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Preheat your oven to 425 degrees F. Line a rimmed baking sheet with parchment paper.
Wash your squash, cut off each end and slice the squash vertically down the center. (Use a sharp knife to make the process easier and safer) A sharp knife is a safer one. Use an ice-cream scoop or a spoon to scoop the seeds and flesh out of the squash. Rub olive oil on the interior or the squash and lightly sprinkle salt and pepper.
Place the squash face down on the parchment paper. Roast for 40 or so minutes. You want the flesh to be soft and tender and the skin to be brown and caramelized.
In a soup pot or skillet (skillet- if you are using a Vitamix that warms the soup up for you) Add in one tablespoon of olive oil over medium/high heat. Add the chopped onion, garlic, and shallot. Saute 3-4 minutes, or until the onions are translucent and everything is soft with slight caramelized brown edges. Let cool for a couple of minutes and add to the blender.
Once the butternut squash is ready, let cool a couple of minutes and use a large spoon to scoop flesh into the blender. Discard the browned skin. Add in 1 tsp salt (plus more to taste), fresh ground black pepper, nutmeg, cinnamon, butter, and 2 cups of stock. Add more broth as needed after mixing to get the desired thickness.
If you are using the Vitamix ascend series blender, use the soup setting to blend through and heat about 6 minutes. For all other blenders, mix on highest setting until smooth and creamy. Adjust salt, pepper, and stock as needed.
Serve directly warmed out of the Vitamix or keep warm in a soup pot. Top with optional pumpkin seeds and a drizzle of heavy cream. ENJOY!!
Storage: Let cool to room temperature. You can freeze the soup for up to 3 months or store in fridge for 3 days.