How to Make It
Soak bread in milk until very soft, about 5 to 10 minutes.
Meanwhile, heat 2 tablespoons of the oil in a Dutch oven over medium. Add onion, garlic, and oregano; cook, stirring occasionally, until softened, about 8 to 10 minutes. Add tomatoes and cook, stirring to crush tomatoes, until slightly thickened, about 15 minutes.
Transfer tomato mixture to a blender; add bread mixture, salt, pepper, and remaining ¼ cup oil. Process until creamy and smooth, about 1 minute. Pour back into Dutch oven; stir in vinegar. Serve hot, garnished with more oregano.