Ham dressed in pineapple rings and maraschino cherries is a holiday classic, burnished with a glossy glaze made with pineapple juice, honey and brown sugar. If you like sweet and salty, you'll love this show-stopping centerpiece!
Let the ham sit at room temperature for about 30 minutes.
Preheat the oven to 325 degrees F.
Trim off any skin from the ham. Use a sharp paring knife to score through the fat in a diagonal crosshatch pattern without cutting through to the meat. Push the cloves into the ham, if using, placing them at the intersections of the cuts. Put the ham, flat-side down, on a rack in a roasting pan.
Drain the pineapples, reserving the juice. Arrange the sliced pineapple all over the ham, securing with toothpicks. Add a maraschino cherry to the center of each pineapple slice and secure with a toothpick.
Pour 1/4 inch water in the bottom of the pan and tent the ham with foil.
Roast until an instant-read thermometer inserted in the thickest part of the ham (avoiding bone) registers 130 degrees F, about 2 hours 30 minutes (or about 15 minutes per pound).
Meanwhile, combine the honey, brown sugar and reserved pineapple juice in a large saucepan set over medium heat. Simmer, stirring occasionally, until thickened, syrupy and reduced to about 3 cups, 25 to 30 minutes. Set aside.
Increase the oven temperature to 425 degrees F.
Uncover the pan and carefully brush a third of the glaze all over the ham. If the water in the roasting pan has evaporated, add more. Bake the ham for 15 minutes more. Brush with another third of the glaze and bake for 15 minutes more. Brush the remaining glaze over the ham and cook until the glaze is shiny and the skin is dark golden brown and crispy, about 15 minutes more. Let rest for 15 minutes.
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