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Discovery Issue

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I have ONE shared user who can't access my Plex server. This user was able to access everything fine until a little while ago. Time frame when it became inaccessible unknown but seemed to coincide with Plex for Roku update or at least when they noticed it.

PMS Version 0.9.12.12 on Mac OS X 10.10.5 (downgraded to 0.9.12.4, 0.9.12.7, 0.9.12.11 and the issue was seen on all those versions as well)
Plex for Web can't discover the server either directly (IP:PORT/web) or plex.tv/web
Roku app or Classic Roku app can't discover the server.

From my firewall logs, I see the connection being allowed and NAT forwarding the traffic to the Plex server. I reviewed the PMS logs but I'm not certain how to track how PMS is responding and if its proper. This, I think, is where I need some help.

I've tested this user from other systems on the outside and it works properly so I know its not the user account not having proper access to my server through myPlex.

I've also given this user access to another PMS server running 0.9.12.4 on a different network and that user can access the PMS just fine.

TL;DR One user connecting to one PMS can't get access. HELP be troubleshoot!


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