Preheat and prep: Set the oven to 350°F (175°C).
Line two baking sheets with parchment paper.
Whisk dry ingredients: In a bowl, whisk flour, cocoa powder, baking powder, baking soda, and salt until evenly combined.
Cream butter and sugars: In a large mixing bowl, beat the softened butter with granulated and brown sugar until light and fluffy, about 2–3 minutes.
Add eggs and flavorings: Beat in the eggs one at a time. Mix in the vanilla, vinegar, and buttermilk until smooth.
Color the dough: Add the red food coloring. Start with 1 teaspoon, then add more to achieve a deep red.
Mix well so the color is uniform.
Combine wet and dry: Add the dry ingredients to the wet in two additions. Mix on low just until no dry streaks remain. The dough will be soft and a bit sticky.
Chill: Cover the bowl and chill the dough for 30–45 minutes.
This firms it up for easy rolling and helps keep the cookies thick.
Prepare the coatings: Add the extra 1/4 cup granulated sugar to one shallow bowl and the powdered sugar to another.
Portion and roll: Scoop tablespoon-size portions (about 1 heaping tablespoon or 30 g). Roll each into a ball.
Double coat: Roll each dough ball first in granulated sugar to create a dry surface, then generously in powdered sugar. A thick powdered sugar layer gives the best crinkle effect.
Bake: Place on prepared sheets, spacing about 2 inches apart.
Bake 10–12 minutes, until the tops are crackled and the edges are set. The centers should look slightly soft.
Cool: Let cookies cool on the sheet for 5 minutes, then transfer to a rack. They’ll firm up as they cool but stay chewy.