Preheat the oven to 425°F (220°C).
Unroll one round of pie dough and carefully fit it into a pie plate. Shape or flute the rim decoratively.
Cut at least 35 small leaf shapes from the second sheet of pie dough using decorative pastry cutters.
Combine the granulated sugar with the ground cinnamon in a small bowl until evenly blended.
In a separate bowl, whisk the egg together with 1 tablespoon of water to create an egg wash.
Lightly brush the pastry leaves with the egg wash, then dust their surfaces with the cinnamon-sugar mixture.
Brush a small amount of egg wash onto the reverse side of each leaf and arrange the leaves decoratively around the perimeter of the pie shell.
Position small balls of aluminum foil underneath selected leaves to support them, creating dimension while helping prevent the pastry decorations from drooping during baking.
Prick the bottom of the pastry shell several times with a fork. Transfer the prepared crust to the freezer while the pumpkin filling is made.
Place the pumpkin purée, pumpkin spice, finely grated orange zest, and salt in a large microwave-safe bowl and stir to combine.
Microwave the pumpkin mixture for 1 minute. This brief heating period helps integrate the spices and lessen the characteristic canned flavor of the purée. Allow the mixture to cool afterward.
Whisk the sweetened condensed milk and 2 eggs into the cooled pumpkin mixture until the filling is completely combined and smooth.
Pour the prepared pumpkin filling into the chilled pastry shell.
Allow the filled pie to stand briefly so that trapped air bubbles can rise to the surface, helping produce a smoother finished top.
Place the filled pie in the preheated 425°F (220°C) oven and bake for 15 minutes.
Reduce the oven temperature to 350°F (175°C) and continue baking for an additional 35–40 minutes. The filling should appear set around the edges while retaining a slight jiggle at the center.
If the cinnamon-sugar pastry leaves become overly browned, loosely protect the crust with aluminum foil or a silicone pie shield during approximately the final 10 minutes of baking.
Remove the pie from the oven and leave it at room temperature for about 20 minutes.
Transfer the cooled pie to the refrigerator and chill for a minimum of 2 hours.
Preheat the oven to 400°F (200°C). Line a baking sheet with parchment paper or a silicone baking mat.
Distribute the 1/2 cup granulated sugar across the prepared baking sheet in a thin, uniform layer.
Bake for 12–15 minutes, or until the sugar has melted and developed a pale golden caramel color. Monitor it particularly closely after the 12-minute mark to prevent scorching.
Let the caramelized sugar cool completely until firm and brittle.
Break the hardened caramel into smaller shards, then process them in a food processor until finely ground.
Pour the cold heavy cream into a chilled mixing bowl and whisk until the cream begins to gain body.
Add the powdered sugar and continue whisking until soft peaks develop.
Gently fold in the vanilla bean paste and bourbon, mixing only until they are evenly incorporated.
Immediately before serving, scatter a thin and consistent coating of the finely ground caramelized sugar over the surface of the thoroughly chilled pumpkin pie.
Use a kitchen torch to melt and caramelize the sugar until a crisp brûléed layer forms. Alternatively, place the pie beneath the broiler until the topping has melted and caramelized.
When using the broiler, shield the pastry edges with aluminum foil to reduce the risk of scorching.
Before slicing completely through the pie, lightly score or pre-cut the hardened brûlée surface. This helps minimize uncontrolled cracking of the caramel layer.
Serve each portion with a generous spoonful of bourbon-vanilla whipped cream.
Finish the individual slices with freshly grated nutmeg, a small amount of additional orange zest, and fresh mint leaves.
Serve immediately so the cool, creamy pumpkin filling can be enjoyed against the freshly caramelized, crisp sugar topping.