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In a large skillet, add 2 Tablespoons of oil and brown sausages, on both sides, over medium-high heat. Remove to a paper towel-lined plate.
Add remaining oil to the skillet. Then add peppers, onion, salt, and black pepper and cook over medium heat, until golden brown, about 8 minutes. Sprinkle Italian seasonings, basil, and garlic and cook until garlic is fragrant about 2 minutes.
Stir in tomato paste, Marsala, and diced tomatoes. Bring to a simmer, scraping the bottom of the skillet to lift up any brown bits.
Slice the sausage in 1-inch pieces and add back to the skillet. Simmer until the sauce has thickened, 20-25 minutes.
Serve in pasta bowls or on toasted Italian rolls split in half lengthwise.