Strange remote access behaviour

I was previously using a self signed certificate and specifying a custom domain name. I just uploaded my LetsEncrypt certificate that lives on my proxy to Plex (just in case it did not like my self signed one) and the results were the same. From the logs below it appears that Plex was able to load my certificate and did not complain, but the Plex service is still trying to access {ip}.{uuid}.plex.direct when attempting to enable Remote Access.

Jan 07, 2017 01:05:01.387 [0x7fffeb600700] DEBUG - CERT: Loaded a user-provided certificate.
Jan 07, 2017 01:05:01.387 [0x7fffeb600700] DEBUG - CERT: Requesting OCSP response from ‘http://ocsp.int-x3.letsencrypt.org/’ for stapling.
Jan 07, 2017 01:05:01.388 [0x7fffd0e00700] DEBUG - HTTP requesting GET http://ocsp.int-x3.letsencrypt.org/MFMwUTBPME0wSzAJBgUrDgMCGgUABBR%2B5mrncpqz%2FPiiIGRsFqEtYHEIXQQUqEpqYw R93brm0Tm3pkVl7%2FOo7KECEgPPnoD%2FIjRcHp7T91EGODtmug%3D%3D
Jan 07, 2017 01:05:01.485 [0x7fffd0e00700] DEBUG - HTTP 200 response from GET http://ocsp.int-x3.letsencrypt.org/MFMwUTBPME0wSzAJBgUrDgMCGgUABBR%2B5mrncpqz%2FPiiIGRsFqEtYHEIXQQ UqEpqYwR93brm0Tm3pkVl7%2FOo7KECEgPPnoD%2FIjRcHp7T91EGODtmug%3D%3D
Jan 07, 2017 01:05:01.485 [0x7fffd0e00700] INFO - Successfully retrieved OCSP response