Preheat the oven to 350 degrees.
Follow the instructions for the pie crust and chill for 30 minutes to 1 hour, or use your favorite store bought brand.
Once chilled, place the dough on a lightly floured work surface. Sprinkle the dough and flour your rolling pin, and roll the dough out from the middle to the outer edge, going in about 10 minute intervals clockwise around to form a circle. After every couple of rolls, make sure to lift the dough and sprinkle more flour underneath to prevent sticking. If the dough does stick, scrape any bits of dough from your work surface as it's a magnet for even more sticking.
Roll the dough until it's large enough to hang over the edge of your pie pan by a couple of inches. Once it's large enough, use your rolling pin to gently roll the dough around it, and unroll it right into your pie plate.
Tuck the dough gently into the inside of the pie pan, then use a bench scraper or knife to trim the edges around the top of the pie. It's ok to leave a little extra for crimping, etc. as the top does shrink a bit. From there, crimp your edges as best as you can, or use the scraps to cut out decorative shapes. Chill the crust while you prepare the filling.
Place the pumpkin puree, evaporated milk, brown sugar, eggs, and chai spice in a medium bowl and whisk to combine. Pour into the prepared pie crust and bake for 45-50 minutes or until set (you can insert a knife into the center of the pie to be sure, and if it comes out clean it's done). Cool the pie on a wire rack for at least 1 hour.
Before serving, beat the heavy whipping cream with the granulated sugar until stiff peaks form, being careful not to over whip. Serve the pie with the whipped cream and extra sprinkles of chai spice, if desired, and enjoy!