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Prepare vegetables: peel squash and cut into 1-2 inch cubes. Cut heads of carrots off and slice into 1/2-inch thick pieces. Peel onion and slice into pieces.
Cook: Add all of the ingredients (except coconut milk) to slow cooker/crockpot - vegetable broth, onion, squash, carrots, pumpkin puree, sugar, cinnamon, nutmeg, pinch of cayenne, and salt & pepper. Mix ingredients together. Set slow cooker time for 5 hours on LOW or 3 hours on HIGH.
Puree soup: after soup has cooked, use a hand-immersion blender or high-powered blender to blend soup until creamy and smooth.
Season to taste and serve: before serving soup, taste it and adjust with salt & back pepper or additional spice if desired. Stir in 1/2 cup coconut milk and then serve with pumpkin seeds, cracked black pepper, and a sprinkle of coconut sugar if desired.