Preheat your oven to 350℉ (175℃) and line a baking sheet with parchment paper.

In a medium bowl, whisk together the flour, pumpkin pie spice, and a pinch of salt.

Beat the cream cheese and butter together until light and fluffy, then add the sugars and mix until creamy.

Add the egg yolk and vanilla extract to the mixture and blend thoroughly.

Gradually add the flour mixture to the creamy base in three parts, mixing until just combined.

In a separate bowl, whisk the whole egg, milk, brown sugar, pumpkin puree, pumpkin pie spice, and salt until smooth.

Portion the dough into balls and roll in coarse sugar.

Create a small well in the center of each dough ball.

Fill the wells with the filling mixture.

Bake for 14–17 minutes until edges are set but centers remain soft.

Cool on a wire rack before serving.