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Preheat oven to 400°F. Place squash cubes on sheet pan and toss with 2 tbsp olive oil. Bake for 30-40 minutes or until tender. (Note: The squash can be cooked and cooled overnight in advance of the soup preparation.)
Use remaining olive oil to cook mirepoix in a medium sized stock pot until tender. Add garlic, salt, pepper and cayenne pepper and sauté an additional 2-3 minutes.
Remove squash from oven. Add squash cubes to pot with vegetables, then add vegetable broth and bring to a boil. Reduce heat, cover and simmer for 30 minutes. Once vegetables are very tender, use an immersion blender or food processor to purée the soup. Add whipping cream to puréed soup, stir to blend and return to heat until ready to serve. Place toppings in small serving bowls and allow guests to garnish their soup as desired.
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Great recipe, the only addition for me would be some fresh sage.