So I've imported an audiobook into my iTunes library.
It consists of 4 CDs with about 11 tracks each. I've given them the proper author info and album info. I also gave each CD the proper number before import, and then iTunes did the rest by importing the tracks as Track 01, Track 02, etc… And giving them track number data in the info. There's 44 tracks total between the 4 CDs. They started importing to iCloud, and everything goes fine until just one track (Track 03, disc 4) decides it doesn't want to upload. It has the duplicate icon. When I click it, it says "This song is already in your iCloud Music Library." The problem is that there really isn't a duplicate. That file hasn't uploaded to iCloud, as I can see every track but that one from my iPod Touch with iCloud music. I think it may be thinking it's a duplicate with one of the other Track 03's in the album, even though the Get Info data differs in CD number.
Could this be what's going on? Is there any way I can fix this?
Here's basically what it looks like 
I have right clicked that one track and clicked Add to iCloud Library, and it begins to try but then it goes back to the Duplicate icon and error.
Best Answer
First what I did was create a backup of the media folder (containing the imported files) under
Music/iTunes/iTunes Media/Music/ARTIST/ALBUMThen, I just deleted the entire collection on iTunes (Choosing delete songs instead of remove downloads). This deletes the copy store in iTunes folder, but not the backup I created.
Last, I just refreshed iTunes by going to
File > Add to Library > (backup folder), and it copied the files back in, add uploaded them all at once, which solved the problem.