• Heat the oil in an 8-quart saucepot over medium-high heat. Add onions and squash and cook over medium heat until they're tender-crisp. Remove the vegetables from the saucepot.
• Season the beef as desired. Increase the heat to medium-high. Add the beef to the saucepot and cook until it's well browned on all sides. Remove the beef from the saucepot. Pour off any fat.
• Add the broth, orange juice, wine, brown sugar and tomatoes to the saucepot and heat to a boil. Reduce the heat to low. Return the beef to the saucepot. Cover and cook for 2 hours.
• Return the vegetables to the saucepot. Cover and cook for 1 hour or until the beef is fork-tender.
• Remove the beef to a cutting board. Let stand for 10 minutes. Serve the beef with the vegetables and sauce.
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