Preheat your oven to 400°F (200°C).

On a baking sheet, toss the cherry tomatoes and sliced garlic with 1 tablespoon of olive oil and a pinch of salt. Roast for 15-20 minutes until the tomatoes are blistered and bursting.

While the vegetables roast, bring a large pot of salted water to a boil. Cook the penne pasta according to package directions until al dente, reserving 1/2 cup of pasta water before draining.

In a large skillet over medium heat, warm the remaining 2 tablespoons of olive oil. Add the dried red chili flakes and cook for about 1 minute until the oil turns slightly red and fragrant, being careful not to burn them.

Pour the canned crushed tomatoes into the skillet. Stir in the sugar (if using), salt, and pepper. Simmer on low heat for 10 minutes to thicken the sauce.

Remove the roasted tomatoes and garlic from the oven and mash them slightly with a fork. Stir this roasted mixture into the tomato sauce in the skillet.

Add the cooked penne to the skillet along with a splash of the reserved pasta water. Toss vigorously for 2 minutes until the pasta is well-coated and the sauce clings to the noodles.

Remove from heat and stir in the fresh torn basil leaves immediately.

Serve hot, garnished with plenty of grated Pecorino Romano cheese and extra chili flakes if you desire more heat.