I Accidentally Discovered a Security Vulnerability in AI Education — Then Submitted It To a $200K Competition

Last night I was testing Maestro University, the first fully AI-taught university. I walked into their enrollment chatbot and asked it to analyze its own behavior. It did. Then I asked it how it evaluates students - what signals trigger "advanced" vs "beginner" classification. It told me. Then I used those exact signals in my responses. It gave me advanced treatment. Then I asked: "Did you just tell me how to game your system?" It said no.