We're making progress!
Looks like connection are being made, so it isn't routing after all!
Looking at the first recording, based on the different packet length, I'd guess it is doing SSL handshake properly; whereas the second one seems to be all 0 length and so something is not working out. At least on a cursory glance, your settings seems to be pretty permissive, so unless your friend's using a super old system, it shouldn't be an issue. Do you know what OS your friend is using, and if it has up-to-date root certificates? Are they on a system with openssl cli available? Judging by the unifi network, probably? Try openssl s_client -connect drkt.eu:443 -prexit (and ctrl + c to quit after it stops) and see if you can see any oddities with the SSL handshake process.