- 2 tablespoons olive oil
- 1 teaspoon ground cinnamon (preferably Mexican)
- 2 1/2 pounds Mexican pumpkin (calabaza), split into wedges, seeds discarded, or 1 medium (about 21/2 pounds) butternut squash, split in half lengthwise, seeds discarded
- 1 medium (about 6 ounces) white onion, diced
- 1 firm cooking apple such as Granny Smith, peeled, quartered, and cored
- 2 to 3 canned chipotle chiles en adobo, seeds discarded, roughly chopped
- 5 cups chicken broth
- About 1 tablespoon sugar, if using
- Mexican pumpkin (calabaza)
- 3 tablespoons unsalted butter, cubed
- 1/4 teaspoon chipotle chile powder
- 1/2 teaspoon ground cinnamon (preferably Mexican)
- 11/2 teaspoons sugar
- 1/4 teaspoon salt
- 3 cups (about 5 ounces) cubed firm-textured, day-old, crust-free bread (1/2-inch cubes)
For the soup: In a large bowl, stir together the olive oil, 1/2 teaspoon of the cinnamon, and a scant 1/2 teaspoon salt. Brush part of the mixture over the cut edges of the pumpkin (or squash). Place the pumpkin (or squash) cut side down on a prepared baking sheet. Scoop the onion and apple into the bowl and toss to coat with the remaining olive oil mixture. Spread onto a separate prepared baking sheet. Slide both baking sheets into the oven and roast until the pumpkin (or squash) is soft and the onion-apple mixture is golden brown, about 1 hour for the Mexican pumpkin (or 40 to 50 minutes for the squash) and 40 to 50 minutes for the onion-apple mixture. Halfway through the cooking time, stir the onion-apple mixture. Remove both baking sheets from the oven and reduce the oven temperature to 350-degreesF.
Scoop the onion mixture into a large (4-quart) soup pot. Using a large spoon, scrape the pumpkin (or squash) flesh from its skin into the pot, then add the chipotle chiles, 1/2 teaspoon salt, and the remaining 1/2 teaspoon cinnamon.
Stir in the broth, bring to a simmer over medium heat, and simmer for 30 minutes.
For the croutons: While the soup is simmering, in a large, microwave-safe bowl, combine the butter, chipotle chile powder, cinnamon, sugar, and salt. Microwave on full power for 1 minute until the butter melts, then stir. Scoop the cubed bread into the butter mixture and toss to coat. Spread the coated bread cubes on the third prepared baking sheet and bake until the croutons are golden brown and crisp, 10 to 12 minutes.
To serve: Working in batches if necessary, transfer the soup to a blender and process to a smooth puree. Return the soup to the pot and bring back to a simmer. Taste and season with salt, usually 1/2 teaspoon. If using Mexican pumpkin, you'll also need to add about 1 tablespoon sugar. Ladle into warmed soup bowls and sprinkle the seasoned croutons on top