In a small bowl, stir together flour, salt and pepper. Dust roast with seasoned flour, patting off excess.
Pour oil into a heavy-bottomed Dutch oven with a tight-fitting lid over medium-high heat. When oil faintly smokes, add roast. Turn to brown on all sides, 8-10 minutes. Remove meat to a plate and set aside. Remove 1 tbsp of drippings and discard the rest.
Add diced onion and celery to drippings in pot. Saute until onion softens and both are translucent, 3-5 minutes. Add garlic and saute 1 minute or until fragrant. Add tomato paste and herbs and cook, stirring frequently, 3 minutes until tomato begins to brown.
Add wine, stirring to loosen any fond (browned bits) on the bottom of the pot. Simmer 5 minutes, or until wine reduces by at least 2/3.
Add carrots, potatoes and pearl onions. Return meat to pot and add broth. Heat to simmering.
Cover tightly and transfer to oven. Bake, covered, 2 hours. Carefully remove lid and bake another 30 minutes, or until beef is fork-tender. Skim off and discard any accumulated fat.
Transfer beef to a clean platter and rest, tented with foil, 10 minutes before serving. Adjust seasoning of sauce with salt and pepper to taste. Serve with vegetables and gravy alongside.