This is one of the most delicious and simple soups to make. Serve it with a homemade grilled cheese sandwich or a fresh roll with butter.
Preheat the oven to 375 degrees F. In a roasting pan or other baking dish, arrange the tomato chunks, onion pieces, and garlic cloves cut side up. Drizzle with olive oil, season with salt and pepper, and bake 45 minutes to 1 hour or until the tips of the tomatoes and onions just begin to brown/blacken. This step can be done a day ahead if you like.
In a large pot, combine the roasted tomato mixture with the broth and tomato paste. Bring to a boil, and add 1 tsp. salt, a dash of pepper, the herbs, and the sugar and chilli flakes (if desired). Reduce heat to a simmer.
Meanwhile, in a small saucepan, gently heat* the evaporated milk or cream until very hot, stirring frequently to prevent it burning. Add this to the tomato/broth/herb mixture in the larger pot.
Using an immersion blender, purée the soup until smooth and creamy. Add the bay leaves, season to taste with salt and pepper, and allow the soup to simmer for about 20 minutes.
Discard the bay leaves and serve hot.