Preheat the oven to 400°F (200°C). Toss the diced butternut squash with olive oil, salt, and pepper on a baking sheet. Roast for 20 minutes until tender.

In a large pot, bring salted water to a boil. Add the penne pasta and cook according to package instructions until al dente. Drain and set aside.

In a skillet over medium heat, add the Italian sausage and cook until browned, breaking it apart with a spoon. Add minced garlic, thyme, and sage, cooking for an additional 2 minutes.

Add the roasted squash and cooked pasta to the skillet with the sausage. Toss everything together and cook for another 2-3 minutes. Serve hot, topped with grated parmesan and fresh parsley.