1. Preheat the oven to 350°F.
2. Mix together the half and half and pumpkin puree. Whisk in the eggs, brown sugar, salt, and pumpkin pie spice. Fill a pie plate with the mixture and place in a deeper baking dish. Put hot water in the deep baking dish so that it surrounds the pie plate. Bake for 20-­25 minutes.
3. While baking, fit two plastic piping bags with your choice of frosting tips. Or cut a hole in the corner of a plastic zip-top bag.
4. In a medium bowl, combine the heavy cream with the powdered sugar and mix with an electric mixer on high speed until cream thickens and ripples appear in bowl as you mix.
5. Fill one bag with the whipped cream and set aside in the fridge until ready to use.
6. In a small plastic bag, crush the baked pie crust or shortbread cookies using a rolling pin or your hands.
7. Remove the pumpkin filling from the oven and let cool completely. Once cooled, spoon the custard in the second piping bag.
8. Assemble the trifle. Start with a layer of crust and top the crust with the pumpkin pie filling. Top with the whipped cream and repeat until trifle cups are filled, ending with the whipped cream. Sprinkle cinnamon on top of the whipped cream.
9. Serve immediately or place in the refrigerator until ready to serve.

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