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Using a mini cupcake tin, press one dough square into each well, and up the sides. Try not to have any holes. Bake as directed, or until the cookie cups turn slightly golden.
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With a hand mixer, mix together the 12 oz. container of Cool Whip and the softened 8 oz. bar of cream cheese. If there are any cream cheese bumps, keep whipping, it might just need to melt a little more.
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Add 2 cups of powdered sugar and mix well.
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Fill a pastry bag with the filling (I used one with no tip on it.) Once the cookie cups have cooled, fill each cup with the cream filling.
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Top with your favorite topping.