user_id);
+        diff_voice_state(previous, current)
     }
 
-    pub async fn set_mute_status(&self, room_id: Uuid, user_id: Uuid, is_muted: bool) {
+    async fn set_mute_status(
+        &self,
+        room_id: Uuid,
+        user_id: Uuid,
+        connection_id: Uuid,
+        is_muted: bool,
+    ) -> VoiceStateChange {
         let mut rooms = self.rooms.write().await;
         let Some(room) = rooms.get_mut(&room_id) else {
-            return;
+            return VoiceStateChange::default();
         };
 
-        if let Some(handle) = room.get_mut(&user_id) {
+        let previous = aggregate_participant(room.get(&user_id), user_id);
+        if let Some(handle) = room
+            .get_mut(&user_id)
+            .and_then(|connections| connections.get_mut(&connection_id))
+        {
             handle.is_muted = is_muted;
-
-            for (peer_id, peer) in room.iter() {
-                if *peer_id != user_id {
-                    let _ = peer
-                        .tx
-                        .send(ServerEvent::MuteStatusChanged { user_id, is_muted });
-                }
-            }
         }
+        let current = aggregate_participant(room.get(&user_id), user_id);
+        diff_voice_state(previous, current)
     }
 
-    pub async fn play_sound(&self, room_id: Uuid, user_id: Uuid, sound_url: String) {
+    pub async fn play_sound(&self, room_id: Uuid, user_id: Uuid, media_url: String) {
         let rooms = self.rooms.read().await;
         let Some(room) = rooms.get(&room_id) else {
             return;
         };
 
-        for (peer_id, peer) in room.iter() {
+        for (peer_id, connections) in room.iter() {
             if *peer_id == user_id {
                 continue;
             }
-            let _ = peer.tx.send(ServerEvent::PlaySound {
+            for peer in connections.values() {
+                let _ = peer.tx.send(ServerEvent::PlaySound {
+                    user_id,
+                    media_url: media_url.clone(),
+                });
+            }
+        }
+    }
+
+    async fn emit_change(&self, room_id: Uuid, user_id: Uuid, change: VoiceStateChange) {
+        if is_voice_state_change_empty(&change) {
+            return;
+        }
+
+        let rooms = self.rooms.read().await;
+        let Some(room) = rooms.get(&room_id) else {
+            return;
+        };
+
+        if let Some(participant) = change.joined {
+            broadcast_voice_event(
+                room,
                 user_id,
-                sound_url: sound_url.clone(),
+                ServerEvent::PeerJoined {
-            });
+                    user_id: participant.user_id,
+                    display_name: participant.display_name,
+                },
+            );
+        }
+        if let Some(left_user_id) = change.left_user_id {
+            broadcast_voice_event(
+                room,
+                user_id,
+                ServerEvent::PeerLeft {
+                    user_id: left_user_id,
+                },
+            );
+        }
+        if let Some((changed_user_id, is_sharing_video)) = change.video_changed {
+            broadcast_voice_event(
+                room,
+                user_id,
+                ServerEvent::VideoStatusChanged {
+                    user_id: changed_user_id,
+                    is_sharing_video,
+                },
+            );
+        }
+        if let Some((changed_user_id, is_sharing_screen)) = change.screen_changed {
+            broadcast_voice_event(
+                room,
+                user_id,
+                ServerEvent::ScreenStatusChanged {
+                    user_id: changed_user_id,
+                    is_sharing_screen,
+                },
+            );
+        }
+        if let Some((changed_user_id, is_speaking)) = change.speaking_changed {
+            broadcast_voice_event(
+                room,
+                user_id,
+                ServerEvent::SpeakingStatusChanged {
+                    user_id: changed_user_id,
+                    is_speaking,
+                },
+            );
+        }
+        if let Some((changed_user_id, is_muted)) = change.mute_changed {
+            broadcast_voice_event(
+                room,
+                user_id,
+                ServerEvent::MuteStatusChanged {
+                    user_id: changed_user_id,
+                    is_muted,
+                },
+            );
         }
     }
 }
@@ -306,15 +390,26 @@ pub async fn handle_socket(state: AppState, socket: WebSocket, room_id: Uuid, us
     let Some(user) = db::get_user_by_id(&state.db, user_id).await.ok().flatten() else {
         return;
     };
+    let Ok(Some(guild_id)) = db::guild_id_for_channel(&state.db, room_id).await else {
+        return;
+    };
 
     let (mut ws_sender, mut ws_receiver) = socket.split();
     let (tx, mut rx) = mpsc::unbounded_channel::<ServerEvent>();
+    let connection_id = Uuid::new_v4();
 
-    let peers = state
+    let (peers, change) = state
         .voice
-        .join(room_id, user_id, user.display_name.clone(), tx.clone())
+        .join(
+            room_id,
+            user_id,
+            connection_id,
+            user.display_name.clone(),
+            tx.clone(),
+        )
         .await;
     let _ = tx.send(ServerEvent::Peers { peers });
+    state.voice.emit_change(room_id, user_id, change).await;
 
     let send_task = tokio::spawn(async move {
         while let Some(event) = rx.recv().await {
@@ -343,31 +438,42 @@ pub async fn handle_socket(state: AppState, socket: WebSocket, room_id: Uuid, us
                             .await;
                     }
                     Ok(ClientEvent::SetVideoStatus { is_sharing_video }) => {
-                        state
+                        let change = state
                             .voice
-                            .set_video_status(room_id, user_id, is_sharing_video)
+                            .set_video_status(room_id, user_id, connection_id, is_sharing_video)
                             .await;
+                        state.voice.emit_change(room_id, user_id, change).await;
                     }
                     Ok(ClientEvent::SetScreenStatus { is_sharing_screen }) => {
-                        state
+                        let change = state
                             .voice
-                            .set_screen_status(room_id, user_id, is_sharing_screen)
+                            .set_screen_status(room_id, user_id, connection_id, is_sharing_screen)
                             .await;
+                        state.voice.emit_change(room_id, user_id, change).await;
                     }
                     Ok(ClientEvent::SetSpeakingStatus { is_speaking }) => {
-                        state
+                        let change = state
                             .voice
-                            .set_speaking_status(room_id, user_id, is_speaking)
+                            .set_speaking_status(room_id, user_id, connection_id, is_speaking)
                             .await;
+                        state.voice.emit_change(room_id, user_id, change).await;
                     }
                     Ok(ClientEvent::SetMuteStatus { is_muted }) => {
-                        state
+                        let change = state
                             .voice
-                            .set_mute_status(room_id, user_id, is_muted)
+                            .set_mute_status(room_id, user_id, connection_id, is_muted)
                             .await;
+                        state.voice.emit_change(room_id, user_id, change).await;
                     }
-                    Ok(ClientEvent::PlaySound { sound_url }) => {
+                    Ok(ClientEvent::PlaySound { sound_id }) => {
-                        state.voice.play_sound(room_id, user_id, sound_url).await;
+                        if let Ok(Some(sound)) = db::get_sound_by_id(&state.db, sound_id).await
+                            && sound.guild_id == guild_id
+                        {
+                            state
+                                .voice
+                                .play_sound(room_id, user_id, sound.media_url)
+                                .await;
+                        }
                     }
                     Err(err) => {
                         let _ = tx.send(ServerEvent::Error {
@@ -382,5 +488,183 @@ pub async fn handle_socket(state: AppState, socket: WebSocket, room_id: Uuid, us
     }
 
     send_task.abort();
-    state.voice.leave(room_id, user_id).await;
+    let change = state.voice.leave(room_id, user_id, connection_id).await;
+    state.voice.emit_change(room_id, user_id, change).await;
+}
+
+fn aggregate_participant(
+    connections: Option<&HashMap<Uuid, ClientHandle>>,
+    user_id: Uuid,
+) -> Option<VoiceParticipant> {
+    let connections = connections?;
+    if connections.is_empty() {
+        return None;
+    }
+
+    let mut handles = connections.values();
+    let first = handles.next()?;
+    Some(VoiceParticipant {
+        user_id,
+        display_name: first.display_name.clone(),
+        is_sharing_video: connections.values().any(|handle| handle.is_sharing_video),
+        is_sharing_screen: connections.values().any(|handle| handle.is_sharing_screen),
+        is_speaking: connections.values().any(|handle| handle.is_speaking),
+        is_muted: connections.values().all(|handle| handle.is_muted),
+    })
+}
+
+fn diff_voice_state(
+    previous: Option<VoiceParticipant>,
+    current: Option<VoiceParticipant>,
+) -> VoiceStateChange {
+    match (previous, current) {
+        (None, None) => VoiceStateChange::default(),
+        (None, Some(current)) => VoiceStateChange {
+            joined: Some(current),
+            ..Default::default()
+        },
+        (Some(previous), None) => VoiceStateChange {
+            left_user_id: Some(previous.user_id),
+            ..Default::default()
+        },
+        (Some(previous), Some(current)) => VoiceStateChange {
+            video_changed: (previous.is_sharing_video != current.is_sharing_video)
+                .then_some((current.user_id, current.is_sharing_video)),
+            screen_changed: (previous.is_sharing_screen != current.is_sharing_screen)
+                .then_some((current.user_id, current.is_sharing_screen)),
+            speaking_changed: (previous.is_speaking != current.is_speaking)
+                .then_some((current.user_id, current.is_speaking)),
+            mute_changed: (previous.is_muted != current.is_muted)
+                .then_some((current.user_id, current.is_muted)),
+            ..Default::default()
+        },
+    }
+}
+
+fn broadcast_voice_event(
+    room: &HashMap<Uuid, HashMap<Uuid, ClientHandle>>,
+    source_user_id: Uuid,
+    event: ServerEvent,
+) {
+    for (peer_id, connections) in room {
+        if *peer_id == source_user_id {
+            continue;
+        }
+        for peer in connections.values() {
+            let _ = peer.tx.send(event.clone());
+        }
+    }
+}
+
+fn is_voice_state_change_empty(change: &VoiceStateChange) -> bool {
+    change.joined.is_none()
+        && change.left_user_id.is_none()
+        && change.video_changed.is_none()
+        && change.screen_changed.is_none()
+        && change.speaking_changed.is_none()
+        && change.mute_changed.is_none()
+}
+
+#[cfg(test)]
+mod tests {
+    use super::{VoiceHub, aggregate_participant};
+    use std::collections::HashMap;
+    use tokio::sync::mpsc;
+    use uuid::Uuid;
+
+    #[tokio::test]
+    async fn multiple_connections_keep_voice_participant_until_last_leave() {
+        let hub = VoiceHub::default();
+        let room_id = Uuid::new_v4();
+        let user_id = Uuid::new_v4();
+        let first_connection = Uuid::new_v4();
+        let second_connection = Uuid::new_v4();
+        let (tx1, _rx1) = mpsc::unbounded_channel();
+        let (tx2, _rx2) = mpsc::unbounded_channel();
+
+        let (_peers, first_join) = hub
+            .join(room_id, user_id, first_connection, "User".to_string(), tx1)
+            .await;
+        let (_peers, second_join) = hub
+            .join(room_id, user_id, second_connection, "User".to_string(), tx2)
+            .await;
+        let first_leave = hub.leave(room_id, user_id, first_connection).await;
+        let second_leave = hub.leave(room_id, user_id, second_connection).await;
+
+        assert!(first_join.joined.is_some());
+        assert!(second_join.joined.is_none());
+        assert!(first_leave.left_user_id.is_none());
+        assert_eq!(second_leave.left_user_id, Some(user_id));
+    }
+
+    #[tokio::test]
+    async fn voice_mute_state_only_flips_when_all_connections_are_muted() {
+        let hub = VoiceHub::default();
+        let room_id = Uuid::new_v4();
+        let user_id = Uuid::new_v4();
+        let first_connection = Uuid::new_v4();
+        let second_connection = Uuid::new_v4();
+        let (tx1, _rx1) = mpsc::unbounded_channel();
+        let (tx2, _rx2) = mpsc::unbounded_channel();
+
+        let _ = hub
+            .join(room_id, user_id, first_connection, "User".to_string(), tx1)
+            .await;
+        let _ = hub
+            .join(room_id, user_id, second_connection, "User".to_string(), tx2)
+            .await;
+
+        let first_mute = hub
+            .set_mute_status(room_id, user_id, first_connection, true)
+            .await;
+        let second_mute = hub
+            .set_mute_status(room_id, user_id, second_connection, true)
+            .await;
+        let unmute = hub
+            .set_mute_status(room_id, user_id, first_connection, false)
+            .await;
+
+        assert!(first_mute.mute_changed.is_none());
+        assert_eq!(second_mute.mute_changed, Some((user_id, true)));
+        assert_eq!(unmute.mute_changed, Some((user_id, false)));
+    }
+
+    #[test]
+    fn aggregate_participant_combines_connection_state() {
+        let user_id = Uuid::new_v4();
+        let first_connection = Uuid::new_v4();
+        let second_connection = Uuid::new_v4();
+        let mut connections = HashMap::new();
+        let (tx1, _rx1) = mpsc::unbounded_channel();
+        let (tx2, _rx2) = mpsc::unbounded_channel();
+
+        connections.insert(
+            first_connection,
+            super::ClientHandle {
+                display_name: "User".to_string(),
+                is_sharing_video: true,
+                is_sharing_screen: false,
+                is_speaking: false,
+                is_muted: true,
+                tx: tx1,
+            },
+        );
+        connections.insert(
+            second_connection,
+            super::ClientHandle {
+                display_name: "User".to_string(),
+                is_sharing_video: false,
+                is_sharing_screen: true,
+                is_speaking: true,
+                is_muted: false,
+                tx: tx2,
+            },
+        );
+
+        let participant = aggregate_participant(Some(&connections), user_id).unwrap();
+        assert!(participant.is_sharing_video);
+        assert!(participant.is_sharing_screen);
+        assert!(participant.is_speaking);
+        assert!(!participant.is_muted);
+    }
 }

static/index.html

@@ -1,3 +1,4 @@
+<!-- Generated from shared-html/index.template.html. Do not edit directly. -->
 <!doctype html>
 <html lang="en">
 
@@ -5,12 +6,9 @@
   <meta charset="UTF-8" />
   <meta name="viewport" content="width=device-width, initial-scale=1.0, viewport-fit=cover" />
   <title>Chattz</title>
-  <link rel="preconnect" href="https://fonts.googleapis.com">
-  <link rel="preconnect" href="https://fonts.gstatic.com" crossorigin>
-  <link href="https://fonts.googleapis.com/css2?family=Inter:wght@400;500;600;700;800&display=swap" rel="stylesheet">
   <link rel="stylesheet" href="/static/styles.css" />
   <!-- Lucide Icons -->
-  <script src="https://unpkg.com/lucide@latest"></script>
+  <script src="/static/vendor/lucide.min.js"></script>
 </head>
 
 <body>
@@ -119,6 +117,10 @@
             <div class="user-status">Online</div>
           </div>
           <div class="user-actions">
+            <div id="update-notifier" class="update-notifier hidden">
+              <button id="update-download-btn" title="Download Update"><i data-lucide="download"></i></button>
+              <button id="update-install-btn" title="Install Update" class="hidden"><i data-lucide="arrow-up-circle"></i></button>
+            </div>
             <button id="user-settings-btn" title="Settings"><i data-lucide="settings"></i></button>
             <button id="logout-btn" title="Logout"><i data-lucide="log-out"></i></button>
           </div>
@@ -144,6 +146,10 @@
 
       <div class="chat-input-wrapper">
         <form id="message-form" class="message-form">
+          <input id="media-file-input" type="file" class="hidden-file-input" accept="image/*,video/*,audio/*,.pdf,.txt,.zip,.rar,.7z,.tar,.gz,.json,.csv,.md" />
+          <button type="button" id="media-upload-btn" class="input-action-btn" title="Upload File">
+            <i data-lucide="paperclip"></i>
+          </button>
           <button type="button" id="gif-btn" class="input-action-btn" title="Open GIF Picker">
             <i data-lucide="image"></i>
           </button>
@@ -265,7 +271,17 @@
     </div>
   </div>
 
-  <script src="/static/app.js?v=20260225-voice-audiofix-1" defer></script>
+  <div id="upload-limit-modal" class="modal-container hidden">
+    <div class="modal">
+      <h2>Upload Too Large</h2>
+      <p id="upload-limit-message" class="modal-copy">Uploads are limited to 50 MB per file.</p>
+      <div class="modal-footer">
+        <button type="button" class="submit-btn" id="upload-limit-ok">OK</button>
+      </div>
+    </div>
+  </div>
+
+  <script type="module" src="/static/app.js?v=20260227-shared-core-1"></script>
 </body>
 
 </html>

static/styles.css

@@ -885,6 +885,10 @@ select {
   color: var(--text-normal);
 }
 
+.hidden-file-input {
+  display: none;
+}
+
 /* ═══════════════════════════════════════════════════════════ */
 /*  GIF Picker Modal                                           */
 /* ═══════════════════════════════════════════════════════════ */
@@ -996,6 +1000,91 @@ select {
   object-fit: contain;
 }
 
+.msg-attachment {
+  display: block;
+  margin-top: 8px;
+}
+
+.msg-attachment-image {
+  max-width: min(440px, 100%);
+  border-radius: var(--radius-md);
+  overflow: hidden;
+}
+
+.msg-attachment-image img {
+  width: 100%;
+  max-height: 360px;
+  object-fit: contain;
+  display: block;
+  background: rgba(0, 0, 0, 0.18);
+}
+
+.msg-attachment-video {
+  max-width: min(520px, 100%);
+}
+
+.msg-attachment-video video {
+  width: 100%;
+  max-height: 420px;
+  border-radius: var(--radius-md);
+  background: #000;
+}
+
+.msg-attachment-audio {
+  display: flex;
+  flex-direction: column;
+  gap: 10px;
+  padding: 12px 14px;
+  max-width: min(420px, 100%);
+  border-radius: var(--radius-md);
+  background: rgba(255, 255, 255, 0.04);
+  border: 1px solid rgba(255, 255, 255, 0.06);
+}
+
+.msg-attachment-audio audio {
+  width: 100%;
+}
+
+.msg-attachment-audio a {
+  color: var(--text-link);
+  font-size: 13px;
+}
+
+.msg-attachment-file {
+  display: inline-flex;
+  align-items: center;
+  gap: 10px;
+  padding: 10px 12px;
+  max-width: min(420px, 100%);
+  border-radius: var(--radius-md);
+  background: rgba(255, 255, 255, 0.04);
+  border: 1px solid rgba(255, 255, 255, 0.06);
+  color: var(--text-normal);
+}
+
+.msg-attachment-file:hover {
+  background: rgba(255, 255, 255, 0.07);
+}
+
+.msg-attachment-file i {
+  width: 18px;
+  height: 18px;
+  color: var(--text-link);
+  flex-shrink: 0;
+}
+
+.msg-attachment-file span {
+  overflow: hidden;
+  text-overflow: ellipsis;
+  white-space: nowrap;
+}
+
+.msg-attachment-file small {
+  color: var(--text-muted);
+  margin-left: auto;
+  white-space: nowrap;
+}
+
 /* ═══════════════════════════════════════════════════════════ */
 /*  Sound Board                                               */
 /* ═══════════════════════════════════════════════════════════ */
@@ -1389,6 +1478,13 @@ select {
   letter-spacing: -0.3px;
 }
 
+.modal-copy {
+  margin: 0;
+  text-align: center;
+  color: var(--text-normal);
+  line-height: 1.5;
+}
+
 .form-item {
   margin-bottom: 20px;
 }
@@ -1618,4 +1714,4 @@ select {
   .chat-header {
     padding: 0 8px;
   }
-}
+}