Roasted Tomato Pesto Grilled Cheese (Printable)

Slow-roasted tomatoes and basil pesto elevate classic grilled cheese with melted mozzarella and cheddar on rustic bread.

# What You'll Need:

→ Roasted Tomatoes

01 - 2 large ripe tomatoes, sliced 1/4 inch thick
02 - 1 tablespoon olive oil
03 - 1/4 teaspoon sea salt
04 - 1/4 teaspoon freshly ground black pepper
05 - 1/4 teaspoon dried oregano

→ Sandwich

06 - 4 slices rustic sourdough or country bread
07 - 2 tablespoons unsalted butter, softened
08 - 2 tablespoons basil pesto
09 - 4 slices mozzarella cheese
10 - 4 slices sharp cheddar cheese
11 - Roasted tomatoes from preparation
12 - Handful of baby spinach or arugula leaves, optional

# Directions:

01 - Preheat oven to 300°F. Line a baking sheet with parchment paper.
02 - Arrange tomato slices on prepared baking sheet. Drizzle with olive oil and sprinkle with salt, pepper, and oregano. Roast for 50 to 60 minutes, flipping halfway through, until tomatoes are deeply caramelized but still hold their shape. Allow to cool slightly.
03 - Spread softened butter on one side of each bread slice. Place 2 slices buttered side down on a clean work surface.
04 - Spread 1 tablespoon pesto on the unbuttered side of each slice. Layer 2 slices mozzarella, a portion of roasted tomatoes, 2 slices cheddar, and spinach or arugula if desired. Top with remaining bread slices, buttered side up.
05 - Heat a large skillet or griddle over medium-low heat. Place sandwiches on the heated surface and cook 4 to 5 minutes per side, pressing gently, until golden brown and cheese is fully melted.
06 - Slice sandwiches in half and serve immediately.

# Expert Tips:

01 -
  • The roasted tomatoes become candy sweet and savory simultaneously
  • That pesto cuts through rich cheese with bright herbal notes
02 -
  • Low and slow roasting is what transforms ordinary tomatoes into something extraordinary
  • Medium low heat prevents burning the bread before cheese has time to melt
03 -
  • Dont rush the roasted tomatoes theyre the secret ingredient here
  • A cast iron skillet creates the most even golden crust
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