Ingredients

Cupcakes
• 3 sticks unsalted butter, at room temperature
• 1-1/2 cups light brown sugar, packed
• 4 large eggs
• 2-2/3 cups all-purpose flour
• 1 teaspoon baking powder
• 1 teaspoon baking soda
• 1/8 teaspoon finely ground sea salt
• 1 cup milk
• 1-1/2 teaspoon vanilla extract
• 1/2 teaspoon almond extract
• 1 cup semisweet chocolate chips
Filling
• 4 tablespoons unsalted butter, at room temperature
• 6 tablespoons light brown sugar, packed
• 1 cup plus 2 tablespoons all-purpose flour
• 1/2 cup plus 1 tablespoon sweetened condensed milk (half of a 14 oz can)
• 1/4 teaspoon almond extract
• 1/4 cup mini semisweet chocolate chips
Frosting
• 3 sticks unsalted butter, at room temperature
• 3/4 cup light brown sugar, packed
• 3-1/2 cups powdered sugar
• 1 cup all-purpose flour
• 1/2 teaspoon finely ground sea salt
• 3 tablespoons milk
• 1-1/2 teaspoons vanilla extract
• 1 teaspoon almond extract
• Tiny chocolate chip cookies
• Mini chocolate chips (store-bought or homemade)

Instructions

Cupcakes
1. Preheat the oven to 350° F.
2. Line two cupcake pans with paper liners, 24 total.
3. Using an electric mixer combine the butter and brown sugar beating on medium-high speed until light and fluffy, about 3 minutes.
4. Add the eggs one at a time, beating well after each. Scrape the sides of the bowl as needed.
5. In a medium bowl combine the flour, baking powder, baking soda, and salt.
6. Add 1 cup of the flour mixture to the mixer bowl on low speed, then 1/3 of the milk. Continue alternating the flour mixture and milk, ending with the flour. Mix after each addition just until incorporated.
7. Blend in the vanilla and almond extracts.
8. Using a spatula, fold in the chocolate chips.
9. Using an ice cream scoop, divide the batter evenly between the prepared cupcake liners.
10. Bake for 18-20 minutes, until a toothpick inserted in the center comes out clean.
11. Cool in the pans for 5-10 minutes, before transfering to a wire rack to cool completely.
Filling
12. Combine the butter and sugar in a mixing bowl. Cream on medium-high speed until light and fluffy, about 2 minutes.
13. Add in the flour, sweetened condensed milk and almond extract, mixing until smooth.
14. Stir in the chocolate chips.
15. Cover with plastic wrap and chill in the fridge, for at least an hour. You can also prepare this ahead of time and store in the fridge for several days.
16. Once chilled, roll the dough into 24 balls, approximately one-inch.
17. After the cupcakes have cooled, cut a cone-shaped portion out of the center of each cupcake using a small pairing knife. Fill each cupcake with a cookie dough ball. You may need to form a cone shape with the cookie dough to get it to fit properly.
Frosting
18. Using an electric mixer, beat together the butter and brown sugar until creamy.
19. Mix in the powdered sugar until smooth.
20. Beat in the flour and salt.
21. Add the milk, vanilla and almond extracts until smooth and well blended.
22. Frost the filled cupcakes, sprinkling with mini chocolate chips. Top with half of mini chocolate chip cookie.
23. The frosting can also be made in advance and stored in the fridge. Before using, bring the frosting to room temperature. Using an electric mixer, beat the frosting on medium speed, adding a tablespoon or two of milk to soften it up.