I had been meaning to bake a pineapple upside down cake for years, and I’m so glad I finally made it. This version is incredibly moist — the crumb practically melts in your mouth. Caramelized pineapple slices sit on top of a tender, buttery vanilla cake, producing a classic combination of sweet, fruity and buttery flavors.
The cake stays moist because the batter uses oil and buttermilk. You can substitute butter for the oil if you prefer, but oil keeps vanilla cakes extra tender and makes a noticeable difference in texture.
To prepare the pan, melt butter and pour it into the cake pan, then sprinkle light brown sugar over the butter to form the caramel base. Arrange pineapple slices over the sugar — traditionally a ring in the center and rings around the edges — and place maraschino cherries in the centers or between slices for color and a pop of flavor. I like to place one whole ring in the center and cut the remaining rings to fan around the edges, tucking cherries between slices for a decorative finish.
I mixed the cake batter separately, then poured it carefully over the arranged pineapple and cherries so nothing shifts. As the cake bakes, the butter and sugar bubble and create a glossy, buttery glaze that soaks into the edges and keeps the cake rich and moist.
When the cake is finished baking, allow it to cool for about 30 minutes. Invert the pan directly onto a serving plate or cake stand. Because of the buttery topping, the cake usually releases easily and the pineapple and cherries become the cake’s top once flipped.
This is a cheerful spring or summer cake: fruity, bright and comforting. It’s at its best warm from the oven, when the glaze is still glossy and the cake is tender. I don’t usually add whipped cream; the cake is flavorful enough on its own. If you want, serve warm slices with a scoop of vanilla ice cream for a classic pairing.
Serve warm with vanilla ice cream on the side for an indulgent finish.
Method
Make the cake batter
In a bowl, sift together the all-purpose flour, granulated sugar, baking powder, baking soda and salt. In a separate bowl, whisk the wet ingredients: the egg, buttermilk, vanilla extract, pineapple juice and oil. Add the dry ingredients to the wet ingredients in three additions, whisking until just combined. Do not overmix to preserve a tender crumb.
Make the topping
Melt the butter and pour it into a 9 x 2 inch round cake pan. Sprinkle the brown sugar evenly over the melted butter. Place one pineapple ring in the center of the pan and arrange the remaining slices around it; if desired, cut slices and fan them around the center. Tuck maraschino cherries in between the pineapple slices for contrast and visual appeal. Carefully pour the prepared cake batter over the fruit and cherries, taking care not to move them.
Place the pan on a cookie sheet to catch any drips, and bake in a preheated oven at 350°F (175°C) for about 40 minutes, or until a toothpick inserted into the center comes out clean. Remove the cake from the oven and allow it to cool for 30–40 minutes before inverting onto a serving plate. The buttered sugar will have formed a glossy sauce that coats the pineapple and the cake.
Ingredients
Topping
- 5 tablespoons unsalted butter, melted
- 1/2 cup light brown sugar
- 7 pineapple slices (canned or fresh), drained
- 12 maraschino cherries (optional, but recommended)
Cake
- 1 1/4 cups all-purpose flour
- 1 teaspoon baking powder
- 1/4 teaspoon baking soda
- 1/4 teaspoon salt
- 1 cup granulated sugar
- 5 tablespoons oil (canola or neutral oil)
- 1/2 cup buttermilk
- 1/4 cup pineapple juice
- 1 egg, at room temperature
- 2 teaspoons vanilla extract
Instructions
Cake batter
- Sift together the flour, granulated sugar, baking powder, baking soda and salt. Set aside.
- Whisk together the egg, buttermilk, vanilla, pineapple juice and oil in another bowl.
- Add the dry ingredients to the wet in three additions, mixing gently until just combined. Stop as soon as the batter is uniform.
Topping and assembly
- Melt the butter and pour it into a 9 x 2 inch round cake pan. Sprinkle brown sugar evenly over the butter.
- Place one pineapple ring in the center and arrange remaining slices around it; add cherries between slices if using.
- Carefully pour the batter over the fruit, making sure not to displace the arrangement.
Bake
- Place the pan on a cookie sheet and bake at 350°F (175°C) for about 40 minutes or until a toothpick inserted into the center comes out clean.
- Allow the cake to cool for 30–40 minutes, then invert the pan directly onto your serving plate so the pineapple becomes the top.
- Serve warm or at room temperature, with whipped cream or vanilla ice cream if desired.
Notes
- Cherries are optional but add color and a hint of flavor; you can omit them if preferred.
- Buttermilk contributes to a softer, more tender cake. If you don’t have buttermilk, make a substitute by adding 1 tablespoon lemon juice or vinegar to a cup measure, then top with milk to the 1 cup mark and let sit for 5 minutes before using; use the portion required in the recipe.
- Both canned and fresh pineapple work well; canned pineapple rings are convenient and consistent in size.
Pineapple Upside Down Cake
