Preheat oven to 350F and line a baking sheet with parchment paper.
Beat butter and 1 1/2 cup of the sugar together in a large mixing bowl.
Add in egg, vanilla, and pumpkin and mix until combined.
Stir in flour, baking powder, salt, and cinnamon and mix until combined.
Place in the fridge for at least 30 minutes.
In a separate bowl, beat cream cheese until fluffy then stir in sugar and vanilla and mix until smooth.
Roll chilled dough into 1in. balls and roll in 1/4 cup of sugar.
Move to prepared pan and bake until lightly golden; about 15 minutes.
Remove from oven and press middle of cookie with the back of a 1/2 Tbsp. measuring spoon. Once cool, add cheesecake filling to the center.
Stir together sugar and cinnamon & Sprinkle over cookies and serve.
ENJOY!