How to make braciole
- Prepare the beef. Cut open a gallon freezer bag along the sides. Working one piece at a time, place the flank steak between the plastic and pound until evenly thin throughout. Even thickness is more important than making the meat paper thin.
- Make the garlic-parsley paste. Combine the garlic, parsley leaves, and olive oil in a food processor or blender. Process until smooth and evenly blended.
- Season and spread. Lay a piece of beef flat on your work surface. Season lightly with salt and pepper, then spread a thin, even layer of the garlic-parsley paste over the surface.
- Add the filling. Sprinkle on a light layer of fresh breadcrumbs, followed by a generous handful of Parmigiano-Reggiano. Top with slices of prosciutto, covering most of the surface without overlapping too heavily.
- Roll. Starting from the narrow end, roll the beef tightly into a cylinder. Do not overfill the braciole; tighter rolls hold together better while braising.
- Tie. Use butcher’s twine to secure each roll, leaving roughly one inch between each loop. Trim away any excess twine.
- Brown in batches. Heat a Dutch oven or heavy-bottomed stainless steel pot over medium-high heat. Add 1 tablespoon of canola oil. Working in batches, brown the braciole on all sides, adding more oil as needed. Transfer the browned braciole to a plate.
- Deglaze. Reduce the heat to medium-low and pour in the red wine. Use a wooden spoon to scrape the browned bits from the bottom of the pot until they dissolve into the wine.
- Build the sauce. Add the whole peeled tomatoes, crushing them gently with a spoon or by hand. Stir in the tomato passata and whole garlic cloves. Season lightly with salt and pepper.
- Braise low and slow. Return the browned braciole to the sauce and bring to a gentle simmer. Reduce the heat to low and cook uncovered until fork tender, about 3½–4 hours. Stir occasionally so the sauce does not stick to the bottom of the pot.
- Rest and serve. Let the braciole rest for about 10 minutes. Remove the butcher’s twine, then serve whole with crusty bread or slice into thick rounds and serve over pasta with plenty of sauce.