I have 1845 songs in my library and all but 1 were either matched or uploaded. The 1 song is nearly 15 mins long and that's the only stand out thing about it. I've tried deleting the song and readding it. I've re-ripped the track in various ways. I downloaded a copy of it. No matter what I try it won't upload just this one song. Anyone else see some limitation for song length? It meets the quality restrictions in every way that I can find. So odd. EDIT: Think I just answered my own question actually. I added a few other songs that were even longer. One of which is 28 mins long and those matched fine. Why in the hell would just the one do this? Says "This item is not eligible for iCloud" but it's just one track out of a album that the rest of the songs are and is available in iTunes currently.