Prepare a large baking sheet with foil. Add the tomatoes to the baking sheet.
Add the olive oil, add the pressed garlic, salt, oregano, and chili flakes.
With your hands, mix together the tomatoes, so the oil and seasoning is evenly dispersed. Spread the tomatoes out evenly and place in the oven.
Add another shake of salt and a few cracks of pepper!
Bake for about 45 minutes, stirring once or twice to turn over the tomatoes (mix it up!) until the tomatoes are roasted. The tomatoes will eventually be candied, crinkly, and shriveled up. They will taste very sweet, but also very savory! If you want them a little more crunchy, you can place them back in the oven for another 15 minutes.
Make the pasta dish:
Scrape the tomatoes into a serving dish and add the pesto.
Prepare the pasta according to package directions, cooking it al dente (about 1 minute less).
Drain the pasta, reserving 1 cup of the pasta water, and add the pasta back into the pot. Add the pasta water, pesto, and roasted tomato mixture, and Parmesan cheese; gently toss together.
Serve with a sprinkle of Parmesan cheese and a sprinkle of fresh chopped basil (or oregano, or both).