iPod for Windows: Connecting multiple iPod devices to iTunes
While iTunes for Windows allows you to connect multiple iPod devices simultaneously to the same computer for charging, you cannot sync your data from the computer to all the iPod devices at the same time.
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Although FireWire and USB connections will allow multiple iPod devices to be connected to the computer at the same time, iTunes for Windows works best with only one iPod connected at a time. If you plan to connect multiple iPod devices to the same computer, eject any iPod devices that you are not using from iTunes.