Step 1

Preheat the oven to 350°F. Line cupcake pans with 18 paper or silicone liners. Spray each liner with non-stick cooking spray and set aside.

Step 2

To a large mixing bowl, add and whisk to combine: flour, cocoa powder, baking powder, baking soda, and salt. Add in sugar and brown sugar, and whisk again to combine.

Step 3

To a smaller mixing bowl, add and whisk to combine: oil, buttermilk, egg and vanilla extract. Pour the wet ingredients into the bowl of dry ingredients. Using a mixing spoon or spatula, stir well to combine wet and dry ingredients together, but don’t overmix or the cupcakes will be tough and dry.

Step 4

Using a cookie scoop or large spoon, add batter to 18 cupcake liners, filling 3/4 of the way full.

Step 5

Place pans in the preheated oven and bake cupcakes for 18-21 minutes, or until a toothpick inserted into the center of a cupcake comes out dry or with a few moist crumbs.

Step 6

Remove from the oven and transfer the cupcakes to a wire rack to cool completely. Meanwhile, prepare the frosting.

Step 7

Using a stand mixer fitted with the paddle attachment, beat the butter, powdered sugar, vanilla extract and heavy whipping cream together until well combined. The consistency should be smooth and stiff with peaks but spreadable.

Step 8

Using an ice cream scoop, add some vanilla frosting to top of each cupcake. Use a mini offset spatula to smooth out the frosting into a thick mound.

Step 9

To the frosting that you have left, beat in the crushed cookies. Scoop frosting into a piping bag fitted with a large piping tip. I use Wilton tip 2D.

Step 10

Pipe a dollop of Oreo frosting on top of the vanilla frosting. Top each cupcake with a whole Oreo cookie and enjoy!