In a medium skillet combine 2 tablespoons olive oil and onion. Sauté over medium heat for 5 minutes.
Add garlic and ginger. Continue cooking over medium heat for 2 minutes.
Lastly, add salt, cayenne, cinnamon, coconut milk, and broth. Stir to combine ingredients. Cover skillet with a lid, reduce heat to low, and let ingredients simmer for 5 minutes.
Once squash is done cooking, remove as much flesh as you can and discard the skin.
Add half of the squash and half of the coconut milk mixture to the bowl of a large food processor. Process for 2-3 minutes, or until contents are completely smooth. Pour soup into a large pot over low heat.
Repeat above step with the remaining squash and coconut milk mixture.
Stir ingredients in the pot to ensure even mixing. Serve soup immediately with a drizzle of coconut milk and fresh cilantro.