Preheat oven to 400 degrees. Slice butternut squash in half lengthwise and scoop out seeds and pulp. Brush with olive oil and lay squash flat side down on a baking sheet. Bake for 40 minutes.
Remove roasted squash from oven and let cool for 5-10 minutes before peeling skin.
In a large pot, bring peeled butternut squash, vegetable broth, coconut milk, sugar, salt, pepper, paprika, and cinnamon.
Use an immersion blender or food processor to puree soup.
Serve with sour cream, chopped cilantro and coconut flakes.