Whip cream till soft peaks form. Set aside about a third of the cream. To the remaining whipped cream, fold in the caramel sauce, and about 1/2 cup of the chopped Rolos. Spread into the chocolate crust.
To the cream that you set aside, beat in 3-4 tablespoons of powdered sugar, and the vanilla. I used 3 Tbsp, but you can add more if you want it sweeter. Carefully spread the whipped cream over the caramel layer.
Chill for 3-4 hours, or freeze for about an hour. Sprinkle more chopped Rolos on top of the pie just before serving.