I can't drop certain playlists into my Shuffle

I create playlists for each new album I import into iTunes. When I select the contents of certain playlists and drag them onto my iPod in the "Devices" area, the songs will not copy. This is only an issue with certain playlists. I can play the songs in iTunes with no problem, and I have been able to copy these same playlists to my iPod in the past with no problem. This didn't happen until I downloaded the latest version of iTunes. I've already reinstalled iTunes and restored the software on my iPod. Any help?

I just bought an ipod shuffle and when I go to play
the songs I don't hear anything. I loaded the songs
through iTunes and did everything like I was supposed
to, i even tried 3 different pairs of headphones. I
can click on the content tab and see that the songs
are there, I just can't hear them. I have tried the 5
R's but they did not work. Any suggestions? I am
getting frustrated!!
While you're clicking around, try settings Settings tab and make sure the maximum volume limit slider hasn't been set low... UNcheck it.

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