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transferring songs from ITunes to IPod Nano

I have IPod Nano 5th Generation, and the latest IMac operating system.

Had no problems until today, because yesterday I downloaded the brand new ITunes 11.0 (163). Trying to transfer songs from ITunes to my IPod Nano. Not sure if I should submit this question in the ITunes section or the IPod Nano section, so did both.

ITunes used to - until today - show my device (IPod Nano and its playlists) on the left side column of ITunes, above the ITunes playlists. So I could just click on a ITunes song on one of the ITunes playlists and drag that song into one of the IPod Nano playlists above it. Now with this new version of ITunes nothing shows up on the left side, so I have no way of dragging songs from ITunes to IPod Nano. An IPod Nano icon does appear on my desktop, but clicking on it or its contents does not show any IPod Nano playlists. I could click on the IPod Nano icon on my desktop and then click on "all files" on top. There is an area that shows all the IPod Nano songs (I think), but it does not show the IPod Nano playlists.

1) How do I get the IPod Nano playlists to show?

2) Please advise how to transfer songs from ITunes to IPod Nano playlists when using this new ITunes 11.0.

3) If this cannot be done, is there a way for me to go back and reinstall the previous version of ITunes?

iMac, OS X Mountain Lion (10.8.2), iPhoto 8.1.2 (424)

Posted on Dec 12, 2012 1:59 PM

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4 replies

Dec 12, 2012 2:08 PM in response to Henry R

I checked again. Clicking on the IPod Nano icon on my desktop and then clicked on "all files" on top. There is an area that shows music, but it is music in ITunes but not necessarily music in my IPod Nano. I know this because it shows some songs that I just downloaded to ITunes but had not yet put in IPod Nano, so they cannot be in IPod Nano.

Dec 12, 2012 8:47 PM in response to Henry R

Appreciate finding this solution after about 90 minutes of frustration trying to do what in the past has been enormously simple -- uploading an audiobook to my ipod. this seems to work. The new version of iTunes seems quite convoluted for thos of us who like use our iPods for simple tasks, such as listening to a couple of audiobooks and a few tunes. thanks

Nov 23, 2013 1:36 PM in response to Henry R

I don't think the late/great Steve Jobs had this "new and improved" version of ITunes to be so darn frustrating. It used to be relatively simple to put songs into a playlist or to import purchased songs from ITunes into an Apple device such as the IPOD Nano. "Simple" used to be the selling point of Apple products. What happened? With this new version, I feel like I've got to contact Apple Support to do simple tasks. It seems like I'm not the only person having this problem.

transferring songs from ITunes to IPod Nano

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