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1
Preheat oven to 400u00b0F.
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2
Cut butternut squash in half lengthwise and scoop out seeds and stringy bits. Pour olive oil in the cavity of each squash half. Slice top off the heads of garlic. Place each one, cut side down, in one of the squash cavities.
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3
Place squash and garlic, cut side up, in a large rimmed roasting pan. Pour about 2 cups of water in the bottom of the pan. Bake in preheated oven until squash is fork tender, about 60-70 minutes. Remove from oven, pull garlic heads out of the squash, and allow to cool for a few minutes.
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4
Meanwhile, as squash is baking, brown and crumble sausage in a large soup pot. Remove to a plate.
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5
Bring a medium pot of water to a boil. Cook tortelloni according to package instructions. Remove with a slotted spoon to a plate.
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6
When squash has cooled a bit, scoop out the flesh into the now-empty soup pot. Squeeze out cloves of garlic into the pot as well. Add basil, oregano, thyme, and chicken broth. Heat until warm. Puree with a stick blender until completely smooth.
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7
Heat until nearly boiling. Add spinach, cover, and cook for 2 minutes. Remove from heat and add cream, sausage, and tortelloni. Give it a good stir. Taste and add salt and pepper if needed.
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8
Serve hot with freshly grated Parmesan cheese.
