01 - Preheat oven to 375°F (190°C). Bring a large pot of salted water to a rolling boil. Submerge bell peppers and blanch for 3 minutes. Remove from water and drain thoroughly, invert on paper towels.
02 - Heat olive oil in a large skillet over medium heat. Add diced onion and sauté for 3 minutes until softened. Incorporate minced garlic and cook for an additional 30 seconds until fragrant.
03 - Add ground beef to the skillet. Cook, breaking apart the meat with a spoon, until thoroughly browned, approximately 5-7 minutes. Drain any excess rendered fat.
04 - Stir in tomato sauce, tomato paste, Worcestershire sauce, brown sugar, smoked paprika, chili powder, salt, and black pepper. Reduce heat and simmer for 5 minutes, allowing the mixture to thicken.
05 - Arrange blanched peppers upright in a baking dish. Spoon the Sloppy Joe mixture generously into each pepper. Top each filled pepper with shredded cheddar cheese. Cover the baking dish loosely with aluminum foil and bake for 25 minutes. Remove foil and continue baking for another 10 minutes, or until the cheese is melted and golden brown.
06 - Allow the stuffed peppers to rest for 5 minutes before serving.