One of my favorites in my first couple of months in my career was testing a service that accepted user uploads and returned some value based on the upload. I thought “oh, I should just test a butt-load of invalid files”. Where am I gonna get a butt-load of invalid files for our service? I’ll just write a script that iterates and uploads everything under my `C:\Windows` folder. Discovered 2 bugs. One was that some random binary files there caused the parser the service was using to segfault and another about how the service stored those temp files before validating them. The first required involvement from a totally different team in the company because of “how serious it was”. As a fresh college hire at the time I got a ton of praise for “exposing such a critical buffer overflow” that went undetected for years (lol, I had no idea what I was doing but I took the praise). The latter was because the developer of the service never cleared their /tmp directory where they wrote user uploads before validating them. I ended up filling the VM disk with junk that took down the entire service.