Preheat oven to 350°F and line a 9" spring-form pan with parchment paper.
Make the crust: Place the Oreos and instant espresso powder into a food processor and pulse until a fine consistency. Pour in the melted butter and pulse until fully combined. Press the mixture into the bottom of the spring-form pan making sure it is compact and bake for 10 minutes. Remove and set aside to cool while you make the filling.
Prepare the water bath: Turn the oven down to 320°F. Place a large roasting pan in the oven on the middle rack. Pour hot water into the pan, making sure it is about 1" in depth. Close the oven door.
Make the filling: Using a stand or electric mixer, beat the cream cheese, butter and sugar on low speed until smooth. Scrape down the sides a few times. Add eggs one at a time making sure they are fully incorporated after each addition. Add the vanilla extract, 6 tablespoons of prepared espresso and flour, scraping down the sides of the bowl as needed to make sure everything is well combined. Pour half of the cheesecake filling into the spring-form pan.
Layer the filling: Dip the lady fingers in the remaining espresso and arrange them in a single layer over the filling. Carefully pour the remaining cheesecake filling over the lady fingers and smooth the top with an off-set spatula.
Bake: Insert the spring-form pan into a 10" cake pan and place the cake pan into the water bath. (Water level should cover half the depth of the cake pan. Add water if needed.) Bake for 1 hour.
Cool: Turn the oven off and let the cheesecake cool in the oven for 1 hour with oven door cracked. Remove the cheesecake from the oven, run a knife around the edge of pan and let the it cool completely on a heat-safe counter top.
Chill: Place the cheesecake, uncovered in the refrigerator overnight or a minimum of 6 hours to set. (Do not remove the spring-form pan.)
Make the whipped topping: Beat the heavy whipping cream until it forms stiff peaks. In a separate bowl, beat the cream cheese, milk and instant pudding until completely smooth. Fold the whipped cream into the cream cheese mixture until it is fully incorporated.
Assemble: Remove the spring-form pan and place the cheesecake on a serving platter. Place the whipped topping mixture into a piping bag with a large tip, I used Wilton 2A, and then decorate the top of the cheesecake by piping large dots. Dust the top of the decorated cheesecake with cocoa powder and keep chilled until ready to serve.