Preheat oven to 350℉. Line a cookie sheet with parchment paper and set aside.
Prepare the cookie dough:
Whisk together the flour, pumpkin spice and salt. Set aside. In a large mixing bowl combine the cream cheese, butter and sugars. Beat on medium-high until the mixture is fluffy, about 3 minutes. Scrape down the sides and bottom of the bowl and blend again. Add the egg yolk and vanilla. Blend until incorporated.
Add the flour mixture in 3 additions, scraping down the sides of the bowl as needed. Fold a few times with a spatula to ensure there are no dry pockets left. The mixture will be thick.
Prepare the filling:
Combine all the filling ingredients in a medium bowl. Whisk until blended. Set aside.
Fill and bake the cookies:
Roll the dough into 2 tablespoon balls (36g each) using a medium cookie scoop. Roll each dough ball in coarse sugar to coat. Place on the prepared cookie sheet about 2 inches apart. Continue until the cookie sheet is filled.
Using a 1 tablespoon measuring spoon, press down on the dough balls to create a well in the center of each cookie. Fill each well with 1 tablespoon of the prepared filling.
Bake for 14 to 17 minutes or until the cookies are set and the bottom is light golden brown. Transfer to a wire rack to cool completely.
Repeat with remaining cookie dough ensuring the cookie sheet is cooled before adding the dough balls.
When ready to serve, pipe or dollop whipped cream on top each cookie (optional). Sprinkle with additional pumpkin pie spice or cinnamon and enjoy.