Preheat your oven to 400°F (200°C) and spread the cubed pumpkin and whole garlic cloves on a baking sheet, drizzling with olive oil. Roast until the pumpkin is tender and lightly caramelized, and the garlic is soft and fragrant, about 25-30 minutes.
Once roasted, let the garlic cool slightly, then squeeze the roasted garlic out of its skins into a bowl. Set aside.
In a large pot, heat a splash of olive oil over medium heat. Add chopped onion and cook until translucent and fragrant, about 5 minutes. Stir occasionally to prevent sticking.
Add the roasted pumpkin to the pot, along with the roasted garlic. Stir to combine and let cook for a minute as the flavors meld.
Pour in the apple cider and broth, then bring the mixture to a gentle simmer. Season with salt and pepper to taste. Cover and let simmer for 10-15 minutes, allowing the flavors to deepen.
Using an immersion blender (or transferring carefully to a blender), blend the soup until perfectly smooth and velvety. Be cautious with hot liquids—blend in batches if necessary.
If desired, stir in cream or coconut milk to add richness and a subtle sheen to the soup. Adjust seasoning with more salt and pepper if needed.
Heat the blended soup gently for a minute to warm through. Serve hot, garnished with a swirl of cream or toasted seeds if you like.