If you bought it from the iTunes Store, it's not mp3, it's AAC.
are you using iTunes 7.2? You could be running into the bug of AACs being reripped as MP3 not transferring to the iPod. (reported elsewhere on the forum)
Removing the problem songs from iTunes and readding them seem to fix it (at the problem of losing playcount/rating/date added).
Another thing you might try is to deauthorize your computer then reauthorize it and see if that helps.
More discussion on this bug in an original thread reporting it: http://forums.ilounge.com/showthread.php?p=1108715
Make sure you talk to apple, you are going to need to send back one of those shuffles

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I think, so far it looks good. I've been on the phone with Apple for 30 minutes now. My problem was this...2nd gen. shuffle. Had music on there (that was downloaded from Itunes) and was working perfectly for months. Then this morning I went to add some music and it gave me an error message that some music cannot be played on the shuffle?? It's the same music that has been on there and been played numerous times!
All music is in MP3 format.
I called up, they had me restore 3 times and asked if the music it won't allow me to add is only music from Itunes...yes it was. But, there is other music that I have downloaded from Itunes that will upload to the shuffle...that's when they said they're sending a new one.
Guy said this is a very unusual case that is why it is taking so long to complete the call.
FYI all...don't let this stuff go!