Preheat oven to 425°F. Line a large baking tray with parchment paper.
Prep & roast vegetables: Arrange ripe roma tomatoes, halved cut-side up on the tray along with 1 medium yellow onion, quartered and 6 large garlic cloves. Drizzle with 4 tablespoons olive oil and sprinkle with 1 teaspoon dried oregano, 1 teaspoon sea salt, and 0.5 teaspoons black pepper. Roast until tomatoes are caramelised and slightly charred at the edges.
Remove the tray from the oven and allow to cool for 5–10 minutes.
Transfer all roasted vegetables (including any tray juices) into a blender or large pot if using a stick blender. Add fresh basil leaves, packed (reserve a few leaves for garnish), 1 tablespoon balsamic vinegar, and half of the chicken or vegetable broth. Blend until very smooth.
Pour the blended soup into a large saucepan over medium heat. Stir in the remaining chicken or vegetable broth and full-fat coconut milk. Add chilli flakes (optional) if using. Simmer gently, stirring occasionally, until heated through and flavours meld.
Taste and adjust seasoning with extra salt, pepper, or a splash more balsamic. Ladle into bowls and garnish with fresh basil leaves, a drizzle of olive oil, and cracked black pepper.
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