I am a Plex Pass member. Looking at the Now Playing section, it still looks the same. I also do not see Dashboard on the left hand menu, rather I see Now Playing still.
What am I missing here?
I am running Plex Server Version 1.14.1.5488 on Ubuntu 18.04
plex.tv always has the current version of the web app, the version that is on your server is installed with server updates and generally is not updated as frequently.
So I had the same issue as OP but a reboot didn’t resolve same, attempted what’s listed here, yearly Plex Pass but when viewing the dashboard it’s almost suggesting it can’t tell that I am.