Steps:
- 1. Adjust oven rack to middle position and heat oven to 375 degrees. Line rimmed baking sheet with aluminum foil and lightly spray with vegetable oil spray. 2. Cut 1 pound tomatoes in half horizontally and arrange cut side up on prepared baking sheet. Arrange shallot and garlic cloves in single layer over 1 area of baking sheet. Roast for 15 minutes, then remove shallot and garlic cloves. Return baking sheet to oven and continue to roast tomatoes until softened but not browned, 10 to 15 minutes longer. Let cool to room temperature, about 30 minutes. 3. Peel garlic cloves and place in blender with roasted shallot and roasted tomatoes. Cut remaining 1 pound tomatoes into eighths and add to blender along with tomato paste; paprika, if using; cayenne; and 1/2 teaspoon salt. Puree until smooth, about 30 seconds. With motor running, drizzle in olive oil in slow, steady stream; puree will turn orange in color. 4. Pour puree through fine-mesh strainer into nonreactive bowl, pressing on solids in strainer to extract as much liquid as possible. Discard solids. Stir in vinegar. Cover and refrigerate until well chilled and flavors have blended, at least 2 hours or up to 24 hours. 5. To serve, stir soup to recombine (liquid separates on standing). Taste and adjust seasoning with salt and vinegar, as needed. Ladle soup into chilled bowls, drizzle sparingly with extra oil, and grind pepper over each, if using. Serve immediately.
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