Pineapple Upside-Down Cake

The kitchen filled with that unmistakable buttery caramel scent as I slid this cake into the oven, transporting me straight back to my grandmother's retro kitchen with its harvest gold appliances. I'd been searching for that perfect upside-down cake for years, one where the pineapple stays tender and the caramel stays gooey instead of crystallizing into something that sticks to your teeth. My first attempt ended up with half the fruit clinging stubbornly to the pan while my family watched in amused silence, but we ate every crumb anyway because the flavors were still incredible.

Last summer, I made this cake for my neighbor's potluck and watched three generations of her family light up when I brought out that beautiful golden ring of pineapple glistening on top. Her grandfather actually asked if I'd used his mother's secret recipe, which I took as the highest compliment possible. The cake disappeared within minutes, and I spent the rest of the afternoon writing down the recipe for three different relatives on whatever scraps of paper they could find.

Ingredients

• Unsalted butter: I use unsalted butter here because I want complete control over the saltiness in both the caramel topping and the cake batter itself
• Light brown sugar: The molasses in brown sugar creates that deep caramel flavor and keeps the topping gooey instead of hard and crunchy
• Canned pineapple rings: Canned pineapple works beautifully because it's already tender and packed in juice, but you can use fresh if you prefer a slightly firmer texture
• Maraschino cherries: These bright red centers make the classic presentation so striking and add a sweet pop of color that contrasts beautifully with the golden pineapple
• Granulated sugar: Creaming this with the butter creates the tender, fine crumb that makes this cake so light and buttery
• Large eggs: Room temperature eggs will incorporate better into your batter, creating better structure and a more uniform texture
• Vanilla extract: Pure vanilla extract enhances all the other flavors without competing with the pineapple and caramel
• All purpose flour: This provides the perfect structure for a cake that's sturdy enough to invert but still wonderfully tender
• Baking powder: The leavening agent that gives your cake its rise and ensures it's not dense or heavy
• Salt: Just enough to balance the sweetness and bring out all the flavors
• Whole milk: Whole milk creates a richer, more tender cake than low-fat alternatives

Instructions

Prepare your pan and preheat:

Set your oven to 175°C (350°F) and generously grease a 23-cm (9-inch) round cake pan with butter, getting into every corner and crevice.

Create the caramel layer:

Melt 60 g butter in your prepared pan, either in the microwave or in the oven as it preheats, then sprinkle the brown sugar evenly across the bottom.

Arrange the fruit:

Place pineapple rings in an attractive pattern over the sugar butter mixture, then nestle a maraschino cherry in the center of each ring.

Cream butter and sugar:

Beat 120 g softened butter and granulated sugar together until the mixture is pale yellow and fluffy, about 3 to 4 minutes with a mixer.

Add eggs and vanilla:

Beat in the eggs one at a time, fully incorporating each before adding the next, then mix in the vanilla extract until combined.

Mix dry ingredients:

In a separate bowl, whisk together the flour, baking powder, and salt until they're evenly combined.

Combine wet and dry:

Add the flour mixture to your batter in three portions, alternating with the milk and beginning and ending with the flour, mixing only until each addition is just incorporated.

Add batter to pan:

Carefully spoon the batter over the arranged pineapple, spreading it gently and evenly to avoid disturbing your fruit pattern.

Bake to golden perfection:

Bake for 38 to 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.

The moment of truth:

Let the cake cool in the pan for exactly 10 minutes, run a knife around the edges, place your serving plate over the pan, and confidently flip everything over at once.

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My daughter now requests this cake for every birthday, insisting that no celebration feels complete without that dramatic flip moment that reveals the beautiful fruit pattern. Last year, she started helping me arrange the pineapple rings and has developed quite an eye for creating the most visually stunning pattern possible.

Serving Suggestions That Shine

This cake needs nothing more than itself to be absolutely incredible, but a dollop of freshly whipped cream or a scoop of high-quality vanilla ice cream takes it over the top. I've also served it with crème fraîche when I want something slightly tangy to cut through all that sweetness.

Make It Your Own

While the classic version is hard to beat, you can swap pecan halves for the cherries or add a sprinkle of coconut to the brown sugar mixture for tropical vibes. Fresh pineapple works beautifully too, though I recommend briefly sautéing the rings in a little butter first to soften them up.

Storage And Make-Ahead Tips

This cake actually tastes even better the next day as the flavors meld together and the pineapple moisture seeps into the cake. Store it covered at room temperature for up to 3 days, though it rarely lasts that long in my house. You can also bake it a day ahead, keep it in the pan, and flip it just before serving for the freshest presentation.

• Wrap any leftovers tightly in plastic wrap to keep the cake from drying out
• Warm individual slices in the microwave for about 15 seconds to recreate that fresh-from-the-oven experience
• Don't refrigerate the cake unless absolutely necessary, as cold temperatures can make the caramel hard and the cake dense

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There's something utterly magical about that moment when you lift the pan and reveal those beautiful caramelized rings in all their glory, like unveiling a edible masterpiece you somehow created in your own kitchen.

Recipe FAQs

→ Can I use fresh pineapple instead of canned?

Yes, fresh pineapple works beautifully. Slice it into rings about 1/2 inch thick. You may need to cook it slightly longer to achieve proper caramelization since fresh pineapple contains more moisture than the canned variety.

→ Why did my cake stick to the pan?

Sticking usually happens if the butter and sugar mixture wasn't evenly distributed or the cake cooled too long before inverting. Always run a knife around the edges and invert within 10 minutes of removing from the oven while still warm.

→ How do I store leftovers?

Keep covered at room temperature for up to 2 days, or refrigerate for up to 5 days. The butter and sugar topping keeps the cake moist. Bring to room temperature before serving for the best texture and flavor.

→ Can I make this ahead of time?

Absolutely! Bake the cake up to 24 hours in advance. Once cooled and inverted, wrap tightly in plastic wrap. The flavors actually develop and improve overnight. Serve at room temperature or warm slightly before serving.

→ What can I substitute for maraschino cherries?

Fresh or frozen pitted cherries work well. For a nutty variation, place pecan halves in the pineapple centers instead. You could also use crushed pineapple between the rings for extra fruitiness throughout.