Preheat oven to 325 degrees F. Line a large roasting pan with foil.
Remove ham from packaging and blot with a paper towel to remove any moisture. Place cut side down in the pan.
Cover the top with pineapple rings and secure with toothpicks. Place a cherry in the center of the ring and secure it with a toothpick..
Place in the oven and bake for 90 minutes, or until the internal temperature of the ham is 130 degrees F.
To make glaze: place all glaze ingredients in a small saucepan. Heat, stirring occasionally, until sugar is melted. Bring to a boil and boil 5 minutes or until it’s the consistency of a thick syrup.
Brush half the glaze over the ham and bake an additional 15-20 minutes or until glaze begins to bubble and the pineapple begins to brown around the edges. Remove from oven and brush on remaining glaze.
You will need as many cherries as pineapple rings.