Preheat oven to 375°F or according to crescent roll directions. Line a sheet pan with parchment paper.
Roll out crescent rolls and separate into individual triangles.
Toss asparagus in olive oil and season with salt and pepper.
Fold slice of prosciutto in half and lay on wide side of crescent roll, then fold overlapping part over for flush alignment. Follow with 3-4 stalks of asparagus (depending on size) and 1-2 tablespoons of cheese.
Roll crescent rolls and place on sheet pan.
Bake until crescent rolls are golden and puffed, about 9-12 minutes.
Enjoy!