Preheat oven to 375 degrees F. Line two baking sheets with parchment paper.
In a medium bowl, combine flour, cocoa, baking soda, baking powder, and salt. Set aside.
In a large bowl, cream together butter and brown sugar for 2-3 minutes with a stand (or hand) mixer until light in color and fluffy. Add egg and vanilla, mixing until fully combined.
Alternately add in flour mixture and milk (beginning and ending with flour), and mix until just combined.
Using a small or medium cookie scoop, drop dollops of batter 2 inches apart on baking sheets (you will need to work in batches). Bake for 8-10 minutes until the cookies are puffy and spring back when gently touched.
Remove from oven and allow to cool on baking sheets for 5 minutes before moving to cooling rack and continuing with the remaining batter.
For the Swirl
In a clean bowl, cream butter for 30 seconds on high speed.
Add powdered sugar to butter ½ cup at a time, mixing on low and allowing it to combine before adding more. Add until it reaches your desired sweetness.
Add in milk/cream a Tablespoon at a time, until the desired consistency is reached. Then add vanilla bean paste. Beat together on medium-high speed for 3-5 minutes until fluffy.
Remove approximately half of the icing and place in a separate bowl. Add peppermint extract and desired amount of red food coloring to remaining icing and continue to beat 1 more minute until incorporated.
Stripe a piping bag on one side with the red peppermint icing, and carefully stripe the other side with the vanilla.
Flip half of the cookies so the flat sides face up, and fill them with icing, swirling from the outside to the inside. Top with remaining cookies, serve, and enjoy!
Amount Per Serving
Calories296kcalCalories from fat 107
% Daily Value
Percent Daily Values are based on a 2,000 calorie diet. Your daily values may be higher or lower depending on your calorie needs: