01 -
Preheat oven to 350°F. Line a cookie sheet with parchment paper and set aside.
02 -
Whisk together the flour, pumpkin spice, and salt in a medium bowl. In a large mixing bowl, combine cream cheese, butter, granulated sugar, and brown sugar. Beat on medium-high until fluffy, approximately 3 minutes. Scrape down the sides and bottom of the bowl and blend again. Add the egg yolk and vanilla extract and mix until fully incorporated. Gradually add the flour mixture in 3 additions, scraping the bowl as needed. Fold the dough gently with a spatula to remove any dry pockets. The dough will be thick.
03 -
In a medium bowl, whisk together egg, brown sugar, salt, pumpkin spice, whole milk, pumpkin puree, and vanilla extract until smooth. Set aside.
04 -
Roll the cookie dough into 2-tablespoon balls (36g each) using a cookie scoop. Roll each ball in coarse sugar to coat and place on the prepared cookie sheet 2 inches apart. Using a 1-tablespoon measuring spoon, press down on each dough ball to create a well in the center. Fill each well with 1 tablespoon of the prepared filling.
05 -
Bake in the preheated oven for 14-17 minutes, or until the cookies are set and the bottoms are light golden brown. Transfer the cookies to a wire rack to cool completely.
06 -
Repeat the shaping, filling, and baking process with the remaining cookie dough, ensuring the cookie sheet is cool before placing new dough balls on it.
07 -
Pipe or dollop whipped cream on top of each cookie if desired. Sprinkle with additional pumpkin spice or cinnamon. Serve and enjoy.