Cannot Disable PIN / Automatically Sign in Disabled

Server Version#: 3.108.2 - Windows 1903
Player Version#: Fire TV / Browser / Plex 1.0

I have two Plex servers running on different accounts (one at home and one at office) and a friend shares his server with me. All 3 servers are requiring a PIN on players. The Automatically Sign In setting does not hold. I check the box, click save, and then when I come back 20 minutes later, I have to enter PIN again. All devices ask for it, all 3 users require it. I can only reset the PIN for one user. If I sign with one user I can access (home user) and then switch with MORE>, I can get into other users without using PIN again.

I have uninstalled Plex Server and reinstalled, restarted everything several times. I even tried intentionally toggling the setting off and back on. It seems like the other users are somehow affecting mine. Completely confused and not sure what to try next. Any ideas?

That setting is for that specific device only. You need to enable that on each device you use.

Or each browser you use on any one device.

Sign in Automatically is already selected on FireTV, but it still asks for PIN. Devices do not always appear to have consistency in this setting’s retention of behavior. It asks even when the setting is on or the setting turns itself back off on its own, depending on which device I try.

You are not switching between user profiles, are you?

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