In a medium mixing bowl, add the butter and both sugars. Stir until well combined.
Add the puréed pumpkin and vanilla to the sugar mixture. Stir until well incorporated and set aside.
In a large mixing bowl, add the flour, salt, baking powder, baking soda, cinnamon and pumpkin pie spice. Stir to mix. Add the pumpkin sugar mixture and stir again to fully incorporate.
Fold in the cinnamon chips.
Cover and chill for 30-40 minutes.
Preheat oven to 350°. Line a large baking sheet with parchment paper and set aside.
Shape the chilled dough into 2 inch balls and place on baking sheet. Using the bottom of a glass, flatten each cookie ball.
Sprinkle the cinnamon sugar mixture on top of each cookie.
Bake for 8-10 minutes. Do not over bake.
While still warm on the baking sheet, lightly sprinkle cookies again with cinnamon sugar mixture.
Allow cookies to cool on baking sheet for 10 minutes before transferring them to a wire rack.