Buttery Vanilla Pineapple Cake

There's something almost magical about the moment you invert a pineapple upside-down cake onto a plate and that caramelized topping catches the light like edible stained glass. I discovered this cake during a particularly chaotic summer when my neighbor brought one to our block party, and I watched grown adults literally stop mid-conversation to taste it. The buttery vanilla sponge underneath that jewel-toned crown of pineapple and cherries felt simultaneously comforting and fancy, which made me desperate to figure out if I could actually pull it off in my own kitchen.

I made this cake for a dinner party where I promised something impressive, then immediately panicked because I'd never inverted anything more delicate than a tart. My hands were genuinely shaking when I ran that knife around the edges and flipped the pan over, but the moment that golden, glossy top landed perfectly on the plate, I felt like I'd just performed a magic trick. My guests actually applauded, which felt ridiculous and wonderful all at once.

Ingredients

• Unsalted butter (60 g for topping, 120 g for cake): This is your flavor foundation, so don't skimp on quality. The topping butter melts into a caramel base that captures the brown sugar, while the softened cake butter creams beautifully to trap air and keep the cake tender.
• Light brown sugar (150 g for topping): Brown sugar brings molasses depth that white sugar can't match, and it caramelizes into that glossy, slightly chewy layer everyone fights over.
• Granulated sugar (200 g for cake): This sweetens the batter evenly and helps create the fine crumb structure you want.
• Canned pineapple rings (8-10): Canned is actually your friend here because fresh pineapple's enzymes can interfere with rising. Make sure you drain them well or you'll end up with a soggy bottom layer.
• Maraschino cherries (8-10): These are pure nostalgia, bright and sweet. Position one dead center in each pineapple ring for maximum visual impact.
• Large eggs (2): These bind everything and add richness. Room temperature eggs emulsify better, so let them sit on the counter while you prep.
• Vanilla extract (1 tsp): Use real vanilla, not the imitation stuff. One teaspoon is enough to flavor the cake without making it taste overly perfumed.
• All-purpose flour (190 g): Measure by spooning into your measuring cup and leveling, not by scooping directly from the bag, or you'll pack it too tight and end up with a dense cake.
• Baking powder (1 1/2 tsp): This is your rising agent. Make sure it's fresh, not something lurking in the back of your cabinet from two years ago.
• Salt (1/2 tsp): Don't skip this. Salt amplifies sweetness and balances all the rich butter and sugar.
• Whole milk (120 ml): The milk keeps the crumb tender and moist. Room temperature milk incorporates more smoothly into your batter.

Instructions

Set up and preheat:

Get your oven to 175°C (350°F) and grease your 23-cm cake pan thoroughly, making sure to get into the corners. This matters because the caramelized sugar sticks surprisingly easily.

Create the caramel base:

Melt 60 g of butter over low heat, pour it into the bottom of your pan, then scatter that packed brown sugar over it evenly. Don't stir it yet; you're building layers.

Arrange your pineapple crown:

Lay those drained pineapple rings directly on top of the sugar mixture, leaving space between them if you can. Nestle a maraschino cherry into the center of each ring so it looks absolutely intentional and gorgeous.

Cream the cake base:

In a mixing bowl, beat 120 g of softened butter and 200 g of granulated sugar until the mixture is pale, fluffy, and noticeably lighter than when you started. This takes about three to four minutes and is where you're trapping air that makes the cake rise.

Add eggs and vanilla:

Drop in one egg at a time, beating well after each addition so everything emulsifies properly. Then add your vanilla extract and mix until combined.

Combine dry ingredients:

In a separate bowl, whisk together your flour, baking powder, and salt so the leavening distributes evenly throughout the flour.

Alternate wet and dry:

Add the flour mixture to your batter in three additions, pouring in milk between each flour addition and starting and ending with flour. Stir until just combined; overmixing develops gluten and makes the cake tough, so stop when you no longer see streaks of flour.

Layer and smooth:

Spoon the batter gently over your pineapple arrangement, smoothing the top with a spatula so it's level. Be gentle so you don't dislodge those carefully placed rings.

Bake to golden perfection:

Slide into the oven for 38 to 42 minutes. The cake is done when a toothpick inserted into the center comes out clean or with just a few moist crumbs, not wet batter.

Cool and invert:

Let the cake rest in the pan for 10 minutes, then run a thin knife carefully around the edges to loosen it from the sides. Place your serving plate on top of the pan and flip everything in one confident motion, then carefully lift away the pan. If it doesn't come away cleanly, you can give it a gentle tap or run a warm cloth over the bottom to loosen it.

Save

The best moment was when my five-year-old cousin tasted this cake at a family dinner and got so quiet that everyone stopped talking to see what was wrong, and then she just whispered that it tasted like fruit candy mixed with cake and could she please have more. That's when I realized this isn't just a showoff dessert; it's genuinely delicious in a way that makes people actually happy.

The Caramel Magic

The real secret to an incredible pineapple upside-down cake lives in those first ten minutes while the caramel forms and the edges start to set. Watch it through the oven window if you can, because once the edges turn deep amber gold and you smell that sweet, toasty caramel scent filling your kitchen, you know something special is happening. The pineapple juices mingle with the melting brown sugar and butter to create this glossy, almost candy-like layer that transforms from solid sugar and fruit into something sticky and irresistible.

Serving and Storage

This cake tastes wonderful warm from the oven with a scoop of vanilla ice cream melting on top, but it's also genuinely good at room temperature the next day, which makes it ideal for bringing to potlucks or keeping on hand for unexpected cravings. It stays moist for about three days if you cover it loosely with foil, and honestly, it rarely lasts that long in most households. You can also serve it with whipped cream if ice cream feels too heavy, or pair it with a cup of strong coffee for a simple but elegant dessert.

Creative Variations Worth Trying

Once you master the classic version, you can start experimenting without losing what makes this cake so special. Adding a tablespoon or two of pineapple juice to the batter gives you an extra whisper of tropical flavor that feels both subtle and unmistakably intentional. Some people skip the maraschino cherries entirely and fill the pineapple centers with pecans for a nuttier, less sweet vibe, or they layer peach slices under the rings for something warmer and earthier. You could even brush the pineapple rings with a tiny bit of rum before baking if you want to serve this to adults and give it a sophisticated edge.

• Try adding 1 to 2 tablespoons of pineapple juice directly into the cake batter for subtle tropical depth.
• Substitute fresh or frozen pineapple if you want, but make sure to pat it completely dry so you don't end up with excess moisture.
• Swap the cherries for pecans, almonds, or even candied ginger if you want to steer the flavor in a totally different direction.

Save

This cake has somehow become the dessert I make when I want to feel competent and generous at the same time, and that's worth something. It never fails to get genuine reactions, and honestly, that's the real magic.

Recipe FAQs

→ How do I achieve caramelized pineapple topping?

Melt butter and brown sugar in the pan, then layer pineapple rings over the mixture before adding batter. This creates a rich caramel layer after baking.

→ Can fresh pineapple be used instead of canned?

Yes, fresh pineapple can be substituted, but drain well to avoid excess moisture affecting the texture.

→ What is the best way to invert the cake after baking?

Allow the cake to cool for 10 minutes, run a knife around the edges, then place a serving plate on top and flip swiftly to maintain the topping arrangement.

→ Can pecans replace cherries in the topping?

Yes, pecans add a pleasing crunch and a nutty contrast to the sweet pineapple and caramel layers.

→ How should the cake be stored after baking?

Keep the cake covered at room temperature for up to two days or refrigerate, bringing to room temperature before serving for best flavor.

→ Does adding pineapple juice affect the cake texture?

Adding 1–2 tablespoons of pineapple juice to the batter enhances flavor without altering the tender crumb noticeably.