Preheat the oven to 400°F (200°C). Spread the cubed butternut squash on a baking sheet, drizzle with olive oil, and season with salt and pepper. Roast for 25-30 minutes until tender.

In a large pot, heat a tablespoon of olive oil over medium heat. Add the chopped onion, carrot, and celery. Sauté for about 5 minutes until softened. Add the minced garlic and cook for another minute.

Add the roasted butternut squash, vegetable broth, ground cumin, ground cinnamon, salt, and pepper to the pot. Bring to a boil, then reduce heat and let it simmer for 15 minutes.

Using an immersion blender or a regular blender, puree the soup until smooth. Stir in the coconut milk and heat through.

Ladle the soup into bowls and garnish with toasted pumpkin seeds and chopped cilantro. Serve warm.