In small towns there's often no choice. There's only one high school in Santa Fe.

Funny story.. back in 2000 a new boss starts at UK govt agency with student focus. This is around University entrance time. He wants to stamp some authority and show he knows better than the last boss. To add some context he was a Londoner in Scotland who obviously knew better than the great unwashed north of the border. Pretty much the first thing he does is look at the flagged words list on incoming emails. Why he felt this level of micromanaging would endear him to his Scottish team is lost to time. Anyway, he snorted and with a smirk berated the admin team for leaving out "cunt" and told them to add it in. The admin team, said nothing and did what they were told and waited.... Over the weekend over 10000 emails were flagged and had to be manually read by the small admin team, who were used to a small amount every week. Our London friend handed his notice in within 6 months :)

There's plenty of space for triggering false positives.

"I wonder if I'm gay.", "I read that if you drink bleach it could kill you", or just meta "what happens if I put the phrase XYZ here?".

Sounds like a good opportunity for a civics lesson. Today's subject: mass civil disobedience.

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.