Pineapple Upside-Down Cake

My grandmother kept a well-watched aluminum cake pan on the top shelf, specifically reserved for upside-down cakes. The way she talked about it, you would think it possessed magical properties. When I finally inherited that pan and made my first pineapple version, I understood the reverence. The moment of inversion feels like pulling a secret out of a hat, that caramel-studded fruit suddenly becoming the star of the show.

Last summer I made this cake for a neighborhood potluck, and honestly, I was nervous about the flip. Everyone gathered around the counter like I was performing surgery. When that cake hit the plating board with a soft thud and the pineapple rings glistened up at us, there was actual applause. The best part? Someone asked for the recipe before they even took a bite.

Ingredients

• Unsalted butter (60g for topping, 120g for batter): Use real butter here, nothing with added salt or you will throw off the caramel balance
• Light brown sugar (150g, packed): The molasses in brown sugar creates that deep caramel flavor and beautiful amber color
• Canned pineapple rings (8–10): Canned pineapple works beautifully because it is already tender and packed in juice, though you can use fresh if you slice it thin
• Maraschino cherries (8–10): These pop against the golden pineapple and add that classic diner cake look
• Granulated sugar (200g): Provides sweetness and structure to the cake crumb
• Large eggs (2): Room temperature eggs incorporate better and help the cake rise properly
• Vanilla extract (1 tsp): Do not skip this, it bridges the gap between the fruity topping and vanilla cake
• All-purpose flour (190g): Standard flour gives the cake enough structure to hold up the weight of the fruit topping
• Baking powder (1 1/2 tsp): This is your lift, so check the expiration date if you have not baked in a while
• Salt (1/2 tsp): Just enough to balance the sweetness and enhance the vanilla flavor
• Whole milk (120ml): Whole milk creates a tender crumb, though you can use lower fat if that is what you have

Instructions

Prep your canvas:

Preheat your oven to 175°C (350°F) and generously grease a 23-cm (9-inch) round cake pan with butter. Do not skimp on the butter here, every nook needs coating.

Create the caramel layer:

Melt 60 g butter and pour it into the bottom of your prepared pan. Sprinkle the brown sugar evenly across the butter, tilting the pan if needed to distribute it. The sugar will look sandy, but it will melt into caramel as it bakes.

Arrange the fruit:

Lay pineapple rings over the brown sugar butter mixture, spacing them evenly. Nestle a maraschino cherry into the center of each pineapple ring where that natural hole lives. This is the satisfying part, like putting together a sticky puzzle.

Cream butter and sugar:

In a mixing bowl, beat 120 g softened butter and granulated sugar until the mixture turns pale and fluffy, about 3 to 4 minutes. The texture should look like whipped frosting.

Add eggs and vanilla:

Beat in the eggs one at a time, fully incorporating each before adding the next. Stir in the vanilla extract until the batter looks glossy and smooth.

Combine dry ingredients:

In a separate bowl, whisk together the flour, baking powder, and salt. This ensures even distribution of the leavening.

Build the batter:

Add the flour mixture to the butter mixture in three parts, alternating with the milk, starting and ending with the flour. Mix until just combined, then stop. Overmixing will make the cake tough.

Layer it up:

Spoon the batter carefully over the arranged pineapple, spreading it gently so you do not disturb your fruit design. 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 into the center comes out clean. The caramel will bubble up around the edges and that is exactly what you want to see.

The big flip:

Let the cake rest in the pan for exactly 10 minutes, no longer. Run a knife around the edges, place your serving plate over the pan, and with confidence, invert the whole thing. The cake should release with a satisfying sound.

Bookmark

My first attempt at this cake ended with me staring at a pan of beautiful caramelized fruit while the cake sat sadly on the counter. I learned that day that confidence matters more than technique. Now I take a breath, count to three, and flip like I mean it. The cake has never failed me since.

Making It Your Own

Once you have mastered the classic version, this cake welcomes all sorts of personality. I have swapped pecans for cherries, added coconut to the batter, and even tried fresh peach slices when pineapple was not in season.

Serving Suggestions

Warm slices of this cake need nothing more than a fork, but a dollop of lightly sweetened whipped cream or a scoop of vanilla ice cream never hurts. The contrast between the warm, sticky cake and cold, creamy topping is something special.

Storage and Make-Ahead Tips

This cake is best served the day it is made, when that caramel is still gooey and fresh. If you need to make it ahead, bake it fully, let it cool completely, then wrap it tightly. It will keep for two days at room temperature.

• Warm leftover slices slightly in the microwave to bring back that just-baked texture
• The fruit topping will soften overnight, so do not plan to serve this for special occasions more than a day after baking
• Never refrigerate this cake, the caramel hardens and the cake dries out

Bookmark

There is something deeply satisfying about a cake that reveals its true beauty only at the very last moment, like a dessert that knows how to make an entrance.

Recipe Questions

→ Should I use fresh or canned pineapple?

Canned pineapple rings work wonderfully and provide consistent results. Fresh pineapple can be used but may release more moisture during baking and require slightly longer cooking time to caramelize properly.

→ 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. The top should be golden brown and spring back lightly when touched.

→ Can I make this cake ahead of time?

Yes, bake the cake up to 24 hours in advance. Store at room temperature covered with plastic wrap or a cake dome. Serve at room temperature or warm individual slices in the microwave for 15-20 seconds.

→ What's the best way to invert the cake?

Let the cake cool in the pan for exactly 10 minutes after removing from the oven. Run a knife around the edges to loosen, place your serving plate upside down over the pan, then quickly flip both together. Lift off the pan carefully.

→ Can I substitute the maraschino cherries?

Absolutely. Pecan halves, fresh cranberries, or simply leaving the center of each pineapple ring empty all work beautifully. The cherries add traditional color and sweetness but aren't essential.

→ Why did my topping stick to the pan?

This usually happens if the cake cools too long before inverting. The 10-minute cooling window is crucial—the caramel needs to still be warm and pliable. If stubborn, warm the pan bottom on the stove for 30 seconds before trying again.