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Stuffed Flank Steak Roll-Ups with Herbed Cheese and Prosciutto

These Stuffed Flank Steak Roll-Ups are filled with garlic-herb spread, prosciutto, and provolone, rolled up into beautiful beef pinwheels. Pan-seared and oven-roasted, they’re tender, juicy, and packed with flavor—perfect for any special meal or weeknight treat.
Prep Time25 minutes
Cook Time20 minutes
Resting Time5 minutes
Total Time50 minutes
Servings: 6

Ingredients

  • 2 –2.5 lbs flank steak butterflied and pounded flat
  • 3 –4 garlic cloves minced
  • 1 small shallot minced
  • 2 tbsp olive oil
  • 2 tbsp fresh parsley finely chopped
  • 1 tsp sage minced
  • 1 tsp basil minced
  • 4 oz thinly sliced prosciutto or turkey slices
  • 4 oz provolone cheese thinly sliced
  • Salt and pepper to taste
  • Kitchen twine and toothpicks

Instructions

  • Preheat oven to 350°F (175°C). Soak toothpicks in water.
  • In a small bowl, combine garlic, shallot, olive oil, parsley, sage, and basil. Mix into a paste.
  • Butterfly and pound flank steak into a flat rectangle, about 1/2 inch thick. Position with grain running side to side.
  • Spread herb paste evenly over the surface, leaving a 1-inch border at the top.
  • Layer with prosciutto and then provolone, also leaving a top edge border.
  • Starting from the bottom, roll the steak up tightly. Place seam-side down.
  • Tie with kitchen twine every 1 inch to secure. Slice into 1-inch pinwheels between twine ties.
  • Season pinwheels lightly with salt and pepper. Skewer with toothpicks.
  • Heat a cast iron skillet over medium-high heat. Sear pinwheels for 3 minutes per side.
  • Transfer skillet to oven and roast for 8–10 minutes, until cooked through.
  • Remove from oven and tent with foil. Rest 5 minutes before removing twine and toothpicks.

Notes

  • Ask your butcher to butterfly the flank steak if you’re short on time.
  • Let the meat rest before slicing for juicier results.
  • Serve with a drizzle of balsamic glaze or a sprinkle of fresh herbs.