Preheat oven to 350℉. Line a large baking sheet with parchment paper. Set aside.
Place pumpkin puree onto a paper towel to absorb excess moisture. Set aside.
Whisk flour, soda, pumpkin pie spice, and salt in a medium mixing bowl. Set aside.
In a large bowl, beat softened butter and sugars with an electric mixer until light and fluffy, about 2 minutes.
Add in the pumpkin puree.
With the mixer on low, add dry ingredients and mix until combined. Set aside.
In a medium mixing bowl, combine cream cheese, powdered sugar, and vanilla extract until smooth.
In a small bowl, combine ¼ cup granulated sugar and ground cinnamon.
Using a 2 Tablespoon cookie scoop, form dough into balls and drop them into the cinnamon sugar mixture. Roll to coat.
Place the cookie balls on the lined baking sheet, spacing them about 2 inches apart.
Make an indentation in the center of each cookie ball using the back of a large measuring spoon. Spoon about 1 Tablespoon of cheesecake mixture into the indentation.
Bake for 13-15 minutes or until edges are set.
Allow cookies to cool on the baking sheet for 10 minutes. Move to a wire cooling rack to finish cooling.