Yield: approximately 8 servings

¼ cup butter
½ cup sugar
2 tablespoons water
1 pineapple, peeled and cored

2 cups cake flour, such as Swans Down
1 teaspoon baking powder
1 teaspoon salt
¾ cup whole milk
2 teaspoons vanilla extract
2 tablespoons spiced rum
6 tablespoons butter, softened
1½ cups firmly packed light brown sugar
2 large eggs


1. In a 10-inch cast-iron skillet, melt butter for glaze over medium-low heat. Add sugar and 2 tablespoons water. Continue to cook for 30 minutes. Remove from heat, and let cool for 10 minutes.

2. Cut pineapple into ¼-inch-thick slices, then cut each slice into quarters. Arrange pineapple pieces in concentric circles on top of glaze in skillet. Set aside.

3. In a medium bowl, whisk together flour, baking powder, and salt for cake. Set aside. In another bowl, combine milk, vanilla, and rum. Set aside.

4. In a large bowl, beat butter and brown sugar at medium speed with at electric mixer until fluffy. Add eggs, mixing to combine. Add flour mixture to butter mixture in thirds, alternately with milk mixture. Pour batter over pineapple in pan.

5. Bake until a wooden pick inserted in the center of cake comes out clean, approximately 1 hour. Let cake cool for 20 minutes before inverting onto a cake plate. Let cool before serving.