Step 1: Preheat your oven to 400°F (200°C). Line a baking sheet with parchment paper.
Step 2: In a medium bowl, toss the halved cherry tomatoes with 2 tablespoons of olive oil, minced garlic, 1/2 teaspoon of salt, and 1/4 teaspoon of black pepper. Ensure they are well coated.
Step 3: Spread the seasoned tomatoes in a single layer on the prepared baking sheet. Do not overcrowd the pan; use two sheets if necessary.
Step 4: Roast for 20-25 minutes, or until the tomatoes are tender, slightly shriveled, and their juices have begun to caramelize. Remove from the oven and set aside.
Step 5: While the tomatoes are roasting, bring a large pot of heavily salted water to a rolling boil. Add the pasta and cook according to package directions until al dente.
Step 6: Before draining, reserve about 1 cup of the starchy pasta cooking water. This will be used to create a silky sauce.
Step 7: Drain the cooked pasta thoroughly and return it to the large pot or a spacious serving bowl.
Step 8: Add the pesto to the hot pasta. Stir well to coat the pasta evenly.
Step 9: Gradually add 1-2 tablespoons of the reserved pasta water, stirring until the sauce emulsifies and achieves a smooth, creamy consistency that clings to the pasta.
Step 10: Gently fold in the roasted tomatoes, including any flavorful juices remaining on the baking sheet.
Step 11: Stir in 1/2 cup of freshly grated Parmesan cheese and the 1/4 cup of fresh basil leaves.
Step 12: Taste and adjust seasoning as needed. Serve immediately, garnished with additional Parmesan cheese and fresh basil, if desired.