Manually managing my music doesn't work

since i installed the last version of itunes, if i set it to manually manage my music, it doesn't work. i try dragging the files over to the ipod, and itunes says it's updating the ipod. the progress bar goes to the end, but the files never get copied. if i disable it, then files in the library copy over fine.
what gives?
  Windows XP Pro  

Hello, stashmore94. 
Thank you for visiting Apple Support Communities.
Usually the reason for interrupted, stalled or canceled syncing alerts is a result of either security software interference or TCP/IP modifications.  Also, non Apple cables and low powered USB hubs can cause this issue.  Here are a couple resources that I would recommend going through as they may help resolve the issue.
iTunes: Troubleshooting security software issues
http://support.apple.com/kb/ts3125
Apple software on Windows: May see performance issues and blank iTunes Store
http://support.apple.com/kb/ts4123
Cheers,
Jason H.

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