Boil the pasta: Bring a large pot of salted water to a boil. Cook penne until just shy of al dente according to package directions.
Reserve 1 cup of the starchy water, then drain.
Sauté the aromatics: While the pasta cooks, heat olive oil in a wide skillet over medium heat. Add onion and a pinch of salt. Cook 4–5 minutes until soft and translucent, stirring occasionally.
Add garlic and spice: Stir in garlic, red pepper flakes, and oregano.
Cook 30–60 seconds until fragrant. Don’t let the garlic brown.
Build the sauce: Pour in crushed tomatoes. Add sugar if your tomatoes are very tangy.
Season with salt and pepper. Simmer 6–8 minutes, stirring now and then, until slightly thickened.
Make it creamy: Lower the heat and stir in heavy cream. Simmer 2 minutes more.
If using, swirl in butter for extra richness.
Cheese and basil: Stir in Parmesan until melted and smooth. Fold in most of the basil, saving a little for garnish. Taste and adjust salt, pepper, and heat level.
Toss with penne: Add the drained pasta to the skillet.
Splash in a bit of reserved pasta water to loosen and help the sauce cling. Toss over low heat for 1–2 minutes until glossy and well-coated.
Finish and serve: Top with extra Parmesan and the remaining basil. Add a crack of black pepper and a drizzle of olive oil if you like.