These cupcakes are seriously insane. So dense and rich. They have such a deep dark chocolate flavor that is sweet but also slightly bitter (in a good way of course) and that bitterness pairs really well with the sugary cookie dough frosting. The two combined is just absolutely a match made in heaven.

These cupcakes are really not hard to make. The only thing I will mention for the frosting is to cream together the sugar and butter really well. If you think it’s combined enough… cream it together a little more. This will insure that all those sugar crystals are broken down so that the frosting isn’t crunchy. You want that pillowy texture that cookie dough has, so just be sure to let your mixer do the work and you’ll be good!

As with anything that requires an oven to cook, the baking time will always differ depending on what type of oven you have. Be sure to cook your cupcakes on the middle rack. This will insure that all the cupcakes get cooked evenly and that the bottoms/ or tops don’t get overcooked from being on the top or bottom rack. Just keep this in mind when cooking! I also used large cupcake sleeves, not the regular sized cupcake cups. My cupcakes took about 25 minutes, but yours might take more or less time depending on your oven and also the size of your cupcake sleeves. If you are using regular sized sleeves, your cook time should be about 18-20 minutes. Just use a toothpick to gage it’s done-ness.


Prep time: 20 minutes

Cook time: 25 minutes

Total time: 45 minutes

Serves: 15 large cupcakes


For cupcakes:

  • 1.5 cups all purpose flour
  • 1.5 cups granulated sugar
  • 1 cup dark chocolate cocoa powder
  • 1 tsp baking soda
  • 1 tsp baking powder
  • 1/2 tsp kosher salt
  • 2 large eggs, room temperature
  • 1/3 cup vegetable oil
  • 3/4 cup espresso (or coffee)
  • 2 tsp vanilla extract
  • 1/2 cup buttermilk
  • 1/4 cup sour cream
  • 1 tbsp Hershey’s chocolate syrup

For frosting:

  • 1 cup all purpose flour
  • 1/2 cup dark brown sugar
  • 2 cups (16oz box) powdered sugar
  • 1/4 tsp salt
  • 1 tsp vanilla extract
  • 2 sticks softened butter, unsalted
  • 2 tbsp half and half
  • 1 cup mini semi sweet chocolate chips


For cupcakes:

  1. Preheat the oven to 350 degrees F. Place 18 cupcake sleeves in your cupcake pans. Set aside.
  2. Use a stand mixer with the whisk attachment. Place flour, sugar, cocoa powder, baking soda, baking powder and salt into the mixer on low speed till incorporated.
  3. Add in eggs, vegetable oil, coffee, vanilla extract, buttermilk, sour cream and chocolate syrup. Place the mixer on medium speed for a 3-4 minutes until incorporated. Be sure to scrape down the sides of the bowl while mixing.
  4. Use an ice cream scooper to fill your cupcake sleeves 2/3 full. Repeat till all the sleeves are full.
  5. Place in the middle rack of the oven (cook in batches if needed) and bake for about 18-20 minutes for regular sized cupcakes and 23-25 for large cupcakes. Use a toothpick to check to see if they are done. Remove from the oven and allow to cool completely before frosting.

For frosting:

  1. Place your flour in a bowl and microwave for 60 seconds… stirring every 20 seconds. (This is going to kill any of the bacteria in the flour so that it’s safe to consume.)
  2. Place sugars, salt and butter in a stand mixer with the paddle attachment. Beat on high speed for a few minutes until the butter and sugar are creamed together very well and there are no chunky or crunchy pieces. Scrape the sides of the bowl while mixing.
  3. Add in powdered sugar and combine on low speed. Then add in the flour and mix till combined. Lastly, add in the half and half and chocolate chips and continue to mix on medium speed till fully combined.
  4. Frost cupcakes and enjoy!

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