Cheesecake Filling: Prepare a small baking sheet with parchment paper. Set aside.
In a small mixing bowl beat to combine the cream cheese, granulated sugar, and vanilla extract, until smooth. (You can do this by hand or quicker with a hand mixer.)
Scoop the cheesecake mixture into 2 teaspoon sized dollops and place on the prepared baking sheet. (about 9 dollops)
Place in the freezer for about 20 minutes or until frozen and firm.
Pumpkin Cookies: In a medium mixing bowl, combine the flour, pumpkin pie spice, baking soda, and salt with a whisk. Set aside.
In a large mixing bowl, beat to combine the melted butter and brown sugar until smooth. Add the egg yolk, vanilla extract, and pumpkin puree, mixing until well combined.
Add the dry ingredients and fold in with a large spoon until completely combined. Use a large (2 oz) cookie scoop to create 9 cookie dough balls.
Flatten each cookie dough ball, and place the frozen cheesecake filling in the center. Fold the dough over the filling and roll into a smooth ball.
In a small bowl, combine the spiced sugar ingredients. Roll each cookie dough ball in the cinnamon sugar.
Transfer to the prepared baking sheets and bake for 11-12 minutes, until edges look set. Remove from oven and let cool on the baking sheet for 10 minutes, then transfer to a cooling rack to cool completely.
Storage: Refrigerate the cooled cookies in airtight containers or bags for up to 7 days. Don’t leave them at room temperature because the cheesecake filling will spoil.Warm: For a freshly-baked feel, microwave the chilled cookies for about 10 seconds. If you prefer them room temperature, leave them out for 5 to 10 minutes before digging in.Freeze: Wrap each cooled cookie in plastic wrap. Transfer them to a freezer-friendly bag or container and freeze for up to 3 months. Thaw them on the counter for 30 minutes, or until the filling softensDIY Pumpkin Pie Spice: Combine 4 tsp cinnamon, 2 tsp ginger, 1 tsp cloves, 1/2 tsp nutmeg and 1/2 tsp allspice.Filling: You must freeze the cream cheese mixture before stuffing and baking the cookies. If you don’t, it will be almost impossible to wrap the dough around the cheesecake filling. Also, unfrozen filling can melt out of the cookies as they bake.Leave Space: Don’t crowd the cookies on a small baking sheet. You will need to leave about 4 inches in between each cookie so they have space to spread out as they bake.Let Them Cool: Allow the cookies to cool on the baking sheet for at least 15 to 20 minutes before removing them. This is very important, otherwise the cheesecake filling will not set properly.Room Temperature: Cream cheese needs to be fully softened and at room temperature. If it is still cold, it will make a lumpy cheesecake filling.