Preheat the oven: Preheat your oven to 400°F (200°C).
Prepare the squash: Peel and cut the butternut squash into evenly sized cubes. Place the squash and garlic cloves on a large baking sheet.
Season: Drizzle with olive oil and sprinkle with Italian seasoning, salt, and black pepper. Toss until evenly coated.
Roast: Roast for 25–35 minutes, or until the squash is fork-tender and lightly browned around the edges.
Cook the pasta: Bring a large pot of salted water to a boil. Cook the pasta according to the package directions until al dente.
Reserve pasta water: Before draining, reserve about 1/2 cup of pasta water. Drain the pasta and set aside.
Blend the sauce: Add the roasted squash and garlic to a blender. Add vegetable broth, heavy cream, Parmesan cheese, nutmeg, and black pepper. Blend until smooth and creamy.
Warm the sauce: Pour the sauce into a large skillet over medium-low heat. Warm gently for several minutes, stirring occasionally.
Combine: Add the cooked pasta and toss until thoroughly coated in the creamy squash sauce.
Adjust the consistency: Add reserved pasta water, one tablespoon at a time, if the sauce is too thick.
Serve: Taste and adjust the seasoning. Garnish with fresh parsley, extra Parmesan, and cracked black pepper before serving.