How to Make It
Make the Dough: Combine flour, sugar, and salt in a bowl. Using a pastry cutter or your hands, cut in butter and shortening. Add water and mix with your hands to hydrate the flour. Do not knead the dough, but fold it over itself and press it until the water is completely absorbed. Shape dough into a disc, wrap in plastic wrap, and refrigerate for 1 hour.
Make the Filling: In a small bowl, whisk together cornstarch with 3 Tbsp. water until completely dissolved. Pour into a large pot. Add the rest of the ingredients and stir to combine. Heat over medium, stirring constantly, until sugar is dissolved and mixture has thickened and is bubbling. Remove from heat. Discard cinnamon sticks and star anise.
Preheat oven to 350°F. Remove dough from refrigerator. Cut dough in half and shape into 2 discs. On a lightly floured surface, roll one disc of dough into an 1/8-inch thick circle. Transfer to a deep 9 1/2-inch pie plate, pressing in to the pan and trimming off any excess dough. Pour Pineapple Filling into pie plate. Roll remaining disc of dough into an 1/8-inch thick circle and place on top of pie filling. Remove excess dough and press edges of dough together around the perimeter of the pie. Crimp the edge and cut a few slits in the surface of the pie. Whisk together egg and water; brush surface of pie with egg wash. Bake for 50 to 60 minutes, rotating halfway through baking. Allow to cool completely before slicing and garnishing with whipped cream and ground cinnamon.
The homemade pie dough can easily be replaced with two store-bought pie crusts.