Preheat the oven to 350°F. Line a cupcake pan with liners.

In the bowl of a stand mixer fitted with the paddle attachment, add the butter, cane sugar, and vanilla extract. Mix on low until combined and there are no butter chunks.

Add the eggs, milk, and sour cream and mix on low until combined. Add the cake flour, baking powder, and sea salt and mix on low until combined into a smooth batter. Be sure to scrape down the sides of the bowl to ensure even mixing.

Fill the cupcake liners three-quarters full. Bake for 20 to 23 minutes or until a toothpick inserted in the center comes out clean. Allow to cool completely in the baking pan.

To make the frosting: In a small bowl, add the Oreo cookies and just break them up with your hands into small pieces. Set aside.

In the bowl of a stand mixer fitted with the paddle attachment, add the butter, powdered sugar, and heavy whipping cream. Mix on low until combined and there are no chunks of butter. Continue to whip and turn mixer up to high speed and whip for 1 to 3 minutes or until light and fluffy.

Add in the chopped Oreo cookies and mix on high to combine completely. Make sure to scrape down the sides of the bowl and mix again to ensure cookies are well combined. Transfer to a piping bag with Ateco tip #827.

Frost each cupcake by spiraling frosting onto each one. Top with half a cookie.

Store in an airtight container for up to 3 days.