Preheat oven to 400°F (204 °C).
Pat the beef bones dry and place in a baking dish with chopped carrots and celery. Toss with 2 tablespoons olive oil. Roast for 45 minutes.
Meanwhile, peel and cube sweet potatoes, pumpkin, and butternut squash. Keep covered in water to prevent discoloration.
In a large soup pot, heat 1 tablespoon olive oil over medium-low heat. Add onion, garlic, scallions, thyme, and black pepper. Cook for 3–4 minutes until fragrant.
Increase heat to medium-high. Add roasted beef and vegetables to the pot, including all pan drippings. Stir well to coat.
Add pumpkin, sweet potatoes, squash, stock cube, allspice, parsley, and enough water or beef stock to cover. Add whole scotch bonnet pepper.
Bring to a boil, then reduce to a simmer. Cover loosely and cook for 1 hour 45 minutes, or until beef is tender and vegetables break down. Skim any foam.
Taste and adjust salt. Remove scotch bonnet before serving. Add flour dumplings or other provisions in the last 10 minutes, if using. Serve hot.
