Pineapple Upside-Down Cake

Tender vanilla cake bakes over pineapple rings and a buttery brown sugar layer, then turns out warm with a glossy caramelized fruit topping.

90 min

8 slices

Ingredients

1/4 cup unsalted butter, for the topping

1/2 cup packed light brown sugar

7 pineapple rings, drained and patted dry

8 maraschino cherries, drained and patted dry (optional)

1 1/2 cups all-purpose flour

1 1/2 teaspoons baking powder

1/2 teaspoon kosher salt

6 tablespoons unsalted butter, softened

3/4 cup granulated sugar

2 large eggs, at room temperature

1 1/2 teaspoons vanilla extract

1/2 cup whole milk, at room temperature

9-inch round cake pan · Small saucepan · Mixing bowls · Hand mixer or stand mixer · Whisk · Thin knife · Serving plate

Dry the pineapple

Blot the rings well after draining; excess juice thins the brown sugar topping and can keep the cake from releasing neatly.

Serve the glossy side up

Let the cake cool until just warm so its crumb settles while the caramelized fruit remains soft and fragrant.

01. Heat the oven to 350 F and lightly butter only the sides of a 9-inch round pan so the topping can form on the bottom.

02. Melt 1/4 cup butter over low heat, stir in 1/2 cup brown sugar, and spread the glossy paste across the pan bottom.

03. Arrange 7 dry pineapple rings over the sugar. Add the 8 optional cherries to the centers, then pat away any pooled juice.

04. Whisk flour, baking powder, and salt together until the leavening is evenly dispersed.

05. Beat softened butter and granulated sugar until pale and fluffy, then scrape the bowl so no dense butter remains at the bottom.

06. Beat in the eggs one at a time, letting each disappear before adding the next, then mix in the vanilla until smooth.

07. Mix in the dry ingredients in three portions, alternating with milk in two portions. Stop as soon as the final flour streak disappears.

08. Spread batter gently over the fruit and all the way to the pan edges without shifting the rings.

09. Bake at 350 F for 40 to 45 minutes, until the cake springs back and a tester inserted in the cake comes out clean.

10. Rest 10 minutes, loosen the edge, and invert onto a serving plate while warm. Lift the pan straight up, then cool 10 minutes before slicing.