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A pot of roasted red pepper tomato soup. Two bowls of soup served with three inside-out grilled cheese dumplings and fresh basil.

Inside-Out Grilled Cheese Dumplings with Tomato Soup

A playful twist on the ultimate comfort combo: grilled cheese sandwich and tomato soup. The soup is blended with roasted peppers and basil, while the cheesy bread dumplings are pan-fried until golden and crisp. Think of it as a cozy upgrade to the nostalgic childhood favourite, with a little extra crunch in every spoonful.
Prep Time 20 minutes
Cook Time 20 minutes
Total Time 40 minutes
Course Lunch, Soup
Cuisine American, North American
Servings 4 -6

Ingredients
  

For the Roasted Red Pepper & Tomato Soup

  • 4 tablespoons olive oil
  • 2 medium onions diced
  • 6 garlic cloves minsed
  • 2 cans 796 ml crushed tomatoes 1 fire roasted, 1 low sodium
  • 2 roasted red peppers peeled, seeded, and diced (jarred or freshly roasted)
  • 1 cup water
  • 1 teaspoon smoked paprika
  • ½ cup fresh basil leaves packed. Plus, extra for garnish.
  • Salt and freshly cracked black pepper to taste
  • Optional garnish: crushed chili peppers, sour cream and olive oil

For the Inside-Out Grilled Cheese Dumplings

  • 8 slices soft sandwich bread
  • 2 cups grated cheddar or cheddar blend, divided
  • 2 tablespoons milk for sealing
  • ½ cup Parmesan, grated for coating
  • 2 tablespoons butter for frying

Instructions
 

Make the Roasted Red Pepper & Tomato Soup

  • Heat olive oil in a 3 or 4-quart soup pot over medium heat. Add onions and garlic, cooking until softened and fragrant, 5-6 minutes.
  • Stir in crushed tomatoes, roasted peppers, water, smoked paprika, salt, and pepper. Simmer for 10 minutes.
  • Add basil, then blend with an immersion blender until smooth. Taste and adjust seasoning. Keep warm.

Make the Inside-Out Grilled Cheese Dumplings

  • Cut the crusts off the bread. Roll each slice of bread thin with a rolling pin. Cut each slice in half diagonally to create 16 triangles.
  • Brush the tops lightly with milk, then press both sides with Parmesan & cheddar to coat. (Note: You can also sprinkle the cheese directly into the skillet, then place the sealed dumpling on top.)
  • Heat butter in a large nonstick skillet over medium. Fry the grilled cheese dumplings 1-2 minutes per side until golden and crisp. Transfer to a paper towel briefly to drain, if required.

Serve

  • Ladle hot soup into bowls (about 12-16 oz each). Float 3-4 grilled cheese dumplings on top.
  • Garnish with basil and chili flakes. Optional: add a drizzle of olive oil or a sour cream swirl.
  • Serve immediately while the dumplings are crisp and cheesy inside.

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Video

Notes

Tips & Substitutions
  • Cheese Options: Try mozzarella, Monterey Jack, or Gruyère for different flavours.
  • Gluten-Free: Use gluten-free sandwich bread.
  • Make Ahead: Soup can be made up to 3 days ahead and reheated. Fry the cheese dumplings just before serving to keep them crisp.
  • Serving Suggestion: Pair with a light green salad for a complete meal, or serve the soup in mugs with the dumplings on skewers for an appetizer.
For Storage
  • Refrigerator: The soup will keep in a glass jar or an airtight container for up to 4 days. Reheat gently on the stove, stirring often.
  • Freezer: Cool completely, then store in freezer-safe containers for up to 3 months. Thaw overnight in the fridge before reheating.
  • Grilled Cheese dumplings: Best enjoyed fresh, but if you want to prep ahead, you can roll, fill, and seal them in advance. Fry just before serving so they stay crisp.
Keyword easy tomato and red pepper soup, roasted red pepper tomato soup, roasted tomato and basil soup, roasted tomato and red pepper soup
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