Pineapple Upside-Down Cake

My grandmother kept pineapple rings in the pantry year-round, and I could never understand why until she pulled this cake out of the oven on an otherwise ordinary Tuesday afternoon. The smell of caramelizing sugar and butter filled her tiny kitchen, and I watched in absolute awe as she flipped that cake over to reveal those glossy pineapple rings staring back like little suns. Now whenever I see those yellow cans at the grocery store, I remember how something so simple could make a regular afternoon feel like a celebration.

I made this for a potluck last summer and forgot to take pictures because everyone crowded around the moment I turned the cake out onto the platter. My friend Sarah actually gasped, and then proceeded to corner me near the dip bowl for the full recipe. Theres something about this cake that turns grown adults into giddy kids, maybe because it reminds them of their own grandmothers kitchens.

Ingredients

• 60 g (1/4 cup) unsalted butter: This forms the caramel base with the brown sugar, so use good quality butter for the best flavor
• 150 g (3/4 cup) light brown sugar, packed: Dark brown sugar works too but light gives a classic caramel taste without overwhelming the pineapple
• 8–10 canned pineapple rings, drained: Fresh pineapple is great but canned gives consistent moisture and that familiar retro taste we all love
• 8–10 maraschino cherries: These pop against the golden pineapple and add that classic bakery look
• 120 g (1/2 cup) unsalted butter, softened: Room temperature butter incorporates perfectly into the batter for an even crumb
• 200 g (1 cup) granulated sugar: Cream this thoroughly with the butter to create the cakes tender structure
• 2 large eggs: Bring these to room temperature too so they emulsify properly into the batter
• 1 tsp vanilla extract: Pure vanilla makes a noticeable difference in the final flavor
• 190 g (1 1/2 cups) all-purpose flour: Spoon and level your flour instead of scooping directly to avoid dense cake
• 1 1/2 tsp baking powder: This gives the cake its lift without making it too airy
• 1/2 tsp salt: Just enough to balance all that sugar and let the vanilla shine through
• 120 ml (1/2 cup) whole milk: Whole milk creates the richest texture, though low-fat works in a pinch

Instructions

Get your oven ready:

Preheat your oven to 175°C (350°F) and grease a 23-cm (9-inch) round cake pan with butter or cooking spray, making sure to get into all the corners.

Make the caramel layer:

Melt 60 g butter in the pan either in the oven or on the stovetop, then sprinkle the brown sugar evenly over the melted butter. It will look clumpy but that is exactly right.

Arrange the fruit:

Place pineapple rings over the sugar butter mixture however they fit best, then nestle a maraschino cherry in the center of each ring. Set aside while you make the batter.

Cream the butter and sugar:

Beat 120 g softened butter and granulated sugar together until the mixture turns pale and fluffy, about 3 to 4 minutes. This step is worth the extra effort for a tender cake.

Add the eggs and vanilla:

Beat in the eggs one at a time, making sure each is fully incorporated before adding the next, then stir in the vanilla extract until combined.

Mix the dry ingredients:

In a separate bowl, whisk together the flour, baking powder, and salt until evenly distributed so you do not get any pockets of baking powder in the finished cake.

Combine everything:

Add the flour mixture to the batter in three additions, alternating with the milk and beginning and ending with the flour mixture. Mix until just combined, being careful not to overmix.

Layer the batter:

Spoon the batter over the arranged pineapple and gently spread it to the edges without disturbing the fruit pattern underneath. Smooth the top as evenly as you can.

Bake until golden:

Bake for 38 to 42 minutes until the cake is golden brown and a toothpick inserted into the center comes out clean or with just a few moist crumbs.

The dramatic flip:

Let the cake cool in the pan for exactly 10 minutes, then run a knife around the edges. Place your serving plate over the pan and quickly but confidently flip everything over.

Save

My first attempt at this cake ended with half the pineapple still stuck to the pan because I got impatient and flipped it too soon. Now I set a timer and use those 10 minutes to make coffee, call people into the kitchen, and build up anticipation for the big reveal moment.

Serving Suggestions

This cake is incredible while still slightly warm, when the caramel is soft and the cake has that fresh-from-the-oven comfort. A scoop of vanilla ice cream melting into the warm caramel takes it over the top. I have also served it with a dollop of whipped cream and a sprinkle of toasted coconut for a tropical twist.

Storage and Make-Ahead

The cake keeps well at room temperature for up to 2 days, covered with a cake dome or foil. The caramel actually gets better as it sits and soaks into the cake slightly. You can bake it a day ahead and serve it at room temperature, though I promise nothing will be left over by day two anyway.

Easy Variations

Once you have the basic method down, this cake welcomes all kinds of twists. I have swapped pecan halves for cherries, added coconut to the batter, and even tried fresh pineapple when it is in season. Each version brings something slightly different to the table while keeping that nostalgic upside-down charm intact.

• Try adding 1 to 2 tablespoons of pineapple juice to the batter for extra pineapple flavor throughout
• Substitute pecan halves or walnut pieces for the cherries if you prefer nuts over the classic look
• Fresh pineapple works beautifully but may need a few extra minutes in the oven to fully caramelize

Save

There is something so joyful about a cake that looks impressive but comes from humble ingredients. I hope this recipe finds its way into your regular rotation and creates its own memories around your table.

Recipe Questions & Answers

→ Should I use fresh or canned pineapple?

Canned pineapple rings work beautifully and provide consistent results. Fresh pineapple can be used but may require longer cooking time to caramelize properly and contains more liquid that could affect the batter.

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

Insert a toothpick into the center of the cake. When it comes out clean or with just a few moist crumbs, the cake is ready. The edges should pull slightly away from the pan and the top will be golden brown.

→ Can I make this cake ahead of time?

The cake tastes best served warm or at room temperature the same day. You can bake it up to 24 hours ahead; store covered at room temperature and warm briefly before serving for the best texture.

→ What size pan works best?

A 23-cm (9-inch) round cake pan is ideal. Using a smaller pan may cause overflow, while a larger pan could result in a thinner cake. A cast iron skillet also works wonderfully for this dessert.

→ How do I prevent the cake from sticking?

Generously grease your pan with butter before adding the melted butter and sugar layer. Let the cake cool for exactly 10 minutes after baking before inverting—too long and the caramel hardens, too soon and it may fall apart.