1Pat the beef chuck dry with paper towels. Season all over with salt and pepper.
2Heat olive oil in a dutch oven over medium-high heat. Working in batches if needed, brown the meat on all sides until deep golden, about 10–12 minutes total. Transfer to a plate.
3Reduce heat to medium. Add diced onion and cook until softened, about 4 minutes. Stir in garlic, tomato paste, and flour, cooking for 1 minute.
4Pour in broth and wine (if using), scraping up any browned bits stuck to the bottom. Return the beef to the pot along with carrots cut into 2-inch chunks, potatoes cut into 1.5-inch chunks, thyme, rosemary, and bay leaves.
5Bring to a simmer, then cover and transfer to a 325°F oven for 2.5 to 3 hours, until the beef shreds easily with a fork and vegetables are tender.
6Remove from oven. Discard herb sprigs and bay leaves. Taste and adjust seasoning. Serve the beef and vegetables in bowls with the braising liquid spooned over top.