Preheat your oven to 350°F (175°C).
In a skillet over medium heat, sauté the chopped bell pepper and onion until softened, about 5 minutes. Add minced garlic and cook for 1 more minute. Remove from heat and let cool.
In a large mixing bowl, combine the ground beef, sautéed vegetables, bread crumbs, eggs, Worcestershire sauce, salt, black pepper, paprika, and oregano. Mix until well combined.
Stir in ½ cup of shredded provolone cheese into the meat mixture.
Transfer the meat mixture to a loaf pan and shape it into a loaf. Spread ketchup evenly on top.
Bake in the preheated oven for about 60 minutes, or until the meatloaf is cooked through and reaches an internal temperature of 160°F (70°C).
In the last 10 minutes of baking, sprinkle the remaining ¼ cup of shredded provolone cheese on top of the meatloaf. Return to the oven until the cheese is melted and bubbly.
Remove the meatloaf from the oven and let it rest for 10 minutes before slicing. Serve warm.