Ingredients for 10 cupcakes

For the cupcakes:

¼ cup brown sugar
¼ cup cocoa powder
¼ cup Nutella
¼ cup red wine, any kind you like
¼ teaspoon ground cinnamon
¼ cup unsalted butter, at room temperature
¼ teaspoon salt
½ teaspoon baking powder 
½ teaspoon vanilla extract
1 cup all-purpose flour
1 egg 
1 teaspoon baking soda

2 tablespoons granulated sugar
10 Oreos

For the filling:

½ cup Nutella
5 Oreos

For the frosting:

¼ cup granulated sugar
½ cup unsalted butter, at room temperature
1 cup red wine, any kind you like
1 teaspoon vanilla extract
2 cups powdered sugar
salt, to taste

Directions

Preheat oven to 350°F. Line 10 muffin cups with cupcake liners. Set aside.

The cupcakes. In a medium bowl, sift together the flour, cocoa powder, baking soda, baking powder, salt, and cinnamon. In a large bowl, cream the butter and sugars together until fluffy. Add the egg and beat to combine. Scrape down the sides of the bowl as needed. Beat in the vanilla extract. Stir in Nutella and red wine until evenly combined. Slowly add the flour mixture to the wet ingredients and mix until just combined. Place an Oreo cookie on the bottom of each cupcake liner. Pour batter over each Oreo cookie and fill each cupcake liner about ¾ of the way full. Bake the cupcakes for about 20 minutes or until a toothpick inserted in the center comes out clean. Remove from oven and place on a wire rack to cool completely.

The filling. In a ziplock bag, place the Oreos and use a mallet to crush the cookies into small pieces. In a small bowl, combine Nutella with crushed Oreos. Set aside.

The frosting. In a small saucepan, combine red wine and sugar. Cook over medium heat, stirring, until sugar dissolves and wine comes to a boil. Reduce heat and simmer for 20 minutes (until the liquid is reduced to about ¼ cup or a light syrup texture). Let to cool.

Beat the butter until until smooth and creamy. Slowly add in powdered sugar (½ cup at a time), vanilla, and ¼ cup of prepared wine syrup. Beat until no lumps remain. Taste the frosting and add salt to cut the sweetness, if you prefer.

Assembling the cupcakes. Cut out the center of each cupcake with a sharp knife. Fill the cupcakes with Nutella & Oreo filling. Transfer the frosting to a piping bag fitted with a decorative tip. Pipe frosting into a swirl on each cupcake.