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How do I download songs to my iPod Shuffle without deleting the songs that are already on it? When I try to download songs, it gives me this message:

Are you sure you want to remove existing music and audiobooks from this iPod and sync with this iTunes library?

[Remove and Sync] [Cancel]

I just updated iTunes to version 11.0.1. On the previous version, iTunes didn't try to delete the files I already had on my iPod.

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2 Answers

In iTunes choose the "manually manage music and videos" option for the iPod. This should allow you to add/remove/edit music and playlists on that device from any machine.

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You have two options.

One is to simply connect the iPod, choose not to sync, select the songs you want to transfer, and drag them to your iPod. That should copy them without syncing the whole library. You can also go into the iPod from within iTunes, and you can choose options in the various categories (like music, photos, movies) and choose not to sync them to be sure they won't be touched.

Your other option is to transfer everything from your iPod to iTunes and then sync. See this Apple support document for information on how to do that. Once everything has been transferred and is in your iTunes library (and be SURE that anything you want to be on your iPod is also in the iTunes library), then you can safely sync and ignore the warning about everything being deleted from your iPod (since it will be re-added during the sync).

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How do you drag songs to the iPod? In iTunes, the icon for the iPod is on the upper right, and it's a button that you can't drag songs to. (I've tried.) –  Joe Dec 28 '12 at 14:11
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When I drag songs onto devices shown on the upper right, there's usually a right-hand sidebar that pops out that lets me drag the song there. Otherwise, you can make the left-sidebar visible like it was before by going to View > Show Sidebar. –  kal-al Dec 28 '12 at 17:56
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