Step 1

Preheat oven to 300°. Stack 2–3 sheets of foil ample enough to cover ham on a work surface and arrange pineapple and orange slices on top in a single layer. Set ham on fruit (if using a bone-in ham and it has a fat cap, score very lightly, making cuts about ¾" apart) and wrap up tightly. Transfer to a wire rack set inside a large rimmed baking sheet and bake until an instant-read thermometer inserted into the thickest part of ham registers 115°, 3–3½ hours for boneless, 3½–4 hours for bone-in.

Step 2

Meanwhile, bring pineapple juice, vinegar, brown sugar, and hot sauce to a boil in a large saucepan. Reduce heat; simmer, swirling occasionally, until thick enough to coat a spoon. Keep warm.

Step 3

Remove ham from oven and increase oven temperature to 425°. Unwrap ham, peeling back the foil so it covers the baking sheet (this will make for easy cleanup). Once oven is at 425°, baste ham with warm glaze and return to oven. Bake, brushing with more glaze every 3 minutes or so, until glaze is deeply browned and thermometer registers 125°, 12–15 minutes. Carefully transfer ham to a cutting board and let rest 30–60 minutes before slicing.

Step 4

While ham is resting, roast fruit, spooning juices over from time to time, until deeply browned, 20–25 minutes.

Step 5

Serve ham with roasted fruit and cherries alongside.