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Heat olive oil in a large pot over medium heat. Add onion and cook until softened, about 5 minutes.

Add garlic, cumin, and cinnamon. Cook for 1 minute until fragrant.

Add cubed butternut squash and vegetable broth. Bring to a boil, then reduce heat and simmer until squash is very tender, about 20-25 minutes.

Add minced chipotle peppers and 1 tablespoon of adobo sauce. Stir to combine.

Using an immersion blender, puree the soup until completely smooth. Alternatively, carefully transfer to a blender in batches.

Stir in heavy cream and season with salt and pepper to taste. Simmer for 5 more minutes.

Serve hot, garnished with a drizzle of cream, toasted pepitas, and fresh cilantro if desired.