Help! Server won't play any recent additions to library

Good Day,
Long time Plex user here and I stated having some issues with my server starting earlier this week and I cannot for the life of me figure out the problem. I keep getting error messages for recent additions to my library and these items are unable to play. Error messages vary depending on the client (iOS client states - Playback Stopped - Couldn’t create the playback session for this item; Browser - Playback Error - There was an unexpected error during playback. Please visit our forums if you continue to experience problems).
The problem only seems to be effecting the most recent additions to my server. All the media files that I added prior to this week play just fine on all clients. I double checked that the media files were good and named correctly. They play just fine in a native application. I was hoping someone might be able to help me with initial troubleshooting steps and point me in the right direction. Thanks in advance!

Probably Analyze function no longer working. All new Video and Audio is "None" and won't play

Thanks for pointing me in the right direction. This seems exactly what I’m experiencing!

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