In a large mixing bowl, cream together ½ cup of unsalted butter, ½ cup brown sugar, and ½ cup granulated sugar until pale and fluffy, approximately 3-4 minutes.

Blend in 1 cup of pumpkin puree, 1 large egg, and 1 teaspoon of vanilla extract to the creamed mixture, mixing on low speed until fully incorporated, about 1-2 minutes.

In a separate bowl, whisk together 2 cups of all-purpose flour, 1 teaspoon of baking soda, 1 teaspoon of baking powder, ½ teaspoon of salt, 2 teaspoons of pumpkin pie spice, and ½ teaspoon of cinnamon.

Gradually fold the dry mixture into the wet ingredients until a dense but soft dough forms; avoid over-mixing.

Cover the bowl with plastic wrap and refrigerate the dough for at least 1 hour to prevent spreading.

In another bowl, beat 8 ounces of softened cream cheese with ¼ cup sugar, 1 teaspoon vanilla extract, and 1 tablespoon all-purpose flour until smooth and creamy; refrigerate until needed.

Preheat your oven to 350°F (175°C). Scoop tablespoons of dough and roll them into balls, then flatten each slightly to make a dip in the center.

Arrange cookie dough on a parchment-lined baking sheet, spacing them about 2 inches apart. Bake for 10-12 minutes until edges are set and centers slightly soft.

Cool cookies on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.

Pipe the chilled cheesecake filling into the center of each cooled cookie, filling the dip generously.

Refrigerate filled cookies for about 15-30 minutes to set the cheesecake filling.