Ingredients:

  • 1 ½ cups (192g) all-purpose flour, plus more for dusting
  • ⅔ cup (60g) unsweetened cocoa powder
  • 1 teaspoon baking soda
  • ½ teaspoon salt
  • ½ cup (1 stick, 113g) unsalted butter, softened
  • ¾ cup (150g) granulated sugar
  • ½ cup (100g) packed light brown sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • ¼ cup (60ml) milk
  • ½ cup (1 stick, 113g) unsalted butter, softened
  • 3 cups (360g) powdered sugar
  • 2 tablespoons heavy cream
  • 1 teaspoon vanilla extract
  • Seeds from 1 vanilla bean (or 1 teaspoon vanilla bean paste)
  • Pinch of salt
  • 4 oz (113g) semi-sweet chocolate chips

Instructions:

  1. Whisk together dry ingredients. Cream butter and sugars, then beat in egg and vanilla. Gradually add dry ingredients, alternating with milk.
  2. Divide dough in half, flatten into discs, wrap in plastic wrap, and chill for at least 1 hour.
  3. Roll out dough to ¼-inch thickness on a lightly floured surface. Cut out cookies with a 2-inch round cutter.
  4. Place cookies on lined baking sheets and bake until just set.
  5. Transfer cookies to a wire rack to cool completely.
  6. Beat butter until light and fluffy. Gradually add powdered sugar, alternating with heavy cream, vanilla, and vanilla bean seeds. Beat until smooth.
  7. Spread filling on the flat side of half the cookies. Top with the remaining cookies.
  8. Melt chocolate chips in a double boiler or microwave until smooth.
  9. Transfer melted chocolate to a piping bag or Ziploc bag with a tiny corner snipped off. Pipe concentric circles on top of each Oreo. Drag a toothpick from the center outwards to create the spiderweb effect.
  10. Let the chocolate set completely before serving.