Begin with normal sign-in, then try a wrong password, expired password, and missing headers. Observe rate limits and response messages carefully. If errors disclose whether a user exists, report it clearly and stop. Respect lockouts, avoid automation without approval, and always leave systems healthier than you found them.
Think of tokens as signed permission slips. Check expiration, audience, and issuer claims. See what happens when you omit the Bearer prefix or use an expired token. Never brute force signatures. Instead, verify predictable mistakes, like weak validation or accepting unsigned tokens, then document clearly and recommend safer libraries.