Plex Optimization isn't working

Server Version#:Windows 7
Player Version#: 1.16.6.1592

So I’m stuck with 4 movies that don’t want to optimize. I have had no issues in the past. I have no idea why, all of a sudden, it stopped working. I did, however, upgrade the Plex server the other day when promtped.

There are no error messages. I simply click “optimize”, click the down arrow and select “optimize for TV”, create the optimization “in folders with original items”, and press the “optimize” button. I’m greeted with a message that states, “This media is being converted.
Watch the status of the conversion here.” along with a green check mark. It immediately shows up in the “converted” section but no file/folder is created. There is plenty of disk space and I’ve rebooted. Again, I’ve never had any problems.

I would love to hear from someone who has a similar problem or knows how to troubleshoot. I’ve included logs, minus the verbos logging, and a screenshot showing that Plex believes it has created the file.

Plex Media Server Logs_2019-09-21_13-55-13.zip (2.8 MB)

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