Preheat oven to 350°F. Unroll pie crust on lightly floured surface. Brush with butter and sprinkle evenly with cinnamon. Roll up tightly and slice into 1/2-inch rounds, like miniature cinnamon rolls. Then press evenly into bottom and sides of 9-inch pie plate, making sure there are no spaces between the rolls.
Pour 2 cans of apple pie filling on top of the crust. Place pie on a sheet pan and cover top loosely with foil. Bake for 25 minutes. Meanwhile, combine butter, flour and brown sugar in a large bowl and form into crumbles using a pastry cutter. Sprinkle crumbles over apple filling.
Bake until top and crust are golden brown and filling is bubbling, an additional 25–35 minutes (cover top/crust with foil if necessary near the end). Remove from oven and cool.
Whisk together powdered sugar, vanilla, cinnamon, and milk in small bowl to form icing (add more sugar or milk to reach desired consistency). Drizzle over cooled pie.
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Notes
Storage: To store leftovers, cover the pie tightly with plastic wrap or foil and keep it in the fridge for up to 3 days. For longer storage, freeze it for up to 3 months. Reheat in the oven for best results.