These Chocolate Half Moon Cookies are a New York cookie that's soft, fluffy, and my favorite chocolate cookie of all times. The bottom of the cookie becomes the top that's frosted half vanilla frosting and half chocolate frosting.
Preheat oven to 350 degrees F. Line cookie sheets with parchment paper.
In a stand mixing bowl, add 2 1/4 cups granulated sugar and 1 cup butter. Mix with a paddle attachment on medium until light and fluffy. Scrape down the sides.
Add in the sifted 3/4 cup unsweetened cocoa powder and 1/4 teaspoon saltMix on low until combined.
Add in the 2 large eggs and 1 teaspoon vanilla extract. Mix on low until incorporated into the wet mixture. Scrape down the sides.
In a separate bowl, sift the 3 3/4 cups cake flour, 3/4 teaspoon baking powder, and 2 teaspoons baking soda.
Add half of the flour into the wet mixture and beat on low to avoid a flour shower.
Once the flour is combined into the wet mixture, add half of the 1 1/2 cups whole milk. Continue beating on low. Scrape down the sides once the milk is incorporated.
Repeat with the other half of the flour and mixing.
Repeat with the other half of the milk and mixing. Scrape down the sides and bottom of the bowl and stir in any remnants.
Using a large 3 tablespoon ice cream scoop/cookie scoop, scoop the dough and place 2 inches apart on the cookie sheet. I only put 5 on my cookie sheet.
Place in the oven for 15 minutes or until the centers are set. The times will vary depending on the size of the cookies just make sure the center of the cookie is the same color as the edges of the cookie and not darker.
Let the cookies cool on the cookie sheet for 10 minutes before placing the cookies on the cooling rack.
Icing
In the mixing bowl, add in the 1/2 cup butter1/4 cup shortening. Mix until the two are combined. Scrape down the sides.
Add in half of the 3 1/2 cups powdered sugar and mix on low. Scrape down the sides.
Add in the remaining 1 3/4 cups of powdered sugar, 3 tablespoons whole milk, 1/2 tablespoon vanilla extract, and 1/8 teaspoon salt. Mix on low until incorporated.
Fudge Icing
In a double boiler, add in the 2 ounces dark chocolate chips, 2 ounces milk chocolate chips, and 2 tablespoons butter. Stir occasionally until the chocolate is melted.
Add in the 2 1/4 cups powdered sugar, 1 tablespoon light corn syrup, 1 teaspoon vanilla extract, and 1/8 teaspoon salt. Stir until the chocolate looks like it wants to seize up.
At this point, take 4 tablespoons hot water from the bottom of the double boiler and add them into the chocolate mixture. Stir until the chocolate thins out. The fudge icing should make thick ribbons. If it's too thick, add about a tablespoon of additional hot water. If it's too thin add a small amount of powdered sugar.
Keep the fudge icing over the double boiler otherwise, it will harden up and will not be spreadable.
Assemble
After the cookies have cooled, spread the fudge icing on half of the cookie. Do all the fudge sides of the cookies first. By the time you get to the white icing, the fudge will be hard and will make your life a lot easier. I promise.
After the fudge icing has been applied, spread the white icing on the other half of the cookie.
Store in an airtight container.
Notes
Storage: Store in an airtight container at room temperature for up to 5 days.