Preheat the oven to 350°F. Line a cookie sheet with parchment or a silpat liner.
Melt the butter in a small skillet over low-medium heat. Add apples, cinnamon and sugar. Cook, stirring occasionally, until the apples are just beginning to turn translucent, about 15 minutes. Cool at least 10 minutes.
Unroll crescent rolls on a cutting board, leaving them in the rectangle as much as possible. Press the seams together to form one big rectangle. Spread apples over the crescent rolls. Roll up as tight as possible, slice into 8 equal portions. (It’s best to use a serrated knife to cut them.) Place on baking sheet. You can evenly space them (not touching) or you can place them close together so they bake together, creating a more doughy center (like traditional cinnamon rolls).
Bake until golden on the top, 15-25 minutes, or until cooked through.
While they are baking, make the frosting. Melt butter and brown sugar together and cook for 2 minutes, stirring constantly. Remove from heat and whisk in powdered sugar, then whisk in vanilla and 2 tablespoons cream. Add more cream as needed for desired consistency.
Tip: you can skip making the frosting and serve caramel ice cream topping instead.