Prepare the Cheesecake Filling:
Mix cream cheese, sugar, and vanilla extract with an electric mixer on medium-high until smooth and fluffy (about 2 minutes).
Scoop into 16 small portions (about 2 tsp each), place on parchment-lined sheet, and freeze for at least 30 minutes.
Remove Moisture from the Pumpkin:
Spread pumpkin puree on a plate, cover with paper towels, and press lightly. Repeat at least 4 times until reduced to just under ¼ cup.
Make the Cookie Dough:
Whisk together flour, pumpkin pie spice, baking powder, baking soda, and salt.
Cream butter and brown sugar until fluffy (2 minutes).
Add egg yolks and vanilla; mix until pale and fluffy (1 minute).
Mix in dried pumpkin puree.
Gradually add dry ingredients and mix on low until dough forms.
Assemble the Cookies:
Scoop dough into 16 portions (about 2 tbsp each), roll into balls, and flatten slightly.
Place frozen cheesecake ball in the center of each.
Fold dough around the filling and roll into smooth balls.
Coat in Spiced Sugar:
Mix sugar and pumpkin pie spice. Roll each dough ball in the mixture to coat evenly.
Bake the Cookies:
Preheat oven to 350°F (175°C). Line baking sheets with parchment.
Place 6 cookies per sheet.
Bake for 12–13 minutes until edges are set and tops are slightly firm.
Cool on baking sheet for 10 minutes, then transfer to wire rack.