In this context, I'd be encouraging my children to do this (and certainly take the blame for them); false positives ftw! It'd be a great, teachable moment where I can discuss many sociological, technological, and ethical issues at once. On top of that I can teach them a thing or two about opsec.

The school is really at a loss here for retribution: in many instance the students are required to use the school's equipment for completing assignments and projects. So the worst they can really do is "restrict" usage -- but that isn't really any different than what they already do. So it's a bit of a headache for me and the kid(s)? A small price to pay for demonstrating the hilarious shortcomings of implementing a technological solution to a purely human problem -- one that requires specially trained humans to fix.

(Of course I'd make sure the kid(s) give me their blessing before messing with the school)

On another note: I have extensive experience working for school districts. This is absolutely a CYA attempt with no foresight into what the outcome of this terrible experiment will be. These solutions tend to be hacked together, easy to circumvent, and poorly implemented. While I have no direct experience with the product mentioned, I do have experience with school-focused solutions. We had to pay the extra money for purely commercial solutions to get anything that was worth the money.