The Ultimate Homemade Pineapple Upside Down Cake Recipe: Easy, Moist, and Perfectly Caramelized
Indulge in the vibrant, sweet flavors of the tropics with this incredible Pineapple Upside Down Cake, crafted from scratch right in your own kitchen! This beloved classic dessert is a true showstopper, featuring beautifully caramelized pineapple slices, bright and juicy Maraschino cherries, all nestled atop a wonderfully moist and buttery cake base. Despite its impressive appearance, this recipe is surprisingly simple, calling for just a few common ingredients and straightforward, step-by-step instructions. Get ready to bake a dessert that’s guaranteed to delight both your taste buds and your guests!
The Pineapple Upside Down Cake is more than just a dessert; it’s a nostalgic journey to sunny days and simpler times. This iconic treat earns its name because it’s baked with the fruit at the bottom of the pan, submerged in a rich, buttery brown sugar caramel glaze. Once baked, the magic happens: the cake is flipped over, revealing a stunning, naturally decorated top of glistening pineapple rings and ruby-red Maraschino cherries. This unique baking method not only creates a visually captivating dessert but also infuses the cake with incredible moisture and a delightful caramelized sweetness that truly sets it apart.
The allure of this cake lies in its dual nature: it looks incredibly sophisticated and complex, yet the process of making it is wonderfully simple. The secret to its striking presentation and fantastic flavor is the foundational layer of caramel. A quick mixture of melted butter and brown sugar is spread evenly across the bottom of the cake pan. Then, the vibrant pineapple rings and Maraschino cherries are carefully arranged in a decorative pattern on top of this caramel base before the rich, moist cake batter is poured over everything. As it bakes, the caramel bubbles and permeates the fruit, creating a sticky, sweet, and irresistible topping that truly defines this tropical masterpiece.
When the cake comes out of the oven and is ready to be inverted, the warm, flowing caramel works its magic, ensuring the cake effortlessly slides out of the pan. This process keeps the beautiful fruit design perfectly intact, ready to be admired and enjoyed. It’s a moment of pure baking triumph that never gets old!
As a professional baker with a passion for creating desserts that are both impressive and easy to execute, I knew I had to share this timeless recipe. It’s a favorite for a reason! Its charm and simplicity have even inspired me to create delightful variations, such as pineapple upside down cupcakes, perfect for individual servings, and a grand pineapple upside down bundt cake, which reveals a spectacular pattern with every slice. This classic is truly versatile!
If you’re preparing this cake for a special gathering or a party, consider pairing it with other tropical-inspired treats. These coconut cookies offer a lovely complementary flavor, or for another pop of color and fruitiness, these cherry cupcakes would make a wonderful addition to your dessert spread, ensuring a memorable experience for all.
Why You’ll Adore This Pineapple Upside Down Cake
There are countless reasons why this homemade pineapple upside down cake recipe stands out and quickly becomes a family favorite. First and foremost, it’s an incredibly visually appealing dessert. The golden-brown caramelized pineapple rings and bright red cherries create a stunning mosaic on top, making it a perfect centerpiece for any occasion, from casual family dinners to festive celebrations. Beyond its beauty, the cake itself is exceptionally moist and tender, thanks to the addition of pineapple juice and vegetable oil in the batter. The buttery, rich texture contrasts beautifully with the tangy sweetness of the fruit, creating a harmonious flavor profile that is both comforting and exotic.
Moreover, the ease of preparation is a major draw. While the result looks sophisticated, the process is straightforward, making it an ideal recipe for bakers of all skill levels. You don’t need any fancy decorating skills; the pan does all the work for you! The use of readily available canned pineapple ensures you can enjoy this tropical treat any time of year without fuss. It’s a truly satisfying baking project that delivers immense satisfaction with every slice.
Essential Ingredients for Your Tropical Treat
Creating this delicious cake requires a handful of basic ingredients, each playing a crucial role in achieving that perfect balance of flavor and texture. Here’s a detailed look at what you’ll need:
- Canned Pineapple Slices – These are undeniably the star of our show. Canned pineapple slices offer consistent sweetness and a convenient ring shape, essential for the cake’s signature design. They contribute a wonderful tangy-sweet tropical flavor and a significant amount of moisture to the overall dessert. Choosing slices over chunks ensures a clean, elegant pattern on the finished cake.
- Unsalted Butter – A fundamental component, butter imparts a rich, creamy flavor to the cake batter. More importantly, it’s the base of our irresistible caramelized glaze. When melted and combined with brown sugar, it creates that luscious, sticky layer that coats the pineapple and ensures the cake releases beautifully from the pan.
- Brown Sugar – This ingredient is key to the deep, molasses-rich sweetness and characteristic caramelization of the topping. Brown sugar not only sweetens the pineapple but also helps create a wonderfully sticky, golden-brown crust once the cake is inverted, enhancing both flavor and texture.
- Maraschino Cherries – These vibrant, juicy cherries are not just for decoration; they add bursts of fruity sweetness and a striking pop of ruby-red color. Strategically placed in the center of the pineapple rings and around the edges, they elevate the visual appeal and add another layer of classic flavor that complements the pineapple perfectly.
- Granulated Sugar – Used in the cake batter, granulated sugar provides the primary sweetness for the cake itself, ensuring a balanced flavor that harmonizes with the sweet and tangy fruit topping.
- All-Purpose Flour – This is the structural backbone of our cake. All-purpose flour provides the necessary framework, giving the cake its tender yet stable crumb. Measuring it correctly is vital for the perfect texture.
- Baking Powder & Baking Soda – These leavening agents are a dynamic duo that work in tandem to give the cake its desirable light, airy, and fluffy texture. They react during baking to create air bubbles, causing the batter to rise beautifully and become wonderfully tender.
- Kosher Salt – Often overlooked, salt is a flavor enhancer, not just a seasoning. In baking, a touch of kosher salt balances the sweetness of the sugars and fruits, bringing out and intensifying the natural flavors of all the other ingredients, resulting in a more complex and satisfying taste.
- Reserved Pineapple Juice – Don’t discard that pineapple juice! It’s a secret weapon for boosting the cake’s tropical flavor profile and adding crucial moisture to the batter, contributing to a truly tender and juicy crumb.
- Vegetable Oil – This addition guarantees an incredibly moist and tender cake. Vegetable oil helps create a light and fluffy texture and, unlike butter, contributes to a moist cake even after it has cooled, ensuring it stays fresh longer.
- Large Egg – The egg serves as an essential binding agent, holding all the cake batter ingredients together. It also adds richness, helps with leavening, and contributes to the cake’s overall structure and color.
- Vanilla Extract (Optional) – While the tropical flavors are prominent, a dash of vanilla extract provides a warm, aromatic backdrop. It subtly enhances and rounds out the overall flavor profile, complementing both the pineapple and cherries beautifully.
Crafting Your Homemade Pineapple Upside Down Cake
Bringing this stunning cake to life is a straightforward and enjoyable process. Follow these detailed steps to ensure a perfect bake every time:
Step 1: Prepare for Baking. Begin by preheating your oven to a precise 350°F (175°C). This ensures the oven is at the correct temperature when your cake goes in, promoting even baking. Next, take a 9-inch round cake pan and generously spray it with a good quality non-stick baking spray, preferably one that contains flour. This crucial step helps prevent the cake and its delicate caramelized topping from sticking, making the inversion process smooth. Set the prepared pan aside as you gather and prepare your ingredients.
Step 2: Prepare the Pineapple. Open your can of pineapple slices. Carefully drain all the liquid, making sure to reserve ¾ cup of this precious pineapple juice—we’ll need it for the cake batter! Using paper towels, thoroughly pat dry both sides of each pineapple slice. Removing excess moisture is vital; it prevents a soggy cake and allows the caramel to adhere properly to the fruit, ensuring beautiful caramelization.
Step 3: Assemble the Brown Sugar Glaze. In a small, microwave-safe bowl or a saucepan on the stove, melt the ¼ cup of unsalted butter until completely liquid. Add the ½ cup of brown sugar to the melted butter and stir vigorously until the sugar is fully combined and dissolved. It’s important to break up any hard pieces of brown sugar to ensure a smooth glaze. Once combined, pour this rich brown sugar mixture evenly into the bottom of your prepared 9-inch cake pan, spreading it with a spoon or spatula to create a uniform layer.
Step 4: Arrange the Pineapples and Cherries. This is where the artistry comes in! Carefully place the dried pineapple slices onto the brown sugar mixture. Typically, one slice goes in the center, and the remaining slices are arranged in a circular pattern around it, fitting snugly to cover the bottom of the pan. Next, take your Maraschino cherries and place one in the center of each pineapple ring. You can also strategically place additional cherries in the gaps between the pineapple slices or around the outer edge to create a truly pretty and inviting design. Take your time with this step, as it determines the final appearance of your cake.
Step 5: Make the Cake Batter. In a large mixing bowl, combine all your dry ingredients: the ¾ cup granulated sugar, 1 ¼ cup all-purpose flour, 1 teaspoon baking powder, ¼ teaspoon baking soda, and ½ teaspoon kosher salt. Use a whisk to lightly combine these ingredients, ensuring they are evenly distributed. In a separate bowl, or directly into the dry ingredients (if your bowl is large enough), add the reserved ¾ cup pineapple juice, ¼ cup vegetable oil, 1 large egg, and the 2 teaspoons of vanilla extract (if using). Mix everything together using a whisk or an electric mixer on low speed until just combined. Be careful not to overmix the batter; overmixing can lead to a tough cake. A few small lumps are perfectly fine!
Step 6: Bake the Cake. Gently pour the prepared cake batter over the arranged pineapple slices and cherries in the pan, spreading it carefully to ensure the fruit design is completely covered. Transfer the cake pan to your preheated oven and bake for 35-40 minutes. You’ll know the cake is done when the top feels firm to the touch, and a wooden skewer or toothpick inserted into the center of the cake (avoiding the fruit layer) comes out clean.
Step 7: Cool and Invert. This step is critical for a successful flip! Once baked, remove the cake from the oven and allow it to cool in the pan for exactly 10 minutes. This brief cooling period allows the cake to set slightly and the caramel to remain warm and fluid enough to release easily. After 10 minutes, grab a wire cooling rack or your desired serving plate and carefully place it on top of the cake pan. With a firm, quick motion, confidently invert the cake pan onto the rack or plate. The cake should slide out beautifully. Lift the pan off to reveal your gorgeous, caramelized pineapple masterpiece! Allow the cake to cool completely on the wire rack before attempting to slice and serve it. Cooling fully helps the cake set and the flavors meld. Enjoy your magnificent creation!
Expert Tips for a Perfect Pineapple Upside Down Cake
Achieving a picture-perfect and delicious pineapple upside down cake is easy with these helpful tips:
- Dry the Pineapple Thoroughly: This is a non-negotiable step! Excess moisture from the canned pineapple can seep into the cake batter, making your cake soggy and preventing the caramel from setting correctly. After draining, use paper towels to gently but thoroughly blot both sides of each pineapple slice until they are as dry as possible. This ensures a beautiful, firm caramel layer and a perfectly moist, not wet, cake.
- Ensure a Smooth Caramel Base: When preparing the brown sugar and butter mixture for the bottom of the pan, take your time to stir until all the brown sugar crystals have completely dissolved and there are no clumps. A smooth, well-mixed caramel glaze will spread evenly and coat the pineapple slices beautifully, resulting in that gorgeous, glossy finish when the cake is flipped. Any undissolved sugar can create a gritty texture.
- Timing is Everything for Inversion: The 10-minute cooling period in the pan is crucial. If you attempt to flip the cake too soon, it might not be set enough and could fall apart. However, waiting too long (more than 10-15 minutes) can cause the caramel to cool, harden, and stick to the bottom of the pan, making it very difficult—or even impossible—to invert the cake cleanly without damaging the beautiful fruit topping. Set a timer and be ready to flip promptly!
- Use a Good Non-Stick Pan or Parchment Paper: While baking spray is recommended, for extra assurance, you can cut a circle of parchment paper to fit the bottom of your cake pan. Lay it on top of the baking spray before adding the caramel and fruit. This creates an additional barrier that guarantees a clean release every time, especially if you’re using an older pan.
- Don’t Overmix the Batter: Just like with most cakes, overmixing the batter can develop the gluten in the flour too much, leading to a tough and chewy cake instead of a light and tender one. Mix only until the ingredients are just combined and no streaks of dry flour remain. A few small lumps are perfectly acceptable and won’t affect the final texture.
- Check for Doneness Accurately: While a firm top is a good indicator, always use the toothpick test. Insert a wooden skewer or toothpick into the center of the cake (avoiding the fruit layer at the bottom). If it comes out clean or with a few moist crumbs attached, your cake is done. If it’s still wet, bake for a few more minutes, checking frequently.
Variations and Serving Suggestions
This classic pineapple upside down cake is perfect as is, but it also serves as a fantastic canvas for customization! For a nutty twist, sprinkle a layer of chopped pecans or walnuts over the caramel and before arranging the pineapple slices. The nuts toast beautifully and add a delightful crunch. You could also experiment with different spices; a pinch of cinnamon or nutmeg in the cake batter can complement the tropical flavors wonderfully. If you want to explore other fruits, thin slices of apple, pear, or even peaches can be used in place of, or in addition to, the pineapple, creating a unique “upside down” experience.
When it comes to serving, this cake shines brightest slightly warm or at room temperature. It’s truly divine on its own, allowing the rich caramel and moist cake to speak for themselves. However, a scoop of vanilla bean ice cream melting gently over a warm slice is an absolute indulgence. A dollop of freshly whipped cream provides a lovely, light counterpoint to the cake’s sweetness. For a touch of elegance, garnish with a fresh mint sprig or a dusting of powdered sugar. This cake is ideal for potlucks, family gatherings, or simply as a special weeknight dessert.
Storing Your Delicious Cake
Proper storage ensures your homemade pineapple upside down cake stays fresh and delicious for as long as possible:
Storing at Room Temperature or in the Refrigerator: Once the cake has completely cooled to room temperature, it’s essential to keep it well-covered to prevent it from drying out. You can either cover the entire cake tightly with plastic wrap or transfer individual slices to an airtight container. At room temperature, on your countertop, the cake will remain fresh and moist for up to 2 days. For extended freshness, especially in warmer climates, store the cake in the refrigerator for 3-5 days. Be sure to bring refrigerated slices back to room temperature or gently warm them for optimal flavor and texture before serving.
Freezing for Longer Enjoyment: Pineapple upside down cake freezes remarkably well, allowing you to prepare it in advance or save leftovers. Once the cake is completely cooled, wrap it very tightly first in a layer of plastic wrap, ensuring no air can get in. Follow this with a layer of heavy-duty aluminum foil. This double wrapping method is crucial to prevent freezer burn and preserve its delicious flavor and moisture. Alternatively, you can cut the cake into individual slices and wrap each slice separately using the same double-layer method. Frozen cake can be safely stored in the freezer for up to 2-3 months without a significant loss in quality. When you’re ready to enjoy your frozen cake, simply thaw it slowly in the refrigerator overnight. For individual slices, you can thaw them at room temperature for a few hours, or gently warm them in the microwave for a quick treat.

Homemade Pineapple Upside Down Cake
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Ingredients
- 20 oz can pineapple rings, (reserve juice!)
- 1/4 cup unsalted butter
- 1/2 cup brown sugar
- 1 jar Maraschino cherries
- ¾ cup granulated sugar, 150g
- 1 ¼ cup flour, 160g
- 1 tsp baking powder
- ¼ tsp baking soda
- ½ tsp kosher salt
- ¾ cup pineapple juice
- ¼ cup veg oil
- 1 egg
- 2 tsp Vanilla extract, (optional)
Instructions
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Preheat the oven to 350° F (175°C) and spray a 9” round cake pan generously with baking spray, preferably one that is made with flour. Drain the pineapple can, carefully reserving ¾ cup of the juice.
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Using paper towels, thoroughly pat dry both sides of the pineapple slices or pieces to remove any excess moisture.
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In a small bowl, melt the ¼ cup unsalted butter. Add the ½ cup brown sugar and stir until combined and smooth, breaking up any hard pieces. Pour the brown sugar mixture evenly into the bottom of the prepared cake pan.
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Carefully arrange the dried pineapple slices around the pan, placing one in the center and others in a circle around it. Place Maraschino cherries into the holes of the pineapple slices and in any gaps to create a beautiful design.
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In a large mixing bowl, combine the ¾ cup granulated sugar, 1 ¼ cup all-purpose flour, 1 tsp baking powder, ¼ tsp baking soda, and ½ tsp kosher salt. Whisk lightly to combine all the dry ingredients evenly.
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Next, add the ¾ cup of reserved pineapple juice, ¼ cup vegetable oil, 1 egg, and 2 tsp vanilla extract (if using) to the dry ingredients.
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Mix the batter until it is just combined and smooth. Be careful not to overmix, as this can make the cake tough.
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Pour the cake batter gently and evenly over the pineapple slices and cherries in the pan. Bake for 35-40 minutes, or until the top of the cake is firm and a wooden skewer inserted into the center comes out clean.
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Remove the cake from the oven and let it cool in the pan for exactly 10 minutes. Then, place either a wire cooling rack or your serving plate on top of the cake pan and, with a quick, confident flip, invert the cake.
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Carefully lift the pan away to reveal your beautiful cake. Allow it to cool completely on the rack or plate before slicing and serving for the best texture and flavor.