Preheat oven to 350. In a large bowl, mix together olive oil and Tuscan Seasoning. Add Butternut Squash and toss to coat.
Spread Butternut Squash evenly onto a roasting pan and roast for 35-40 minutes, turning once half way through.
Add the Butternut Squash and about 1/2-3/4 of the vegetable stock to a large pot and bring to a boil, then reduce to a simmer for about 5 minutes until the squash is completely soft.
Add the pinch of cinnamon, salt and pepper. Then, with an immersion blender, (or add the mixture to a regular blender) blend the squash and vegetable stock until creamy. Add about 1/4 cup of the heavy cream and check the texture. Depending on how thick or thin you would like your soup, you may want to add more stock and blend again. I also added a bit more heavy cream to make my soup creamier. Be sure to add a little of the hot soup to your cream first so that it does not curdle from the heat of the soup.
When you've achieved your desired texture, serve in a bowl, garnished with a sprinkle of parmesan cheese, pumpkin seeds and dried cranberries.