Can't transfer files to wife's iPod

Got a new computer. No problem managing files with my iPod using iTunes, but I can't transfer files from Library onto my wife's iPod anymore. When I connect her iPod, iTunes DOES seem to recognize the iPod--it displays her iPod and allows me to delete files from her iPod, but when I try to drag songs from Library onto her iPod, no dice (the circle with a line through it symbol is displayed over the iPod folder when I try to drop the file into it). Can anyone help?

I've a large file of 4.03 GB
If you're using your iPod with Windows, the FAT32 file system can only accommodate files that are smaller than 4GB no matter how much free space there is on your iPod

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