3 lb boneless chuck roast
3 tablespoons all-purpose flour
2 tablespoons olive oil
2 large yellow onions, thickly sliced
1 cup red wine
3 cloves garlic, peeled
3 fresh thyme sprigs
2 fresh rosemary springs
2 bay leaves
1 tablespoon tomato paste
4 teaspoons Worcestershire sauce
5 medium carrots, peeled and chopped into 1 1/2-inch pieces
5 medium waxy potatoes (such as Yukon Gold), cut into 1 1/2-inch pieces
Kosher salt and freshly ground black pepper, to taste
Arrange rack in the middle of the oven and preheat to 325°F.
Season roast liberally with salt and pepper and sprinkle flour over roast until evenly coated.
Heat olive oil in a large Dutch oven over medium-high heat. Add roast and sear on all sides until deep golden brown, about 5 minutes per side. Remove roast to a plate and let rest.
Reduce heat to medium and add onions and a 1/2 teaspoon of salt. Sauté until onions are soft and starting to brown, about 4 minutes.
Add red wine and scrape up browned bits from bottom of pan. Stir in tomato paste and Worcestershire sauce, and add garlic, thyme, rosemary, and bay leaves. Return beef and any accumulated juices to the pot.
Bring to a simmer, cover, and place in the oven. Cook for 1 hour 45 minutes. Meat will become tender but won’t yet be falling apart.
Add carrots and potatoes around roast, cover, and return to the oven. Cook until roast pulls apart easily and vegetables are tender, 1 1/2 to 2 hours more.
Slice beef or pull apart with two forks to serve. Enjoy!