Statute of limitations has expired... tell us yours and I might tell you mine (IBM 360/50 and CDC Cyber 72 and one of the first 10 Unix PDP-11s).
Ok, I'm glad I found this write-up I did on another forum, so I don't have to type it all out again.
We had a Univac 1100 at college in the early 80's. I did a lot of cool stuff on that machine. Being a young, curious freshman, I would spend hours reading the dusty system docs stored in the corner of one of the terminal rooms. I was also in a CS 101 class at the time. I found a command line utility that would really do a great job at re-formatting my PASCAL programs. Nobody else knew of this internal program (and it's dozen of command line params to make it work really well and customize how it formatted the programs). So I told a few friends. They started to use it. So, to help out everyone in the CS 101 classes (hundreds of engineering students), I made a public command file that embedded all the complex parameters and returned the formatted program. Then EVERYONE started using my little public batch file.
Then I got the neat idea that since people are submitting their code (read: homework) to my formatter, I could copy their code into my private directory for later "analysis". So I started getting copies of everyone else's homework. That was fun to review (although I was better than 95% of the class, most of the code was crap). But it started taking up too much space in my account, so I turned it off. And no, I never turned in or used anyone else's' code for my own homework assignments. I always completed the assignments long before anyone else.
But then the administration caught wind of my little program and that everyone was using it to format their assignments. They made a very strongly worded announcement to all CS classes that nobody was allowed to use this utility, and if anyone did, they would get a failing grade on their assignments. "People must learn good code formatting themselves, and not rely on an automatic tool". Of course, that was an empty threat, because there was no way they could actually tell if someone was just really good at formatting their program, or the utility did it the exact same way. Anyway, I was forced to remove the public script, but I continued to use it and showed a few friends how to access the command line tool.
The second thing I did was a lot worse. During the summer sessions, I got a job as a "consultant" in the terminal rooms to help summer students with CS assignments and usage of the UNIVAC. There was a skeleton staff during the summer, usually just one main system operator and someone to kick the printer and distribute the printouts, and me. Well, occasionally the main sysop would leave for dinner and ask me to "watch over" things while she was gone. Of course, being a good sysop and security minded, she would log out of her admin terminal before leaving.
So I would logon to my account while in her office. This one time (before phishing was a thing), I wrote a little script to run in my account that would spoof the actual logon screen, capture her login, password, and account code, write it out to my account, then log me out, and present a real logon page. So I'd just leave that running right before she got back.. I then started running it on terminals in the main computer room, too. The only problem was (1) the session would timeout in about 2 minutes, and (b), if someone happened to come up and hit CTRL-C (or whatever the break command was), they'd have open access to my account. So I didn't do that too much.
Then there was the time I was actually caught red-handed trying to hack (unsuccessfully) into my boss's (a CS grad student) account late one Friday night I was walking home drunk past the computer room. LUCKILY nothing happened, but I was sure I was going to be suspended or expelled for that one.