Preheat the oven to 400 degrees Fahrenheit. Using parchment paper, line a half-sheet pan (optional).
Cook the pasta according to the package directions. Before draining, save at least 1/2 cup of the cooked pasta water.
Cut the garlic cloves into 2-3 pieces. On a sheet pan, arrange the cherry tomatoes and garlic. Drizzle with 2 tablespoons olive oil and coat with clean hands.
Roast the cherry tomatoes and garlic for 20 minutes on the middle oven rack at 400°F. After 10 minutes, take the tomatoes from the oven and toss to ensure equal cooking. Return to the oven for 10 minutes, or until the cherry tomatoes have burst and the skins have shriveled.
Preheat a medium saucepot to medium-high heat. Drizzle in 1 tablespoon of olive oil and add the dried herbs (oregano, thyme, parsley, rosemary). Cook for 30 seconds to a minute, stirring often to avoid scorching.
Add the cherry tomatoes, garlic, and any liquid that has accumulated on the pan, salt, and 1/4 cup basil. To blend, stir everything together. To thin the sauce, add 1/4 cup of pasta water.
Once the mixture is simmering, decrease the heat to low and let it be uncovered for 5 minutes. Thin with the remaining 1/4 cup pasta water as required. Check for salt.
Serve the pasta with the cherry tomato sauce, leftover basil, freshly ground black pepper to taste, and a sprinkle of Parmesan cheese on top (optional). Enjoy!