Preheat your oven to 400°F (200°C). Toss the cubed butternut squash and chopped carrots with olive oil, salt, pepper, and ground cinnamon. Spread them in a single layer on a baking sheet lined with parchment paper.
Roast the vegetables in the oven for about 35-40 minutes until they are tender and slightly caramelized around the edges, filling the kitchen with warm, sweet aromas.
Remove the vegetables from the oven and let them cool slightly for easier handling. Transfer them to a blender or food processor, adding the warmed vegetable broth.
Blend until smooth and creamy, adjusting the consistency with more broth if necessary. Taste and add extra salt, pepper, or cinnamon as desired.
Pour the blended soup into a pot and heat over medium-low heat until warmed through, about 5 minutes. Stir in the heavy cream to add richness and a subtle creamy texture.
Give the soup a final stir, taste once more, and adjust seasoning if needed. Ladle into bowls and serve hot, optionally garnished with a drizzle of cream or fresh herbs.