Remove the ham from the packaging and rinse. Pat dry.
Place the ham cut side down in a shallow baking pan on a rack if you have one.
Rub 1 cup of brown sugar all over the surface of the ham.
Arrange the pineapple slices over the top of the ham securing them with tooth picks. Place a cherry inside each pineapple slice, securing with a tooth pick.
In a small bowl mix 1 cup of brown sugar with ½ cup of pineapple juice.
Drizzle half the pineapple juice brown sugar mixture over the ham. Reserve the rest for basting.
Bake the ham for 15 minutes per pound.
When the ham is done allow it to rest for about 15 minutes.
Carefully place the ham on a serving platter. Remove the tooth picks from the pineapple slices and cherries and discard. Arrange the pineapple slices and cherries around the ham on the platter.