I once got suspended because I figured out how to bypass my schools lockdown policies on the computers in the lab and wouldnt tell them how i did it.
(Hint: i learned they kept the "bypass" code in clear text in the registry, and later simply killed the processes from a command prompt with a batch file).
I also had a small apache server and ftp box i would tunnel though or get executables from i wanted to play (like pinball, the monsters blocked pinball). Since it was the very early days of the internet my morning routine generally consisted of waiting for folks to leave, firing up the server and taking over the fax line for the day and getting the IP before heading off to school.
I used a scheduler (probably cron, i dont remember) to bring it all down around 3pm before my parents got home.