Step 1

Preheat oven to 325 degrees F (165 degrees C). Place the ham, cut side down, into a roasting pan.

Step 2

Cut the skin off the pineapple with a sharp knife and cut out any brown spots of skin left behind. Slice the pineapple into 1/2-inch slices and cut the cores out of the slices. Pin the slices onto the ham with toothpicks.

Step 3

Bake ham in the preheated oven until a meat thermometer inserted into the thickest part of the ham reads 140 degrees F (60 degrees C), 1 1/2 to 2 hours.

Step 4

While the ham is baking, mix the pineapple juice and brown sugar in a microwave-safe ceramic or glass bowl and microwave on medium power until the glaze is boiling and slightly thickened. Work carefully because the glaze will be sticky and very hot.

Step 5

Pour about half the glaze evenly over the ham and pineapple about 1 hour before the end of baking; pour the rest over the ham about 30 minutes before the end of baking.