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What can you do if the school has a whitelist of domains they accept HTTPS (443) connections for?
That's got to be extremely rare. Not much you can do in that case. But they will hit many problems with that approach.
I will try to investigate further, but for instance if you go to duckduckgo.com, it says something like "this website is not on our whitelist, let us know if you think you need access." It's very annoying, so I avoid the WiFi when I can.