Hard disk corruption when I autofill?

When I plug my shuffle in and hit autofill, it only fills up to 1.3 gigs or so. Then, I get a big yellow triangle in the Windows XP Taskbar saying there's been a serious error. I then receieve messages telling me that my external disk where all my music is stored (the "J" drive), has an error. It comes up something like, "J:/$Mkb" or some other weird $ name cannot be created, and data was lost. iTunes then loses all of the songs (has the "!" by all of them). I then proceed to check the hard drive, and all of the data is missing. When I remove the shuffle and restart the computer, all of the information is still there.
Why is the iPod Shuffle causing corrupt synchs, and messing with my drive? Should I reformat the iPod?
Although my info says otherwise, for this sync, I'm using Windows XP Sp3 on a Compaq Presario SR1103WM. My iPod Touch works fine and doesn't do this.

I learned that the shuffle halts the bootup process because there is no system file available on the device. Which is of course a reasonable explanation.
I decided to check the Windows Event Logs. I found:
"Application popup: Windows - Delayed Write Failed : Windows was unable to save all the data for the file J:\$BitMap. The data has been lost. This error may be caused by a failure of your computer hardware or network connection. Please try to save this file elsewhere."
"Application popup: Windows - Delayed Write Failed : Windows was unable to save all the data for the file J:\$Mft. The data has been lost. This error may be caused by a failure of your computer hardware or network connection. Please try to save this file elsewhere."
Dozens of errors including: "An error was detected on device \Device\Harddisk5\D during a paging operation." under the disk source
Error: "{Delayed Write Failed} Windows was unable to save all the data for the file . The data has been lost. This error may be caused by a failure of your computer hardware or network connection. Please try to save this file elsewhere." under the NTFS source
Error: "The system failed to flush data to the transaction log. Corruption may occur." under the ftdisk source.
None of these occur until I plug in my iPod Shuffle. I am forced to reboot my computer (minus the shuffle) in order to regain "lost" files.

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