Preheat the broiler/grill to high. Line a large, rimmed baking pan with parchment paper and set aside.

Cut each strip of prosciutto in half lengthwise. Wrap each trimmed asparagus spear with a strip of prosciutto, starting just below the tip and wrapping toward the bottom.

Arrange the wrapped asparagus spears on the lined baking sheet, leaving plenty of room between the spears. Use a second pan or work in batches, if necessary.

Brush each spear with olive oil and season with freshly cracked black pepper, to taste. (Avoid adding excess salt because the prosciutto is naturally salty).

Place the baking pan with prepared spears under the broiler/grill and cook for about 4-5 minutes. Remove the pan from the heat and carefully turn each spear before placing back under the broiler. Broil for another 2 or 3 minutes, or until the prosciutto is crispy and the asparagus is tender.

Remove spears from the baking sheet and place them on a wire cooling rack placed over another baking sheet to allow excess grease to drain. Dab lightly with a paper towel, if desired.

Transfer the grilled prosciutto-wrapped asparagus to a serving tray and serve them immediately.