Issue Setting Up Custom Domain: Not Working

[jayson.knight]

Longtime Plex user here, first time posting in the forums. I’m in the process of setting up a custom domain for my Plex installation, and am having problems getting it to work. I have correctly set up the certificate portion, with the following parameters:

1. The certificate is a wildcard cert for my TLD purchased from GoDaddy
2. Under Network -> Custom certificate domain, I put plex.mydomain.com which is the subdomain I’m going to use. There are no SAN entries on this certificate, it’s strictly a wildcard cert, but this has to match the subdomain, right? My concern is that since there is no SAN entry for the plex subdomain I’m using, this might be a problem.

Internally, I can access the plex server using plex_{.com with no certificate warnings, and I see it’s loading the certificate properly, so this isn’t the problem (though since the Custom certificate domain is specified as plex for the subdomain, my concern is that since this is a wildcard cert with no SAN for plex..com that this could be part of the problem?}

Also on the network page, I added https://plex.mydomain.com:443 as a customer server access URL, and changed the external port on the remote access page to 443. I’m using a reverse proxy, and have that configured to map the external URL plex.mydomain.com:443 to internaldomain:32400, bound to the same internal wildcard certificate.

Where can I find out where this is failing? I doubt it’s the reverse proxy as I’ve set up tons of websites with this same proxy with port mappings, my concern is that I’m not sending Plex the right info from the mgmt page? I’m not familiar at all with Plex log files/etc, so any guidance is greatly appreciated.

(software engineer/architect for 17 years, so get as technical as you want)

[jayson.knight]

Just a quick update: I’ve tried 3 different reverse proxy solutions, none of them are working. I think it’s the non-standard port 32400 that the server runs…what’s the reason this isn’t configurable?

If I remove the reverse proxy as the middleman and go straight from the router to the server, it works fine, but this isn’t a solution that is going to work. Also, the documentation on this is ambiguous: Where do I put the port numbers? If it’s an https custom URL, do I need to specify 443? If 32400 is specified on the remote access page, but 443 is specified in the custom URL, which one is used?

If you’re going to offer advanced features, offer advanced documentation because if someone is needing the advanced features, chances are good they can understand advanced docs. Hopefully somebody has figured this out and can give me some pointers, this shouldn’t be this difficult to implement vanity URL’s, and use 443 as a standard port for transit through the firewall.