Boil a big pot of salted water. Cook the penne until just al dente.
Scoop out 1/2 cup pasta water. Drain the pasta.
Warm the olive oil in a wide skillet over medium heat.
Stir in garlic and red pepper flakes. Cook until fragrant, about 45 seconds.
Add tomato paste. Cook, stirring, 1 minute to darken slightly.
Pour in the crushed tomatoes. Season with salt and black pepper.
Simmer, stirring occasionally, until thickened, 10 to 12 minutes.
Toss in the drained pasta and a splash of reserved water. Stir until glossy and coated.
Fold in the herbs and half the Parmesan. Adjust salt or heat to taste.
Serve hot with the remaining Parmesan.