Preheat the oven to 350 degrees F (175 degrees C). Line a 12-cup muffin tin with paper liners.
Cream sugar and butter for cupcake together in a medium bowl. Beat in eggs, one at a time, then stir in vanilla extract. Combine flour and baking powder; add to the creamed mixture and mix well. Stir in 1/2 cup milk until batter is smooth. Pour or spoon batter into the prepared pan.
Bake in the preheated oven until a toothpick inserted into the center of each cupcake comes out clean, 20 to 25 minutes. Cool in the tin for 5 minutes. Transfer to a wire rack and let cool completely, about 20 minutes.
While cupcakes cool, combine cold milk and pudding mix for topping in a bowl. Mix until smooth. Let pudding mixture sit for 5 minutes.
Mix 1/2 cup whipped topping into pudding mixture. Pipe the pudding on top of the cooled cupcakes. Place a dollop of remaining whipped topping on top of each cupcake. Garnish with marshmallows and sift cocoa powder over tops.
Follow individual package instructions on preparing pudding mix.
For an extra touch, take any extra pudding and stuff the insides of the cupcakes.
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