Line a small cookie sheet with parchment paper. In a small bowl, mix cream cheese, sugar, and vanilla on medium-high speed until fluffy, about 2 minutes.

Scoop the cheesecake filling into 16, 2 tsp portions onto the baking sheet and freeze until firm.

In a small bowl, whisk together granulated sugar and pumpkin pie spice for the spiced sugar and set aside.

Preheat the oven to 350 degrees F and line two baking sheets with parchment paper. Dry the pumpkin to remove excess moisture.

In a medium bowl, whisk together flour, pumpkin pie spice, baking powder, baking soda, and salt, then set aside.

In a large bowl, cream softened butter and brown sugar together until fluffy, about 2 minutes with an electric mixer on high speed.

Add egg yolks and vanilla to the butter mixture and mix on medium speed until pale and fluffy, about 1 minute.

Add in the dried pumpkin and combine on medium speed, then add in the dry ingredients and mix on low speed.

Scoop the dough into 16 portions, roll into balls, and flatten each slightly. Place a frozen cheesecake ball in the center and cover with cookie dough, rolling into a ball again.

Roll dough balls in spiced sugar and transfer to the prepared baking sheet. Bake 6 cookies at a time for 12-13 minutes.

Let the cookies cool on the sheet for 10 minutes, then transfer to a wire rack to cool completely.