For the Cake:

1. Preheat the oven to 350°F.
2. In a large mixing bowl, combine the sugar, vegetable oil, eggs and vanilla extract. Beat on medium speed until the eggs and oil are well incorporated. Next mix in the sour cream and beat until well combined.
3. In a separate bowl, sift together the dry ingredients. Alternate adding half the dry ingredients and half of the coffee at a time until all ingredients are added and well mixed. Use a spatula to scrape down the sides of the bowl and stir the batter from the bottom to the top to ensure it’s well mixed.
4. Pour the batter into a 9×13-inch pan. Sprinkle the crushed Oreos over top of the cake batter. Bake at 350°F for 28-32 minutes. Test the cake for doneness by inserting a toothpick into the center of the cake. If the toothpick comes out clean, your cake is done. Remove from the oven and allow to cool completely.

For the Filling:

1. Take the end of a wooden spoon or another round object and poke holes all over the top of your cake.
2. Prepare the pudding layer by mixing a package of instant chocolate pudding with the cold milk. Before the pudding sets, pour it over the top of the cake and put the cake in the fridge to let the pudding set, about 10-15 minutes.

For the Topping:

1. Place the mixing bowl and whisk attachment in the freezer for 5 to 10 minutes to chill. Pour the heavy whipping cream into the chilled bowl and use an electric mixer to beat the heavy cream at medium-high speed until the cream thickens to soft peaks.
2. Slowly add the powdered sugar and continue beating on high speed until stiff peaks start to form.
3. Crush the Oreos in a large plastic bag with a rolling pin or ice cream scoop. Then add the Oreos to the whipped cream and stir until well combined. Spread over top of the pudding. Refrigerate for a minimum of 2 hours.