Prep oven & pan: Preheat oven to 400°F (200°C) and line a large rimmed baking sheet with parchment paper.

Roast to caramelized tenderness: Place halved butternut squash cut-side up on the sheet. Rub flesh with 1 tablespoon olive oil, salt, and pepper. Arrange chopped apples, shallots, and garlic cloves around the squash and drizzle with remaining oil. Flip squash halves cut-side down. Roast for 35 to 40 minutes until squash skin is blistered and flesh is fork-tender and deeply caramelized.

Scoop & simmer: Once cool enough to handle, scoop tender squash flesh out of the skins directly into a large Dutch oven or soup pot. Add roasted apple, shallots, garlic, and vegetable broth. Bring to a gentle simmer over medium heat for 5 minutes to marry flavors.

Puree until velvety: Use an immersion stick blender directly in the pot (or carefully transfer in batches to a high-speed blender) and blend for 2 full minutes until the soup is completely smooth, glossy, and lump-free.

Finish with cream & spices: Stir in heavy cream, pure maple syrup, freshly grated nutmeg, ground cinnamon, and a pinch of cayenne. Simmer gently on low for 2 minutes. Taste and adjust salt and pepper as needed.

Flash-fry sage: Heat 1 tablespoon olive oil in a small skillet over medium-high heat. Drop in fresh sage leaves and fry for 20 to 30 seconds until dark green and crisp; transfer to paper towels.

Ladle & enjoy: Ladle warm soup into shallow bowls. Swirl an extra tablespoon of cream over the surface, top with crispy fried sage leaves, toasted pepitas, and cracked black pepper. Serve immediately with warm crusty sourdough bread for dipping!