Yeah, it's happened to me a few times. One time it's even broken the glass I was using. However, I don't have the slightest idea as to what conditions I'd have to recreate, because the environment outside the cup is surely as much a factor for the possibility of an, "ice pop," as the environment inside the cup. Also, the size of the cup, and the positioning of the ice inside the cup, and whether or not the ice has stuck together such a way to allow an ice pop, are all factors.
I wouldn't know how to get the ice to pop again.