There’s really no words to describe these cupcakes. My hubby has declared that these are his all time favorite cupcakes. For me, they rank among the top three – the S’mores Cupcakes and Irish Car Bomb Cupcakes all rivaling for the top three slots. I brought a batch of these to work for a mini bake sale (proceeds going to Susan G Komen and breast cancer research), and some of the guys were walking away with up to 4 cupcakes. Oh yes, they’re that good. Or maybe I should have charged much more. Anyway, make these and you’ll win over the hearts of your significant other, family, friends, coworkers…. and if you’re fundraising, you can probably make a pretty penny off of these. No more commentary needed. Enjoy!
Baking Notes:When I made the recipe, I used a single batch of the cupcake base, a 1/2 batch of the cookie dough filling, and a 1/2 batch of the icing. These changes are reflected below. I note this specifically in case you run out of filling or icing. It is perfectly fine to make another 1/2 batch. I did make a whole batch of the chocolate chip cookies (full batch reflected below), although you’ll only need about 1/3 of a batch for the cupcakes. The rest I packaged and sold at my mini bake sale, at least the ones I managed to hide from the hubby.
Chocolate chip cookie recipe adapted from Baking Illustrated (p 434) via Annie’s Eats
Makes 24 cupcakes and 7+ dozen mini chocolate chip cookies
Ingredients for the Chocolate Chip Cookies:
2 c. plus 2 Tbs. all-purpose flour
1/2 tsp. baking soda
1/2 tsp. salt
12 Tbs. unsalted butter, melted and cooled
1 c. brown sugar, packed
1/2 c. granulated sugar
1 large egg plus 1 egg yolk
2 tsp. vanilla extract
1 1/2 c. semi-sweet mini chocolate chips*
* If making normal sized cookies, use regular chocolate chips
Ingredients for the Cupcakes:
3 sticks unsalted butter, at room temperature
1½ c. light brown sugar, packed
4 large eggs
2 2/3 c. all-purpose flour
1 tsp. baking powder
1 tsp. baking soda
¼ tsp. salt
1 c. milk
2 tsp. vanilla extract
1 c. semisweet chocolate chips
Ingredients for the Cookie Dough Filling:
2 Tbs. unsalted butter, at room temperature
3 Tbs. light brown sugar, packed
1/2 c. plus 1 Tbs. all-purpose flour
3.5 oz. sweetened condensed milk
1/4 tsp. vanilla extract
1/8 c. mini semisweet chocolate chips
Ingredients for the Cookie Dough Icing:
1/2 Tbs. (1 1/2 sticks) unsalted butter, at room temperature
¾ c. light brown sugar, packed
1 1/2 to 2 c. confectioners’ sugar
1/2 c. all-purpose flour
heaping 1/4 tsp. salt
1 1/2 Tbs. milk
1 1/4 tsp. vanilla extract
Mini chocolate chip cookies
Mini chocolate chips
Make the Cookies:
Ensure oven racks are placed in upper and lower thirds of the oven. Preheat oven 325°. Line two cookie sheets with parchment paper and set aside.
In a stand mixer fitted with the paddle attachment, beat butters and sugars on medium speed until thoroughly combined. Add egg, egg yolk, and vanilla. Beat until combined, scraping down the sides of the bowl as needed. Sprinkle in dry ingredients and beat on low until combined. Scrape down sides of the bowl, add chocolate chips, and beat briefly until everything’s mixed in. If chocolate chips aren’t evenly distributed, stir with a wooden spoon.
For this next step, you’ll either use a teaspoon (for mini cookies) or a half cup measuring scoop for large cookies (or a tablespoon or 1/4 cup measuring scoop for something in between). Portion out cookie dough – a teaspoon for mini cookies or a scant 1/2 cup for large) and roll into a ball. Pull apart into two equal halves. Place halves on prepared cookie sheets with jagged surfaces facing up. Yes, I thought this was weird too, but the cookies were tasty and stayed soft, so just do it. 🙂 (Actually, I was curious so I googled it. Beantown Baker used the same recipe and said that this step gives the cookies “the crinkled and craggly bakery cookie look.”)
Bake for 11-14 minutes if making the full-size cookies, rotating pans halfway through cooking. If making the mini cookies, start at 6 minutes and keep checking the cookies until the cookies are lightly golden. Outer edges should start to harden but middle should still be soft. Don’t overbake!
Remove from oven and allow to cool slightly on baking sheets before transferring to a wire rack to cool completely.
Make the Cupcakes:
Preheat an oven to 350° . Line two cupcake pans with liners and set aside.
In a stand mixer fitted with the paddle attachment, beat butter and brown sugar on medium-high speed until light and fluffy, about 3 minutes. Add eggs one at a time, beating well between each.
Scrape down sides of the blow and on low speed, slowly add baking powder, baking soda, and salt. Add half of flour, the milk and vanilla, and the remaining flour. Again, scrape down bowl and beat until all ingredients are just combined.
With a spatula, fold in chocolate chips.
Fill prepared cupcake pans with batter, about 2/3-3/4 full. Bake for 18-20 minutes, until a toothpick inserted into center comes out clean. Let cool in pan for a few minutes before removing to a baking sheet to cool completely.
Make the Cookie Dough Filling:
In a stand mixer fitted with the paddle attachment, beat butter and sugar on medium-high speed until light and fluffy, 2-3 minutes. Add flour, condensed milk, and vanilla until smooth. Stir in chocolate chips.
Refrigerate until firm, at least 1 hour.
Make the Icing:
In a stand mixer fitted with the paddle attachment (yes, your mixer is getting a work out with this recipe!), beat butter and brown sugar on medium-high speed until creamy. Add confectioners’ sugar and beat until smooth. With the mixer still running, add flour and salt. Finally, add milk and vanilla extract. Icing should be smooth yet thick enough to pipe.
Assemble the Cupcakes:
When cupcakes are completely cooled, using a paring knife to core out the center, forming a cone-shaped center. Remove cookie dough filling from fridge. Fill each cupcake with 1/2 tsp. cookie dough (I rolled it into a little ball).
Top with frosting. I piped frosting on with a large Wilton star tip.
Garnish with mini chocolate chips and a mini chocolate chip cookie.
Try to restrain yourself from having more than one cupcake.
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