Roast Squash & Aromatics: Preheat oven to 400°F (200°C). Place cubed butternut squash, chopped apple, onion, and smashed garlic cloves on a large parchment-lined rimmed baking sheet. Drizzle with 2 tablespoons olive oil, season with salt, pepper, cinnamon, and nutmeg. Toss thoroughly and spread into a single layer. Roast for 25 to 30 minutes until squash is fork-tender and caramelized at the edges.

Crisp Sage Leaves: While vegetables roast, heat the remaining 1 tablespoon olive oil in a small skillet over medium heat. Add the fresh sage leaves in a single layer and fry for 20 to 30 seconds until crisp and fragrant. Transfer immediately to a paper towel-lined plate and sprinkle with a pinch of flaky salt.

Simmer in Dutch Oven: Transfer the hot roasted squash, apple, onion, and garlic directly into a large Dutch oven or soup pot over medium heat. Pour in 4 cups of vegetable broth, scraping up any caramelized bits from the bottom of the pot. Bring to a gentle simmer for 5 minutes to meld flavors.

Puree Until Velvety: Use an immersion hand blender directly in the pot to puree the soup until completely smooth, silky, and vibrant orange. (Alternatively, blend in batches in a high-speed blender with the center lid cap vented).

Stir in Cream & Finish: Stir in 1/2 cup heavy cream. Warm through gently over low heat for 2 to 3 minutes (do not boil). Taste and adjust seasoning with additional salt, pepper, or a pinch of nutmeg if desired.

Garnish & Serve: Ladle warm soup into deep bowls. Drizzle with a swirl of heavy cream and extra virgin olive oil. Top with crispy fried sage leaves and toasted crunchy pepitas. Serve hot with crusty sourdough bread!