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.