Automatic Sign In Setting Not Working

I recently upgraded to a new machine (Mac Mini) for my Plex Server. I moved all the database and pref files over and everything is working perfectly except one minor thing. When I use Plex Web on other computers to access Plex it asks me to login with my pin every time. I have tried checking the “Automatically Sign In” box in settings but it doesn’t seem to save it. Once I close the browser and reopen it asks me to enter pin again.

I have notifications turned on for iOS and I get a notification that a new device has logged in so it seems like it thinks it’s a new computer each time even though its not.

Server Version#: 1.16.6.1592
Player Version#:

I thought this was a player setting. It works for me on Macs and iPads. I would check the box, save settings, exit player, and post my player log if there’s something in there. Maybe it’s the server log, but I’m too lazy to look.

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