Chocolate Chip Cookie Cupcakes

The other day, my husband suggested making cupcakes topped with cookies in some way. I found this recipe the next day! I love the idea and now hope to try other variations.

My daughter and her sidekick (bestie) were baking together over the summer and spent an afternoon on this deliciousness. Everyone was quite pleased with the results. The cupcakes were very moist and tender and the cookies on top were crispy and delicate. Perfect.

The recipe is from Martha Stewart Living; we modified the proportions and method. Next time, I may reduce the size of the cookie on top and chill the cookie dough prior to baking.

Yield: 18 cupcakes

For the Chocolate Chip Cookie Base & Cookie Topping:

  • 1 cup plus 2 T all-purpose flour
  • 1/2 tsp baking soda
  • 1/2 tsp plus 1/8 tsp coarse salt
  • 1 stick unsalted butter, at room temperature
  • 3/4 cup light-brown sugar, packed
  • 6 T granulated sugar
  • 1 large egg
  • 1 tsp pure vanilla extract
  • 1 cup (6 oz) semisweet chocolate chips

To Make the Chocolate Chip Cookie Base:

  1. Whisk flour, baking soda, and salt into a bowl.
  2. Beat butter and sugars with a mixer on medium-high speed until pale and fluffy, about 3 minutes.
  3. On low-speed, beat in the egg.
  4. Add flour mixture in 3 additions.
  5. Beat in vanilla.
  6. Mix in chocolate chips.
  7. Chill dough while preparing the cupcake batter.

For the Cupcakes:

  • 3/4 cup all-purpose flour
  • 3/4 cup cake flour
  • 1/2 T baking powder
  • 1/4 tsp coarse salt
  • 1 stick unsalted butter, at room temperature
  • 3/4 cup plus 2 T granulated sugar
  • 2 large eggs
  • 1 tsp pure vanilla extract
  • 1/2 cup plus 2 T whole milk
  • Chocolate Chip Cookie Base (see above), including 18 (1.5-inch) cookies
  • Simple Vanilla Frosting (see below)

To Make the Cupcake Batter:

  1. Preheat oven to 350 degrees, preferably on convection. Line 18 muffin tin wells with baking cups.
  2. Whisk together flours, baking powder, and salt.
  3. Beat butter and sugar with a mixer on medium-high speed until pale and fluffy, about 3 minutes. Reduce speed to low.
  4. Add eggs, 1 at a time, then vanilla.
  5. Beat in flour mixture in 3 additions, alternating with milk, beginning and ending with flour.

To Layer & Bake the Cupcakes:

  1. Press 1 tablespoon cookie dough into bottom of each baking cup. (At this point, I used a small cookie scoop (1/2 T) to ration the remaining cookie dough and put it back in the refrigerator.)
  2. Top each with 1.5 to 2 tablespoons batter. (I used a cookie scoop.)
  3. Bake until a toothpick inserted into the centers comes out clean, 18 to 20 minutes. (Keep oven on to bake the cookies for the topping.)
  4. Transfer tins to wire racks; let stand for 5 minutes. Transfer cupcakes to racks. Let cool completely.
  5. While the cupcakes cool, prepare the frosting and bake the cookies for the topping.

For the Simple Vanilla Frosting:

  • 2 sticks plus 2 T unsalted butter, at room temperature
  • 3 cups plus 6 T confectioners’ sugar, divided
  • pinch coarse salt
  • 1/2 tsp vanilla extract
  • 1/2 T whole milk

To Make The Frosting:

  1. Beat butter and 3/4 cups confectioners’ sugar with a mixer on medium speed until pale and fluffy, 2 to 3 minutes.
  2. Reduce speed to medium-low; gradually add the additional 2 1/2 cups plus 2 T confectioners’ sugar.
  3. Add milk and vanilla; mix to incorporate.
  4. Raise speed to medium-high and continue to beat until pale and fluffy, about 3 minutes.

To Finish & Decorate:

  1. Place the chilled scoops of cookie dough on 2 parchment paper-lined rimmed baking sheets.
  2. Bake in the pre-heated oven until edges are dark gold but centers are pale gold and look a bit underdone (for chewy) or until centers are set (for crisp). (We baked ours for about 7 minutes.)
  3. Transfer baking sheets to wire racks to cool for 5 minutes; then transfer cookies to a wire rack to cool completely.
  4. Transfer frosting to a pastry bag fitted with a star tip, or as desired.
  5. Pipe frosting onto cupcakes, and top each with a cookie.

About Josette@thebrookcook

I live in Stony Brook, New York on Long Island. I love garlic and baking. My hobby (and love) is to try new recipes. My favorite recipe resources include The New York Times, Food and Wine, Bon Appetit, and Martha Stewart Living. Enjoy!

6 responses to “Chocolate Chip Cookie Cupcakes

  1. Mom

    You always come up with interesting
    recipes.

  2. jessicanadelson

    Leave it to Mr. Brook Cook to come up with a way to finagle TWO desserts in one sitting! 😋

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