Golden Pineapple Flip Cake

The Ultimate Homemade Pineapple Upside-Down Cake: A Timeless Dessert Recipe

There’s a special place in everyone’s heart for classic desserts, and the Pineapple Upside-Down Cake stands as a beloved icon. This particular homemade recipe elevates the nostalgic charm of this dessert, featuring a perfectly caramelized pineapple and cherry topping nestled atop an incredibly buttery, exquisitely moist, and delightfully fluffy cake. It’s a dessert that not only looks spectacular but tastes even better, promising a delightful experience with every forkful.

This year, one of my culinary goals has been to revisit and refine some cherished classic recipes, ensuring they are accessible, easy to follow, and consistently deliver outstanding results for your home baking needs. Today, I’m thrilled to share a recipe that embodies all these qualities: an effortlessly simple yet utterly delicious pineapple upside-down cake. Forget the box mixes; this from-scratch version is so superior, it might just convert even the most skeptical pineapple upside-down cake connoisseurs into lifelong fans.

What truly sets this recipe apart is its approachability despite being made entirely from scratch. You might think “from scratch” means complicated, but that couldn’t be further from the truth here. The vibrant, sweet topping can be prepared in mere minutes using your microwave, and we harness the convenience of canned pineapple slices and bright maraschino cherries to simplify the process without compromising on flavor or presentation. This recipe proves that homemade goodness doesn’t have to be a daunting task.

The cake batter itself is a testament to simplicity, requiring only everyday basic ingredients you likely already have in your pantry. However, don’t let its humble origins fool you; the resulting cake is extraordinarily buttery and moist, with a tender crumb that melts in your mouth. Its richness and depth of flavor are unparalleled, easily outperforming any box mix alternative. Prepare to be amazed by how such straightforward steps can yield such a magnificent dessert.

A finished pineapple upside down cake resting on a plate with a jar of cherries in the background.

Crafting Your Perfect Pineapple Upside-Down Cake

Creating this show-stopping pineapple upside-down cake involves two primary components: the delightful caramelized topping and the rich, moist cake batter. Each step is designed for ease and maximum flavor. Let’s walk through how to prepare both of these essential elements, ensuring your cake is a resounding success.

Mastering the Caramelized Topping

The journey to an irresistible pineapple upside-down cake begins with its signature topping. To prepare this, you’ll first melt a generous amount of unsalted butter. A quick and easy method is to use your microwave, which streamlines the process considerably. Once melted, stir in the brown sugar until it’s fully incorporated, creating a rich, sweet mixture. This delightful concoction is then spread evenly across the bottom of a 9-inch cake pan, forming the foundation of your caramelized layer.

For convenience and consistent results, this recipe utilizes canned pineapple slices and a small jar of vibrant maraschino cherries. This choice simplifies preparation without sacrificing flavor. A crucial tip here: remember to reserve the pineapple juice from the can! This precious liquid will be incorporated into the cake batter, infusing it with an extra layer of tropical flavor that truly elevates the overall taste profile. Draining the pineapple slices thoroughly and gently patting them dry before placing them in the pan will help prevent a watery topping, ensuring that perfect caramelization.

The arrangement of your pineapple slices and maraschino cherries in the pan is where you can add your personal touch. A standard 20-ounce can of sliced pineapple typically contains about 10 slices. I find that arranging seven full slices in a circular pattern on the bottom of the pan creates a beautiful visual base. The remaining three slices can be cut in half and artfully placed along the sides of the pan, forming an elegant border. Finally, scatter the bright red maraschino cherries in the open spaces, adding pops of color and bursts of sweet, tangy flavor. Once your topping is meticulously arranged, set the pan aside and prepare to mix your cake batter.

A round cake pan lined with pineapple slices, cherries, and the caramelized sugar topping.

Baking the Perfectly Moist Cake

The cake itself is designed to be incredibly moist, buttery, and infused with subtle pineapple notes. You’ll begin by combining your dry ingredients: all-purpose flour, baking powder, and a touch of salt. A critical technique for successful baking is the “spoon and level” method for measuring flour. Instead of scooping directly, spoon the flour into your measuring cup and then level it off with the back of a knife. This prevents over-packing, which can lead to a dense, heavy cake. Once these dry ingredients are thoroughly whisked together, set them aside.

Next, move on to the wet ingredients, starting with the creaming process. In a stand mixer or a large bowl with a handheld mixer, cream together softened unsalted butter, granulated sugar, and brown sugar. This step is vital and should take about 4 to 5 minutes, or until the mixture becomes notably light in color and fluffy in texture. This extended creaming time incorporates a significant amount of air into the mixture, which is essential for achieving that desirable light and airy texture in your finished cake. Don’t rush this step!

Once your butter and sugars are perfectly creamed, add the eggs one at a time, mixing well after each addition until fully incorporated. Follow this by mixing in the pure vanilla extract and the sour cream. At this stage, you might notice that your batter looks a little bit curdled, but rest assured, this is perfectly normal and nothing to worry about. The acidity of the sour cream is actually beneficial, reacting with the baking powder to create a softer, more tender crumb, while also adding incredible moisture.

Now, it’s time to bring in that reserved pineapple juice! Whisk together the remaining whole milk and the pineapple juice. While you could simply use ½ cup of milk, adding a portion of the pineapple juice directly into the batter truly enhances the cake’s tropical flavor, making it even more delicious and cohesive with the topping. With your mixer on low speed, alternate adding the dry ingredients with the milk and pineapple juice mixture. Begin and end with the dry ingredients, mixing just until combined. Be careful not to overmix, as this can develop the gluten too much, resulting in a tougher cake.

A glass mixing bowl holding cake batter that has been mixed up.

With your luscious batter ready, carefully pour it over the meticulously arranged pineapple and cherry topping in your prepared cake pan. Gently spread the batter into one even layer, ensuring it covers the fruit completely. The cake will bake in a preheated oven for approximately 45 to 55 minutes. You’ll know it’s perfectly done when a wooden toothpick inserted into the center comes out clean, with no wet batter clinging to it. To prevent the top from browning too much during the final 10-15 minutes of baking, you can loosely tent the cake with aluminum foil.

Once out of the oven, the anticipation builds! I highly recommend letting the cake cool slightly in the pan for about 10 minutes. This crucial resting period allows the caramelized topping to set properly and prevents the cake from sticking when you invert it. After this brief cooling, carefully flip the cake out onto a wire rack to finish cooling. The moment you unveil the glistening, fruit-studded masterpiece is truly rewarding!

A pineapple upside down cake on a plate with one slice taken out to show the texture of the cake.

Frequently Asked Questions (FAQs)

Here are answers to some common questions about making and storing your Pineapple Upside-Down Cake:

Can you freeze pineapple upside-down cake?

Absolutely, this cake freezes beautifully! To preserve its freshness and flavor, you have a couple of options. You can either wrap individual slices tightly with plastic wrap, then place them in a freezer bag or an airtight container. Alternatively, for a whole cake, wrap it securely in several layers of plastic wrap and then foil. Store it in the freezer for up to 3 months. For best results when serving, thaw the cake overnight in the refrigerator, and then allow it to come to room temperature before enjoying. This ensures the cake’s texture and moisture are perfectly restored.

How do you store it?

To keep your pineapple upside-down cake fresh and delicious, store it in an airtight container at room temperature for 2 to 3 days. While refrigeration isn’t strictly necessary for this period, if you need to store the cake for an additional 1 to 2 days beyond that, I highly recommend transferring it to the refrigerator. The cooler temperature will help extend its shelf life while maintaining its delightful taste and moist texture.

Can I use fresh pineapple?

Yes, you can certainly use fresh pineapple for this cake, and it adds a wonderful, vibrant flavor. If you choose to go this route, you’ll need to peel, core, and slice the pineapple into rings. You can juice the pineapple yourself to obtain the ¼ cup of pineapple juice required for the cake batter. If juicing is too much hassle, or if your fresh pineapple doesn’t yield enough juice, you can simply replace the ¼ cup of pineapple juice in the recipe with an equal amount of milk or even water, though pineapple juice enhances the flavor further.

When do you flip the cake?

The timing for flipping the cake is crucial for a perfect presentation. Once your cake comes out of the oven, allow it to cool in the pan for precisely 10 minutes. This brief cooling period allows the caramelized topping to firm up slightly and detach from the pan walls, making it easier to release. After 10 minutes, place a wire rack (or a serving plate) over the cake pan, and with a confident motion, carefully invert the cake onto the rack. Gently lift the pan away, revealing your beautiful, glistening pineapple topping. Allow it to cool completely on the wire rack before slicing and serving.

What if my cake pan is a different size?

This recipe is designed for a 9-inch round cake pan. If you use a different size, you might need to adjust baking time. For an 8-inch pan, the cake will be taller, potentially needing more baking time (add 5-10 minutes) and may require a slightly reduced batter amount. For a 10-inch pan, the cake will be thinner, baking faster (reduce time by 5-10 minutes). Always use the toothpick test to confirm doneness.

A single piece of cake on a plate with a bite taken out of it.

Essential Baking Tips for Success

  • **Room Temperature Ingredients are Key:** For optimal mixing and a smooth, cohesive batter, ensure all your cold ingredients, including butter, eggs, sour cream, and milk, are brought to room temperature before you begin. This allows them to emulsify properly and prevents a curdled texture.
  • **Accurate Flour Measurement:** Always measure your flour using the “spoon and level” method. Spoon the flour into your measuring cup until overflowing, then use the flat side of a knife or a straight edge to level it off. This prevents over-packing, which can lead to a dry, dense cake.
  • **Prevent Excessive Browning:** If you notice the top of your cake beginning to brown too quickly in the oven before it’s fully baked, loosely tent it with aluminum foil. This will protect the surface from direct heat, allowing the inside to cook through without burning the top.
  • **Don’t Overmix the Batter:** Once you start adding the dry ingredients to the wet, mix only until just combined. Overmixing develops the gluten in the flour, which can result in a tough, chewy cake rather than a tender, moist one.
  • **Oven Temperature Matters:** Invest in an oven thermometer to ensure your oven is truly at the temperature you set. Many ovens can be off by several degrees, which can significantly impact baking times and results.
  • **Explore Mini Versions:** Want to delight guests with individual portions? Try my mini pineapple upside-down cakes for a charming twist on this classic!

More Irresistible Cake Recipes to Try!

If you’ve fallen in love with the joy of baking this Pineapple Upside-Down Cake, you’re in for a treat! Here are more fantastic cake recipes from our collection that are sure to impress and satisfy any sweet craving:

  • Hummingbird Cake
  • Caramel Apple Upside-Down Cake
  • The Best Red Velvet Cake
  • Classic White Cake
  • Lemon Blueberry Bundt Cake

Watch the Recipe Video Tutorial

A whole pineapple upside down cake on a plate with a jar of cherries in the background.

Pineapple Upside-Down Cake

4.93 from 28 ratings
Prep Time: 30 minutes
Cook Time: 50 minutes
Total Time: 1 hour 20 minutes
This homemade Pineapple Upside-Down Cake features a caramelized pineapple topping and an incredibly buttery, moist cake.
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Ingredients

Servings: 8 slices

For the topping:

  • ¼ cup (60 grams) unsalted butter melted
  • ½ cup (100 grams) light brown sugar packed
  • 1 20-ounce can pineapple slices reserve juice for the cake
  • 20 maraschino cherries

For the cake:

  • 1 and ½ cups 190 grams all-purpose flour, spooned & leveled
  • 1 and 1/2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1/2 cup (115 grams) unsalted butter softened to room temperature
  • 1/2 cup (100 grams) granulated sugar
  • 1/4 cup (50 grams) brown sugar
  • 2 large eggs at room temperature
  • 1 teaspoon pure vanilla extract
  • 1/4 cup (60 grams) sour cream at room temperature
  • 1/4 cup (60 ml) whole milk at room temperature
  • 1/4 cup (60 ml) pineapple juice
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Instructions

 

  • Preheat your oven to 350°F (177°C). Lightly spray a 9-inch round cake pan with nonstick cooking spray, ensuring all sides and the bottom are coated. Set aside.

To make the topping:

  • In a small mixing bowl (or microwave-safe bowl), whisk together the melted butter and packed light brown sugar until fully combined and smooth. Pour this mixture into the prepared cake pan and spread it evenly across the bottom. Arrange the drained pineapple slices on top of the sugar mixture. If desired, cut any extra slices in half and place them along the sides of the pan. Finally, nestle the maraschino cherries artfully in and around the pineapple slices. Set the pan aside while you prepare the cake batter.

To make the cake:

  • In a large mixing bowl, whisk together the all-purpose flour (measured using the spoon & level method), baking powder, and salt until well combined. Set this dry mixture aside.
  • In the bowl of a stand mixer fitted with the paddle attachment (or using a large mixing bowl and a handheld electric mixer), cream together the softened unsalted butter, granulated sugar, and brown sugar. Beat on medium-high speed for 4 to 5 minutes, or until the mixture is visibly light in color and fluffy. Next, incorporate the eggs one at a time, mixing well after each addition until fully combined. Then, mix in the pure vanilla extract and room temperature sour cream until just blended. Remember to stop and scrape down the sides of the bowl as needed to ensure everything is thoroughly incorporated. (Don’t worry if the batter looks slightly curdled at this stage; it’s normal.)
  • In a separate small bowl, whisk together the reserved pineapple juice and the whole milk until fully combined.
  • With the mixer on low speed, gradually add the dry ingredients to the wet mixture in three additions, alternating with the milk and pineapple juice mixture. Begin and end with the dry ingredients. Mix only until the flour streaks disappear and the batter is just combined; be careful not to overmix.
  • Gently pour the prepared cake batter into the cake pan, evenly covering the pineapple slices and cherries. Spread it around with an offset spatula or the back of a spoon to create one smooth, even layer.
  • Bake for 45 to 55 minutes, or until a wooden toothpick inserted into the very center of the cake comes out clean. If you notice the top browning too much during the last 10 to 15 minutes of baking, loosely tent the cake with aluminum foil to prevent excess darkening.
  • Once baked, remove the cake from the oven and allow it to cool in the pan for exactly 10 minutes. This is a critical step! After 10 minutes, carefully invert the cake onto a wire rack (or your desired serving plate) and gently lift the cake pan away. Allow the cake to cool completely on the wire rack before slicing and serving.

Notes

Store your delicious pineapple upside-down cake in an airtight container at room temperature for 2 to 3 days. While refrigeration isn’t strictly necessary for short-term storage, I do recommend storing it in the refrigerator if you need to keep it fresh for an additional 1 to 2 days longer.

Freezing Instructions: To freeze, wrap individual slices or the entire cake tightly with plastic wrap, then place in a freezer bag or an airtight container. It can be frozen for up to 3 months. Thaw overnight in the refrigerator and allow to come to room temperature before serving for the best texture.

Milk Substitutions: I prefer using whole milk for a richer taste and texture in this cake. However, you can successfully replace it with 2%, 1%, skim, or even unsweetened almond milk without significantly altering the results.

Sour Cream Alternatives: Full-fat sour cream provides the best moisture and flavor, but low-fat sour cream works well too. If you don’t have sour cream, you may also replace it with an equal amount of plain Greek yogurt for a similar tangy richness and tender crumb.

Pineapple Juice Alternatives: If you find yourself without pineapple juice on hand, or prefer a less intense pineapple flavor in the cake batter, you can replace it with an equal amount of milk or even orange juice for a citrusy twist.

 

Cuisine: American
Course: Dessert
Author: Danielle
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