Pineapple Upside Down Cake

By Patricia Walker

Published: December 30, 2025

Updated: December 30, 2025

Let’s bring back a classic with a cheerful twist! The Pineapple Upside Down Cake is the kind of dessert that instantly sparks nostalgia while still feeling fresh and vibrant. Imagine golden pineapple slices with lightly caramelised edges, bright red cherries tucked in like little jewels, all resting atop a tender, moist vanilla cake that’s infused with pineapple juice. It’s playful, it’s retro, it’s downright irresistible.

Retro desserts have a charm of their own. They remind you of summers past, backyard barbecues, and the simple joy of a cake that makes you smile before you even take a bite. Pineapple Upside Down Cake fits that bill perfectly—it’s both comforting and celebratory, like a little sunshine on a plate.

What Makes This Cake Special

“Upside Down” isn’t just a quirky name—it describes exactly how this cake works. Like a French tarte Tatin, the fruit goes in first, caramelised in butter and brown sugar, then the batter goes on top. After baking, you flip it over to reveal a glossy, sticky, golden fruit layer. The result? A visually stunning cake with a rich caramel-pineapple topping that tastes as good as it looks.

The cake itself is a soft, fluffy vanilla sponge that’s just moist enough thanks to pineapple juice and sour cream. It’s not dense like a pudding-style cake, nor dry like a plain sponge—it hits the sweet spot in the middle. Juicy pineapple pieces scattered throughout add bursts of flavor, complementing the caramelised top beautifully.

Ingredients

For the Pineapple and Cherry Topping

Canned pineapple slices in juice: Use pineapple in juice, not syrup. The syrup is too sweet and will overpower the cake. Reserve some juice for the batter, the rest for cocktails or smoothies.
Maraschino cherries: Bright red and sweet, perfect for pops of color. If unavailable, glacé cherries are a great substitute.
Butter: For melting and creating that luscious caramel layer.
Brown sugar: The secret to sticky, golden caramel.

For the Cake Batter

All-purpose flour: The backbone of the cake.
Sour cream: Keeps the cake tender and moist while giving structure.
Sugar: White sugar for a light-colored crumb.
Butter (softened to room temperature 18°C/64°F): Essential for creaming with sugar to create a fluffy base.
Large eggs (room temperature): Incorporate fully to ensure a smooth batter.
Baking soda & baking powder: Together, they give the cake lift and prevent it from collapsing under the weight of the fruit.
Milk: Any fat % works, adds moisture.
Vanilla extract: Enhances flavor more than artificial essence.

How to Make Pineapple Upside Down Cake

Step 1: Prepare the Topping

Pat fruit dry: Dry pineapple slices and cherries to reduce excess moisture.
Butter and sugar base: Pour melted butter into the pan and brush over the bottom and sides. Sprinkle brown sugar evenly. Don’t worry if it’s uneven—the caramel will spread while baking.
Arrange pineapple slices and cherries: Place pineapple slices on the base, optionally with halves surrounding whole rings. Place cherries in the center of rings and fill any gaps. Press gently to ensure they stick to the caramel mixture.
Chop leftover pineapple: Toss these into the batter for extra fruity pockets in the cake.

Step 2: Prepare the Cake Batter

Mix dry ingredients: Whisk flour, baking soda, baking powder, and a pinch of salt.
Mix wet ingredients: In a separate bowl, whisk milk, sour cream, and reserved pineapple juice.
Cream butter and sugar: Beat softened butter with sugar for 2 minutes until light and fluffy.
Combine flour and milk mixtures alternately: Fold in flour in 3 parts, alternating with milk mixture in 2 parts. This ensures a soft cake without overmixing.
Add pineapple pieces: Fold in chopped pineapple at the very end.

Step 3: Baking

Pour batter over the arranged pineapple and cherries. Smooth the surface.
Bake uncovered at 180°C/350°F (160°C fan) for 30 minutes.
Cover loosely with foil and bake another 15 minutes.
Check doneness by inserting a toothpick into the center—it should come out with crumbs, no raw batter.

Step 4: Turning Out the Cake

Flip confidently: Place a plate over the cake pan, then invert. Lift the pan slowly.
PRO TIP: If the cake sticks slightly, gently tap or shake the pan. With the generous butter in the caramel, sticking is rare.
Admire the glossy pineapple and cherry topping!

Serving and Storage

The cake stands about 4cm (1.6″) tall in a 23cm (9″) pan. The height ensures a perfect cake-to-caramel ratio.
Store in the fridge for up to 5 days. As it sits, the caramel pineapple juices soak into the cake, making it even more flavorful.
Serve at room temperature for the best texture and flavor.

Bright, retro, and utterly delicious, this Pineapple Upside Down Cake is a showstopper for any occasion. It’s sweet, tangy, visually stunning, and packed with nostalgic charm—a true dessert to smile about.– Patricia Walke