Tomato Grilled Cheese Soup (v) Recipe

Prepare vegetables

Heat a large heavy-bottomed pot over medium heat. Add 1 tablespoon of butter (from the Creaminess section) or 1 tablespoon olive oil if preferred. Add the chopped onion, carrot, and celery. Cook, stirring occasionally, until vegetables are softened and the onion is translucent, about 6–8 minutes.

Add the minced garlic and cook until fragrant, about 30–45 seconds, taking care not to brown it.

Add the chopped fresh tomatoes (or canned whole tomatoes), crushed tomatoes/passata, dried oregano, dried basil, bay leaf, sugar (if using), salt, and black pepper. Stir to combine.

Pour in the vegetable broth, increase heat to bring the mixture to a gentle boil, then reduce heat to low and simmer, uncovered, for 20–25 minutes to concentrate flavors and fully soften the tomatoes and vegetables.

Remove the bay leaf. Using an immersion blender, puree the soup until smooth. Alternatively, cool slightly and carefully transfer in batches to a blender and puree until smooth, then return to the pot.

While the soup simmers, make a roux-based cream: In a medium saucepan over medium heat, melt the remaining 1 tablespoon butter. Add the 3 tablespoons flour and whisk continuously for 1–2 minutes until the raw flour smell is gone and the mixture is pale and foamy (do not brown).

Gradually whisk in the whole milk until the mixture is lump-free. Continue whisking and cook until the mixture thickens slightly, about 3–4 minutes. Remove from heat and stir in the heavy cream.

Temper a small ladle of the hot pureed tomato soup into the milk-roux mixture (to gently raise its temperature), whisking constantly to combine. Then pour the milk-roux mixture into the main soup pot and stir until fully incorporated. Keep the pot over low heat — do not boil once dairy has been added.

Gradually stir in the shredded sharp cheddar and optional grated Parmesan, a handful at a time, stirring until completely melted and smooth. Taste and adjust seasoning with additional salt, pepper, or a pinch more sugar if the soup tastes too acidic. Keep the soup on the lowest heat to keep warm while you make the grilled cheese croutons.

Assemble sandwiches: butter one side of each bread slice. Place 1 slice of cheese between two slices of bread (buttered sides out). Repeat to make 4 sandwiches (8 slices of bread total).

Heat a large skillet or griddle over medium heat and add the optional 1 teaspoon olive oil or a small pat of butter to coat. Place the sandwiches on the hot pan and cook until the bread is golden brown and cheese is melted, about 3–4 minutes per side. Press gently with a spatula for even contact. Reduce heat if bread is browning too quickly.

Transfer grilled sandwiches to a cutting board, let rest 1 minute, then cut each sandwich into bite-size crouton pieces or triangles suitable for topping the soup.

Ladle the hot tomato grilled cheese soup into warmed bowls. Top each bowl with a handful of grilled cheese croutons so they remain slightly crisp. Sprinkle extra shredded cheddar and freshly chopped basil (chiffonade) over the top and finish with freshly cracked black pepper.

Serve immediately. Leftover soup can be cooled, refrigerated up to 3 days, and gently reheated over low heat (stir frequently to prevent sticking; add a splash of milk if it has thickened).