Step 1

Prepare the sugo al pomodoro sauce and set aside.

Step 2

In a medium bowl, stir together bread crumbs, garlic, cheese, parsley, and basil until combined. Add half the olive oil (2 tablespoons)—season the mixture with salt and pepper and set aside.

Step 3

Lay the flank steak flat on a wooden board or clean work surface. Pat the steak dry with paper towels. Place one piece between two sheets of parchment paper. With a rolling pin or meat mallet, pound the meat to flatten it to about 1/4 inch thickness—  season both sides generously with salt and pepper.

Step 4

Sprinkle the breadcrumb mixture over the steak to cover the meat. Add slices of prosciutto over the pounded beef and breadcrumb mixture to cover evenly.

Step 5

Starting at the short end, roll up the steak (like a jelly roll) to seal the filling. Using butcher’s twine, tie the steak roll to secure it (I usually secure it in 4 spots).

Step 6

Preheat the oven to 350 degrees F.

Step 7

Heat the remaining 2 tablespoons of oil in a heavy large ovenproof skillet, or cast iron pan, over medium heat. Add the braciole to the pan and cook until browned on all sides, about 8 minutes.

Step 8

Add the wine to the pan and scrape all the browned bits from the bottom of the pan. Bring it to a boil for about 1 minute. Stir in the prepared tomato sauce. Cover partially with foil or an oven-safe lid, and bake until the meat is almost tender. Baste the braciole with the sauce every 30 minutes.

Step 9

After 1 hour, uncover and continue baking until the meat is tender, about 30 minutes longer. The total cooking time should be about 90 minutes total. You can braise the meat for up to 3 hours. If cooking longer, ensure the sauce doesn’t reduce too much, and add a little beef broth if needed.

Step 10

Let the braciole rest for 15 minutes. Remove the butcher’s twine from the braciole. Remove the braciole from the sauce. Cut the braciole crosswise and diagonally into 1/2-inch-thick slices using a large sharp knife. Transfer the slices to plates. Spoon the sauce over and serve. Enjoy with ciabatta bread to soak up the sauce.