Step 1

Preheat oven to 365°F. Line a baking sheet with parchment paper, set aside.

Step 2

In bowl of a stand mixer cream the butter, brown sugar, and sugar on medium speed for 2 minutes. Add the eggs and vanilla and mix to combine. Scrape down the sides of the bowl with a rubber spatula.

Step 3

Add the flour, black cocoa powder, Oreo crumbs, baking soda, baking powder, and salt. Mix to combine.

Step 4

Portion the dough into 1/4 cup sized balls. Place 6 balls of dough on the baking sheet. Using the palm of your hand, press down on each cookie dough ball just slightly. Bake  for 11 minutes. Remove from oven; some cookies may have uneven edges. To fix this, use a very large round biscuit cutter or cookie cutter and immediately after removing the cookies from the oven, gently use the cutter in a circular motion around the cookies to tuck in the edges (think hula hoop motion). We don’t want to cut the cookie! We just want to make the cookies uniformly circle before they set.

Step 5

After doing this press the bottom of a ½ cup or 2/3 measuring cup (or any measuring cup that is smaller than the cookie, as we want to create a small “crust” or “lip” for the chocolate mousse to go into) into the center of each cookie. You don’t need to press down too hard, just enough to create a lip, as mentioned above. (I like to spray the bottom of the measuring cup I’m using with nonstick cooking spray. This isn’t necessary but I do like that it prevents the cookie from sticking to the measuring cup. If you have any questions about this part of the recipe, refer to the blog post as I have photos illustrating exactly what the cookies should look like). Bake an additional 1-2 minutes (if needed). Remove from the oven and let cool on pan for 10 minutes then transfer to a wire rack to cool completely.

Step 6

In a large bowl (or the bowl of a stand mixer fitted with whisk attachment) add the dry chocolate instant pudding mix, heavy cream, milk, powdered sugar, Dutch process cocoa powder, and vanilla extract. Using a hand mixer, mix until smooth and thickened, about 1 minute. The mousse can be made in advance and stored in an airtight container in the fridge for several days.

Step 7

Spoon approximately 3 tablespoons or so of chocolate mousse into the well of each cookie. Dollop with whipped cream and chocolate shavings. Place cookies in airtight container and store in the fridge. Enjoy cookies chilled.