Ingredients

• 2 pounds tomatoes, cored, quartered
• 2 garlic cloves, smashed
• 1/2 teaspoon fennel seeds
• 6 tablespoons olive oil, divided, plus more
• Kosher salt
• Freshly ground black pepper
• 4 sprigs basil
• 1/4 loaf country-style bread, crust removed, torn into 2" pieces (about 1 1/2 cups), divided

Instructions

1. Preheat oven to 450°. Toss tomatoes, garlic, fennel seeds, and 3 tablespoons oil in a large baking dish; season with salt and pepper.
2. Roast, stirring occasionally, until the tomatoes are browned and the juices thicken, 30–35 minutes.
3. Transfer tomato mixture to a large saucepan; add basil, 1 cup torn bread, and 4 cups water. Bring to a boil, reduce heat, and simmer, stirring occasionally and breaking up bread and tomatoes a little, until bread is softened and soup has thickened slightly, 8–10 minutes; season with salt and pepper.
4. Meanwhile, tear remaining 1/2 cup bread into smaller pieces; toss on a baking sheet with 3 tablespoons oil; season with salt. Toast, tossing often, until crisp, 5–8 minutes.
5. Serve soup topped with toasted bread and drizzled with more oil.