Downloads vs. Sync –– 80% of "Downloads" won't play on iPad

You don’t have debug logging enabled in your server settings, so the logs are not very useful. I do see 1 message at about the time when the Download attempt was made. It refers to a subtitle file that could not be found. It appears to be one that was automatically downloaded via OpenSubtitles. So PMS still thinks the file is there but can’t find it when it tries to find it. This is preventing the Download from occurring. Can you turn off the OpenSubtitle agent, then Plex Dance that movie and try again?

If that works, you may have the same issue for your other movies. You can try doing the same for some other movies to test. Unfortunately, there isn’t an easy fix for this. Recreating your library would be the fastest fix. Or you could try upgrading the library to the new Plex Movie agent. That doesn’t use OpenSubtitles so it should remove all that extra missing subtitle info.