Homemade tomato soup is not something you may think of preparing outside of the two months of the year when fresh tomatoes are at their peak. In the middle of winter, should you get a craving for a hearty wintertime tomato soup, go to your pantry, instead of your garden.
Place the oven rack in the second to highest position. Preheat the oven to 450 degrees F.
Line a jelly roll pan with foil and spray the foil lightly with nonstick cooking spray.
Place the strainer over the bowl. Use your fingers to open two 28-oz. cans of tomatoes enough to remove the seeds. Reserve the juices that have accumulated in the bowl and discard the seeds.
Place the tomatoes, in a single layer, in the foil-lined pan. Sprinkle 1 1/2 tbsp. dark brown sugar and bake 30 minutes. Remove the pan from the oven and allow the tomatoes to cool enough to handle, then remove them from the pan and place them in a small bowl.
Melt 4 tbsp. butter in a large stock pot or saucepan over medium heat until it just begins to foam. Add four minced shallots, a pinch of ground cloves and 1 tbsp. tomato paste and stir for 1 minute. Turn the heat to low and cover the pot. Cook, stirring occasionally, for seven to 10 minutes.
Add 2 tbsp. flour to the pan and cook, stirring constantly, 30 seconds or until combined. Gradually add 1 3/4 cups chicken broth, while whisking constantly. Stir in the reserved tomato juices and the tomatoes.
Increase the heat to medium, cover the pot and bring to a boil. Turn the heat to low and simmer, stirring two or three times, for 10 minutes.
Place a clean strainer over a medium bowl and pour the mixture into it. While it is draining, rinse out he pan and set it back on the stove. Place the solids from the bowl into the blender with 1 cup of the strained liquid and puree until smooth.
Pour the remaining strained liquid and the puree into the saucepan and mix it together. Add 1/2 cup heavy cream and heat over low for three minutes. Remove the pan from the heat and stir in 2 tbsp. dry sherry. Season to taste with salt and pepper.