Stuffed Flank Steak Roll-Ups with Herbed Cheese and Prosciutto

Roll up your sleeves—this dinner is about to impress! These Stuffed Flank Steak Roll-Ups are an elegant, flavorful dish perfect for weekends, holidays, or when you just want to feel a little fancy without too much fuss. Inside each juicy beef pinwheel is a savory mix of herbs, prosciutto, and provolone, rolled up and roasted to perfection.

Let’s be honest—flank steak doesn’t always get the spotlight it deserves. But when it’s butterflied, seasoned, filled with aromatic herbs and creamy cheese, and then rolled into beautiful spirals, it becomes the star of the plate. The pinwheel presentation makes this dish look gourmet, but it’s actually quite approachable once you know the steps.

The flavor combo here is a knockout: garlic, shallot, parsley, sage, and basil blended with olive oil for a rich, herbal base. This mixture infuses the beef with flavor from the inside out. Then comes the prosciutto—delicate and salty—and provolone cheese, which melts into gooey deliciousness as the steak cooks.

What makes this recipe a weeknight contender as well as a special occasion stunner? You can prep it ahead of time! Tie up the roll, refrigerate it, and pop it in the oven when ready. And once it’s sliced, each pinwheel is like a mini masterpiece.

This dish is naturally low-carb and high-protein, so it fits into many lifestyles. Serve with a fresh salad, garlic mashed potatoes, or roasted veggies depending on your mood.

Don’t be afraid of the rolling and tying—it’s easier than it looks. A sharp knife and a little patience are your best friends. Plus, if your roll isn’t perfect, no worries—it’ll still taste amazing.

Searing the pinwheels before roasting is key. It locks in juices, adds a golden crust, and boosts flavor. Use a cast iron skillet if you have one for that steakhouse-style sear.

Once they’re roasted, let the pinwheels rest before slicing. This keeps the juices in and the cheese where it belongs—inside!

You can even experiment with different fillings. Swap prosciutto for turkey or roast beef, or use mozzarella or goat cheese instead of provolone. Just keep the layer thin so everything rolls up tight.

These roll-ups also make a fantastic main for entertaining. Pair with a glass of sparkling water or juice, and serve with a grainy mustard or balsamic glaze on the side for dipping.

Whether you’re hosting or just treating yourself, these steak spirals are a surefire way to elevate dinner without breaking a sweat.

Servings: 4–6 servings
Prep Time: 25 minutes
Cook Time: 20 minutes
Rest Time: 5 minutes
Total Time: About 50 minutes

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:

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

Tips:

• 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.

Why You’ll Love These Roll-Ups:

• Elegant presentation with minimal effort.
• Customizable with your favorite deli meats and cheeses.
• Big on flavor and perfect for guests.
• Prep-ahead friendly for entertaining ease.

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.