1 small loaf day-old French bread or baguette, cut into 1-inch cubes
4 tablespoons unsalted butter, melted
Kosher salt and cracked black pepper
1⁄4 pound cheddar cheese, shredded (1 1/2 cups)
For the soup, in a large saucepan or Dutch oven set over medium-high heat, heat 2 tablespoons of the olive oil.
Add the onion and garlic. Cook, stirring frequently until translucent and fragrant, about 3 minutes. Add the tomatoes and their juice, chicken broth, pesto, and sugar. Using a potato masher, crush the tomatoes. Bring the soup to a simmer and cook for 5 minutes.
Using an immersion blender, blend the soup until smooth. (Alternatively, puree the soup in batches in a standard blender.) Stir in the cream and bring the soup just to a simmer and cook for 10 more minutes. Season to taste with salt and pepper.
For the croutons, preheat oven to 325o F. Line a baking sheet with aluminum foil or parchment paper.
In a medium bowl, toss the bread cubes with the melted butter. Season liberally with salt and pepper. Spread cubes in an even layer on the prepared baking sheet. Bake until they are just starting to crisp and turn golden brown, 10 minutes. Remove the pan from the oven and top with the cheese. Bake for another 5 minutes or until cheese has melted.
To serve, pour the soup into individual bowls and garnish each with the croutons. The soup will keep in an airtight container in the refrigerator for up to 3 days.
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