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Makes 15 to 20 servings, about 3 1/2 quarts

1/4 cup olive oil
3 teaspoons ground cinnamon (preferably Mexican cinnamon), divided use
1/2 teaspoon ground cumin
Salt
1 large (about 5 pounds) butternut squash, split in half lengthwise, seeds
removed and discarded
2 large carrots, diced
1 large white onion, diced
2 firm, cooking apples, like Granny Smith, peeled, cored and quartered
2 1/2 quarts chicken broth
3 to 4 canned chipotle chiles en adobo, seeds scraped out, roughly chopped
6 tablespoons unsalted butter, cubed
1/2 teaspoon chipotle powder
1 tablespoon sugar
About 10 ounces firm-textured day-old bread, crusts removed, cut into 1-inch
cubes (7 cups)

Preheat oven to 425 degrees.

In a large bowl, mix the olive oil, 1 teaspoon cinnamon, cumin, and 3/4
teaspoon salt. Brush part of the mixture over the cut edges of the squash.
Place cut side down onto a rimmed baking sheet lined with foil. Scoop the
carrots, onions and apples into the bowl and toss to coat. Spread onto a
separate foil-lined rimmed baking sheet.

Slide both sheets into the oven and roast for about 40 to 50 minutes or
until the onion mixture is golden brown and the squash is soft. Halfway
through the cooking time, stir the onion mixture. Remove from the oven and
reduce the temperature to 350 degrees.

Scoop the onion mixture into a large (6-quart) soup pot. Using a large
spoon, scrape out the squash flesh and add it to the pot along with the
chipotles, 1 teaspoon salt and 1 teaspoon cinnamon. Pour in the chicken
broth and stir to combine. Cook over medium heat for 30 minutes.

Meanwhile, in a large microwave safe bowl, add the butter, chipotle powder,
remaining 1 teaspoon cinnamon, 1/2 teaspoon salt, and the sugar. Microwave
on high for 1 minute until the butter has melted, stir. Scoop in the cubed
bread and toss to coat. Spread onto a foil-lined rimmed baking sheet and
bake for 10 to 12 minutes until the croutons are golden brown and crisp. Set
aside.

After 30 minutes, transfer the soup, in batches, into a blender and puree
until smooth. Return to the pot and bring back to a simmer. Taste and adjust
the seasoning with salt, usually 1 teaspoon. Ladle into soup bowls and
garnish with seasoned croutons.
 
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