Bring a large pot of salted water to a boil. Add the penne and cook 1 -2 minutes less than the package directions. Drain, saving the pasta water.
In a large skillet or braiser with a lid, heat 2 tablespoons of olive oil over medium-high heat. Add the garlic and red pepper flakes, cook, stirring, for 30 seconds. Add the tomatoes, a pinch of salt, and ¼ cup basil. Cook with the lid off for about 5 minutes, stirring frequently, then add about ½ cup of the pasta cooking water, cover the pan, reduce the heat to medium, and cook for 5 – 10 minutes or until the tomatoes are soft and saucy. Add the penne to the sauce with more pasta water as needed and cook, stirring occasionally, for another minute or two or until the penne is cooked to your liking. Stir in ¾ cup Parmesan. Taste and add salt if needed.
Serve with a drizzle of olive oil, more cheese, and fresh basil.