• Preheat oven to 400°F. Line a baking sheet with parchment paper and set aside.
• Peel and cube the squash, removing any seeds. Add the squash cubes to a large bowl. Toss with 1 tablespoon of olive oil, salt, pepper, dried herbs, and nutmeg. Add the seasoned squash pieces to the prepared baking sheet, making sure the squash is in a single layer.
• Roast squash for 20-30 minutes, stirring half-way through. The squash is done when you can just pierce it with a fork. Remove from oven and set aside.
• While the squash is cooking, add the Italian sausage, onion, carrot, and celery to a large soup pot over medium heat. Cook until the sausage is crumbled and cooked through, and the vegetables start to soften, about 10 minutes.
• Add the garlic and cook until garlic becomes fragrant, about a minute.
• Add the sherry and stir, scraping up any of the delicious fond (the browned bits) from the bottom of the pot.
• Add potatoes and chicken stock. Increase heat to high and bring the soup to a boil, then reduce to medium low and cook, at a gentle bubbling simmer, for 8-10 minutes or until the potatoes are cooked.
• Add the cooked squash, heavy cream, and chopped spinach, and stir until the cream has heated and the spinach has wilted, just a few minutes. Optionally, you can use a potato masher and mash some of the squash and potato in the pot, to create a more rustic soup.
• Taste and add salt and pepper if necessary.

Optional Garnish

• To make the optional crispy sage leaf garnish, heat 1 tablespoon of olive oil into a small skillet and fry the sage leaves until crispy. Let cool slightly and crumble over soup.