Pineapple Upside-Down Cake

There's something theatrical about flipping a cake upside down and having it emerge perfectly arranged with glistening pineapple and cherries. My grandmother used to make this for Sunday dinners when I was growing up, and I'd hover by the oven watching the butter bubble through the gaps in the fruit. She never measured anything precisely, yet her version always turned out beautifully caramelized. Now I understand why she loved making it, that moment when the cake releases onto the plate feels like pure magic.

I once brought this cake to a potluck and watched it disappear within minutes, with three different people asking for the recipe. One guest admitted they'd been intimidated by upside-down cakes for years, until they realized how forgiving this method actually is. The way the brown sugar transforms into a warm butterscotch glaze makes people think you spent hours on it.

Ingredients

• Unsalted butter: Use real butter here, nothing creates that caramel depth quite like it
• Light brown sugar: Packed tight because it needs to melt into that gooey topping
• Canned pineapple rings: Drain them well so they caramelize instead of steam
• Maraschino cherries: Tuck these into the pineapple centers for that classic look
• Softened butter: Room temperature butter incorporates properly for an even crumb
• Granulated sugar: Creaming this with butter creates the cake's structure
• Large eggs: These bind everything together and add richness
• Vanilla extract: Pure vanilla makes all the difference in the flavor
• All-purpose flour: This provides just enough structure without being heavy
• Baking powder: The lift that makes the cake tender rather than dense
• Salt: Just a pinch balances all that sweetness
• Whole milk: This brings everything together into a smooth batter

Instructions

Prep your pan:

Melt the butter directly in your cake pan in the oven while it preheats, then swirl to coat the sides

Create the caramel layer:

Sprinkle the brown sugar evenly over the melted butter, watching it begin to dissolve and bubble slightly

Arrange the fruit:

Place pineapple rings in a pleasing pattern, nestling a cherry into the center of each one

Cream the butter and sugar:

Beat the softened butter and granulated sugar until the mixture looks pale and fluffy, about three minutes

Add eggs and vanilla:

Beat in each egg individually, letting the first fully incorporate before adding the second, then pour in the vanilla

Mix the dry ingredients:

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

Combine everything:

Add the flour mixture in three parts, alternating with milk and mixing only until you no longer see dry streaks

Layer and bake:

Spoon the batter carefully over the fruit so you don't disturb the pattern, then bake until golden and set

The flip:

Let the cake rest for exactly ten minutes before running a knife around the edge and inverting onto your serving plate

Save

My aunt always made this for birthdays instead of traditional frosted cake, and it became the dessert everyone actually requested. There's something about the warm fruit against the tender vanilla cake that feels comforting rather than fussy. I've started making it for summer gatherings because it doesn't need refrigeration and travels beautifully.

Getting That Perfect Caramel

The brown sugar and butter create a natural caramel as the cake bakes, bubbling up around the pineapple edges. Don't worry if some of the sugar dissolves more than others, that variation is part of the charm. The hotter your oven, the deeper the color will become, but watch closely in the final minutes.

Fresh Versus Canned Pineapple

Canned pineapple works beautifully because it's already tender and packed in juice, but fresh pineapple adds a bright acidity you might enjoy. If using fresh, cut thick slices and core them carefully so they hold their shape during baking. Pat them dry before arranging to prevent excess moisture.

Serving Suggestions

This cake needs nothing more than a cup of coffee or cold glass of milk, but a dollop of unsweetened whipped cream helps balance the sweetness. The texture changes as it cools, warm from the oven it's almost pudding-like, while room temperature the cake becomes more structured.

• Try adding a splash of dark rum to the brown sugar layer for depth
• A pinch of cinnamon in the batter complements the pineapple beautifully
• This cake actually tastes better the next day, if it lasts that long

Save

There's a reason this cake has remained popular for generations, sometimes the old-fashioned recipes are the ones that bring the most joy to a table.

Recipe FAQs

→ Why is it called upside-down cake?

The name comes from the unique preparation method where fruit arranged at the bottom of the pan becomes the topping when the cake is inverted after baking. This technique creates that signature caramelized presentation.

→ Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple works wonderfully and often yields a more vibrant tropical flavor. Slice fresh pineapple into rings about 1/2-inch thick for best results. You may need to adjust baking time by a few minutes as fresh pineapple contains more moisture than canned.

→ 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, it's ready. The edges should pull away slightly from the pan, and the top will be golden brown. This typically takes 38–42 minutes at 175°C (350°F).

→ Can I make this ahead of time?

This cake tastes best served fresh the same day, but you can bake it up to 24 hours in advance. Cool completely, cover tightly, and store at room temperature. Warm briefly before serving to recreate that freshly baked texture. The caramel topping remains sticky and delicious.

→ What's the best way to invert the cake without breaking it?

Let the cake cool in the pan for exactly 10 minutes—this allows the caramel to set slightly while still being pliable. Run a knife around the edges to loosen, then place your serving plate upside-down over the pan. Using oven mitts, confidently flip both together in one smooth motion.

→ Can I substitute the maraschino cherries?

Certainly! Fresh or frozen pitted cherries work beautifully. For a nutty variation, try placing pecan halves in the pineapple centers instead. Some bakers even use drained cranberry halves or skip the cherries entirely—the pineapple alone makes a stunning presentation.