Preheat your oven to 375°. In a medium bowl, whisk together the pureed pumpkin and softened cream cheese until smooth.
Add powdered sugar, pumpkin pie spice, and vanilla and whisk until smooth. Refridgerate while you make the cookies.
Make the cookies. Add the melted coconut oil to a large mixing bowl, then whisk the organic cane sugar and vanilla extract in.
Add the egg and whisk until combined.
Stir in the whole wheat pastry flour, pumpkin pie spice, cream of tartar, and baking soda until well combined.
Roll dough into 24 balls (about 1 tbsp dough each) and then roll in cinnamon sugar until well coated (if using). Place on a parchment-lined sheet pan and flatten with your hand.
Bake in the preheated oven for 6-8 minutes, until the tops begin to crack and the bottoms are slightly golden brown. Allow to cool completely.
Assemble pumpkin pie cookies by dropping about 2 tsp of the pumpkin pie filling onto the bottom of one cookie, then pressing the bottom of another cookie onto the pumpkin filling, creating a cookie sandwich.
Store in the fridge in an airtight container for up to 3 days.