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Mar 8, 2016 3:36 PM in response to charlotte116by Kenichi Watanabe,Are you using the original USB docking cable that came with it? It is long with a cradle for holding the shuffle. A docking cable for the current 4th gen (and 3rd gen) shuffle does not work with 2nd gen shuffle, because the connector is different. There are third-party replacement docking cables, but they need to be described as being for the 2nd gen shuffle (and some of those are of low quality).
If you can get the shuffle's settings screen to appear in iTunes (when you click its device button on horizontal bar), find the setting for Enable disk use. Checkmark that box and click Apply. Does that makes any difference?
NOTE: With disk use enabled, you need to Eject the iPod in iTunes before physically disconnecting it.