I also found it ironic that they call out https as something desirable and how kids can't describe why that is, but they don't have Let's Encrypt or something else setup for the very site where the otherwise great writeup is shared.

That said, it's possible that the network had an automatic configuration script for the proxy that would have configured on connection under Windows systems and he just wasn't aware that it would require manual steps on OSX? Still a bit ironic, but maybe excusable? I feel like if I managed a network with a proxy that would automatically configure on connection, I would understand the limitations of that setup, but that's assuming a lot? I'd love to see their explanation on why that was her fault rather than theirs all the same, because the first thing I do after getting someone connected to a network is attempt to access something unlikely to be cached just so I can validate that the task was completed successfully.

If your kid can't use wireshark, what's the point?