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Sep 10, 2016 4:46 PM in response to CSamyby Stuart423,First thing: does the iPod have enough space on it to allow for the content to be transferred from iTunes onto the iPod?
Second, are you selecting the content that is supposed to copy? (If you click on the image of the iPod on the top left, the left side of the screen will allow you to select what you're sending to the iPod.)
Third, what version of iTunes are you using? The latest is 12.4x - you can download the latest from itunes.com.
And last, what version of the iPod operating system (iOS) are you using? 9.3x is the latest, and version 10 is out there in beta. You can update from the App store.