Preheat oven to 400°Fahrenheit (200°Celsius). On a large baking sheet, toss the cubed butternut squash with 1 tablespoon olive oil and a generous pinch of salt. Roast for 30–35 minutes until tender and lightly golden.

In a large pot or Dutch oven, heat 1 tablespoon olive oil over medium heat. Add the diced onion, shallot, and garlic. Cook for 3–4 minutes until soft and fragrant. Add sage leaves and sauté for 1 more minute.

Pour in the white wine and let it simmer for 2–3 minutes, scraping up any browned bits from the bottom of the pot.

Add the roasted squash, chicken broth, Parmesan rind, salt, and pepper. Bring to a boil, then lower the heat and simmer for 10 minutes to let flavors meld.

Remove the Parmesan rind. Use an immersion blender to blend the soup right in the pot, or transfer to a blender in batches. Blend until mostly smooth — we want it velvety, not too thick.

Stir in the heavy cream and butter. Taste and adjust salt and pepper as needed.

Ladle into bowls and top with crispy sage, a drizzle of brown butter or olive oil, and toasted pepitas.