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Preheat your oven to 400°F. Line a large baking sheet with parchment paper for easy cleanup.

On the prepared baking sheet, arrange the halved large tomatoes, cherry tomatoes, quartered bell pepper, chopped carrot, quartered onion, and the head of garlic (cut-side up). Drizzle generously with 2 tablespoons of olive oil, then season with 1/2 teaspoon salt and 1/4 teaspoon black pepper.

Roast the vegetables for 30-35 minutes, or until they are very tender, slightly caramelized, and the garlic is soft. The cherry tomatoes should be bursting.

While the vegetables are roasting, prepare the garlic herb butter for the grilled cheese. In a small bowl, combine the softened salted butter, finely grated garlic clove, finely chopped parsley, and 1/8 teaspoon salt. Mix thoroughly until well combined.

Once the roasted vegetables are done, carefully transfer them to a blender. Squeeze the softened garlic cloves from the roasted head into the blender. Add the tomato paste and chicken stock.

Blend the mixture until completely smooth. If the soup is too thick, add a little more chicken stock or water until it reaches your desired consistency.

Pour the blended soup into a saucepan. Stir in the heavy cream and fresh basil. Heat gently over medium-low heat until warmed through, about 5-7 minutes. Taste and adjust seasoning with additional salt and pepper as needed.

To assemble the grilled cheese, spread the prepared garlic herb butter evenly on one side of each sourdough slice. On the non-buttered side of two slices, layer the shredded mozzarella, Monterey Jack, and sharp cheddar. Top with the remaining two sourdough slices, buttered-side up.

Heat a large skillet or griddle over medium heat. Place the sandwiches, buttered-side down, onto the hot skillet. Cook for 3-5 minutes per side, or until golden brown, crispy, and the cheese is fully melted and gooey. You may need to cook them in batches.

Remove the grilled cheese from the skillet, slice diagonally, and serve immediately with the warm roasted tomato soup.


Preheat your oven to 400°F. Line a large baking sheet with parchment paper for easy cleanup.

On the prepared baking sheet, arrange the halved large tomatoes, cherry tomatoes, quartered bell pepper, chopped carrot, quartered onion, and the head of garlic (cut-side up). Drizzle generously with 2 tablespoons of olive oil, then season with 1/2 teaspoon salt and 1/4 teaspoon black pepper.

Roast the vegetables for 30-35 minutes, or until they are very tender, slightly caramelized, and the garlic is soft. The cherry tomatoes should be bursting.

While the vegetables are roasting, prepare the garlic herb butter for the grilled cheese. In a small bowl, combine the softened salted butter, finely grated garlic clove, finely chopped parsley, and 1/8 teaspoon salt. Mix thoroughly until well combined.

Once the roasted vegetables are done, carefully transfer them to a blender. Squeeze the softened garlic cloves from the roasted head into the blender. Add the tomato paste and chicken stock.

Blend the mixture until completely smooth. If the soup is too thick, add a little more chicken stock or water until it reaches your desired consistency.

Pour the blended soup into a saucepan. Stir in the heavy cream and fresh basil. Heat gently over medium-low heat until warmed through, about 5-7 minutes. Taste and adjust seasoning with additional salt and pepper as needed.

To assemble the grilled cheese, spread the prepared garlic herb butter evenly on one side of each sourdough slice. On the non-buttered side of two slices, layer the shredded mozzarella, Monterey Jack, and sharp cheddar. Top with the remaining two sourdough slices, buttered-side up.

Heat a large skillet or griddle over medium heat. Place the sandwiches, buttered-side down, onto the hot skillet. Cook for 3-5 minutes per side, or until golden brown, crispy, and the cheese is fully melted and gooey. You may need to cook them in batches.

Remove the grilled cheese from the skillet, slice diagonally, and serve immediately with the warm roasted tomato soup.
