Preheat oven to 350°F (175°C) and prepare muffin tin with liners and cooking spray.

Whisk together flour, pumpkin pie spice, baking powder, and salt in a large bowl.

In a separate bowl, whisk pumpkin puree, sugar, melted butter, eggs, milk, and vanilla extract.

Gently fold the wet ingredients into the dry ingredients until just combined.

Fill cupcake liners about 2/3 full.

Bake for 24-28 minutes, or until a toothpick inserted into the center comes out clean.

Let cool in the pan for a few minutes before transferring to a wire rack to cool completely.

While cupcakes cool, cut out shapes from pie crust.

Place pie crust cutouts on a parchment-lined baking sheet, brush with milk, and sprinkle with sugar.

Bake pie crust cutouts for 10-15 minutes, or until golden brown.

Let pie crust cutouts cool completely.

For the filling/topping, beat cream cheese and confectioners' sugar until smooth.

Add 1 cup of heavy cream and beat until soft peaks form.

Add remaining 1 cup of heavy cream and beat until stiff peaks form.

Transfer the filling/topping to a pastry bag fitted with a round tip.

Remove a small scoop from the top center of each cupcake.

Fill the hole with some of the filling/topping and replace the cupcake piece.

Pipe a swirl of filling/topping on top of each cupcake.

Gently push a pie crust cutout into the frosting of each cupcake.

Serve and enjoy!