Traditional pasta puttanesca is made with a tomato sauce, but this version is made with a much thinner “sauce” of roasted cherry tomatoes that clings to the starchy pasta after you toss it all together. It's a perfect celebration of summer tomatoes.
Preheat your oven to 400 degrees F, and bring a large pot of salted water to a boil for the spaghetti. On a baking sheet lined with parchment paper, drizzle the cherry tomatoes with 2 tablespoons of extra virgin olive oil, and season with salt and pepper. Transfer to your preheated oven and roast for 15 to 20 minutes.
Meanwhile, heat a large skillet (large enough to toss all your pasta in) over medium heat. Add the remaining 3 tablespoons of extra virgin olive oil, along with the garlic and anchovies. Cook for 3-4 minutes, until the anchovies have melted into the oil and the garlic is fragrant.
By now, your water should be boiling. Add the spaghetti and cook according to package instructions, shaving off 1 minute of cooking time (i.e. the pasta should be just under “al dente.”) Reserve at least 1 cup of the pasta cooking water.
To the garlic and anchovies, add the the olives, capers, red pepper flakes, and tomatoes. Toss in the pasta, and toss everything together for a minute, allowing the pasta to absorb the liquid in the pan. If it starts to look dry, add 1/3 cup of pasta water (or more as needed) to give it a silky texture. Continue tossing, and the pasta will absorb the additional liquid. Toss in the herbs, and serve with Parmesan cheese.