Ipod flashes "do not disconnect", not recognized in itunes source - Help!

My ipod (2nd generation) continues flashes do not disconnect when connected. Recently upgraded to itunes 8. Have tried 5Rs including restarting service, renaming drive, reinstalling itunes, etc.
Also ran diagnostic, all test pass except sync test. Please help, any thoughts?

hi, thanks for responding so quickly. here's what happened:
1. i connected the ipod to my laptop and the DND (do no disconnect) message flashed on the ipod screen.
2. as u suggested, i clicked on itunes and tried to change its setting to automatic..it was on automatic already.
*laptop showed update was completed but DND message still flashes on ipod. I decided to check if everything else was working.
3. downloaded a song and when it was done i checked my itune page and library...song wasn't there.
4. i clicked file, add file to the library, browsed and found the song in documents/music/itunes.
5. clicked open then updated the ipod.
*update completed, DND shows on ipod, clicked eject, took out the cable.
6. menu showed on screen, all other songs were there expect for the last one i tried to transfer.
i don't know what to do now...?? could it be broke?
ipod   Windows XP  

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