Hi guys,
Thank you for the provided information. As I have had a very busy week with training and courses I was not able to do some in depth tests yet.
I did some quick and dirty testing with the information in these last 2 posts provided by you. I've tried various settings and combinations but all seem to fail.
I think the problem is somewhere in the Apple Configurator profile, as everything is working very well on my W10 machine. I have also tried on a Macbook but was also unable to connect. I will provide a more detailed log later when I have some more time at home.
Only thing what seems to be different in my setup is that I'm not using a self-signed certificate from a pfSense CA. There I was thinking it was not necesarry to add this certificate into the Apple Configurator profile. I'm using a Let's Encrypt wildcard certificate on my setup -> ACME installation in pfSense with auto-renewal, etc.. So I was thinking, like on my W10 it should work out of the box. However I did some quick tests with the settings provided by you guys (Machine Authentication, Server Certificate Issues Common Name, Server Certificate Common Name, etc..) but all with the same result.
Anyway I justed wanted to let you know I'm not inactive but currently have no time to perform further troubleshooting. I will update this topic further this weekend with more screenshots and error logs.
Thanks!