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+ servings

Banana Pudding Surprise Cupcakes

Felesha Bell
5 from 1 vote
Prep Time 25 mins
Cook Time 17 mins
Total Time 42 mins
Cuisine A portable banana pudding delight cradled inside a moist and fluffy cupcake!
Servings 24


  • Cupcakes
  • 2 sticks unsalted butter room temperature
  • 1 and 1/2 cups white granulated sugar
  • 2 eggs room temperature
  • 1 T. vanilla extract
  • 2 c. cake flour
  • 1 T. baking powder
  • 1 tsp. kosher salt
  • 1 c. buttermilk room temperature
  • Filling
  • 8 oz. cream cheese softened
  • 1 can sweetened condensed milk
  • 3.4 oz. box instant banana cream pudding
  • 1 c. whole milk
  • 1 c. whipped cream
  • 1/2 c. walnuts toasted
  • 2 bananas diced
  • 2 bags Pepperidge Farm Chessman cookies
  • Frosting
  • 12 oz. whipped cream
  • Walnuts toasted, garnish
  • Chessman Cookies garnish


  • Preheat oven to 325 degrees. Line two 12 cup muffin pans with cupcake liners.
  • Cut 12 cookies in half and pace in the bottom of each cupcake liner.
  • Cream butter in an electric stand mixer fitted with a paddle attachment for about a minute.
  • Pour in sugar and beat for about 4 more minutes or until fluffy.
  • While beating the butter and sugar, sift flour, baking powder and salt into a small bowl. Set aside.
  • Add eggs and vanilla to the batter and beat just until the yellow disappears.
  • Now add in the flour mixture and buttermilk; alternating by starting and ending with the flour mixture. Don't blend too long or else you'll end with some very tough cupcakes.
  • Scoop batter over cookies in cupcake liners filling 3/4 of the way full.
  • Bake for 15-17 minutes or until a toothpick comes out clean.
  • Allow to cool in the pan for about 5 minutes and then remove to completely cool n a wire rack.
  • While your cupcakes are cooling, in a small bowl, combine the milk and pudding mix and blend well using a handheld electric mixer.
  • In another medium bowl, combine the cream cheese and sweetened condensed milk and blend until smooth. Stir the whipped topping into the cream cheese mixture gently Add the pudding mixture to the cream cheese mixture and stir until completely combined.
  • Fold in walnuts and bananas.
  • Assembly - Remove a circular chunk from the center of each cupcake.
  • Fill with 1.5 T. of the filling.
  • Break remaining cookies in half and place over filling.
  • Pipe and decorate the cupcakes with whipped cream and garnish with walnuts and crushed cookies. Say Grace and enjoy!
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