01 - Heat olive oil in a large pot over medium heat. Add onion, garlic, carrot, and celery. Sauté for 5-7 minutes until softened and fragrant.
02 - Add the canned tomatoes with juice, vegetable broth, sugar, salt, pepper, and oregano. Stir to combine thoroughly.
03 - Bring to a boil, then reduce heat and simmer uncovered for 20 minutes, stirring occasionally to develop flavors.
04 - Preheat oven to 375°F. Toss bread cubes with olive oil, garlic powder, and salt. Spread on a baking sheet and bake for 10-12 minutes until golden and crisp, turning halfway through.
05 - Remove soup from heat. Use an immersion blender or carefully transfer to a blender in batches to puree until completely smooth.
06 - Stir in heavy cream and chopped basil. Return to low heat and warm through for 2 minutes. Taste and adjust seasoning as needed.
07 - Ladle hot soup into bowls and top generously with crispy croutons and additional fresh basil leaves.