I know it must be simple, but will not sync

The first time I plugged it in it synced 4 songs it found on my computer. The I bought a cd from itunes. That shows in my library, but does not sync. Thanks for any help.
dell Windows XP

I have a 2nd generation shuffle, and it accepts songs encoded in iTunes 7.0.2 from CD, but the 1st generation shuffle does not.
Just checked this out to-night, troubleshooting requires extra equipment sometimes.
This is on Mac OS X latest version, probably is the same for Windows...reset the shuffle, no luck, no change. The firmware update for the shuffle apparently doesn't relate to this problem, which is very frustrating.
I suppose Apple will bring out a fix to iTunes 7.0.2, which contains certain fixes ...problem can be solved by using previous version 6 something to encode CD, then it will be easy to transfer files thus encoded.
2 G4s, 2 Intels Mac OS X (10.4.8)

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Hi Amy2250,
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I know it must be simple, but will not sync

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