Select the "iPod" tab from the left side menu of your iTunes.
Click the "Music" tab in the main "iPod" menu and select "Sync" at the bottom of the page.
Allow a few minutes for your iTunes to download to your iPod classic. Disconnect the two devices once the iTunes display reads "OK to disconnect." You will now be free to access your new iTunes catalog on your iPod Classic.
When using iTunes on Windows Vista, you can download your entire library to your iPod Classic in much the same way as you would with most other systems. Your iTunes catalog can be synced to your iPod from Vista and downloaded in just minutes from the software that's already on your computer.
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