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Preheat the oven to 400 degrees F (200 degrees C). Line a baking sheet with parchment paper. Toss butternut squash, onion, and whole garlic with olive oil. Spread out on the prepared baking sheet.
Roast in the preheated oven until tender and slightly caramelized, 25 to 30 minutes.
Place cooked vegetables into the jar of a blender. If ingredients are hot, fill blender no more than halfway full, and hold lid down with a potholder. You may have to work in batches. Add broth, harissa paste, cumin, smoked paprika, and brown sugar. Blend until smooth
Pour blender contents into a stockpot. Bring to a boil, then reduce heat to a simmer. Cook for 10 minutes to allow the flavors to meld. Stir in heavy cream and season with salt and pepper. Ladle into bowls and serve with a swirl of heavy cream, if desired.