Milk Chocolate Stuffed Jack-O-Lantern Cookies

Ingredients

* 1 1/2 cups (3 sticks) salted butter, softened

* 1 1/4 cups light brown sugar, packed

* 1 tablespoon pure vanilla extract

* 2 large eggs, at room temperature

* 4 1/2 cups all-purpose flour

* 1 teaspoon baking soda

* 1 teaspoon cinnamon

* 1/2 teaspoon ginger

* 1/4 teaspoon nutmeg

* 1/2 teaspoon salt

* 12 oz milk chocolate, melted

Directions

Prepare the Dough:

1. In a large mixing bowl, cream together butter, brown sugar, and vanilla extract until light and fluffy, about 3-5 minutes.

2. Add eggs one at a time, mixing until well combined.

3. Add flour, baking soda, cinnamon, ginger, nutmeg, and salt. Mix until the dough forms a ball.

Roll and Cut the Cookies:

1. Generously flour a work surface and divide the dough in half.

2. Flatten each half into a disk and roll out the dough to about 1/4-inch thickness.

3. Using a pumpkin-shaped cookie cutter, cut out the cookies. Transfer to a parchment-lined baking sheet.

4. For half of the cookies, cut out jack-o-lantern faces using a paring knife or smaller cookie cutter.

5. Freeze the cookies for 15-20 minutes to firm up.

Bake the Cookies:

1. Preheat the oven to 350°F (175°C).

2. Bake on the middle rack for 8-12 minutes, or until lightly golden around the edges.

3. Cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.

Prepare the Cinnamon Sugar Topping:

1. Melt 2 tablespoons of butter in a small pan over medium heat until it turns a light golden brown and gives off a toasted aroma, about 2-3 minutes.

2. Let cool slightly, then brush over the top of the jack-o-lantern face cookies. Dust with cinnamon sugar.

Assemble the Cookies:

1. Spread the melted milk chocolate over the flat (non-face) cookies.

2. Gently place the jack-o-lantern face cookies on top of the chocolate-covered cookies, pressing slightly to adhere.

3. Let the chocolate set before serving.

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