Download songs from iPod Nano to iTunes

Hi Doggess,

Thanks for using Apple Support Communities. Based on what you stated, it sounds like you want to move your library from the iOS device to a new computer. I would recommend that you read these articles, they may be helpful in troubleshooting your issue.

Re-download or transfer your iTunes Store purchases from an iPhone, iPad or iPod to a computer - Apple Support

​​This feature works only for content bought from the iTunes Store. Any items that you imported from audio CDs or received from other sources won't copy from your device to the iTunes library.

Manage content manually on your iPhone, iPad, and iPod - Apple Support

Cheers,

Mario

See turingtest2's user tip Recover your iTunes library from your iPod or iOS device - although most of this covers iOS devices, there's a link right at the end to an iLounge article that describes how you can recover media from a non-iOS iPod and restore this to your library. I'm doing this from memory* - and don't have an iPod accessible right now to verify that I have all the steps correct ... in summary, you should be able to:

• make sure that iTunes won't automatically sync your iPod when connected
• connect your iPod and configure it to operate in disc mode
• exit iTunes
• in Windows Explorer, you'll then be able to see a Music folder on your iPod
• copy this folder to your desktop - it will contain folders and files with "meaningless" names - that's how it should be
• eject the iPod in Explorer and disconnect it
• run iTunes, make sure these settings are checked in Edit > Preferences > Advanced:
  
• select File > Add Folder to Library..., then browse to and select the Music folder you just copied to your desktop

Note that while this should recover your media it won't extract any playlists that are present on the iPod, and some artwork may not be included (some of the third-party tools referenced in tt2's user tip may offer more complete recovery functions). Once you've done this iTunes will over-write the content of your iPod if you subsequently try and sync it - iDevices can only be synced with one library a time.

In general, though, this is very much an "emergencies only" procedure - iPods cannot be relied on as data storage devices, and iTunes' design is based on the assumption that you maintain your library on a PC (or Mac) and use this to manage and control what's on any iDevices. You should really go back to your old computer and copy the complete library (database, media, artwork ...) to the new one. Then make sure that you create and maintain a backup.

Based on your description I'd suggest doing this as a one-time fix but going back and solving this issue properly by recovering the iTunes library from your old PC.

* I should be able to test and verify these steps within the next day or so - though others may be able to step in and either confirm or correct them!

You can only add to what's on an iPod by syncing (or manually managing music) with a library that its previously been connected to. You can, with care, replicate one "logical" library across two or more machines so that an iDevice can then be synced with each of them.

In your case - unless you follow the process outlined to restore library content from your iPod - you can either keep what's on the iPod now or copy new media to it, erasing the current content. You can't add anything while retaining the existing content. It's an (unfortunate) consequence of how iTunes is designed and implemented, with no workaround other than the kind of "Band-Aid" solution I outlined previously.

It is a reasonable assumption that Apple was constrained by the agreements reached with media providers, when the iTunes Store was being created, such that it would not be easy to use iPods to share copyrighted material between users. Whether that's true or not, it has always been the case that iTunes has been based on a "one user, one computer, one more iDevices" approach - even though features like Home Sharing and iTunes Match somewhat alter this, it is still the case that the only way to retain your iTunes library when you change computers is to move all the data across from old to new. Match provides a partial solution to this, based on an annual subscription that means that library content is uploaded to the cloud and then - on theory - available from any device signed in using the same Apple ID. However, for the vast majority of users transferring data over a network, via a thumb drive or external hard disc is still the preferred - or only viable - solution.

Doesn't help your situation, though ... let me recheck the procedure for copying data back from an iPod in case you reconsider whether to pursue that method ...

Here's the more detailed description of the "emergency" recovery procedure ...

1. This is the starting point ... this is the content of the playlist previously synced with my 2nd gen iPod nano. This is from my main library ... the remaining examples are from an initially empty test library
   
2. With your iPod not connected to your computer, run iTunes and make sure that this setting in Edit > Preferences > Advanced is checked:
   
3. Now connect your iPod, select it in iTunes, and in the Summary tab make sure that the Enable disk use box (Summary tab) is checked:
   
4. Click Apply, then eject your iPod in iTunes, disconnect it from your computer, and exit iTunes.
5. Reconnect your iPod - you should now see it appearing as a disc drive in Windows Explorer, with a folder structure as follows:
   
   You may need to set Windows Explorer to display hidden files and folders for this to show up correctly.
6. Now copy the Music subfolder that is in the iPod_Control folder from the iPod to your desktop (or any other convenient location). If you look inside this folder it will have subfolders called F00, F01, F02, ... where these contain files named XXXX.* where XXXX is a "random" four-character string and the file extension is typically mp3 or m4a (this will vary based on the types of media file you have).
7. When the copy has completed, and still in Windows Explorer, navigate to the folder you just copied, right-click on it and select Properties. Make sure that the Read only and Hidden checkboxes are both cleared:
   
   Click Apply and in the next dialog make sure that Apply changes to this folder, subfolders and files is selected and click OK.
8. Now open iTunes again, and then:
   • select File > Add Folder to Library... (if you don't see the menu bar, press the Alt key to reveal it, or Ctrl-B to enable it permanently)
   • navigate to and select the Music folder that you just copied from the iPod and click on Select Folder
9. iTunes will now add the "lost" music to your library 🙂. If you have the second of these settings in Edit > Preferences >Advanced checked:
   
   the files will be copied to the "standard" iTunes Media folder (typically C:\Users\username\Music\iTunes\iTunes Media), and if you have the first option checked they will be renamed based on settings of artist, album, song name and disc/track numbers (artist and album determine folder names, the remaining items determine file names)
10. When the import has completed, you should now see your music restored to your library ... as illustrated below, some albums may no longer have their associated artwork:
    
    (these will be the albums that you originally downloaded images for using the Get Album Artwork function), and you'll not have any previous playlists, ratings, play counts, etc.

With this all done, you can now add new media to your library. When you attempt to resync your iPod you will get this message:

but when you click Remove and Sync and subsequently click Erase and Sync when you get this prompt

then even though the original content will now be deleted - it will be re-copied using the library content that you just recovered.

As I wrote in earlier responses:

• this is very much an "emergency" procedure - certainly not recommended for any other circumstances
• there are third-party tools that will accomplish the same result and in some cases will also recover playlists, etc.