Toggle the Hold switch to the Hold position and back. Then press both the center (Select) button and the Menu (upper part of wheel) for up to 10 seconds.
Release the Select and Menu buttons when the Apple logo appears, and quickly simultaneously press the Select and Play/Pause (bottom of the wheel) button.
Switch from the electrical plug to a computer connection (if necessary) when the Disk Mode screen appears. The screen should change to the normal "Do Not Disconnect" update screen.
Contact Apple about finding a repair service if the iPod will not go into Disk Mode.
The "sad" iPod icon usually indicated that the iPod is having trouble connecting with a computer. This is, in most cases, not a serious issue and can be resolved with a few easy procedures. In most cases the data on the iPod is intact, even if the sad icon was displayed.
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