We've been dealing with the same problem today (Using JAMF Pro). Occurs on our enterprise WPA2 wifi but not on any personal WPA2 PSK AP we try. We noticed the wifi dropping out and the user having to sign back into the wifi if they were a new user and the setup process to change the password was triggered. This, along with the fact we needed to trust the wifi certificate manually made us think the problem was due to the user needing to trust the certificate but the trust message not getting shown (probably can't be at the point it triggers) was breaking things. We seem to have it fixed now by including the wifi settings for the enterprise network along with the chain or certificates (root down to the actual wifi certificate) in a configuration profile that we send out to all the devices. Now we can log on without any problems. ... View more