Make the Spiced Cookie Dough:
In a large bowl, cream together the softened butter and both sugars until light and fluffy. Beat in the eggs one at a time, then the vanilla. In a separate bowl, whisk together the flour, baking powder, baking soda, salt, cinnamon, and nutmeg. Gradually add the dry ingredients to the wet, mixing until just combined. Fold in the ½ cup of milk chocolate chips.

Chill and Roll the Dough:
Divide the dough in half, wrap each in plastic wrap, and chill for at least 1 hour. Once chilled, preheat your oven to 375°F (190°C) and line baking sheets with parchment paper. On a floured surface, roll one half of the dough to ¼-inch thickness.

Cut and Bake the Cookies:
Use a pumpkin-shaped cookie cutter to cut out the cookies. On half of the cut-outs, use a small knife or mini cutters to create Jack-O’-Lantern faces. Place all cookies on the prepared baking sheets and bake for 8-10 minutes, until the edges are lightly golden. Let them cool on the baking sheet for a few minutes before transferring to a wire rack to cool completely.

Stuff, Decorate, and Assemble:
Once cooled, melt the 1 cup of milk chocolate chips for the filling. Spread a layer of melted chocolate on a solid pumpkin cookie, then gently place a Jack-O’-Lantern-faced cookie on top to create a sandwich. Use icing to add details if desired. Let the chocolate set before serving.