Heat the oven: Preheat to 375°F (190°C). Lightly oil a baking dish that will fit all your peppers snugly.
Prep the peppers: Slice off the tops about 1/2 inch down.
Remove seeds and membranes. If a pepper won’t stand, trim a thin slice off the base to level it. Arrange peppers upright in the baking dish.
Soften the peppers (optional but helpful): For more tender peppers, cover the dish with foil and bake empty for 10 minutes.
Or briefly simmer the pepper shells in boiling water for 3–4 minutes, then drain well.
Cook the aromatics: Warm 1 tablespoon olive oil in a large skillet over medium heat. Add the onion with a pinch of salt. Cook 3–4 minutes until softened.
Stir in garlic and cook 30 seconds until fragrant.
Brown the beef: Add ground beef to the skillet. Break it up and cook until browned and no longer pink, about 5–7 minutes. Drain excess fat if needed.
Season the filling: Stir in Italian seasoning, paprika, salt, pepper, and Worcestershire sauce.
Add tomato sauce and drained diced tomatoes. Simmer 3–4 minutes to thicken slightly.
Add the rice: Fold in cooked rice until evenly combined. Taste and adjust seasoning—this is your chance to get the filling just right.
If it seems dry, add a splash of tomato sauce or broth.
Stuff the peppers: Spoon the filling into each pepper, mounding it slightly. Press gently to remove air pockets. Top each with a spoonful of tomato sauce if you like a saucier finish.
Add moisture for baking: Pour 1/2 cup broth or water into the bottom of the baking dish to create steam and keep peppers tender.
Bake: Cover the dish tightly with foil and bake for 25–30 minutes, until the peppers are nearly tender and the filling is hot.
Add cheese: Remove foil, sprinkle shredded cheese over each pepper, and bake uncovered another 8–10 minutes, until melted and lightly golden.
Rest and serve: Let the peppers sit for 5 minutes to settle.
Garnish with chopped parsley or basil. Serve warm with a simple green salad or garlic bread.