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Preheat the oven to 400°F (205°C) and prepare a sheet pan lined with aluminum foil.
Cut the tomatoes in half or into quarters depending on their size. Transfer the tomatoes onto the prepared sheet pan along with the onion chunks and garlic cloves. Drizzle with olive oil and bake for about 40 minutes or until the vegetables are softened and a little browned.
Once done, remove the roasted tomatoes and aromatics from the oven and transfer everything (including the juices) to a high power blender. Add the vegetables stock and basil and blend until smooth.
Transfer the blended tomato soup into a pot and season with salt and sugar. Bring the soup to a low simmer and cook for about 5 minutes with the lid cracked. Stir occasionally.If you prefer your tomato soup thinner, add more stock now. If you prefer it thicker, simmer for an additional 5 to 10 minutes, or to your desired consistency.
When the tomato soup is done simmering, transfer to serving bowls and top with a drizzle of cream and/or olive oil, basil, and some croutons. Enjoy while hot!