Heat the oil in a large, heavy skillet over medium heat. Add the sausages and cook until brown on all sides, 7 to 10 minutes. Remove the sausages from the pan.
Keeping the pan over medium heat, add the bell peppers, onions, salt, and pepper and cook until golden, 5 minutes. Add the garlic, oregano, and basil and cook for 2 minutes. Add the tomato paste and stir until incorporated, then add the Marsala, tomatoes with their juice, and red pepper flakes, if using. Stir to combine, scraping the bottom of the pan with a wooden spoon to release all the brown bits. Bring to a simmer.
Cut the sausages into 4 to 6 pieces each. Return the sausages to the pan. Simmer uncovered until the sauce has thickened, about 20 minutes.
While the sauce simmers, bring a large pot of salted water to a boil over high heat. Add the pasta and cook until tender but still firm to the bite, stirring occasionally, 8 to 10 minutes. Drain the pasta and add to the thickened sauce; toss to combine. Spoon into individual bowls and sprinkle each serving with Parmesan cheese.