I ran a cgiproxy instance with proper ssl certs that totally bypassed and trivialized the school's internet filter. It was password protected with unique passwords per user and I had it set up in such a way I could tell when a password "got out" and I'd cancel it. It got added to the blocklist a couple times, but I was ready because I'd already registered like 20 dynamic dns services to point to the server. It would take them months to add it to the manual blocklist but just a minute to change a link on my forum so people used the next address in line. It was an open secret that I was running it, but I was pretty smart in how I ran it and who I provided access to. I also ran a forum that was popular with the student body and the passwords to the proxy were given out there, but only to people I trusted and could reasonably deduce who they were. Even then they didn't know it was me running the whole thing.

I mean most people probably did, but again I did it in such a way there was never any real paper trail. I never made any money or wanted any clout for it. I just thought it was fun that I got pissed off at the internet filter blocking newgrounds one day and thought "absolutely not", and basically trivialized the filter schoolwide.