Alright so.
It seems while watching anything on plex, whether it be the webapp, fire tv stick app, mobile, etc. Plex is losing connection somehow, until a restart is initiated, or if I wait about 10 minutes the server will be found again.
My setup is a little complicated but here it goes.
I'm running PMS-docker (I have tried both the official and the linuxserver/plex version) on a fedora 25 Host. That host is a VM on ESXi. The Fedora host has 8 CPU's and I've given the server 12GB of ram.
All Plex data is on a FreeNAS VM with 8 CPU's and 16 Gigs of ram, which has the SCSI controller passed to it via VT-d.
The ESXi host is plenty powerful but if really required I'll post specs.
All of the media is presented to plex via NFS shares on an internal storage networking switch at 10Gbps (i've tested the internal connection which is amazing).
I've also tested plex outside of docker installed directly and with local media, and I'm still running into the same issue.
This particular setup worked perfectly for me before the last few updates. Not sure if it's update related, just relaying that information
I don't know if this is a known issue with this version and I should revert to a previous version, or post logs.
If anyone has any insight I will be forever grateful.