Preheat your oven to 400°F (200°C). Spread the butternut squash chunks on a baking sheet, drizzle with olive oil, and toss to coat evenly. Roast until golden and tender, about 25-30 minutes.
While the squash is roasting, heat a bit of olive oil in a large pot over medium heat. Add the chopped onion and sauté until soft and translucent, about 5 minutes, until it begins to turn golden.
Add the minced garlic to the onions and cook for another minute until fragrant, hearing the aroma release.
Once the roasted squash is ready, add it to the pot with the sautéed onions and garlic. Pour in the vegetable broth and stir to combine.
Bring the mixture to a gentle simmer, then add cinnamon, salt, and pepper. Let it simmer uncovered for about 10 minutes to allow flavors to meld.
Use an immersion blender directly in the pot, or transfer the soup in batches to a blender. Puree until silky smooth and uniform in texture.
Return the blended soup to the stove on low heat. Stir in a tablespoon of olive oil or butter for added richness and adjust seasoning as needed.
Cook for another 2-3 minutes until warmed through and slightly glossy, then remove from heat.
Serve the soup hot, garnished with a drizzle of olive oil, a sprinkle of pepper, or a swirl of cream if desired. Enjoy the velvety, flavorful dish.