Plex, pfSense, OpenDNS and DNS Rebinding

I’m starting to use pfSense a lot more at home now, making use of the advanced security features rather than it just being a router. I got quite frustrated last night when my girlfriend and I sat down to watch a film on Plex to discover that my Xbox One (Plex Client) could not see the Plex Server that was sat right next to it, on the same network. Further investigation proved that neither could my smart TV. I could access the server remotely via the Plex web app, so it wasn’t a port forwarding issue – I had already allowed 32400/tcp through pfSense to the Plex server anyway.

It turns out it was some security protection against DNS Rebinding. DNS Rebinding attacks are where someone directs you to an address which resolves to an internal IP. Loads of appliances and broadband routers use this functionality to present you with captive portals, and so on. I had seen a lot of people having similar trouble with Plex behind pfSense, so I followed the instructions. In fact, Plex themselves even provide you with instructions on their How To Use Secure Connections support page.

Actually, you should follow the DD-WRT dnsmasq instructions if you use the “DNS Forwarder” on pfSense as this is dnsmasq. The config line goes in Services -> DNS Forwarder in the Custom Options section, like this:

So, I had configured pfSense as Plex support advised, but I was still unable to connect to the server. Eventually I read up on how the domain name is used. When you log in to your Plex account you’re granted an authentication token which looks like any other guid (some long random hex string). The Plex service creates a wildcard HTTPS certificate for * which is unique to your account. It then tries to access your Plex server at https://ipaddress.guid.plexdirect:32400/ substituting the dots in the IP address for dashes. So such a URL could look like

I saw this URL pop up in the Developer Tools -> Network section of my browser when using the Plex web app at with some security warning or other. When I browsed to that address, I got an OpenDNS page saying that it had blocked some malware!

That’s right folks, I’m also using OpenDNS and it also has some DNS Rebind protection built in! It can be completely disabled via Settings -> Security and unchecking Suspicious Responses. However to retain the layer of security OpenDNS was providing I created a “Never block” entry under Settings -> Web Content Filtering for which seems to have done the trick.

The 2 lessons here are

  1. When employing a multi-layered approach to security and creating an exception make sure you create the exception at every layer
  2. Never assume that you know how network protocols work because someone will always find some obscure way of using totally standard stuff that makes no sense.