Prepare the Pastry Dough: Begin by mixing all-purpose flour, powdered sugar, ground cinnamon, and salt in a large bowl. Cut in cold cubed butter until it resembles coarse crumbs, then stir in milk, egg yolks, and vanilla extract until just combined.
Chill the Dough: Form the dough into a disc and wrap it tightly in plastic wrap before refrigerating for at least 20 minutes.
Make the Filling: In a separate bowl, combine pumpkin puree, light brown sugar, ground cinnamon, nutmeg, and cloves until smooth and well-blended.
Roll Out Dough and Fill Pastries: On a lightly floured surface, roll out chilled dough to about 1/8 inch thick and cut into circles. Place a spoonful of pumpkin filling on half of each circle before folding over and sealing edges with a fork.
Bake the Pastries: Preheat your oven to 375°F (190°C). Arrange filled pastries on lined baking sheets and bake for approximately 25 minutes or until golden brown.
Glaze and Serve: While pastries cool slightly, whisk together powdered sugar with milk and vanilla extract until smooth to create a glaze. Drizzle over cooled pastries before serving warm or at room temperature.