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Step 1
Connect your iPod to your computer. Open up iTunes if it does not start up automatically when the iPod is connected.
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Step 2
Choose the "iPod" icon in the left column of iTunes and select the "Settings" tab.
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Step 3
Remove the check from the "Open iTunes when this iPod is attached" box in the "Options" section near the bottom.
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Step 4
Make sure the "Enable disk use" box is checked and close iTunes. Keep your iPod connected to the computer.
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Step 1
Download and install Winamp 5.52 from the Winamp website (see Resources below). You may download the full, bundle or Pro versions of Winamp. The full and bundle versions are free and come with free MP3 music files. The Pro version can rip CDs to MP3 files and burn CDs much faster than the full or bundle version.
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Step 2
Click on the "View" menu on top of the main window and select the "Media Library." A column will appear in the left side of the player. Sometimes, the media library will automatically open when you start Winamp.
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Step 3
Scroll down to the "Portables" tab and choose the iPod. Your music files on your iPod will be displayed in the main window.
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Step 4
Add music files to your iPod from your "Playlist" window. If the "Playlist" window is not opened, click the "PL" button on the Winamp player. Add as many files as you wish to your playlist.
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Step 5
Right-click the music files you want to transfer to your iPod. You may also use the "Select All" icon at the bottom of the "Playlist" window to add all of the files.
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Step 6
Click the "Send to:" option from the menu, and then select "iPod." The "iPod" option will appear as the specific name you have previously assigned your iPod.
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Step 7
Choose the "Eject" button in the bottom-right corner when you are done managing your iPod.
