1️⃣ Preheat oven to 425F. In a large baking dish, add the tomatoes, onion, garlic, and oregano. Drizzle with the olive oil and sprinkle with 1 tsp of the salt, along with the pepper and sugar. Toss to evenly coat. Arrange the tomatoes cut side up and roast for about 1 hour, until very soft and caramelized around the edges. When the tomatoes are nearly done, bring a large pot of generously salted water to a boil.
2️⃣ Transfer the roasted tomatoes, onion, and garlic, including all the juices, to a blender. Add the crushed Calabrian chilis and blend until smooth. Taste and add more chilis if you’d like it spicier.
3️⃣ Pour the sauce into a large skillet over medium-low heat. Stir in the milk or cream and remaining 1/2 tsp kosher salt and gently simmer, stirring often, for 5–7 minutes until thickened and silky. Remove from the heat until the pasta is ready.
4️⃣ Cook pasta until before it’s al dente, 2 mins less than package directions, reserving 1 cup of pasta water before draining.
5️⃣ Add the cooked pasta to the sauce and cook over medium heat, tossing to coat the pasta in the sauce for 2-3 mins until the sauce clings to the pasta. Loosen the sauce with reserved pasta water as needed. Turn off the heat and stir in the grated parmesan. Taste and add more salt if desired.
6️⃣ Serve with fresh basil and plenty of grated parmesan. Enjoy!
