For the Cupcake Toppings:
To Make Cupcake Batter:
To make the cupcakes, preheat the oven to 350° F. Line two cupcake pans with paper liners.
Using a KitchenAid Stand Mix fitted with the paddle attachment, combine the butter and brown sugar. Cream together on medium-high speed until light and fluffy, about 3 minutes. Mix in the eggs one at a time, beating well after each egg is added. Scrape down the sides of the bowl as needed.
Combine the flour, baking powder, baking soda, and salt in a medium bowl. Stir together to blend. Add the dry ingredients to the bowl on low speed and alternate with the milk until incorporated. Blend in the vanilla. Fold in the chocolate chips by hand with a spatula.
Divide the batter evenly between the prepared cupcake liners. Bake for 18-20 minutes, until a toothpick inserted in the center comes out clean. Allow to cool in the pan 5-10 minutes, then transfer to a wire rack to cool completely.
Cookie Dough Filling:
To make the cookie dough filling, combine the butter and sugar in a KitchenAid Stand Mix fitted with a paddle attachment. Cream on medium-high speed until light and fluffy, about 2 minutes.
Beat in the flour, sweetened condensed milk and vanilla until incorporated and smooth. Stir in the chocolate chips. Cover with plastic wrap and refrigerate until the mixture has firmed up a bit, about an hour.
To Make Frosting:
To make the frosting, use a KitchenAid Stand Mix fitted with a paddle attachment to beat together the butter and brown sugar until creamy (about 1 minute). Mix in the confectioners’ sugar until smooth. Then gradually beat in the flour and salt.
Mix in the milk and vanilla extract until smooth and well blended.*
- Milk - If you don't have milk on hand I have tested this recipe and used a half cup of half and half and ½ cup of water. It worked just find.
- Frosting - If you make the frosting ahead of time and refrigerate it. The frosting will need to come to room temperature before handling it... it was a bit difficult to deal with cold since it was full butter that had almost hardened!
- Filling Cupcakes - I like to use a melon baller to scoop out the inside.
- Toppings - I save the little balls of cookie cake whole, and reuse them and top each of the cupcakes with the cookie cake ball plus an additional mini cookie if I have them available.
- KitchenAid Stand Mixer - Don't worry if you don't own a KitchenAid Stand Mixer. You can use a hand mixer or even mix everything by hand.
- Make Ahead - You can make the cupcakes and filling up to a day in advance. Then make then stuff and frost the following day.
Serving: 1g | Calories: 380kcal | Carbohydrates: 73g | Protein: 5g | Fat: 8g | Saturated Fat: 4g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 1g | Trans Fat: 1g | Cholesterol: 39mg | Sodium: 177mg | Potassium: 152mg | Fiber: 1g | Sugar: 53g | Vitamin A: 173IU | Vitamin C: 1mg | Calcium: 88mg | Iron: 2mg