Waffled Tomato-Grilled Cheese

Waffling your grilled cheese is a quick alternative to standing over your stove waiting for your bread to brown. It also ensures even delicious goldenness! Each bite tastes like tomato soup and grilled cheese at the same time.
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  • Level: Easy
  • Total: 1 hr 30 min
  • Prep: 10 min
  • Cook: 1 hr 20 min
  • Yield: 4 servings
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Ingredients

4 plum tomatoes, halved lengthwise

Olive oil, for drizzling

Kosher salt

8 slices country white bread

Melted unsalted butter, for brushing

1/4 cup mayonnaise

12 slices cheese, such as Cheddar, Swiss, Muenster or a combination

Special equipment: waffle iron

Directions

  1. Preheat the oven to 300 degrees F. Arrange the tomatoes on a baking sheet cut-side down. Drizzle with olive oil and sprinkle with salt. Slow-roast until the tomatoes are soft and wrinkled, about 1 hour. Set aside to cool. (The tomatoes can be made and refrigerated up to 1 day ahead.) 
  2. Preheat a waffle iron to medium-high. Brush one side of each bread slice with melted butter. Lay the bread out on a clean work surface, dry-side up. Spread each slice of bread with some of the mayonnaise. Top 4 bread slices with 2 tomato halves, slightly smashing them into the bread. Top with 3 cheese slices each and the remaining bread slices. 
  3. Place two sandwiches at a time in the waffle iron and gently close the lid (don't press down). Cook until the cheese is melted and the sandwiches are golden-brown, 6 to 10 minutes. Repeat with the remaining sandwiches. Cut in half and serve.
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