Buttery pineapple upside-down

The first time I pulled an upside-down cake from the oven and heard that satisfying sizzle as I inverted it onto the plate, I understood why this dessert has endured for generations. There's something almost magical about that moment when caramelized pineapple and jewel-like cherries are suddenly revealed, glistening on top like they were always meant to be there. My grandmother made this for every summer gathering, and I spent years thinking it was impossibly complicated until I finally tried it myself. It turns out the magic is mostly butter, brown sugar, and a little patience. Now it's become my go-to cake when I want something that looks fancy but feels genuinely effortless.

I baked this cake the afternoon my friend called to say she was bringing her new partner over for dinner, and I had about three hours to pull myself together. Instead of panicking about dessert, I remembered this recipe and felt instantly calmer. While the cake baked, the kitchen filled with this warm vanilla and caramel smell that somehow made the whole evening feel intentional and special, even though I'd thrown it together on the fly. When I inverted it and that golden crown of pineapple emerged perfect and glossy, my friend actually gasped, and her partner asked for the recipe before we'd even sat down to eat.

Ingredients

• Unsalted butter (for topping): 60 g melted into the pan bottom creates the rich caramel base that makes this cake shine, so don't skip it or substitute with oil.
• Light brown sugar, packed: 150 g of this is what turns into liquid gold under heat; pack it firmly so every spoonful counts.
• Canned pineapple rings: 8–10 rings work perfectly in a 9-inch pan, and draining them thoroughly prevents a soggy bottom.
• Maraschino cherries: One cherry centers each ring for that iconic look; they add sweetness and a pop of color.
• Unsalted butter (for cake): 120 g softened ensures your batter creams properly and creates tender crumb texture.
• Granulated sugar: 200 g beaten with butter gives you that light, fluffy base that makes the cake rise beautifully.
• Large eggs: Two eggs bring structure and richness; make sure they're at room temperature for even mixing.
• Vanilla extract: Just 1 tsp, but it whispers through every bite and balances the sweetness of the fruit.
• All-purpose flour: 190 g provides the structure; weigh it if you can for accuracy since measuring cups can vary.
• Baking powder: 1 1/2 tsp lifts the cake so it's tender rather than dense, making room for all that pineapple flavor.
• Salt: 1/2 tsp is your secret ingredient that deepens the vanilla and caramel notes you can't quite name.
• Whole milk: 120 ml keeps the crumb moist and tender; the slight acidity in milk works with the baking powder for even rise.

Instructions

Prepare Your Pan:

Heat your oven to 175°C (350°F) and get a 23-cm round cake pan ready. Melt 60 g butter directly in the pan so it coats the entire bottom evenly.

Build the Golden Layer:

Sprinkle 150 g of packed brown sugar over that melted butter, making sure it reaches into the corners. This mixture will caramelize into sticky sweetness as the cake bakes.

Arrange Your Crown:

Place pineapple rings in a single layer over the sugar, fitting as many as will comfortably sit; nestle a cherry in the center of each ring. This is your moment to be artistic if you want, or simply practical.

Cream the Base:

Beat 120 g softened butter with 200 g granulated sugar until it looks light, fluffy, and almost pale. This usually takes about 3 minutes with an electric mixer and is the foundation of a tender cake.

Add Eggs One at a Time:

Drop each egg in slowly while mixing, letting each one fully incorporate before adding the next. This prevents lumps and ensures even texture throughout.

Season and Mix Dry Ingredients:

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

Fold Everything Together:

Add the flour mixture to your butter mixture in three additions, alternating with the milk and starting and ending with flour. Stir just until combined; overmixing toughens the cake.

Layer and Smooth:

Gently spoon the batter over the pineapple rings and use a spatula to smooth the top so it bakes evenly.

Bake Until Golden:

Bake for 38–42 minutes until a toothpick inserted in the center comes out clean. The edges will pull slightly away from the pan.

The Critical Inversion:

Cool in the pan for exactly 10 minutes, then run a thin knife around the edges to loosen everything. Invert onto a serving plate quickly and confidently; hesitation is the only thing that creates a disaster.

Pin It

My sister once forgot to grease the pan and watched in horror as the whole cake stuck stubbornly when she tried to invert it, and that disaster taught me that sometimes the simplest steps matter most. Now whenever anyone asks me if this cake is really as foolproof as it seems, I tell them yes, but respect the small details. That's when this dessert stops being just a recipe and becomes a reminder that some of life's most impressive moments come from paying attention.

Flavor Variations Worth Trying

Once you've made this classic version, you'll start noticing ways to make it your own without losing what makes it special. Adding 1–2 tablespoons of pineapple juice directly to the batter deepens the tropical notes and adds a subtle tang that plays beautifully against the caramel. Some people swear by a pinch of cardamom or nutmeg whispered into the flour mixture, which adds warmth without announcing itself loudly. I've also experimented with brown sugar in the batter itself instead of just granulated sugar, which creates a more complex sweetness that echoes the topping.

Serving and Pairing Ideas

This cake stands beautifully on its own but truly sings when you add something cool and creamy alongside it. Whipped cream is the traditional choice, letting you control how much sweetness you're adding bite by bite. Vanilla ice cream melting into those warm caramel grooves creates something almost decadent, while Greek yogurt offers a tangy counterpoint if you're looking for something lighter.

Storage and Make-Ahead Tips

This cake actually improves after a day or two as the flavors marry and the caramel deepens in flavor, so don't hesitate to make it ahead. Wrap it well at room temperature and it keeps beautifully for three to four days, making it perfect for advance planning. You can even prepare the pan with butter and brown sugar in the morning, arrange your pineapple and cherries, cover loosely, and mix your batter when you're ready to bake.

• Freeze the cooled, uncut cake wrapped tightly for up to two months; thaw at room temperature before serving.
• If your cake develops condensation during storage, it means it's losing moisture, so an airtight container or cake keeper is worth the investment.
• Reheat slices gently in a warm oven if you want that fresh-from-the-pan warmth to return.

Pin It

There's something deeply satisfying about pulling this cake from the oven and watching people's faces when that caramelized crown is revealed, knowing you've created something that feels special and tastes even better. It's the kind of dessert that becomes a tradition, one inverted cake at a time.

Recipe FAQs

→ What type of cake pan is best for this dessert?

A 9-inch round cake pan is ideal for even baking and easy inversion of the cake.

→ Can fresh pineapple be used instead of canned?

Yes, fresh pineapple rings can be substituted. Be sure to drain excess juice to avoid sogginess.

→ How do you achieve the caramelized topping?

Melting butter and brown sugar together before layering pineapple rings creates a caramel base that caramelizes during baking.

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

After baking, let the cake cool in the pan for 10 minutes, then gently run a knife around the edges before inverting onto a plate.

→ Are there suggested accompaniments?

Serving the cake with whipped cream or vanilla ice cream enhances its rich, buttery flavors.