1. Make the Cheesecake Filling:

• Line a small baking sheet or plate with parchment paper.
• In a small bowl, beat together the cold cream cheese, granulated sugar, and vanilla extract using an electric mixer (hand mixer or stand mixer) on medium-high speed until the mixture is completely smooth, creamy, and fluffy (about 2 minutes). Scrape down the sides of the bowl as needed.
• Using a teaspoon or a small cookie scoop, scoop out 16 portions (about 2 teaspoons each) of the cheesecake filling. Place them onto the prepared baking sheet.
• Freeze the cheesecake balls until solid and very firm. Keep them in the freezer until you are ready to assemble the cookies.

2. Make the Spiced Sugar:

• In a small bowl, whisk together the granulated sugar and pumpkin pie spice until well combined. Set aside.

3. Make the Pumpkin Cookie Dough:

• Preheat Oven and Prepare Baking Sheets: Preheat your oven to 350°F (175°C). Line two large baking sheets with parchment paper.
• Dry the Pumpkin Puree (Crucial Step): This step is essential for achieving the correct cookie texture. Spread the 1/2 cup of pumpkin puree in a thin layer on a plate. Place several layers of paper towels on top of the puree and press gently to absorb excess moisture. Scrape the pumpkin into a pile, spread it out again, and repeat the process with fresh paper towels. Continue this process 4-5 times, or until very little liquid is absorbed by the paper towels. The pumpkin puree should be noticeably drier and almost paste-like. You should have slightly less than 1/4 cup of dried puree after this process.
• Combine Dry Ingredients: In a medium bowl, whisk together the all-purpose flour, pumpkin pie spice, baking powder, baking soda, and salt until well combined. Set aside.
• Cream Butter and Sugar: In a large bowl, using an electric mixer (hand mixer or stand mixer), cream together the softened butter and brown sugar on high speed until light and fluffy (about 2 minutes).
• Add Egg Yolks and Vanilla: Add the egg yolks and vanilla extract to the creamed butter and sugar. Beat on medium speed until well combined and the mixture is pale and fluffy (about 1 minute).
• Add Dried Pumpkin Puree: Add the dried pumpkin puree to the wet ingredients. Beat on medium speed until well combined.
• Combine Wet and Dry Ingredients: Gradually add the dry ingredients to the wet ingredients, mixing on low speed until just combined. Do not overmix.

4. Assemble and Bake the Cookies:

• Scoop Dough: Using a 2-tablespoon cookie scoop (or a spoon), scoop out 16 portions of the pumpkin cookie dough.
• Flatten and Fill: Roll each portion of dough into a ball. Then, flatten the ball into a disc (about 1/4-inch thick).
• Add Cheesecake Filling: Remove the frozen cheesecake balls from the freezer one at a time as you work. Place one frozen cheesecake ball in the center of each flattened cookie dough disc.
• Enclose Filling: Carefully wrap the cookie dough around the frozen cheesecake filling, pinching the edges to seal completely. Ensure the cheesecake is fully enclosed by the dough. Roll the assembled cookie into a ball again.
• Roll in Spiced Sugar: Roll each filled cookie dough ball in the prepared pumpkin spice sugar mixture until evenly coated.
• Arrange on Baking Sheet: Place the coated cookie dough balls on the prepared baking sheets, leaving about 3 inches of space between each cookie. Bake only 6 cookies per sheet to allow for even spreading and airflow.
• Bake: Bake one sheet at a time for 12-13 minutes, or until the edges are lightly golden brown and the centers are set but still slightly soft.
• Cool: Let the cookies cool on the baking sheet for 10 minutes before transferring them to a wire rack to cool completely.