Begin by preheating your oven to 350 degrees F.
Line a 9-in pie plate with one pie crust. Trim and crimp edges. Place on a baking sheet and set aside.
Next, prepare the cinnamon roll crust topping. Take your second 14-inch pie dough and brush it with the melted butter. In a small bowl, mix together the cinnamon and sugar. Sprinkle the cinnamon-sugar mixture over the pastry. Pat it in lightly with your fingers.
Roll-up the pasty into a cylinder. Press the seam to seal. Cover and chill until needed.
In a large bowl, whisk together the sugar, cornstarch, spices, and salt. Beat in the squash puree, butter, eggs, milk, and vanilla until smooth. Pour into the crust.
Cover the edges of the crust loosely with foil or a pie crust guard. Bake for 25 minutes.
While the pie bakes, cut the chilled cinnamon roll pie crust cylinder into 1/4-inch slices. Remove the pie from the oven and take off the foil. Carefully arrange the cinnamon roll slices** on top of the filling. They should be close together but not touching. Return the pie to the oven and continue baking for another 30-35 minutes or until the filling is puffed and set and the cinnamon roll circles are lightly browned.
Cool on a wire rack for one hour. Then transfer to the refrigerator to finish cooling.
Slice and serve with freshly whipped cream.