Grilled Cheese Tomato Soup Recipe

Prep vegetables

Core and roughly chop the tomatoes if using fresh. Peel and halve the onion. Peel and roughly chop the carrot. Smash the garlic cloves with the side of a knife.

Sauté aromatics

Heat 2 tbs olive oil in a medium pot over medium heat. Add the chopped onion and carrot and cook, stirring occasionally, until softened and beginning to brown, about 6–8 minutes. Add the smashed garlic and cook 30–60 seconds until fragrant.

Add tomatoes and seasonings

Stir in 1 tbs tomato paste and cook 1 minute. Add the chopped or canned tomatoes (include juices if using canned), 2 cups stock, 1 tsp dried basil, 1 tsp sugar, 1 tsp salt, and 1 tsp pepper. Bring to a simmer.

Simmer

Reduce heat to medium-low and simmer, uncovered, 15–20 minutes to let flavors meld and the carrots soften completely.

Blend until smooth

Remove from heat. Use an immersion blender to puree the soup until smooth; alternatively, carefully transfer batches to a blender and puree, then return to the pot.

Finish and adjust

Stir in 1 tbs heavy cream if using, and taste. Adjust salt, pepper, or sugar as needed. Keep warm on low while you make the grilled cheeses. Garnish with torn basil leaves when serving.

Assemble sandwiches

Spread softened butter evenly on one side of each slice of bread (butter side will be the outside). If using, spread ~1/2 tsp Dijon mustard on the unbuttered side of 4 slices. Divide shredded cheddar and optional gruyère between 4 slices (about 3/4 cup per sandwich), then top with remaining bread, buttered side out. Season cheese lightly with black pepper if desired.

Cook sandwiches

Heat a large skillet or griddle over medium-low to medium heat. Place sandwiches in the skillet and cook gently 3–4 minutes per side, pressing lightly with a spatula, until bread is golden brown and cheese is melted. If bread is browning too quickly before cheese melts, lower heat and cover the pan for 1–2 minutes to trap heat and help melting.

Rest and slice

Transfer sandwiches to a cutting board and let rest 1 minute. Slice each sandwich in half or into desired shapes for serving with soup.