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Milk Chocolate Stuffed Jack-O’-Lantern Cookies

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Milk Chocolate Stuffed Jack-O’-Lantern Cookies are festive fall treats made with spiced brown sugar cookies filled with creamy milk chocolate. These sandwich cookies are carved with fun jack-o’-lantern faces and dusted with cinnamon sugar for extra seasonal charm.

Ingredients

  • 1 cup unsalted butter, softened
  • 1 cup brown sugar
  • 1/2 cup granulated sugar
  • 1 large egg
  • 2 teaspoons vanilla extract
  • 2 1/2 cups all-purpose flour
  • 1 teaspoon baking soda
  • 1 teaspoon ground cinnamon
  • 1/2 teaspoon ground nutmeg
  • 1/2 teaspoon ground ginger
  • 1/4 teaspoon salt
  • Milk chocolate squares or bars (enough for 12 sandwich cookies)
  • Cinnamon sugar mixture (for dusting)

Instructions

  1. Cream together butter, brown sugar, and granulated sugar until light and fluffy.
  2. Beat in the egg and vanilla extract until smooth.
  3. In a separate bowl, whisk together flour, baking soda, cinnamon, nutmeg, ginger, and salt.
  4. Add dry ingredients to the wet mixture and mix until just combined.
  5. Roll out dough on a floured surface and cut into pumpkin shapes using a cookie cutter.
  6. Carve jack-o’-lantern faces into half of the cookies using a small knife.
  7. Place a piece of milk chocolate in the center of the uncut cookies and top with a face cookie, pressing edges to seal.
  8. Transfer to a baking sheet and bake at 350°F (175°C) for 10–12 minutes until edges are golden.
  9. While warm, dust lightly with cinnamon sugar, then let cool completely.

Notes

  • Chill the dough before baking to prevent spreading.
  • Use dark or white chocolate for a flavor variation.
  • Add a layer of caramel with the chocolate for extra indulgence.
  • Use store-bought dough for a shortcut, but homemade yields better flavor.
  • Store cookies at room temperature for 4 days or freeze for up to 2 months.

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