01 - Preheat oven to 350°F. Line a 12-cup muffin tin with cupcake liners.
02 - Set one whole Oreo cookie at the bottom of each cupcake liner.
03 - In a medium bowl, whisk together the flour, cocoa powder, baking soda, and salt until evenly distributed.
04 - In a large bowl, beat the softened butter and granulated sugar together using an electric mixer until light and fluffy, approximately 3 minutes.
05 - Add the eggs one at a time, mixing thoroughly after each addition until fully incorporated.
06 - Blend in the buttermilk, vanilla extract, and red food coloring until the mixture is smooth and evenly colored.
07 - Gradually add the dry ingredient mixture to the wet ingredients, mixing on low speed until just combined. Avoid overmixing.
08 - Divide the batter evenly among the prepared cupcake liners, filling each approximately 3/4 full over the Oreo cookie base.
09 - Bake for 18 to 20 minutes, or until a toothpick inserted into the cupcake portion (avoiding the Oreo) comes out clean. Transfer to a wire rack and cool completely.
10 - Beat the softened cream cheese and butter together until smooth and creamy. Add the sifted powdered sugar and vanilla extract, then mix until light and fluffy. Gently fold in the crushed Oreo cookies.
11 - Pipe or spread the frosting generously onto the fully cooled cupcakes. Garnish with additional Oreo crumbs or mini Oreo cookies if desired.