Heat a large high sided skillet or dutch oven over medium heat. Add ¼ cup olive oil, once hot add the onion. Cook until fragrant and begins to turn translucent, about 2 minutes.
Add the garlic, Italian seasonings, and chili flakes (if using), stir, and cook for 30 seconds.
Add the tomatoes, salt, and pepper. Stir and cook until the tomatoes start to soften, about 2 minutes.
Add the pasta, water, and chicken stock. Bring the liquid to a boil over high heat. Cook and stir frequently, until the pasta is tender and water has mostly evaporated, keeping a small amount in the pan to create a light sauce, about 10 to 12 minutes. Add more water if needed, ½ cup at a time for a softer pasta. Turn off the heat.
Add parmesan cheese and basil, stir to combine. Drizzle pasta with a little extra-virgin olive oil.
Taste and season with more salt and pepper as desired.
Garnish with more cheese, basil, and black pepper. Divide among plates and serve warm.