Current CAPTCHA tests are designed to be difficult for a bot and simple for a human-user to answer; however, as artificial intelligence improves, bots are more capable of using techniques such as optical character recognition to resolve current CAPTCHAs in similar manners as human-users. By maintaining a library of security tests and/or questions based on products purchased by the human-user, and using those questions as a CAPTCHA challenge in order to determine if the user is a human-user on how the user responds, CAPTCHA challenges may be directed toward determining a human-user based on responses exhibiting humanity.