Q: iCloud - two songs, same album - one Matched, one Ineligible. How to fix? I have 250 songs marked Ineligible, and I can't figure out why.  They are all 128kbps or greater, way less than 200MB, all Protected AAC audio files purchased by my ex.  I am authorized on his account and can play the songs in iTunes just fine.  In most cases only one or two songs from an album were rejected, while the rest were Matched, though some entire albums were rejected.
The advice online for fixing this centers around telling iTunes to convert the file to AAC, but in this case it gives an error that protected files can't be converted to other formats.  It seems most people with this error have low bit rate files, but that is not the case this time.
Is there anything I can do to fix this short of getting the unprotected files from him (which he would be fine with, but it could be years before he gets around to doing it)?
