Preheat your oven to 425°F (220°C). Toss the halved tomatoes, chopped onion, and whole garlic cloves with 2 tablespoons olive oil, salt, and pepper on a rimmed baking sheet.

Spread them in one layer so everything gets a little caramelized.

Roast for 25–35 minutes, turning once halfway through, until edges are browned and the tomatoes have collapsed.

For additional char, bump the oven to broil for the last 2 minutes while watching closely.

While the tomatoes roast, heat the remaining 1 tablespoon olive oil and butter in a large pot over medium heat.

Add a teaspoon of tomato paste and cook for 1 minute to deepen flavor (this is optional).

Add the roasted onions and garlic straight from the pan.

Add the roasted tomatoes to the pot and pour in the broth.

Add oregano or thyme, bring to a gentle simmer, and let everything mingle for 10 minutes.

Use an immersion blender directly in the pot to puree until smooth.

For a super-smooth finish, transfer the soup in batches to a blender and blend until velvety.

Lower the heat and stir in the heavy cream or coconut milk. Warm gently—don’t boil—so the cream doesn’t break.

Taste and adjust salt, pepper, and a pinch of red pepper flakes if desired.

Ladle into bowls, garnish with fresh basil and croutons or a classic grilled cheese on the side.

Store leftovers in an airtight container in the fridge for up to 3 days, or freeze for up to 3 months.