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Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Milk Chocolate Stuffed Jack-O’-Lantern Cookies are soft, spiced pumpkin cookies with a gooey milk chocolate center, perfect for Halloween and autumn festivities. These cookies combine comforting seasonal flavors with a fun, festive design that makes them ideal for parties, gifting, or sharing with family.

Ingredients

Scale

Dry Ingredients

  • 2 1/2 cups all-purpose flour
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon baking powder
  • 1 teaspoon ground cinnamon
  • 1 1/2 teaspoons pumpkin pie spice
  • 1/2 teaspoon salt

Wet Ingredients

  • 1 cup unsalted butter, softened
  • 1/2 cup granulated sugar
  • 1/2 cup brown sugar, packed
  • 1 large egg
  • 3/4 cup pumpkin puree
  • 1 teaspoon vanilla extract

Filling

  • Milk chocolate squares or chunks (about 1 small piece per cookie)

Instructions

  1. Prepare the Dough: In a medium bowl, whisk together all-purpose flour, baking soda, baking powder, cinnamon, pumpkin pie spice, and salt. In a separate large bowl, beat the softened butter with granulated and brown sugars until creamy and fluffy. Add the egg, pumpkin puree, and vanilla extract, mixing until fully combined. Gradually incorporate the dry ingredients into the wet mixture, forming a soft dough that’s slightly sticky but manageable.
  2. Shape the Cookies: Roll out the dough on a lightly floured surface to about 1/4 inch thickness. Use a Jack-O’-Lantern-shaped cookie cutter to cut out as many shapes as possible. Then, cut out an equal number of solid cookie shapes without faces to act as lids. Alternatively, prepare rounds if you don’t have a themed cutter.
  3. Stuff with Milk Chocolate: Place a small piece of milk chocolate in the center of each Jack-O’-Lantern cutout. Gently press the solid cookie “lid” on top, sealing the edges by lightly pinching or using a fork to create a decorative border that locks in the filling.
  4. Carve the Faces: Carefully cut out the Jack-O’-Lantern features (eyes, nose, mouth) on the top cookie layer using a small paring knife or cookie-carving tool. This makes the milk chocolate filling peek through during baking, adding to the eerie effect.
  5. Bake the Cookies: Preheat your oven to 350°F (175°C). Place the stuffed cookies on a parchment-lined baking sheet and bake for 10-12 minutes or until the edges are lightly golden. Baking will soften the cookie and melt the milk chocolate inside.
  6. Cool and Enjoy: Allow the cookies to cool on the pan for 5 minutes before transferring to a wire rack. The chocolate center will thicken as they cool, creating an indulgent surprise with every bite.

Notes

  • Chill the dough: Refrigerate the dough for 30 minutes before rolling to prevent sticky handling and maintain shape.
  • Seal edges well: Press cookie layers firmly together to avoid chocolate leaking during baking.
  • Use quality chocolate: Opt for good-quality milk chocolate to ensure a smooth, creamy filling.
  • Don’t overbake: Remove cookies once edges turn golden to keep them soft and chewy.
  • Cut shapes carefully: Use a sharp knife or fine cookie cutters to create detailed Jack-O’-Lantern faces.

Nutrition

Keywords: pumpkin cookies, Halloween cookies, stuffed cookies, spiced cookies, milk chocolate cookies, festive cookies, autumn treats, Jack-O’-Lantern cookies