I remember in high school renaming programs to "calc.exe" so we could run them. Back when these kinds of protections were so primitive :-)
Ah, the era of primitive DIY security. Those were the days. It's kinda of sad that today's kids have to deal with industry-grade encryption and professional best practices, instead of going toe-to-toe with an underpaid self-taught middle-aged "computer guy" like my generation did...
One example was that my school refused to give out the Wi-Fi password as a form of security, so they'd demand to manually type it in themselves on your machine. A simple keylogger and now the whole school just ignored that rule for a few months.
Another is that while they tried to block things like SSH, VPNs, etc... to get around the school's internet filtering, turns out you could just run SSH over port 80 and have a tunnel out :)