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Preheat oven to 350 degrees F.
In a large pot of boiling salted water, cook pasta according to package instructions until al dente; drain well.
Heat 1 tablespoon olive oil in a large cast iron skillet over medium high heat. Working in batches, add zucchini and squash, and cook, stirring occasionally, until golden, about 3-4 minutes; set aside.
Add remaining 1 tablespoon olive oil to the skillet. Stir in sausage, bell pepper and onion until golden, about 4-5 minutes. Stir in garlic and Italian seasoning until fragrant, about 1 minute.
Stir in diced tomatoes. Reduce heat and simmer until slightly thickened, about 7-10 minutes; season with salt and pepper, to taste.
Stir in pasta, zucchini, squash and basil until well combined; sprinkle with cheese.
Place into oven and bake until bubbly and golden brown, about 15 minutes.
Serve immediately.