Good to read things are working again.
A claimed server periodically checks with plex.tv for updates. Unsure why your server did not indicate an update was available.
You can subscribe to the Plex Media Server Announcement Thread to be notified when new versions are available. At the bottom of the thread change Normal to Watching.
Plex Media Server on Windows has an option to automatically download updates in Settings > server_name > General. You may have to click “Show Advanced” to see it. See https://support.plex.tv/articles/200289496-general/.
I do not know if Plex will automatically install the update. I run Plex on Linux and auto downloading of updates is not supported (There are non-Plex ways to auto-update, but I do not use those options).
