Confit Tomato, Aged Cheddar, Arugula Recipe

Prep Tomatoes

Preheat oven to 275°F (135°C). Halve the Roma tomatoes lengthwise and gently scoop out excess seeds if very watery. Arrange cut side up in a single layer in a small baking dish (enough to fit them snugly).

Season & Add Aromatics

Scatter the sliced garlic and thyme sprigs among the tomato halves. Sprinkle the sugar, kosher salt, and black pepper evenly over the tomatoes. Drizzle the 3 tablespoons of extra-virgin olive oil over the tomatoes so each piece gets some oil; reserve about 1 teaspoon of oil after cooking for assembly (set aside separately).

Slow-Roast

Cover the dish tightly with foil and place in the preheated oven. Roast gently for 45 minutes to 1 hour, or until tomatoes are very soft and slightly collapsed but not completely dried — they should be tender and glossy in oil. Remove foil for the last 10 minutes if you want slightly more caramelization.

Cool & Reserve

Remove from oven and let cool to room temperature. Remove thyme sprigs and discard. Using a spoon, transfer the tomatoes and their flavored oil into a small bowl or jar; reserve about 1 teaspoon of the oil for dressing the arugula and spreading on bread as noted. If the confit is very oily, you can spoon off the excess and keep it for other uses.

Prepare Arugula

In a small bowl toss the arugula with the reserved 1 teaspoon of confit oil and 1 teaspoon lemon juice (if using). Season lightly with a pinch of salt and a grind of black pepper. This brightens the greens and ties flavors to the confit.

Assemble Sandwiches

Spread mayonnaise (if using) thinly on the interior of each bread slice. On two slices, layer half of the aged cheddar evenly. Divide the confit tomatoes among the two sandwiches, placing tomato halves (or torn pieces) on top of the cheese, spooning some of the flavored oil and juices over them. Top tomatoes with the dressed arugula, then finish with the remaining cheddar if you like an extra cheesy melt. Close sandwiches with the remaining bread slices.

Grill

Butter the outsides of both sandwiches evenly with the softened butter. Heat a skillet or griddle over medium-low to medium heat. Place sandwiches butter-side down and cook gently 3–5 minutes per side, pressing lightly with a spatula or a heavy pan, until bread is golden brown and cheese is melted. Reduce heat if bread browns too quickly; you want cheese softened and tomatoes warmed, not burnt.

Rest & Serve

Transfer sandwiches to a cutting board and let rest 1 minute. Cut in half on the diagonal and serve immediately. Offer any remaining confit oil or extra tomatoes on the side for drizzling.