Preheat Oven: Set your oven to 350°F (175°C) and line a baking sheet with parchment paper.
Cream Butter and Sugars: In a large bowl, cream together ½ cup butter, ⅔ cup brown sugar, and ½ cup granulated sugar until smooth and creamy.
Add Wet Ingredients: Mix in 1 egg, 1 teaspoon vanilla extract, 1 teaspoon white vinegar, and 1–2 teaspoons red gel food coloring until well combined.
Incorporate Dry Ingredients: Gradually add ¼ cup cocoa powder, 1¾ cups all-purpose flour, ¼ teaspoon salt, 2 tablespoons cornstarch, and ½ teaspoon baking powder. Mix until just combined; avoid overmixing.
Shape Cookies: Using a large cookie scoop, form 9 equally sized dough balls. Place them on the prepared baking sheet and gently flatten to about ½ inch thickness.
Bake: Bake in the preheated oven for 10 minutes. Allow cookies to cool on the baking sheet for 10–15 minutes before transferring to a wire rack to cool completely.
Prepare Frosting: In a separate bowl, beat 4 oz softened cream cheese and 3 tablespoons softened butter until smooth. Add 1 teaspoon vanilla extract and 1 cup powdered sugar; beat until fluffy.
Frost Cookies: Once cookies are completely cooled, pipe or spread the cream cheese frosting on top. Optionally, sprinkle with red velvet crumbs for decoration.