Pineapple Upside-Down Cake

The smell of brown sugar caramelizing in the oven still takes me back to my grandmother's tiny kitchen, where I first learned that pineapple rings could transform into something magical. I was eight years old, standing on a wobbly chair, watching her arrange those bright yellow circles with surgical precision. She told me the secret was patience—waiting for that perfect moment when the butter and sugar became a golden amber pool. Now every time I make this cake, I hear her voice reminding me not to rush the good things.

Last summer I made this for a Fourth of July potluck, and I swear people hovered around the kitchen island until it came out of the oven. My friend Sarah actually gasped when I turned it over onto the serving plate—there's something so satisfying about that reveal moment. The cake disappeared faster than anything else on the table, and three people immediately asked for the recipe.

Ingredients

• Unsalted butter: Use real butter here, not margarine—the flavor difference is huge and it creates that rich caramel base
• Light brown sugar: The molasses in brown sugar gives the topping its deep caramel flavor and gorgeous color
• Canned pineapple rings: Canned pineapple works beautifully here because they're perfectly uniform and already tender
• Maraschino cherries: These little red jewels tucked into each pineapple ring make the classic look we all love
• Granulated sugar: Creamed with butter, this creates the tender, fluffy cake base that balances the sweet topping
• Large eggs: Room temperature eggs incorporate better and help give the cake its structure
• Vanilla extract: Pure vanilla extract makes the cake taste homemade and special
• All-purpose flour: Regular flour gives the cake just enough structure without being heavy or dense
• Baking powder: This is what makes the cake rise and become light and tender
• Salt: Just a pinch balances all the sweetness and makes the flavors pop
• Whole milk: Whole milk creates the tenderest crumb—low-fat milk can make the cake slightly dry

Instructions

Get your oven ready:

Preheat to 175°C (350°F) and generously grease a 23-cm (9-inch) round cake pan with butter

Make the caramel base:

Melt 60 g butter in the prepared pan, then sprinkle the brown sugar evenly over the top

Arrange the fruit:

Place pineapple rings over the sugar mixture and tuck a maraschino cherry into the center of each ring

Cream butter and sugar:

Beat 120 g softened butter and granulated sugar until fluffy and pale yellow, about 3 minutes

Add the eggs:

Beat in eggs one at a time, then stir in the vanilla until everything is smooth and combined

Mix the dry ingredients:

Whisk together flour, baking powder, and salt in a separate bowl so they're evenly distributed

Combine everything:

Add flour mixture and milk alternately in three additions, mixing just until the flour disappears

Bake it:

Spoon batter over the pineapple and bake for 38–42 minutes until golden and a toothpick comes out clean

The big reveal:

Cool for 10 minutes, run a knife around the edges, then invert onto a serving plate while still warm

Save

My daughter now helps me arrange the pineapple rings, and she's developed her own method of placing the cherries with exaggerated care. She calls them the 'buttons' that make the cake work. Last weekend she told me this cake tastes like sunshine and birthday parties combined, and honestly, I can't think of a better description.

Serving Suggestions That Work

Warm slices with a scoop of vanilla ice cream create that perfect hot-and-cold contrast that makes dessert memorable. A dollop of lightly sweetened whipped cream also works beautifully if you want something lighter than ice cream.

Making It Your Own

Fresh pineapple works if you prefer it, though you'll need to slice it into rings and pat it dry first. Pecan halves can replace the cherries for a nutty twist that adds wonderful crunch to each bite.

Storage Tips

This cake actually tastes better the next day as the flavors meld together, though it rarely lasts that long in my house. Keep it covered at room temperature for up to three days.

• Warm individual slices in the microwave for 15 seconds if serving leftover cake
• The caramel topping softens over time, so it's best served within the first two days
• Freeze cooled slices wrapped in plastic for up to three months

Save

There's something wonderfully nostalgic about a cake that's been making people smile for generations, and I love that I'm now passing that same simple joy forward in my own kitchen.

Recipe FAQs

→ Can I use fresh pineapple instead of canned?

Yes, fresh pineapple works beautifully. Slice it into rings about 1 cm thick and pat dry before arranging in the pan. Fresh pineapple may need slightly longer caramelizing time.

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

Insert a wooden toothpick into the center of the cake. If it comes out clean or with just a few moist crumbs, the cake is ready. The top should be golden brown and spring back when lightly touched.

→ Can I make this cake ahead of time?

Bake the cake up to one day in advance. Store at room temperature covered with foil or in an airtight container. Serve slightly warmed in the microwave for 15-20 seconds for the best texture.

→ What can I substitute for maraschino cherries?

Pecan halves work wonderfully in the center of each pineapple ring for a nutty variation. You can also use fresh cranberries, dried cherries, or simply skip them entirely.

→ Why did my cake stick to the pan?

Always run a knife around the edges before inverting. If stuck, place the pan on a warm towel for 1-2 minutes to help loosen the caramel. Proper greasing of the pan before adding the butter and sugar is essential.

→ Can I freeze pineapple upside-down cake?

Wrap the cooled cake tightly in plastic wrap, then foil. Freeze for up to 3 months. Thaw overnight at room temperature before serving. The texture remains excellent after freezing.