Preheat and Prep

Preheat your oven to 350°F (175°C). Line baking sheets with parchment paper or silicone baking mats.

Make the Cookie Dough

In a bowl, whisk together the flour, cocoa powder, baking powder, baking soda, and salt. Set aside.

In a large bowl, cream the butter and sugar with an electric mixer until light and fluffy. Add the egg and vanilla extract, mixing until combined.

Gradually add the dry ingredients to the wet mixture, alternating with the buttermilk. Mix until just combined. Add the red food coloring and stir until evenly incorporated.

Bake the Cookies

Use a cookie scoop or spoon to drop small mounds of batter (about 1½ tablespoons each) onto the prepared baking sheets, spacing them about 2 inches apart.

Bake for 10-12 minutes, or until the cookies spring back when lightly pressed.

Allow the cookies to cool on the baking sheets for 5 minutes before transferring them to a cooling rack to cool completely.

Prepare the Cream Cheese Filling

Beat the cream cheese and butter together until smooth and creamy. Gradually add the powdered sugar, mixing until well incorporated. Stir in the vanilla extract.

Assemble the Whoopie Pies

Spread or pipe a generous layer of filling onto the flat side of one cookie.

Top with another cookie to create a sandwich. Repeat with the remaining cookies and filling.