pfsense and plex

I’ve been having some issues setting up PFsense and Plex.
I have created the FW rules and Port forward rule as outlined here https://www.linuxserver.io/2017/05/01/how-to-run-pfsense-with-pia-vpn-but-still-use-plex-remote-access/

What is odd is that when I click retry on the connection in the plex remote access settings the setting turns green for just a second then flips to red again. This leads me to believe there is a clue in the plex logs. I looked, but I do not really know what I am looking for, if someone could take a look at the log data and let me know what I’m missing or what i causing the failure I would appreciate it.

Thank you,
RcCypher

@rccypher said:
I’ve been having some issues setting up PFsense and Plex.
I have created the FW rules and Port forward rule as outlined here How To Run Pfsense with PIA VPN, but still use Plex Remote Access... | LinuxServer.io

What is odd is that when I click retry on the connection in the plex remote access settings the setting turns green for just a second then flips to red again. This leads me to believe there is a clue in the plex logs. I looked, but I do not really know what I am looking for, if someone could take a look at the log data and let me know what I’m missing or what i causing the failure I would appreciate it.

Thank you,
RcCypher

Reboot plex. I have the same issues, rebooting Plex fixes everytime. I’ve had to reinstall plex several times and this fixes it everytime so you wont have the issue again

https://support.plex.tv/articles/206225077-how-to-use-secure-server-connections/

scroll down to the bottom

Also, try a different DNS server. (Google or OpenDNS for instance)
Many ISP-provided DNS services fail to correctly resolve the .direct TLD.

The DNS server was indeed the problem. I had a seperate DNS server setup to run DNScrypt based on this guide: https://ipredator.se/miniguide/dnscrypt/freebsd#installation
Though I added the config items discussed here: https://support.plex.tv/articles/206225077-how-to-use-secure-server-connections/
to the config file for that DNS server it did not resolve the problem. I suspect the upstream DNS server is to blame. Regardless I setup DNS resolver on PFsense with the advanced config item mentioned on the how to use secure server connections page. That pretty much resolved my issue.

DNSCrypt is, presumably, using opendns which barfs on local redirects. Very simple fix: under DNS resolver set “System Domain Local Zone Type” to “Type Transparent” and then add a domain override that directs the domain plex.direct to use 8.8.8.8 for lookups. If you’re using DNS forwarder, switch to Resolver.