These instructions explain how to copy files from your iPod to your Mac using the tools built into Mac OS X. There is plenty of 3rd-party software that can transfer files from iPods, for example EphPod for Windows and iLinkPod for Mac, but the method I will show you does not require 3rd party software. The procedure is basically this: use the command line to copy the randomly-named files from the iPod to a temporary folder on your Mac’s hard drive, then add them to iTunes to automatically re-organize and rename the files appropriately.
The copy process will require double the amount of disk space that is used on your iPod. So if you have 6GB worth of music on your iPod, copying the music off of your iPod will require 12GB worth of space on your computer — 6GB of storage for the files copied from the iPod, plus 6GB of temporary storage (which you can delete after).

A new folder will appear on your desktop, and you can type in a new name for it. Name the new folder “ipod”.
Click on the icon of your iPod. This should show you the summary screen:

Scroll down to the Options section, and make sure that the option to “Enable Disk Use” is enabled:

Click the “Apply” button if the option was previously not enabled.

Click the “Apply” button after making changes. Note that, from now on, when you add new music to iTunes, a copy of those files will be made in your Music folder. So remember to delete original files after importing to iTunes.
cp -R "/Volumes/My iPod/iPod_Control/Music/*" ~/Desktop/ipod/ ;
Open a Terminal window from your Applications -> Utilities folder, and press ⌘-v (or Edit -> Paste) to paste the text into it. Use the back-arrow key (←) to move the cursor to where it says “My iPod”, and use your delete key to replace “My iPod” with the name of your iPod, which you noted in step 2. So for example, if your iPod is named FooPod, the line in your Terminal window should look like:

When the command line looks like the above, except with your iPod’s name in place of FooPod, press the Enter key.
The temporary “ipod” folder on your desktop will begin to fill up with the files from your iPod. The files will have random names, like “ZTUG.mp3″ — don’t worry, that will be fixed in the next step! The copy process could take a long time, depending how much music you have on your iPod. This will in no way effect the contents of your iPod. It merely copies the files, it doesn’t change them.

When iTunes is finished importing the files, you can delete the temporary folder (“ipod”). You’re done!
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