I signed up for iTunes Match on my MBP about a week ago. I started switching out my imported music (99% from CDs) to matched versions. Sunday while driving to work I went to play some music from my iPhone and it skipped through a lot of them while giving me a download icon thing. It looks like the only songs that are working are ones I purchased or got free (Starbucks App) from iTunes. Any idea what's causing this and how to fix it? For me, it's looking like iTunes Match is not a good buy. In the picture I have Airplane Mode on to see if it's checking iTunes to make sure the song is legal. Even with iPhone connected to Wifi I cannot play this music. In iTunes I have it checked to sync all my music to iPhone and it's taking up a large amount of space.