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Milk Chocolate Stuffed Jack O' Lantern Halloween Cookies

Easy Milk Chocolate Stuffed Jack O' Lantern Halloween Cookies

Delicious Easy Milk Chocolate Stuffed Jack O' Lantern Halloween Cookies recipe with step-by-step instructions.
Prep Time 15 minutes
Cook Time 30 minutes
Total Time 45 minutes
Servings 4
Calories 4800 kcal

Ingredients
  

For the cookie dough:

  • 1 1/2 cups salted butter, softened (3 sticks)
  • 1 1/4 cups packed light brown sugar
  • 1 tbsp pure vanilla extract
  • 2 large eggs, room temperature
  • 4 1/2 cups all-purpose flour
  • 1 tsp baking soda
  • 1 tsp ground cinnamon
  • 1/2 tsp ground ginger
  • 1/4 tsp ground nutmeg
  • 1/2 tsp salt

For the chocolate filling:

  • 12 oz melted milk chocolate

For the topping:

  • 2 tbsp salted butter
  • 3 tbsp cinnamon sugar

Instructions
 

  • In a large mixing bowl, cream together the softened butter, brown sugar, and vanilla extract until the mixture is light and fluffy, about 3-5 minutes. Beat in the eggs, one at a time, mixing until fully incorporated. Add the flour, baking soda, ground cinnamon, ground ginger, ground nutmeg, and salt. Mix until just combined and the dough forms a cohesive ball. I recommend scraping the bowl a few times to make sure everything is well incorporated.
  • Generously flour your work surface to prevent sticking. Divide the cookie dough from Step 1 in half and flatten each portion into a disk. Roll out each disk to about 1/4-inch thickness. Use a pumpkin-shaped cookie cutter to cut out cookies, transferring them carefully to a parchment-lined baking sheet. For half of the cookies, use a paring knife or small cutter to cut out eyes and a mouth. Place the baking sheet in the freezer and chill for 15-20 minutes until the dough is firm. Gather scraps, reroll, and repeat with remaining dough.
  • Preheat your oven to 350°F (175°C). Bake the chilled cookies from Step 2 on the middle rack for 8-12 minutes, or until just lightly golden brown. Avoid overbaking to keep the cookies soft. Allow the cookies to cool on the baking sheet for 5 minutes, then transfer them to a wire rack to cool completely.
  • In a medium pot, melt the salted butter over medium heat. Cook, stirring often, until the butter begins to brown and smells toasted, about 2-3 minutes. Remove from heat and let it cool for 5 minutes. Brush the tops of the pumpkin-face (top half) cookies from Step 3 with the browned butter, then sprinkle generously with cinnamon sugar. I love how browning the butter adds a deep, nutty flavor to the finished cookies.
  • Spread the melted milk chocolate over the base of the plain cookies (the ones without faces) from Step 3. Place the decorated pumpkin-face cookies (from Step 4) on top of the chocolate-covered bases, pressing gently to create a sandwich. Serve immediately, or let the chocolate set before storing cookies in an airtight container for up to 3 days. For a fun twist, sometimes I pop them in the fridge for 10 minutes to make the chocolate set extra fast.