I run in to this issue every so often, would really like to be alerted when it happens.   Any update on this? ... View more

Assuming you are using Active Directory; it is common to deploy Microsoft CA server.  This will create a group policy that causes all your clients to trust its root certificate.   You can also great your own group policy to trust any root certificate that you want to use for WiFi.  Note that the RADIUS server can not use a self signed certificate - it needs to be signed by a seperate root certificate.  You can also use group policy to auto-configure the WiFi settings. ... View more