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Triple Threat Cupcakes

Servings 24 cupcakes



  • 24 Oreos split in half cream sides only
  • 1 box white cake mix
  • 3 eggs
  • 1/3 cup oil
  • 1 cup milk whole, buttermilk, or whatever you have
  • 3/4 cup sour cream
  • 1 tablespoon vanilla extract

Cookie Dough Filling:

  • 3/4 cup butter softened
  • 5 tablespoons brown sugar packed
  • 1 tablespoon sugar
  • 1 1/2 cups flour
  • 7 oz sweetened condensed milk
  • 1 teaspoon vanilla extract
  • 1/4 cup mini chocolate chips

Brownie Frosting:

  • 1 cup butter softened
  • 1/2 cup unsweetened cocoa powder
  • 2 teaspoons vanilla extract
  • 1 tablespoon milk
  • 3-4 cups powdered sugar
  • 5-7 brownies crumbled


  1. 1. Preheat oven to 350 degrees and line pans with cupcake liners.
  2. 2. Place your Oreo halves cream side up on the bottom of each liner. (Feel free to eat the non-cream side as you bake.)
  3. 3. Sift cake mix into a small bowl and set aside.
  4. 4. In a large bowl, use a whisk to combine eggs, oil, milk, sour cream and vanilla extract.
  5. 5. Add cake mix and stir until smooth.
  6. 6. Fill cupcake liners (over oreo halves) 3/4 full and bake for 17-22 minutes, or until an inserted knife comes out clean.
  7. 7. Cookie Dough Filling: Combine all ingredients in a stand mixer, except chocolate chips, and beat until smooth. Then fold in chocolate chips. Add more flour if needed to thicken.
  8. 8. Use a knife to cut out small holes of each cupcake and fill with cookie dough filling. You can do this while the cupcakes are still warm.
  9. 9. Frosting: Beat butter for 2 minutes. Add cocoa, vanilla extract and milk. Scrape down the bowl as needed. Slowly add powdered sugar until you reach your desired consistency. Add a little more milk if the frosting becomes too thick. Fold in brownie crumbles.
  10. 10. Pipe frosting onto cupcakes over the cookie filling and top with sprinkles, mini chocolate chips or Oreos.
  11. 11. Taste bud party!