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Tags and nutritional info are auto-generated and may be inaccurate. Always check the full ingredient list before cooking.
Preheat the oven to 400F (200C) and line a baking sheet with parchment paper. Halve the butternut squash, brush the cut sides with olive oil and season generously with salt and pepper.

On a small piece of foil, add the shallot and garlic cloves, drizzle with olive oil, sprinkle with salt and pepper and wrap tightly. Place on the same tray. Roast for 45-75 minutes, removing the foil packet after about 45 minutes. The squash should be tender enough to pierce easily with a fork.
Scoop the roasted squash into a Dutch oven. Add the roasted garlic and shallot, 4 cups chicken stock, the cinnamon and the rosemary leaves. Blend with an immersion blender until smooth.

Place the Dutch oven on the stove and heat through over medium-low heat.
Add more chicken stock 1/2 cup at a time until the soup reaches the desired consistency. It should be slightly thick.
Taste and adjust cinnamon and salt to your preference.
Cook the ground Italian sausage in a dry skillet over medium heat until browned and crisp at the edges, 8-10 minutes. Break into small crumbles and set aside.

Finely mince half an apple. In a small skillet over medium heat, add the apple, cinnamon, ginger, nutmeg and a pinch of salt. Saute 3-4 minutes until the apples soften slightly. Remove from heat and let cool.

Ladle the soup into bowls. Top each with a spoonful of crumbled sausage and a scoop of apple relish. Finish with toasted pepitas and a drizzle of olive oil.
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For deeper flavor, use homemade chicken stock.
Use extra cinnamon to deepen the fall flavor.
Have plenty of stock on hand to thin the soup - how much you need hinges on the size of your squash.
The squash can be roasted up to 2 days ahead.
Substitutions: use vegetable stock and skip the sausage to make it vegetarian; swap turkey or chicken sausage for a lighter flavor; use pear instead of apple for a sweeter relish.
Can I make this soup vegetarian?
Yes, use vegetable stock and skip the sausage to make it vegetarian.
How can I store the soup?
Store the soup up to 4 days refrigerated or 3 months frozen. Reheat gently, thinning with more stock or water, then add the toppings fresh.
Can I prepare the squash in advance?
Yes, the squash can be roasted up to 2 days ahead.
What can I use instead of apple for the relish?
You can use pear instead of apple for a sweeter relish.
How do I adjust the soup's consistency?
Add more chicken stock 1/2 cup at a time until the soup reaches the desired consistency.

