I need to update ipod software, but update button is faded

When I'm uploading music to my ipod, a message appears that says some of my songs aren't going to upload because I need to update. But when I try using the ipod updater, I only get the choice to restore, which I want to try and avoid.
Why is update faded out? Next to the version of iPod sotware I'm running it says I need to update but it won't let me. I'm following all the instructions that I can find but I'm still having problems.
This is a 15g ipod with the four buttons on the front. Please help! Thanks.

Incredibly I have been through this miserable scenario - and posted about it in another thread. I finaly succeeed in overcoming it. How you ask. Well ( and I am one who just bought a Mac and was thinking of switching for good) - a Windows 200 Machine running an old 4.x version of iTunes. Say's I said a Windows machine !
As soon as I dowenloaded and installed the updater it allowed me to upgrade - and I did to 2.3. So the probelem is either the Mac version or more liley 5.0 itself.
Now why oh why would I have to use a 4 yeard lod Windows 200 machine to update to the latest firmware on my Apple iPod, to make be able to play music that I purchased from the Appple store - somethng I could not do with my brand new Apple G5 anf Apple iTunes 5.0. I seem like I am repeating Apple again and again. Yeah ...right. good thing I didn;t throw ou that old Windows piece of junk huh ? Long live Bill Gates - simple, eee-gadds - dare I say user-friendly computing. Did I say that ?

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