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How to Make It
Preheat oven to 275°F. Heat oil in a large Dutch oven over high. Sprinkle beef with pepper and salt. Add beef to Dutch oven in batches, and cook, stirring often, until browned on all sides, 8 to 10 minutes. Transfer browned beef to a plate. Set aside.
Reduce heat to medium-high. Add sliced onions and carrots to pan. Cook, stirring occasionally and scraping browned bits from bottom of pan, until onions begin to brown, about 10 minutes. Add garlic; cook, stirring often, until fragrant, about 1 minute. Add tomatoes; use a wooden spoon to break them into chunks. Stir in wine, broth, thyme, bay leaves, and beef. Bring to a boil.
Cover pan. Transfer to oven, and bake at 275°F until beef is tender, about 2 hours.
Meanwhile, spray a large nonstick skillet with cooking spray. Add mushrooms in 2 batches; cook over medium-high, stirring often, until browned, about 5 minutes. Stir mushrooms, pearl onions, and vinegar into beef mixture. Cook, uncovered, over medium-low, stirring occasionally, until pearl onions are tender, about 15 minutes. Remove from heat.