Pineapple Upside-Down Cake

You can make upside-down cakes with all kinds of fruit, but you just can’t beat our take on the classic. We make it in a cast-iron skillet and add bourbon to the salted-caramel pineapple topping. Sprinkle in almonds for added flavor and texture.

Back in the Day Bakery Made with Love

For the Caramel Pineapple Topping

• 1 pineapple

• 6 tablespoons unsalted butter

• 1 cup packed light brown sugar

• 1 tablespoon bourbon (rum or vanilla works too)

• 1/2 teaspoon fine sea salt

• 3/4 cup sliced almonds, toasted 

For the Cake

• 1 1/3 cups cake flour (not self-rising)

• 2 teaspoons baking powder, preferably aluminum-free

• 3/4 teaspoon ground cinnamon

• 1 teaspoon ground ginger

• 1 teaspoon fine sea salt

• 2 large eggs, at room temperature

• 2 teaspoons pure vanilla extract

• 1 cup granulated sugar

• 8 tablespoons (1 stick) unsalted butter, at room temperature

• 1 cup sour cream

Special Equipment

• One 1-inch round cookie cutter

• Preheat the oven to 350°F. 

1. To prepare the pineapple: Slice off the top and bottom of the pineapple to create easy-to-manage flat surfaces. Stand the pineapple up and slice the skin away in long strips following the contours of the fruit, making sure to remove all of the brown eyes. Put the peeled pineapple on its side and cut into 1/2-inch-thick rounds. Using a 1-inch cookie cutter, remove the core from each slice. Set the pineapple aside on paper towels.

2. To make the caramel topping: Melt the butter in a 10-inch cast-iron skillet over medium heat, or melt it in a 10-inch round cake pan over low heat. Sprinkle the brown sugar, bourbon, and salt over it and cook, stirring occasionally, until the sugar dissolves and the caramel is golden, about 3 minutes. Remove from the heat.

3. Arrange the sliced pineapple in a circle on top of the caramel mixture, without overlapping the rings, then fill in the center; you can cut the remaining pieces to fill in the gaps if you like. Sprinkle with the toasted almonds.

4. To make the cake batter: In a medium bowl, whisk together the flour, baking powder, cinnamon, ginger, and salt. Set aside.

5. In a small bowl, whisk the eggs and vanilla together. Set aside.

6. In the bowl of a stand mixer fitted with the paddle attachment (or in a large mixing bowl, using a handheld mixer), cream the sugar and butter together on medium-high speed for 3 to 5 minutes, until light and fluffy. Gradually add the eggs and vanilla, beating well and scraping down the sides of the bowl with a rubber spatula as necessary, then beat until doubled in volume, about 2 minutes.

7. Turn the mixer speed down to low and add the flour mixture in thirds, alternating with the sour cream and beginning and ending with flour.

8. Remove the bowl from the mixer and use the rubber spatula to incorporate any ingredients hiding at the bottom of the bowl, making sure the batter is completely mixed. Pour the batter over the pineapple and smooth it with a spatula.

9. Bake for 50 to 60 minutes, until a cake tester inserted in the center of the cake comes out clean. Let the cake cool in the skillet or cake pan for about 30 minutes.

10. Run a small knife around the edges of the skillet or pan, then place a large serving plate upside down on top and invert the skillet or pan to release the cake onto the plate. Serve warm or at room temperature.

The cake can be stored in an airtight container at room temperature for up to 3 days.