Step 1

Preheat the oven to 350° F.

Step 2

Using the paddle attachment on an electric mixer, combine the butter and brown sugar. Cream together on medium-high speed until light and fluffy, approx 3 minutes. Add eggs one at a time, beating well after each addition and scraping down the sides of the bowl.

Step 3

Whisk the flour, baking powder, baking soda, and salt together in a medium bowl.

Step 4

Alternating add the dry ingredients to the mixer bowl with the milk on low speed, beginning and ending with the dry ingredients, mixing each addition just until incorporated.

Step 5

Blend in the vanilla.

Step 6

Fold in the chocolate chips with a spatula.

Step 7

Divide the batter evenly between 24 cupcake liners. Bake for 18-20 minutes, until a toothpick inserted in the center comes out clean. Allow to cool in the pan for 5-10 minutes, then transfer to a wire rack to cool completely.

Step 8

Cream butter and sugar in a mixing bowl on medium-high speed until light and fluffy(approx2 minutes).

Step 9

Add flour, sweetened condensed milk and vanilla and beat until smooth.

Step 10

Stir in the chocolate chips.

Step 11

Cover with plastic wrap and refrigerate until the mixture has firmed up a bit, (at least 30 minutes).

Step 12

After cupcakes have cooled, fill the cupcakes by cutting a cone-shaped portion out of the center of each cupcake. Fill each hole with chilled cookie dough mixture.

Step 13

Beat butter and brown sugar with the paddle attachment on high speed until creamy and fluffy.

Step 14

Mix in the powdered sugar until smooth.

Step 15

Beat in the flour and salt.

Step 16

Mix in the milk and vanilla extract until smooth and combined.