Preheat the oven to 350°F. Spray a 9x13-inch baking dish with cooking spray.
In a small bowl, combine sugar and cinnamon. Set aside.
Bring the flour tortillas to room temperature (or heat for a few seconds in the microwave) so that they are more pliable for folding.
Spoon about ½ cup of apple pie filling in a line down the center of a flour tortilla, leaving room to fold over the edges. Sprinkle 1 teaspoon of cinnamon sugar over the pie filling.
Fold top and bottom edges in toward the center and then roll the tortilla up, folding in the left side and rolling until it forms an enclosed burrito shape.
Continue to fill and roll the remaining tortillas.
Place seam side down in the greased baking dish sprayed with cooking spray.
Mix together the melted butter and ½ cup caramel sauce to combine.
Pour the caramel butter over the enchiladas, using a spoon or spatula to spread the sauce over as much of the tortillas as possible. Sprinkle more cinnamon sugar over the top of the prepared enchiladas.
Let the enchiladas sit for 15 minutes or so to give the tortillas an opportunity to soak up a little bit of the sauce.
Bake for 30 to 35 minutes or until the tortillas are lightly browned and caramelized on top. You can baste the enchiladas halfway through baking with the sauce that has pooled in the bottom of the dish.
Serve warm with an extra drizzle of caramel sauce and vanilla ice cream.