Preheat oven to 400°F (200°C). Line a large rimmed baking sheet with parchment paper.

Place cubed butternut squash, quartered onion, and carrot chunks on the baking sheet. Drizzle with 2 tablespoons olive oil, season with 1 teaspoon salt and ½ teaspoon black pepper, and toss to coat evenly.

Place the prepared head of garlic onto a sheet of aluminum foil, drizzle with 1 teaspoon olive oil, wrap tightly into a packet, and place onto the baking sheet alongside the vegetables.

Roast for 35 to 40 minutes, flipping vegetables once halfway through, until squash is deeply caramelized and fork-tender, and garlic cloves are soft, golden, and fragrant.

Transfer roasted squash, onion, and carrots into a large Dutch oven or soup pot over medium heat.

Carefully unwrap the roasted garlic and squeeze the caramelized soft cloves out of their skins directly into the pot (discard outer papery skins).

Add the vegetable broth, chopped sage, maple syrup, ground cinnamon, nutmeg, and smoked paprika. Stir well and bring to a gentle simmer for 10 minutes to allow the flavors to marry.

Remove pot from heat. Use a high-powered immersion blender to puree the soup directly in the pot until completely smooth, silky, and uniform. (Alternatively, blend in batches in an upright countertop blender, venting the lid with a towel to prevent steam buildup).

Stir in the ½ cup coconut milk (or heavy cream). Taste and adjust seasoning with additional sea salt or black pepper if needed. Warm over low heat for 2 minutes.

Quickly flash-fry whole fresh sage leaves in 1 tablespoon hot olive oil for 30 seconds until crackly and crisp; drain on paper towels.

Ladle hot soup into wide shallow bowls. Drizzle with an artistic swirl of coconut cream, scatter toasted crunchy pepitas over the center, and crown with crispy sage leaves. Serve with warm crusty bread!