Fiery Roasted Garlic Tomato Soup With Cheese Toasts

Ingredients: (serves about 6)

15 whole Roma Tomatoes
7 Tablespoons Olive Oil, divided use
1-½ tablespoon Balsamic Vinegar
3 tablespoons Brown Sugar
1 tablespoon Salt
1 teaspoon Fresh Cracked Black Pepper
1 Tablespoon Red Chili Pepper Flakes
2 teaspoons Italian Seasoning
3 whole Heads Of Garlic (peels Left On), plus 2 cloves, chopped, divided use
1 whole Onion, chopped
1 bunch Lemon Basil (or Regular Basil), stems removed and chopped
¼ cups Flat-leaf Parsley, chopped
3 ½ cups Chicken Stock
1 cup Croutons (packaged)
½ cup Grated Parmesan Cheese
1 loaf rustic-style Bread, such as Ciabatta
6 Tablespoons Gruyere Cheese, shredded


Preheat oven to 400 degrees F and line 2 baking sheets with foil.
-Cut the Roma tomatoes in half and place in a large bowl; add the 2 Tablespoons of olive oil as well as the balsamic vinegar and other ingredients down through the Italian seasoning to the tomatoes, and toss to coat; add to baking sheet to roast for 45 minutes.
-Cut the tops off of the 3 heads of garlic and add 2 Tablespoons of the olive oil; wrap the oiled heads tightly in foil, and place them next to the tomatoes to roast for 40 minutes.
-Once tomatoes and garlic are roasted, set aside to cool slightly until they can be handled; then squeeze the roasted garlic cloves out of their papers, discard papers and set aside the roasted garlic. (Keep oven set to 400 degrees, as it will be needed to make the cheese toasts later.)
-In the meantime, in a large pot over medium heat, add the remaining 2 Tablespoons of olive oil, the chopped onion and 2 fresh, chopped garlic cloves. Allow them to become aromatic and translucent. Then add the roasted tomatoes (and all of their juice from the baking sheet), and the roasted garlic; add the basil and parsley and stir to combine; add the hot chicken stock and the croutons and allow to gently simmer without lid, for about 20 minutes.
-Finally, add the grated Parmesan cheese, and using a hand immersion blender, puree the soup until smooth and all tomatoes are completely pureed (if using a blender, work in small batches to puree- be careful to not overfill the blender, as hot soup can splatter); check the salt/pepper, and adjust, if necessary; keep soup warm.
-To make the cheese toasts, cut the rustic bread into six 1/2″ slices, drizzle with 1 Tablespoon of olive oil, and place on baking sheet and into oven to toast until golden; remove bread from oven and top each with 1 Tablespoon of the Gruyere cheese and place in oven once again, just until cheese is melted; remove bread from oven and cut each slice on the bias (making 12 pieces); keep warm.
-Ladle soup into serving bowls, and garnish with 2 pieces of the Gruyere cheese toasts.