Preheat your oven to 325°F (163°C). Pat the flank steak completely dry with paper towels and season generously on all sides with kosher salt and black pepper.

Heat 2 tablespoons of olive oil in a large Dutch oven over medium-high heat until shimmering and just beginning to smoke.

Add the flank steak and sear without moving for 4-5 minutes per side until a deep golden-brown crust forms. Remove the beef and set aside on a plate.

Reduce heat to medium. In the same Dutch oven, add the sliced onion, green bell pepper, and red bell pepper. Cook, stirring occasionally, for 6-7 minutes until softened and beginning to caramelize.

Add the minced garlic and cook for 1 minute until fragrant.

Stir in the tomato paste and cook for 2 minutes, stirring constantly, until it darkens slightly and coats the vegetables.

Pour in the white wine and use a wooden spoon to scrape up any browned bits from the bottom of the pot. Let it simmer for 2 minutes.

Add the crushed tomatoes, beef broth, cumin, oregano, smoked paprika, and bay leaves. Stir to combine well.

Nestle the seared flank steak back into the braising liquid, pressing it down so it is mostly submerged. The liquid should come about halfway up the sides of the beef.

Bring the liquid to a gentle simmer on the stovetop, then cover the Dutch oven tightly with its lid and transfer to the preheated oven.

Braise at 325°F for 2.5 to 3 hours, until the beef is completely fork-tender and shreds easily when pressed.

Remove the Dutch oven from the oven. Carefully lift the beef out of the sauce and place it on a large cutting board.

Using two forks, shred the beef into long, irregular ribbons. Discard the bay leaves from the sauce.

Return the shredded beef to the pot. Stir in the green olives and apple cider vinegar. Taste and adjust seasoning with salt, pepper, and the optional teaspoon of sugar if the sauce needs balancing.

Let the shredded beef simmer in the sauce uncovered on the stovetop over medium-low heat for 10 minutes to allow the flavors to meld and the sauce to thicken slightly.

Serve the Ropa Vieja over white rice or cauliflower rice. Garnish generously with fresh chopped cilantro and lime wedges on the side. Pairs beautifully with black beans and sweet plantains.