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

Spread cubed butternut squash, apple wedges, onion, and garlic cloves across the baking sheet. Drizzle with 2 tablespoons olive oil and season with salt and pepper. Toss to coat evenly. Roast for 30 to 35 minutes, stirring once halfway through, until squash is fork-tender with golden caramelized browned edges.

Transfer roasted squash, apple, onion, and soft roasted garlic into a large heavy Dutch oven. Pour in broth, nutmeg, cinnamon, smoked paprika, and maple syrup. Bring to a gentle simmer over medium heat for 5 minutes to meld the flavors.

Using an immersion hand blender directly in the pot (or working in batches in a high-speed countertop blender), puree the soup on high speed for 2 minutes until luxuriously smooth and velvety. Stir in heavy cream (or coconut milk) and adjust salt and pepper to taste.

In a small skillet over medium heat, heat 1 tablespoon olive oil. Add sage leaves and fry for 30 to 45 seconds until crispy and dark green; drain on paper towels. In the same hot oil, add pumpkin seeds and a pinch of smoked paprika and salt. Toast for 2 minutes until seeds pop and turn golden.

Ladle steaming soup into warm shallow bowls. Swirl with extra cream, top with a generous mound of crunchy toasted pepitas and crispy fried sage, and serve with thick toasted sourdough bread!