Grilled Cheese With Roasted Pineapple, Ham, and Swiss Recipe

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Updated March 21, 2019

A classic grilled cheese sandwich with roasted pineapple and ham.

Recipe Details

Cook 25 mins

Total 25 mins

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Ingredients

3 tablespoons butter
2 (1/2-inch thick) slices pineapple, about 2- by 4-inches each
2 slices ham
2 slices hearty white bread, such as Pepperidge Farm or Arnold, or 2 slices hearty French or Italian bread
2 slices Swiss cheese
Kosher salt

Heat 1 tablepsoon butter in a 10-inch nonstick skillet over medium heat until foaming subsides. Add pineapple slices and cook, swirling pan occasionally, until softened and lightly browned, about 5 minutes total. Remove from skillet and set aside. Add ham and cook until lightly browned, about 3 minutes. Remove from skillet and set aside. Wipe out skillet with paper towels.
Melt 2 teaspoons of butter in the skillet over medium heat until foaming subsides. Add both bread slices and cook, swirling occasionally, until pale golden brown on bottom side, about 2 minutes.
Transfer to a cutting board toasted-side-up. Place one cheese slice on top of one slice of bread. Top with pinapple, ham, and second cheese slice. Close sandwich, with both toasted sides facing inwards.
Melt 2 more teaspoons of butter in the skillet and reduce heat to medium low. Add sandwich and cook, swirling occasionally, until deep, even golden brown, about 5 minutes. Remove sandwich using a flexible metal spatula. Add the remaining 2 teaspoons butter. Return sandwich to skillet cooked-side up. Season with salt. Cook, swirling occasionally, until second side is deep, even golden brown and cheese is thoroughly melted, about 5 minutes. Serve immediately.