Add your butter and sugar to a large mixing bowl. Use an electric hand mixer to whisk the ingredients together for 3 minutes, or until smooth and creamy.

Add in the egg and vanilla extract. Mix again for a few minutes, or until the mixture is smooth and the eggs are fully incorporated with the creamed butter.

Whisk in the flour, cocoa powder, and baking powder. I recommend reducing the speed of your mixer to prevent any flour or cocoa powder from splattering. Make sure there are no pockets of dry or wet ingredients in your cookie dough. Cover your cookie dough with plastic wrap and let it chill in the fridge for 20 minutes. Preheat the oven to 350.

While the cookie dough is chilling, whisk together your milk and pudding mix until homogeneous. Once combined, whisk in the heavy cream. Cover you pudding with plastic wrap and set it in the freezer.

Scoop out 1 ½ tablespoon sized balls of cookie dough and roll them in your hands. Place the cookie dough balls on a baking sheet, leaving at least 1 1/2 inches between each cookie. Bake for 12 minutes. As soon as the cookies come out of the oven, use a small dish to create an indent in the center of each cookie to hold the filling.

Let your cookies cool completely to room temperature before filling them with a few spoonfuls of the pudding mixture.

Beat the cream and vanilla together for about 3-5 minutes, or until stiff peaks begin to form. Add a dollop of fresh cream to the top of each cookie.

Serve and enjoy!