1. Beat the softened cream cheese until smooth, then add powdered sugar, vanilla, and a pinch of salt. Beat until thick and creamy.

2. Pipe or spoon teaspoon-sized mounds of the filling onto a parchment-lined baking sheet and freeze for at least 30 minutes, until firm.

3. In a medium bowl whisk together the flour, baking soda, baking powder, salt, cinnamon, and pumpkin pie spice. Set aside.

4. In a large bowl whisk the melted butter with the brown sugar and granulated sugar until glossy and well combined.

5. Blot the pumpkin puree with paper towels to remove excess moisture, then whisk it into the butter mixture along with the egg yolk and vanilla extract.

6. Add the dry ingredients to the wet ingredients and gently fold with a spatula just until no dry streaks remain. Cover the bowl and chill the dough for 30–45 minutes.

7. Stir together the granulated sugar and cinnamon for the coating in a small bowl.

8. Scoop about 1 1/2 tablespoons of dough, flatten it into a disc in your hand, place one frozen cheesecake mound in the center, and top with another small piece of dough. Pinch edges to seal, roll into a ball, and coat in the cinnamon sugar.

9. Arrange the cookie dough balls on a parchment-lined baking sheet, leaving space between each one.

10. Bake at 350°F (175°C) for 11–13 minutes, until the edges are set and the tops look puffy and matte but the centers are still soft.

11. Cool the cookies on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.

12. Pair the cooled cookies by size. Pipe or spread cheesecake filling on the flat side of one cookie and sandwich with its partner.

13. For the drizzle, whisk powdered sugar, vanilla, and just enough milk or cream to make a thick but pourable icing. Drizzle over the tops of the cookie sandwiches and let set before serving.