Pineapple Upside-Down Cake

The kitchen filled with this incredible buttery caramel smell while my grandmother stood by the oven, peering through the glass door like she was watching something magical happen. She pulled out this golden cake, flipped it over in one confident motion, and there it was that glossy pineapple ring pattern staring back like edible sunshine. I was eight years old and completely convinced that dessert could actually be a form of sorcery.

Last summer, I made this for a neighborhood potluck and watched three different people ask for the recipe before they even took their second bite. Someone actually gasped when I flipped the cake onto the serving platter, which I have to admit made me feel like I had some secret baking power I did not actually possess.

Ingredients

• 60 g (1/4 cup) unsalted butter: Melted in the pan to create that rich caramel base that holds everything together
• 150 g (3/4 cup) light brown sugar: Packed tight because this becomes the sticky glaze that makes the cake unforgettable
• 8 to 10 canned pineapple rings: Drained thoroughly so extra moisture does not make the cake soggy underneath
• 8 to 10 maraschino cherries: One nestled in each pineapple ring for that classic retro look
• 120 g (1/2 cup) unsalted butter: Softened to room temperature so it creams properly with the sugar
• 200 g (1 cup) granulated sugar: Creamed until fluffy to give the cake its tender crumb structure
• 2 large eggs: Added one at a time to fully incorporate into the batter
• 1 tsp vanilla extract: Pure vanilla makes such a difference in a simple cake like this
• 190 g (1 1/2 cups) all-purpose flour: Measured by spooning into the cup and leveling off for accuracy
• 1 1/2 tsp baking powder: Ensures the cake rises properly over all that fruit weight
• 1/2 tsp salt: Balances the sweetness and enhances all the flavors
• 120 ml (1/2 cup) whole milk: Alternated with the flour to keep the batter tender

Instructions

Preheat and prepare your pan:

Set your oven to 175°C (350°F) and grease a 23-cm (9-inch) round cake pan thoroughly, paying special attention to the sides

Create the caramel layer:

Melt 60 g butter directly in the bottom of your prepared pan, then sprinkle the brown sugar evenly over the melted butter

Arrange the fruit:

Place pineapple rings over the sugar mixture in a pleasing pattern and nestle a maraschino cherry in the center of each ring

Cream the butter and sugar:

In a mixing bowl, beat 120 g softened butter and granulated sugar until the mixture turns pale and fluffy, about 3 minutes

Add the eggs and vanilla:

Beat in the eggs one at a time, fully incorporating each before adding the next, then stir in the vanilla extract

Mix the dry ingredients:

In a separate bowl, whisk together the flour, baking powder, and salt until well combined

Combine wet and dry ingredients:

Add the flour mixture to the butter mixture in three additions, alternating with the milk and beginning and ending with the flour, mixing just until combined

Layer the batter:

Spoon the batter carefully over the arranged pineapple and smooth the top with an offset spatula

Bake to golden perfection:

Bake for 38 to 42 minutes until the cake is golden and a toothpick inserted in the center comes out clean

The dramatic flip:

Let the cake cool in the pan for exactly 10 minutes, run a knife around the edges, then confidently invert onto a serving plate

Pin It

My first attempt at this cake ended with half the pineapple still stuck to the pan because I got impatient and flipped it too soon. The cake still tasted incredible, but I learned that timing really is everything with the flip.

Getting The Fruit Layout Right

Spend a minute arranging your pineapple rings before you commit to the layout. I like to place one ring in the center and work outward in concentric circles, but any pattern that looks good to you will work perfectly once that caramel takes over.

Making It Ahead

This cake actually tastes even better the next day as the flavors meld together. Bake it up to 24 hours in advance, keep it covered at room temperature, and serve it slightly warmed if possible.

Serving Suggestions

A slice of this cake needs nothing more than a cup of coffee, but I have found that a dollop of lightly sweetened whipped cream makes it feel extra special. The contrast between the warm cake and cold cream is absolute perfection.

• Try swapping pecan halves for cherries if you want some crunch
• Fresh pineapple works but needs extra patting dry to avoid excess moisture
• Add a tablespoon of rum to the caramel for a grownup version

Pin It

There is something deeply satisfying about a dessert that looks so impressive but comes from such simple ingredients. Every time I make this, I think about how food connects us to memories and people we love.

Recipe FAQs

→ Can I use fresh pineapple instead of canned?

Yes, fresh pineapple works beautifully. Peel and core the pineapple, then slice it into rings. You may need to cook it slightly longer to achieve the same caramelization as canned pineapple, which contains natural juices that help the process.

→ How do I prevent the cake from sticking to the pan?

Generously grease your pan with butter and ensure the brown sugar is evenly distributed over the melted butter before adding the pineapple. Let the cake cool for exactly 10 minutes after baking before inverting—this allows the caramel to set slightly while still being warm enough to release easily.

→ Can I make this cake ahead of time?

This cake is best served the day it's made while still slightly warm, as the caramel topping stays glossy and the cake remains moist. However, you can store it at room temperature for up to 2 days, covered with plastic wrap or a cake dome. Warm individual slices in the microwave for 10-15 seconds to refresh.

→ What can I substitute for maraschino cherries?

Fresh or frozen pitted cherries, cranberry halves, or pecan halves make excellent alternatives. For a tropical twist, try placing macadamia nuts in the pineapple centers. The key is choosing something that contrasts beautifully with the golden pineapple rings.

→ Why did my cake turn out dense or dry?

Overmixing the batter can develop too much gluten, leading to a dense texture. Mix only until just combined after each addition. For dryness, ensure you're measuring flour correctly—spoon it into your measuring cup and level off with a knife rather than scooping directly, which compacts the flour.

→ Can I freeze pineapple upside-down cake?

Yes, freeze the completely cooled cake tightly wrapped in plastic wrap and foil for up to 3 months. Thaw overnight at room temperature before serving. Note that the texture is best when fresh, but frozen cake still maintains good flavor and moistness.