Chef notes

The ultimate upside down cake is that of the pineapple variety. And although it might seem tricky to assemble a cake where there is flipping involved, pineapple upside down cakes couldn’t be easier to make. What other cake offers up bronzed caramel, yellow pineapples and bright red maraschino cherries all in one go? The answer is none.

In this easy recipe, the melted butter and brown sugar topping is assembled right in the pan. To make it, sprinkle the bottom of the pan with the sugar, top it with thinly sliced butter and melt the two together in the oven before adding the fruit and batter. After you decoratively top the caramel with pineapple slices and cherries, the whole shebang gets chilled while you assemble the batter, which helps set the caramel and fruit “design,” resulting in a perfect looking pineapple upside down cake.

The batter is super moist, thanks to the use of oil rather than butter. Since there is butter in the topping, we promise you’ll get plenty of rich flavor. Buttermilk provides the cake with tang and tenderness and because some of the pineapple juice makes its way into the cake, too, you are guaranteed a wonderfully fruity cake.

Upside down cakes are such an easy and impressive way to showcase fruit (and your baking prowess). Once you bake this cake, expect your friends and family to ask for it again and again.

Technique Tips:

Thinly slice the butter for the caramel, so that you can evenly cover the brown sugar with it prior to melting the two in the oven. This ensures the butter and sugar will combine nicely while they cook.

Drying the pineapple and cherries with paper towels before placing them on the caramel, will remove some of the moisture, protecting against a soggy topped cake.

Purchase pineapple slices in juice, not heavy syrup, as you will be using some of the juice in the cake for extra flavor.

Cut two extra pineapple slices in half and use them around the edges of the cake, squeezing them a bit to make them fit, if necessary.

When slicing the cake, use a serrated knife and a sawing motion as it can be hard to cut through the pineapple.

Swap Option: You may substitute melted and cooled butter for the oil in the cake and you may substitute whole cherries, for the sliced ones called for here.

Ingredients

For the Topping

1/2 cup light brown sugar
3/4 teaspoon kosher salt
4 tablespoons unsalted butter, thinly sliced

7 pineapple slices in pineapple juice
15-20 sliced maraschino cherries

For the Cake

1/2 cup oil
1 cup granulated sugar
2 teaspoons pure vanilla extract
1 large egg
1 large egg yolk

3/4 cup buttermilk
1/4 cup pineapple juice
3/4 teaspoon baking powder
3/4 teaspoon kosher salt
1½ cups all-purpose flour

Fulfilled by

Preparation

Heat the oven to 350 F. Evenly sprinkle the brown sugar and salt over the bottom of a 9-by-2-inch ungreased round cake pan. Arrange the butter slices over the sugar in an even layer. Place the pan in the oven to melt the butter, 2 to 3 minutes.

Meanwhile, blot the pineapple slices and cherries with paper towels to dry. Carefully remove the pan from the oven and decoratively place the pineapple slices over the melted butter and sugar. Place the maraschino cherries in the center of each slice and in other empty spots between the pineapple slices. Chill in the refrigerator while you make the batter.

In a large bowl, whisk together the oil, sugar and vanilla. Add the egg and yolk and whisk to combine, then add the buttermilk and pineapple juice. Whisk in the baking powder and salt. Gently fold in the flour just until the last streak of it disappears. The batter will be lumpy. Scrape the batter into the pan so that it covers the pineapple.

Bake for 40 to 50 minutes, rotating at the halfway point, until a cake tester comes out with a moist crumb or two. Immediately run a butter knife around the edge of the pan. Let sit for 5 minutes and then carefully invert the cake onto a serving platter. If bits of caramel, pineapple or cherries stick to the bottom of the pan, scrape them off and place them back onto the cake.

Let cool until the caramel sets a bit, about 20 minutes, or to room temperature. Serve with vanilla ice cream or whipped cream.

The cake will keep wrapped in plastic wrap on the counter for up to 3 days, but it is best the day it is made.