I will try that on my Macbook Pro when I get home, if I can figure out how to do it (some more detailed instructions would help. . .). The problem I'm having is songs I ripped from CDs into my iTunes library. The songs and CDs are all available for purchase on iTunes, so I'm not talking about some obscure music. iTunes recognizes them. Some of the songs from a given CD play; others do not. In two cases, entire albums won't play. were originally ripped from CDs into my iTunes library on an HP computer running Windows 7 (my Macbook doesn't have a CD drive). All of the songs appear and play fine there. However, the "grayed out" iCloud icon problem exists (and I can't play those songs) on my Macbook, my iPhone 5S or on my PC at work - which leads me to believe it's an iCloud or iTunes problem. . .