To begin, place a cup of the berries in a shallow dish.
Sprinkle with two tablespoons of the powdered sugar.
Mash the sugar & berries together. Set those aside for now.
In a chilled mixing bowl, combine the cream, vanilla, and remaining 2 tablespoons of powdered sugar. Beat them together on high speed just until stiff peaks form.
Add the berry mash to the whipped cream and fold it together until it is swirled in, but not completely mixed.
Scoop the mixture into small dessert dishes.
Break the cookies into 1 1/2 inch pieces and stick a few into each dish.