Preheat oven to 350°F. Line a large baking sheet with parchment paper.
Arrange crescent roll triangles in a circle with wide ends overlapping in the center.
Spoon apple pie filling in a ring around the base. Drizzle with caramel sauce.
In a bowl, beat cream cheese, sugar, and vanilla until smooth. Dollop over apple layer.
Fold the dough tips over the filling and tuck underneath the base of the ring.
Bake for 20–22 minutes or until golden. Cool slightly.
Whisk powdered sugar and milk to make icing. Drizzle over cooled ring and serve.