IPod won't transfer music but is syncing

I have installed iTunes 9.0.1.8 and have restored my iPod shuffle as it was accidentally formatted by Windows a while back. iTunes says my iPod software is up to date (software version 1.0.4). When trying to copy music across or autofill, the first message is "waiting for iPod..." it then says "syncing iPod" and then the Apple logo is displayed in the message box but no songs were loaded on the iPod. Not even the settings are saved, the same messages are displayed but the next time the iPod is connected, none of the settings have been kept (such as "enable sound check"). Can anyone tell me how to solve this problem - extremely frustrating? Thanks

Ya this is a long time problem with the iPod. My older 30GB original 5th generation iPod did it occasionally but doesn't do it much anymore. It seems to be related to the order in which you unplug the headphones with pausing/stopping. My older iPod may have a bit of a worn headphone connector since it doesn't usually pause the iPod anymore when I pull the headphones, so I wonder if the old one doesn't do it (your problem) anymore since the auto pause feature doesn't usually work?
Now with my new 80GB iPod, where the headphones do auto pause the iPod, I have been getting this issue a LOT lately. I haven't really done an extensive test yet, but it appears if I pause my music first then pull the jack out, it happens. I haven't determined yet if the order of HOLD ON then headphones or Headphones then HOLD ON has any effect. But so far in a couple tried, pulling the headphones while music is playing, forcing the iPod into Pause, then putting the HOLD ON, I have not had a problem. But it has only been a few tries in that order, so the jury is still out.
Patrick

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