Prep the oven and pan: Preheat your oven to 425°F (220°C). Line a rimmed baking sheet with parchment for easy cleanup.
Arrange the vegetables: Spread the halved tomatoes (cut side up), sliced onion, and garlic cloves on the sheet. Drizzle with olive oil and sprinkle with salt and pepper.
Roast until caramelized: Roast for 30–40 minutes, until the tomatoes are blistered and the onions have golden edges.
The garlic should be soft and fragrant.
Soften the acidity: If your tomatoes are very tart, sprinkle the roasted pan with 1 teaspoon sugar or maple syrup while hot to balance flavors.
Blend the cashews (if using): Drain the soaked cashews. Add them to a blender with 1 cup of vegetable broth. Blend until completely smooth and creamy.
Build the base: In a large pot over medium heat, warm 1 tablespoon olive oil.
Stir in the tomato paste and cook for 1–2 minutes to deepen its flavor.
Add roasted veggies: Tip the roasted tomatoes, onion, and garlic into the pot (along with any pan juices). Add the remaining broth, red pepper flakes if using, and bring to a gentle simmer.
Blend to desired texture: Add the creamy cashew mixture (or coconut milk). Use an immersion blender to purée until smooth, or transfer to a blender in batches.
For a chunkier soup, blend only part of it.
Finish with basil: Stir in the basil and simmer for 2–3 minutes. Don’t boil for long—just enough to soften the basil and infuse flavor.
Season and brighten: Add vinegar to taste (start with 1 teaspoon), then adjust salt and pepper. If it needs more body, add a splash more broth or coconut milk.
Serve: Ladle into bowls and drizzle with olive oil.
Top with torn basil and a crack of black pepper. Crusty bread on the side is always a good idea.