Roast the Squash: Preheat your oven to 400°F (200°C). Spread the butternut squash cubes on a baking sheet, drizzle with olive oil, and sprinkle with salt and pepper. Roast for 25-30 minutes, or until the squash is tender and lightly caramelized.
Sauté the Vegetables: While the squash roasts, heat olive oil in a large pot over medium heat. Add the onion and carrot, and sauté for about 5 minutes, until softened. Add garlic and sauté for an additional 2 minutes until fragrant.
Simmer the Soup: Once the squash is roasted, add it to the pot with the sautéed vegetables. Pour in the vegetable broth and bring to a simmer. Add thyme and cinnamon. Let it cook for 10 minutes, allowing the flavors to meld.
Blend the Soup: Remove the thyme sprigs. Use an immersion blender to puree the soup until smooth and velvety. (Alternatively, transfer to a blender in batches).
Finish the Soup: Stir in the coconut milk, and adjust seasoning with salt and pepper. Let the soup heat through for a few minutes before serving.