Is iTunes open when you plug in the Shuffle? If not try that.
If you still have a problem then let's try running the iTunes program as Administrator (sort of expanding on what xema said above). Right mouse click on the icon or menu option you use to start iTunes. Choose the option to Run As Administrator. Then try again by starting iTunes first and then plugging in Shuffle. Does that work?
If it does then you could try removing the check to Run As Administrator (you may have to go to Properties to do this). It may have just needed to run that way the first time you synced. If the problem recurs then you will have to keep that setting (at least until their is some iTunes "fix").
Let me know if you have a question.
bol
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by: xemaPosted on 2008-04-07 at 08:18:39ID: 21297739
It may be that "current user is not an administrator"
Or you may need to change the security settings as it's possible that vista is not letting you to write to an USB device.