Whisk the dry ingredients. In a medium bowl, whisk flour, cocoa, baking powder, baking soda, and salt until evenly combined. Set aside.
Mix the wet ingredients. In a large bowl, whisk granulated sugar, brown sugar, melted butter, and oil until glossy.
Add the egg, vanilla, and vinegar (if using). Whisk until smooth.
Color the dough. Add red gel food coloring to the wet mixture. Start with 1 tablespoon and adjust until you have a deep red.
The color lightens a bit as it bakes, so go slightly darker than you want the final cookies to be.
Combine wet and dry. Add the dry ingredients to the wet and fold with a spatula just until no dry spots remain. The dough will be thick and slightly sticky.
Chill. Cover and refrigerate for at least 1 hour, or up to overnight. This step keeps the cookies thick and helps the crinkle effect.
Preheat and prep. Heat the oven to 350°F (175°C).
Line two baking sheets with parchment paper.
Set up the coating station. Place some granulated sugar in a shallow bowl and powdered sugar in another. Rolling in granulated sugar first helps the powdered sugar stay bright and not melt into the dough.
Scoop and roll. Using a 1.5-tablespoon scoop, portion the chilled dough. Roll balls lightly in granulated sugar, then generously in powdered sugar, making sure they’re fully coated.
Bake. Arrange on the baking sheets, spacing about 2 inches apart.
Bake 9–11 minutes, until the cookies puff and crack with set edges but soft centers. They’ll continue to firm up as they cool.
Cool. Let cookies rest on the sheet for 5 minutes, then move to a wire rack to cool completely.