Pineapple upside-down cake is a timeless classic that combines the sweet tang of pineapple with a rich, buttery caramelized topping. My recipe puts a fresh spin on tradition by using sliced fresh pineapple, real butter, warm brown sugar, and fragrant vanilla bean. The base is a moist sour cream vanilla cake, which soaks up the sweet juices of the pineapples, making every bite unbelievably soft and flavorful. Whether you’re celebrating a birthday, a holiday, or just treating yourself on a weeknight, this recipe is sure to turn any occasion into a memorable event.
Though upside-down cakes have existed in various forms for centuries—often made with apples or cherries in cast-iron pans—the pineapple version became wildly popular in the early 20th century. Canned pineapple was a relatively new product at the time, and a recipe contest by the Hawaiian Pineapple Company (later known as Dole) helped put pineapple upside-down cake on the culinary map. This dessert’s eye-catching presentation—ringed pineapple slices adorned with cherries in a glossy caramel glaze—captured imaginations and taste buds alike. Today, many still cherish the nostalgic version with canned pineapple, but using fresh slices and a hint of vanilla bean brings out a remarkable depth of flavor.
While canned pineapple is convenient, fresh pineapple has a brighter, more vibrant taste. It offers just the right level of sweetness without overpowering the dessert. When combined with rich brown sugar and melted butter, fresh pineapple creates a caramelized topping that’s second to none. The addition of real vanilla bean adds an extra layer of luxurious aroma and flavor to your cake. To use vanilla bean, simply split the pod and scrape out the seeds—incorporating them into both the topping and the cake batter infuses an incredible warmth that complements the tangy fruit and creamy sour cream base.
One of the secrets to a truly soft and flavorful pineapple upside-down cake is the sour cream vanilla cake base. Sour cream adds moisture and a subtle tang to the cake, making it the perfect partner for the sweet topping. It’s also sturdy enough to hold up to the caramelized pineapple without becoming soggy. As the cake bakes, the butter and brown sugar bubble away, coating the pineapple slices in a glossy syrup that seeps into the cake’s crumb. Once inverted, you’re left with a stunning presentation of golden pineapple slices on top of a light, fluffy cake—a visual and culinary masterpiece.
If you’re feeling creative, you can adapt this recipe to make other upside-down cakes using fruits like apples, peaches, or plums. Apple upside-down cake is a fall favorite, pairing perfectly with cinnamon and a scoop of vanilla ice cream. Peach upside-down cake brings the taste of summer sunshine to your table, while plum upside-down cake has a sweet-tart flavor that’s perfect for those who prefer a more subtle sweetness. Each version is based on the same principle—arranging fruit in a caramel mixture, pouring batter over, then flipping the cake once it’s baked.
For those who love pineapple in all its forms, there are countless ways to enjoy this tropical gem. Pineapple tarts are a popular choice, especially for gatherings where bite-sized desserts are appreciated. Piña colada-inspired treats—like cupcakes or cheesecake bars—combine pineapple with coconut and a splash of rum extract. Grilled pineapple topped with cinnamon and a drizzle of honey is a simple yet delicious way to enjoy this fruit during barbecue season. Whether you’re a pineapple purist or you love it in a range of desserts, there’s no shortage of ways to celebrate the bright, tangy sweetness of pineapple.
With its soft, sour cream vanilla cake base and a luxurious topping of fresh pineapple, brown sugar, butter, and real vanilla bean, this pineapple upside-down cake offers the best of both nostalgic comfort and modern flair. It’s the type of dessert that’s as stunning to serve as it is comforting to eat, and it never fails to make a statement on the table. Whether you’re a devoted pineapple fan or simply curious about this vintage favorite, this cake promises to add a sweet slice of history—and a whole lot of delight—to your next occasion. Enjoy!
Pineapple Upside Down Cake
Ingredients
Pan Preparation
- 1 tbsp unsalted butter
- 2 tbsp brown cane sugar
Pineapple / Syrup
- ¼ cup unsalted butter
- ¾ cup brown cane sugar
- 1 vanilla bean see notes
- ½ large pineapple peeled, cored, and sliced about ¼-⅓" thick
Vanilla Sour Cream Cake
Dry Ingredients
- 1¼ cup all purpose flour
- ¾ cup granulated cane sugar
- ½ tsp salt
- ½ tsp baking powder
- ¼ tsp baking soda
Wet Ingredients Part 1
- ¼ cup sour cream
- 2 eggs large
- 1 tsp vanilla extract
Wet Ingredients Part 2
- ½ cup butter softened
- ¼ cup sour cream
Instructions
Preparation
- Preheat oven to 350℉
- Lightly butter a 9" round cake pan with 1 tbsp unsalted butter and sprinkle 2 tbsp brown cane sugar over the bottom.
Pineapple / Syrup
- Split 1 vanilla bean and scrape the seeds. Use both bean and seeds in the next step.
- In a large pan over medium-low heat, melt ¼ cup unsalted butter with ¾ cup brown cane sugar, the whole split vanilla bean, and the vanilla seeds.
- Add the prepared pineapple slices to the pan and cook for about 20 minutes, until the pineapple is tender. Turn the pieces over and stir the sugar mixture occasionally.
- Remove the pan from heat. Cover the bottom of the cake pan with the pineapple slices, overlapping if needed. Discard the whole vanilla bean. Pour the syrup over the pineapple slices.
Cake
- In a medium mixing bowl, whisk together 1¼ cup all purpose flour, ¾ cup granulated cane sugar, ½ tsp salt, ½ tsp baking powder, and ¼ tsp baking soda
- In a small bowl, whisk together ¼ cup sour cream, 2 eggs, and 1 tsp vanilla extract.
- To the flour mixture, add ½ cup butter and ¼ cup sour cream. Using a hand mixer, beat on low speed until smooth, then on medium speed until fluffy.
- Add the egg mixture to the flour mixture, and beat on medium speed until fluffy again, about 2 minutes.
- Spoon the cake batter onto the pineapples and syrup and spread evenly.
- Bake for 40 minutes or until the cake is a deep golden color. Remove from oven and let cool for 5 minutes on a wire rack.
- Loosen the cake from the pan with a knife along the edge. Place an upside down plate onto the top of the pan, firmly hold the plate to the pan and quickly invert it so the plate is underneath. Remove the pan and replace any pineapple that stuck.
- Serve warm for optimal flavour.
Notes
Nutrition
Authentic Recipes
We guarantee that all of our recipes are authentic recipes; they're developed, cooked or prepared, and enjoyed in our home. We are not professional, or even mediocre, photographers, and occasionally create AI images when photos don't turn out. None of the recipes on this website are created or modified using AI, and they never will be.
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