Preheat your oven to 400°F (200°C). This high temperature will help caramelize the sugars in the tomatoes, enhancing their flavor.

In a large bowl, combine the halved cherry tomatoes, smashed garlic, olive oil, salt, black pepper, and dried oregano. Toss until the tomatoes are evenly coated.

Spread the tomato mixture onto a baking sheet in a single layer. This ensures even roasting.

Roast in the preheated oven for 25-30 minutes, or until the tomatoes are blistered and caramelized. Stir halfway through for even cooking.

While the tomatoes are roasting, bring a large pot of salted water to a boil. The salt enhances the pasta's flavor.

Add the pasta to the boiling water and cook according to package instructions until al dente, usually about 8-10 minutes.

Once cooked, reserve 1 cup of pasta water, then drain the pasta in a colander.

In a large skillet over medium heat, combine the roasted tomatoes (including the garlic) and the cooked pasta. Toss gently to combine.

Add the chopped fresh basil and grated parmesan cheese. If the mixture seems dry, add reserved pasta water a little at a time until you reach your desired consistency.

Drizzle with olive oil and sprinkle with red pepper flakes, if using. Toss again to combine.

Serve immediately, garnished with extra parmesan cheese and fresh basil.