Name: Pineapple Upside Down Cake Recipe
Prep time: 20 min
Cook time: 45 min
Total time: 1 h 5 min
Cuisine: American
Ingredients: 565g/20 oz canned pineapple slices in juice (not in syrup); 12-18+ maraschino cherries; 60g/4 tbsp unsalted butter, melted; 1/2 cup brown sugar; 1 1/2 cups flour; 1 tsp baking powder; 1/4 tsp baking soda (or substitute 1 tsp baking powder); 1/4 tsp salt; 1/3 cup milk (full or low-fat); 1/4 cup pineapple juice (reserved from canned pineapple); 1/4 cup sour cream (full fat, or substitute plain yogurt); 1 tsp vanilla extract or essence; 115g/1 stick unsalted butter, softened to 18°C/64°F; 3/4 cup white sugar; 2 large eggs, at room temperature; Any leftover pineapple, chopped

If you’re craving a dessert that feels like a warm hug from your childhood, then this Pineapple Upside Down Cake Recipe is exactly what you need. I absolutely love this cake because it strikes the perfect balance between buttery caramelized pineapple topping and a moist, tender vanilla cake underneath. When I first tried making it, I discovered that using pineapple juice in the batter adds a subtle hint of fruity sweetness that just elevates the whole experience. Trust me, after one bite, you’ll be coming back for seconds!

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Why You’ll Love This Recipe

Classic Retro Charm: It brings back that nostalgic feeling of homemade goodness everyone adores.
Moist & Tender Cake: The sour cream and pineapple juice keep the cake beautifully soft and flavorful.
Easy to Make: You likely already have the ingredients, and the steps are simple to follow—even if you’re new to baking.
Impressive Presentation: The caramelized pineapple and cherries on top make this cake look stunning with minimal effort.

A close-up of a pineapple upside-down cake slice being lifted, showing three layers: the bottom layer is a golden-brown cake with a soft, crumbly texture; the middle layer has a glossy, caramel-like glaze covering the top of the cake; and the top layer features bright yellow pineapple rings with a shiny surface, each having a red cherry in the center. The whole cake is on a white plate placed on a white marbled surface, and there is a blurred background with more cherries visible. Photo taken with an iphone --ar 2:3 --v 7 - Pineapple Upside Down Cake, best pineapple upside down cake, easy pineapple upside down cake recipe, moist pineapple upside down cake, classic pineapple upside down cake

Ingredients You’ll Need

The magic of this Pineapple Upside Down Cake Recipe lies in how the ingredients work together to create that signature sweet, caramelized topping and a soft, flavorful cake base. I always recommend going for canned pineapple slices in juice rather than syrup to avoid an overly sweet finish.

Flat lay of fresh pineapple slices arranged neatly, a handful of glossy bright red maraschino cherries, a small white ceramic bowl of golden melted butter, a small white bowl filled with rich brown sugar, a neat mound of fine all-purpose flour, a small white bowl holding creamy full-fat sour cream, a small white bowl with smooth pale yellow butter softened, two large whole brown eggs with clean shells, a small white bowl containing clear pale yellow pineapple juice, a small white bowl of fine white sugar, a small white bowl with milk, a tiny heap of fine baking powder, a pinch of baking soda, and a pinch of salt, all ingredients symmetrically arranged on a clean white marble surface, soft natural light, photo taken with an iPhone, professional food photography style, fresh ingredients, white ceramic bowls, no bottles, no duplicates, no utensils, no packaging --ar 2:3 --v 7 --p m7354615311229779997 - Pineapple Upside Down Cake, best pineapple upside down cake, easy pineapple upside down cake recipe, moist pineapple upside down cake, classic pineapple upside down cake

Canned pineapple slices: Use ones packed in juice, not syrup—this keeps the sweetness balanced and you can use the juice to flavor the cake batter.
Maraschino cherries: These add a pop of color and subtle fruity sweetness right on top—feel free to add more if you like your cake extra festive.
Unsalted butter (melted & softened): Using two forms of butter gives you that lovely rich flavor and crisp, caramelized topping.
Brown sugar: Essential for making the caramelized pineapple topping sticky and luscious.
All-purpose flour: The backbone of the cake’s structure that keeps it tender.
Baking powder and baking soda: These give the cake the perfect rise and light crumb—don’t skip them!
Salt: Just a pinch to balance the sweetness.
Milk: Full or low-fat both work great—adds moisture to the cake batter.
Pineapple juice: Reserved from the canned pineapple, it infuses subtle fruitiness into the cake.
Sour cream: Makes the cake extra moist and tender—I sometimes substitute with plain yogurt if I’m out.
Vanilla extract: For that lovely warm, sweet aroma that sets the cake apart.
White sugar: For sweetness in the cake batter itself.
Large eggs: At room temperature, they help bind everything together and make the batter smooth.
Any leftover pineapple: Chopped and folded into the batter for bursts of juicy pineapple inside the cake.

Note: You’ll find the complete list of ingredients, along with their exact measurements, in the printable recipe card at the bottom of this post.

Variations

I like to think of this Pineapple Upside Down Cake Recipe as a delicious blank canvas—you can easily customize it to suit your taste or dietary needs. Don’t hesitate to experiment with some fun twists!

Tropical Twist: Adding shredded coconut to the batter adds a lovely texture and extra tropical flair my family goes crazy for.
Gluten-Free: I’ve swapped all-purpose flour for a gluten-free blend with fantastic results—just keep an eye on baking times.
Less Sweet: If you prefer a less sugary cake, reduce the white sugar in the batter by a quarter cup, and it’s still divine.
Vegan Option: Try substituting eggs with flax eggs and use coconut yogurt instead of sour cream; the cake texture shifts a bit but is still delicious.

How to Make Pineapple Upside Down Cake Recipe

Step 1: Prepare Your Topping Pan and Caramel

Start by preheating the oven to 180°C/350°F (160°C fan). Next, melt the 4 tablespoons of butter and stir in the brown sugar until it looks glossy and smooth. Pour this mixture evenly into your cake pan—the one I use is a 9-inch round pan. Then, artfully arrange the pineapple slices in the caramel, adding maraschino cherries in the middle of each ring and in the gaps. I love how this looks because once baked, it creates that stunning mosaic topping that wows every time.

Step 2: Mix the Dry Ingredients

In a separate bowl, sift together the flour, baking powder, baking soda (or extra baking powder if substituting), and salt. This mix ensures your cake rises perfectly and has a light crumb texture. Sifting also helps avoid lumps, which can sometimes trip up a beginner baker.

Step 3: Cream Butter and Sugar, Then Add Eggs

Using a mixer, cream the softened butter and white sugar until the mixture is pale and fluffy—this typically takes about 3 minutes. This step traps air to give your cake that lightness. Next, add eggs one at a time, beating well after each addition so the batter stays smooth. If your eggs are cold, give them 10 minutes on the counter; it really helps the batter come together seamlessly.

Step 4: Combine Wet and Dry Ingredients with Pineapple Juice and Sour Cream

Alternate adding the dry ingredients with the milk, pineapple juice, and sour cream into the creamed butter and sugar mixture. Start and end with the dry ingredients. Mix gently until just combined—overmixing can make the cake tough. Fold in any leftover chopped pineapple at this stage, so you get those little bursts of fruit inside.

Step 5: Bake and Cool Before Flipping

Pour your batter evenly over the prepared pineapple and caramel topping. Smooth the top and bake for about 45 minutes. Keep an eye on it—the cake is done when a toothpick inserted in the center comes out clean and the edges start to pull away from the pan. After baking, let the cake cool for about 10 minutes. This short wait is important; it helps the caramel set slightly so the topping stays intact when you flip it.

Step 6: The Big Flip!

Place a serving plate over the cake pan, then carefully invert the cake onto the plate in one smooth motion. Sometimes the caramel can stick to the pan if you flip too soon—if that happens, just loosen the edges carefully with a spatula next time. I always find that using a slightly warm pan helps release the topping easily.

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Pro Tips for Making Pineapple Upside Down Cake Recipe

Use Pineapple Juice Wisely: I learned using the reserved juice in the batter keeps the cake moist and infuses extra flavor.
Room Temperature Eggs: This small step made my cakes much smoother and prevented curdling when mixing.
Wait Before Flipping: Letting the cake sit and cool for 10 minutes ensures the caramel isn’t too runny and prevents messes.
Don’t Overmix Batter: I once got a dense cake from overmixing – gently fold ingredients together for the best texture.

How to Serve Pineapple Upside Down Cake Recipe

A close-up of a pineapple upside-down cake slice resting on a white plate with a white marbled background. The cake has two layers: the bottom layer is a moist yellow cake with a soft, crumbly texture, and the top layer is a caramelized golden brown pineapple ring with a bright red cherry in the middle. Part of the slice is lifted by a silver fork showing the moist inside texture, and the surface of the cake glistens with a shiny glaze. Photo taken with an iphone --ar 2:3 --v 7 - Pineapple Upside Down Cake, best pineapple upside down cake, easy pineapple upside down cake recipe, moist pineapple upside down cake, classic pineapple upside down cake

Garnishes

I usually keep it simple with just the pineapple rings and cherries from the topping, but sometimes I add a light dusting of powdered sugar or a dollop of freshly whipped cream for extra indulgence. A sprinkle of toasted coconut or even a few mint leaves can brighten up the presentation beautifully too.

Side Dishes

This cake shines on its own, but if you want to serve it alongside something, a scoop of vanilla bean ice cream or a generous spoonful of coconut cream works wonders. For a brunch setting, pairing it with fresh fruit salad adds freshness and balances the sweetness.

Creative Ways to Present

For special occasions, I’ve tried cutting the cake into mini squares, layering them with whipped cream and fresh pineapple bits in pretty glasses for a deconstructed pineapple upside down trifecta. Another fun idea is to bake cupcakes with the same topping for an easy, individual-sized treat your guests will love.

Make Ahead and Storage

Storing Leftovers

After baking, I store the cake in an airtight container at room temperature for up to 2 days. Keeping it covered prevents the caramel topping from drying out. If your kitchen is warm, popping it in the fridge is fine—it will firm up the caramel but bring it closer to room temperature before serving for the best softness.

Freezing

I’ve frozen slices wrapped tightly in plastic wrap and then foil for up to 3 months. When you’re ready to eat, thaw overnight in the fridge. The texture remains surprisingly moist, though the caramel is less glossy after freezing.

Reheating

To reheat, I warm individual slices in the microwave for about 15-20 seconds or place them in a 325°F oven for 10 minutes covered with foil to prevent drying. This brings back some of the original moisture and revives the caramel topping nicely.

FAQs

Can I use fresh pineapple instead of canned in this Pineapple Upside Down Cake Recipe?

Absolutely! Fresh pineapple can be used, but be sure to slice it evenly and cook it a little longer in the topping mixture to release its juices and develop that caramelized sweetness. Fresh pineapple is less sweet and more fibrous, so soaking it in a bit of sugar or syrup beforehand can mimic the canned fruit’s texture and flavor better.
Why does my Pineapple Upside Down Cake stick to the pan when flipped?

This usually happens when the cake hasn’t cooled long enough before flipping or if the pan wasn’t greased properly. I recommend waiting at least 10 minutes after baking before turning the cake out and ensuring you’ve lined or generously buttered the pan. Using a non-stick or cast-iron skillet also helps prevent sticking.
Can I substitute ingredients like sour cream in this recipe?

Yes! Sour cream gives the cake moisture and tenderness, but you can substitute it with plain yogurt, crème fraîche, or even buttermilk. Just make sure the substitute has a similar consistency so your cake batter doesn’t become too thin or thick.
How do I make the cake less sweet?

If you prefer a less sweet dessert, reduce the white sugar by up to 1/4 cup and consider using pineapple slices in juice rather than syrup to control added sweetness. You can also serve the cake with unsweetened whipped cream to balance out the sugary topping.
Can I make this Pineapple Upside Down Cake Recipe gluten-free?

Definitely! Swap the all-purpose flour for your favorite gluten-free flour blend. Just watch the baking time as it may vary slightly. Adding a teaspoon of xanthan gum can help maintain the cake’s structure and texture.

Final Thoughts

This Pineapple Upside Down Cake Recipe has become a beloved staple in my kitchen because it’s just so reliably delicious and crowd-pleasing. There’s something magical about that sweet, sticky topping that always brings smiles to the table. Whether you’re baking for a special occasion or simply craving a nostalgic treat, I promise you’ll love how easy it is to make and how impressive it looks. Give it a try—you might just make this your new go-to dessert!