This seems to be a common issue, discussed often on the Plex forums: In my case the bad update is Version 1., but this seems to be a recurring issue for multiple other versions as well.
Very annoying to try to watch media only to find that the Plex server is not running. The automatic update feature is hitting this same problem, and thus regularly quits my Plex server and never restarts it. It alerts me again to "Download Updates" and "Install Update" - but the update never works. When I manually open Plex again, it boots up immediately as if nothing happened.
The server "Plex" is installing an update Plex immediately quits, and the spinner says that the update is installing: I want to update Plex via the "Install Update" button within General settings:
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