Pineapple Upside-Down Cake

The first time I made this cake, I was terrified to flip it. I held my breath, counted to three, and turned the whole thing over like I was defusing a bomb. When that beautiful pattern of pineapple and cherries revealed itself, I actually cheered in my empty kitchen. Now it is my go-to dessert whenever I need something that looks impressive but is actually straightforward to make.

I brought this to a potluck last summer and watched three different people ask for the recipe. Something about the glossy fruit on top makes people assume it took hours to master. My grandmother kept hers simple, just pineapple and cherries, but I have learned that sometimes the classics become classics for a reason.

Ingredients

• Unsalted butter: Use room temperature butter for the cake batter to ensure it creams properly with the sugar
• Light brown sugar: Packed brown sugar creates that rich caramel layer that holds everything together
• Pineapple rings: Drain them thoroughly and pat them dry to prevent excess moisture in the caramel
• Maraschino cherries: These add both color and a pop of sweetness that balances the tangy pineapple
• Granulated sugar: Cream this thoroughly with the butter until the mixture looks pale and fluffy
• Eggs: Add them one at a time and let each fully incorporate before adding the next
• Vanilla extract: Pure vanilla makes a noticeable difference in a cake this simple
• All purpose flour: Measure by spooning into the cup and leveling off for accurate results
• Baking powder and salt: These work together to give the cake a tender rise
• Whole milk: The milk should be at room temperature to prevent the butter from seizing

Instructions

Prepare your pan and preheat:

Set your oven to 175°C and generously grease a 23 cm round cake pan with butter, getting into all the corners

Make the caramel layer:

Melt 60 g butter directly in the bottom of your prepared pan, then sprinkle the brown sugar evenly across the surface

Arrange the fruit:

Place pineapple rings over the sugar in a pattern that pleases you, then tuck a maraschino cherry into the center of each ring

Cream the butter and sugar:

Beat 120 g softened butter and granulated sugar together until the mixture is pale, fluffy, and noticeably increased in volume

Add the eggs and vanilla:

Beat in the eggs one at a time, letting each disappear completely before adding the next, then stir in the vanilla

Mix the dry ingredients:

Whisk the flour, baking powder, and salt in a separate bowl so they are evenly distributed

Combine everything:

Add the flour mixture in three parts, alternating with milk, mixing only until each addition disappears

Layer the batter:

Spoon the batter gently over your arranged fruit, then smooth the top with an offset spatula or the back of a spoon

Bake to golden:

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 rest for exactly 10 minutes, then run a knife around the edge, place your serving plate on top, and flip with confidence

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My daughter insists this tastes better warm, so I usually serve it within an hour of baking. The steam still rising from the plate makes the whole house smell like a bakery. I have learned that simple desserts often create the most lasting memories.

Making It Your Own

Sometimes I swap pecans for the cherries when I want something nutty instead of fruity. The pecans toast in the caramel and add a nice crunch. Fresh pineapple works beautifully, though it tends to be more acidic than canned, so the sweetness varies slightly.

Serving Suggestions

This cake needs nothing more than a cup of coffee, but a dollop of lightly sweetened whipped cream never hurts. My grandmother always served hers with vanilla ice cream that would melt into the warm caramel. The contrast of temperatures and textures makes something special happen.

Storage and Make Ahead

The cake keeps well at room temperature for up to two days, covered loosely with foil. I actually think the flavors deepen overnight as the caramel seeps into the cake. You can make it a day ahead, but let it come to room temperature before serving.

• Wrap leftovers tightly if refrigerating, as the cake can dry out in the fridge
• Reveal the pattern right before serving for maximum impact on your guests
• The caramel layer softens over time, so it is best served within 24 to 36 hours

Save

There is something deeply satisfying about a dessert that looks this impressive coming out of the pan. I hope this cake becomes a favorite in your kitchen too.

Recipe Questions & Answers

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

Insert a toothpick into the center of the cake. If it comes out clean or with just a few moist crumbs, the cake is done. This typically takes 38-42 minutes at 175°C (350°F).

→ Can I use fresh pineapple instead of canned?

Yes, fresh pineapple works beautifully. Slice it into rings about 1 cm thick. You may need to cook it slightly longer to ensure it caramelizes properly since fresh pineapple contains more moisture than canned.

→ Why should I wait 10 minutes before inverting the cake?

The resting period allows the caramel layer to set slightly and the cake structure to firm up. Inverting too soon can cause the cake to break apart or the topping to slide off.

→ Can I make this cake ahead of time?

This cake is best served the same day while still fresh, but you can bake it up to 24 hours in advance. Store covered at room temperature and warm slightly before serving for the best texture.

→ What's the best way to store leftovers?

Store the cake in an airtight container at room temperature for up to 3 days. For longer storage, refrigerate for up to 5 days, though the texture may become slightly denser. Bring to room temperature before serving.

→ Can I substitute the maraschino cherries?

Absolutely. Pecans or walnuts make an excellent nutty alternative. You could also use fresh cranberries, dried cranberries, or simply omit them and add extra pineapple rings.