Preheat oven to 400°F. Place cubed squash and garlic on a baking pan lined with parchment paper and drizzle with olive oil, then season with salt and pepper. Then toss until the vegetables are coated. Bake until squash is tender and soft, about 35-40 minutes. Allow to sit for 10 minutes.
Using a Dutch oven or soup pot, heat the remaining 2 tablespoons of olive oil over medium heat, and sauté the onions for about 3-4 minutes, until you see the onions are starting to caramelize, then add ginger.
Add the vegetable broth, roasted squash and remove the skins from each garlic before adding it to the soup. Season with salt and pepper. Bring the soup to a low boil, then reduce heat and simmer for about 10 minutes.
Puree soup using a hand emulsifier or blender until the soup in smooth. If you are using a blender, wait until the soup is slightly cooled and pour in small batches at a time to blend. Test if seasoning needs adjusting.
Garnish with fried sage, pumpkin seeds and chili pepper flakes if desired. Enjoy!
