Arrange oven rack in middle position and preheat oven to 350°F (175°C).
For the Braciole: In a medium bowl, add breadcrumbs, Parmigiano-Reggiano, parsley, pine nuts, olive oil, garlic, 1/4 teaspoon black pepper, and red pepper flakes and stir until well combined. Set aside.
If using a top round roast, slice roast into six 1/2 -inch slices. If using pre-sliced beef, skip to Step 5.
Lay steak slices 3 inches apart on a cutting board and cover with plastic wrap. Using meat pounder, flatten slices into rough rectangles measuring no more than 1/4 inch thick.
Sprinkle both sides of steaks with salt and remaining 1/2 teaspoon black pepper. Spread the reserved breadcrumb mixture evenly over steaks, then place 1 slice of prosciutto over each breadcrumb-topped steak, folding prosciutto to fit and pressing firmly into steak. Being careful to keep filling in place and starting from a short end of each steak, roll each steak to form a small bundle. Tie each bundle with 2 pieces of kitchen twine to secure.
For the Sauce: In a large sauté pan, heat oil over medium-high heat until shimmering. Add braciole bundles and brown on all sides, 6 to 8 minutes total. Transfer browned braciole to a clean plate; set aside.
Add onion and salt to the now-empty pan and cook over medium-high heat, stirring occasionally, until translucent, about 6 minutes. Add garlic and cook, stirring constantly, until just fragrant, about 1 minute. Stir in wine, scraping up any browned bits from the bottom of the pan, and cook until mixture reduces by half, about 5 minutes. Stir in tomatoes and water. Nestle the browned braciole bundles into the sauce and bring the sauce to a simmer.
Cover the pan with an oven-safe lid or aluminum foil. Place the pan on a rimmed baking sheet and transfer to the oven. Cook, covered, flipping braciole halfway through, for 90 minutes. Carefully remove the lid, flip the braciole again, and continue to cook until the meat is fully tender and sauce thickened to gravy-like consistency, 15 to 45 minutes longer.
Season sauce with salt to taste. Use scissors to cut off twine around each bundle. Transfer braciole to a large serving platter or individual plates and spoon sauce overtop. Serve.
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