Cut squash in half and scoop out the seeds and loose fiber. Place on a baking sheet. Sprinkle with coarse salt, fresh ground black pepper, and drizzle with olive oil.
Place the cut apples in a roasting pan and sprinkle with sea salt, black pepper, garam masala, and a drizzle of olive oil. Roast both in a hot oven 390° until soft (apples will take shorter). Scoop out soft squash flesh and add to a pan along with the apple.
Add 1 cup stock and puree with hand-held blender. Add 1 cup stock and puree with hand-held blender until smooth and liquid. Taste, adjust seasoning and serve!