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In a large skillet, cook sausage over medium heat about 10 minutes or until brown, using a wooden spoon to break up meat as it cooks. Using a slotted spoon, remove sausage from skillet and drain on a paper towel-lined plate. Set aside.
In the same skillet, add pepperoni; cook over medium heat about 5 minutes or until pepperoni starts to crisp, stirring occasionally. Remove from skillet and drain on a paper towel-lined plate.
Meanwhile, in an 8- to 10-quart Dutch oven heat 1 tablespoon olive oil over medium-low heat. Add mushrooms, red onion, red bell pepper and green bell pepper; cook about 10 minutes or until crisp-tender, stirring occasionally. Push vegetables aside with a wooden spoon and add remaining 1 tablespoon olive oil to the bottom of the Dutch oven; add garlic and crushed red pepper flakes to the oil and cook 30 seconds or until garlic is aromatic, stirring frequently.
To the vegetable mixture, add tomatoes, broth, sausage, pepperoni, olives and Italian seasoning. Bring to a boil; reduce heat. Simmer, uncovered, for 20 minutes, stirring occasionally.
To serve, ladle soup into bowls. Sprinkle with cheese and top with croutons.