Paying parking tickets in SF. Input my license number and CC info and it would detect and pay parking tickets that came up. There is a CAPTCHA which was trivially solvable with Tessaract OCR.
When you say parking tickets, as in plural, it really makes wonder what kind of person would rack up so many parking tickets to make that worthwhile. I hope it's all in good fun...
[1] https://techcrunch.com/2016/06/15/fixed-the-app-that-helps-y...