Remote Connection Works but web says "Not available outside your network"

Plex Media Server Remote Access
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Server Version#: 1.19.3.2852
Player Version#: n/a (but am using Apple TV, Plex Web 4.30.2, iOS 6.12.1)

I have been fighting this problem for a while now and thought I would seek more eye’s/thoughts.

I have 2 problems but care about #2:

  1. occasionally (but very rarely) the remote access seems to get turned off. Infrequent enough that I can live with it and others seem to have this problem looking at the posts.
  2. It keeps saying remote access is “Not available outside your network”.

#2 is what I am trying to understand and trouble shoot.

I have my plex server (ubuntu 18.04 box) on one network lan segment (10.0.5.12) and my desktop of a different lan segment (10.0.3.x - DHCP). I am running an opnsense firewall/router (10.0.3.1 and 10.0.5.1 and WAN dynamic IP).

When I hit the retry button on the remote access page it thinks for a few seconds, then shows green across the board. Another few seconds later it decides the internet to external IP connection doesn’t work and changes to the “Not available outside your network” message.

Why this is strange is that remote access works just fine. I can connect from my mobile phone, I can connect from my partners mobile phone (different mobile providers - and wifi turned off or away from home), I can connect from a friends house and my parents house. I know the port forwarding/NAT is working because I can see the firewall logs from the traffic and know which rule they hit. I can also telnet to the port from a server I have in a different country.

What I can’t seem to find is what is causing the change after a few seconds. I don’t see any blocks in the firewall logs, and I see everything hitting port 32400 (the logs are shown post destination rewrite) as allowed including what I assume are the test IP’s (34.248.59.52 and 54.171.49.143 which are Amazon IP’s in Ireland that I assume is part of plex’s infra)

I have manually specified the public port (32456 -> 32400) which is mapped correctly ( like I said, I do have remote access, its just that the web interface doesn’t think so.

I have attempted playing with or tweaking (but possibly not enough) on the networks page:

  1. Custom certificate domain (as I use a customer cert for the server)
  2. LAN networks list
  3. Custom server access URLs
  4. List of IP addresses and networks that are allowed without auth
  5. I have “Enable Relay” disabled

I am after any ideas, or any info around the logic used to check for connectivity (because it is NOT an accurate test of whether an external person can connect).

This thread seems very similar: Plex Server says that Remote Access it not working, but it works for all devices, except FIRE TV based devices?
Except:

  1. I am not using “Custom server access URLs” (although I have tested it)
  2. I am not using IPv6 (turned off in OpnSense and in Plex)
  3. I am not using Plex Relay/indirect connection (although I have tested it)

So I am curious what the other cases are… Any of the following?

I am using a custom certificate
I am using custom LAN Networks
I am using custom List of IP addresses and networks that are allowed without auth

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