To make the cheesecake filling-

In a medium bowl using an electric mixer beat softened cream cheese until smooth and fluffy.

Add 1/4 cup granulated sugar and ½ tsp. vanilla extract. Continue mixing until the cream cheese filling is well blended and smooth.

Line a baking sheet with parchment paper.

Using a spoon or cookie scoop scoop cheesecake mixture, about 1-2 tbsp at a time and place onto the parchment.

Place the baking pan to the freezer to chill while you make the cookie dough.

To make the pumpkin cookie dough –

In a large mixing bowl, whisk together flour, baking soda, baking powder, 2 tsp. Pumpkin pie spice, and salt. Set aside.

In another large bowl using an electric mixer or in the bowl of a stand mixer, cream together butter, light brown sugar, and ¼ cup granulated sugar, for about 1 minute. Add egg yolk, 1 tsp. vanilla extract, and pumpkin puree. Mix until all of the ingredients are well blended.

Slowly add the dry ingredients to the wet, mixing until just combined.

Line two cookie sheets with parchment paper, and set aside.

Scoop the cookie dough into 12 cookie dough balls, and place onto one of the parchment lined pans.

Place the cookies to the refrigerator to chill for 30 minutes.

Preheat your oven to 350 degrees Fahrenheit.

Place ¼ cup sugar and ½ tsp pumpkin pie spice in a small bowl or shallow dish and mix together.

Remove the cookies from the refrigerator and the frozen cheesecake drops from the freezer.

Take each ball of cookie dough, and press one of the cheesecake balls into the center, wrapping the dough around the filling and pressing it closed.

Drop the dough ball into the pumpkin spice sugar mixture and roll to coat. Return the cookies to the parchment paper, with 6 cookies per tray.

Flatten the cookies slightly before baking.

Bake the cookies for 16-19 minutes. Let the cookies cool slightly on the baking sheets, then move a wire rack to cool completely.