There’s something wonderfully nostalgic about a cake pineapple upside down. The buttery caramel glaze, golden pineapple rings, and ruby-red cherries feel like stepping back into your grandma’s kitchen—but with a flavor that still stands strong today. In this article, I’ll share my foolproof method for making the ultimate pineapple upside-down cake, packed with personal touches, expert tips, and a deep understanding of what makes this classic shine. Whether you’re a seasoned baker or just getting started, this cake delivers on comfort and wow-factor alike.
Pineapple Upside Down Cake
Equipment
- 9-inch round cake pan
- Mixing bowls
- Hand or stand mixer
- Measuring cups and spoons
- Rubber spatula
Ingredients
- ½ cup unsalted butter, divided
- ½ cup brown sugar
- 8 canned pineapple rings, drained
- 8-10 maraschino cherries
- 1 ½ cups cake flour
- 1 ½ tsp baking powder
- ¼ tsp salt
- 2 large eggs
- ½ cup buttermilk
- 1 tsp vanilla extract
Instructions
- Preheat oven to 350°F. Melt 1/4 cup of butter in a 9-inch cake pan.
- Sprinkle brown sugar evenly over the melted butter.
- Arrange pineapple rings and place cherries in the centers.
- In a separate bowl, cream remaining butter with sugar. Add eggs one at a time, then vanilla.
- In another bowl, mix flour, baking powder, and salt.
- Alternate adding dry ingredients and buttermilk to the creamed mixture.
- Pour batter gently over the pineapple layer.
- Bake for 40–45 minutes until golden and set.
- Cool for 10–12 minutes, then invert carefully onto a plate.
Notes
Don’t wait too long to flip the cake or the caramel may stick.
Store leftovers in the fridge, covered, for up to 3 days.
Nutrition
Table of Contents
Table of Contents
Why I Love Making Cake Pineapple Upside – My Southern Story
My First Cake Pineapple Upside: A Sweet Flip of Fate
I still remember the first time I made a cake pineapple upside down—it was a Sunday afternoon in early fall, and the leaves outside were starting to turn gold. I was thirteen, baking from one of Grandma’s index cards. She called it her “crowd-pleaser,” and she wasn’t wrong. That cake pineapple upside down was a hit even though I nearly dropped the pan during the flip.
There’s just something magical about turning a cake pineapple upside down after it bakes. Watching the brown sugar and butter glaze melt down over the golden pineapples and bright cherries feels like alchemy. The scent that fills your kitchen is pure nostalgia: warm caramel, fruity pineapple, and a hint of vanilla. For me, cake pineapple upside down isn’t just dessert—it’s memory, tradition, and joy all wrapped into one beautiful bite. If you love fruit-forward Southern bakes that bring back warm memories, my Strawberry Pound Cake offers the same comforting charm in every slice.
The History Behind the Cake Pineapple Upside Classic
While I like to think of my cake pineapple upside down as a family gem, this dessert has a rich American history. It became popular in the 1920s when canned pineapple was first mass-produced. Suddenly, it was easy for home cooks across the country to create this stunning, upside-down presentation with perfect fruit rings and cherries.
Since then, this cake pineapple upside down has earned its place as a beloved classic in homes from coast to coast—especially in the South. It’s easy to make, uses simple ingredients, and always delivers on flavor and flair.
How to Make Pineapple Upside Down Cake Perfectly
Ingredients That Matter for Cake Pineapple Upside
Pineapple upside-down cake might look dramatic, but it’s made from pantry staples. The secret? Every ingredient plays a role. You need unsalted butter—not margarine—for a rich, caramel base. Brown sugar, not white, creates that classic sticky glaze. And don’t skimp on the cherries. They’re not just decorative; they balance the pineapple’s tartness with a pop of brightness.
For the cake itself, I use cake flour for a tender crumb and buttermilk to add tang and moisture. Vanilla extract and a pinch of salt round it out. If you’re used to using boxed mix, try this once from scratch. You’ll be amazed how vibrant and buttery real pineapple upside cake can taste.
For a tropical variation, try adding a bit of shredded coconut—just like in my Mary Berry Coconut Cake Recipe—to bring a new layer of flavor.
Here’s a quick look at what you’ll need:
| Ingredient | Quantity |
|---|---|
| Unsalted Butter | 1/2 cup + 1/4 cup (separated) |
| Brown Sugar | 1/2 cup |
| Canned Pineapple Rings | 8 slices, drained |
| Maraschino Cherries | 8–10, whole |
| Cake Flour | 1 1/2 cups |
| Baking Powder + Salt | 1 1/2 tsp + 1/4 tsp |
| Buttermilk | 1/2 cup |
| Eggs | 2 large |
Step-by-Step: From Batter to Beautiful
- Preheat the oven to 350°F and melt 1/2 cup of butter in a 9-inch cake pan. Sprinkle brown sugar evenly over the melted butter.
- Arrange pineapple rings and cherries in a tight pattern across the sugar base.
- In a bowl, cream the remaining butter and sugar until fluffy. Add eggs, one at a time, then vanilla.
- Mix dry ingredients separately, then slowly alternate adding them with buttermilk to the wet mix.
- Spoon the batter gently over the fruit base, smooth the top, and bake 40–45 minutes until golden.
- Let rest 10 minutes, then invert while warm.
Presenting Cake Pineapple Upside Like a Pro
How to Flip Cake Pineapple Upside Without Cracks or Tears
There’s nothing worse than spending all that effort making a cake pineapple upside down, only to have it stick to the pan or fall apart during the flip. But don’t worry—I’ve got you covered.
Here’s my method: let the cake pineapple upside down cool in the pan for exactly 10–12 minutes after removing it from the oven. Not too hot, not too cold. Place a large, flat plate or cake stand over the top, then grip both pan and plate tightly and flip in one confident motion. A gentle shake helps loosen it—then that gorgeous caramel-topped fruit layer reveals itself.
If some pineapple or cherry pieces cling to the pan, don’t panic. Just lift them out and gently place them back. The sticky glaze will glue them in place, and no one will know.
Want to step up your presentation? Serve this cake pineapple upside on a vintage glass cake stand or a rustic wooden board. The contrast makes those pineapple rings and cherry centers pop.
What to Serve with Your Cake Pineapple Upside
This cake is sweet and fruity with a rich caramel base, so keep sides simple. A scoop of vanilla bean ice cream, a dollop of whipped cream, or even a drizzle of coconut cream works wonders.
If you’re intrigued by dramatic cake flips and bold presentation, you might also enjoy comparing layered desserts like Opera Cake vs Tiramisu.
If you’re feeling festive, a splash of dark rum in your whipped cream brings out the brown sugar notes beautifully. For gatherings, try baking the recipe in individual ramekins for single-serve upside-down cakes. They’re adorable, impressive, and portion-perfect.
This cake pineapple upside is just as fun and approachable as my Easy Chocolate Cake for Kids, making it a great family weekend bake.
Creative Twists on the Classic Cake Pineapple Upside
Unique Variations of Cake Pineapple Upside to Try
Once you’ve mastered the traditional cake pineapple upside, it’s time to have a little fun. This dessert is forgiving, flexible, and full of possibilities. You can swap ingredients, adjust flavors, or scale it for different occasions without losing the charm of the original.
Want a tropical take? Use fresh pineapple slices and swap buttermilk for coconut milk in the batter. A little shredded coconut sprinkled over the top before baking adds texture and depth. For a spiced twist, add cinnamon and cardamom to the brown sugar glaze, making it perfect for fall gatherings.
You can even turn this cake pineapple upside into a holiday centerpiece by using cranberries in place of cherries and adding orange zest to the batter. The sweet-tart combo is stunning on a winter dessert table.
Want to go gluten-free? Substitute cake flour with a high-quality gluten-free blend and make sure your baking powder is aluminum-free. The result? Still soft, still caramelized, and still unmistakably cake pineapple upside.
For events, consider turning this recipe into adorable single servings like Mini Cupcakes, perfect for quick plating and portion control.
Mini Cakes and Skillet Versions for Easy Sharing
If you’re baking for a crowd or want a quicker bake time, make individual portions. Pour the pineapple glaze and batter into jumbo muffin tins or ramekins. You’ll get perfect single servings of cake pineapple upside with minimal slicing or mess.
For a rustic feel, bake your cake pineapple upside in a cast-iron skillet. It browns beautifully, and the edges get that irresistible crispy-chewy texture. Just be sure to butter the pan generously to prevent sticking.
Another fruity favorite worth trying is the Chantilly Cake—it offers a lighter, whipped cream twist to your dessert table.
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Frequently Asked Questions About Cake Pineapple Upside
How to make pineapple upside down cake?
To make a cake pineapple upside down, start by melting butter and brown sugar in the bottom of a 9-inch pan. Arrange pineapple rings and maraschino cherries over the caramel. Mix a simple cake batter with cake flour, eggs, vanilla, and buttermilk. Pour it gently over the fruit and bake at 350°F for about 40–45 minutes. Let it cool for 10 minutes, then flip it onto a serving plate for that signature upside-down reveal.
How do you make a pineapple upside down cake that doesn’t stick?
Use a well-greased pan and don’t skip the butter in the glaze. Allow the cake pineapple upside to cool just enough—10 to 12 minutes—before flipping. If you wait too long, the sugar will harden. If you flip too early, it may fall apart. Loosen edges gently with a knife for a clean release.
How to bake a pineapple upside down cake in a skillet or ramekins?
For skillet versions, follow the same steps using a 10-inch cast-iron pan. For individual ramekins, divide the butter, brown sugar, and fruit among greased ramekins, then pour in the batter. Reduce bake time to 20–25 minutes. These mini cake pineapple upside servings are ideal for parties or portion control.
Where to buy pineapple upside down cake?
You can find pre-made cake pineapple upside in most grocery bakeries, especially around holidays. However, nothing compares to homemade. If you’re short on time, local bakeries often offer custom orders, or you can check farmer’s markets for small-batch versions.
Does pineapple upside down cake need to be refrigerated?
Yes, if you’re not eating it the same day. The fruit topping makes cake pineapple upside more prone to spoilage. Store leftovers in an airtight container in the fridge for up to 3 days. Warm slices slightly before serving for best taste and texture.
Can you freeze pineapple upside down cake?
Yes, but it’s best to freeze individual slices wrapped tightly in plastic wrap, then placed in a freezer-safe container. Thaw at room temperature or reheat gently. Just note that the fruit layer might release extra moisture, so texture can change slightly.
Conclusion
There’s something timeless and joyful about a cake pineapple upside. It’s a dessert that brings smiles with its golden caramel topping, vibrant fruit, and soft, buttery crumb. Whether you stick to the traditional version or try a modern twist like coconut milk or individual servings, this cake never fails to impress.
From my very first wobbly flip in a North Carolina kitchen to the polished versions I bake today, cake pineapple upside has become one of my signature bakes—just like it can be for you. Try it once, and it’ll earn a permanent place in your recipe box.
While cake pineapple upside keeps things humble, the Lambeth Cake shows off a vintage decorating style that’s full of flair and frosting.
If you’re exploring classic bakes with modern adaptations, don’t miss my Vegan Carrot Cake Recipe, which captures all the nostalgia with a plant-based twist.