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Preheat grill to medium.
Toss asparagus with oil, salt and pepper in a medium bowl. Wrap 1 length of prosciutto around the middle of 4 asparagus spears. Repeat, making 4 bundles. Oil the grill rack. Grill the asparagus bundles, turning once or twice, until the asparagus is tender and charred in spots, about 10 minutes.