Classic Pineapple Upside-Down

My neighbor brought over a slice of pineapple upside-down cake one afternoon, still warm from her oven, and I was immediately transported back to my grandmother's kitchen where this dessert always felt like an occasion. The caramelized fruit was glossy and dark, the cake beneath it impossibly tender, and I realized I'd been missing something essential in my own kitchen. That first bite made me determined to master the technique, and now this cake appears whenever I want to turn an ordinary day into something golden and memorable.

I made this for my sister's birthday last spring, and she was genuinely shocked when I inverted the cake at the table. The pineapple rings caught the afternoon light like stained glass, each cherry sitting exactly where I'd placed it. She asked for the recipe before finishing her first slice, which felt like the highest compliment I could receive.

Ingredients

• Unsalted butter (60 g for topping, 120 g for cake): Use real butter, not margarine—it's the foundation of both the caramel and the tender crumb, and you'll taste the difference.
• Light brown sugar (150 g, packed): The packing matters because it gives you the moisture needed for proper caramelization on the cake bottom.
• Canned pineapple rings (8-10 pieces), drained: Canned is actually better here than fresh because the sugar has already done the work of softening and the acidity won't interfere with your bake.
• Maraschino cherries (8-10 pieces): They're sweetly artificial in the best way—save the fancy stuff for other cakes.
• Granulated sugar (200 g): This creates the light, fluffy crumb that contrasts beautifully with the sticky topping.
• Large eggs (2): Room temperature eggs blend more smoothly and create a more tender cake.
• Vanilla extract (1 tsp): Let it be a good quality—it's your main flavor note besides the caramel.
• All-purpose flour (190 g, 1 1/2 cups): Measure by spooning and leveling, not scooping, or you'll end up with a dense cake.
• Baking powder (1 1/2 tsp): This is what gives you the gentle rise—too little and the cake stays flat, too much and it peaks.
• Salt (1/2 tsp): Even in a sweet cake, salt makes everything taste more like itself.
• Whole milk (120 ml): The dairy tenderizes the crumb and creates a more delicate structure than water would.

Instructions

Prep your pan and create the caramel base:

Heat your oven to 175°C (350°F) and get a 23-cm round cake pan ready with a light grease. Melt the butter in a small pan over medium heat, then pour it directly into the bottom of your cake pan—you want an even coating. Sprinkle the packed brown sugar over the butter and press it down gently with the back of a spoon until it looks like wet sand. This mixture will bubble and caramelize as it bakes, becoming pure gold.

Arrange the fruit crown:

Working carefully, lay each pineapple ring over the sugar mixture, spacing them evenly and leaving room for the cherries. Place one cherry in the center of each ring—they'll sink slightly into the pineapple as it bakes, which is exactly what you want.

Cream your butter and sugar:

In a large bowl, beat the softened butter and granulated sugar together for about two minutes until the mixture looks pale, light, and fluffy—this is crucial because you're incorporating air that makes the cake tender. You'll know it's ready when it's almost the color of frosting.

Build the batter foundation:

Add eggs one at a time, beating well between each addition so they fully incorporate. Add the vanilla extract and beat until the mixture is smooth and creamy—don't rush this step.

Combine dry ingredients:

In a separate bowl, whisk the flour, baking powder, and salt together, breaking up any lumps of baking powder so it distributes evenly. This whisking step prevents the dense, gritty texture that happens when you use a fork.

Bring it all together:

Add the flour mixture to the butter mixture in three additions, alternating with the milk and starting and ending with flour—this technique prevents overworking the batter. After each addition, fold gently until just combined, stopping as soon as you don't see white streaks of flour anymore.

Layer and bake:

Spoon the batter carefully over the fruit, spreading it gently and smoothly with a spatula—it will seem thin, but it puffs as it bakes and should reach the edges and fruit without disturbing the arrangement. Bake for 38 to 42 minutes until the top is golden and a toothpick inserted in the center comes out clean.

The moment of truth:

Let the cake cool in the pan for exactly 10 minutes—this is long enough for the caramel to set slightly but short enough that it's still pliable. Run a thin knife around the edges to loosen it completely, then place your serving plate on top, take a deep breath, and flip it over in one confident motion.

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I once served this cake to someone who had only ever eaten store-bought desserts, and watching their face when they tasted the homemade butter and that caramelized pineapple was worth every minute of the baking time. That's when I understood this cake isn't just about flavor—it's about showing up for people with something made by your own hands.

Variations That Work

Add 1 to 2 tablespoons of the pineapple juice directly to the batter before pouring it over the fruit—it deepens the vanilla flavor with a subtle tropical brightness without making the cake taste tropical. You can also swap the maraschino cherries for whole pecans if you want something less sweet and more sophisticated, or arrange a mix of both for texture contrast. Fresh pineapple works beautifully too, though it releases more liquid, so pat it extra dry with paper towels before arranging it in the pan.

Serving and Storage

Serve this cake warm or at room temperature alongside whipped cream or vanilla ice cream—the cold contrast against the warm cake is intentional and necessary. The cake stays fresh and moist for three days covered loosely on the counter, and individual slices reheat gently in a 160°C oven for about eight minutes if you want that fresh-from-the-oven warmth again.

The Perfect Pairing

This is the cake you bring to potlucks because it travels well and always looks showstopping when you invert it right there at the table. Serve it with strong black coffee, weak tea, or even champagne—the sweetness and richness pair beautifully with something to cut through it.

• Make sure your serving plate is at least 25 cm across so there's room for the caramel that pools around the cake.
• If the caramel sticks to the pan, return the whole thing to a warm oven for two minutes and try again—heat helps it release.
• This cake is forgiving enough to make twice—once as a test run, once for an audience.

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This cake has been in my rotation for years now, and it never fails to feel like an occasion. There's something about that moment when you flip the pan and see the golden fruit emerge that makes the whole baking process feel worthwhile.

Recipe FAQs

→ How do I achieve a caramelized pineapple topping?

Start by melting butter and sprinkling brown sugar evenly in the pan before arranging pineapple rings. The sugar caramelizes during baking, creating that rich topping.

→ Can fresh pineapple be used instead of canned?

Yes, fresh pineapple works well. Just be sure to drain excess juice or lightly pat dry to prevent sogginess.

→ What is the best pan size for this cake?

A 23-cm (9-inch) round pan is ideal for even baking and the perfect presentation of the upside-down topping.

→ How do I know when the cake is done baking?

Insert a toothpick into the center; it should come out clean when the cake is fully baked. Baking time ranges from 38 to 42 minutes.

→ What serving suggestions complement this cake?

It pairs beautifully with whipped cream or vanilla ice cream for added creaminess and balance.