My Apple iPod Nano stops playing shortly after plugging in the correct headset, but works on docking station. I've tried enabling and disabling crossfade in settings. Any suggestions?

My apple ipod Nano stops playing shortly after plugging in the correct headset. I've tried enabling and disabling crossfade in settings. Any suggestions?

Make sure your headphones are plugged ALL the way in, meaning the white part of the headphones is flush with the Nano and you cannot see any silver from the plug still showing.
B-rock

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    Your nano is pausing playback when the screen goes dark (Either when it goes dark on its own or when you click the sleep/wake button). The reason for this is that it is not detecting your headset. You may be able to hear music, but the headset jack is not inserted enough for the nano to detect that it is there (or something is blocking the connection). Here are your three options:
    Insert the headset jack harder. Most folks find that this solves their problem. If you can see ANY of the silver of the plug when it is inserted, it is NOT fully inserted. You should feel and hear a click" when it is fully inserted.
    Clean out the crud in the headset port. If you have tried #1 and it just won't insert all the way, it is likely that you have crud in your headset jack. Shine a light in there. The entire inside of the jack is white, so if it looks dark down at the bottom, there is probably crud down there. You can try blowing it out or using canned air. Just understand that shoving anything else in there to clean it out will be taking your warranty into your own hands! However, I have cleaned mine out using whatever was handy and small enough to fit in there and so far so good. Your results may vary!
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