Brown Sugar-Roasted Tomato Soup with Cheddar Croutons Recipe

Adjust oven racks to middle positions and preheat oven to 375°F. Featured Video Prepare the tomatoes: spray a large rimmed sheet tray with an even coating of cooking spray. Add drained tomatoes and space evenly. Season tomatoes to taste with salt and pepper, then divide brown sugar over tops of tomatoes. Roast tomatoes in oven until sugar is browned and tomatoes have shrunken slightly, about 45 minutes. Remove tomatoes from oven. Meanwhile, prepare the croutons. In a large bowl, toss cubed bread with olive oil, salt and pepper to taste, and grated cheddar cheese. Massage bread so cheese adheres well. Turn out onto a rimmed baking sheet and bake, stirring occasionally, until well-browned and crisp, 10 to 12 minutes. Remove from oven and let cool. Prepare the soup: Heat butter in a large, heavy-bottomed Dutch oven set over medium heat. Add shallots, garlic, and thyme (if using), and season with salt and pepper. Cook, stirring occasionally, until shallots are translucent but not browned, about 6 minutes. Add tomato paste and cook, stirring, until it browns, about 2 minutes. Add roasted tomatoes, reserved tomato liquid, and enough water to cover, about 3 cups. Bring soup to a boil, reduce to a simmer and cook, stirring occasionally, until some liquid has evaporated, about 30 minutes. Let soup cool slightly, about 10 minutes. Add half and half and use a hand blender to blend soup until smooth. Alternatively, blend soup in a blender in two batches. Check soup for seasoning, adding more salt and pepper to taste. Serve in bowls, garnished with a handful of croutons.