Sharp Cheddar and Sourdough Grilled Cheese with Roasted Tomato Soup

Steps

Every amount is written into the step where you use it.

!Steps marked like this need your attention — stay close so nothing burns.

Roasted Tomato Soup

1. Preheat the oven to 425°F and line a large rimmed baking sheet with parchment paper. 15 min
2. Arrange the 2½ pounds of halved roma tomatoes cut-side up on the baking sheet with the quartered onion and 6 unpeeled garlic cloves, drizzle with 3 tablespoons olive oil, and season with 1 teaspoon kosher salt, ½ teaspoon black pepper, and ¼ teaspoon crushed red pepper flakes if using. 6 min
3. Roast the vegetables for 35 minutes until the tomatoes are collapsed, caramelized at the edges, and the onion is deeply golden. 35 min
4. Squeeze the roasted garlic cloves from their skins, then transfer all roasted vegetables and their juices to a blender; add 2 cups chicken broth and blend on high until very smooth, about 1 minute. 4 min
5. Pour the blended soup into a medium saucepan over medium heat, stir in ⅓ cup heavy cream, 1 tablespoon unsalted butter, and ½ teaspoon sugar if using, and simmer for 8 minutes, stirring occasionally, until slightly thickened. 8 min
6. Taste the soup and adjust seasoning with salt and pepper, then stir in ¼ cup loosely packed fresh basil leaves just before serving. 2 min

Sharp Cheddar and Sourdough Grilled Cheeseside

1. In a small bowl, stir together 4 tablespoons softened unsalted butter and 2 tablespoons mayonnaise until evenly combined, then spread the mixture in a thin, even layer on one side of each of the 8 sourdough slices. 4 min
2. If using, spread a thin layer of Dijon mustard on the unbuttered (inner) side of 4 of the bread slices, then divide the 10 ounces of freshly grated sharp cheddar evenly among those 4 slices and top each with a second slice, butter-side out. 5 min
3. Heat a large cast-iron skillet or griddle over medium-low heat for 2 minutes until evenly hot. 2 min
4. Timing-sensitive step. Place 2 sandwiches in the skillet and cook for 4–5 minutes, pressing gently with a spatula, until the bottom is deep golden brown and the cheese begins to melt. 5 min
5. Timing-sensitive step. Flip each sandwich and cook for another 3–4 minutes until the second side is evenly golden and the cheese is fully melted, then transfer to a cutting board and repeat with the remaining 2 sandwiches. 4 min
6. Sprinkle ¼ teaspoon flaky sea salt over the tops of the sandwiches, slice each diagonally, and serve immediately alongside the roasted tomato soup. 2 min