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Take the chuck roast out of the fridge 30 minutes before cooking. Pat dry with paper towels and season generously on all sides with salt and pepper.
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Preheat oven to 325°F. Heat vegetable oil in a large Dutch oven over medium-high heat. Sear the roast for 4-5 minutes per side until deep brown on all sides (12-15 minutes total). Remove to a plate.
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In the same pot, cook quartered onion for 2-3 minutes. Add smashed garlic and tomato paste, stirring for 1 minute. Pour in beef broth and scrape up the brown bits from the bottom (deglazing). Add Worcestershire sauce if using.
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Nestle the seared roast back into the pot. Tuck rosemary, thyme, and bay leaf around it. The broth should come about halfway up the sides. Put the lid on and place in the middle rack of the oven.
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After 2 hours, open the Dutch oven carefully and add potatoes, carrots, and celery around the roast. Replace the lid and return to the oven for another 1 to 1.5 hours.
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The roast is done when it falls apart easily with a fork (about 3 to 3.5 hours total). Remove from oven and let rest with lid on for 10 minutes. Remove bay leaf and herb stems.
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Transfer the roast to a cutting board or pull apart in the pot. Arrange vegetables on a platter, spoon braising liquid over everything, and serve with crusty bread.