Instructions

1. Preheat oven to 350° F. Grease a mini muffin pan with cookie spray or Crisco.
2. Combine butter and sugars in your stand mixer and beat on medium speed until light and fluffy.
3. Add eggs and vanilla extract. Beat into butter and sugar until thoroughly mixed.
4. In a medium sized bowl, combine flour, cocoa powder, dry pudding mix, baking soda and salt. Stir to combine. Set aside.
5. Slowly add dry ingredients into batter and beat on a low speed until dough starts to form. If dough is a little dry, add 1 tablespoon of milk. Set dough aside.
6. Use a food processor to grind Oreo cookies into a fine crumb.
7. Melt butter in a microwave-safe bowl until melted. Combine melted butter with Oreo cookie crumbs and stir until there are no dry crumbs left.
8. Spoon 1 tablespoon of Oreo cookie crumbs into the bottom of the mini muffin pan. Press down with a spoon or tart shaper.
9. Drop 1-1.5 tablespoons of dough into the greased mini muffin pan on top of the shortbread crumbs. Bake at 350°F for 12-15 minutes.
10. Remove cookies from oven and allow to cool for at least 5 minutes. Use a tart shaper or the back of a spoon to gently push down the middle of the cookies. Allow to cool for another 30 minutes in the pan. You may need to run a knife around the edge of the cookies to help release them from the pan. Cool completely.
11. Put bowl and whisk in the freezer for 15 minutes until completely cold. Whip heavy cream on medium high speed for several minutes until bubbly.
12. Add powdered sugar and beat on medium high until stiff peaks form. Refrigerate whipped cream.
13. Use a sharp knife to cut a chocolate bar into small shavings. You will need a ½ C for the pudding and some to sprinkle on top of the cookies.
14. Combine instant chocolate pudding mix with milk. Whisk until powder dissolves. Refrigerate until pudding is firm.
15. Take 1 cup of the whipped cream and fold into pudding until mixed along with chocolate shavings. Do not mix vigorously as it will deflate the whipped cream. Refrigerate until you are ready to assemble cookies.
16. To assemble the cookies, put the mousse in a Ziploc bag. Cut the tip off the end of the bag and gently fill the middle of the cookie cup with mousse. Divide between cookie cups.
17. Top mousse with a dollop of the leftover whipped cream and chocolate shavings.
18. Cookies must be refrigerated in an air-tight container after the mousse has been added.