01 - Set the oven to 320°F (160°C).
02 - Pat beef dry with paper towels then coat evenly in flour, shaking off excess.
03 - Heat 2 tbsp olive oil in a large ovenproof casserole over medium-high heat. Brown beef cubes in batches on all sides. Remove and set aside.
04 - Add remaining 1 tbsp olive oil to the casserole. Cook onions, carrots, celery, and garlic until softened, about 5 minutes.
05 - Return beef to the casserole. Add potatoes, chopped tomatoes, beef stock, red wine, Worcestershire sauce, bay leaves, thyme, rosemary, salt, and pepper. Stir thoroughly.
06 - Bring mixture to a simmer on the stovetop. Cover with a tight lid and transfer to the oven.
07 - Bake for 2 to 2.5 hours, stirring once halfway through, until beef is fork-tender and sauce has thickened.
08 - Remove bay leaves. Adjust seasoning as needed before serving.