In a large mixing bowl, cream together 1 cup of softened salted butter, 1 cup of light brown sugar, and 1 tablespoon of pure vanilla extract until light and fluffy, about 3-5 minutes. Add in 2 eggs one at a time, mixing well after each addition. Gradually incorporate 2 ¾ cups of all-purpose flour, 1 teaspoon of baking soda, 1 teaspoon of cinnamon, ½ teaspoon of ground ginger, ¼ teaspoon of nutmeg, and a pinch of salt until a smooth dough forms.

Divide the dough in half and flatten each half into disks. Roll out each disk to a thickness of ¼ inch on a floured surface. Using a pumpkin-shaped cookie cutter, cut out cookies and transfer them to a parchment-lined baking sheet. For half of the cookies, use a knife to create eyes and a mouth to give them that classic jack-o’-lantern look. Freeze the cookie shapes for 15-20 minutes to firm them up.

Preheat your oven to 350°F (175°C). Take the chilled cookies out of the freezer and bake for 8-12 minutes, or until they turn lightly golden around the edges. The centers should still look slightly soft. Once baked, let them cool on wire racks.

In a small saucepan, brown ¼ cup of salted butter over medium heat. Brush this brown butter over the tops of the cooled cookies. Immediately sprinkle with cinnamon sugar.

Spread melted milk chocolate on the flat side of the un-faceted cookies. Carefully place the cookie halves with facial features on top and gently press down to secure them together.