Regularly, I would end up in trouble in my High School for things like bypassing the root account (using ShellShock), or nullifying their executable restrictions (because I needed to run my own executables for a work/study program). If I got caught, the IT admin would sit down and we'd chat about what happened, how they could improve their security and such. An administrator caught on to one of my shenanigans, bypassing the content block because I wanted to read a "hacking" article, and threatened me with suspension. Supposedly, she reported the incident to IT, and IT told her to not bother me anymore.
It was always disappointing when they took it too far and were directly caught by teachers or administration before I could tell them they were being a bit too blatantly malicious.