Heat your oven to 400 degrees. On a baking sheet lined with parchment paper, add your halved tomatoes. Season with 2 tablespoons of extra-virgin olive oil, salt and pepper. Roast for 30 to 40 minutes, until jammy and burst.
In the meantime, in a large saucepan, heat your remaining 2 tablespoons of olive oil over medium heat. Once hot, add in your shallots, salt, pepper, and a pinch of chili flakes. Stir to sweat until your shallots are softened, about 1 to 2 minutes. Add in your minced garlic, tossing to combine for another 30 seconds, until fragrant.
Add in your crushed tomatoes, and bring the heat to medium-low. Once your tomatoes are ready from the oven, add them to the pot, and give them a little crush if needed. Tear your basil leaves and add that in, stir to combine.
Simmer your sauce for 30 minutes, and up to 1 hour on low.
When ready to serve, cook your pasta until al dente. Then transfer the pasta to the sauce, using pasta water as needed to toss. Add in basil leaves, and finish with parmesan. Optional to add a knob of butter melted through.
Serve in bowl, topping with more parmesan, and basil leaves.
Notes
Prepping: You can make the sauce up to two days in advance. Store it in the refrigerator in an airtight container and reheat gently before tossing it with pasta.
Storing: Store in an airtight container in the fridge for up to four days.
Tomato Variations: San Marzano tomatoes are the classic Pomodoro tomatoes choice, especially when they’re in season during late summer. When those are not available, Roma tomatoes and plum tomatoes are excellent alternatives.