iTunes: some songs won't load onto iPod

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Hello all. I'm having an issue with my iPod, some of my original songs, mixed down from Logic Pro 7, won't load onto my iPod. They show up and play fine in iTunes, and in my ipod's list of songs within iTunes, but once i unplug and carry my iPod away to listen to, the songs don't play. I thought maybe it was the Info settings, so i entered in composer, year, etc. Still no dice on some of them. They were mp3's. Any idea why this is happening, how i can resolve it? Thanks so much for any help!
 
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MacBook CoreDuo 2Ghz 768M RAM
When you connect the iPod, does it automatically sync? Do the songs get copied over?
 
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Do they just skip on without playing but show up on playlists?
 
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Christopher
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Hi. Thanks guys. Yes, both are correct. Itunes starts syncing right away when i connect, and yeah the songs show up in my iPod playlist. Just won't play on the actual device when i disconnect it.

I don't know if it would show on the device itself, as this is an iPod shuffle. One other piece of info I should have given: this is iTunes 7.5

I'm grateful for any help on this. Thank you!
 
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iMac | iPod Shuffle | iPhone |
Hmm, I have an iPod Shuffle too.
I've never had this problem though.
Maybe the space is full?
There's gunk in the port?
 

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