Special equipment: Your favorite small holiday cookie cutter A pastry bag fitted with a round pastry tip
For the cupcakes: Position an oven rack in the center of the oven, and preheat to 350 degrees F. Line a 12-cup muffin tin with paper liners, and coat the liners and the top of the tin with cooking spray.
Whisk the flour, pumpkin pie spice, baking powder and salt together in a large bowl. Whisk the pumpkin puree, granulated sugar, butter, eggs, milk and vanilla together in a medium bowl. Pour the pumpkin mixture into the flour mixture, and gently fold until just incorporated (it's OK if there are some lumps).
Bake until the tops spring back when pressed, 24 to 28 minutes, rotating the tin halfway through. Let the muffins cool in the pan for a few minutes, then transfer to a rack to cool completely. (The cupcakes can be made up to 2 days before and refrigerated in an airtight container.)
For the pie crust cutouts: While the muffins are cooling, cut out 12 shapes from the pie crust, and arrange them on a parchment-lined baking sheet. Brush each with milk, and sprinkle generously with granulated sugar. Bake until deep golden brown, 10 to 15 minutes, rotating the baking sheet halfway through. Let cool completely.
For the filling/topping: Beat the cream cheese and confectioners' sugar together in a medium bowl until smooth. Add 1 cup of the cream, and beat until soft peaks form. Add the remaining 1 cup cream, and beat until stiff peaks form. Transfer the mixture to the prepared pastry bag.
To fill and top the cupcakes: Use a teaspoon or a melon baller to take a small scoop out of the top center of each cupcake (save these cupcake pieces). Squeeze some of the filling/topping into each hole, and top with one of the cupcake pieces. Pipe a swirl of the filling/topping on top of each cupcake. (The cupcakes can be refrigerated for up to 2 hours at this point if you prefer them chilled.) Gently push a pie crust cutout into the frosting of each cupcake, and serve.
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