Preheat your oven to 400°F (200°C). Line a baking sheet with parchment paper or lightly grease it to roast the tomatoes evenly without sticking.
Place the halved cherry tomatoes on the prepared baking sheet. Drizzle with olive oil, sprinkle minced garlic, salt, pepper, dried oregano, and red pepper flakes if using. Toss gently to coat. Roast in the preheated oven for 20-25 minutes until tomatoes are soft, caramelized, and bursting with flavor.
While the tomatoes roast, bring a large pot of salted water to a boil. Add the penne pasta and cook according to package instructions until al dente. Drain the pasta and set aside.
In a bowl, combine ricotta cheese, half of the shredded mozzarella, grated Parmesan, and chopped fresh basil. Stir until well blended and fragrant.
In a large mixing bowl, combine the cooked penne pasta with the roasted tomato mixture. Add the cheese and basil blend, folding gently to mix everything thoroughly without mashing the tomatoes.
Pour the pasta mixture into your baking dish. Sprinkle the remaining mozzarella cheese evenly over the top for that irresistible golden crust.
Bake uncovered at 375°F (190°C) for 20-25 minutes until the cheese is melted and bubbly, with slightly browned edges.
Remove from oven and let it cool slightly before serving. Garnish with extra fresh basil leaves for a pop of color and flavor.