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Preheat oven to 400°F. On a rimmed baking sheet, toss the tomatoes, onions, and carrots with olive oil, salt and pepper. Arrange tomatoes cut side up. Use small square of foil to make a small packet for your garlic. Place the foil packet on the baking sheet with the other vegetables. Roast for about 45 minutes, turning the pan halfway through.
Add the roasted vegetables, canned tomatoes (crush them against the side of the pan with spoon), broth, oregano, smoked paprika, and red pepper flakes to a large stockpot. Remove garlic cloves from foil packet and add to soup.
Cook over medium low heat until everything is heated and the carrots are tender (if they weren't from the roasting), about 20 minutes.
Using an immersion blender, purée the soup until it is smooth. You can use a blender or a food processor too, just be careful and do it in small batches.
Taste and season with salt and pepper if needed. Serve with desired garnishes.