Loom Auth

Authentication & Authorization

Overview

This skill covers comprehensive authentication and authorization strategies for modern applications. It includes identity verification (authentication), access control (authorization), and secure credential management across web, mobile, and API contexts.

When to Use

senior-software-engineer (Opus) - DEFAULT for all auth work:

• Designing auth architecture from scratch
• Choosing between authentication strategies (JWT vs sessions, OAuth flows)
• Evaluating trade-offs between different access control models
• Planning token rotation, refresh strategies, or session lifecycle
• Making cross-cutting security decisions
• Implementing auth flows (login, logout, password reset)
• Adding JWT or session handling to existing applications
• Implementing RBAC/ABAC patterns
• Integrating with OAuth2 providers
• Adding MFA or API key authentication
• Implementing password hashing or credential storage
• Handling sensitive tokens (refresh tokens, API keys)
• Implementing rate limiting or brute force protection

software-engineer (Sonnet) - ONLY for:

• Writing unit tests for existing auth code
• Boilerplate auth middleware following established patterns
• Scaffolding from a concrete, detailed plan
• Adding MFA or step-up authentication
• Dealing with PII, compliance, or regulatory requirements
• ANY authentication/authorization implementation before production
• Setting up identity providers (Keycloak, Auth0, Cognito)
• Configuring SSO, SAML, or OIDC integrations
• Scaling session storage (Redis clusters, distributed sessions)
• Managing secrets, key rotation infrastructure
• Setting up certificate management for JWT signing

Key Concepts

OAuth2 Flows

Authorization Code Flow - Best for server-side applications:

// 1. Redirect user to authorization server
const authUrl = new URL("https://auth.example.com/authorize");
authUrl.searchParams.set("response_type", "code");
authUrl.searchParams.set("client_id", CLIENT_ID);
authUrl.searchParams.set("redirect_uri", REDIRECT_URI);
authUrl.searchParams.set("scope", "openid profile email");
authUrl.searchParams.set("state", generateSecureState());

// 2. Exchange code for tokens (server-side)
async function exchangeCode(code: string): Promise<TokenResponse> {
  const response = await fetch("https://auth.example.com/token", {
    method: "POST",
    headers: { "Content-Type": "application/x-www-form-urlencoded" },
    body: new URLSearchParams({
      grant_type: "authorization_code",
      code,
      client_id: CLIENT_ID,
      client_secret: CLIENT_SECRET,
      redirect_uri: REDIRECT_URI,
    }),
  });
  return response.json();
}

PKCE Flow - Required for public clients (SPAs, mobile apps):

// Generate code verifier and challenge
function generatePKCE(): { verifier: string; challenge: string } {
  const verifier = base64UrlEncode(crypto.getRandomValues(new Uint8Array(32)));
  const challenge = base64UrlEncode(
    await crypto.subtle.digest("SHA-256", new TextEncoder().encode(verifier)),
  );
  return { verifier, challenge };
}

// Include in authorization request
authUrl.searchParams.set("code_challenge", challenge);
authUrl.searchParams.set("code_challenge_method", "S256");

// Include verifier in token exchange
body.set("code_verifier", verifier);

Client Credentials Flow - For service-to-service communication:

async function getServiceToken(): Promise<string> {
  const response = await fetch("https://auth.example.com/token", {
    method: "POST",
    headers: {
      "Content-Type": "application/x-www-form-urlencoded",
      Authorization: `Basic ${btoa(`${CLIENT_ID}:${CLIENT_SECRET}`)}`,
    },
    body: new URLSearchParams({
      grant_type: "client_credentials",
      scope: "api:read api:write",
    }),
  });
  return (await response.json()).access_token;
}

JWT Handling

Token Structure and Signing:

import jwt from "jsonwebtoken";

interface TokenPayload {
  sub: string; // Subject (user ID)
  iss: string; // Issuer
  aud: string; // Audience
  exp: number; // Expiration
  iat: number; // Issued at
  roles: string[]; // Custom claims
}

// Sign with RS256 (asymmetric - recommended for production)
function signToken(payload: Omit<TokenPayload, "iat" | "exp">): string {
  return jwt.sign(
    { ...payload, iat: Math.floor(Date.now() / 1000) },
    PRIVATE_KEY,
    {
      algorithm: "RS256",
      expiresIn: "15m",
      issuer: "https://api.example.com",
      audience: "https://app.example.com",
    },
  );
}

// Verify token
function verifyToken(token: string): TokenPayload {
  return jwt.verify(token, PUBLIC_KEY, {
    algorithms: ["RS256"],
    issuer: "https://api.example.com",
    audience: "https://app.example.com",
  }) as TokenPayload;
}

Refresh Token Pattern:

interface TokenPair {
  accessToken: string; // Short-lived (15 min)
  refreshToken: string; // Long-lived (7 days), stored securely
}

async function refreshTokens(refreshToken: string): Promise<TokenPair> {
  // Validate refresh token exists in database (allows revocation)
  const storedToken = await db.refreshTokens.findUnique({
    where: { token: hashToken(refreshToken) },
  });

  if (!storedToken || storedToken.expiresAt < new Date()) {
    throw new UnauthorizedError("Invalid refresh token");
  }

  // Rotate refresh token (one-time use)
  await db.refreshTokens.delete({ where: { id: storedToken.id } });

  const newRefreshToken = generateSecureToken();
  await db.refreshTokens.create({
    data: {
      token: hashToken(newRefreshToken),
      userId: storedToken.userId,
      expiresAt: addDays(new Date(), 7),
    },
  });

  return {
    accessToken: signToken({ sub: storedToken.userId, roles: [] }),
    refreshToken: newRefreshToken,
  };
}

RBAC (Role-Based Access Control)

// Define roles and permissions
const ROLES = {
  admin: [
    "users:read",
    "users:write",
    "users:delete",
    "reports:read",
    "settings:write",
  ],
  manager: ["users:read", "users:write", "reports:read"],
  user: ["users:read:own", "reports:read:own"],
} as const;

type Role = keyof typeof ROLES;
type Permission = (typeof ROLES)[Role][number];

// Middleware for permission checking
function requirePermission(permission: Permission) {
  return (req: Request, res: Response, next: NextFunction) => {
    const userRoles: Role[] = req.user.roles;
    const userPermissions = userRoles.flatMap((role) => ROLES[role]);

    // Handle :own suffix for resource-level permissions
    const [resource, action, scope] = permission.split(":");
    const basePermission = `${resource}:${action}`;

    const hasPermission =
      userPermissions.includes(permission) ||
      (scope === "own" && userPermissions.includes(basePermission));

    if (!hasPermission) {
      return res.status(403).json({ error: "Forbidden" });
    }
    next();
  };
}

// Usage
app.delete("/users/:id", requirePermission("users:delete"), deleteUser);

ABAC (Attribute-Based Access Control)

interface PolicyContext {
  subject: { id: string; roles: string[]; department: string };
  resource: { type: string; owner: string; classification: string };
  action: string;
  environment: { time: Date; ip: string };
}

type Policy = (ctx: PolicyContext) => boolean;

const policies: Policy[] = [
  // Users can access their own resources
  (ctx) => ctx.resource.owner === ctx.subject.id,

  // Managers can access resources in their department
  (ctx) =>
    ctx.subject.roles.includes("manager") &&
    ctx.resource.department === ctx.subject.department,

  // No access to confidential resources outside business hours
  (ctx) => {
    if (ctx.resource.classification === "confidential") {
      const hour = ctx.environment.time.getHours();
      return hour >= 9 && hour < 17;
    }
    return true;
  },
];

function checkAccess(ctx: PolicyContext): boolean {
  return policies.every((policy) => policy(ctx));
}

Session Management

import { Redis } from "ioredis";

const redis = new Redis();
const SESSION_TTL = 24 * 60 * 60; // 24 hours

interface Session {
  userId: string;
  createdAt: number;
  lastActivity: number;
  userAgent: string;
  ip: string;
}

async function createSession(userId: string, req: Request): Promise<string> {
  const sessionId = crypto.randomUUID();
  const session: Session = {
    userId,
    createdAt: Date.now(),
    lastActivity: Date.now(),
    userAgent: req.headers["user-agent"] || "",
    ip: req.ip,
  };

  await redis.setex(
    `session:${sessionId}`,
    SESSION_TTL,
    JSON.stringify(session),
  );
  await redis.sadd(`user-sessions:${userId}`, sessionId);

  return sessionId;
}

async function validateSession(sessionId: string): Promise<Session | null> {
  const data = await redis.get(`session:${sessionId}`);
  if (!data) return null;

  const session: Session = JSON.parse(data);

  // Update last activity
  session.lastActivity = Date.now();
  await redis.setex(
    `session:${sessionId}`,
    SESSION_TTL,
    JSON.stringify(session),
  );

  return session;
}

async function invalidateAllUserSessions(userId: string): Promise<void> {
  const sessionIds = await redis.smembers(`user-sessions:${userId}`);
  if (sessionIds.length > 0) {
    await redis.del(...sessionIds.map((id) => `session:${id}`));
    await redis.del(`user-sessions:${userId}`);
  }
}

API Key Strategies

interface ApiKey {
  id: string;
  prefix: string; // First 8 chars (for identification)
  hash: string; // Hashed key
  name: string;
  scopes: string[];
  rateLimit: number;
  expiresAt: Date | null;
  lastUsedAt: Date | null;
}

// Generate API key with prefix for easy identification
function generateApiKey(): { key: string; prefix: string; hash: string } {
  const key = `sk_live_${crypto.randomBytes(32).toString("base64url")}`;
  return {
    key,
    prefix: key.substring(0, 16),
    hash: crypto.createHash("sha256").update(key).digest("hex"),
  };
}

// Validate and rate limit
async function validateApiKey(key: string): Promise<ApiKey> {
  const hash = crypto.createHash("sha256").update(key).digest("hex");
  const apiKey = await db.apiKeys.findUnique({ where: { hash } });

  if (!apiKey) throw new UnauthorizedError("Invalid API key");
  if (apiKey.expiresAt && apiKey.expiresAt < new Date()) {
    throw new UnauthorizedError("API key expired");
  }

  // Check rate limit
  const rateLimitKey = `ratelimit:${apiKey.id}`;
  const requests = await redis.incr(rateLimitKey);
  if (requests === 1) await redis.expire(rateLimitKey, 60);
  if (requests > apiKey.rateLimit) {
    throw new TooManyRequestsError("Rate limit exceeded");
  }

  // Update last used (async, don't wait)
  db.apiKeys.update({
    where: { id: apiKey.id },
    data: { lastUsedAt: new Date() },
  });

  return apiKey;
}

Password Hashing

import argon2 from "argon2";
import bcrypt from "bcrypt";

// Argon2 (recommended for new implementations)
async function hashPasswordArgon2(password: string): Promise<string> {
  return argon2.hash(password, {
    type: argon2.argon2id, // Hybrid mode
    memoryCost: 65536, // 64 MB
    timeCost: 3, // 3 iterations
    parallelism: 4, // 4 threads
  });
}

async function verifyPasswordArgon2(
  hash: string,
  password: string,
): Promise<boolean> {
  return argon2.verify(hash, password);
}

// bcrypt (widely supported)
const BCRYPT_ROUNDS = 12;

async function hashPasswordBcrypt(password: string): Promise<string> {
  return bcrypt.hash(password, BCRYPT_ROUNDS);
}

async function verifyPasswordBcrypt(
  hash: string,
  password: string,
): Promise<boolean> {
  return bcrypt.compare(password, hash);
}

// Password validation
function validatePasswordStrength(password: string): {
  valid: boolean;
  errors: string[];
} {
  const errors: string[] = [];

  if (password.length < 12)
    errors.push("Password must be at least 12 characters");
  if (!/[A-Z]/.test(password))
    errors.push("Password must contain uppercase letter");
  if (!/[a-z]/.test(password))
    errors.push("Password must contain lowercase letter");
  if (!/[0-9]/.test(password)) errors.push("Password must contain number");
  if (!/[^A-Za-z0-9]/.test(password))
    errors.push("Password must contain special character");

  return { valid: errors.length === 0, errors };
}

MFA Implementation

import { authenticator } from "otplib";
import QRCode from "qrcode";

// TOTP Setup
async function setupTOTP(
  userId: string,
  email: string,
): Promise<{ secret: string; qrCode: string }> {
  const secret = authenticator.generateSecret();
  const otpauth = authenticator.keyuri(email, "MyApp", secret);
  const qrCode = await QRCode.toDataURL(otpauth);

  // Store encrypted secret temporarily until verified
  await redis.setex(`mfa-setup:${userId}`, 600, encrypt(secret));

  return { secret, qrCode };
}

// Verify TOTP
function verifyTOTP(secret: string, token: string): boolean {
  return authenticator.verify({ token, secret });
}

// Backup codes generation
function generateBackupCodes(): { codes: string[]; hashes: string[] } {
  const codes = Array.from({ length: 10 }, () =>
    crypto.randomBytes(4).toString("hex").toUpperCase(),
  );
  const hashes = codes.map((code) =>
    crypto.createHash("sha256").update(code).digest("hex"),
  );
  return { codes, hashes };
}

// Complete MFA verification flow
async function verifyMFA(userId: string, code: string): Promise<boolean> {
  const user = await db.users.findUnique({
    where: { id: userId },
    include: { mfaSettings: true },
  });

  if (!user?.mfaSettings?.enabled) return true;

  // Try TOTP first
  if (verifyTOTP(decrypt(user.mfaSettings.totpSecret), code)) {
    return true;
  }

  // Try backup code
  const codeHash = crypto.createHash("sha256").update(code).digest("hex");
  const backupCode = user.mfaSettings.backupCodes.find(
    (bc) => bc.hash === codeHash && !bc.usedAt,
  );

  if (backupCode) {
    await db.backupCodes.update({
      where: { id: backupCode.id },
      data: { usedAt: new Date() },
    });
    return true;
  }

  return false;
}

Security Considerations

Critical Security Checklist (for senior-software-engineer review):

1. Credential Storage

   • Never log passwords, tokens, or API keys
   • Hash passwords with Argon2id or bcrypt (12+ rounds)
   • Hash API keys before database storage
   • Encrypt refresh tokens and MFA secrets at rest
   • Never return sensitive data in error messages

2. Token Security

   • Validate ALL token claims (signature, exp, iss, aud, nbf)
   • Use RS256 or ES256 for JWT signatures (never HS256 in distributed systems)
   • Set minimum token expiration (access: 15 min, refresh: 7 days max)
   • Implement token revocation lists for logout
   • Use PKCE for all public clients (SPAs, mobile)

3. Attack Prevention

   • Implement rate limiting on auth endpoints (5 attempts per 15 min)
   • Account lockout after failed login attempts (10 failures = 30 min lockout)
   • Use timing-safe comparison for password/token validation
   • Prevent user enumeration (same error for invalid user/password)
   • Validate redirect URIs against allowlist (prevent open redirects)

4. Session Security

   • Set httpOnly, secure, sameSite=strict on cookies
   • Regenerate session ID after privilege escalation
   • Implement absolute timeout (24h) and idle timeout (30min)
   • Clear all sessions on password change
   • Detect and alert on concurrent sessions from different IPs

5. Transport Security

   • Require HTTPS for all auth endpoints (HSTS header)
   • Use secure WebSocket (wss://) for real-time auth
   • Validate Content-Type headers (prevent CSRF)
   • Set CORS policies restrictively

6. Compliance & Privacy

   • Log authentication events (login, logout, failures) for audit
   • Implement PII data retention policies
   • Support account deletion (GDPR right to erasure)
   • Provide data export (GDPR right to portability)
   • Consider SOC2, HIPAA, PCI-DSS requirements if applicable

Common Vulnerabilities to Avoid:

• Timing attacks (use crypto.timingSafeEqual)
• JWT algorithm confusion (always specify allowed algorithms)
• Session fixation (regenerate ID on login)
• Insecure direct object references (verify resource ownership)
• Mass assignment (validate all input fields)
• Broken access control (default deny, explicit allow)

Best Practices

1. Token Security

   • Use short-lived access tokens (15 minutes or less)
   • Store refresh tokens securely (httpOnly cookies, encrypted storage)
   • Implement token rotation for refresh tokens
   • Always validate token signature, expiration, issuer, and audience

2. Password Security

   • Use Argon2id for new implementations
   • Never store plaintext passwords
   • Implement account lockout after failed attempts
   • Use secure password reset flows with time-limited tokens

3. Session Security

   • Regenerate session ID after authentication
   • Implement absolute and idle timeouts
   • Bind sessions to user agent/IP when appropriate
   • Provide session management UI for users

4. API Key Security

   • Hash API keys before storage
   • Use prefixes for key identification
   • Implement scopes and rate limiting
   • Allow key rotation without downtime

5. MFA Best Practices

   • Offer multiple MFA methods (TOTP, WebAuthn, SMS backup)
   • Provide backup codes during setup
   • Allow trusted device remembering
   • Require MFA re-verification for sensitive actions

Examples

Complete Login Flow with MFA

async function login(
  email: string,
  password: string,
  mfaCode?: string,
): Promise<AuthResponse> {
  // Find user
  const user = await db.users.findUnique({ where: { email } });
  if (!user) throw new UnauthorizedError("Invalid credentials");

  // Check account lockout
  if (user.lockedUntil && user.lockedUntil > new Date()) {
    throw new UnauthorizedError("Account temporarily locked");
  }

  // Verify password
  const validPassword = await verifyPasswordArgon2(user.passwordHash, password);
  if (!validPassword) {
    await incrementFailedAttempts(user.id);
    throw new UnauthorizedError("Invalid credentials");
  }

  // Check MFA
  if (user.mfaEnabled) {
    if (!mfaCode) {
      return { requiresMfa: true, mfaToken: generateMfaToken(user.id) };
    }
    const validMfa = await verifyMFA(user.id, mfaCode);
    if (!validMfa) throw new UnauthorizedError("Invalid MFA code");
  }

  // Reset failed attempts
  await db.users.update({
    where: { id: user.id },
    data: { failedAttempts: 0, lockedUntil: null },
  });

  // Generate tokens
  const accessToken = signToken({ sub: user.id, roles: user.roles });
  const refreshToken = await createRefreshToken(user.id);

  return { accessToken, refreshToken };
}