Make the cheesecake filling first: In a medium bowl, use a hand mixer to beat the cream cheese, powdered sugar, flour, vanilla, and salt until smooth and fluffy (about 2–3 minutes).
6 oz. full-fat cream cheese, 1/3 cup powdered sugar, 2 tsp. all-purpose flour, 1 tsp. vanilla extract, Pinch of salt
Freeze cheesecake balls: Drop teaspoon-sized mounds onto a parchment-lined baking sheet or plate that fits in your freezer. Freeze for at least 1½ hours, or up to 3 days. The colder, the better, so it doesn’t ooze out of the cookies.
Blot the pumpkin: Place the ½ cup of pumpkin puree on a plate or shallow bowl. Add a few layers of paper towels on top and blot it until reduced to ⅓ cup. This step removes excess moisture and helps keep the cookies chewy, not cakey.
1/2 cup 100% pumpkin puree
Mix the wet ingredients: In a large bowl, whisk together the melted butter, brown sugar, and granulated sugar until smooth and glossy.
1 cup unsalted butter, 1 cup dark brown sugar, 1 cup granulated sugar
Add pumpkin & eggs: Add the blotted pumpkin, egg, egg yolk, and vanilla extract. Whisk again until thoroughly combined and creamy.
1 large egg, 1 large egg yolk, 1 Tbsp. vanilla extract
Combine the dry ingredients: In a separate bowl, whisk together the flour, pumpkin pie spice, a pinch of cinnamon, baking soda, and salt.
2 3/4 cups all-purpose flour, 1 Tbsp. pumpkin pie spice, Pinch of cinnamon, 1 tsp. baking soda, 1 tsp. fine salt
Bring the dough together: Gradually stir the dry ingredients into the wet ingredients using a spatula or wooden spoon. Mix until no flour streaks remain, but don’t overmix.
Chill the dough: Cover the dough and chill for at least 30 minutes or up to 24 hours. Chilling helps make it easier to wrap around the frozen cheesecake filling, helps prevent spreading, and makes the dough easier to work with.
Preheat the oven: Preheat to 350°F (175°C). Line a couple of baking sheets with parchment paper.
Assemble cookies: In a small bowl, mix together the sugar and cinnamon (or pumpkin pie spice). Scoop dough into 1½-2 tablespoon-sized balls (about a medium cookie scoop), and flatten into a disk. Place a frozen cheesecake ball in the center and wrap the cookie dough around it, sealing it completely. Roll into smooth balls, then roll in the spiced sugar mixture. Tip: if the dough feels a little sticky, roll it in a little of the cinnamon sugar mixture to help flatten into a disk, stuff the cookie, then roll in more of the cinnamon sugar mixture again.
1/4 cup granulated sugar, 1/2 tsp. pumpkin pie spice
Bake: Arrange dough balls about 2 inches apart on the baking sheet. Bake for 9–11 minutes, or until the edges are set and the centers still look slightly soft. Don’t overbake because they’ll continue to set up on the baking sheet.
Cookie scooting: Use any round object slightly larger than the cookies, like a large round cookie cutter, biscuit cutter, or even the open top of a wide glass or mug. Place the ring around the warm cookie and gently swirl or “scoot” the cookie in small circles. The edges will nudge into a perfect round shape. Be sure to do this while the cookies are still hot and pliable, usually within the first 30 seconds of coming out of the oven!
Cool: Let the cookies cool on the baking sheet for ~2-3 minutes, then carefully transfer to a wire rack to cool completely to allow the cheesecake filling to firm up. They’ll become perfectly chewy as they cool. You can sprinkle the tops with a little more cinnamon/sugar if you have extra!