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In a bowl, whisk together the flour, cocoa powder, baking powder, baking soda, and salt. Set aside.
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In another bowl, beat the softened butter and white sugar until pale and fluffy (about 3 minutes).
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Gradually add the eggs, one at a time, mixing well after each addition.
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Add the vanilla, milk, vinegar, and red food coloring, and mix until combined.
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Slowly add the dry ingredients to the wet ingredients. Mix just until everything is incorporated.
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Cover the dough with plastic wrap and chill in the fridge for at least 2 hours, or up to overnight.
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Preheat your oven to 350°F and line a baking sheet with parchment paper.
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Once the dough is firm, scoop about 1 tbsp and roll into balls.
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Roll the dough balls in powdered sugar until they’re fully coated, then place them on the prepared baking sheet.
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Bake for 9-10 minutes, rotating the pan halfway through baking.
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Remove from the oven and let them sit on the baking sheet for 5 minutes.
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Transfer the cookies to a cooling rack to cool completely before filling.