Preheat oven to 375° F. Spray 2 baking sheets with nonstick spray, or line with parchment paper. Using an electric mixer, combine sugar and butter in large mixing bowl until fluffy. Add eggs, one at a time. Add milk and extracts. Mix until smooth.

In another bowl, combine flour, baking powder and salt. Stir to mix. Add dry ingredients to wet ingredients in 1/2-cup batches, fully incorporating each time. Using a tablespoon, place round spoonfuls of dough on baking sheets 1 inch apart. Bake until edges begin to brown, about 13 to 15 minutes. Let cool completely.

Place powdered sugar in large mixing bowl. Gradually stir in enough boiling water to make a thick, spreadable mixture. Spread frosting on half of each cookie. Place on a rack to drip. Once all cookie halves have been frosted, stir 1 tablespoon cocoa powder into the frosting. If it doesn’t seem dark enough to appear black, stir in additional cocoa. Add 1 to 2 tablespoons of boiling water if mixture appears too thick. 

Ice the remaining half of each cookie with chocolate frosting. Place on rack to let frosting drip and set. Store in an airtight container. If making a day or two in advance, store in the refrigerator. 

Calories: 268, Fat: 6 g (4 g Saturated Fat), Cholesterol: 35 mg, Sodium: 116 mg, Carbohydrates: 52 g, Fiber: 1 g, Protein: 3 g.