Preparation Steps

• Heat the oven to 300°F (150°C). In a small skillet over medium heat, toast the breadcrumbs with 1 tablespoon of the filling olive oil, stirring, until just golden, 2–3 minutes. Transfer to a bowl and cool slightly.
• Stir the Parmesan, parsley, minced garlic, lemon zest, remaining 2 tablespoons filling olive oil, 1/2 teaspoon kosher salt, and 1/2 teaspoon black pepper into the toasted breadcrumbs until evenly moistened; set the filling aside.
• Butterfly the flank steak to create one large, even sheet. Cut into 4 rectangles. Place each between sheets of plastic wrap and pound to about 1/4-inch thickness.
• Lay prosciutto over each piece of beef. Divide the breadcrumb mixture among them, pressing lightly. Roll from the short end into tight logs and tie with kitchen twine every 1 to 1 1/2 inches. Lightly season the outsides with salt and pepper.
• Heat 1 tablespoon olive oil in a heavy Dutch oven over medium-high. Sear the rolls on all sides until well browned, about 2–3 minutes per side. Work in batches if needed. Transfer the seared braciole to a plate.
• Reduce heat to medium and add 1 tablespoon olive oil if the pot looks dry. Add the sliced garlic and cook just until fragrant, 30–60 seconds. Pour in the red wine and simmer 2 minutes, scraping up any browned bits.
• Stir in crushed tomatoes, 1 teaspoon kosher salt, a few grinds of black pepper, and the red pepper flakes. Bring to a gentle simmer. Nestle the braciole into the sauce and spoon some sauce over the tops. Cover and transfer to the oven.
• Braise until the beef is very tender, about 2 hours 15 minutes, turning the rolls once halfway through. Remove from the oven and let rest, covered, for 10 minutes.
• Cut away the twine and slice the braciole into 1/2-inch rounds. Return the slices to the pot and warm gently on low heat for 5 minutes so they absorb more sauce. Off the heat, scatter torn basil over the top.
• Serve with extra Parmesan over cooked pasta or creamy polenta, spooning plenty of sauce over each portion.