01 -
Preheat oven to 350°F. Line a cookie sheet with parchment paper and set aside.
02 -
Whisk together all-purpose flour, pumpkin spice, and salt in a medium bowl. Set aside.
03 -
In a large mixing bowl, combine cream cheese, unsalted butter, granulated sugar, and brown sugar. Beat on medium-high speed until light and fluffy, about 3 minutes. Scrape down the sides and bottom of the bowl and mix again.
04 -
Add egg yolk and vanilla extract to the creamed mixture. Blend until fully incorporated.
05 -
Add the flour mixture to the wet ingredients in three additions, scraping down the bowl as needed. Fold with a spatula to ensure no dry spots remain. The dough should be thick.
06 -
In a medium bowl, whisk together egg, brown sugar, salt, pumpkin spice, whole milk, pumpkin puree, and vanilla extract until blended. Set aside.
07 -
Roll dough into 2-tablespoon portions and coat each ball in coarse sugar. Place on the lined cookie sheet about 2 inches apart. Using a 1-tablespoon measuring spoon, press an indentation in the center of each ball. Fill each well with 1 tablespoon of the prepared pumpkin filling.
08 -
Bake for 14 to 17 minutes or until the cookies are set and bottoms are lightly golden. Transfer to a wire rack and allow to cool completely before serving.
09 -
Repeat shaping, filling, and baking with the remaining dough, ensuring the cookie sheet is cool before adding more dough balls.
10 -
Top cooled cookies with a dollop or piping of whipped cream if desired. Finish with a sprinkle of pumpkin pie spice or cinnamon before serving.