Preheat the oven to 400F.
On a sheet pan, lay out all listed ingredients apart from the vegetable broth. Sprinkle it with salt and pepper.
Place in the preheated oven, and roast for 40 minutes, until the squash is soft.
When safe to handle, carefully transfer the contents of the sheet pan to a high speed blender, along with two cups of vegetable broth of water. Combine until a smooth soup is formed.
Pour into bowls, and garnish with coconut milk, red pepper flakes and olive oil, as desired.