1. Cream together softened butter, light brown sugar, and granulated sugar until light and fluffy.

2. Beat in the egg and vanilla extract until fully combined.

3. Whisk together flour, baking powder, ground cinnamon, and salt; gradually add to the wet ingredients.

4. If using, add orange food coloring and mix until color is even.

5. Form the dough into a disk, wrap in plastic, and refrigerate for 30–40 minutes.

6. Preheat oven to 350°F (175°C) and line baking sheets with parchment paper.

7. Roll the chilled dough to 1/4-inch thickness on a lightly floured surface and cut pumpkin shapes.

8. Use a small knife to carve eyes, noses, and smiles into half of the cookies.

9. In a microwave-safe bowl or small saucepan, melt milk chocolate chips with heavy cream or milk, stirring until smooth.

10. Place the uncarved cookie bases on baking sheets and spoon about one teaspoon of melted chocolate into the center of each.

11. Top with the carved face cookies and press edges gently to seal the filling.

12. Bake for 10–12 minutes until the cookie edges are light golden brown.

13. Allow cookies to cool on the baking sheet for a few minutes, then transfer to a wire rack to finish setting.

14. Decorate with candy eyes, icing, sprinkles, or edible glitter as desired before serving.