Preheat your oven to 400°F (200°C) and line a large rimmed baking sheet with parchment paper. Arrange the cubed butternut squash, diced Honeycrisp apple, shallot halves, and smashed garlic cloves in a single uncrowded layer.

Drizzle generously with 3 tablespoons of olive oil, 1/2 teaspoon kosher salt, and freshly cracked black pepper. Toss with clean hands until every piece is evenly coated.

Roast at 400°F (200°C) for 30 to 35 minutes, stirring once halfway through, until the squash cubes are completely fork-tender with golden-brown caramelized blistered edges.

Transfer the roasted caramelized squash, apples, shallots, and garlic directly into a large heavy Dutch oven or stockpot over medium heat.

Pour in 4 cups of vegetable or chicken bone broth, pure maple syrup, freshly grated nutmeg, and remaining 1/2 teaspoon kosher salt. Bring to a gentle boil, then reduce heat to low, cover with lid, and simmer for 10 minutes to marry the flavors.

Remove from heat. Using a high-powered immersion hand blender, blend the soup in deep swirling motions for 2 to 3 minutes until completely uniform, luminous, and velvety-smooth with zero lumps (alternatively, blend in batches in a high-speed countertop blender with the lid vented).

Stir in 1/2 cup of heavy cream (or coconut milk). Taste and adjust seasoning with an extra pinch of flaky salt or cracked black pepper as desired.

In a small skillet, melt 2 tablespoons of butter over medium heat. Once foaming, drop in whole fresh sage leaves and fry for 30 to 45 seconds until crisp and translucent (do not burn). Transfer sage with a slotted spoon to a paper towel; immediately sprinkle with a pinch of salt.

In the same fragrant sage-infused skillet, toast the raw pumpkin seeds for 2 minutes until puffed, fragrant, and lightly browned.

Ladle the steaming velvety soup into warm shallow bowls. Swirl an extra tablespoon of heavy cream across the surface, crown with crispy fried sage leaves and toasted crunchy pepitas, and serve hot with warm crusty bread!