Preheat the oven to 350 degrees.
Drizzle 1 tablespoon of olive oil over the peppers. Spread the oil over the peppers and sprinkle with salt and pepper to taste.
Flip the peppers, cut side up, and bake for 20 minutes. When done, set aside.
While the peppers are cooking, heat the remaining olive oil over medium heat. Sauté the onions until softened. Then add the jalapeño and sauté 2 more minutes.
Next add the beef, salt, pepper, garlic powder, and Italian seasoning to the pan. Cook and crumble the beef until brown. Drain any fat from the pan.
Add the tomatoes and simmer for 5 minutes. Then stir in the rice and remove from heat.
Fill the cooked peppers with the beef and rice mixture and cover with foil. Bake for 15 minutes.
Remove the peppers from the oven and sprinkle the cheese on top of each pepper. Bake or broil until the cheese is lightly browned, 2-3 minutes.