Preheat your oven to 425°F. Line a large, rimmed baking sheet with high-heat-resistant parchment paper.
Cut the tough ends off the asparagus. Spray the asparagus with olive oil.
Using a sharp knife, cut each prosciutto slice in half lengthwise.
Tightly wrap each half prosciutto slice around the middle of each asparagus spear.
Arrange the wrapped asparagus spears on the prepared baking sheet in a single layer. Lightly spray them with more oil. Bake until the asparagus is tender-crisp, for 8-10 minutes.
Season the asparagus with freshly ground black pepper and red pepper flakes, sprinkle it with parmesan, and serve.
Video
Notes
Prosciutto is very thinly sliced and tears easily. Cutting the prosciutto slices and wrapping them around the asparagus is not easy to do. But try not to worry about it too much. Even if the prosciutto tears, you can still wrap it as best as you can around the asparagus, perhaps using more than one piece of prosciutto per spear, and it would all come together in the oven.
Don't add salt – there's plenty of it in the prosciutto and parmesan.
It's best to use relatively thick asparagus spears in this recipe.
You can keep the leftovers in the fridge, in an airtight container, for up to 4 days. Reheat them in the microwave, covered, at 50% power. I don't recommend freezing the leftovers.