Classic Pineapple Upside-Down

My aunt pulled this cake from her oven on a Sunday afternoon, and the kitchen filled with this buttery-caramel perfume that made everyone stop talking. When she flipped it onto a plate and those golden pineapple rings emerged like stained glass, I understood why this dessert has survived every food trend since the 1950s. There's something almost magical about baking a cake upside down and having it arrive at the table like a gift you didn't know you were waiting for.

I made this for a potluck once and brought it still warm, wrapped in foil, not knowing if it would survive the car ride. When I set it down and lifted the cover, everyone leaned in at the same time, and someone said "Oh wow" in that tone that meant I'd actually pulled it off. That's when I realized this cake does the impressing for you.

Ingredients

• Unsalted butter (for topping): Use quality butter here since the caramel is the star; it'll melt into a glossy amber pool that catches the light.
• Light brown sugar: This is what turns butterscotch-colored and sticky when it meets heat, so don't skip it for regular white sugar.
• Canned pineapple rings: Fresh pineapple releases too much juice and throws off the topping, so stick with canned and drained well.
• Maraschino cherries: They look bright and cheerful in the center of each ring; you could swap for pecans or walnuts if you want texture.
• Softened butter (for cake): Take it out of the fridge 20 minutes early so it creams properly and won't leave lumps in your batter.
• Granulated sugar and eggs: The foundation of a tender crumb that won't dry out during baking.
• Vanilla extract: A teaspoon sounds small, but it's what makes the cake taste like home instead of like flour.
• All-purpose flour, baking powder, and salt: Sift or whisk these together to break up any lumps so your cake rises evenly.
• Whole milk: The acidity helps create a more delicate, moist texture in the finished cake.

Instructions

Set your stage:

Preheat the oven to 175°C (350°F) and grease your 23-cm round pan thoroughly, paying special attention to the sides. You want no stuck spots when you flip this.

Make the caramel base:

Melt the 60 g of butter and pour it into the bottom of the pan, then sprinkle the brown sugar evenly across it. The mixture should look wet and a bit loose—it'll set as it bakes.

Arrange the topping:

Place pineapple rings in a pretty pattern, overlapping slightly if needed, and nestle a cherry in the center of each one. This is your moment to make it look beautiful because this side becomes the top.

Cream the butter and sugar:

Beat the softened butter and granulated sugar together for about 2–3 minutes until it looks pale and fluffy, like clouds. This step adds air to the cake and makes it tender.

Add eggs and vanilla:

Add the eggs one at a time, beating well after each addition, then stir in the vanilla extract. The batter should look smooth and slightly thick.

Combine the dry ingredients:

In another bowl, whisk the flour, baking powder, and salt together to break up any lumps and distribute the leavening evenly. This prevents dense pockets in your cake.

Build the batter:

Add the flour mixture to the wet ingredients in three parts, alternating with splashes of milk and starting and ending with flour. Stir just until combined—overmixing toughens the cake.

Spread over pineapple:

Gently spoon the batter over the arranged pineapple rings and smooth the top with a spatula, being careful not to nudge the fruit underneath. The batter should spread easily and level itself slightly as it bakes.

Bake to golden:

Bake for 38–42 minutes until the top is golden brown and a toothpick inserted in the center comes out clean or with just a few moist crumbs. If the top browns too quickly, tent it loosely with foil.

The flip moment:

Cool in the pan for exactly 10 minutes—this lets the caramel set just enough to stick to the cake without cooling so much that it hardens. Run a thin knife around the edges and invert onto a serving plate in one confident motion.

Save

There's a moment right when you flip this cake where your heart skips because you're trusting that thin layer of caramel to stay put. When it does, and those rings emerge intact and gleaming, it feels like you've done something clever. That's the moment this cake transforms from ingredients into something that feels worth the effort.

Why the Inversion Works

Upside-down cakes are built backward on purpose—the fruit and topping bake on the bottom, and when you flip, they become the glamorous top layer. The gentle heat keeps everything in place, and the caramel acts like edible glue. By the time you invert, the timing is perfect: the cake is set enough to support the weight but warm enough that flavors are still mingling.

Timing and Temperature Matter

This cake is forgiving with most things, but oven temperature is not one of them. If your oven runs hot, it might bake in 35 minutes; if it runs cool, it could need 45. Invest in an oven thermometer if you haven't already—it's the difference between a moist cake and one that's overdone at the edges. And yes, those extra 2–3 minutes in the cooling pan make the difference between a triumphant flip and a caramel-collapse moment.

Serving and Variations

Serve this cake warm or at room temperature with whipped cream or vanilla ice cream—both disappear into the caramel and make each bite feel decadent. You can experiment without losing the soul of the dessert: add a tablespoon of pineapple juice to the batter for subtle tropical notes, swap the cherries for pecans for crunch, or use fresh pineapple if you cook it first to draw out excess moisture.

• A tiny splash of rum extract in the batter echoes the retro elegance without making it boozy.
• Dust the top with a pinch of fleur de sel just before serving to make the caramel taste even more complex.
• This cake actually tastes better the next day once the flavors have settled.

Save

This cake reminds us that sometimes the best desserts are the ones that have stood the test of time, refined by countless home bakers rather than chefs. Bake it once and you'll understand why.

Recipe FAQ

→ How do I achieve caramelized pineapple topping?

Melt butter and sprinkle brown sugar evenly at the pan's base, then arrange pineapple rings on top before adding the batter. Baking melts the sugar, caramelizing the fruit.

→ Can fresh pineapple be used instead of canned?

Yes, fresh pineapple slices work well but may release more juice, so adjusting baking time slightly can help maintain texture.

→ What cake pan size is recommended?

A 23-cm (9-inch) round cake pan ensures even cooking and proper thickness of the cake.

→ How can I tell when the cake is done baking?

Insert a toothpick into the center; it should come out clean or with a few moist crumbs when fully baked.

→ What variations can enhance the flavor?

Adding pineapple juice to the batter or replacing cherries with pecans can add depth and a contrasting texture.