Ingredients:

  • 1 (15.25 oz) box Chocolate Cake Mix
  • 3 Large Eggs
  • 1 cup Water
  • 1/2 cup Vegetable Oil
  • 2 (3.4 oz) boxes Instant Vanilla or White Chocolate Pudding Mix
  • 3 cups Cold Whole Milk
  • 1/2 cup Crushed Oreo Cookies (finely ground, reserved from 24 cookies)
  • 2 cups Cold Heavy Whipping Cream
  • 1/2 cup Powdered Sugar
  • 1 teaspoon Vanilla Extract
  • 24 Oreo Cookies (18 coarsely chopped for garnish, 6 finely crushed for pudding soak)

Instructions:

  1. Prep the Oven and Pan: Preheat oven to 350°F (175°C). Grease and flour a 9x13 inch baking pan.
  2. Mix the Batter: Combine the cake mix, eggs, water, and oil in a large bowl. Mix on medium speed for 2 minutes until smooth.
  3. Bake: Pour the batter evenly into the prepared pan. Bake for 30–35 minutes, or until a toothpick inserted into the centre comes out clean.
  4. Cool Slightly: Remove the cake from the oven and let it cool on a wire rack for exactly 5 minutes. The cake must still be warm for optimal soaking.
  5. Prepare the Pudding Soak: While the cake is cooling, whisk together the instant pudding mix and 3 cups of cold whole milk in a medium bowl until the mixture just begins to thicken (about 2 minutes).
  6. Add Crushed Oreos: Fold the 1/2 cup of finely ground Oreo crumbs into the pudding mixture.
  7. Poke the Cake: Using the handle of a wooden spoon, poke deep holes into the warm cake, spaced about 1 inch apart. Ensure the holes go nearly all the way to the bottom of the pan.
  8. Pour the Soak: Immediately and slowly pour the entire Oreo Cookie Pudding mixture evenly over the poked cake, making sure the pudding settles into all the holes.
  9. Chill (The Waiting Game): Cover the cake loosely with plastic wrap and refrigerate for a minimum of 4 hours, but preferably overnight, until the pudding is completely set and the cake is fully cooled.
  10. Prepare Whipped Cream: In a chilled bowl, beat the heavy whipping cream, powdered sugar, and vanilla extract until stiff peaks form.
  11. Finish the Cake: Spread the prepared whipped cream evenly over the chilled, set cake.
  12. Garnish: Scatter the coarsely chopped Oreo cookies generously over the whipped topping.
  13. Slice and serve. Store leftovers covered in the refrigerator.