Preheat oven to 375 degrees. Toss bread with 1 tablespoon olive oil, 1/4 teaspoon salt, garlic powder and italian seasoning. Spread on a baking sheet and bake until toasted, but not brown, about 8 minutes. Set aside when done.
Heat a large soup pot to a medium heat. Add remaining olive oil. Add onion, carrot and 1/2 teaspoon salt. Sweat the veggies until slightly softened, about 3-4 minutes. Add garlic, cook another minute until garlic is soft and fragrant.
Add tomatoes, chicken stock, remaining 1/2 teaspoon salt, sugar and parmesan cheese rind. Bring to a boil and reduce to a simmer. Use kitchen shears to bread the tomatoes up. Simmer for 12-15 minutes until veggies are softened, but still slightly crisp and parmesan cheese rind is starting to melt into the soup. Season again with salt and pepper.
When ready to serve, add the croutons to the soup, stir for a minute or two until croutons start to soften. Serve with chopped parsley and parmesan cheese if desired.