Version 1.112.0.359-0d79a49f#:
Player Version#:
<If providing server logs please do NOT turn on verbose logging, only debug logging should be enabled>
The windows auto updater can be flaky at times due to how windows processes background updates.
If you reboot the server does the update ever get applied?
If you mean restart the server. No it never gets applied.
With windows this is an easy fix, just download the newest version, and run the setup.exe and it will update Plex
