Preheat your oven to 400°F (200°C). Spread pumpkin chunks and whole garlic cloves on a baking sheet, then drizzle with olive oil and sprinkle with cinnamon. Roast until the pumpkin is tender and slightly caramelized, about 40 minutes, filling your kitchen with a warm, spicy aroma.
Remove the baking sheet from the oven and let the pumpkin cool slightly. Squeeze the roasted garlic out of its skins into a blender or large mixing bowl.
Add the roasted pumpkin chunks to the blender with the garlic. Pour in the vegetable broth and add smoked paprika for a smoky touch. Blend until completely smooth and creamy, tasting and adjusting salt and pepper as needed.
Pour the soup mixture into a large pot and bring to a gentle simmer over medium heat. Let it cook for about 10 minutes, allowing flavors to meld and the soup to thicken slightly.
Stir in the heavy cream and continue simmering for another 2–3 minutes until the soup is warm, velvety, and well-blended. Taste again and add more salt or pepper if needed.
Serve the soup hot, garnished with a swirl of cream or a sprinkle of extra smoked paprika if desired. Enjoy its cozy, smoky richness in a warm bowl.