Heat oil in large soup pot, add chopped squash and onion. Saute on medium-high heat for 5 minutes, stirring often, until the onion is mostly soft.
Add the chicken broth and spices, bring to boil. Cover and simmer for 10 minutes or until squash is soft.
Meanwhile, add the ground sausage to a hot skillet. Saute until the sausage is fully cooked.
Add the chopped apple and cook for about 1 minute (if needed, add a bit of olive oil to the pan).
Quickly pour the cooking wine into the pan to deglaze it. Use a spatula to loosen the yummy sausage bits in the pan. Remove from heat.
When the squash is soft, use an immersion blender to puree the squash. Or, use a blender to blend the squash and return it to the pan.
Add the sausage, apple, and cooking wine to the squash along with the wild rice and fresh parsley.
Heat for a few minutes until warm, before serving.
Serve with a dollop of Greek yogurt, fresh parsley, and a sprinkle of cinnamon.