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To make the cupcakes: preheat oven to 350 F. Line two 12-cup muffin pans with paper liners. Measure the flour into a medium bowl. Remove 1-2 tablespoons of the flour and add them to a second bowl with the chocolate chips, mixing with your fingers to coat the chips with the flour; set aside. Add the baking powder, baking soda and salt to the bowl containing only the flour and whisk to combine. In the bowl of a stand mixer, cream the butter and brown sugar on medium speed until pale and fluffy, about 4-5 minutes. Scrape down the sides of the bowl, then add the eggs one at a time, beating well after each addition. With the mixer on low, alternately add the dry ingredients and the milk to the bowl, beginning and ending with the dry ingredients, beating just until incorporated. Mix in the vanilla. Finally, add the chocolate chips that were combined with the flour, and use a rubber spatula to combine until evenly distributed. Divide the batter evenly between the prepared pans, filling each well about 3/4-full. Bake for 18-20 minutes. To make the filling: Cream the butter and brown sugar in a medium bowl until pale and fluffy, about 3-4 minutes. Add the flour, sweetened condensed milk and vanilla and beat to combine. Switch to a spatula and mix in the mini chocolate chips. Wrap the "dough" in plastic wrap and refrigerate until it firms up, at least an hour. To fill the cupcakes: Use a paring knife to cut a cone-shaped piece from the center of each cupcake. Place a piece of the cookie dough filling in the hole in the center of each cupcake. To make the frosting: In the bowl of a stand mixer, beat the butter and brown sugar until creamy, about 3-4 minutes. Add the confectioners' sugar and beat until smooth. Finally, add the flour and salt and beat briefly to combine, then add the milk and vanilla extract and beat until incorporated. Frost the filled cupcakes and garnish, if desired.
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Achievable elevated desserts — laminated doughs, cakes, custards
Inventive pastry — compost cookies, crack pie, cereal milk soft serve
Flour bakery's sequel — cakes, cookies, breakfast pastries
Ball-bearing American rolling pin — even pressure for pie dough
Coarse sparkling sugar — cookie tops, cake borders, donut garnish