How to Extract Music From an Old iPod
Although Apple doesn't allow you to transfer music from your iPod to your computer, there are many programs that provide this feature. These music recovery programs can be found on software download sites and usually require you to purchase a license to gain access to all of the software features. Depending on the features and the company, the software costs between $14 to $30. Music extraction should only be used to recover your own music.
Instructions
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Go to CNet.com. Click the "Downloads" tab underneath the search bar in the browser window, followed by typing "Music transfer" in the search bar. Click the magnifying glass icon or press the "Return" key on your computer.
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2
Click the "Music Liberator" link, followed by clicking the "Download Now" button. Drag the "Music Liberator" icon to your "Applications" folder to install the program. Click "Go" at the top of your screen and click "Applications," followed by double-clicking "Music Liberator" to run the application.
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3
Open iTunes by clicking the "iTunes" icon on your dock. Hold down the "Command" and "Option" keys. Connect your iPod to your computer, and wait 15 seconds after your iPod appears under your iTunes' Devices section to release the keys. This bypasses the iTunes auto update, which can erase your iPod content.
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Click the name of your device on the sidebar of iTunes. Check the box next to "Manually manage music" and click Apply.
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Click the songs you wish to copy. Hold shift to select multiple songs at once, followed by clicking the "Copy" button.
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Tips & Warnings
Music Liberator will allow only 5 songs copied from the iPod to the computer at a time until you purchase a registration license.