Ingredients:

  • 1 ¾ cups All-Purpose Flour
  • 2 cups Granulated Sugar
  • ¾ cup Unsweetened Cocoa Powder
  • 1 teaspoon Baking Soda
  • ½ teaspoon Baking Powder
  • 1 teaspoon Salt
  • 2 Large Eggs
  • 1 cup Buttermilk
  • ½ cup Vegetable Oil
  • 1 teaspoon Vanilla Extract
  • 1 cup Hot Water or Freshly Brewed Hot Coffee
  • 1 (14-ounce/397g) can Sweetened Condensed Milk
  • 2 large boxes Instant Chocolate Pudding Mix (approx. 379g total)
  • 4 cups Cold Whole Milk
  • 2 cups Cold Heavy Whipping Cream
  • ½ cup Powdered Sugar
  • 1 teaspoon Vanilla Extract (for topping)
  • 20–24 Oreo Cookies, crushed

Instructions:

  1. Preheat oven to 350°F (175°C). Grease and flour a 9x13 inch baking pan.
  2. In a large bowl, whisk together the flour, sugar, cocoa powder, baking soda, baking powder, and salt.
  3. Add the eggs, buttermilk, oil, and vanilla extract to the dry ingredients. Beat on medium speed for 2 minutes until just combined.
  4. Slowly stream in the hot water or coffee on low speed until the batter is smooth and thin. Do not overmix.
  5. Pour the batter into the prepared pan and bake for 30–35 minutes, or until a toothpick inserted near the center comes out with moist crumbs attached.
  6. Immediately upon removing the hot cake from the oven, use a long skewer or wooden spoon handle to poke holes all over the surface, spaced about ½ to 1 inch apart, ensuring holes reach nearly to the bottom.
  7. Slowly pour the entire can of sweetened condensed milk evenly over the hot cake, allowing it to seep into all the holes. Set aside to cool completely (at least 1 hour).
  8. While the cake cools, prepare the chocolate pudding mix according to package directions using 4 cups of cold milk. Whisk until thickened slightly, then refrigerate to set slightly.
  9. Once the cake is completely cool, spread the thickened chocolate pudding evenly over the top surface, ensuring it fills all the poke holes. Return to the fridge for at least 3 hours to firm up.
  10. Just before serving, whip the cold heavy cream, powdered sugar, and vanilla extract until stiff peaks form.
  11. Frost the chilled pudding layer generously with the whipped cream and sprinkle the crushed Oreo cookies evenly over the top for the finishing touch.