Preheat oven to 400 degrees.
Place cubed honeynut squash on a parchment lined baking sheet. Dizzle with olive oil and season with a pinch of sea salt and freshly cracked pepper. Bake for 25 minutes, or until squash is fork tender. Remove from oven and allow to slightly cool.
Meanwhile, boil pasta according to package instructions. Be sure to reserve 1/2 cup of the water the pasta is cooking in.
In a large saute pan set over medium heat, add ground sausage, breaking in to bite sized pieces as it cooks. Once sausage is completely cooked, remove with a slotted spoon and set aside.
Add stemmed and torn kale to the pan, tossing to coat completely with the redisual grease from the sausage. Season lightly with salt and pepper, starting with a pinch, but ultimately using 1/4 teaspoon as salt if it's needed. The sausage will already be salty in the total dish, so adjust to your taste.
Once pasta is done, return to pot it cooked in. Add honeynut squash, sausage, and sauteed kale, tossing to combine. Add grated parmesan cheese, followed by 1/4 cup of the reserved pasta water. Mix to combine, adding additional water as needed. Taste pasta, adjust salt and pepper to your liking.
Serve with shaved parmesan and chopped herbs.