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Milk Chocolate Stuffed Jack-O'-Lantern Cookies

Delve into the festive spirit with these fun and delicious cookies stuffed with rich milk chocolate. Perfect for Halloween or any gathering!
Prep Time 30 minutes
Cook Time 12 minutes
Total Time 42 minutes
Course Dessert, Snack
Cuisine American, Halloween
Servings 24 cookies
Calories 180 kcal

Ingredients
  

Cookie Dough Ingredients

  • 1.5 cups 1 1/2 cups salted butter, softened
  • 1.25 cups 1 1/4 cups light brown sugar, packed
  • 1 tablespoon 1 tablespoon pure vanilla extract
  • 2 2 eggs (room temperature)
  • 4.5 cups 4 1/2 cups all-purpose flour
  • 1 teaspoon 1 teaspoon baking soda
  • 1 teaspoon 1 teaspoon cinnamon
  • 0.5 teaspoon 1/2 teaspoon ground ginger
  • 0.25 teaspoon 1/4 teaspoon nutmeg
  • 0.5 teaspoon 1/2 teaspoon salt

Chocolate Filling & Decoration

  • 12 ounces 12 ounces milk chocolate, melted
  • 2 tablespoons 2 tablespoons salted butter (for browning)
  • 3 tablespoons 3 tablespoons cinnamon sugar (for topping)

Instructions
 

Preparation

  • Preheat your oven to 350°F (175°C). Line your baking sheets with parchment paper.
  • In a large mixing bowl, beat together the softened butter, light brown sugar, and vanilla extract until light and fluffy (about 3 to 5 minutes).
  • Add the eggs one at a time, mixing well after each addition.
  • In another bowl, mix flour, baking soda, cinnamon, ginger, nutmeg, and salt, then gradually add to the wet ingredients until the dough begins to form a ball.

Shaping the Cookies

  • Flour your work surface and divide the dough in half, flattening into disks.
  • Roll out one disk to about 1/4 inch thickness and cut out pumpkin shapes.
  • Cut out faces on half of the cookies.
  • Freeze the cut-out cookies for 15 to 20 minutes.

Baking and Assembling

  • Bake cookies for 8 to 12 minutes until edges are lightly golden.
  • Melt 2 tablespoons of salted butter until browned, then brush it over the top half of cookies after they have cooled for 5 minutes.
  • Sprinkle cinnamon sugar on top, then spread melted chocolate on the backs of the remaining cookies and sandwich them together.

Notes

Store in an airtight container at room temperature for up to 3 days or freeze for longer storage. For best results, avoid overmixing the dough and ensure proper chilling before baking.
Keyword Chocolate Cookies, Fall Baking, Halloween Cookies, Jack-O'-Lantern Cookies, Stuffed Cookies