Grilled Cheese & Tomato Soup Dumplings Recipe

Prepare cheese filling

In a bowl, combine the shredded sharp cheddar and shredded mozzarella. Season with 1/4 tsp kosher salt and 1/8 tsp black pepper. Mix thoroughly so the mixture is even.

Assemble wontons

Lightly dust a work surface with 1 tsp flour. Lay one wonton wrapper flat. Brush the edges with a little water (about 1/8 tsp). Place about 1 tablespoon of the cheese mixture in the center of the wrapper, leaving the edges clear. Fold the wrapper into a triangle (or bring corners together) pressing the edges firmly to seal. For a pouch: bring all four corners to the center and press to seal, using a tiny dab of water if needed. Repeat until all wrappers are filled (should make about 24 dumplings).

Pan-fry to 'grilled' finish

Heat a large nonstick skillet over medium heat. Add 1 tsp olive oil and swirl. Arrange dumplings flat in a single layer (work in batches if necessary). Brush the tops with melted butter. Cook 2–3 minutes until bottoms are golden brown and crisp. Carefully flip each dumpling, brush the now-cooked side with more butter, and cook an additional 2–3 minutes until both sides are golden and cheese is melted. Transfer to a baking sheet and keep warm in a 200°F (95°C) oven while you finish the soup.

Alternative: bake (optional)

Preheat oven to 400°F (200°C). Arrange assembled dumplings on a parchment-lined sheet, brush with melted butter, and bake 8–10 minutes, turning once, until wrappers are puffed and golden and cheese is melted.

Sweat aromatics

Heat 1 tablespoon olive oil in a medium saucepan over medium heat. Add the chopped onion and grated carrot. Cook, stirring occasionally, until softened and translucent, about 5–6 minutes. Add minced garlic and cook another 30–60 seconds until fragrant.

Build tomato base

Add the chopped or canned crushed tomatoes and 2 tablespoons tomato paste to the pan. Stir to combine and cook 2–3 minutes to reduce the raw tomato flavor.

Simmer

Pour in 2 cups vegetable broth, add 1/2 teaspoon dried oregano, 1/2 teaspoon sugar, and 1 teaspoon kosher salt. Bring to a gentle simmer and cook uncovered for 10–12 minutes to let flavors meld.

Finish and blend

Stir in half of the basil leaves (torn) and remove the pan from heat. Using an immersion blender (or transfer carefully to a blender in batches), purée the soup until smooth. Return to low heat. Stir in 1/2 cup heavy cream, adjust seasoning with additional salt and pepper to taste, and warm gently — do not boil after adding cream.

Keep warm

Maintain the soup at a low simmer while you fry or reheat the dumplings so both components are hot when served.

Ladle the hot garden tomato soup into shallow bowls. Float 3–4 warm grilled cheese dumplings in each bowl (depending on size). Scatter chiffonaded basil over the soup and dumplings, drizzle with 1 teaspoon extra-virgin olive oil, and finish with a light crack of black pepper.

Serve immediately so dumpling wrappers remain crisp on the exterior while the interior stays molten and melty. Provide extra napkins—these are cheesy and delicious.