1. Preheat your oven to 300°F (150°C). In a large oven-safe pot or Dutch oven, heat the olive oil over medium-high heat.
2. Season the beef chuck roast generously with salt and pepper. Sear it in the hot oil until browned on all sides, about 4-5 minutes per side. Remove the roast and set aside.
3. Add the chopped onion to the pot and sauté until translucent, about 3 minutes. Stir in the garlic and cook for another minute or until fragrant.
4. Pour in the crushed tomatoes, beef broth, and tomato paste. Add the oregano, basil, and red pepper flakes if using. Stir to combine.
5. Return the roast to the pot, ensuring it’s submerged in the sauce. Cover with a lid and transfer to the preheated oven.
6. Bake for 3-4 hours, or until the beef is fork-tender and the flavors have melded beautifully. Check occasionally and spoon sauce over the roast to keep it moist.
7. Once done, remove from the oven and let it rest for a few minutes. Garnish with fresh parsley before serving.

My secret tip? Make this dish a day ahead. The flavors deepen overnight, and it makes for a fantastic next-day meal.