Make sure to use canned whole tomatoes packed in juice. Use the packing juice as well as the liquid that falls from the tomatoes when they are seeded to obtain 3 cups of juice.
2 (28-ounce) cans whole tomatoes packed in juice, drained, 3 cups juice reserved
1 1/2 tablespoons dark brown sugar
4 tablespoons unsalted butter
4 large shallots, minced (about 1/2 cup)
1 tablespoon tomato paste
Pinch ground allspice
2 tablespoons all-purpose flour
1 3/4 cups homemade chicken stock or canned, low-sodium chicken broth
1/2 cup heavy cream
2 tablespoons brandy or dry sherry
Salt and cayenne pepper
1. Adjust oven rack to upper-middle position and heat oven to 450 degrees. Line rimmed baking sheet with foil. With fingers, carefully open whole tomatoes over strainer set in bowl and push out seeds, allowing juices to fall through strainer into bowl. Spread seeded tomatoes in single layer on foil. Sprinkle evenly with brown sugar. Bake until all liquid has evaporated and tomatoes begin to color, about 30 minutes. Let tomatoes cool slightly, then peel them off foil; transfer to small bowl and set aside.
2. Heat butter over medium heat in large saucepan until foaming. Add shallots, tomato paste, and allspice. Reduce heat to low, cover, and cook, stirring occasionally, until shallots are softened, 7 to 10 minutes. Add flour and cook, stirring constantly, until thoroughly combined, about 30 seconds. Gradually add chicken stock, whisking constantly to combine; stir in reserved tomato juice and roasted tomatoes. Cover, increase heat to medium, and bring to boil. Reduce heat to low and simmer, stirring occasionally, to blend flavors, about 10 minutes.
3. Pour mixture through strainer and into medium bowl; rinse out saucepan. Transfer tomatoes and solids in strainer to blender; add 1 cup strained liquid and puree until smooth. Place pureed mixture and remaining strained liquid in saucepan. Add cream and warm over low heat until hot, about 3 minutes. Off heat, stir in brandy and season with salt and cayenne. Serve immediately. (Soup can be refrigerated in an airtight container for up to 2 days. Warm over low heat until hot; do not boil.)