I hate saying this, but it’s Apple’s fault in the way they played around with FreeRADIUS in 10.5 server.
I believe, that in order to use 802.1X easily Apple is using TTLS, which means your server needs a Certificate. If you use a self-signed cert, that your Mac clients will, correctly, not trust it. So you go and buy a certificate. Download it and install it into the System keychain on your server. The web server sees it. But RADIUS will sometimes have a spazz over the certificate. And even with a trusted cert, your clients can still complain if the certificate chain didn’t get installed correctly on the server with RADIUS.
If you add the certificate to the System keychain manually on your Mac laptops and tell it to always trust the cert, then it will make your life easy. Not the correct way to do it, but…
Or use Electron’s Radius server…
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