The soup: Preheat oven to 425°F Spread oil over the bottom of a shallow.
baking dish and pour in tomatoes and juices. Mix in shallots and salt and pepper and drizzle the top with olive oil.
Cook for 35 – 45 minutes or until juices have thickened and slight charring has occurred. Let cool slightly, then blend in a food processor or pass through a food mill using the finest disk. Roasting seems to soften the seeds to where they are barely noticeable, so, unless you want a very smooth texture, using the processor is certainly acceptable. Correct seasoning and, if the flavor is too sharp or acidic, whisk in additional olive oil until flavors balance.
Fresh herb oil: Place all ingredients into a blender and blend on high for 20 – 30 seconds. Use immediately or cover and refrigerate for up to 4 days (oil will separate with storage but comes together easily when whisked).
For the Croutons: Heat oil and garlic cloves over medium heat in a medium sauté pan.
When oil shimmers, add bread, tossing to coat with oil. Sprinkle on remaining ingredients and cook, tossing frequently, until golden. Discard garlic.
To Serve: Reheat soup and blend with a whisk. Drizzle with herb oil and serve with croutons on the side.