dot1x connectivity - EAP certificate

I am experiencing an issue where iPhones will not connect to WiFi, the supplicant is timing out the connection and starting the process over again. When I first try to connect I am prompted for username/password, after entering that I am shown the RADIUS server EAP certificate. The odd thing here is that if I instantly click trust, the connection fails. If I let it sit at that trust prompt for 30+ seconds I will connect, everytime.

I'm curious if there are any best practices on signing a EAP certificate from Apple; Androids and laptops have no issues connecting. Apple devices that are already in our MDM and get the root CA pushed to them have no issues. The type of Apple devices does not matter and most of them are on 14.5.1