Combine all the ingredients for the sauce base and toss to combine. Season lightly with salt and pepper. Let stand as you prepare the rest of the meal.
Make the pasta:
Bring a large pot of salted water to a boil. Add the pasta and cook until al dente. Remove ½ cup of the water and set aside. Drain the pasta.
Make the sauce:
As you wait for the pasta water to boil, heat 1 tablespoon olive oil in a medium pot over medium heat. Add the cherry tomatoes and a pinch of sugar, salt, and pepper. Bring to a boil. Reduce heat and simmer for 15–20 minutes. Taste and add more salt and pepper.
Prepare the arugula:
Combine the arugula, 8 basil leaves, and olive oil in a bowl. Use your hands to massage the oil into the leaves gently. Add a pinch of salt.
Finish the sauce:
Stir the sauce base into the cherry tomatoes and the torn basil leaves. Bring to a boil for 3–5 minutes until the shallots soften. Reduce the heat and add half the pasta water. Stir in the cooked pasta, adding the remaining pasta water as needed until the pasta is well-coated with the sauce. Taste and add more salt and pepper if needed. Remove from heat.
To serve:
Divide the dressed arugula between shallow bowls and pile the cooked pasta on top. Garnish each plate with freshly grated Parmesan cheese if you like. Enjoy!