1. Whisk together flour baking soda ground cinnamon and salt in a bowl and set aside

2. Cream butter light brown sugar and granulated sugar until light and fluffy

3. Add egg and vanilla extract and mix until combined

4. Gradually mix in dry ingredients until a soft dough forms

5. Divide dough in half flatten into disks wrap and chill for 30 minutes

6. Preheat oven to 350°F and line baking sheets with parchment paper

7. Roll one dough disk to 1/4 inch thickness and cut with pumpkin-shaped cookie cutters into pairs

8. Carve jack-o-lantern faces into half the cookies using a small knife

9. Arrange cookies 1 inch apart on baking sheets and bake for 9–11 minutes until edges are golden

10. Cool on baking sheet 5 minutes then transfer to a wire rack

11. Melt chocolate chips heavy cream and butter over simmering water stirring until smooth and glossy

12. Allow filling to cool until thick enough to spread

13. Spread or pipe about 1 teaspoon of chocolate filling onto each bottom cookie

14. Top with carved cookies pressing gently so filling peeks through

15. Let cookies set at room temperature for 15–20 minutes

16. Dust with powdered sugar or add food gel accents before serving