Beef Braciole with Olives and Raisins

Step 1

Preheat oven to 325°F. Pound beef with the tenderizing side of a meat mallet to 1/8-inch thickness; season with salt and pepper. In a bowl, stir together olives, raisins, 1/2 cup each parsley and cheese, and 1 tablespoon oil.

Step 2

Divide olive mixture evenly among beef slices, patting it down to an even thickness and leaving a 1/4-inch border all around. Starting at one short end, roll each piece into a tight log; secure with twine or a wooden skewer.

Step 3

Heat remaining 3 tablespoons oil in a braiser pan or a wide, shallow ovenproof pot over medium-high. Add beef in a single layer (in two batches, if necessary, to avoid crowding pan) and cook, turning a few times, until browned all over, 8 to 10 minutes. Transfer to a plate.

Step 4

Add garlic and oregano to pan; cook until sizzling and fragrant, about 30 seconds. Add wine and boil, scraping up any browned bits, until mostly evaporated. Return beef and any accumulated juices to pan. Add broth and tomato sauce; bring to a boil.

Step 5

Cover pan and transfer to oven. Cook, spooning sauce over beef a few times, until beef is fork-tender and sauce has reduced to a gravy, 1 1/2 to 2 hours (if gravy reduces and thickens too quickly, stir in more broth).

Step 6

Stir together orange zest, remaining 1/4 cup parsley and 2 tablespoons cheese, and pine nuts. Sprinkle over braciole and gravy before serving.