Steak Prosciutto & Cheese Recipe

Prepare steak

Remove steak from the refrigerator 20–30 minutes before cooking to come toward room temperature. Pat dry with paper towels. If the steak is unevenly thick, use a meat mallet or rolling pin (covered in plastic wrap) to gently pound thicker areas to an even thickness of about 1/2 inch to 3/4 inch for easier rolling and even cooking.

Season

Brush both sides of the steak with 1 tablespoon olive oil. Sprinkle kosher salt, black pepper and garlic powder evenly on both sides, pressing lightly so seasoning adheres.

Sear

Heat a large oven-safe skillet (cast iron preferred) over medium-high heat until shimmering. Add the steak and sear undisturbed 2–3 minutes on the first side until a brown crust forms. Flip and sear the other side 1.5–2 minutes. The goal is a good crust; the steak will finish cooking after assembly. Remove skillet from heat.

Layer prosciutto and cheese

Place the seared steak on a cutting board. Arrange 6 slices of prosciutto to cover most of the top surface of the steak in a single layer. On top of the prosciutto lay 6 slices of provolone (or chosen cheese) so the cheese evenly covers the prosciutto. Tuck a few basil leaves under the cheese slices if using for flavor.

Roll the steak

Starting at one narrow end, tightly roll the steak away from you, keeping the prosciutto and cheese tucked inside so they form a seam on the bottom. Use kitchen twine to tie the roll at 1 1/2–2 inch intervals with three ties to hold shape. Trim excess twine ends.

Sear seam and baste

Return the skillet to medium heat. Add 1 tablespoon butter and let it foam. Place the steak roll seam-side down and sear 1 minute to seal. Rotate to sear other sides briefly (30–45 seconds each) to develop an even color.

Roast to finish

Preheat oven to 400°F (200°C) if not already hot. Transfer the skillet with the steak roll to the oven and roast 6–10 minutes for medium-rare (internal temp 125–130°F/52–54°C), 10–14 minutes for medium (135°F/57°C). Use an instant-read thermometer inserted into the center to check doneness. Remove from oven when 5°F/3°C below target since it will rest and rise slightly.

Rest and finish

Transfer the steak to a cutting board and tent loosely with foil. Let rest 8–10 minutes. While resting, squeeze 1/2 lemon over the skillet pan juices (optional) and spoon the flavored butter/juices over the rolled steak before slicing. Remove twine.

Slice and serve

Using a sharp knife, slice the roll crosswise into 1/2–3/4 inch medallions so each piece shows the prosciutto and melted cheese spiral. Arrange on a platter, spoon any reserved pan juices over the slices, and finish with a light dusting of freshly grated parmesan and extra basil leaves if desired. Serve immediately.