How to Monitor Multi-Step API Authentication Flows

Authentication is almost always the first thing to break. Your login flow touches your web server, your database, your session store or token issuer, and often one or more third-party identity providers. A failure in any one of those components means your users cannot log in, even if every other page on your site loads perfectly. The challenge is that a single HTTP check cannot test an authentication flow. Logging in is inherently multi-step: you send credentials, receive a token, and then use that token to access a protected resource. If you only check the login endpoint with a GET Why Single-Request Checks Fall Short Consider a typical API login flow. A client sends a POST /api/auth/login Authorization A standard HTTP monitor can check that /api/auth/login 200 OK Real authentication failures are subtle. The login endpoint responds, but the token it returns is malformed. Or the session store is full and new sessions silently fail. Or a key rotation broke JWT verification on downstream