Preheat your oven to 400°F (200°C). Toss the halved cherry tomatoes with 2 tablespoons of olive oil, salt, and pepper. Spread them out on a baking sheet in a single layer. Roast for about 15-18 minutes until soft and caramelized. Set aside.
While the tomatoes are roasting, bring a large pot of salted water to a boil. Add the 12 oz cheese tortellini and cook 3-5 minutes until tender but al dente. Drain, reserving 1/2 cup pasta water.
In a large skillet over medium heat, combine 1/2 cup basil pesto and 1/2 cup heavy cream. Stir and warm through until slightly thickened. Add 1/4 cup grated Parmesan cheese and stir until melted and smooth.
Add drained tortellini to the skillet with the creamy pesto sauce. Toss to coat. If sauce is too thick, add reserved pasta water to loosen. Fold in roasted cherry tomatoes carefully.
Plate the creamy pesto tortellini and garnish with fresh basil leaves. Optionally, sprinkle extra Parmesan cheese. Serve immediately while warm.
