Fill a large pot with water, add 1 tablespoon of salt, and bring to a boil.
Mince garlic and measure out herbs while water heats.
Heat olive oil in skillet over medium heat until shimmering.
Add minced garlic and cook for 30 seconds, stirring constantly.
Pour in crushed tomatoes and stir in oregano, basil, red pepper flakes, and sugar.
Simmer sauce gently for 15 minutes, seasoning with salt and pepper to taste.
Add penne to boiling water and cook 10–11 minutes until al dente.
Reserve 1 cup pasta water, then drain pasta (do not rinse).
Combine pasta with marinara in skillet; toss gently to coat evenly.
Stir in fresh basil and sprinkle Parmesan before serving.