Media Server Will Not Update

I strongly advise you to perform at least a health check of your Plex database. Performing a full database repair procedure can’t hurt either.
These are the instructions for your current server software version:
(do NOT try to upgrade before performing the repair/check) Repair a Corrupt Database 1.22.0 and earlier | Plex Support

After the check is returning OK or the repair procedure was successful, do this:

  • Stop/quit/end Plex Server with the tray icon
  • deinstall Plex Server with the regular ‘Apps’ control panel of Windows
    (do not use 3rd party ‘Uninstaller’ software like Revo etc.
    do not use “Registry Cleaner/optimizer” software like CCleaner et al)
  • for safety, reboot Windows
  • download the installation exe of the newer version and install it