Step 1

Preheat oven to 325°F. Pierce pineapple all over with cloves. Place sugar and 1/4 teaspoon pepper in a 2-quart baking dish; roll pineapple in sugar to coat. Scatter butter in pan.

Step 2

Bake, brushing pineapple with sugar-butter mixture occasionally, until very tender, 1 to 1 1/4 hours. Transfer pineapple to a cutting board; remove cloves.

Step 3

Place sugar mixture from dish in a saucepan with cream. Simmer until thickened slightly, 6 to 8 minutes. Quarter pineapple lengthwise; serve with vanilla ice cream, pan sauce, and sprinkles of flaky salt and more pepper.