The arms race between school administrators and people who wanted to connect to things they shouldn't has been going on for decades and is one of the major sources of sys admins. The problem here is that installing a VPN is far too easy and doesn't teach children where /etc/host is located.
At my school, they have default "teacher" for external events that use school facilities, usernames and passwords based on each school code that bypass all filters, but somehow no one has found it leading to insane workarounds. Sadly, people used to use web.archive.org as a workaround (like dude, just go home and look stuff up?) so they blocked it, which breaks a lot of research and sources on Wikipedia.
