Way back when I was in school (2004 or so) I set up a proxy on my personal website to get around them blocking email, because I don’t want to have to save things to a damned floppy drive.

I then let a teacher use it because he was frustrated half of his search results would get blocked. From there, it spread like wildfire. Eventually they blocked it and from then on the IT guy would give me a side eye whenever we crossed paths.

Anyways, I can only imagine the clever ways kids get around things now. If it’s not per device, all a kid would need is a mobile hotspot to be king.

Back in the day when every hotel that was charging for WiFi was stupidly leaving port 53 wide open, I wrote an IP over DNS tunnel to get free WiFi. Worked great until I went to a hotel in Tokyo and turned it on. Suddenly my network connection was completely dead. They were clearly watching for shenanigans. Took me a few minutes to figure out they had redirected my MAC address to the bit bucket. I spoofed my MAC to a different one, and then behaved, as well as admired those IT guys.

Yeah, back when I was in school it was a cat and mouse game of finding a new proxy every week when the last one got blocked. The minute someone found a new one, it was everywhere.

I decided to sidestep the whole game and run my own proxy at home. I didn't have enough bandwidth for multiple users, so it was just me. I don't think IT ever caught on.