Optimize creating unplayable videos

That implies there is no MOOV atom in the file.

Is the original file a MP4 ?

If MP4, please consider making sure there is a MOOV atom in the file.

  1. save the original in a safe place
  2. use ffmpeg directly to create a MOOV atom for you in the file by having it “optimize for streaming”.
ffmpeg -i input.mp4 -c copy  -movflags faststart output.mp4

It performs two passes. you will see it writing a new MOOV atom at the front of the file.

When complete, put it in place and click “Analyze” in Plex to have it re-analyze the file.