Summary:
I know some people have a lot of trouble with Downloads still. I’ve found something that might be one of the reasons why.
With some pretty conclusive testing I have determined that Downloads will always fail if the file’s name or path are too long.
That could explain why Downloads are very unreliable for some, and fine for others. It seems to depend on the filename/path length to the Downloaded item.
I’m unsure if the problem is specifically in the length of file name, or if it’s the length of the file’s full path. The files have no issue appearing in the library, so it’s specifically related to Downloads.
My Discovery Process:
I asked my server to download 1 season from a series. The season failed, telling me to tap to retry. Retrying continued to fail.
I removed that season Download and tried again with each episode individually (6 episodes). 2 out of 6 succeeded, the other 4 told me to tap to retry. I noticed the 2 successful files had shorter filenames than the failed 4.
I removed the 4 failed files from my library and replaced them with the same files but with shorter filenames. Plex found the new files.
When I ReDownloaded the season, all files worked immediately.
For testing purposes, I removed the Downloads, then I renamed a random selection of those episodes to have long filenames. Those chosen files with long filenames failed to Download.
