• Preheat the oven to 350 degrees. Line a baking sheet with parchment and set aside.
• Using a food processor, grind the Oreos until crushed.
• In a medium bowl, combine the crushed Oreo pieces, flour, corn starch, cocoa powder, baking soda, baking powder and salt. Whisk to combine well. Set aside.
• In the bowl of a stand mixer, combine the softed butter, sugar and brown sugar. Cream until lighter in color.
• Add in the egg and vanilla and combine well.
• Mix in the dry ingredients into the stand mixer bowl - combine well. Stop the mixer, scrape down the sides and mix again. The dough should be pulling away from the side of the bowl and can be pressed together to form a ball.
• Divide the dough into 9 equal sized balls and place on the prepared baking sheet. Using a flat bottomed drinking cup, flatten the cookies into a disc shape until they are about ¾-1 inch in thickness.
• Bake in the preheated oven for 10 minutes. Immediately upon removing from the oven, use a ¼ cup measuring cup or similar and press it into the cookie while it’s still soft. This will create the cavity needed to contain the filling. As the cookie cools it will harden, so this must be done immediately following the removal from the oven.
• Allow to cool completely while making the filling.

Filling

• In the bowl of the stand mixer, combine the chocolate pudding mix, milk, heavy cream, powdered sugar and vanilla.
• Mix on medium speed for about two minutes - until the mixture is thoroughly combined and looks thick. Add in the melted chocolate and mix again. Stop the machine, scrape the sides and mix again.
• Transfer the filling mixture to a piping bag - no tip or large round tip is fine. Set aside and wait to fill the cookies until they are baked and completely cooled.

Whipped Topping

• In the bowl of a stand mixer, combine the heavy cream, powdered sugar and vanilla. Whip on med/high speed for 2-3 minutes or until stiff peaks.
• Transfer the whipped cream to a pastry bag fitted with a large star tip. Set aside.

Assembly

• Once cool, the cookies are ready to fill. Using the piping bag for the filling, pipe a large mound in the center of each cookie. Gently tap on the counter to settle any point in the top. Pipe a small dollop of the whipped cream on top and sprinkle with desired decoration - we used chopped chocolate chips, but curls, mini chocolate chips, etc would also look great!