Warm a large pot over medium heat. Add the sweet Italian sausage, along with a pinch of kosher salt and pepper. Break the sausage into small pieces with a spoon and cook for 6 to 8 minutes, until browned.

If the pot has no remaining fat, pour in 1 tablespoon olive oil. Add the diced sweet onion, minced garlic, and cubed butternut squash. Season with another pinch of kosher salt and pepper. Cook for 5 to 6 minutes, stirring frequently, until the onion and squash begin to soften.

Mix in 1 tablespoon tomato paste and cook for a few minutes. Pour in the diced fire roasted tomatoes and 4 cups chicken stock, then add the parmesan rind. Bring the soup to a boil, lower the heat, cover the pot, and simmer gently for 15 to 20 minutes, until the butternut squash is tender.

Stir in ¾ cup heavy cream and 3 cups chopped kale or spinach. Add 8 to 12 ounces cheese tortellini and cook for about 5 minutes, until the tortellini is tender. If the broth needs thinning, add up to 1 more cup chicken stock.

Taste the soup and adjust the kosher salt and pepper as needed.

Serve the soup hot, topped with Parmesan cheese and crushed red pepper.