pfSense 2.4.1 - Can't connect to Plex Server

Up until yesterday I was using a Linux firewall/router and everything was working fine. After switching to a pfSense firewall I cannot connect to my plex server. When I open a browser and navigate to my plex media server (e.g. https://hostname:32400/web/index.html), I see the following:

"Looking for servers..."

"Please wait while servers are discovered"

"Connecting"

After some time the following is displayed:

"The server 'hostname' is unavailable"

"Plex will automatically try to reconnect to this server"

"Unable to connect to 'hostname' securely."

"Do you want to allow insecure connections?"

I tried switching from https to http, but it didn’t help. Based on a variety of posts in the forums I have also tried the following:

  1. Adding the following the custom options for the DNS Resolver:

    server:
    private-domain: “plex.direct”

  2. Adding the following domain override:

    Domain: plex.direct
    IP Address: ip address

  3. Adding a port forwarding rule:

    Interface: WAN
    Protocol: TCP
    Destination Port Range: From 32400 to 32400
    Redirect Target IP: ip address
    Redirect Target Port: 32400

Nothing I have done has seemed to help. Any assistance would be greatly appreciated.

It has been reported pfSense 2.4.1 breaks a lot of things. CDP and LLDP being but two. I am not surprised it’s broken stuff for you, sadly

I have my SG-2220 locked at 2.3.4 until such time as the 2.4 branch is stable. At this point, I recommend not upgrading any pfSense box until 2.4.2 or appropriate 2.4.1 updates are released.

Unfortunately, this was a new pfSense install and I just went with the latest release. I don’t really have the time right now to reinstall an earlier version. Is there anything I can do so that I can use my Plex server?

Remove the pfSense from the circuit and revert to your previous method. It’s the most logical step.

Reverting to my old router/firewall may not be an option. I was upgrading because it was having problems. Are there any known issues with using pfSense 2.3.5 with Plex?

Here is my status. it works flawlessly.

Did you need to specify “plex.direct” as a private domain in the DNS Resolver settings, or set up port forwarding?

Yes. This informs pfSense it’s not a DNS-rebinding attempt.

Thank you for your help. If I have some time this evening, I will downgrade to 2.3.5

I rebuilt the firewall, installing pfsense 2.3.5, and nothing seems to have changed. The only 2 packages I have installed are pfBlockerNG and snort. I disabled both of them, but it didn’t help.

Backing up… The Syno is on your LAN? If so, why not open it by LAN IP?
Next, Create a port forwarding rule in the pfSense to port forward 32400 to the IP of the Syno. This will allow you to enable Remote Access

The synology NAS is on my LAN. The pfsense box is my firewall/router. From a Windows computer on my LAN I am trying to access Plex via https://:32400/web/index.html. If possible, I would prefer not to open a port on the firewall as I do not need remote access.

I now seem to be able to access Plex from my Roku, which I couldn’t do yesterday.

If you don’t need remote access but want to do things via Hostnames,

Go into the pfSense DNS resolver and enter the names & addresses.

I have configured the DHCP server in pfSense to issue static IP addresses and register the hostnames in DNS Resolver. Also, while I seem to be able to access the Plex Server from my roku, I cannot access it from the Plex app on my android phone.

It sounds like you’re making progress reconfiguring your LAN and slowly working out your LAN issues.

Since this is not a Synology issue, I’m moviing this thread to the general Plex Pass area where others are more likely to see it and be able to help

Just for info - my pfSense doesn’t have what you have written in the DNS custom options - mine says:

“rebind-domain-ok=/plex.direct/” which was what was listed on the Plex website. I also don’t use my ISP for DNS resolving I use Google DNS.

To be clear - my configuration works flawlessly.

To be equally clear. I’m running 2.3.4 on the Netgate SG-2220 and the screenshot I provided was taken directly from it.

OK I did a quick bit of research to find out why I have something different to you - my entry is in the DNS forwarder not the DNS resolver (which I don’t use). I resolve DNS on another machine which runs pi-hole for network wide adblocking.

I put it in the DNS Resolver. I was told to do that by someone who works with/on pfSense every day.

My pfSense handles all local domain (mydomain.lan) resolution