Chocolate Chip Cookie Dough Cupcakes with Cream Cheese Frosting

This weekend we had two cookouts to attend, and I was asked to bring dessert to both.  I wanted to make something that wasn't complicated but would wow all the same.  I've made these cupcakes a few times before and they are always a visually stunning hit (despite the lack of evidence from my poor photos below).  I should point out there are several components to these, but overall they are fairly easy to make.  The assembly process is the most difficult part and that's merely because it's a bit time consuming.  With a toddler and newborn, anything time consuming is something I just don't have time to tackle, so the fact that I plan to make these again in a few days should speak volumes.  After the girls went down for the night, I was able to get my much needed baking therapy and enjoyed every minute of it.  Hopefully, these will bring you some fun time in the kitchen as well!

My biggest pointers for these are to 1.) make the cupcakes and cookie dough filling the day before you need them; 2.) use a pastry bag to fill the cupcakes as it will be much quicker and less messy, and 3.) use a large, round pastry tip to frost them (and any other cupcakes you ever make).  The original recipe calls for a brown sugar icing (see link at bottom of recipe), but I thought that was just a bit too sweet.  I used cream cheese frosting because I felt like it cut the sweetness a bit.  And, because cream cheese frosting is always a hit.  Also, if you are feeling particularly ambitious, you can use the cupcake middles and any left over frosting and chocolate chips to create cake pops.  I really wanted to do this but that whole lack of time thing just kept getting in the way!

Chocolate Chip Cookie Dough Cupcakes with Cream Cheese Frosting:

Ingredients for the cupcakes:
3 sticks unsalted butter, at room temperature
1½ cups light brown sugar, packed
4 large eggs
2 2/3 cups all-purpose flour
1 tsp. baking powder
1 tsp. baking soda
¼ tsp. salt
1 cup milk
2 tsp. vanilla extract
1 cup chocolate chips (semisweet or bittersweet)

For the filling:
4 tbsp. unsalted butter, at room temperature
6 tbsp. light brown sugar, packed
1 cup plus 2 tbsp. all-purpose flour
7 oz. sweetened condensed milk
½ tsp. vanilla extract
¼ cup mini semisweet chocolate chips

For the frosting:
16 ozs. cream cheese
2 sticks butter
2 lbs. powdered sugar
2 tsp. vanilla extract

Garnish:

• Tiny versions of your favorite chocolate chip cookie recipe (you may want to cook these a little longer than normal since the frosting will soften them up quite a bit)

• Mini chocolate chips

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. Fold in the chocolate chips with a spatula.

Divide the batter evenly between the cupcake liners.   Bake for 18-20 minutes, until a toothpick inserted in the center comes out clean.  Allow to cool in the pan 5-10 minutes, then transfer to a wire rack to cool completely.

To make the cookie dough filling, combine the butter and sugar in a mixing bowl and cream on medium-high speed until light and fluffy, about 2 minutes.  Beat in the flour, sweetened condensed milk and vanilla until incorporated and smooth.  Stir in the chocolate chips.  Cover with plastic wrap and refrigerate until the mixture has firmed up a bit, about an hour, if you plan to use immediately.  The dough can also be refrigerated overnight if you plan to assemble the next day.  If the dough becomes too stiff, microwave in 10 second intervals, making sure not to overheat or the mini chocolate chips will melt.

To fill the cupcakes, cut a cone-shaped portion out of the center of each cupcake.  Fill a disposable pastry bag with the dough and cut off the tip.  Squeeze the bag gently to fill each cupcake.  Do not worry about over-filling as it will be covered in frosting.

To make the frosting, beat together the butter and cream cheese in the bowl of a stand mixer fitted with the paddle attachment until creamy.  With the mixer on low, add in the confectioners’ sugar and mix until smooth.  Beat in the vanilla extract until smooth and well blended.

Frost the filled cupcakes as desired, sprinkling with mini chocolate chips and topping with mini chocolate chip cookies for decoration.

Source: Adapted from Annie's Eats.