I did this with a playlist that has over 6000 songs, but the "download all" feature seems to only download 100 songs at a time. After that, the rest of the songs just stay with the spinning icon, but never start. I turned off the auto lock feature, and am leaving my iPhone on the charger, and it still happens. I hit the download all button, nothing. I quit and try again, nothing. I have to restart my phone in order to download the next 100, and so on it goes. I even tried turning off iTunes Match to sync music the old fashioned way, but iTunes will not let me sync my music. I tried to manually manage my library, and only 16 of my 6000+ songs transfer. The rest of the music is greyed out, with a dotted circle symbol next to the rest of my library. Music was not purchased through iTunes, so Authorization should not be necessary. I am at a loss. Any help is greatly appreciated.