Preheat oven to 450º. Twist a strip of prosciutto around each stalk of asparagus barber pole style. Set aside.
Carefully remove one sheet from roll of phyllo dough and lay evenly on work surface. Cover phyllo dough roll to keep from drying out. Spray sheet of dough liberally with olive oil. Using sharp knife or pizza cutter, divide sheet into 4 equal 9″ long rectangles. Take one prosciutto-wrapped asparagus stalk and lay it just off parallel on one of the short ends of the first dough rectangle. Roll the stalk slightly on the diagonal until it is completely wrapped but for its head, trim the remainder of the dough and lay the stalk on a baking sheet with the trimmed edge of the dough facing down. Repeat with the remaining three rectangles, then spray all four wrapped asparagus stalks with olive oil to keep moist. Continue with remaining asparagus and phyllo dough sheets until all of the stalks are wrapped in dough and coated in olive oil.
Bake for 10 minutes until golden brown. Remove and serve warm or at room temperature. These can be prepared up to four hours in advance of baking. After spraying olive oil on the wrapped asparagus, cover and refrigerate until ready to put in the oven.
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