Plex on Xbox one is always signing out. I have to either sign back into plex or enter the pin. I also notice while watching a movie if I hold down the home button and turn off the controller it will also sign me out…that one is not as big as an issue as having to sign into plex everytime I open it and to have it say it’s to working go home or retry. I click retry and it doesn’t work I have to click go home then go to the top right plex icon and the clickon my server to get it to load. 
Do you have more than one user signed in with the same Plex account on the XB1, or another XB1?
See the pinned thread "How to use multi-user on Xbox one" at the top of this forum. It will probably solve your issue.
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