This has been an ongoing problem across many server versions and different Windows servers. Usually after a day or two, my Plex player can no longer see the Plex server. I have to go to the server and simply open the tool tray Plex and it seems to restore access. Running server on Windows 10. The player is either my iPhone or Roku. It’s like something is going to sleep, but I never lose Remote Desktop connectivity to that server.
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