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Gather all ingredients.
Preheat the oven to 325 degrees F (165 degrees C). Place ham, cut-side down, into a roasting pan.
Trim the pineapple by cutting off the skin with a sharp knife; remove any remaining brown eyes. Slice the pineapple into ½-inch-thick rings and cut out the cores with a round cutter. Attach pineapple rings to the ham with toothpicks.
Bake ham in the preheated oven for 30 minutes.
While ham bakes, whisk pineapple juice and brown sugar together in a microwave-safe bowl or small saucepan. Heat in the microwave or over medium heat until boiling and slightly thickened, about 5 minutes. Use caution because the glaze will be sticky and hot.
Pour ½ of the glaze evenly over ham and pineapple rings. Bake ham for 30 minutes more, then pour remaining glaze over ham.
Continue baking ham until a meat thermometer inserted into the thickest part of ham reads 140 degrees F (60 degrees C), 30 to 60 minutes more.
Rest the ham before slicing. Serve with the caramelized pineapple rings. Enjoy!