I renamed a bunch of files and this seems to have fixed the problem.
For context, I have a cron job that downloads YouTube videos from a play list. It checks for new videos added to the playlist every 2 hours and downloads them. I was naming the files with the template of `<title> [<id>].<ext>`. Since I'm using the video titles as part of the file name, I believe this is where my issues came from. Those titles can get super long.
That being said, what is the character limits in Unraid for file paths and file names?