One day my mom's email stopped working, so I contacted a CSR for the ISP. After 2 hours of being passed around to their highest level of tech support and explaining that she signed up for some shitty extra antivirus service some time before and that her actual email was probably aliased to an account on the special antivirus server, they kept insisting the account didn't exist and that I was lying. I tried to explain that it was almost a given that the alias just got deleted by someone doing clean-up too many times and I lost all patience. I dedicated all night to gaining access to their mail servers and getting my moms account back up.
I documented everything and the next day I went over and talked to their head engineer. I explained everything while sitting in a computer in his office proving the hack. I got a free lunch and 3 months of free internet service out of it. I was also called in a month later to corroborate the vulnerability was patched.
Two or three weeks later I got suspended from school for stealing some exams from the teachers shares in their "private" network. I covered my tracks, but a girl in the computer room at the time accused me of doing "something fishy" and I was caught with a floppy that contained the exams. That drama took the better part of the month and included my lawyer (my uncle doing me a favor) making incredible legal threats. I almost failed that quarter, but I did get off mostly unpunished.
I do development and specialize in security and risk assessment these days. It's nowhere as fun as it used to be in the early 90's.