So, in short - im trying to get plex remote access to work both on and off vpn (never know when ill be out of the house whether the server will be connected or otherwise, so id prefer to have both working)
If I use the plex auto assigned 32400 all is well, can see it remotely etc etc. the issue is the vpn has that port in use by someone as theyre shared IP’s and we cant all be willing to designate our own ports 
soooo, i had to choose a port - which I did. The problem is, on or off VPN it shows as not being able to get in from the outside (except at first. it shows green then goes red after a second or two).
This is where it gets odd. Ive been taking my phone off wifi and using it to test and under both conditions (on or off vpn) I can access the server and media just fine.
So I figured - okay, the plex web app is just bugged aesthetically. To confirm I went to canyouseeme and to my chagrin, it shows the port as closed. Argh.
So ultimately I have no clue whats going on. Im barely savvy in this area as I use UPNP which works a treat considering how many devices I have going in my household, i cant be bothered to forward ports. Taking into account while I have a long lease time, and the IP’s generally dont change, they can - and probably will at some point due to some thing, and its just easier and more convenient for an old man trying to raise toddlers
i’ll take the security risk relative to the convenience provided.
That being said - also ocd about things working when I need them to SO, can someone help me with a plan of attack to sort this out?
Also, how exactly is it working fine remotely even though the website says the ports blocked, as does the plex web app?
Put your VPN-required things on a virtual machine. Then run Plex in either a different VM or the host itself. If you take that mess out of the equation, the UPNP should work without any trouble.
wanna talk about mess, that sounds awful
during some more “limited” testing as naaaaturally my kids have currently commandeered plex, it seems if I specify port 32400 manually as the external, it also works on and off VPN. However if i manually specify any other port - it fails on and off vpn.
the on VPN port failing i cannot explain. The off VPN port failing i also cannot explain apart from some kind of UPNP fail wheras it isnt with 32400.
the craziest part of all as i mentioned earlier, is even port checker websites are pegging the port as closed - yet im able to access my media from outside the network just fine.
truly lost.
even setting DMZ it falls on its face. perhaps i misunderstand how it works? Doesnt dmz open ALL ports?
this is OFF vpn im still getting green which quickly turns to red.
hrm, beginning to think its something on my end. What? who knows. I just opened a torrent client which requires ports to be forwarded, and it also works. yet when I go to canyouseeme and check the ports, they come back as closed. /boggle
is there another way i can check the ports? or something windows uses a service or feature i could have disabled tha twould be blocking proper acquisition or identification regarding whether a port is open or not.
wonky wonky wonky
Your trying to run two networks at the same time, One using a VPN the other as a normal home LAN, Plex can only connect to one at a time as most programs that require outside ports to be forwarded…
yea ive already spent another good solid full day digging into it. Its ultimately boiled down to the fact that my gateway/router combo from my ISP cant individually forward outside ports and inside ports so it will never work outside of using the autoconfig/upnp route. The minute i select a manual port it disables upnp and all bets are off due to the gateway.
Adding a new router to my shortlist and will end up having to put it into bridge mode or something. Until then I deal w/ the inconvenience.
