Heat oven to 325 F°. Put diced eggplant into a bowl and drizzle with 2 tbsp. oil. Toss to combine and season with freshly ground pepper and a pinch or two of dry oregano.Transfer eggplant to a parchment-lined baking sheet and bake for about 20 minutes. Transfer to a rack; set aside.
Heat remaining oil in a 3.5-qt. saucepan over medium heat. Add the onion and cook, stirring, about 2 minutes—season with sea salt. Add the garlic, a generous pinch of dry oregano, the bay leaf, the cinnamon stick, a pinch of chili flakes (optional) and cook, stirring, for about 3 minutes.
Add the ground sausage. Use a wooden spoon to break it up into small pieces until browned, 5-10 minutes. Add half a cup of broth and simmer for 10 minutes.
Add the San Marzano tomatoes. Break the whole tomatoes into smaller pieces. Add the cherry tomatoes(leave them whole), eggplant pieces, and half the basil, stir, and cover with the lid. Cook in medium heat for 15 minutes.
Meanwhile, bring a large pot of salted water to a boil. Add the pasta and cook until just al dente, about 10 minutes. Drain pasta and transfer 3 cups to the eggplant sauce. Adjust seasoning to your liking; see if it needs a little salt. Add some fresh basil and a pinch or two of chili flakes (optional).Toss and serve in bowls with some chopped fresh basil on top and a generous amount of parmesan cheese.
You can make this sauce ahead of time and reheat it:
Toss the eggplant in the sauce, cool, and use it whenever you need it over pasta, polenta, mashed potatoes, or anything else you might like. Add a little water to loosen up the sauce while heating on the stove or in the microwave.
For reheating with the pasta already in the sauce, add some water as needed to loosen up the sauce. Don't overdo the water!
Nutritional Info – Please keep in mind that the nutritional information provided is only an estimate and can vary based on the products used.