In a large soup pot, add the Italian sausage over medium-high heat. Cook until browned, breaking it up into smaller pieces as it cooks.
Remove the sausage from the soup pot.
Add olive oil and then add the diced shallot. Cook until softened, about 5 minutes.
Add the garlic. Stir and cook another minute or two.
Add the Italian seasoning, butternut squash, and chicken broth.
Bring to a boil, reduce heat to medium, and simmer for 15 minutes.
After the squash is tender, use an immersion blender to puree the mixture. I like to keep some squash chunks, but you can puree to your preference.
Add the tortellini and spinach, and simmer for 4-5 minutes, until the pasta is softened.
Lastly, stir in the half and half and Parmesan, and stir to combine. Serve and enjoy!