Taking each tomato, carve out a circle at the top to remove the stem. Using a spoon, scoop out the inside of the tomato so there is only an outside layer about 1/8 inch thick. Save the inside!
Place the tomatoes in the muffin tin and turn the oven on to 350.
In skillet, heat olive oil and add chopped onion and 4 cloves of garlic. As they start to cook through, add your Italian sausage.
Season with half of the oregano, half of the Italian seasoning, salt and pepper, and cook until sausage is done.
Mix about half of the Mozzarella cheese and a few chopped basil leaves into the sausage mixture and spoon equally into the tomato cups.
Cover with tin foil and place in the oven for about 20 minutes.
Returning to the skillet, add more olive oil and a clove or two of garlic. Add the insides of the tomato along with the tomato paste, stirring well, and simmer on low.
As the sauce starts to thicken, add the remaining oregano, Italian seasoning, red pepper, and a healthy amount of salt. Continue to let reduce, tasting along the way.
Taking the tomatoes out of the oven, spoon about a tablespoon of sauce into each cup and top with the remaining mozzarella cheese, and about half of the parmesan. Return to the oven uncovered.
When browned, plate with a little fresh parmesan, drizzle of the remaining sauce, and the rest of the chopped basil and enjoy!A variation: I used a muffin tin because of the size of the tomatoes I had, but I've also done this same technique in ramekins. You could use a sheet pan if you don't have either, it just helps to support so the tomato stays upright.