In a large mixing bowl, cream the softened butter, brown sugar, and vanilla together until light and fluffy, about 3-5 minutes. Add the eggs one at a time, mixing until evenly combined.

Add the flour, baking soda, cinnamon, ginger, nutmeg, and salt to the butter mixture. Beat until everything is combined and the dough forms a ball.

Generously flour your work surface and divide the dough in half. Flatten each half into a disk, roll out to 1/4-inch thickness, and cut out cookies using a pumpkin cookie cutter. Use a pairing knife or smaller cookie cutter to create eyes and a mouth on half the cookies.

Carefully transfer the cookies to a parchment-lined baking sheet. Cover and place them in the freezer for about 15-20 minutes until they’re firm. Roll out any leftover scraps and repeat with the remaining dough.

Preheat your oven to 350°F. Bake the cookies for 8-12 minutes on the middle rack for soft cookies, or until they are just lightly golden brown. Let them cool on the baking sheet for 5 minutes before transferring to a wire rack.

In a medium pot, melt the butter over medium heat and allow it to brown slightly, about 2-3 minutes, stirring often. Remove from heat and let cool for 5 minutes. Brush the top half of the cookies with this brown butter and sprinkle with cinnamon sugar.

Spread melted milk chocolate over the bottom half of the cookies without the faces. Gently place the pumpkin-faced cookies on top, pressing to adhere.