Preheat oven to 350°F. Prepare an 8x8-inch square baking pan with nonstick baking spray. For easy removal, you can line the pan with aluminum foil and then spray the foil with a non-stick baking spray.
In a large bowl, using a hand mixer, beat the cream cheese, egg, vanilla, and sweetened condensed milk until smooth and creamy, about 3 minutes. Fold in the cinnamon chips with a spatula. Set aside.
8 ounces cream cheese, 1 large egg, 1 teaspoon pure vanilla extract, ⅓ cup sweetened condensed milk, 1 cup cinnamon baking chips
Cut the cookie dough tube in half. With lightly flour-dusted fingers (or you can just dampen them with water), spread half of the cookie dough into the bottom of the prepared pan. Pour the cheesecake mixture on top of the bottom layer and spread it to the edges. Set aside.
16.5 ounces pre-made sugar cookie dough
In a small bowl, mix the cinnamon and sugar together. Using the remaining cookie dough, scoop 1-teaspoon-sized balls, roll them around in the cinnamon sugar, press flat, and lay them on top of the cheesecake mixture. Do this with all the dough until the entire top is covered. Once done, sprinkle a good amount of the remaining cinnamon sugar all over the top of the cookie pieces.
3 tablespoons granulated sugar, ½ teaspoon ground cinnamon
Bake for 35-40 minutes, until the top has turned a light golden brown color. This took me 37 minutes.
Cool for about an hour, then transfer into the refrigerator to chill for at least another hour before cutting.