First, make the cheesecake filling. Line a smaller baking sheet with parchment paper.
Add the cream cheese, sugar, and vanilla to a small bowl. Mix together on high speed until fluffy. Scoop the filling onto the lined baking sheet into 18, 1.5 tsp portions. (They don't need to look pretty.) Freeze them for about 30 minutes or until hardened.
Preheat the oven to 350. Line a larger baking sheet with parchment paper.
Add the pumpkin puree to a large bowl. It is important to remove some of the liquid from the cookies so they don't fall apart. To do this, lightly press down on the pumpkin in the bowl with paper towels a few times.
To the same bowl with the pumpkin, add the softened butter, brown sugar, and granulated sugar. Cream together using a hand or stand mixer. Add in the eggs and vanilla and continue to mix on high speed until fluffy.
To a separate medium bowl, add the gluten free flour, pumpkin pie spice, baking powder, and baking soda. Mix to combine.
Add the dry ingredients to the wet ingredients and mix on low speed until just combined. Do not over-mix. Place the bowl of dough into the fridge to chill for 20-30 minutes.
Combine the sugar coating ingredients on a plate and stir.
Use a 2 tbsp cookie scoop to scoop the dough into 6 balls (we are making 6 at a time, ultimately having 18 total). Place the dough and cream cheese filling back into the fridge and freezer while you work on the first batch.
Flatten the balls, then place one of the frozen cheesecake filling pieces into the center of each one. Use your hands to wrap the dough around the filling and roll it into a ball again. You shouldn't be able to see any cream cheese. Roll each ball into the sugar / cinnamon mixture to coat.
Place the 6 cookies onto the lined baking sheet and press down slightly using a spatula or your hand. Bake for 13-15 minutes. Let them cool for 10 minutes on the baking sheet, then transfer to a wire cooling rack to cool completely. Repeat 2 more times until you have 18 cookies total.
Enjoy! Keep the cookies stored in the refrigerator.