Ready to get cooking? Follow these comprehensive steps to create your Italian stuffed flank steak masterpiece.

Start by placing the flank steak on a cutting board. If not already done, butterfly the steak by slicing it horizontally, not cutting all the way through, so it opens like a book. Gently pound the steak to an even thickness, about half an inch.

Generously season both sides with salt and freshly cracked black pepper. This step is crucial for building flavor; don’t skimp on it!

In a mixing bowl, combine the provolone cheese, minced garlic, prosciutto, lemon zest, chopped shallot, minced basil, chopped sage, flat-leaf parsley, and crushed red pepper flakes. Mix well to ensure an even distribution of flavors.

Spread the stuffing over one side of the steak, leaving about an inch of space around the edges. Gently press the mixture down to make sure it adheres to the steak. This is like making a delicious bed for our meat.

Starting from the filled side, roll the flank steak tightly toward the opposite edge. Tuck in the sides as you go to keep the stuffing intact.

Using the soaked toothpicks, secure the roll at 1-inch intervals. The toothpicks will hold everything together during cooking, so ensure they are in place.

Drizzle the rolled flank steak with olive oil and rub it over the entire surface. This will help to brown the steak beautifully in the oven.

Preheat the oven to 375°F (190°C). Place the stuffed steak in a roasting pan and cook for 25-30 minutes or until the internal temperature reaches 145°F (63°C) for medium rare.

Once cooked, remove the steak from the oven. Let it rest for at least 10 minutes before slicing. This allows the juices to redistribute, making each slice moist and tender.