This is for folks who are running Plex Media Server on server versions of Windows such as Windows Server 2012 R2. a few things to make sure are done to help a successful install
- install all available Windows updates
- install the 'media feature pack' or the 'desktop experience' (which, depends on the version of Windows Server). This will give you the prerequisite "Windows Media Player" or more precisely, its codecs.
- enable automatic updates of 'core' certificates (see https://serverfault.com/questions/541922/where-to-get-root-ca-certificates-for-windows-server-now-that-microsoft-no-longe ) The Plex software itself is 'signed' with fresh certificates. Without up-to-date 'core' certificates, the Plex certificate will not be trusted by Windows. Up-to-date core certificates are also necessary for secure communication with plex.tv and other internet services (metadata sources and/or all websites which are accessed by Plex 'channels').