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I have a variant to this problem and I cannot work out how to create a new post.
I have a Premium subscription.
I have synced all my songs to a iphone 5 with software version 7.0.4 some 400+ songs. (approx 2.0GB)
My phone still has 7.0GB of memory left.
They were all available offline for a 4 month period, up until yesterday!
I turned the phone on yesterday and now none of them are available offline and require re-syncing.
My Mac air book still has all the songs listed as offline and available for listening.
Why would this happen and I don't suppose there is a quick way to get them back is there????