iPod not accepting iTunes purchases/won't let me restore

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I just realized that my iPod hasn't let me drag in any iTunes-purchased music or videos.

It says some items were not copied to the iPod. Check to see that my iPod software is up to date.

But the grey-shaded area in my iTunes/iPod Settings section is always greyed back, and says my software is up to date. I have the latest versions of software for both iTunes and iPod, and I can't restore my iPod b/c the button is greyed back. The only time I can restore it is if I plug it in at work and wipe it clean.

Can anyone tell me why my music and movies purchased on iTunes won't copy into my iPod? I've already been to the Genius Bar... they don't know.

Thank you!
 
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G'day trellame & welcome to Mac-Forums!

Can't say why you're having this problem but why not try Senuti (iTunes backwards FYI) or another iPod utility that allows you to drag'n'drop to and from your iPod?
 
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Your Mac's Specs
2.4 GHz intel core 2 duo MBP, iPhone 5, iPad 3
Pulse-8 as always has a great suggestion. Senuti will also pull video from your ipod and transfer it onto your computer.
 
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Thank you both, I will try these with my home computer and let you know if they worked!
 
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before I could even try Senuti, the next time I plugged my iPod into my computer and fired up iTunes, it wiped my iPod clean. And won't let me add any music to it at all. So frustrating...
 

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