@djrory Did you ever figure this out? I am also seeing something similar. I am pushing out WiFi through SCEP and a WiFi payload. I am also being prompted to "Trust" a certificate from our DNS. The other odd thing is that after I accept the WiFi connects but the cert can not be found anywhere on the device.

Any insight would be appreciated.

@JosephRecendez
Unfortunately not, still struggling with this. I am pushing the CAs, intermediate and WiFi certs via a config profile, they all appear as trusted but no matter what the iPads still prompt to trust the cert when first connecting to our corporate wifi even though it already has the EXACT same cert and all certs in the chain of trust.

I've basically given up on this now, resigned to the fact that we will have to manually setup and trust the wifi on every device... kind of defeats the idea of MDM...

I tried messing around with these settings but regardless of the configuration and trust settings it still prompts every time...

I am seeing the same thing. New SSL cert for Clearpass, new Intermediate and Root from Digicert, all in the WiFi profile. It is still Not Trusted on iPads and Apple TVs, and we are prompted to Trust...

I am also having a similar issue.   Except the cert I se is an example cert.  Anyone get answers on htis?

I have the same issue now in 2024 and JAMF doesn't give a solution since 2021... How did you solve/walkarround it?

Yeah, we did eventually find a way to have the iPads join an enterprise WiFi Network entirely automatically without the need for the end user to select the WiFi or accept a trust prompt. 
I honestly do not know what the change was, it just worked one day. Here's my config profile. 

For us it was me not seeing a screen. I had the certificate payload and the WiFi payload in the same profile as required, but I did not see the Trust screen to the right of the Protocols. I had to check the certs to trust them.