I am mainly looking for Answers that suggest solutions to get the auto-updater working, rather than me manually downloading and installing the update from the Plex website. Logs are available, but I'm not sure what I should be looking for. Plex forum topics are shut down after 90 days of inactivity, and I cannot find any actual solution or explanations for this Plex Updater failure. This seems to be a common issue, discussed often on the Plex forums: The Plex Media Server lets users create a collection of audio and videos and stream it to other devices. Initially released in 2008, the software has extensive support with developers constantly working on bringing in new features. In my case the bad update is Version 1., but this seems to be a recurring issue for multiple other versions as well. If youre able to access the Plex server using a client on the same network but are unable to connect outside, the most likely cause of the problem is the router. If you are looking for a client-server-based media player, then Plex might suit your needs. 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. Some users report that the Plex library scan temporarily works again after doing a server restart. 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:

Plex media server update failed