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We have a number of iPods and a number of computers and the fact that they need to be matched one-to-one for iTunes sync'ing to work is really a pain.

Is there a way for me to upload a video directly onto an iPod Nano (a previous generation that can still play them back, not the current one), without having to switch the library it is connected with (which would erase all other content on there)?

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Another option is to manually manage music and videos. Click on the iPod in iTunes, check Manually manage music and videos. It will allow you to connect your iPods with your various computers without worrying about wiping them.

http://support.apple.com/kb/ht1535

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Here is a way to do it : Use the App "USB Disk"

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  • That won't work with an iPod Nano, though, right?
    – Thilo
    Commented Mar 12, 2011 at 1:16
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I'd take a look at PhoneView and iRip2. Both have demos. I have and use both and they are excellent.

http://www.ecamm.com/mac/phoneview/index.html

http://thelittleappfactory.com/irip/

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