Ok, so I turned off iTunes Match, so I can have the songs on my iPhone. Upon turning off iTunes Match on the phone and in iTunes, I went and told iTunes to sync my music. Here is how it's setup Sync Music Selected playlists Picked my playlist (Music) Hit Sync. My 'Music' playlist has around 160 songs. After I synced my iPhone, it only synced 78 of the 160 songs. After looking at the 'Music' tab in the iPhone, within iTunes, it shows this. I don't know what the little icon on the left means, next to the check mark, I'm a little stumped on this one.