Preheat oven to 400°F. Line a cookie sheet with parchment paper or a silicone baking mat.
Mix granulated sugar and 1 teaspoon cinnamon in a small bowl. Unroll pie crust and sprinkle with the cinnamon sugar. Press lightly with your hands to seal it to the crust. Spray the crust lightly with cooking spray.
Bake crust for 8-12 minutes, until light golden brown around the edges. Let cool completely before making ice cream.
Place cream cheese and sweetened condensed milk in a large bowl and mix with a hand mixer until smooth. You can do this by hand, but I find that using a hand mixer makes it easier to get out the lumps. Mix in vanilla and 1 teaspoon cinnamon. Fold in Cool Whip (see note).
Crumble cooled pie crust into small pieces and stir into ice cream mixture. I reserved about 1/4 of the crust for topping, but you can add it all if you wish.
Place ice cream in a large resealable container and freeze for at least 4 hours but overnight is better. Will keep in the freezer for up to one month.