Combine dry ingredients. In a medium bowl, whisk together the flour, cocoa powder, baking powder, baking soda, and salt until well blended. Set aside.
Cream butter and sugar. In a large bowl, beat the butter and granulated sugar with an electric mixer on medium speed until light and fluffy, about 2-3 minutes. Scrape down the sides of the bowl as needed.
Add eggs and flavorings. Beat in the eggs one at a time, then add vanilla extract, buttermilk, and red food coloring. Mix until the color is uniform and vibrant, about 1 minute.
Incorporate dry ingredients. Gradually add the flour mixture to the wet ingredients on low speed, mixing just until combined. Don’t overmix or your cookies will be tough.
Chill the dough. Cover the bowl with plastic wrap and refrigerate for at least 2 hours or overnight. This step is essential for the proper texture and to make the dough easier to handle.
Preheat and prepare. When ready to bake, preheat the oven to 350°F (175°C). Line baking sheets with parchment paper. Place the granulated and powdered sugars in separate small bowls.
Shape cookies. Using a tablespoon or cookie scoop, portion the dough into 1-inch balls. Roll each ball in granulated sugar first (this helps the powdered sugar stick better), then generously coat in powdered sugar.
Arrange and bake. Place the coated dough balls on prepared baking sheets about 2 inches apart. Bake for 10-12 minutes until the edges are set but the centers still appear slightly soft.
Cool properly. Allow cookies to cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely. The crinkles will become more pronounced as they cool.