Pineapple Upside-Down Cake


Preparation info

  • Difficulty


  • Makes One 8 Inch Cake; Serves


Appears in

I grew up on this magnificent pineapple upside-down cake, and some of my fondest memories are of my mother inverting the cake, unveiling the caramelized and glistening fruit, bathed in a wash of syrup and pure buttery beauty.


  • nonstick cooking spray


  • 1 cup water
  • ¾ cup packed light brown sugar
  • ¼ cup packed dark brown sugar
  • 1 vanilla bean, split lengthwise
  • 1 ripe pineapple, peeled, cut into ten ¼-inch-thick crosswise slices, and cored
  • 1 tablespoon unsalted butter
  • 2 tablespoons coconut rum


  • 1 cup granulated sugar
  • ½ cup sorghum flour
  • ¼ cup glutinous rice flour
  • ¼ cup cornstarch flour
  • ½ cup tapioca flour
  • ½ teaspoon baking soda
  • ¾ teaspoon baking powder
  • ¼ teaspoon kosher salt
  • 7 tablespoons unsalted butter at room temperature
  • 2 large eggs
  • ¾ cup organic buttermilk
  • teaspoons pure vanilla extract
  • 10 maraschino cherries vanilla ice cream for serving


Position an oven rack in the center of the oven. Preheat the oven to 350°F. Lightly coat an 8-inch round cake pan with nonstick cooking spray.

For the topping: In a 12-inch skillet, combine the water, light and dark brown sugars, and vanilla bean. Bring to a gentle boil over medium-high heat and cook, stirring until the sugar is completely dissolved. Reduce the heat to medium-low, add the pineapple slices, and sauté each side for about 3 to 5 minutes, or until lightly browned. Using a slotted metal spatula, carefully transfer the slices to a plate and let cool. Cook the sugar mixture in the pan to reduce to about cup. Remove from the heat and stir in the butter and coconut rum. Remove the vanilla bean and set the syrup aside.

For the batter: In a stand mixer fitted with the paddle attachment, combine all the dry ingredients and mix on low speed to blend. Add the butter and mix on low speed until blended. Add the eggs and beat on medium-high speed for 1 minute, or until light and fluffy. With the machine running, gradually add the buttermilk and beat until blended, stopping to scrape down the sides of the bowl once or twice. Add the vanilla and beat for 1 minute more. Set aside.

Arrange four of the pineapple slices in the bottom of the prepared pan. Cut the remaining slices in half to make half-moons and arrange them around the edges of the pan, curved-side up, gently pressing the slices so they stick to the sides. Place a maraschino cherry in the center of each of the four pineapple slices lining the bottom of the pan. Cut the remaining cherries in half. Place one half in the arch of the half slices, being careful to have the cut side of the cherries facing the inside of the pan. Pour the sugar syrup over the pineapple slices lining the bottom of the pan. Quickly pour the batter over the pineapples and cherries. Smooth the surface with an offset spatula. Bake for 45 to 55 minutes, or until the cake is lightly browned and a toothpick inserted in the center comes out clean.

Remove from the oven and let cool for 2 to 3 minutes. Gently run a knife around the edge of the pan. Unmold onto a serving plate and let cool for 15 minutes before slicing. Cut into wedges and serve warm or at room temperature, with vanilla ice cream.

Store, lightly covered, on the counter for up to 2 days or refrigerate for up to 1 week.