Preheat the oven to 375°F (190°C). Line a large baking sheet with parchment paper.
Place the cubed butternut squash in a large bowl. Add the olive oil, Italian seasoning, cumin, black pepper, and salt. Toss until the squash is evenly coated.
Spread the squash in a single layer on the prepared baking sheet. Roast for about 30 minutes, or until tender and lightly caramelized around the edges.
Meanwhile, cook the penne according to the package directions. Drain and set aside.
Add the diced onion, minced garlic, and broth to a large skillet. Bring to a gentle simmer over medium heat and cook for about 5 minutes.
Add the sliced beef smoked sausage and cook for approximately 8–10 minutes, stirring occasionally, until heated through and lightly browned. Transfer the sausage and onion mixture to a bowl.
Pour the heavy whipping cream into the same skillet. Heat gently, whisking frequently, until it reaches a light simmer. Avoid aggressively boiling the cream.
Add the Parmesan and stir until completely melted and the sauce becomes smooth and creamy.
Add the spinach, sausage mixture, roasted butternut squash, and cooked pasta. Gently toss until everything is coated in the sauce and the spinach has wilted.
Serve the Creamy Butternut Squash Pasta warm with extra Parmesan or freshly cracked black pepper if desired.