1. Prepare the Beef

Begin by preparing the beef. If you’re using flank steak or skirt steak, season both sides generously with salt, black pepper, and a sprinkle of cumin and paprika for extra flavor. The beef should be seasoned thoroughly to ensure that each piece absorbs the seasoning while cooking.

Next, heat 1 tablespoon of olive oil in a large Dutch oven or heavy-bottomed pot over medium-high heat. Once the oil is hot, sear the beef on both sides until it’s browned, about 3-4 minutes per side. This step adds a deep layer of flavor to the beef and forms a nice crust. Once the beef is seared, remove it from the pot and set it aside on a plate.

2. Sauté the Vegetables

In the same pot, add the remaining 1 tablespoon of olive oil. Add the sliced onions, bell peppers, and minced garlic to the pot. Sauté for about 5-6 minutes, until the onions are soft and translucent and the peppers begin to soften. The garlic should be fragrant but not burnt, so stir frequently.

As the vegetables cook, they will absorb any leftover browned bits from the beef, adding even more flavor to the dish.

3. Add the Tomatoes and Spices

Once the vegetables are softened, stir in the tomato paste, allowing it to cook for about 1-2 minutes. This will help develop a rich base flavor. Then, add the diced tomatoes, beef broth, cumin, paprika, oregano, and bay leaf to the pot, stirring well to combine. These ingredients will form the sauce that the beef will cook in, so make sure everything is evenly mixed.

Bring the mixture to a simmer, and let it cook for 5-10 minutes to allow the flavors to start melding together.

4. Return the Beef to the Pot

Once the tomato mixture has simmered, return the seared beef to the pot. Add any juices from the plate back into the pot as well. The beef should be mostly submerged in the sauce. Cover the pot with a lid, reduce the heat to low, and let it simmer gently for 2 to 2 ½ hours. This slow simmer allows the beef to become tender and absorb the rich flavors of the sauce.

Periodically check the beef, ensuring there’s enough liquid in the pot. If necessary, add a little more beef broth or water.

5. Shred the Beef

Once the beef is tender and easily shreds with a fork, remove it from the pot and set it on a cutting board. Use two forks to shred the beef into thin strips. This is the traditional method of preparing Ropa Vieja, as the beef shreds easily when it’s properly cooked.

Return the shredded beef to the pot and stir it into the sauce. The beef will soak up all the wonderful flavors of the tomato sauce and spices.

6. Add the Final Touches

To finish the dish, add the sliced green olives, capers, white vinegar, and brown sugar to the pot. Stir everything together, and let the beef simmer in the sauce for an additional 10-15 minutes to allow the flavors to meld. The olives and capers add a briny, tangy flavor that cuts through the richness of the beef, while the vinegar and brown sugar balance out the acidity and sweetness of the tomatoes.

Taste the dish and adjust the seasoning if needed, adding more salt or pepper to suit your taste.

7. Serve the Cuban Shredded Beef

Once the dish is finished cooking, serve the Cuban Shredded Beef with your choice of accompaniments. It’s typically served with white rice, black beans, and fried plantains, which complement the rich, savory flavors of the beef. You can also garnish the dish with freshly chopped cilantro for a burst of color and freshness.