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Prepare baking sheet and oven: Line a broiler-safe baking sheet with foil. Preheat oven to broil with rack about 6 inches from heat source.
Wrap asparagus with prosciutto: Place asparagus on pan. Drizzle asparagus with oil and sprinkle with salt, pepper, and garlic; toss to coat. Wrap 1 prosciutto slice around each asparagus spear, going at a diagonal angle. Try to ensure some garlic adheres to each asparagus spear, but don’t worry if there’s some garlic left on the pan. Evenly space wrapped asparagus on pan.
Broil asparagus: Broil asparagus until prosciutto is browned and crisp, 6 to 8 minutes, turning asparagus over halfway through cooking.