I recently upgraded from an iPhone 4s on 5.1.1 (yep!) to an 6S+ and iOS9.3. I also subscribed to iTunes match but combined with the god awful music app is a nightmare to figure out. I prefer to drag and drop songs from iTunes to the phone but it appears if you have itunes match enabled, you must download the songs though iCloud instead of using itunes. But itunes match does not allow songs longer than 8 hours or 200MB. When I disable itunes match on the phone, it does something weird and removes a bunch of songs that were downloaded but leaves other songs. I can then drag and drop the 8 hour song into the phone and itunes "updates" the songs that were removed but doesn't transfer the 8 hour song. How am I supposed to transfer this thing? I have plenty of room and it is an mp3 file. I have transferred similar songs before getting itunes match.