How come I can't transfer some of my songs from Itunes to my playlist on my Ipod?

I have an older 1GB IPod and am having problems trying to transfer by dragging and dropping certain songs from my Itunes library to a playlist on my ipod. Oh and this just starting happening after the last update to Itunes.  Does anyone know why this would be happening?

It is formatted for mac and I can place photos from iphoto but I can not even move the songs from my itunes to my desktop,my itunes will not let me move,export or copy any songs out of itunes

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    (18102)

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     Cheers, Tom

  • HT1473 How can I transfer my music (not purchased from Itunes) from my Ipad/Iphone to my new Itunes library on a Macbook Pro?

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    The iphone/ipad/ipod is not a backup/storage device.  The sync is one way - computer to iphone/ipad/ipod.
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