Heat the olive oil in a large, deep skillet on medium heat.
Once hot, sauté the onions until tender. Use a slotted spoon, transfer the onions to a dish with the grated carrot and set off to the side.
Repeat with the zucchini and yellow squash until soft and edges golden.
Add the carrots and onions back into the pan and add in the garlic, basil, oregano, italian seasoning and red pepper flakes (if using). Cook for 1-2 minutes.
Pour in the crushed tomatoes, wine and sugar. Simmer uncovered over medium-low heat for 45-60 minutes, stirring ocassionaly.
With 20 minutes left on the clock, prepare the pasta according to the package directions. Keep in mind, larger pastas take longer to cook.
Lastly add the half cup of Parmesan, taste and season with kosher salt and black pepper to taste.
Serve over pasta with reserved parmesan.