Preheat your oven to 400°F (200°C). On a baking sheet, toss the halved cherry tomatoes with 2 tablespoons of olive oil, minced garlic, salt, and pepper. Spread them out in a single layer and roast for 20-25 minutes until the tomatoes are soft and starting to caramelize.
Meanwhile, bring a large pot of salted water to a boil. Cook the penne according to the package instructions until al dente, usually around 10-12 minutes. Reserve about ½ cup of the pasta cooking water and then drain the pasta.
In a large skillet over medium heat, warm the remaining 1 tablespoon of olive oil. Pour in the heavy cream and bring it to a gentle simmer. Stir in the grated Parmesan cheese until melted and smooth, creating a luscious sauce. If the sauce is too thick, slowly add a splash of the reserved pasta water to loosen it up.
Add the roasted tomatoes (along with all their juices) and cooked penne into the skillet with the cream sauce. Toss everything gently to coat the pasta evenly. Stir in the chopped fresh basil and sprinkle with red pepper flakes, if using. Taste and adjust seasoning with additional salt or pepper as needed.
Serve immediately with an extra sprinkle of Parmesan and basil on top. This dish pairs beautifully with a simple green salad or garlic bread for a complete meal.
