Preheat the oven to 350°F and line a baking sheet with parchment paper.
In a mixing bowl, beat the softened butter and granulated sugar until light and creamy.
Stir in the pumpkin puree, cinnamon, and vanilla extract until fully combined.
Add the flour and mix until a soft dough forms.
Scoop the dough into 12 small balls and place them on the prepared baking sheet. Use your thumb or the back of a teaspoon to press a small well into the center of each ball.
In a separate bowl, mix the cream cheese and powdered sugar until smooth.
Spoon a small amount of the cream cheese mixture into each well.
Bake for 12 to 14 minutes until the edges are lightly golden. Let the cookies cool on the baking sheet for 5 minutes before moving them to a wire rack.