Cream together salted butter, light brown sugar, and vanilla extract in a bowl until light and fluffy, about 3-5 minutes.

Gradually add in eggs and mix thoroughly until combined.

In a separate bowl, whisk together all-purpose flour, baking soda, cinnamon, and salt before slowly incorporating into the wet mixture to form a soft dough.

Roll out dough on a floured surface to 1/4-inch thickness, cut out shapes using a pumpkin cookie cutter.

Chill cookie cutouts in the freezer for 15-20 minutes before baking.

Preheat oven to 350°F (175°C) and bake cookies for 8-12 minutes until lightly golden on the edges.

Cool cookies on a wire rack before adding the chocolate filling.

Melt milk chocolate in a microwave-safe bowl, then spread on the flat side of the bottom cookie and sandwich with a face-cut cookie.

Melt butter and brush generously over the tops of each assembled cookie, then dust with cinnamon sugar.