Roasted Tomato Pesto Grilled Cheese

The smell of slow-roasting tomatoes filling my apartment on a rainy Sunday afternoon changed everything I thought I knew about grilled cheese. I had been experimenting with tomato confit for a pasta dish when I realized how incredible those concentrated, sweet-tangy slices would taste pressed between bread and melting cheese. That first sandwich was absolute perfection.

My roommate walked in mid-bite that first time and immediately demanded I make her one. Now whenever one of us has had an especially long day at work, we know exactly what dinner will be. There is something about that combination of warm, crusty bread and slow-roasted tomatoes that feels like a hug.

Ingredients

• 2 large ripe tomatoes: Choose ones that give slightly when pressed because they will concentrate into something incredible during roasting
• 1 tbsp olive oil: This helps the tomatoes caramelize and develop those deep, rich flavors
• 1/4 tsp sea salt: Essential for drawing out moisture and intensifying the tomato taste
• 1/4 tsp freshly ground black pepper: Adds just enough warmth to balance the sweetness
• 1/4 tsp dried oregano: Brings an earthy note that pairs beautifully with basil pesto
• 4 slices rustic sourdough or country bread: The sturdy texture holds up to all those layers without getting soggy
• 2 tbsp unsalted butter: Spread generously on the outside for that perfect golden crunch
• 2 tbsp basil pesto: Homemade is wonderful but good store-bought works perfectly here
• 4 slices mozzarella cheese: Provides that incredible stretch factor when melted
• 4 slices sharp cheddar cheese: Adds the perfect tangy contrast to mild mozzarella
• Handful of baby spinach or arugula: Optional but adds a nice fresh bite and makes you feel slightly virtuous

Instructions

Roast the tomatoes into sweet concentrated gems:

Preheat your oven to 300°F and line a baking sheet with parchment paper. Arrange tomato slices in a single layer, drizzle with olive oil, and sprinkle with salt, pepper, and oregano. Roast for 50 to 60 minutes, flipping halfway through, until they are shriveled and deeply caramelized but still hold their shape.

Build your sandwich layers with intention:

Spread butter on one side of each bread slice. Place two slices butter-side down and spread pesto generously on the opposite side. Layer mozzarella first so it melts and binds everything together, add those precious roasted tomatoes, then sharp cheddar for flavor punch, and finish with spinach if you are using it.

Grill to golden perfection:

Heat a skillet over medium-low heat and carefully transfer your sandwiches. Cook for 4 to 5 minutes per side, pressing gently with your spatula, until the bread is deeply golden and the cheese is oozing out the sides. Resist the temptation to rush this part because slow cooking gives you that perfectly melted interior.

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This recipe has become my go-to for feeding friends who need comfort. Last month my neighbor was going through a breakup and I brought over two of these sandwiches. She said it was exactly what she needed.

Make It Your Own

I have played around with different cheeses and found that fontina adds this incredible nutty sweetness while provolone brings a smoky depth. Sometimes I add a thin layer of sun-dried tomato pesto instead of regular basil pesto for double tomato intensity.

Timing Is Everything

The roasted tomatoes can be made up to three days ahead and stored in the refrigerator. Actually I think they taste even better the next day when the flavors have had time to meld together.

Serving Suggestions

A simple green salad with vinaigrette cuts through all that rich cheese perfectly. I also love serving this alongside tomato soup for the ultimate comfort food experience.

• Let the sandwich rest for two minutes before slicing so the cheese sets slightly
• Cut on the diagonal for that classic diner look
• Serve while still hot but not mouth-burning temperature

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There is nothing quite like cutting into that first sandwich and watching the cheese stretch while steam rises into the kitchen air. Pure happiness on a plate.

Recipe Questions & Answers

→ Can I make the roasted tomatoes ahead of time?

Yes, roast tomatoes up to 3 days in advance and store in an airtight container in the refrigerator. They'll actually develop more intense flavor over time.

→ What type of cheese works best?

The combination of mozzarella for melt and cheddar for sharpness is ideal, but provolone, fontina, gruyère, or smoked gouda all work wonderfully.

→ How do I prevent the bread from burning before the cheese melts?

Cook over medium-low heat and be patient. Lower heat allows the cheese to melt completely while the bread gradually turns golden and crispy.

→ Can I use store-bought pesto?

Absolutely. Quality store-bought basil pesto works great here. Just look for one without too much oil, which could make the sandwich soggy.

→ What can I serve with this sandwich?

A crisp green salad with vinaigrette cuts through the richness, or serve with a warm cup of tomato soup for the ultimate comfort meal.

→ How do I make this gluten-free?

Simply substitute the sourdough bread with your favorite gluten-free bread. The rest of the ingredients are naturally gluten-free.