Preheat your oven to 425°F (220°C). Line a baking sheet with parchment paper or lightly oil it.

Halve the tomatoes and place them cut-side up on the sheet. Add the quartered onion and whole garlic cloves. Drizzle with 2 tablespoons olive oil and sprinkle with a generous pinch of salt and black pepper.

Toss gently so everything is coated, then spread in a single layer so nothing steams.

Pro tip: Give the tomatoes room — overcrowding causes steaming instead of roasting. You want browned edges and a little caramelization for that deep flavor.

Roast for 25–35 minutes, or until the tomatoes are soft, the edges are caramelized, and the garlic is tender and lightly browned. If you like a bit of smokiness, slide them under the broiler for 1–2 minutes—watch closely.

Remove the pan and let the vegetables cool for 5–10 minutes so they’re safe to handle.

While the roasted veggies cool, heat your large pot or Dutch oven over medium heat. If you want extra depth, add a tablespoon of olive oil and sauté a small diced carrot or another shallot for 3–4 minutes until softened. This step is optional — the roasted onion already contributes plenty of flavor.

Add the tomato paste and stir for 30–60 seconds to cook out the tinny taste and deepen the tomato notes.

Squeeze the roasted garlic from its skins into the pot, then add the roasted tomatoes and onions. Pour in 2 cups of vegetable or chicken broth. Stir to combine.

Bring the mixture to a gentle simmer over medium-low heat. Let it simmer, uncovered, for 10–15 minutes so the flavors marry and any extra liquid reduces slightly.

Remove the pot from the heat. Use an immersion blender directly in the pot and puree until smooth and velvety. OR transfer the soup in batches to a standing blender — fill only halfway and vent the lid (hold with a kitchen towel) so steam can escape. Blend until completely smooth.

Return the blended soup to the pot if you used a standing blender.

Pro tip: When using a standing blender, vent the lid slightly and start on low speed. Hot liquids expand and can push through the lid—safety first.

Set the pot over low heat. Stir in 1/2 cup heavy cream (or half-and-half) and the fresh basil leaves. Heat gently — do not boil — for 3–5 minutes until warmed through and slightly thickened.

Taste and adjust: add salt, black pepper, and up to 1 teaspoon sugar if the tomatoes taste too acidic. If it’s too thick, stir in a splash more broth.

Pro tip: Add the cream off high heat and warm it gently — boiling will change the texture and can make it separate.

Ladle the soup into bowls. Tear a few extra basil leaves over the top and finish with a drizzle of olive oil or a small swirl of cream if you like. Serve with crusty bread or a melty grilled cheese for dunking.

This homemade creamy tomato soup keeps well in the fridge for 3–4 days in an airtight container. Rewarm gently on the stove — avoid boiling. It also freezes nicely for up to 3 months; thaw in the fridge overnight and reheat slowly.