Preheat oven to 350˚F, Wash potatoes and boil with skins on for 30 minutes or until tender all the way through. Drain and allow to cool. Peel and cut length-wise into halves.

Arrange slices of pineapple in a single layer in a greased shallow baking dish; place the potatoes cut side down on top of each pineapple slice.

In a small pan, heat butter, brown sugar and sherry together until sugar is dissolved add salt and pepper and stir; pour over potatoes and pineapple. Bake for 30 minutes, basting often with the syrup in the baking dish.

Serve hot.