iPod: What to do if Windows displays an "itunes.exe - Corrupt File" message
If Windows has difficulty reading information off iPod or iPod shuffle, it may display a message from the System Tray, indicating there's a corrupt file and to please run the Chkdsk utility.
[Här visar de bilden som du bifogade, fast på engelska (orkar inte lägga in den ^^)]
We recommend using the latest iPod Updater to restore iPod because this will address the file system issue and will also defragment the iPod drive. Although you can use the Chkdsk utility to fix file system errors on the drive mapped to iPod, Chkdsk will not defragment the drive.
Warning: The restore process cannot be undone. All of your songs and files will be deleted. Always make a backup of your important data.
Tip: Make sure you always eject iPod properly and that you wait for the orange light to stop blinking before disconnecting iPod shuffle. Click here to learn more about iPod shuffle status lights.
This issue may be more likely to occur on iPod shuffle if iPod shuffle's file system has become heavily fragmented. A restore will eliminate fragmentation. Chkdsk will not.