In a medium bowl, blend the cream cheese until it reaches a smooth and creamy consistency.
Incorporate ¼ cup of granulated sugar and ½ teaspoon of vanilla extract.
Line a baking pan with parchment paper. Using a scoop, take about 1-2 tablespoons of the cheesecake mixture and place it onto the parchment. Continue this process until all the cream cheese mixture is used.
Pop the baking pan in the freezer to chill while you finish making the cookies.
In a spacious mixing bowl, combine the flour, baking soda, baking powder, 2 teaspoons of pumpkin pie spice, and salt. Whisk everything together until well blended, then set aside.
In a separate large bowl, cream together the butter, light brown sugar, and ¼ cup of granulated sugar for approximately 1 minute. Then, add the egg yolk, 1 teaspoon of vanilla extract, and pumpkin puree, mixing until well combined.
Gradually incorporate the dry ingredients into the wet mixture, stirring gently until just combined.
Preheat your oven and line two cookie sheets with parchment paper; set them aside. Next, scoop the cookie dough into 12 evenly sized balls and arrange them on one of the prepared sheets.
Transfer the cookies to the refrigerator and allow them to chill for 30 minutes.
Preheat your oven to 350 degrees Fahrenheit.
In a shallow saucer, combine ¼ cup of sugar with ½ teaspoon of pumpkin pie spice and mix well.
Remove the cookies from the refrigerator and the cheesecake drops from the freezer.
Remove the cookies from the refrigerator and the cheesecake bites from the freezer. Take each ball of cookie dough and press a cheesecake bite into the center, carefully wrapping the dough around it.
Gently roll the dough ball in the sugar and pumpkin pie spice mixture until fully coated. Place the cookies back onto the parchment paper, arranging six cookies per tray. Before baking, flatten each cookie slightly for even cooking.
Bake for 16 to 19 minutes. Once done, let the cookies cool for a few moments on the baking sheets before transferring them to cooling racks to cool completely.