- Preheat oven to 350 degrees F (175 degrees C).
- Cook and stir sausage in a large skillet over medium heat until sausage is crumbly and no longer pink, about 10 minutes; drain excess grease, reserving 1 tablespoon of the pan drippings. Transfer drained sausage to a large bowl and set aside. Cook and stir green bell pepper, onion, and garlic in the pan drippings until green pepper is soft, about 8 minutes; transfer to bowl containing sausage.
- Swirl olive oil in the hot skillet and cook and stir zucchini and yellow squash in hot oil until slightly softened, about 8 minutes; stir in tomatoes and Italian seasoning. Season with salt and black pepper. Bring the mixture to a boil and simmer until squash are tender, 10 to 15 more minutes.
- Stir sausage and vegetables into skillet, raise heat to high, and bring mixture to a boil. Reduce heat to medium and cook, stirring often, until the liquid has reduced, about 15 minutes. Spread the mixture into a 9×13-inch baking dish and sprinkle Cheddar cheese over the top.
- Bake in the preheated oven until the mixture is bubbly and the cheese has melted and begun to brown, 25 to 30 minutes.
Cook’s Note:After removing everything at the end, I sometimes strain all of the liquid, reserving it for other recipes, such as using it in beef stew, or as the liquid in a slow-cooker pork tenderloin.
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