Heat oven to 375°. Drop asparagus in 1/2 inch of boiling water in a 10-inch skillet. Simmer, covered, for 3 minutes. Drain and immediately plunge asparagus into bowl of ice water to cool; drain on paper towels.
Unroll dough on ungreased cookie sheet and press into 8x11-inch rectangle, sealing perforations. Prick with fork. Bake 6–9 minutes until light golden brown. Sprinkle with 1/2 the cheese; top with ham strips. Sprinkle with remaining cheese. Place asparagus spears in rows over cheese, alternating tips. Brush asparagus with oil; sprinkle with pepper flakes.
Bake 5–7 minutes more until crust edges are golden brown and cheese is melted. Cool 5 minutes. Cut into squares. Serve warm.
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