Chocolate Chip Cookie Cupcakes with Chocolate Frosting

I originally decided to make these cupcakes for the bakesale because they do not need frosting and since they needed to be packaged individually I figured it would save me quite a bit of time not worrying about smudging frosting, but per usual, my sweet tooth got the better of me. I could not resist making these into my own version of Mrs Field's cookie cupcakes. I you have ever had one, then you know why I had to proceed with that direction. If you have not had one, please immediately make these or go out to the nearest Mrs. Field's at once and buy one. Because this is not simply taking cookie dough and baking it in a cupcake tin they are not quite as dense as my original inspiration, but that makes them a perfect pair with the frosting. They are sort of a cakey cookie, and I am sorry, but it would just be in poor taste to serve cake without frosting. In order to keep them a little more tidy for packaging purposes, after they came out of the oven I used the rounded side of a melon baller to smush in a 1/2" well to fill with frosting. After filling the indentation with frosting I continued to swirl it up just a smidge to make them super cute. Since these are for a bake sale I also found the cutest ribbon to finish off the packages that says 'Thank You' to our oh so generous customers. I am still a few weeks away from being able to eat anything like this, but my taste testers were thoroughly impressed, so this definitely goes on the 'make again' list. I just don't know if I will ever get to that list with so many new things I want to try!

Recipe Adapted from Martha Stewart
Cupcake Ingredients (makes 24 cupcakes):
-1 1/2 Cups all purpose flour
-3/4 teaspoon baking powder
-1/2 teaspoon salt
-1 Cup unsalted butter, room temperature
-3/4 Cup sugar
-3/4 Cup light brown sugar
-3 eggs
-1 teaspoon pure vanilla extract
-1/2 Cup milk (I used unflavored light soy milk, but non-fat cow's milk would work as well)
-8 oz semi-sweet chocolate chunks

1. Preheat oven to 375°. Line a standard size muffin tin with cupcake liners.
2. Combine flour, baking powder, & salt. Set aside.
3. At medium-high speed cream together butter and both sugars until pale and fluffy- about 3 minutes. Reduce speed to medium and add eggs one at a time until combined. Add in vanilla.
4.  Reduce speed to low and alternate adding flour mixture and milk in at least two batches. Stir in chocolate chunks by hand.
5. This is where I halt the process and refrigerate the dough for at least 24 hours, but you could also bake them immediately.
6. Fill each cup with 1/4 Cup batter. Bake for 20 minutes or until golden brown. Transfer the tins to wire racks and allow the cupcakes to cool completely in the tins.
7. After the cupcakes have been out of the oven 10 minutes, use your melon baller to push into the tops of the cupcakes to create a 1/2" 'frosting well'.
8. After cupcakes are cooled completely, use a pastry bag to fill/frost the cupcakes.

Dark Chocolate Frostng Ingredients:
- 16 oz semisweet chocolate, finely chopped
-6 Tablespoons Cocoa powder
-6 Tablespoons boiling water
-3 Sticks unsalted butter, just at room temperature (I have had a lot of trouble with my frostings if the butter is too warm)
-1/2 cup confectioner's sugar
-1/4 teaspoon salt

1. Melt semisweet chocolate in a double boiler, or glass bowl over a simmering pot of water. Be sure not to let the water boil or touch the bottom of the bowl. Continuously stir over the heat until chocolate is just about smooth. Then remove from heat and stir until smooth. Set this off to the side, stirring occassionaly until completely cooled, about 30 minutes.
2. Stir together the Cocoa powder with boiling water until smooth, set aside.
3. In a mixer on medium-high speed combine butter, sugar, and salt until pale and fluffy, about 3 minutes.
4. On low speed mix in melted chocolate until combined. Beat in cocoa mixture. Scrape down the sides as needed until fully incorporated.

Bookmark and Share


  1. I happen to be eating one of these right now. Just got home after our WILDLY successful bake sale and am treating myself to this bit of awesome before taking a nap. It was so nice to meet you- hopefully I'll be seeing you at the taco walk-up or farmer's market soon!

  2. These were every bit as delicious as they look! I loved the packaging, too. Thanks so much for baking and for coming, it was great to meet you in person!

  3. These were so adorable. I loved the packaging and wish I had tried one as they looked delicious. I echo the other two ladies in that it was lovely to meet you.

  4. What an awesome event! I'm proud of you and your baking adventures.