Merge pull request #1276 from MODSetter/dev_mod

feat: add startup for desktop app

surfsense_backend/alembic/versions/127_add_report_content_type.py

@@ -1,7 +1,7 @@
-"""126_add_report_content_type
+"""127_add_report_content_type
 
-Revision ID: 126
-Revises: 125
+Revision ID: 127
+Revises: 126
 Create Date: 2026-04-15
 
 Adds content_type column to reports table to distinguish between
@@ -16,8 +16,8 @@ import sqlalchemy as sa
 
 from alembic import op
 
-revision: str = "126"
-down_revision: str | None = "125"
+revision: str = "127"
+down_revision: str | None = "126"
 branch_labels: str | Sequence[str] | None = None
 depends_on: str | Sequence[str] | None = None
 

surfsense_backend/alembic/versions/128_seed_build_resume_prompt.py

@@ -1,7 +1,7 @@
-"""127_seed_build_resume_prompt
+"""128_seed_build_resume_prompt
 
-Revision ID: 127
-Revises: 126
+Revision ID: 128
+Revises: 127
 Create Date: 2026-04-15
 
 Seeds the 'Build Resume' default prompt for all existing users.
@@ -16,8 +16,8 @@ import sqlalchemy as sa
 
 from alembic import op
 
-revision: str = "127"
-down_revision: str | None = "126"
+revision: str = "128"
+down_revision: str | None = "127"
 branch_labels: str | Sequence[str] | None = None
 depends_on: str | Sequence[str] | None = None
 

surfsense_desktop/src/ipc/channels.ts

@@ -43,4 +43,12 @@ export const IPC_CHANNELS = {
   // Active search space
   GET_ACTIVE_SEARCH_SPACE: 'search-space:get-active',
   SET_ACTIVE_SEARCH_SPACE: 'search-space:set-active',
+  // Launch on system startup
+  GET_AUTO_LAUNCH: 'auto-launch:get',
+  SET_AUTO_LAUNCH: 'auto-launch:set',
+  // Analytics (PostHog) bridge: renderer <-> main
+  ANALYTICS_IDENTIFY: 'analytics:identify',
+  ANALYTICS_RESET: 'analytics:reset',
+  ANALYTICS_CAPTURE: 'analytics:capture',
+  ANALYTICS_GET_CONTEXT: 'analytics:get-context',
 } as const;

surfsense_desktop/src/ipc/handlers.ts

@@ -24,10 +24,18 @@ import {
   type WatchedFolderConfig,
 } from '../modules/folder-watcher';
 import { getShortcuts, setShortcuts, type ShortcutConfig } from '../modules/shortcuts';
+import { getAutoLaunchState, setAutoLaunch } from '../modules/auto-launch';
 import { getActiveSearchSpaceId, setActiveSearchSpaceId } from '../modules/active-search-space';
 import { reregisterQuickAsk } from '../modules/quick-ask';
 import { reregisterAutocomplete } from '../modules/autocomplete';
 import { reregisterGeneralAssist } from '../modules/tray';
+import {
+  getDistinctId,
+  getMachineId,
+  identifyUser as analyticsIdentify,
+  resetUser as analyticsReset,
+  trackEvent,
+} from '../modules/analytics';
 
 let authTokens: { bearer: string; refresh: string } | null = null;
 
@@ -120,6 +128,21 @@ export function registerIpcHandlers(): void {
 
   ipcMain.handle(IPC_CHANNELS.GET_SHORTCUTS, () => getShortcuts());
 
+  ipcMain.handle(IPC_CHANNELS.GET_AUTO_LAUNCH, () => getAutoLaunchState());
+
+  ipcMain.handle(
+    IPC_CHANNELS.SET_AUTO_LAUNCH,
+    async (_event, payload: { enabled: boolean; openAsHidden?: boolean }) => {
+      const next = await setAutoLaunch(payload.enabled, payload.openAsHidden);
+      trackEvent('desktop_auto_launch_toggled', {
+        enabled: next.enabled,
+        open_as_hidden: next.openAsHidden,
+        supported: next.supported,
+      });
+      return next;
+    },
+  );
+
   ipcMain.handle(IPC_CHANNELS.GET_ACTIVE_SEARCH_SPACE, () => getActiveSearchSpaceId());
 
   ipcMain.handle(IPC_CHANNELS.SET_ACTIVE_SEARCH_SPACE, (_event, id: string) =>
@@ -131,6 +154,41 @@ export function registerIpcHandlers(): void {
     if (config.generalAssist) await reregisterGeneralAssist();
     if (config.quickAsk) await reregisterQuickAsk();
     if (config.autocomplete) await reregisterAutocomplete();
+    trackEvent('desktop_shortcut_updated', {
+      keys: Object.keys(config),
+    });
     return updated;
   });
+
+  // Analytics bridge — the renderer (web UI) hands the logged-in user down
+  // to the main process so desktop-only events are attributed to the same
+  // PostHog person, not just an anonymous machine ID.
+  ipcMain.handle(
+    IPC_CHANNELS.ANALYTICS_IDENTIFY,
+    (_event, payload: { userId: string; properties?: Record<string, unknown> }) => {
+      if (!payload?.userId) return;
+      analyticsIdentify(String(payload.userId), payload.properties);
+    }
+  );
+
+  ipcMain.handle(IPC_CHANNELS.ANALYTICS_RESET, () => {
+    analyticsReset();
+  });
+
+  ipcMain.handle(
+    IPC_CHANNELS.ANALYTICS_CAPTURE,
+    (_event, payload: { event: string; properties?: Record<string, unknown> }) => {
+      if (!payload?.event) return;
+      trackEvent(payload.event, payload.properties);
+    }
+  );
+
+  ipcMain.handle(IPC_CHANNELS.ANALYTICS_GET_CONTEXT, () => {
+    return {
+      distinctId: getDistinctId(),
+      machineId: getMachineId(),
+      appVersion: app.getVersion(),
+      platform: process.platform,
+    };
+  });
 }

surfsense_desktop/src/main.ts

@@ -1,10 +1,9 @@
-import { app, BrowserWindow } from 'electron';
+import { app } from 'electron';
 
-let isQuitting = false;
 import { registerGlobalErrorHandlers, showErrorDialog } from './modules/errors';
 import { startNextServer } from './modules/server';
-import { createMainWindow, getMainWindow } from './modules/window';
-import { setupDeepLinks, handlePendingDeepLink } from './modules/deep-links';
+import { createMainWindow, getMainWindow, markQuitting } from './modules/window';
+import { setupDeepLinks, handlePendingDeepLink, hasPendingDeepLink } from './modules/deep-links';
 import { setupAutoUpdater } from './modules/auto-updater';
 import { setupMenu } from './modules/menu';
 import { registerQuickAsk, unregisterQuickAsk } from './modules/quick-ask';
@@ -13,6 +12,12 @@ import { registerFolderWatcher, unregisterFolderWatcher } from './modules/folder
 import { registerIpcHandlers } from './ipc/handlers';
 import { createTray, destroyTray } from './modules/tray';
 import { initAnalytics, shutdownAnalytics, trackEvent } from './modules/analytics';
+import {
+  applyAutoLaunchDefaults,
+  shouldStartHidden,
+  syncAutoLaunchOnStartup,
+  wasLaunchedAtLogin,
+} from './modules/auto-launch';
 
 registerGlobalErrorHandlers();
 
@@ -24,7 +29,12 @@ registerIpcHandlers();
 
 app.whenReady().then(async () => {
   initAnalytics();
-  trackEvent('desktop_app_launched');
+  const launchedAtLogin = wasLaunchedAtLogin();
+  const startedHidden = shouldStartHidden();
+  trackEvent('desktop_app_launched', {
+    launched_at_login: launchedAtLogin,
+    started_hidden: startedHidden,
+  });
   setupMenu();
   try {
     await startNextServer();
@@ -35,16 +45,19 @@ app.whenReady().then(async () => {
   }
 
   await createTray();
-
-  const win = createMainWindow('/dashboard');
-
-  // Minimize to tray instead of closing the app
-  win.on('close', (e) => {
-    if (!isQuitting) {
-      e.preventDefault();
-      win.hide();
+  const defaultsApplied = await applyAutoLaunchDefaults();
+  if (defaultsApplied) {
+    trackEvent('desktop_auto_launch_defaulted_on');
+  }
+  await syncAutoLaunchOnStartup();
+
+  // When started by the OS at login we stay quietly in the tray. The window
+  // is created lazily on first user interaction (tray click / activate).
+  // Exception: if a deep link is queued, the user explicitly asked to land
+  // in the app — don't swallow it.
+  if (!startedHidden || hasPendingDeepLink()) {
+    createMainWindow('/dashboard');
   }
-  });
 
   await registerQuickAsk();
   await registerAutocomplete();
@@ -55,6 +68,7 @@ app.whenReady().then(async () => {
 
   app.on('activate', () => {
     const mw = getMainWindow();
+    trackEvent('desktop_app_activated');
     if (!mw || mw.isDestroyed()) {
       createMainWindow('/dashboard');
     } else {
@@ -70,7 +84,8 @@ app.on('window-all-closed', () => {
 });
 
 app.on('before-quit', () => {
-  isQuitting = true;
+  markQuitting();
+  trackEvent('desktop_app_quit');
 });
 
 let didCleanup = false;

surfsense_desktop/src/modules/analytics.ts

@@ -3,14 +3,27 @@ import { machineIdSync } from 'node-machine-id';
 import { app } from 'electron';
 
 let client: PostHog | null = null;
-let distinctId = '';
+let machineId = '';
+let currentDistinctId = '';
+let identifiedUserId: string | null = null;
+
+function baseProperties(): Record<string, unknown> {
+  return {
+    platform: 'desktop',
+    app_version: app.getVersion(),
+    os: process.platform,
+    arch: process.arch,
+    machine_id: machineId,
+  };
+}
 
 export function initAnalytics(): void {
   const key = process.env.POSTHOG_KEY;
   if (!key) return;
 
   try {
-    distinctId = machineIdSync(true);
+    machineId = machineIdSync(true);
+    currentDistinctId = machineId;
   } catch {
     return;
   }
@@ -22,17 +35,92 @@ export function initAnalytics(): void {
   });
 }
 
-export function trackEvent(event: string, properties?: Record<string, unknown>): void {
+export function getMachineId(): string {
+  return machineId;
+}
+
+export function getDistinctId(): string {
+  return currentDistinctId;
+}
+
+/**
+ * Identify the current logged-in user in PostHog so main-process desktop
+ * events (and linked anonymous machine events) are attributed to that person.
+ *
+ * Idempotent: calling identify repeatedly with the same userId is a no-op.
+ */
+export function identifyUser(
+  userId: string,
+  properties?: Record<string, unknown>
+): void {
+  if (!client || !userId) return;
+  if (identifiedUserId === userId) {
+    // Already identified — only refresh person properties
+    try {
+      client.identify({
+        distinctId: userId,
+        properties: {
+          ...baseProperties(),
+          $set: {
+            ...(properties || {}),
+            platform: 'desktop',
+            last_seen_at: new Date().toISOString(),
+          },
+        },
+      });
+    } catch {
+      // ignore
+    }
+    return;
+  }
+
+  try {
+    // Link the anonymous machine distinct ID to the authenticated user
+    client.identify({
+      distinctId: userId,
+      properties: {
+        ...baseProperties(),
+        $anon_distinct_id: machineId,
+        $set: {
+          ...(properties || {}),
+          platform: 'desktop',
+          last_seen_at: new Date().toISOString(),
+        },
+        $set_once: {
+          first_seen_platform: 'desktop',
+        },
+      },
+    });
+
+    identifiedUserId = userId;
+    currentDistinctId = userId;
+  } catch {
+    // Analytics must never break the app
+  }
+}
+
+/**
+ * Reset user identity on logout. Subsequent events are captured anonymously
+ * against the machine ID until the user logs in again.
+ */
+export function resetUser(): void {
+  if (!client) return;
+  identifiedUserId = null;
+  currentDistinctId = machineId;
+}
+
+export function trackEvent(
+  event: string,
+  properties?: Record<string, unknown>
+): void {
   if (!client) return;
 
   try {
     client.capture({
-      distinctId,
+      distinctId: currentDistinctId || machineId,
       event,
       properties: {
-        platform: 'desktop',
-        app_version: app.getVersion(),
-        os: process.platform,
+        ...baseProperties(),
         ...properties,
       },
     });

surfsense_desktop/src/modules/auto-launch.ts

@@ -0,0 +1,304 @@
+import { app } from 'electron';
+import fs from 'fs';
+import os from 'os';
+import path from 'path';
+
+// ---------------------------------------------------------------------------
+// Launch on system startup ("auto-launch" / "open at login").
+//
+// macOS + Windows : uses Electron's built-in `app.setLoginItemSettings()`.
+// Linux           : writes a freedesktop autostart `.desktop` file into
+//                   `~/.config/autostart/`. Electron's API is a no-op there.
+//
+// The OS is the source of truth for whether we're enabled (so a user who
+// disables us via System Settings / GNOME Tweaks isn't silently overridden).
+// We persist a small companion record in electron-store for things the OS
+// can't tell us — currently just `openAsHidden`, since on Windows we encode
+// it as a CLI arg and on Linux as part of the Exec line, but on a fresh
+// startup we still want the renderer toggle to reflect the user's intent.
+// ---------------------------------------------------------------------------
+
+const STORE_KEY = 'launchAtLogin';
+const HIDDEN_FLAG = '--hidden';
+const LINUX_DESKTOP_FILENAME = 'surfsense.desktop';
+
+export interface AutoLaunchState {
+  enabled: boolean;
+  openAsHidden: boolean;
+  supported: boolean;
+}
+
+interface PersistedState {
+  enabled: boolean;
+  openAsHidden: boolean;
+  // True once we've run the first-launch defaults (opt-in to auto-launch).
+  // We never re-apply defaults if this is set, so a user who has explicitly
+  // turned auto-launch off stays off forever.
+  defaultsApplied: boolean;
+}
+
+const DEFAULTS: PersistedState = {
+  enabled: false,
+  openAsHidden: true,
+  defaultsApplied: false,
+};
+
+// eslint-disable-next-line @typescript-eslint/no-explicit-any -- lazily imported ESM module; matches shortcuts.ts pattern
+let store: any = null;
+
+async function getStore() {
+  if (!store) {
+    const { default: Store } = await import('electron-store');
+    store = new Store({
+      name: 'auto-launch',
+      defaults: { [STORE_KEY]: DEFAULTS },
+    });
+  }
+  return store;
+}
+
+async function readPersisted(): Promise<PersistedState> {
+  const s = await getStore();
+  const stored = s.get(STORE_KEY) as Partial<PersistedState> | undefined;
+  return { ...DEFAULTS, ...(stored ?? {}) };
+}
+
+async function writePersisted(next: PersistedState): Promise<void> {
+  const s = await getStore();
+  s.set(STORE_KEY, next);
+}
+
+// ---------------------------------------------------------------------------
+// Platform support
+// ---------------------------------------------------------------------------
+
+// Auto-launch only makes sense for the packaged app — in dev `process.execPath`
+// is the local Electron binary, so registering it would point the OS at a
+// throwaway path the next time the dev server isn't running.
+function isSupported(): boolean {
+  if (!app.isPackaged) return false;
+  return ['darwin', 'win32', 'linux'].includes(process.platform);
+}
+
+// ---------------------------------------------------------------------------
+// Linux: ~/.config/autostart/surfsense.desktop
+// ---------------------------------------------------------------------------
+
+function linuxAutostartDir(): string {
+  const xdg = process.env.XDG_CONFIG_HOME;
+  const base = xdg && xdg.length > 0 ? xdg : path.join(os.homedir(), '.config');
+  return path.join(base, 'autostart');
+}
+
+function linuxAutostartFile(): string {
+  return path.join(linuxAutostartDir(), LINUX_DESKTOP_FILENAME);
+}
+
+// AppImages move around with the user — `process.execPath` points at a temp
+// mount, so we have to use the original AppImage path exposed via env.
+function linuxExecPath(): string {
+  return process.env.APPIMAGE && process.env.APPIMAGE.length > 0
+    ? process.env.APPIMAGE
+    : process.execPath;
+}
+
+function escapeDesktopExecArg(value: string): string {
+  // Freedesktop `.desktop` Exec values require quoted args when spaces are
+  // present. We keep this intentionally minimal and escape only characters
+  // that can break quoted parsing.
+  return `"${value.replace(/(["\\`$])/g, '\\$1')}"`;
+}
+
+function writeLinuxDesktopFile(openAsHidden: boolean): void {
+  const exec = escapeDesktopExecArg(linuxExecPath());
+  const args = openAsHidden ? ` ${HIDDEN_FLAG}` : '';
+  const contents = [
+    '[Desktop Entry]',
+    'Type=Application',
+    'Version=1.0',
+    'Name=SurfSense',
+    'Comment=AI-powered research assistant',
+    `Exec=${exec}${args}`,
+    'Terminal=false',
+    'Categories=Utility;Office;',
+    'X-GNOME-Autostart-enabled=true',
+    `X-GNOME-Autostart-Delay=${openAsHidden ? '5' : '0'}`,
+    '',
+  ].join('\n');
+
+  fs.mkdirSync(linuxAutostartDir(), { recursive: true });
+  fs.writeFileSync(linuxAutostartFile(), contents, { mode: 0o644 });
+}
+
+function removeLinuxDesktopFile(): void {
+  try {
+    fs.unlinkSync(linuxAutostartFile());
+  } catch (err: unknown) {
+    if ((err as NodeJS.ErrnoException)?.code !== 'ENOENT') throw err;
+  }
+}
+
+function readLinuxDesktopFile(): boolean {
+  return fs.existsSync(linuxAutostartFile());
+}
+
+// ---------------------------------------------------------------------------
+// Public API
+// ---------------------------------------------------------------------------
+
+export async function getAutoLaunchState(): Promise<AutoLaunchState> {
+  const supported = isSupported();
+  const persisted = await readPersisted();
+
+  if (!supported) {
+    return { enabled: false, openAsHidden: persisted.openAsHidden, supported: false };
+  }
+
+  // Trust the OS state — the user may have disabled it from system settings.
+  return { enabled: readOsEnabled(), openAsHidden: persisted.openAsHidden, supported: true };
+}
+
+export async function setAutoLaunch(
+  enabled: boolean,
+  openAsHidden: boolean = DEFAULTS.openAsHidden,
+): Promise<AutoLaunchState> {
+  const supported = isSupported();
+
+  if (!supported) {
+    return { enabled: false, openAsHidden, supported: false };
+  }
+
+  applySystemRegistration(enabled, openAsHidden);
+  // Preserve `defaultsApplied` (and any future fields) — and explicitly
+  // mark them as applied, since the user has now made an intentional choice.
+  await writePersisted({ enabled, openAsHidden, defaultsApplied: true });
+  return { enabled, openAsHidden, supported: true };
+}
+
+function applySystemRegistration(enabled: boolean, openAsHidden: boolean): void {
+  if (process.platform === 'linux') {
+    if (enabled) writeLinuxDesktopFile(openAsHidden);
+    else removeLinuxDesktopFile();
+    return;
+  }
+
+  if (!enabled) {
+    app.setLoginItemSettings({ openAtLogin: false });
+    return;
+  }
+
+  if (process.platform === 'win32') {
+    // On Windows we can't tell the OS to "launch hidden" — instead we pass an
+    // arg the app introspects on boot to skip showing the main window.
+    app.setLoginItemSettings({
+      openAtLogin: true,
+      args: openAsHidden ? [HIDDEN_FLAG] : [],
+    });
+    return;
+  }
+
+  // darwin
+  app.setLoginItemSettings({
+    openAtLogin: true,
+    openAsHidden,
+  });
+}
+
+// First-launch opt-in: register SurfSense as a hidden login item so the tray,
+// global shortcuts, and folder watchers are ready right after the user signs
+// in. Runs at most once per installation — the `defaultsApplied` flag is
+// flipped before we ever touch the OS so a failure to register doesn't cause
+// us to retry on every boot, and a user who turns the toggle off afterwards
+// is never silently re-enabled.
+//
+// Returns whether the defaults were actually applied this boot, so callers
+// can fire an analytics event without coupling this module to PostHog.
+export async function applyAutoLaunchDefaults(): Promise<boolean> {
+  if (!isSupported()) return false;
+  const persisted = await readPersisted();
+  if (persisted.defaultsApplied) return false;
+
+  // Mark the defaults as applied *first*. If `applySystemRegistration`
+  // throws (e.g. read-only home dir on Linux), we'd rather silently leave
+  // the user un-registered than spam them with a failed registration on
+  // every single boot.
+  const next: PersistedState = {
+    enabled: true,
+    openAsHidden: true,
+    defaultsApplied: true,
+  };
+
+  try {
+    applySystemRegistration(true, true);
+  } catch (err) {
+    console.error('[auto-launch] First-run registration failed:', err);
+    next.enabled = false;
+  }
+
+  await writePersisted(next);
+  return next.enabled;
+}
+
+// Called once at startup. Goal:
+//   * If the OS-level entry is already enabled, re-assert it so a moved
+//     binary (Windows reinstall to a new dir, Linux AppImage moved by user)
+//     gets its registered path refreshed.
+//   * If the OS-level entry has been disabled — typically because the user
+//     turned it off in System Settings / GNOME Tweaks — *respect that* and
+//     reconcile our persisted state to match. We never silently re-enable
+//     a login item the user explicitly turned off.
+export async function syncAutoLaunchOnStartup(): Promise<void> {
+  if (!isSupported()) return;
+
+  const persisted = await readPersisted();
+  const osEnabled = readOsEnabled();
+
+  if (!osEnabled) {
+    // User (or some other tool) turned us off out-of-band. Don't re-enable;
+    // just bring our persisted state in sync so the settings UI reflects
+    // reality on the next render.
+    if (persisted.enabled) {
+      await writePersisted({ ...persisted, enabled: false });
+    }
+    return;
+  }
+
+  // OS says we're enabled — refresh the registration so the recorded path /
+  // args match this binary. Idempotent on macOS; corrects path drift on
+  // Windows and Linux. If our persisted state was somehow stale we also
+  // bring it back in line.
+  try {
+    applySystemRegistration(true, persisted.openAsHidden);
+    if (!persisted.enabled) {
+      await writePersisted({ ...persisted, enabled: true });
+    }
+  } catch (err) {
+    console.error('[auto-launch] Failed to re-assert login item:', err);
+  }
+}
+
+function readOsEnabled(): boolean {
+  if (process.platform === 'linux') return readLinuxDesktopFile();
+  return app.getLoginItemSettings().openAtLogin;
+}
+
+// True when the OS launched us as part of login (used for analytics).
+export function wasLaunchedAtLogin(): boolean {
+  if (process.argv.includes(HIDDEN_FLAG)) return true;
+  if (process.platform === 'darwin') {
+    const settings = app.getLoginItemSettings();
+    return settings.wasOpenedAtLogin || settings.wasOpenedAsHidden;
+  }
+  return false;
+}
+
+// Used for boot UI behavior. On macOS we only start hidden when the OS
+// explicitly launched the app as hidden, not merely "at login".
+export function shouldStartHidden(): boolean {
+  if (process.argv.includes(HIDDEN_FLAG)) return true;
+  if (process.platform === 'darwin') {
+    const settings = app.getLoginItemSettings();
+    return settings.wasOpenedAsHidden;
+  }
+  return false;
+}

surfsense_desktop/src/modules/auto-updater.ts

@@ -1,4 +1,5 @@
 import { app, dialog } from 'electron';
+import { trackEvent } from './analytics';
 
 const SEMVER_RE = /^\d+\.\d+\.\d+/;
 
@@ -17,10 +18,18 @@ export function setupAutoUpdater(): void {
 
   autoUpdater.on('update-available', (info: { version: string }) => {
     console.log(`Update available: ${info.version}`);
+    trackEvent('desktop_update_available', {
+      current_version: version,
+      new_version: info.version,
+    });
   });
 
   autoUpdater.on('update-downloaded', (info: { version: string }) => {
     console.log(`Update downloaded: ${info.version}`);
+    trackEvent('desktop_update_downloaded', {
+      current_version: version,
+      new_version: info.version,
+    });
     dialog.showMessageBox({
       type: 'info',
       buttons: ['Restart', 'Later'],
@@ -29,13 +38,19 @@ export function setupAutoUpdater(): void {
       message: `Version ${info.version} has been downloaded. Restart to apply the update.`,
     }).then(({ response }: { response: number }) => {
       if (response === 0) {
+        trackEvent('desktop_update_install_accepted', { new_version: info.version });
         autoUpdater.quitAndInstall();
+      } else {
+        trackEvent('desktop_update_install_deferred', { new_version: info.version });
       }
     });
   });
 
   autoUpdater.on('error', (err: Error) => {
     console.log('Auto-updater: update check skipped —', err.message?.split('\n')[0]);
+    trackEvent('desktop_update_error', {
+      message: err.message?.split('\n')[0],
+    });
   });
 
   autoUpdater.checkForUpdates().catch(() => {});

surfsense_desktop/src/modules/deep-links.ts

@@ -2,6 +2,7 @@ import { app } from 'electron';
 import path from 'path';
 import { getMainWindow } from './window';
 import { getServerPort } from './server';
+import { trackEvent } from './analytics';
 
 const PROTOCOL = 'surfsense';
 
@@ -16,6 +17,10 @@ function handleDeepLink(url: string) {
   if (!win) return;
 
   const parsed = new URL(url);
+  trackEvent('desktop_deep_link_received', {
+    host: parsed.hostname,
+    path: parsed.pathname,
+  });
   if (parsed.hostname === 'auth' && parsed.pathname === '/callback') {
     const params = parsed.searchParams.toString();
     win.loadURL(`http://localhost:${getServerPort()}/auth/callback?${params}`);
@@ -64,3 +69,10 @@ export function handlePendingDeepLink(): void {
     deepLinkUrl = null;
   }
 }
+
+// True when a deep link arrived before the main window existed. Callers can
+// use this to force-create a window even on a "started hidden" boot, so we
+// don't silently swallow a `surfsense://` URL the user actually clicked on.
+export function hasPendingDeepLink(): boolean {
+  return deepLinkUrl !== null;
+}

surfsense_desktop/src/modules/folder-watcher.ts

@@ -4,6 +4,7 @@ import { randomUUID } from 'crypto';
 import * as path from 'path';
 import * as fs from 'fs';
 import { IPC_CHANNELS } from '../ipc/channels';
+import { trackEvent } from './analytics';
 
 export interface WatchedFolderConfig {
   path: string;
@@ -401,6 +402,15 @@ export async function addWatchedFolder(
     await startWatcher(config);
   }
 
+  trackEvent('desktop_folder_watch_added', {
+    search_space_id: config.searchSpaceId,
+    root_folder_id: config.rootFolderId,
+    active: config.active,
+    has_exclude_patterns: (config.excludePatterns?.length ?? 0) > 0,
+    has_extension_filter: !!config.fileExtensions && config.fileExtensions.length > 0,
+    is_update: existing >= 0,
+  });
+
   return folders;
 }
 
@@ -409,6 +419,7 @@ export async function removeWatchedFolder(
 ): Promise<WatchedFolderConfig[]> {
   const s = await getStore();
   const folders: WatchedFolderConfig[] = s.get(STORE_KEY, []);
+  const removed = folders.find((f: WatchedFolderConfig) => f.path === folderPath);
   const updated = folders.filter((f: WatchedFolderConfig) => f.path !== folderPath);
   s.set(STORE_KEY, updated);
 
@@ -418,6 +429,13 @@ export async function removeWatchedFolder(
   const ms = await getMtimeStore();
   ms.delete(folderPath);
 
+  if (removed) {
+    trackEvent('desktop_folder_watch_removed', {
+      search_space_id: removed.searchSpaceId,
+      root_folder_id: removed.rootFolderId,
+    });
+  }
+
   return updated;
 }
 

surfsense_desktop/src/modules/tray.ts

@@ -2,6 +2,7 @@ import { app, globalShortcut, Menu, nativeImage, Tray } from 'electron';
 import path from 'path';
 import { getMainWindow, createMainWindow } from './window';
 import { getShortcuts } from './shortcuts';
+import { trackEvent } from './analytics';
 
 let tray: Tray | null = null;
 let currentShortcut: string | null = null;
@@ -15,14 +16,16 @@ function getTrayIcon(): nativeImage {
   return img.resize({ width: 16, height: 16 });
 }
 
-function showMainWindow(): void {
-  let win = getMainWindow();
-  if (!win || win.isDestroyed()) {
-    win = createMainWindow('/dashboard');
+function showMainWindow(source: 'tray_click' | 'tray_menu' | 'shortcut' = 'tray_click'): void {
+  const existing = getMainWindow();
+  const reopened = !existing || existing.isDestroyed();
+  if (reopened) {
+    createMainWindow('/dashboard');
   } else {
-    win.show();
-    win.focus();
+    existing.show();
+    existing.focus();
   }
+  trackEvent('desktop_main_window_shown', { source, reopened });
 }
 
 function registerShortcut(accelerator: string): void {
@@ -32,7 +35,7 @@ function registerShortcut(accelerator: string): void {
   }
   if (!accelerator) return;
   try {
-    const ok = globalShortcut.register(accelerator, showMainWindow);
+    const ok = globalShortcut.register(accelerator, () => showMainWindow('shortcut'));
     if (ok) {
       currentShortcut = accelerator;
     } else {
@@ -50,13 +53,19 @@ export async function createTray(): Promise<void> {
   tray.setToolTip('SurfSense');
 
   const contextMenu = Menu.buildFromTemplate([
-    { label: 'Open SurfSense', click: showMainWindow },
+    { label: 'Open SurfSense', click: () => showMainWindow('tray_menu') },
     { type: 'separator' },
-    { label: 'Quit', click: () => { app.exit(0); } },
+    {
+      label: 'Quit',
+      click: () => {
+        trackEvent('desktop_tray_quit_clicked');
+        app.exit(0);
+      },
+    },
   ]);
 
   tray.setContextMenu(contextMenu);
-  tray.on('double-click', showMainWindow);
+  tray.on('double-click', () => showMainWindow('tray_click'));
 
   const shortcuts = await getShortcuts();
   registerShortcut(shortcuts.generalAssist);

surfsense_desktop/src/modules/window.ts

@@ -8,11 +8,18 @@ const isDev = !app.isPackaged;
 const HOSTED_FRONTEND_URL = process.env.HOSTED_FRONTEND_URL as string;
 
 let mainWindow: BrowserWindow | null = null;
+let isQuitting = false;
 
 export function getMainWindow(): BrowserWindow | null {
   return mainWindow;
 }
 
+// Called from main.ts on `before-quit` so the close-to-tray handler knows
+// to actually let the window die instead of hiding it.
+export function markQuitting(): void {
+  isQuitting = true;
+}
+
 export function createMainWindow(initialPath = '/dashboard'): BrowserWindow {
   mainWindow = new BrowserWindow({
     width: 1280,
@@ -70,6 +77,16 @@ export function createMainWindow(initialPath = '/dashboard'): BrowserWindow {
     mainWindow.webContents.openDevTools();
   }
 
+  // Hide-to-tray on close (don't actually destroy the window unless the
+  // user really is quitting). Applies to every instance — including the one
+  // created lazily after a launch-at-login boot.
+  mainWindow.on('close', (e) => {
+    if (!isQuitting && mainWindow) {
+      e.preventDefault();
+      mainWindow.hide();
+    }
+  });
+
   mainWindow.on('closed', () => {
     mainWindow = null;
   });

surfsense_desktop/src/preload.ts

@@ -82,8 +82,23 @@ contextBridge.exposeInMainWorld('electronAPI', {
   setShortcuts: (config: Record<string, string>) =>
     ipcRenderer.invoke(IPC_CHANNELS.SET_SHORTCUTS, config),
 
+  // Launch on system startup
+  getAutoLaunch: () => ipcRenderer.invoke(IPC_CHANNELS.GET_AUTO_LAUNCH),
+  setAutoLaunch: (enabled: boolean, openAsHidden?: boolean) =>
+    ipcRenderer.invoke(IPC_CHANNELS.SET_AUTO_LAUNCH, { enabled, openAsHidden }),
+
   // Active search space
   getActiveSearchSpace: () => ipcRenderer.invoke(IPC_CHANNELS.GET_ACTIVE_SEARCH_SPACE),
   setActiveSearchSpace: (id: string) =>
     ipcRenderer.invoke(IPC_CHANNELS.SET_ACTIVE_SEARCH_SPACE, id),
+
+  // Analytics bridge — lets posthog-js running inside the Next.js renderer
+  // mirror identify/reset/capture into the Electron main-process PostHog
+  // client so desktop-only events are attributed to the logged-in user.
+  analyticsIdentify: (userId: string, properties?: Record<string, unknown>) =>
+    ipcRenderer.invoke(IPC_CHANNELS.ANALYTICS_IDENTIFY, { userId, properties }),
+  analyticsReset: () => ipcRenderer.invoke(IPC_CHANNELS.ANALYTICS_RESET),
+  analyticsCapture: (event: string, properties?: Record<string, unknown>) =>
+    ipcRenderer.invoke(IPC_CHANNELS.ANALYTICS_CAPTURE, { event, properties }),
+  getAnalyticsContext: () => ipcRenderer.invoke(IPC_CHANNELS.ANALYTICS_GET_CONTEXT),
 });

surfsense_web/app/dashboard/[search_space_id]/user-settings/components/DesktopContent.tsx

@@ -1,6 +1,6 @@
 "use client";
 
-import { BrainCog, Rocket, Zap } from "lucide-react";
+import { BrainCog, Power, Rocket, Zap } from "lucide-react";
 import { useEffect, useState } from "react";
 import { toast } from "sonner";
 import { DEFAULT_SHORTCUTS, ShortcutRecorder } from "@/components/desktop/shortcut-recorder";
@@ -30,6 +30,10 @@ export function DesktopContent() {
 	const [searchSpaces, setSearchSpaces] = useState<SearchSpace[]>([]);
 	const [activeSpaceId, setActiveSpaceId] = useState<string | null>(null);
 
+	const [autoLaunchEnabled, setAutoLaunchEnabled] = useState(false);
+	const [autoLaunchHidden, setAutoLaunchHidden] = useState(true);
+	const [autoLaunchSupported, setAutoLaunchSupported] = useState(false);
+
 	useEffect(() => {
 		if (!api) {
 			setLoading(false);
@@ -38,19 +42,28 @@ export function DesktopContent() {
 		}
 
 		let mounted = true;
+		const hasAutoLaunchApi =
+			typeof api.getAutoLaunch === "function" && typeof api.setAutoLaunch === "function";
+		setAutoLaunchSupported(hasAutoLaunchApi);
 
 		Promise.all([
 			api.getAutocompleteEnabled(),
 			api.getShortcuts?.() ?? Promise.resolve(null),
 			api.getActiveSearchSpace?.() ?? Promise.resolve(null),
 			searchSpacesApiService.getSearchSpaces(),
+			hasAutoLaunchApi ? api.getAutoLaunch() : Promise.resolve(null),
 		])
-			.then(([autoEnabled, config, spaceId, spaces]) => {
+			.then(([autoEnabled, config, spaceId, spaces, autoLaunch]) => {
 				if (!mounted) return;
 				setEnabled(autoEnabled);
 				if (config) setShortcuts(config);
 				setActiveSpaceId(spaceId);
 				if (spaces) setSearchSpaces(spaces);
+				if (autoLaunch) {
+					setAutoLaunchEnabled(autoLaunch.enabled);
+					setAutoLaunchHidden(autoLaunch.openAsHidden);
+					setAutoLaunchSupported(autoLaunch.supported);
+				}
 				setLoading(false);
 				setShortcutsLoaded(true);
 			})
@@ -106,6 +119,40 @@ export function DesktopContent() {
 		updateShortcut(key, DEFAULT_SHORTCUTS[key]);
 	};
 
+	const handleAutoLaunchToggle = async (checked: boolean) => {
+		if (!autoLaunchSupported || !api.setAutoLaunch) {
+			toast.error("Please update the desktop app to configure launch on startup");
+			return;
+		}
+		setAutoLaunchEnabled(checked);
+		try {
+			const next = await api.setAutoLaunch(checked, autoLaunchHidden);
+			if (next) {
+				setAutoLaunchEnabled(next.enabled);
+				setAutoLaunchHidden(next.openAsHidden);
+				setAutoLaunchSupported(next.supported);
+			}
+			toast.success(checked ? "SurfSense will launch on startup" : "Launch on startup disabled");
+		} catch {
+			setAutoLaunchEnabled(!checked);
+			toast.error("Failed to update launch on startup");
+		}
+	};
+
+	const handleAutoLaunchHiddenToggle = async (checked: boolean) => {
+		if (!autoLaunchSupported || !api.setAutoLaunch) {
+			toast.error("Please update the desktop app to configure startup behavior");
+			return;
+		}
+		setAutoLaunchHidden(checked);
+		try {
+			await api.setAutoLaunch(autoLaunchEnabled, checked);
+		} catch {
+			setAutoLaunchHidden(!checked);
+			toast.error("Failed to update startup behavior");
+		}
+	};
+
 	const handleSearchSpaceChange = (value: string) => {
 		setActiveSpaceId(value);
 		api.setActiveSearchSpace?.(value);
@@ -145,6 +192,60 @@ export function DesktopContent() {
 				</CardContent>
 			</Card>
 
+			{/* Launch on Startup */}
+			<Card>
+				<CardHeader className="px-3 md:px-6 pt-3 md:pt-6 pb-2 md:pb-3">
+					<CardTitle className="text-base md:text-lg flex items-center gap-2">
+						<Power className="h-4 w-4" />
+						Launch on Startup
+					</CardTitle>
+					<CardDescription className="text-xs md:text-sm">
+						Automatically start SurfSense when you sign in to your computer so global
+						shortcuts and folder sync are always available.
+					</CardDescription>
+				</CardHeader>
+				<CardContent className="px-3 md:px-6 pb-3 md:pb-6 space-y-3">
+					<div className="flex items-center justify-between rounded-lg border p-4">
+						<div className="space-y-0.5">
+							<Label htmlFor="auto-launch-toggle" className="text-sm font-medium cursor-pointer">
+								Open SurfSense at login
+							</Label>
+							<p className="text-xs text-muted-foreground">
+								{autoLaunchSupported
+									? "Adds SurfSense to your system's login items."
+									: "Only available in the packaged desktop app."}
+							</p>
+						</div>
+						<Switch
+							id="auto-launch-toggle"
+							checked={autoLaunchEnabled}
+							onCheckedChange={handleAutoLaunchToggle}
+							disabled={!autoLaunchSupported}
+						/>
+					</div>
+					<div className="flex items-center justify-between rounded-lg border p-4">
+						<div className="space-y-0.5">
+							<Label
+								htmlFor="auto-launch-hidden-toggle"
+								className="text-sm font-medium cursor-pointer"
+							>
+								Start minimized to tray
+							</Label>
+							<p className="text-xs text-muted-foreground">
+								Skip the main window on boot — SurfSense lives in the system tray until you need
+								it.
+							</p>
+						</div>
+						<Switch
+							id="auto-launch-hidden-toggle"
+							checked={autoLaunchHidden}
+							onCheckedChange={handleAutoLaunchHiddenToggle}
+							disabled={!autoLaunchSupported || !autoLaunchEnabled}
+						/>
+					</div>
+				</CardContent>
+			</Card>
+
 			{/* Keyboard Shortcuts */}
 			<Card>
 				<CardHeader className="px-3 md:px-6 pt-3 md:pt-6 pb-2 md:pb-3">

surfsense_web/app/dashboard/[search_space_id]/user-settings/components/PurchaseHistoryContent.tsx

@@ -1,7 +1,8 @@
 "use client";
 
-import { useQuery } from "@tanstack/react-query";
-import { ReceiptText } from "lucide-react";
+import { useQueries } from "@tanstack/react-query";
+import { Coins, FileText, ReceiptText } from "lucide-react";
+import { useMemo } from "react";
 import { Badge } from "@/components/ui/badge";
 import { Spinner } from "@/components/ui/spinner";
 import {
@@ -12,10 +13,26 @@ import {
 	TableHeader,
 	TableRow,
 } from "@/components/ui/table";
-import type { PagePurchase, PagePurchaseStatus } from "@/contracts/types/stripe.types";
+import type {
+	PagePurchase,
+	PagePurchaseStatus,
+	TokenPurchase,
+} from "@/contracts/types/stripe.types";
 import { stripeApiService } from "@/lib/apis/stripe-api.service";
 import { cn } from "@/lib/utils";
 
+type PurchaseKind = "pages" | "tokens";
+
+type UnifiedPurchase = {
+	id: string;
+	kind: PurchaseKind;
+	created_at: string;
+	status: PagePurchaseStatus;
+	granted: number;
+	amount_total: number | null;
+	currency: string | null;
+};
+
 const STATUS_STYLES: Record<PagePurchaseStatus, { label: string; className: string }> = {
 	completed: {
 		label: "Completed",
@@ -31,6 +48,22 @@ const STATUS_STYLES: Record<PagePurchaseStatus, { label: string; className: stri
 	},
 };
 
+const KIND_META: Record<
+	PurchaseKind,
+	{ label: string; icon: React.ComponentType<{ className?: string }>; iconClass: string }
+> = {
+	pages: {
+		label: "Pages",
+		icon: FileText,
+		iconClass: "text-sky-500",
+	},
+	tokens: {
+		label: "Premium Tokens",
+		icon: Coins,
+		iconClass: "text-amber-500",
+	},
+};
+
 function formatDate(iso: string): string {
 	return new Date(iso).toLocaleDateString(undefined, {
 		year: "numeric",
@@ -39,19 +72,65 @@ function formatDate(iso: string): string {
 	});
 }
 
-function formatAmount(purchase: PagePurchase): string {
-	if (purchase.amount_total == null) return "—";
-	const dollars = purchase.amount_total / 100;
-	const currency = (purchase.currency ?? "usd").toUpperCase();
-	return `$${dollars.toFixed(2)} ${currency}`;
+function formatAmount(amount: number | null, currency: string | null): string {
+	if (amount == null) return "—";
+	const dollars = amount / 100;
+	const code = (currency ?? "usd").toUpperCase();
+	return `$${dollars.toFixed(2)} ${code}`;
+}
+
+function normalizePagePurchase(p: PagePurchase): UnifiedPurchase {
+	return {
+		id: p.id,
+		kind: "pages",
+		created_at: p.created_at,
+		status: p.status,
+		granted: p.pages_granted,
+		amount_total: p.amount_total,
+		currency: p.currency,
+	};
+}
+
+function normalizeTokenPurchase(p: TokenPurchase): UnifiedPurchase {
+	return {
+		id: p.id,
+		kind: "tokens",
+		created_at: p.created_at,
+		status: p.status,
+		granted: p.tokens_granted,
+		amount_total: p.amount_total,
+		currency: p.currency,
+	};
 }
 
 export function PurchaseHistoryContent() {
-	const { data, isLoading } = useQuery({
+	const results = useQueries({
+		queries: [
+			{
 				queryKey: ["stripe-purchases"],
 				queryFn: () => stripeApiService.getPurchases(),
+			},
+			{
+				queryKey: ["stripe-token-purchases"],
+				queryFn: () => stripeApiService.getTokenPurchases(),
+			},
+		],
 	});
 
+	const [pagesQuery, tokensQuery] = results;
+	const isLoading = pagesQuery.isLoading || tokensQuery.isLoading;
+
+	const purchases = useMemo<UnifiedPurchase[]>(() => {
+		const pagePurchases = pagesQuery.data?.purchases ?? [];
+		const tokenPurchases = tokensQuery.data?.purchases ?? [];
+		return [
+			...pagePurchases.map(normalizePagePurchase),
+			...tokenPurchases.map(normalizeTokenPurchase),
+		].sort(
+			(a, b) => new Date(b.created_at).getTime() - new Date(a.created_at).getTime()
+		);
+	}, [pagesQuery.data, tokensQuery.data]);
+
 	if (isLoading) {
 		return (
 			<div className="flex items-center justify-center py-12">
@@ -60,15 +139,13 @@ export function PurchaseHistoryContent() {
 		);
 	}
 
-	const purchases = data?.purchases ?? [];
-
 	if (purchases.length === 0) {
 		return (
 			<div className="flex flex-col items-center justify-center gap-2 py-16 text-center">
 				<ReceiptText className="h-8 w-8 text-muted-foreground" />
 				<p className="text-sm font-medium">No purchases yet</p>
 				<p className="text-xs text-muted-foreground">
-					Your page-pack purchases will appear here after checkout.
+					Your page and premium token purchases will appear here after checkout.
 				</p>
 			</div>
 		);
@@ -81,25 +158,36 @@ export function PurchaseHistoryContent() {
 					<TableHeader>
 						<TableRow>
 							<TableHead>Date</TableHead>
-							<TableHead className="text-right">Pages</TableHead>
+							<TableHead>Type</TableHead>
+							<TableHead className="text-right">Granted</TableHead>
 							<TableHead className="text-right">Amount</TableHead>
 							<TableHead className="text-center">Status</TableHead>
 						</TableRow>
 					</TableHeader>
 					<TableBody>
 						{purchases.map((p) => {
-							const style = STATUS_STYLES[p.status];
+							const statusStyle = STATUS_STYLES[p.status];
+							const kind = KIND_META[p.kind];
+							const KindIcon = kind.icon;
 							return (
-								<TableRow key={p.id}>
+								<TableRow key={`${p.kind}-${p.id}`}>
 									<TableCell className="text-sm">{formatDate(p.created_at)}</TableCell>
-									<TableCell className="text-right tabular-nums text-sm">
-										{p.pages_granted.toLocaleString()}
+									<TableCell className="text-sm">
+										<div className="flex items-center gap-2">
+											<KindIcon className={cn("h-4 w-4", kind.iconClass)} />
+											<span>{kind.label}</span>
+										</div>
 									</TableCell>
 									<TableCell className="text-right tabular-nums text-sm">
-										{formatAmount(p)}
+										{p.granted.toLocaleString()}
+									</TableCell>
+									<TableCell className="text-right tabular-nums text-sm">
+										{formatAmount(p.amount_total, p.currency)}
 									</TableCell>
 									<TableCell className="text-center">
-										<Badge className={cn("text-[10px]", style.className)}>{style.label}</Badge>
+										<Badge className={cn("text-[10px]", statusStyle.className)}>
+											{statusStyle.label}
+										</Badge>
 									</TableCell>
 								</TableRow>
 							);
@@ -108,7 +196,8 @@ export function PurchaseHistoryContent() {
 				</Table>
 			</div>
 			<p className="text-center text-xs text-muted-foreground">
-				Showing your {purchases.length} most recent purchase{purchases.length !== 1 ? "s" : ""}.
+				Showing your {purchases.length} most recent purchase
+				{purchases.length !== 1 ? "s" : ""}.
 			</p>
 		</div>
 	);

surfsense_web/components/assistant-ui/connector-popup/constants/connector-constants.ts

@@ -340,5 +340,85 @@ export const AUTO_INDEX_DEFAULTS: Record<string, AutoIndexConfig> = {
 
 export const AUTO_INDEX_CONNECTOR_TYPES = new Set<string>(Object.keys(AUTO_INDEX_DEFAULTS));
 
+// ============================================================================
+// CONNECTOR TELEMETRY REGISTRY
+// ----------------------------------------------------------------------------
+// Single source of truth for "what does this connector_type look like in
+// analytics?". Any connector added to the lists above is automatically
+// picked up here, so adding a new integration does NOT require touching
+// `lib/posthog/events.ts` or per-connector tracking code.
+// ============================================================================
+
+export type ConnectorTelemetryGroup =
+	| "oauth"
+	| "composio"
+	| "crawler"
+	| "other"
+	| "unknown";
+
+export interface ConnectorTelemetryMeta {
+	connector_type: string;
+	connector_title: string;
+	connector_group: ConnectorTelemetryGroup;
+	is_oauth: boolean;
+}
+
+const CONNECTOR_TELEMETRY_REGISTRY: ReadonlyMap<string, ConnectorTelemetryMeta> =
+	(() => {
+		const map = new Map<string, ConnectorTelemetryMeta>();
+
+		for (const c of OAUTH_CONNECTORS) {
+			map.set(c.connectorType, {
+				connector_type: c.connectorType,
+				connector_title: c.title,
+				connector_group: "oauth",
+				is_oauth: true,
+			});
+		}
+		for (const c of COMPOSIO_CONNECTORS) {
+			map.set(c.connectorType, {
+				connector_type: c.connectorType,
+				connector_title: c.title,
+				connector_group: "composio",
+				is_oauth: true,
+			});
+		}
+		for (const c of CRAWLERS) {
+			map.set(c.connectorType, {
+				connector_type: c.connectorType,
+				connector_title: c.title,
+				connector_group: "crawler",
+				is_oauth: false,
+			});
+		}
+		for (const c of OTHER_CONNECTORS) {
+			map.set(c.connectorType, {
+				connector_type: c.connectorType,
+				connector_title: c.title,
+				connector_group: "other",
+				is_oauth: false,
+			});
+		}
+
+		return map;
+	})();
+
+/**
+ * Returns telemetry metadata for a connector_type, or a minimal "unknown"
+ * record so tracking never no-ops for connectors that exist in the backend
+ * but were forgotten in the UI registry.
+ */
+export function getConnectorTelemetryMeta(connectorType: string): ConnectorTelemetryMeta {
+	const hit = CONNECTOR_TELEMETRY_REGISTRY.get(connectorType);
+	if (hit) return hit;
+
+	return {
+		connector_type: connectorType,
+		connector_title: connectorType,
+		connector_group: "unknown",
+		is_oauth: false,
+	};
+}
+
 // Re-export IndexingConfigState from schemas for backward compatibility
 export type { IndexingConfigState } from "./connector-popup.schemas";

surfsense_web/components/assistant-ui/connector-popup/hooks/use-connector-dialog.ts

@@ -24,6 +24,8 @@ import { isSelfHosted } from "@/lib/env-config";
 import {
 	trackConnectorConnected,
 	trackConnectorDeleted,
+	trackConnectorSetupFailure,
+	trackConnectorSetupStarted,
 	trackIndexWithDateRangeOpened,
 	trackIndexWithDateRangeStarted,
 	trackPeriodicIndexingStarted,
@@ -232,10 +234,20 @@ export const useConnectorDialog = () => {
 
 		if (result.error) {
 			const oauthConnector = result.connector
-				? OAUTH_CONNECTORS.find((c) => c.id === result.connector)
+				? OAUTH_CONNECTORS.find((c) => c.id === result.connector) ||
+					COMPOSIO_CONNECTORS.find((c) => c.id === result.connector)
 				: null;
 			const name = oauthConnector?.title || "connector";
 
+			if (oauthConnector) {
+				trackConnectorSetupFailure(
+					Number(searchSpaceId),
+					oauthConnector.connectorType,
+					result.error,
+					"oauth_callback"
+				);
+			}
+
 			if (result.error === "duplicate_account") {
 				toast.error(`This ${name} account is already connected`, {
 					description: "Please use a different account or manage the existing connection.",
@@ -348,6 +360,12 @@ export const useConnectorDialog = () => {
 			// Set connecting state immediately to disable button and show spinner
 			setConnectingId(connector.id);
 
+			trackConnectorSetupStarted(
+				Number(searchSpaceId),
+				connector.connectorType,
+				"oauth_click"
+			);
+
 			try {
 				// Check if authEndpoint already has query parameters
 				const separator = connector.authEndpoint.includes("?") ? "&" : "?";
@@ -369,6 +387,12 @@ export const useConnectorDialog = () => {
 				window.location.href = validatedData.auth_url;
 			} catch (error) {
 				console.error(`Error connecting to ${connector.title}:`, error);
+				trackConnectorSetupFailure(
+					Number(searchSpaceId),
+					connector.connectorType,
+					error instanceof Error ? error.message : "oauth_initiation_failed",
+					"oauth_init"
+				);
 				if (error instanceof Error && error.message.includes("Invalid auth URL")) {
 					toast.error(`Invalid response from ${connector.title} OAuth endpoint`);
 				} else {
@@ -392,6 +416,11 @@ export const useConnectorDialog = () => {
 		if (!searchSpaceId) return;
 
 		setConnectingId("webcrawler-connector");
+		trackConnectorSetupStarted(
+			Number(searchSpaceId),
+			EnumConnectorName.WEBCRAWLER_CONNECTOR,
+			"webcrawler_quick_add"
+		);
 		try {
 			await createConnector({
 				data: {
@@ -441,6 +470,12 @@ export const useConnectorDialog = () => {
 			}
 		} catch (error) {
 			console.error("Error creating webcrawler connector:", error);
+			trackConnectorSetupFailure(
+				Number(searchSpaceId),
+				EnumConnectorName.WEBCRAWLER_CONNECTOR,
+				error instanceof Error ? error.message : "webcrawler_create_failed",
+				"webcrawler_quick_add"
+			);
 			toast.error("Failed to create web crawler connector");
 		} finally {
 			setConnectingId(null);
@@ -452,6 +487,12 @@ export const useConnectorDialog = () => {
 		(connectorType: string) => {
 			if (!searchSpaceId) return;
 
+			trackConnectorSetupStarted(
+				Number(searchSpaceId),
+				connectorType,
+				"non_oauth_click"
+			);
+
 			// Handle Obsidian specifically on Desktop & Cloud
 			if (connectorType === EnumConnectorName.OBSIDIAN_CONNECTOR && !selfHosted && isDesktop) {
 				setIsOpen(false);
@@ -680,6 +721,12 @@ export const useConnectorDialog = () => {
 				}
 			} catch (error) {
 				console.error("Error creating connector:", error);
+				trackConnectorSetupFailure(
+					Number(searchSpaceId),
+					connectingConnectorType ?? formData.connector_type,
+					error instanceof Error ? error.message : "connector_create_failed",
+					"non_oauth_form"
+				);
 				toast.error(error instanceof Error ? error.message : "Failed to create connector");
 			} finally {
 				isCreatingConnectorRef.current = false;

surfsense_web/components/free-chat/anonymous-chat.tsx

@@ -5,6 +5,7 @@ import { useCallback, useEffect, useRef, useState } from "react";
 import type { AnonModel, AnonQuotaResponse } from "@/contracts/types/anonymous-chat.types";
 import { anonymousChatApiService } from "@/lib/apis/anonymous-chat-api.service";
 import { readSSEStream } from "@/lib/chat/streaming-state";
+import { trackAnonymousChatMessageSent } from "@/lib/posthog/events";
 import { cn } from "@/lib/utils";
 import { QuotaBar } from "./quota-bar";
 import { QuotaWarningBanner } from "./quota-warning-banner";
@@ -61,6 +62,12 @@ export function AnonymousChat({ model }: AnonymousChatProps) {
 			textareaRef.current.style.height = "auto";
 		}
 
+		trackAnonymousChatMessageSent({
+			modelSlug: model.seo_slug,
+			messageLength: trimmed.length,
+			surface: "free_model_page",
+		});
+
 		const controller = new AbortController();
 		abortRef.current = controller;
 

surfsense_web/components/free-chat/free-chat-page.tsx

@@ -28,6 +28,7 @@ import {
 	updateToolCall,
 } from "@/lib/chat/streaming-state";
 import { BACKEND_URL } from "@/lib/env-config";
+import { trackAnonymousChatMessageSent } from "@/lib/posthog/events";
 import { FreeModelSelector } from "./free-model-selector";
 import { FreeThread } from "./free-thread";
 
@@ -206,6 +207,14 @@ export function FreeChatPage() {
 			}
 			if (!userQuery.trim()) return;
 
+			trackAnonymousChatMessageSent({
+				modelSlug,
+				messageLength: userQuery.trim().length,
+				hasUploadedDoc:
+					anonMode.isAnonymous && anonMode.uploadedDoc !== null ? true : false,
+				surface: "free_chat_page",
+			});
+
 			const userMsgId = `msg-user-${Date.now()}`;
 			setMessages((prev) => [
 				...prev,

surfsense_web/contracts/types/stripe.types.ts

@@ -49,6 +49,8 @@ export const tokenStripeStatusResponse = z.object({
 	premium_tokens_remaining: z.number().default(0),
 });
 
+export const tokenPurchaseStatusEnum = pagePurchaseStatusEnum;
+
 export const tokenPurchase = z.object({
 	id: z.uuid(),
 	stripe_checkout_session_id: z.string(),
@@ -57,7 +59,7 @@ export const tokenPurchase = z.object({
 	tokens_granted: z.number(),
 	amount_total: z.number().nullable(),
 	currency: z.string().nullable(),
-	status: z.string(),
+	status: tokenPurchaseStatusEnum,
 	completed_at: z.string().nullable(),
 	created_at: z.string(),
 });
@@ -75,5 +77,6 @@ export type GetPagePurchasesResponse = z.infer<typeof getPagePurchasesResponse>;
 export type CreateTokenCheckoutSessionRequest = z.infer<typeof createTokenCheckoutSessionRequest>;
 export type CreateTokenCheckoutSessionResponse = z.infer<typeof createTokenCheckoutSessionResponse>;
 export type TokenStripeStatusResponse = z.infer<typeof tokenStripeStatusResponse>;
+export type TokenPurchaseStatus = z.infer<typeof tokenPurchaseStatusEnum>;
 export type TokenPurchase = z.infer<typeof tokenPurchase>;
 export type GetTokenPurchasesResponse = z.infer<typeof getTokenPurchasesResponse>;

surfsense_web/instrumentation-client.ts

@@ -1,18 +1,65 @@
 import posthog from "posthog-js";
 
-function initPostHog() {
+/**
+ * PostHog initialisation for the Next.js renderer.
+ *
+ * The same bundle ships in two contexts:
+ *   1. A normal browser session on surfsense.com  -> platform = "web"
+ *   2. The Electron desktop app (renders the Next app from localhost)
+ *      -> platform = "desktop"
+ *
+ * When running inside Electron we also seed `posthog-js` with the main
+ * process's machine distinctId so that events fired from both the renderer
+ * (e.g. `chat_message_sent`, page views) and the Electron main process
+ * (e.g. `desktop_quick_ask_opened`) share a single PostHog person before
+ * login, and can be merged into the authenticated user afterwards.
+ */
+
+function isElectron(): boolean {
+	return typeof window !== "undefined" && !!window.electronAPI;
+}
+
+function currentPlatform(): "desktop" | "web" {
+	return isElectron() ? "desktop" : "web";
+}
+
+async function resolveBootstrapDistinctId(): Promise<string | undefined> {
+	if (!isElectron() || !window.electronAPI?.getAnalyticsContext) return undefined;
+	try {
+		const ctx = await window.electronAPI.getAnalyticsContext();
+		return ctx?.machineId || ctx?.distinctId || undefined;
+	} catch {
+		return undefined;
+	}
+}
+
+async function initPostHog() {
 	try {
 		if (!process.env.NEXT_PUBLIC_POSTHOG_KEY) return;
 
+		const platform = currentPlatform();
+		const bootstrapDistinctId = await resolveBootstrapDistinctId();
+
 		posthog.init(process.env.NEXT_PUBLIC_POSTHOG_KEY, {
 			api_host: "https://assets.surfsense.com",
 			ui_host: "https://us.posthog.com",
 			defaults: "2026-01-30",
 			capture_pageview: "history_change",
 			capture_pageleave: true,
+			...(bootstrapDistinctId
+				? {
+						bootstrap: {
+							distinctID: bootstrapDistinctId,
+							isIdentifiedID: false,
+						},
+					}
+				: {}),
 			before_send: (event) => {
 				if (event?.properties) {
-					event.properties.platform = "web";
+					event.properties.platform = platform;
+					if (platform === "desktop") {
+						event.properties.is_desktop = true;
+					}
 
 					const params = new URLSearchParams(window.location.search);
 					const ref = params.get("ref");
@@ -30,9 +77,14 @@ function initPostHog() {
 
 					event.properties.$set = {
 						...event.properties.$set,
-						platform: "web",
+						platform,
 						last_seen_at: new Date().toISOString(),
 					};
+
+					event.properties.$set_once = {
+						...event.properties.$set_once,
+						first_seen_platform: platform,
+					};
 				}
 				return event;
 			},
@@ -51,8 +103,12 @@ if (typeof window !== "undefined") {
 	window.posthog = posthog;
 
 	if ("requestIdleCallback" in window) {
-		requestIdleCallback(initPostHog);
+		requestIdleCallback(() => {
+			void initPostHog();
+		});
 	} else {
-		setTimeout(initPostHog, 3500);
+		setTimeout(() => {
+			void initPostHog();
+		}, 3500);
 	}
 }

surfsense_web/lib/posthog/events.ts

@@ -1,4 +1,5 @@
 import posthog from "posthog-js";
+import { getConnectorTelemetryMeta } from "@/components/assistant-ui/connector-popup/constants/connector-constants";
 
 /**
  * PostHog Analytics Event Definitions
@@ -13,8 +14,8 @@ import posthog from "posthog-js";
  * - auth: Authentication events
  * - search_space: Search space management
  * - document: Document management
- * - chat: Chat and messaging
- * - connector: External connector events
+ * - chat: Chat and messaging (authenticated + anonymous)
+ * - connector: External connector events (all lifecycle stages)
  * - contact: Contact form events
  * - settings: Settings changes
  * - marketing: Marketing/referral tracking
@@ -28,6 +29,17 @@ function safeCapture(event: string, properties?: Record<string, unknown>) {
 	}
 }
 
+/**
+ * Drop undefined values so PostHog doesn't log `"foo": undefined` noise.
+ */
+function compact<T extends Record<string, unknown>>(obj: T): Record<string, unknown> {
+	const out: Record<string, unknown> = {};
+	for (const [k, v] of Object.entries(obj)) {
+		if (v !== undefined) out[k] = v;
+	}
+	return out;
+}
+
 // ============================================
 // AUTH EVENTS
 // ============================================
@@ -127,6 +139,28 @@ export function trackChatError(searchSpaceId: number, chatId: number, error?: st
 	});
 }
 
+/**
+ * Track a message sent from the unauthenticated "free" / anonymous chat
+ * flow. This is intentionally a separate event from `chat_message_sent`
+ * so WAU / retention queries on the authenticated event stay clean while
+ * still giving us visibility into top-of-funnel usage on /free/*.
+ */
+export function trackAnonymousChatMessageSent(options: {
+	modelSlug: string;
+	messageLength?: number;
+	hasUploadedDoc?: boolean;
+	webSearchEnabled?: boolean;
+	surface?: "free_chat_page" | "free_model_page";
+}) {
+	safeCapture("anonymous_chat_message_sent", {
+		model_slug: options.modelSlug,
+		message_length: options.messageLength,
+		has_uploaded_doc: options.hasUploadedDoc ?? false,
+		web_search_enabled: options.webSearchEnabled,
+		surface: options.surface,
+	});
+}
+
 // ============================================
 // DOCUMENT EVENTS
 // ============================================
@@ -179,37 +213,88 @@ export function trackYouTubeImport(searchSpaceId: number, url: string) {
 }
 
 // ============================================
-// CONNECTOR EVENTS
+// CONNECTOR EVENTS (generic lifecycle dispatcher)
 // ============================================
+//
+// All connector events go through `trackConnectorEvent`. The connector's
+// human-readable title and its group (oauth/composio/crawler/other) are
+// auto-attached from the shared registry in `connector-constants.ts`, so
+// adding a new connector to that list is the only change required for it
+// to show up correctly in PostHog dashboards.
 
-export function trackConnectorSetupStarted(searchSpaceId: number, connectorType: string) {
-	safeCapture("connector_setup_started", {
-		search_space_id: searchSpaceId,
-		connector_type: connectorType,
+export type ConnectorEventStage =
+	| "setup_started"
+	| "setup_success"
+	| "setup_failure"
+	| "oauth_initiated"
+	| "connected"
+	| "deleted"
+	| "synced";
+
+export interface ConnectorEventOptions {
+	searchSpaceId?: number | null;
+	connectorId?: number | null;
+	/** Source of the action (e.g. "oauth_callback", "non_oauth_form", "webcrawler_quick_add"). */
+	source?: string;
+	/** Free-form error message for failure events. */
+	error?: string;
+	/** Extra properties specific to the stage (e.g. frequency_minutes for sync events). */
+	extra?: Record<string, unknown>;
+}
+
+/**
+ * Generic connector lifecycle tracker. Every connector analytics event
+ * should funnel through here so the enrichment stays consistent.
+ */
+export function trackConnectorEvent(
+	stage: ConnectorEventStage,
+	connectorType: string,
+	options: ConnectorEventOptions = {}
+) {
+	const meta = getConnectorTelemetryMeta(connectorType);
+	safeCapture(`connector_${stage}`, {
+		...compact({
+			search_space_id: options.searchSpaceId ?? undefined,
+			connector_id: options.connectorId ?? undefined,
+			source: options.source,
+			error: options.error,
+		}),
+		connector_type: meta.connector_type,
+		connector_title: meta.connector_title,
+		connector_group: meta.connector_group,
+		is_oauth: meta.is_oauth,
+		...(options.extra ?? {}),
 	});
 }
 
+// ---- Convenience wrappers kept for backward compatibility ----
+
+export function trackConnectorSetupStarted(
+	searchSpaceId: number,
+	connectorType: string,
+	source?: string
+) {
+	trackConnectorEvent("setup_started", connectorType, { searchSpaceId, source });
+}
+
 export function trackConnectorSetupSuccess(
 	searchSpaceId: number,
 	connectorType: string,
 	connectorId: number
 ) {
-	safeCapture("connector_setup_success", {
-		search_space_id: searchSpaceId,
-		connector_type: connectorType,
-		connector_id: connectorId,
-	});
+	trackConnectorEvent("setup_success", connectorType, { searchSpaceId, connectorId });
 }
 
 export function trackConnectorSetupFailure(
-	searchSpaceId: number,
+	searchSpaceId: number | null | undefined,
 	connectorType: string,
-	error?: string
+	error?: string,
+	source?: string
 ) {
-	safeCapture("connector_setup_failure", {
-		search_space_id: searchSpaceId,
-		connector_type: connectorType,
+	trackConnectorEvent("setup_failure", connectorType, {
+		searchSpaceId: searchSpaceId ?? undefined,
 		error,
+		source,
 	});
 }
 
@@ -218,11 +303,7 @@ export function trackConnectorDeleted(
 	connectorType: string,
 	connectorId: number
 ) {
-	safeCapture("connector_deleted", {
-		search_space_id: searchSpaceId,
-		connector_type: connectorType,
-		connector_id: connectorId,
-	});
+	trackConnectorEvent("deleted", connectorType, { searchSpaceId, connectorId });
 }
 
 export function trackConnectorSynced(
@@ -230,11 +311,7 @@ export function trackConnectorSynced(
 	connectorType: string,
 	connectorId: number
 ) {
-	safeCapture("connector_synced", {
-		search_space_id: searchSpaceId,
-		connector_type: connectorType,
-		connector_id: connectorId,
-	});
+	trackConnectorEvent("synced", connectorType, { searchSpaceId, connectorId });
 }
 
 // ============================================
@@ -345,10 +422,9 @@ export function trackConnectorConnected(
 	connectorType: string,
 	connectorId?: number
 ) {
-	safeCapture("connector_connected", {
-		search_space_id: searchSpaceId,
-		connector_type: connectorType,
-		connector_id: connectorId,
+	trackConnectorEvent("connected", connectorType, {
+		searchSpaceId,
+		connectorId: connectorId ?? undefined,
 	});
 }
 
@@ -467,8 +543,13 @@ export function trackReferralLanding(refCode: string, landingUrl: string) {
 // ============================================
 
 /**
- * Identify a user for PostHog analytics
- * Call this after successful authentication
+ * Identify a user for PostHog analytics.
+ * Call this after successful authentication.
+ *
+ * In the Electron desktop app the same call is mirrored into the
+ * main-process PostHog client so desktop-only events (e.g.
+ * `desktop_quick_ask_opened`, `desktop_autocomplete_accepted`) are
+ * attributed to the logged-in user rather than an anonymous machine ID.
  */
 export function identifyUser(userId: string, properties?: Record<string, unknown>) {
 	try {
@@ -476,10 +557,19 @@ export function identifyUser(userId: string, properties?: Record<string, unknown
 	} catch {
 		// Silently ignore – ad-blockers may break posthog
 	}
+
+	try {
+		if (typeof window !== "undefined" && window.electronAPI?.analyticsIdentify) {
+			void window.electronAPI.analyticsIdentify(userId, properties);
+		}
+	} catch {
+		// IPC errors must never break the app
+	}
 }
 
 /**
- * Reset user identity (call on logout)
+ * Reset user identity (call on logout). Mirrors the reset into the
+ * Electron main process when running inside the desktop app.
  */
 export function resetUser() {
 	try {
@@ -487,4 +577,12 @@ export function resetUser() {
 	} catch {
 		// Silently ignore – ad-blockers may break posthog
 	}
+
+	try {
+		if (typeof window !== "undefined" && window.electronAPI?.analyticsReset) {
+			void window.electronAPI.analyticsReset();
+		}
+	} catch {
+		// IPC errors must never break the app
+	}
 }

surfsense_web/types/window.d.ts

@@ -102,9 +102,29 @@ interface ElectronAPI {
 	setShortcuts: (
 		config: Partial<{ generalAssist: string; quickAsk: string; autocomplete: string }>
 	) => Promise<{ generalAssist: string; quickAsk: string; autocomplete: string }>;
+	// Launch on system startup
+	getAutoLaunch: () => Promise<{
+		enabled: boolean;
+		openAsHidden: boolean;
+		supported: boolean;
+	}>;
+	setAutoLaunch: (
+		enabled: boolean,
+		openAsHidden?: boolean
+	) => Promise<{ enabled: boolean; openAsHidden: boolean; supported: boolean }>;
 	// Active search space
 	getActiveSearchSpace: () => Promise<string | null>;
 	setActiveSearchSpace: (id: string) => Promise<void>;
+	// Analytics bridge (PostHog mirror into the Electron main process)
+	analyticsIdentify: (userId: string, properties?: Record<string, unknown>) => Promise<void>;
+	analyticsReset: () => Promise<void>;
+	analyticsCapture: (event: string, properties?: Record<string, unknown>) => Promise<void>;
+	getAnalyticsContext: () => Promise<{
+		distinctId: string;
+		machineId: string;
+		appVersion: string;
+		platform: string;
+	}>;
 }
 
 declare global {