Prep the Peppers: Slice the tops off the bell peppers and remove seeds and membranes. Rinse under cold water. Brush lightly with olive oil and season with salt and pepper. Arrange them in a baking dish so they stand upright, ready to be filled.
Cook the Beef Filling: Heat a large skillet over medium heat. Add ground beef and cook until browned, breaking it apart with a wooden spoon. Drain excess fat. Add chopped onions and garlic, cooking until fragrant and translucent. Stir in diced tomatoes, cooked rice, Italian seasoning, paprika, salt, and pepper. Mix well to combine evenly.
Stuff the Peppers: Spoon the beef mixture into each pepper until full. Press gently to pack the filling, but don’t overfill. Sprinkle shredded cheddar cheese generously on top of each stuffed pepper.
Bake: Preheat oven to 375°F (190°C). Cover the baking dish with foil and bake for 30 minutes. Remove the foil and bake an additional 10–15 minutes until the peppers are tender and the cheese is golden and bubbly.
Serve: Let the stuffed peppers cool for 5 minutes. Serve whole on plates with a little of the tomato-juice mixture spooned over the top. They’re ready to enjoy while piping hot.