Easy, I had this problem too. The reason it isn't playing is because its not in all the way. I was getting very frustrated with this, so I kept trying to push it onto the dock to get it all the way down.
Solution:
1. Play a song on your ipod/iphone so you can hear it through the device.
2. Connect your ipod/iphone to the docking station(Bose) so that you hear the chime(This lets you know its charging).
3. Pick up the docking station and firmly press the ipod/iphone down on the connector.
4. Keep pressing it and wiggling around until you hear the music begin to play through the docking station.
It may take a few tries, but you will get it.
Hope this helped!
~ Jake
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