Nestling the crushed garlic cloves inside the tomato halves during roasting melds the flavors while also protecting the garlic from burning and imparting a bitter note to the soup. Blending whole organic milk with naturally acidic ingredients, like tomatoes and peppers, after cooking keeps the soup base from curdling. —Judy Haubert
Heat oven to 450° F and line a baking sheet with parchment paper. Toss tomatoes and garlic with olive oil, smoked paprika, 1 teaspoon salt, and 1/4 teaspoon pepper. Arrange the tomato halves cut side up on the baking sheet and nestle the garlic inside the tomatoes to keep it from burning. Roast until the tomatoes are softened and shriveled, about 25 to 30 minutes.
When the tomatoes are done roasting, let cool slightly; remove and discard their skins. Place tomatoes, garlic, and their juices in a blender along with the peppers and purée until smooth. With the motor running, slowly add milk and blend until smooth. (Strain through a fine mesh sieve for an extra-smooth texture.) Season with salt and pepper to taste.
Transfer to a storage container and refrigerate until chilled, at least 4 hours or overnight. Stir well and thin with additional milk to your desired consistency, if needed. Ladle soup into individual bowls and drizzle with good-quality olive oil and a dusting of smoked paprika, if you like. This recipe will yield about 7 cups.