Preheat your oven to 400°F. Trim the stem and hard bottom end off the butternut squash, then cut it in half lengthwise. Use a spoon to scoop out and discard the seeds. Drizzle the squash flesh with olive oil and sprinkle with a pinch of salt, spreading the oil evenly with your hands. Place the squash halves skin side up on a baking sheet and poke several holes in each half. Roast for 40–45 minutes, or until the flesh is fork-tender and the skin looks wrinkly. Flip the squash halves over and let them cool until you can handle them safely.
While the squash is roasting, heat 1 1/2 tablespoons of olive oil over medium heat in a large pot on the stovetop. Add the sliced leeks, diced Granny Smith apple, minced garlic, chopped fresh sage, ground nutmeg, and 1/4 teaspoon of salt to the pot. Cook, stirring occasionally, for 3–5 minutes, until the leeks are soft and fragrant and the apples just begin to soften. I like to take this time to inhale the beautiful aroma from the leeks, apple, and sage mingling together.
Add the vegetable broth to the pot with the sautéed ingredients. Bring the mixture to a boil, then reduce the heat to a simmer and cover the pot. Let it continue to simmer while the butternut squash finishes roasting in the oven. This helps all the flavors meld together nicely.
Once the butternut squash is cool enough to handle, scoop the roasted flesh out of the skin and add it directly to the pot with the simmering soup base. Stir thoroughly to combine all the ingredients. Continue to simmer for a few more minutes to allow the roasted squash flavor to fully infuse the soup. For an extra depth of flavor, I sometimes add just a splash more olive oil at this stage, but that's optional.
Use a ladle to carefully transfer the hot soup into a stand-up blender. Blend on high for about 1 minute, or until the soup is very smooth and creamy with no lumps. If needed, work in batches to avoid overfilling your blender. Return the blended soup to the pot, taste, and adjust seasoning if desired.
Pour the creamy butternut squash soup into bowls. Garnish with freshly cracked black pepper and a pinch of flaky sea salt if desired. Serve hot and enjoy—the soup pairs wonderfully with crusty bread.