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1
Preheat your oven to 400 F.
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2
Drain the tomatoes and reserve the liquid. Halve the tomatoes lengthwise and arrange them in an even layer in a roasting pan or on a rimmed baking sheet. Drizzle with 2 tablespoons of the olive oil and sprinkle with a little kosher salt and pepper.
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3
Wrap the garlic cloves in tinfoil. Place the foil packet of garlic on the baking sheet with the tomatoes. Put the pan into the oven and roast for 35 minutes, turning the tomatoes once halfway through the cooking time. Remove pan from oven and set aside to cool for a few minutes.
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4
When cool enough to handle, slice the tip off each clove of garlic and squeeze the roasted garlic out. (It will be an awesomely delicious paste). Briefly set aside.
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5
Heat the remaining tablespoon of olive oil in a medium Dutch oven or saucepan over medium heat. When hot, add the onions and saute for 3 minutes until translucent. Add the roasted tomatoes and any juices from the pan to the pot with the onions, and stir in the roasted garlic, the reserved tomato liquid, vegetable stock, sugar, crushed red chili flakes and basil sprigs. Bring the soup to a boil, then lower heat to a simmer and cook uncovered for 20 minutes to allow the awesome flavors to combine.
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6
Remove the whole basil sprigs from the pot and puree the soup using an immersion blender, food processor, or regular blender. (If you do this in the blender fill the container only halfway full for each batch-otherwise the steam may cause it to explode.) Return the pureed soup to the pot and stir in the chopped basil. Taste your fabulous creation and season with salt and pepper to taste. If you want a creamy soup, stir in 1/3 cup of heavy cream over low heat.
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7
Serve soup garnished with a little extra basil, a drizzle of fancy oil and a sprinkling of cheese if you're into that. Maybe get some grilled cheese sticks involved.
