Preheat the oven to 450˚F. Line one half sheet pan with tin foil and another with parchment paper.

Add washed cherry tomatoes with stems removed to the tin foil-lined sheet pan. Add halved olives, capers, chopped sun-dried tomatoes, 2 tablespoons olive oil, 1 teaspoon kosher salt, 1/2 teaspoon black pepper, red chile pepper flakes, and dried oregano to the pan and toss everything together with clean hands.

Slice squash into 1/4” thin rounds and thinly slice the onion. Add both to the parchment-lined sheet pan. Add whole garlic cloves with the skins on, remaining 2 tablespoons olive oil, 1/2 teaspoon of salt and 1/2 teaspoon black pepper. Toss everything together with clean hands and arrange squash slices into 1 layer so they don’t overlap.

Bake both trays at 450˚F for about 30 minutes until tomatoes are browned and sauce is bubbling, and the squash and onions are browned and garlic is soft.

Meanwhile, bring a large pot of salted water to a boil and cook pasta according to package instructions or until pasta is al dente, then drain and add pasta to a large serving dish. Time the pasta cooking time to be done when the sauce and squash are done.

When the tomato sauce is done roasting, remove from the pan the oven. Taste for salt first then carefully lift up the tinfoil with both hands and pour the sauce over the cooked pasta. Use kitchen tongs or a serving spoon and fork to toss and coat the pasta in the sauce.

Add the roasted squash and onions to the dish and then squeeze out the roasted garlic into the dish. Use the tongs to incorporate the veggies evenly throughout the pasta.

Top the pasta with fresh basil leaves and drizzle good quality olive oil all over the dish.

Serve right away as is or with freshly grated parmesan or pecorino cheese.