I prepare a poster for one of my library items. Due to a typo, I set the filename to \.jpg – literal backslash dot jpg. This is a valid filename on MacOS. I upload the image. Plex fails with an unknown error. Rename the same poster to zzzzz.jpg and upload it, works fine. I’m not totally sure why this occurs since the actual source filename should be totally irrelevant to the upload process, but obviously something in the code is processing the source filename and it’s erroring on this.
Reproduced on current Mac client.