Pineapple Upside Down Cake With Black Cherries

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Some desserts just feel like a celebration the moment you flip them out of the pan, and this one is exactly that.

The glossy caramelized fruit, the deep jewel tones from the cherries, and that soft, buttery cake underneath – it’s one of those bakes that always gets a little “wow” when you bring it to the table.

Pineapple Upside Down Cake With Black Cherries - easy upside down pineapple cake made with a freshly stewed black cherry, caramelized brown sugar, butter and pineapple topping and classic white cake batter.

I love making this Pineapple Upside Down Cake with Black Cherries when I want something classic but just a bit more special.

It’s cozy, a little nostalgic, and honestly… hard to stop at one slice.

How To Make This Pineapple Upside Down Cake With Black Cherries

Ingredients You’ll Need For This Recipe

For the topping:

3 tablespoons unsalted butter
½ cup brown sugar
3 tablespoons rum (optional)
1½ cups frozen black cherries
6–9 canned pineapple slices

For the batter:

1½ cups all-purpose flour
1 teaspoon baking powder
¼ teaspoon baking soda
½ teaspoon salt
3 ounces butter, softened
¾ cup granulated sugar
2 eggs
3 ounces sour cream
1 teaspoon vanilla extract
¼ cup pineapple juice
2 tablespoons milk

For serving (optional):

¾ cup heavy whipping cream
2–3 tablespoons sugar

Step-by-Step Guide

1. In a medium saucepan over medium-high heat, melt the butter with the brown sugar.

2. Stir until the mixture begins to simmer and slightly caramelize, about 3-4 minutes.

3. Turn off the heat, stir in the rum (if using), and add half of the frozen cherries. Let it sit for a few minutes to slightly thicken.

4. Line the bottom of a 9-inch cake pan with parchment paper and lightly grease the sides. If using a springform pan, place it inside a larger lined baking tray because the springform pan WILL leak!

5. Pour the caramel mixture into the pan and spread it evenly, keeping most of the cherries toward the center.

6. Pat the pineapple slices dry and arrange them in a single layer over the caramel.

7. Fill the centers and gaps with cherries with the help of a small spoon.

8. Add a final pineapple round (or cut it to fit) in the middle and fill with cherries as well.

9. Cut three pineapple rounds in half and arrange the halves around the edges of the cake pan.

10. Place the prepared base in the refrigerator while you make the batter to let the topping set slightly.

11. Preheat the oven to 350°F.

12. In a bowl, whisk together the flour, baking powder, baking soda, and salt. Set aside.

13. Using a stand or hand mixer, beat the softened butter until light and fluffy.

14. Add the sugar and continue beating until well combined, scraping down the sides as needed.

15. Beat in the eggs until smooth, then mix in the sour cream and vanilla extract.

16. Add the dry ingredients to the wet mixture and continue to whisk manually until almost combined. Be gentle! You don’t want to overmix the batter.

17. Pour in the pineapple juice and milk, mixing gently until just incorporated.

18. Fold in the remaining cherries, and again, be careful not to overmix the batter.

19. Spoon the batter over the fruit layer and spread it evenly with a spatula.

20. Cover with foil and bake for 20–30 minutes until the center begins to set.

21. Reduce the oven temperature to 330°F, remove the foil, and bake for another 30–40 minutes until a toothpick inserted in the center comes out clean.

22. Let the cake cool for 15–20 minutes. Then, carefully invert it onto a serving plate and let it cool to room temperature before slicing.

23. Mix heavy whipping cream with sugar to dissolve it, then whip the cream into stiff peaks.

24. Serve each slice of cake with a generous dollop of whipped cream.

Important Recipe Notes

For a softer, lighter crumb, you can substitute cake flour for all-purpose flour. Alternatively, replace 3 tablespoons of flour with cornstarch and sift well.
Using only egg whites instead of whole eggs can also create a lighter texture.
A regular cake pan works best since the caramel topping can leak from a springform pan. If using one, always place it on a baking tray.
Lowering the oven temperature halfway through helps prevent over-browning while ensuring the center bakes through evenly.
This cake is best served fresh. If refrigerated, it will become denser and the fruit may lose some of its glossy appearance.
Leftovers can be stored in the refrigerator for up to 2–3 days (without whipped cream).