Preheat oven to 375°F. Line a rimmed baking sheet with parchment paper.
Add the tomatoes, pepper, onion, carrot, celery, and garlic to the baking sheet. Drizzle with the oil.
Combine the salt, pepper, sugar, and italian seasoning and season the ingredients.
Roast for 30 minutes, add to a blender, and blend until smooth and pureed.
Add the pureed tomato mixture, broth, and heavy cream to a Dutch oven.
Cook over medium/low heat until the soup comes to a soft boil.
Serve and enjoy, friends.