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Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Milk Chocolate Stuffed Jack-O’-Lantern Cookies

These Milk Chocolate Stuffed Jack-O’-Lantern Cookies combine soft, buttery cookie dough with a melty milk chocolate center and festive pumpkin face decorations. Perfect for Halloween parties or baking with kids, they offer a fun, indulgent treat that’s soft, chewy, and rich in flavor.

Ingredients

Scale

Cookie Dough

  • 2 1/4 cups all-purpose flour
  • 1 cup unsalted butter, softened
  • 1/2 cup granulated sugar
  • 1/2 cup brown sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon salt
  • 57 drops orange food coloring

Filling and Decoration

  • Milk chocolate bars or chunks (about 2 ounces, cut into small pieces)
  • Black icing (for decorating jack-o’-lantern faces)

Instructions

  1. Prepare the Dough: Begin by creaming together the softened unsalted butter with the granulated and brown sugar until light and fluffy. Beat in the egg and vanilla extract until well combined. In a separate bowl, sift together the all-purpose flour, baking soda, and salt. Gradually add the dry ingredients to the wet mixture, stirring gently until a soft dough forms. Add a few drops of orange food coloring and mix until the dough is evenly tinted a vibrant pumpkin shade.
  2. Shape the Cookies: Take a small scoop of dough, about one tablespoon, and flatten it slightly in the palm of your hand. Place a small piece of milk chocolate in the center, then gently fold the dough around the chocolate, sealing it completely. Roll into a smooth ball and place on a parchment-lined baking sheet. Repeat until all dough and chocolate are used, spacing cookies a couple of inches apart to allow for spreading.
  3. Carve the Jack-O’-Lantern Faces: Using a quick-drying tool such as the handle of a spoon or a toothpick, gently press or carve simple pumpkin face shapes on the surface of each cookie. Create eyes, noses, and mouths with friendly or spooky expressions. Do not press too hard to avoid breaking the dough, just enough to leave a clear outline.
  4. Bake and Cool: Preheat oven to 350°F (175°C). Bake the cookies for 10 to 12 minutes, or until the edges are just set but the centers remain soft. Once out of the oven, let them cool on the baking sheet for a few minutes before transferring to a wire rack to cool completely, helping retain the gooey chocolate center.
  5. Decorate with Icing: Once cooled, use black icing to trace around the carved faces and fill in details to enhance the jack-o’-lantern look. Allow the icing to set before serving or storing.

Notes

  • Chill the dough for 30 minutes if too soft to handle, which helps with shaping.
  • Seal the chocolate pieces completely within the dough to prevent leaking during baking.
  • Use high-quality milk chocolate for better melting and richer flavor.
  • Do not overbake; remove cookies as soon as edges are set to maintain soft centers.
  • Vary jack-o’-lantern face designs to add personality and fun.

Nutrition

Keywords: Halloween cookies, stuffed cookies, jack-o’-lantern cookies, milk chocolate cookies, festive treats, soft cookies