Preheat your oven to 400°F. Place tomato halves on a baking sheet. Drizzle with olive oil. Roast for about 30 minutes. The tomatoes should become soft and slightly caramelized. This step adds wonderful flavor to the soup.

Heat a little olive oil in a large soup pot. Add the diced onion. Cook for about 5 minutes. Stir often until the onion becomes soft and slightly golden. This creates a flavorful base.

Add minced garlic to the onions. Cook for about one minute. Stir constantly to prevent burning. Fresh garlic gives the soup a rich and savory taste that blends perfectly with tomatoes.

Add the roasted tomatoes to the pot. Pour in the chicken broth. Stir in tomato paste, salt, pepper, sugar, and oregano. Mix everything well so the flavors combine evenly during cooking.

Bring the mixture to a gentle boil. Reduce the heat. Let the soup simmer for about 15 minutes. This helps all the ingredients blend together and creates a deeper flavor.

Add the fresh basil leaves. Stir them into the soup. The heat will soften the basil and release its wonderful aroma. This step adds freshness and balance to the rich tomato flavor.

Use an immersion blender directly in the pot. Blend until smooth and creamy. If using a regular blender, work carefully in small batches. The soup should have a silky texture.

Pour in the heavy cream. Stir gently until fully combined. The cream makes the soup rich and smooth. Let it cook for another 2 minutes without boiling.

Taste the soup before serving. Add extra salt or pepper if needed. Every batch of tomatoes is different, so small adjustments can make a big difference.

Ladle the soup into bowls. Garnish with fresh basil. Serve warm with grilled cheese sandwiches or crusty bread. Enjoy every comforting spoonful of this homemade favorite.