In a small bowl mix together cream cheese, sugar and vanilla until smooth. Scoop into 2 teaspoon size balls, this should make 11 balls. Place on a plate and put into the freezer until completely frozen, about 30 minutes.
Preheat oven to 350 F. Line two baking sheets with parchment paper.
Measure out ⅓ cup of pumpkin and place on a paper plate. Using some paper towels, blot the pumpkin, removing liquid until the paper towel wipes clean. When done the pumpkin should measure more like ¼ cup (60g).
Place butter and sugars in the bowl of a stand mixer, fitted with a paddle attachment and mix together. Add pumpkin, egg yolk and vanilla and mix again.
In a separate bowl, whisk together flour, baking soda, salt, pumpkin pie spice and cinnamon. Add flour mixture to bowl and mix on low, being careful not to overmix. I usually like to stop mixing when I still have flour remnants around the bowl.
In a small bowl mix together sugar, cinnamon and pumpkin pie spice.
Scoop the dough into large balls, I like to use a 3 tablespoon cookie scoop. Take the frozen cheesecake balls out of the freezer. Push cheesecake balls into the cookie dough, making sure to completely cover the cheesecake. Roll the cookie ball in the sugar mixture. Place 5-6 cookies on a baking sheet.
Bake the cookies for 12-14 minutes. You don't want to see any shiny dough in the middle of the cookie, and make sure they have a golden rim around the outside. You need to make sure you bake these cookies all the way, so the cheesecake isn't gooey. Sprinkle cookies with extra sugar mixture when they come out of the oven. Allow to cool completely before eating.