Preheat your oven to 400°F (200°C). Arrange the squash chunks on a baking sheet, drizzle with a tablespoon of olive oil, and toss to coat evenly. Roast in the oven for about 25-30 minutes until the squash is golden and tender when pierced with a fork.
Once roasted, transfer the squash to a large pot. Add the remaining olive oil to the pot and warm it over medium heat. Stir in ground cinnamon and smoked paprika, cooking until fragrant and the spices deepen in color, about 1 minute.
Add the roasted squash to the spiced aromatics in the pot. Pour in the vegetable broth, bringing everything to a gentle simmer. Let it cook for about 10 minutes, allowing the flavors to meld and the squash to soften further.
Use an immersion blender directly in the pot or carefully transfer the mixture to a blender in batches. Puree until smooth and creamy, with no visible chunks. Return the blended soup to a gentle simmer.
Stir in the coconut milk to add richness and a subtle sweetness. Season to taste with salt and pepper. Continue to simmer for another 5 minutes, stirring occasionally, until heated through and slightly thickened.
Check the seasoning and adjust if necessary. Ladle the soup into bowls, then garnish with fresh herbs or a swirl of cream for presentation. Serve hot and enjoy the comforting, smoky flavors.