Ingredients
Equipment
Method
Bake the cookie base
- Preheat the oven to 350°F (175°C) and line two baking sheets with parchment paper.
- Beat the softened butter and granulated sugar for 2 minutes, until light and fluffy, then scrape the bowl if needed.
- Beat in the egg and vanilla extract until smooth and fully incorporated, then stop and scrape the sides.
- Add the all-purpose flour, baking powder, baking soda, salt, and ground cinnamon, and mix on low just until the dough comes together.
- Scoop 1/4-cup portions of dough and roll them into balls, placing 6 per sheet about 3 inches apart.
- Flatten each ball with the bottom of a glass into a 3-inch disc about 1/2 inch thick.
- Bake for 11–13 minutes at 350°F (175°C), until the edges are just set and the centers look pale and soft; do not let them brown on top.
- While the cookies are still hot, press the back of a 1/4-cup measuring cup gently into the center of each cookie to make a shallow well and create a visible depression.
- Cool the cookies completely on the pan for about 30 minutes so the wells hold their shape.
Make the pumpkin pie filling
- Beat the softened cream cheese until smooth, then continue until no lumps remain.
- Beat in the pumpkin purée, packed light brown sugar, heavy cream, pumpkin pie spice, vanilla extract, and salt until creamy and evenly colored.
- Fold in the graham cracker crumbs so the filling thickens slightly, then chill for 15 minutes to set up for filling.
Assemble and chill
- Whip the cold heavy whipping cream with powdered sugar and vanilla extract until stiff peaks form, stopping when the peaks stand upright.
- Spoon about 2 tbsp of pumpkin filling into the well of each cooled cookie and smooth it flat so it sits level.
- Pipe a swirl of whipped cream on top of each cookie and dust lightly with ground cinnamon for a warm speckled top.
- Chill the assembled cookies for 20 minutes so the filling and topping firm up, then serve cold.
Notes
Pro tip: keep the cookie centers pale and soft (no browning) so the wells stay tender after cooling. Store covered in the refrigerator up to 4 days; freeze assembled cookies for up to 2 months for best texture (thaw overnight in the fridge). Dietary swap: use reduced-fat cream cheese and swap heavy cream for coconut cream if you want a lighter, dairy-reduced version, noting the filling may be slightly less firm.
