Preheat oven to 375 degrees Fahrenheit.

Heat 1 tablespoon of olive oil in a large skillet over medium-high heat.

Working in batches, cook thinly sliced prosciutto in the skillet until crispy, about 2 minutes per side.

Transfer the crispy prosciutto to paper towels to drain excess oil.

Arrange trimmed asparagus spears in a single layer on a rimmed baking sheet.

Drizzle the asparagus with olive oil, turning to coat evenly.

Sprinkle the asparagus with pepper and lightly with salt.

Roast the asparagus in the preheated oven until tender, approximately 25 minutes.

Remove the roasted asparagus from the oven and let it stand at room temperature.

Arrange the roasted asparagus on a serving platter.

Crumble the crispy prosciutto over the asparagus.

Serve the dish warm or at room temperature.