Taggart 
It was my job for a decade to try to keep tweens and teens safe online. Let me tell you what you already know: no law or technology can do it. There are no lengths kids won't go to to talk to friends without prying eyes. The harder you try to lock it down, the dodgier their solutions will be.
Stu@mttaggart Kids in our school figured out that while the main domain of a popular console was blocked, the cloud streaming subdomain was not. Thus, Fortnite on Chromebooks.
Devlin 
@tehstu @mttaggart back in the early 00s I learned how to bypass the school's blocking to get on sites that were banned, in response to this I was taught the bare basics of linux by the IT techer who maintained said blocklist, as well as a week's ban from the library so it looked like I was being punished.
Patrick Loftus 🖖
@tehstu @mttaggart Our school canceled a computer class. It then became a study hall. We turned it into a game of cat and mouse installing Quake II (Action Quake Mod) on the devices. They deleted everything and prevented installs. We made self booting CD-Rom versions and continued to play.