Add Apple Music, Last.fm sign-in, and a fallback for Spotify's account cap

- Apple Music: sign MusicKit developer tokens (ES256 via node:crypto),
  accept the Music User Token from the iOS app, and poll recently played.
  Apple has no now-playing API or play timestamps, so a new top song is
  shown as playing for its length; connecting records a baseline so an
  old song isn't announced as current
- Last.fm web auth ("Sign in with Last.fm") instead of typing a
  username; session key stored encrypted
- Spotify accounts rejected by the 5-user development cap are sent back
  with error=spotify_limited instead of a 500, so apps can offer
  Spotify via Last.fm

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_01MzFywujuH9TiuXbr9vjoX8

apps/api/.env.example

@@ -15,9 +15,16 @@ SPOTIFY_CLIENT_ID=
 SPOTIFY_CLIENT_SECRET=
 # https://www.last.fm/api/account/create
 LASTFM_API_KEY=
+# Shared secret from the same Last.fm API account; enables one-tap "Sign in with Last.fm"
+LASTFM_SHARED_SECRET=
 # song.link API key (request at https://odesli.co). Enables YouTube Music/TIDAL links; without it those fall back to search.
 ODESLI_API_KEY=
 # Stable identifier for this app in Plex's auth flow
 PLEX_CLIENT_ID=musicshare-dev
 # Let users connect Jellyfin/Plex servers on private networks (LAN). Never enable in a hosted deployment.
 ALLOW_PRIVATE_SERVER_URLS=false
+# Apple Music: Apple Developer → Certificates, IDs & Profiles → Keys → new key with MusicKit enabled.
+# Paste the .p8 contents with newlines as \n.
+APPLE_TEAM_ID=
+APPLE_MUSICKIT_KEY_ID=
+APPLE_MUSICKIT_PRIVATE_KEY=

apps/api/src/env.ts

@@ -23,7 +23,13 @@ const schema = z.object({
   SPOTIFY_CLIENT_ID: optional,
   SPOTIFY_CLIENT_SECRET: optional,
   LASTFM_API_KEY: optional,
+  /** Enables "Sign in with Last.fm" (web auth). Without it, users type their username. */
+  LASTFM_SHARED_SECRET: optional,
   ODESLI_API_KEY: optional,
+  /** Apple Music (MusicKit): Team ID, MusicKit key ID, and the key's .p8 contents (newlines may be written as \n). */
+  APPLE_TEAM_ID: optional,
+  APPLE_MUSICKIT_KEY_ID: optional,
+  APPLE_MUSICKIT_PRIVATE_KEY: optional,
   /** Identifies this app to Plex. Keep it stable: changing it invalidates users' Plex authorizations. */
   PLEX_CLIENT_ID: z.string().default('musicshare-dev'),
   /**
@@ -40,3 +46,4 @@ const schema = z.object({
 export const env = schema.parse(process.env);
 
 export const spotifyConfigured = Boolean(env.SPOTIFY_CLIENT_ID && env.SPOTIFY_CLIENT_SECRET);
+export const appleMusicConfigured = Boolean(env.APPLE_TEAM_ID && env.APPLE_MUSICKIT_KEY_ID && env.APPLE_MUSICKIT_PRIVATE_KEY);

apps/api/src/lib/appleMusic.ts

@@ -0,0 +1,71 @@
+/**
+ * Apple Music API access. Requests need two tokens: a developer token (a JWT
+ * we sign with the MusicKit key) and the user's Music User Token, which the
+ * iOS app obtains from the system "Allow access to Apple Music" prompt.
+ */
+import { createPrivateKey, sign } from 'node:crypto';
+import { env } from '../env';
+import { HttpError } from './http';
+
+const API = 'https://api.music.apple.com/v1';
+/** Apple allows up to ~6 months; shorter limits the damage if a token leaks. */
+const TOKEN_TTL_SECONDS = 30 * 86_400;
+
+let cached: { token: string; expiresAt: number } | null = null;
+
+const b64url = (input: Buffer | string) => Buffer.from(input).toString('base64url');
+
+/** Signed ES256 developer token, cached until a day before it expires. */
+export function appleDeveloperToken(now = Date.now()): string {
+  if (cached && cached.expiresAt - now > 86_400_000) return cached.token;
+  if (!env.APPLE_TEAM_ID || !env.APPLE_MUSICKIT_KEY_ID || !env.APPLE_MUSICKIT_PRIVATE_KEY) {
+    throw new HttpError(501, 'Apple Music is not configured on this server');
+  }
+  const iat = Math.floor(now / 1000);
+  const header = b64url(JSON.stringify({ alg: 'ES256', kid: env.APPLE_MUSICKIT_KEY_ID }));
+  const payload = b64url(JSON.stringify({ iss: env.APPLE_TEAM_ID, iat, exp: iat + TOKEN_TTL_SECONDS }));
+  const key = createPrivateKey(env.APPLE_MUSICKIT_PRIVATE_KEY.replace(/\\n/g, '\n'));
+  // JWS wants the raw r||s signature, not DER.
+  const signature = sign('sha256', Buffer.from(`${header}.${payload}`), { key, dsaEncoding: 'ieee-p1363' });
+  const token = `${header}.${payload}.${b64url(signature)}`;
+  cached = { token, expiresAt: (iat + TOKEN_TTL_SECONDS) * 1000 };
+  return token;
+}
+
+/** Thrown when Apple rejects the Music User Token (expired after ~6 months, or access revoked). */
+export class AppleUserTokenError extends Error {}
+
+export async function appleMusicGet<T>(path: string, musicUserToken: string): Promise<T> {
+  const res = await fetch(`${API}${path}`, {
+    headers: { Authorization: `Bearer ${appleDeveloperToken()}`, 'Music-User-Token': musicUserToken },
+    signal: AbortSignal.timeout(8000),
+  });
+  if (res.status === 401 || res.status === 403) throw new AppleUserTokenError(`Apple Music ${res.status}`);
+  if (!res.ok) throw new HttpError(res.status, `Apple Music ${res.status}`);
+  return (await res.json()) as T;
+}
+
+export interface AppleSong {
+  id: string;
+  type: string; // songs | library-songs | music-videos ...
+  attributes?: {
+    name: string;
+    artistName: string;
+    albumName?: string;
+    durationInMillis?: number;
+    isrc?: string;
+    url?: string;
+    artwork?: { url: string };
+  };
+}
+
+export const recentlyPlayed = (musicUserToken: string, limit = 1) =>
+  appleMusicGet<{ data: AppleSong[] }>(`/me/recent/played/tracks?limit=${limit}`, musicUserToken);
+
+export const storefront = (musicUserToken: string) =>
+  appleMusicGet<{ data: { id: string; attributes?: { name: string } }[] }>('/me/storefront', musicUserToken);
+
+/** Test hook: forget the cached developer token. */
+export const resetAppleTokenCache = () => {
+  cached = null;
+};

apps/api/src/providers/appleMusic.ts

@@ -0,0 +1,70 @@
+/**
+ * Apple Music has no "now playing" endpoint, only recently played (no
+ * timestamps). We remember the newest item; when it changes, that song is
+ * shown as "listening now" for its duration. The connection starts from a
+ * baseline so an old last-played song isn't announced as current.
+ * The iOS app adds exact live updates while it's open (device reports).
+ */
+import { eq } from 'drizzle-orm';
+import { db, schema } from '../db';
+import type { Connection } from '../db/schema';
+import { AppleUserTokenError, recentlyPlayed, type AppleSong } from '../lib/appleMusic';
+import { decrypt } from '../lib/crypto';
+import { ProviderAuthError, type IncomingTrack, type PollingProvider } from './types';
+
+export interface AppleMusicMeta {
+  storefront?: string;
+  lastSeenId?: string | null;
+  lastSeenAt?: number;
+}
+
+/** Without a duration, assume a typical song length. */
+const DEFAULT_DURATION_MS = 4 * 60_000;
+const GRACE_MS = 30_000;
+
+export function toIncomingTrack(song: AppleSong): IncomingTrack | null {
+  const a = song.attributes;
+  if (!a?.name) return null;
+  const isCatalog = song.type === 'songs';
+  return {
+    title: a.name,
+    artist: a.artistName || 'Unknown artist',
+    album: a.albumName ?? null,
+    durationMs: a.durationInMillis ?? null,
+    isrc: a.isrc ?? null,
+    artworkUrl: a.artwork?.url.replace('{w}', '600').replace('{h}', '600') ?? null,
+    // Library uploads have no catalog page to link to.
+    links: isCatalog && a.url ? { apple_music: { id: song.id, url: a.url } } : undefined,
+  };
+}
+
+export const appleMusicProvider: PollingProvider = {
+  id: 'apple_music',
+  async poll(conn: Connection) {
+    const meta = conn.meta as AppleMusicMeta;
+    let latest: AppleSong | undefined;
+    try {
+      latest = (await recentlyPlayed(decrypt(conn.accessTokenEnc!))).data[0];
+    } catch (err) {
+      if (err instanceof AppleUserTokenError) throw new ProviderAuthError('Apple Music access expired or was revoked');
+      throw err;
+    }
+    if (!latest) return null;
+
+    const now = Date.now();
+    if (latest.id !== meta.lastSeenId) {
+      await db
+        .update(schema.connections)
+        .set({ meta: { ...meta, lastSeenId: latest.id, lastSeenAt: now } })
+        .where(eq(schema.connections.id, conn.id));
+      const track = toIncomingTrack(latest);
+      return track ? { track, isPlaying: true, progressMs: null } : null;
+    }
+
+    // Same song as last time: keep it "playing" until it would have finished.
+    const track = toIncomingTrack(latest);
+    const duration = latest.attributes?.durationInMillis ?? DEFAULT_DURATION_MS;
+    if (!track || !meta.lastSeenAt || now - meta.lastSeenAt > duration + GRACE_MS) return null;
+    return { track, isPlaying: true, progressMs: now - meta.lastSeenAt };
+  },
+};

apps/api/src/providers/index.ts

@@ -1,4 +1,5 @@
 import type { NowPlayingProvider } from '@musicshare/shared';
+import { appleMusicProvider } from './appleMusic';
 import { jellyfinProvider } from './jellyfin';
 import { lastfmProvider } from './lastfm';
 import { listenbrainzProvider } from './listenbrainz';
@@ -13,6 +14,7 @@ export const pollingProviders: Partial<Record<NowPlayingProvider, PollingProvide
   listenbrainz: listenbrainzProvider,
   plex: plexProvider,
   jellyfin: jellyfinProvider,
+  apple_music: appleMusicProvider,
 };
 
 export const POLLED_PROVIDERS = Object.keys(pollingProviders) as NowPlayingProvider[];

apps/api/src/providers/lastfm.ts

@@ -1,3 +1,4 @@
+import { createHash } from 'node:crypto';
 import { env } from '../env';
 import { HttpError, fetchJson } from '../lib/http';
 import { ProviderAuthError, type PollingProvider } from './types';
@@ -13,6 +14,28 @@ interface LastfmTrack {
 const api = (params: Record<string, string>) =>
   `https://ws.audioscrobbler.com/2.0/?${new URLSearchParams({ ...params, api_key: env.LASTFM_API_KEY!, format: 'json' })}`;
 
+/** Last.fm web auth: send the user here; Last.fm redirects back to `callbackUrl` with ?token=…/&token=… */
+export const lastfmAuthUrl = (callbackUrl: string) =>
+  `https://www.last.fm/api/auth/?${new URLSearchParams({ api_key: env.LASTFM_API_KEY!, cb: callbackUrl })}`;
+
+/** Signature rules: params sorted by name, concatenated as name+value, shared secret appended, md5. */
+export function lastfmSignature(params: Record<string, string>, secret = env.LASTFM_SHARED_SECRET!): string {
+  const base = Object.keys(params)
+    .sort()
+    .map((k) => k + params[k])
+    .join('');
+  return createHash('md5').update(base + secret, 'utf8').digest('hex');
+}
+
+/** Exchange the callback token for a session (username + session key). */
+export async function lastfmSession(token: string) {
+  const params = { api_key: env.LASTFM_API_KEY!, method: 'auth.getSession', token };
+  const url = `https://ws.audioscrobbler.com/2.0/?${new URLSearchParams({ ...params, api_sig: lastfmSignature(params), format: 'json' })}`;
+  const res = await fetchJson<{ session?: { name: string; key: string } }>(url);
+  if (!res?.session) throw new ProviderAuthError('Last.fm sign-in failed');
+  return res.session;
+}
+
 export async function lastfmUserExists(username: string): Promise<{ name: string } | null> {
   try {
     const res = await fetchJson<{ user: { name: string } }>(api({ method: 'user.getinfo', user: username }));

apps/api/src/routes/connections.ts

@@ -4,15 +4,17 @@ import { z } from 'zod';
 import { connectUsernameSchema, jellyfinConnectSchema, type NowPlayingProvider } from '@musicshare/shared';
 import { db, schema } from '../db';
 import type { User } from '../db/schema';
-import { env, spotifyConfigured } from '../env';
+import { appleMusicConfigured, env, spotifyConfigured } from '../env';
 import { requireUser } from '../lib/auth';
 import { encrypt, randomToken } from '../lib/crypto';
 import { entitlementsFor } from '../lib/entitlements';
 import { HttpError } from '../lib/http';
 import { redis } from '../lib/redis';
+import { AppleUserTokenError, appleDeveloperToken, recentlyPlayed, storefront } from '../lib/appleMusic';
 import { UnsafeUrlError, assertSafeServerUrl } from '../lib/ssrf';
 import { jellyfinAuthenticate, jellyfinLogout, jellyfinPublicInfo, type JellyfinMeta } from '../providers/jellyfin';
-import { lastfmUserExists } from '../providers/lastfm';
+import { lastfmAuthUrl, lastfmSession, lastfmUserExists } from '../providers/lastfm';
+import { ProviderAuthError } from '../providers/types';
 import { listenbrainzUserExists } from '../providers/listenbrainz';
 import * as plex from '../providers/plex';
 import * as spotify from '../providers/spotify';
@@ -80,7 +82,17 @@ export async function connectionRoutes(app: FastifyInstance) {
         return reply.redirect(returnTo.toString());
       }
       const tok = await spotify.exchangeCode(req.query.code);
-      const profile = await spotify.getProfile(tok.access_token);
+      let profile;
+      try {
+        profile = await spotify.getProfile(tok.access_token);
+      } catch (err) {
+        // Development-mode apps reject accounts not on the allowlist with 403.
+        if (err instanceof HttpError && err.status === 403) {
+          returnTo.searchParams.set('error', 'spotify_limited');
+          return reply.redirect(returnTo.toString());
+        }
+        throw err;
+      }
       await upsertConnection({
         userId,
         provider: 'spotify',
@@ -169,6 +181,85 @@ export async function connectionRoutes(app: FastifyInstance) {
     );
   });
 
+  // ---- Apple Music (MusicKit on iOS) ----
+
+  /** The iOS app needs a developer token to ask the system for the user's Music User Token. */
+  app.get('/connections/apple-music/developer-token', { config: { rateLimit: { max: 20, timeWindow: '1 minute' } } }, async (req) => {
+    requireUser(req);
+    if (!appleMusicConfigured) throw new HttpError(501, 'Apple Music is not configured on this server');
+    return { token: appleDeveloperToken() };
+  });
+
+  app.post('/connections/apple-music', async (req) => {
+    const user = requireUser(req);
+    if (!appleMusicConfigured) throw new HttpError(501, 'Apple Music is not configured on this server');
+    await assertCanConnect(user, 'apple_music');
+    const { musicUserToken } = z.object({ musicUserToken: z.string().min(20).max(4096) }).parse(req.body);
+
+    let region: { id: string; attributes?: { name: string } } | undefined;
+    let latest: string | null = null;
+    try {
+      region = (await storefront(musicUserToken)).data[0];
+      // Baseline: whatever was played last is history, not "listening now".
+      latest = (await recentlyPlayed(musicUserToken)).data[0]?.id ?? null;
+    } catch (err) {
+      if (err instanceof AppleUserTokenError) throw new HttpError(401, 'Apple Music rejected the authorization. Try again.');
+      throw err;
+    }
+    return toConnectionDTO(
+      await upsertConnection({
+        userId: user.id,
+        provider: 'apple_music',
+        externalUserId: 'me',
+        displayName: region?.attributes?.name ? `Apple Music (${region.attributes.name})` : 'Apple Music',
+        accessTokenEnc: encrypt(musicUserToken),
+        // lastSeenAt 0: the baseline song is history, so it never counts as "listening now".
+        meta: { storefront: region?.id, lastSeenId: latest, lastSeenAt: 0 },
+      }),
+    );
+  });
+
+  // ---- Last.fm (web auth): also the scalable route for Spotify, via Spotify's Last.fm link ----
+
+  app.post('/connections/lastfm/authorize', async (req) => {
+    const user = requireUser(req);
+    if (!env.LASTFM_API_KEY || !env.LASTFM_SHARED_SECRET) throw new HttpError(501, 'Last.fm sign-in is not configured on this server');
+    await assertCanConnect(user, 'lastfm');
+    const returnTo = resolveReturnTo(authorizeBodySchema.parse(req.body ?? {}));
+    const state = randomToken(24);
+    await redis.set(oauthStateKey(state), JSON.stringify({ userId: user.id, returnTo }), 'EX', 900);
+    return { url: lastfmAuthUrl(`${env.API_PUBLIC_URL}/connections/lastfm/callback?state=${state}`) };
+  });
+
+  app.get<{ Querystring: { state?: string; token?: string } }>('/connections/lastfm/callback', async (req, reply) => {
+    const raw = req.query.state ? await redis.getdel(oauthStateKey(req.query.state)) : null;
+    if (!raw) throw new HttpError(400, 'Invalid or expired Last.fm sign-in');
+    const { userId, ...state } = JSON.parse(raw) as { userId: string; returnTo: string };
+    const returnTo = new URL(state.returnTo);
+    if (!req.query.token) {
+      returnTo.searchParams.set('error', 'Last.fm sign-in was cancelled');
+      return reply.redirect(returnTo.toString());
+    }
+    let session;
+    try {
+      session = await lastfmSession(req.query.token);
+    } catch (err) {
+      if (!(err instanceof ProviderAuthError) && !(err instanceof HttpError)) throw err;
+      returnTo.searchParams.set('error', 'Last.fm sign-in failed');
+      return reply.redirect(returnTo.toString());
+    }
+    await upsertConnection({
+      userId,
+      provider: 'lastfm',
+      externalUserId: session.name,
+      displayName: session.name,
+      // Not needed for public listening history; kept for private profiles and future features.
+      accessTokenEnc: encrypt(session.key),
+    });
+    returnTo.searchParams.set('connected', 'lastfm');
+    return reply.redirect(returnTo.toString());
+  });
+
   // ---- username-based scrobblers ----
 
   app.post('/connections/lastfm', async (req) => {

apps/api/test/apple-music.test.ts

@@ -0,0 +1,169 @@
+import { createPublicKey, verify } from 'node:crypto';
+import { eq } from 'drizzle-orm';
+import { afterEach, describe, expect, it, vi } from 'vitest';
+import { db, schema } from '../src/db';
+import { appleDeveloperToken, resetAppleTokenCache } from '../src/lib/appleMusic';
+import { appleMusicProvider } from '../src/providers/appleMusic';
+import { ProviderAuthError } from '../src/providers/types';
+import { bearer, createUser, json, routeFetch, useTestApp } from './helpers';
+
+const app = useTestApp();
+afterEach(() => vi.unstubAllGlobals());
+
+const song = (id: string, name: string, extra: Record<string, unknown> = {}) => ({
+  id,
+  type: 'songs',
+  attributes: {
+    name,
+    artistName: 'Joy Division',
+    albumName: 'Closer',
+    durationInMillis: 240_000,
+    isrc: 'GBAAA8000001',
+    url: `https://music.apple.com/us/album/closer/1?i=${id}`,
+    artwork: { url: 'https://is1-ssl.mzstatic.com/image/thumb/x/{w}x{h}bb.jpg' },
+    ...extra,
+  },
+});
+
+function stubApple(recent: () => unknown[], status = 200) {
+  const calls: { url: string; headers: Record<string, string> }[] = [];
+  vi.stubGlobal(
+    'fetch',
+    routeFetch([
+      [
+        /api\.music\.apple\.com\/v1\/me\/storefront/,
+        (url, init) => (calls.push({ url, headers: init?.headers as Record<string, string> }), json({ data: [{ id: 'us', attributes: { name: 'United States' } }] }, status)),
+      ],
+      [
+        /api\.music\.apple\.com\/v1\/me\/recent\/played\/tracks/,
+        (url, init) => (calls.push({ url, headers: init?.headers as Record<string, string> }), json({ data: recent() }, status)),
+      ],
+    ]),
+  );
+  return calls;
+}
+
+async function connect(token: string) {
+  return app().inject({
+    method: 'POST',
+    url: '/connections/apple-music',
+    headers: bearer(token),
+    payload: { musicUserToken: 'music-user-token-from-ios-0123456789' },
+  });
+}
+
+describe('Apple Music developer token', () => {
+  it('is an ES256 JWT signed with the MusicKit key', () => {
+    resetAppleTokenCache();
+    const [header, payload, signature] = appleDeveloperToken().split('.');
+    expect(JSON.parse(Buffer.from(header!, 'base64url').toString())).toEqual({ alg: 'ES256', kid: 'KEYID12345' });
+    const claims = JSON.parse(Buffer.from(payload!, 'base64url').toString());
+    expect(claims.iss).toBe('TEAMID1234');
+    expect(claims.exp - claims.iat).toBeLessThanOrEqual(15_777_000); // Apple's 6-month maximum
+    const ok = verify(
+      'sha256',
+      Buffer.from(`${header}.${payload}`),
+      { key: createPublicKey(process.env.APPLE_TEST_PUBLIC_KEY!), dsaEncoding: 'ieee-p1363' },
+      Buffer.from(signature!, 'base64url'),
+    );
+    expect(ok).toBe(true);
+  });
+
+  it('is cached rather than re-signed on every request', () => {
+    resetAppleTokenCache();
+    expect(appleDeveloperToken()).toBe(appleDeveloperToken());
+  });
+
+  it('is only handed to signed-in users', async () => {
+    expect((await app().inject({ url: '/connections/apple-music/developer-token' })).statusCode).toBe(401);
+    const { token } = await createUser(app(), 'alice');
+    const res = await app().inject({ url: '/connections/apple-music/developer-token', headers: bearer(token) });
+    expect(res.json().token.split('.')).toHaveLength(3);
+  });
+});
+
+describe('connecting Apple Music', () => {
+  it('validates the token, stores it encrypted, and baselines the last played song', async () => {
+    const calls = stubApple(() => [song('100', 'Atmosphere')]);
+    const { token, user } = await createUser(app(), 'alice');
+    const res = await connect(token);
+    expect(res.statusCode).toBe(200);
+    expect(res.json()).toMatchObject({ provider: 'apple_music', displayName: 'Apple Music (United States)', status: 'active' });
+    expect(calls[0]!.headers['Music-User-Token']).toBe('music-user-token-from-ios-0123456789');
+    expect(calls[0]!.headers.Authorization).toMatch(/^Bearer ey/);
+
+    const [row] = await db.select().from(schema.connections).where(eq(schema.connections.userId, user.id));
+    expect(row!.accessTokenEnc).not.toContain('music-user-token');
+    expect(row!.meta).toMatchObject({ storefront: 'us', lastSeenId: '100' });
+  });
+
+  it('rejects a token Apple refuses', async () => {
+    stubApple(() => [], 401);
+    const { token } = await createUser(app(), 'alice');
+    expect((await connect(token)).statusCode).toBe(401);
+  });
+});
+
+describe('Apple Music polling', () => {
+  async function connected(recent: { current: object[] }) {
+    stubApple(() => recent.current);
+    const { token, user } = await createUser(app(), 'alice');
+    await connect(token);
+    const load = async () => (await db.select().from(schema.connections).where(eq(schema.connections.userId, user.id)))[0]!;
+    return { load, user };
+  }
+
+  it("doesn't announce the song that was already last-played when connecting", async () => {
+    const recent: { current: object[] } = { current: [song('100', 'Atmosphere')] };
+    const { load } = await connected(recent);
+    expect(await appleMusicProvider.poll(await load())).toBeNull();
+  });
+
+  it('announces a newly played song with its Apple Music link, ISRC and artwork', async () => {
+    const recent: { current: object[] } = { current: [song('100', 'Atmosphere')] };
+    const { load } = await connected(recent);
+    recent.current = [song('200', 'Decades')];
+    const result = await appleMusicProvider.poll(await load());
+    expect(result).toMatchObject({
+      isPlaying: true,
+      track: {
+        title: 'Decades',
+        artist: 'Joy Division',
+        isrc: 'GBAAA8000001',
+        durationMs: 240_000,
+        artworkUrl: 'https://is1-ssl.mzstatic.com/image/thumb/x/600x600bb.jpg',
+        links: { apple_music: { id: '200', url: 'https://music.apple.com/us/album/closer/1?i=200' } },
+      },
+    });
+  });
+
+  it('keeps it playing for the song length, then stops', async () => {
+    const recent: { current: object[] } = { current: [song('100', 'Atmosphere')] };
+    const { load } = await connected(recent);
+    recent.current = [song('200', 'Decades')];
+    await appleMusicProvider.poll(await load());
+    expect((await appleMusicProvider.poll(await load()))?.isPlaying).toBe(true);
+
+    const conn = await load();
+    await db
+      .update(schema.connections)
+      .set({ meta: { ...(conn.meta as object), lastSeenAt: Date.now() - 240_000 - 31_000 } })
+      .where(eq(schema.connections.id, conn.id));
+    expect(await appleMusicProvider.poll(await load())).toBeNull();
+  });
+
+  it('library uploads play without a store link', async () => {
+    const recent: { current: object[] } = { current: [song('100', 'Atmosphere')] };
+    const { load } = await connected(recent);
+    recent.current = [{ id: 'i.abc', type: 'library-songs', attributes: { name: 'Home Demo', artistName: 'Me' } }];
+    const result = await appleMusicProvider.poll(await load());
+    expect(result?.track).toMatchObject({ title: 'Home Demo', links: undefined, isrc: null });
+  });
+
+  it('flags an expired Music User Token as needing reconnect', async () => {
+    const recent: { current: object[] } = { current: [song('100', 'Atmosphere')] };
+    const { load } = await connected(recent);
+    stubApple(() => [], 403);
+    await expect(appleMusicProvider.poll(await load())).rejects.toBeInstanceOf(ProviderAuthError);
+  });
+});

apps/api/test/oauth.test.ts

@@ -0,0 +1,87 @@
+import { createHash } from 'node:crypto';
+import { eq } from 'drizzle-orm';
+import { afterEach, describe, expect, it, vi } from 'vitest';
+import { db, schema } from '../src/db';
+import { decrypt } from '../src/lib/crypto';
+import { lastfmSignature } from '../src/providers/lastfm';
+import { bearer, createUser, json, routeFetch, useTestApp } from './helpers';
+
+const app = useTestApp();
+afterEach(() => vi.unstubAllGlobals());
+
+const stateFrom = (url: string) => decodeURIComponent(url).match(/state=([^&]+)/)![1]!;
+
+describe('Last.fm sign-in', () => {
+  it('signs requests per the Last.fm rules: sorted name+value pairs, secret appended, md5', () => {
+    const expected = createHash('md5').update('api_keykmethodmtokent' + 's').digest('hex');
+    expect(lastfmSignature({ token: 't', method: 'm', api_key: 'k' }, 's')).toBe(expected);
+  });
+
+  it('runs the web auth flow and stores the username and session key', async () => {
+    let sessionUrl = '';
+    vi.stubGlobal(
+      'fetch',
+      routeFetch([[/auth\.getSession/, (url) => ((sessionUrl = url), json({ session: { name: 'RJ', key: 'sk-123', subscriber: 0 } }))]]),
+    );
+    const { token, user } = await createUser(app(), 'alice');
+    const start = await app().inject({
+      method: 'POST',
+      url: '/connections/lastfm/authorize',
+      headers: bearer(token),
+      payload: { client: 'mobile', returnTo: 'musicshare://settings' },
+    });
+    const authUrl = new URL(start.json().url);
+    expect(authUrl.host).toBe('www.last.fm');
+    expect(authUrl.searchParams.get('api_key')).toBe('test-lastfm-key');
+    const cb = new URL(authUrl.searchParams.get('cb')!);
+    expect(cb.href).toMatch(/^https:\/\/api\.test\/connections\/lastfm\/callback\?state=/);
+
+    const done = await app().inject({ url: `/connections/lastfm/callback?state=${stateFrom(cb.href)}&token=lfm-token` });
+    expect(done.statusCode).toBe(302);
+    expect(done.headers.location).toBe('musicshare://settings?connected=lastfm');
+
+    const params = new URL(sessionUrl).searchParams;
+    expect(params.get('api_sig')).toBe(
+      lastfmSignature({ api_key: 'test-lastfm-key', method: 'auth.getSession', token: 'lfm-token' }, 'test-lastfm-secret'),
+    );
+    const [row] = await db.select().from(schema.connections).where(eq(schema.connections.userId, user.id));
+    expect(row).toMatchObject({ provider: 'lastfm', externalUserId: 'RJ' });
+    expect(decrypt(row!.accessTokenEnc!)).toBe('sk-123');
+  });
+
+  it('returns to the app with an error if the user cancels', async () => {
+    const { token } = await createUser(app(), 'alice');
+    const start = await app().inject({ method: 'POST', url: '/connections/lastfm/authorize', headers: bearer(token), payload: { client: 'web' } });
+    const state = stateFrom(new URL(start.json().url).searchParams.get('cb')!);
+    const done = await app().inject({ url: `/connections/lastfm/callback?state=${state}` });
+    expect(done.headers.location).toMatch(/^http:\/\/web\.test\/settings\?error=/);
+  });
+
+  it('rejects replayed or forged states', async () => {
+    expect((await app().inject({ url: '/connections/lastfm/callback?state=forged&token=x' })).statusCode).toBe(400);
+  });
+});
+
+describe('Spotify sign-in during the limited beta', () => {
+  it('sends users who are not on the allowlist back with a friendly error instead of failing', async () => {
+    vi.stubGlobal(
+      'fetch',
+      routeFetch([
+        [/accounts\.spotify\.com\/api\/token/, () => json({ access_token: 'a', refresh_token: 'r', expires_in: 3600 })],
+        [/api\.spotify\.com\/v1\/me$/, () => json({ error: { status: 403, message: 'User not registered in the Developer Dashboard' } }, 403)],
+      ]),
+    );
+    const { token } = await createUser(app(), 'alice');
+    const start = await app().inject({
+      method: 'POST',
+      url: '/connections/spotify/authorize',
+      headers: bearer(token),
+      payload: { client: 'mobile', returnTo: 'musicshare://settings' },
+    });
+    const state = new URL(start.json().url).searchParams.get('state');
+    const done = await app().inject({ url: `/connections/spotify/callback?state=${state}&code=abc` });
+    expect(done.statusCode).toBe(302);
+    expect(done.headers.location).toBe('musicshare://settings?error=spotify_limited');
+    expect(await db.select().from(schema.connections)).toHaveLength(0);
+  });
+});

apps/api/vitest.config.ts

@@ -1,5 +1,9 @@
+import { generateKeyPairSync } from 'node:crypto';
 import { defineConfig } from 'vitest/config';
 
+// Throwaway MusicKit-style key so Apple developer tokens can be signed and verified in tests.
+const appleKey = generateKeyPairSync('ec', { namedCurve: 'P-256' });
+
 /**
  * Tests run against a dedicated Postgres database and Redis DB index, never
  * the dev ones (test/helpers.ts refuses to wipe anything else). Override with
@@ -14,9 +18,14 @@ const testEnv = {
   API_PUBLIC_URL: 'https://api.test',
   ALLOW_PRIVATE_SERVER_URLS: 'false',
   LASTFM_API_KEY: 'test-lastfm-key',
-  SPOTIFY_CLIENT_ID: '',
-  SPOTIFY_CLIENT_SECRET: '',
+  LASTFM_SHARED_SECRET: 'test-lastfm-secret',
+  SPOTIFY_CLIENT_ID: 'test-spotify-id',
+  SPOTIFY_CLIENT_SECRET: 'test-spotify-secret',
   ODESLI_API_KEY: '',
+  APPLE_TEAM_ID: 'TEAMID1234',
+  APPLE_MUSICKIT_KEY_ID: 'KEYID12345',
+  APPLE_MUSICKIT_PRIVATE_KEY: appleKey.privateKey.export({ type: 'pkcs8', format: 'pem' }).toString().replace(/\n/g, '\\n'),
+  APPLE_TEST_PUBLIC_KEY: appleKey.publicKey.export({ type: 'spki', format: 'pem' }).toString(),
 };
 
 export default defineConfig({