For the cookie dough:2 sticks softened butter
3/4 cup sugar
3/4 cup brown sugar
4 tbsp milk
1 tbsp vanilla
2 1/2 cups all purpose flour
1/4 tsp. salt
1 cup mini chocolate chips
For the cupcakes:3 sticks softened butter
1 1/2 cups light brown sugar, packed
4 large eggs
2 2/3 cups all purpose flour
1 tsp. baking powder
1 tsp. baking soda
1/4 tsp. salt
1 cup milk
2 tsp. vanilla extract
For the frosting:3 sticks softened butter
3/4 cup light brown sugar, packed
3 1/2 cups powdered sugar
1/2 tsp. salt
2 tbsp. milk
1 tsp. vanilla extract
To make the cookie dough, combine the butter and sugars in a mixing bowl and cream on medium-high speed until light and fluffy, about 2 mins. Beat in milk and vanilla until incorporated and smooth. Beat in the flour and salt until just combined. Stir in the chocolate chips. Using a 1.5 tbsp scoop, shape the dough into balls or tubes. Freeze on a parchment lined baking sheet overnight.
To make the cupcakes, preheat the oven to 350° F. Line two cupcake pans with paper liners (24 total). In the bowl of a stand mixer fitted with the paddle attachment, combine the butter and brown sugar. Beat together on medium-high speed until light and fluffy, about 3 minutes. Mix in the eggs one at a time, beating well after each addition and scraping 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 mixer bowl on low speed, alternating with the milk, beginning and ending with the dry ingredients, mixing each addition just until incorporated. Blend in the vanilla.
Using a 3 tbsp scoop, fill the prepared cupcake liners 2/3 full with the cupcake batter. Place a frozen cookie dough ball on the top center of each cupcake.
Bake at 350 for 16-18 mins.
To make the frosting, combine the butter and brown sugar in a mixing bowl and cream on medium-high speed until light and fluffy. Beat in the powdered sugar until smooth. Beat in the salt, milk, and vanilla extract until smooth and combined.