What's more concerning to me is school administrators who are so quick with the stick when they could be using a carrot instead. Give this kid a study hour to work on stuff with the IT guy. Probably he could do a lot of good work for the school, effectively for free, and he'd have no reason to keep up the circumvention game.
Which, to be clear, is what this is. It's fun to break the rules and feel you're speaking truth to power. I know I did that in high school, even taking apart a computer to remove the CMOS battery to reset the BIOS password to launch a different OS. No good reason for it, it's just fun. The trouble is it's a dangerous game this kid is playing. And it needn't be, they could turn this into a great learning opportunity.
But no, school administrators keep up their tiny dictatorship image, and this kid will get expelled or something. Oh well.