Grilled Pimiento Cheese Sandwiches with Apple–Cherry Chutney

Heat 2 Tbsp. oil in a medium skillet over medium-high. Cook apple (which lends sweet and sour flavors to the chutney) and onion, stirring occasionally, until soft and lightly browned, 6–8 minutes; season with salt and pepper. Stir in sambal oelek and chili powder and cook until fragrant, about 1 minute. Add tomatoes and cook, breaking up with a spoon, until beginning to darken and juices have evaporated, about 4 minutes. Add cherries and ½ cup water, season with salt and pepper, and cook, stirring, until thick and jammy, 5–7 minutes. Transfer to a serving bowl; set aside.

Meanwhile, spread mayonnaise on 1 side of each slice of bread. Turn 4 slices mayonnaise side down, then evenly spread about ⅓ cup pimiento cheese on plain side. Top with 4 remaining bread slices, mayonnaise side up.

Brush a medium skillet with oil and heat over medium. Cook 2 sandwiches until golden brown on both sides, about 3 minutes per side. Brush skillet with oil and repeat with remaining sandwiches.

Cut sandwiches in half and serve with chutney alongside for dippage purposes. Do Ahead: Chutney can be made 1 week ahead; cover and chill, or freeze 1 month.