I am now thinking this has something to do with the accounts built into the Xbox.
When I log into the Xbox with my account (Live-Gold), and open up Plex (Lifetime Plex Pass Member), I am prompted for a pin. If the accounts stay that way, all seems to be fine.
When either of my kids log into their Xbox accounts (both Live-Gold), and they open up Plex, they have to enter in the pin as well. Once they complete this, if I go back to my account, I will have to enter the pin again.
Think I found a solution to (and the reason for) this. Looks like Plex only allows the account to be signed in to one Xbox account. Signing into a second will sign you out of the first. I have 2 kids, each with their own Xbox account. I have my Plex (Plex Pass) account and I created a second account for the kids which I shared their libraries with. Trying to sign both kids into the same Plex account resulted in being asked for the pin each time. So I created a second Ex account for the kids and all seems to be fine.
So, sign in to the Xbox on your (Plex Server) account and sign in with your pin. Then sign in with the username and password for each of your children’s accounts.
Hopefully Plex enable proper account switching on Xbox soon but until then, this should work for you.
