Preheat the oven to 350ºF. Prepare a 9 x 9 inch pan by spraying with cooking spray.

In a large saucepan, melt the butter and black coffee over a low heat until fully combined.

Remove the coffee and butter mixture from the stove. Add the cocoa powder and dark chocolate chips to the saucepan and stir until fully incorporated.

Add brown sugar, salt, and vanilla and stir.

Add the whole eggs and egg yolks into the batter and whisk until they have fully incorporated into the mixture.

Add flour and baking powder. Whisk together until fully combined.

Pour the batter into the prepared pan and bake for 30 minutes, until a toothpick inserted in the center comes out clean or it reaches 210ºF.

Remove the cake from the oven and allow to cool for 5-10 minutes before evenly poking holes across the cake.

While the cake is baking get started on the pudding by adding the sugar, cocoa powder, cornstarch, and salt into a small sauce pan. Stir to combine.

Pour one third of the milk into the pan and whisk until fully incorporated and a thick mixture begins to form. Gradually add the remaining milk, whisking continuously until fully combined.

Place over the stove on low to medium heat. Cook, stirring constantly, until it reaches a boil and the mixture begins to thicken, about 10-12 minutes.

Reduce the heat and simmer for 2 minutes to cook out the flour and the pudding will continue thicken.

Remove from the heat and add the butter and vanilla. Whisk until fully combined,

Allow the pudding to cool for 5 minutes, stirring occasionally, before pouring over the holes in the cake.

Place the cake in the fridge to chill while you prepare the whipped cream.

Using the whisk attachment on a stand mixer, whisk heavy cream, vanilla, and powdered sugar together on high speed until stiff peaks being to form, about 3-5 minutes.

Gently spread the whipped cream on top of the cooled pudding layer on the cake. Generously Sprinkle the crushed Oreos over the top of the whipped cream.

Enjoy!