Preheat your oven to 400º.
Wash the skin of the squash and trim the ends to create a flat surface. Stand the squash on one trimmed end and carefully cut in half lengthwise.
Lay the squash cut side down on a large baking sheet. Add water to the bottom of the pan, enough to allow the squash to sit in a shallow pool and lightly brush the skin of the squash with 1 tbsp safflower oil. Roast for 40-45 minutes until easily pierced with a fork. Set aside to cool.
Heat up a large stockpot. When hot, add the coconut oil and heat until shimmering. Add the shallots and salt. Sauté on medium-low heat until the shallots are golden-brown. About 12-15 minutes. Add the garlic and sauté for 1-2 minutes more.
Add the coconut milk, ½ quart of vegetable broth, unsweetened applesauce, maple syrup, cinnamon and nutmeg. Stir to combine and bring to a simmer. About 15 minutes.
When the squash is cool enough to handle, remove the seeds with a spoon and discard. Then, scoop the meat out of the skin and add it to the broth. Using an immersion blender, blend the soup until it is smooth. If you are using a standard standing blender, carefully blend the soup in small batches. The thickness of will vary based on the size of the squashes you use. I recommend starting with ½ quart of vegetable broth. If the soup is too thick, you can add more of the vegetable broth.
To make the crispy sage, heat up 1 tbsp of safflower oil in a small frying pan. When hot, add the sage leaves and allow to crisp. Keep a careful eye on the leaves, they will become crispy in 1-2 minutes. When crispy, remove the leaves with a slotted spoon allow them to cool on a paper towel.
Serve the soup with a spoonful of toasted pepitas, crispy sage and salt and pepper to taste.