Step 1: Sauté the Aromatics
Heat the olive oil or butter in a large, heavy-bottomed pot or Dutch oven over medium heat. Once shimmering, add the diced onion and a pinch of salt. Cook for 5-7 minutes, stirring occasionally, until the onions are soft, translucent, and just beginning to turn golden at the edges. Add the minced garlic and cook for 1 minute more, stirring constantly until fragrant. Don’t let the garlic burn or it will taste bitter.

Step 2: Cook the Tomato Paste
Add the tomato paste to the pot and stir it into the onions and garlic. Cook for 1-2 minutes, stirring frequently, until the tomato paste darkens slightly and becomes fragrant. This step cooks out the raw metallic taste and concentrates the tomato flavor.

Step 3: Add Tomatoes and Broth
Pour in the whole peeled tomatoes with their juices, crushing them by hand as you add them to the pot, or break them up with a wooden spoon. Add the crushed tomatoes, vegetable or chicken broth, sugar (start with 1 teaspoon), dried oregano, and dried basil (or fresh basil leaves). Stir everything together to combine well.

Step 4: Simmer the Soup
Bring the mixture to a boil over medium-high heat, then reduce the heat to low and let it simmer gently, uncovered, for 15-20 minutes. This allows the flavors to meld together and the tomatoes to break down further. Stir occasionally to prevent sticking.

Step 5: Blend Until Smooth
Remove the pot from the heat. Using an immersion blender, carefully blend the soup directly in the pot until completely smooth and creamy. If you don’t have an immersion blender, carefully transfer the soup in batches to a regular blender (filling it only halfway each time), and blend until smooth. Return the blended soup to the pot.

Step 6: Add Cream and Season
Place the pot back over low heat. Stir in the heavy cream or half-and-half until fully incorporated. Taste the soup and season with salt and freshly ground black pepper. If the soup tastes too acidic, add the remaining teaspoon of sugar. Let the soup warm through for 2-3 minutes, but don’t let it boil once the cream is added.

Step 7: Serve
Ladle the creamy tomato soup into bowls. Garnish with fresh basil leaves, a drizzle of cream or olive oil, and an extra crack of black pepper if desired. Serve immediately with grilled cheese sandwiches or crusty bread.