Pineapple Upside-Down Cake

The smell of brown sugar melting into butter always stops me in my tracks, no matter how many times I make this cake. My grandmother used to let me arrange the pineapple rings perfectly centered, though I always snuck a cherry or two while she wasn't looking. There's something almost magical about flipping that pan over and revealing the glossy, caramelized fruit staring back at you like little golden suns.

I made this for a potluck last spring and watched three different people ask for the recipe before they'd even taken their first bite. Someone actually gasped when I turned it out onto the serving plate, which honestly made my entire week. Now it's my go-to when I need to bring something that says I tried without requiring three days of prep work.

Ingredients

• Unsalted butter: Keep some softened for the cake and melt the rest for that gorgeous caramel layer that holds everything together
• Light brown sugar: Packed tight creates those deep amber pockets of buttery sweetness that make this cake unforgettable
• Pineapple rings: Drained well so they don't make the cake soggy, but save that juice for extra flavor
• Maraschino cherries: Tuck one into each pineapple center for that classic retro look that somehow never goes out of style
• Granulated sugar: Cream this thoroughly with butter for a cake that's light and not at all heavy
• Eggs: Room temperature eggs incorporate better and prevent the batter from curdling or separating
• Vanilla extract: Don't be shy with this, it's the subtle background note that makes everything taste homemade
• All-purpose flour: The foundation that holds up all that fruit without becoming dense or tough
• Baking powder: Make sure it's fresh so your cake rises properly instead of spreading sideways
• Salt: Just enough to balance all that sugar and let the vanilla shine through
• Whole milk: Adds moisture and richness, though I've used buttermilk in a pinch with great results

Instructions

Get everything ready:

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

Make the magic topping:

Melt 60 g butter and pour into the bottom of your prepared pan, then sprinkle brown sugar evenly across the surface.

Arrange the fruit:

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

Start the batter:

Cream 120 g softened butter and granulated sugar until the mixture turns pale and fluffy, which takes longer than you might think.

Add the wet ingredients:

Beat in eggs one at a time until fully incorporated, then add vanilla extract and watch the batter turn glossy.

Combine the dry ingredients:

Whisk together flour, baking powder, and salt in a separate bowl so everything distributes evenly.

Bring it together:

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

Layer it up:

Spoon the batter evenly over the pineapple rings and smooth the top, being careful not to disturb your fruit arrangement.

Bake until golden:

Bake for 38 to 42 minutes, or until a toothpick inserted into the center comes out clean and the top springs back when touched.

The big reveal:

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

Save

This cake has become my birthday tradition, mostly because the person getting to flip it over always feels like they're performing some kind of kitchen magic trick. My niece requested it three years in a row, which might be the highest compliment I've ever received.

Making It Your Own

I've swapped in pecans for cherries and loved the crunch, though nothing beats that classic diner look. Fresh pineapple works beautifully but needs a quick pat dry, and honestly, sometimes I skip the cherries altogether and just double down on extra pineapple rings.

Serving Suggestions

Warm with a scoop of vanilla ice cream is hard to beat, but I've also served it with barely sweetened whipped cream and felt fancy. The next morning, cold leftovers with coffee are an entirely different but equally wonderful experience.

Storage and Make-Ahead

This cake actually tastes better the next day when all those flavors have had time to really mingle and get comfortable. Keep it covered at room temperature for up to three days, though I've never seen it last that long in my house.

• The caramel layer stays tacky for hours, so flip it shortly before serving
• If you're transporting it, bring the serving plate and flip it at your destination
• Freeze leftovers wrapped tightly and they'll still be amazing weeks later

Save

Every time I make this cake, I remember that some recipes are classics for a reason. Simple ingredients, straightforward technique, and that moment of suspense before the flip make it worth making again and again.

Recipe FAQ

→ Should I serve this cake warm or at room temperature?

Both options work wonderfully. Warm serving enhances the caramel flavors and makes the texture incredibly tender, while room temperature allows the cake to set fully for cleaner slices. The 10-minute cooling period in the pan ensures easy inversion and optimal presentation.

→ Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple works beautifully and may offer slightly brighter flavor. Pat the rings dry before arranging to prevent excess moisture. Canned pineapple provides consistent sweetness and tenderness, while fresh adds a vibrant tropical note.

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

Insert a toothpick into the center—if it emerges clean or with just a few moist crumbs, the cake is ready. The edges should pull slightly from the pan, and the top will be golden brown. This typically takes 38–42 minutes at 175°C (350°F).

→ Can I prepare this ahead of time?

The cake can be baked a day in advance and stored at room temperature, covered. The flavors actually deepen overnight. For best results, invert before serving rather than storing upside-down. Warm individual slices if desired before serving.

→ What causes the cake to stick to the pan?

Proper butter and sugar distribution is key. Ensure the brown sugar is evenly sprinkled over melted butter before adding fruit. The 10-minute cooling period allows the caramel to set slightly, making inversion easier. Running a knife around the edges beforehand helps release cleanly.

→ Can I substitute ingredients for dietary needs?

For dairy-free options, plant-based butter and milk alternatives work well. Gluten-free flour blends may be used, though texture may vary slightly. The maraschino cherries can be replaced with fresh berries or pecans for a different flavor profile.