Amazing pineapple upside down cake in 1 flip

If you’re anything like I was when I first started cooking—totally stressed out and just wanting food to be easy—you might think a dessert this gorgeous has to be loaded with complicated steps. But that’s just not true! I spent years running from complicated recipes after my corporate burnout, but coming back to baking simple classics like this **pineapple upside down cake** is where I found my joy again. This isn’t just another recipe, folks; this is the one that always delivers! I promise you a beautifully moist, tender crumb every single time, topped with that perfect, glistening, impossibly caramelized fruit layer. It’s truly a showstopper that tastes like pure vintage happiness.

Why This Pineapple Upside Down Cake is a Family Favorite Desserts Staple

I’ve tried so many retro desserts, but this one always steals the show. Honestly, it’s the one neighbors always ask about when I bring it to a gathering. I even have a whole section dedicated to my favorite sweet pastries, like the recipe for apple pie cheesecake, but this cake still wins for pure nostalgia factor! When you’re building your collection of guaranteed hits, this **pineapple upside down cake** has to be in there. I know you want results, not frustration, so trust me on why this recipe is different.

• It delivers that perfect, melt-in-your-mouth moist crumb we all crave.
• The fruit topping never burns or gets hard; it stays gooey and delicious.
• It brings back that wonderful nostalgic feeling from childhood parties.

It really is the ultimate showstopper dessert that’s surprisingly simple to create from scratch.

Achieving the Best Caramelized Pineapple Cake Topping

The secret sauce, or should I say, the melted butter and brown sugar base, is what separates this from any other version. When we melt butter and mix it right into the brown sugar at the bottom of the pan, we’re setting the stage for deep caramelization. This sugary, buttery blanket protects the pineapple slices while they bake, guaranteeing that gorgeous, shiny, slightly chewy layer when you finally flip it over. It’s chemistry you can eat!

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Ingredients for the Moist Pineapple Upside Down Cake

Okay, let’s talk ingredients, because this is where we turn simple pantry staples into magic. We’re making this **pineapple upside down cake** completely from scratch, so grab your 9-inch round pan or cast iron skillet! Pay close attention to the butter instructions—we use it melted for the topping and softened for the cake batter. Also, don’t toss that pineapple juice!

• 1/2 cup unsalted butter, melted (for the topping)
• 3/4 cup packed light brown sugar
• 1 (20 ounce) can pineapple slices in juice, drained (make sure you keep those liquid gold ounces!)
• 10 maraschino cherries
• 1 1/2 cups all-purpose flour
• 1 1/2 teaspoons baking powder
• 1/2 teaspoon salt
• 1/2 cup granulated sugar (for the cake)
• 1/2 cup unsalted butter, softened (for the cake)
• 2 large eggs
• 1 teaspoon vanilla extract
• 1/2 cup milk
• 3 tablespoons reserved pineapple juice

Ingredient Notes and Substitutions

Trust me on this one: for the topping, stick with light brown sugar. It just melts smoother and gives that classic, lighter caramel color without tasting too heavy. For the cake batter, your eggs absolutely need to be at room temperature—it helps them incorporate air better, giving us that required fluffy structure. If you forget, just set them in a bowl of warm (not hot!) water for about five minutes. Also, I love using buttermilk instead of plain milk sometimes; it adds just a slight tang that complements the pineapple beautifully.

How to Make Pineapple Upside Down Cake From Scratch: Step-by-Step

This is the fun part, where everything comes together! We’re building this beautiful cake from the bottom up—which, confusingly, means we start at the bottom of the pan. First things first: get that oven warmed up to 350 degrees F. I usually do this while I’m measuring out the flour so it’s ready when I am. You’ll want a 9-inch round cake pan, or if you’re feeling extra homey, go for that 10-inch cast iron skillet. Both work great for this **pineapple upside down cake**!

Step 1: The Caramelized Base

Pour that 1/2 cup of melted butter straight into your chosen pan. Then, sprinkle the 3/4 cup of brown sugar evenly over the top of that butter. Don’t rush this; you want full coverage! Next, arrange your pineapple slices beautifully on top of the sugar. I place one cherry right in the center of each ring, and then I tuck the rest of those bright red cherries around the edges. It sets up the presentation!

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Step 2: Mixing the Batter

While that topping is chilling out, whisk together your flour, baking powder, and salt in a medium bowl. Set that aside. In your big mixing bowl, cream the softened butter and granulated sugar until it’s fluffy—this is key for a tender crumb, just like when I learned to bake bread! Beat in your eggs one at a time, then mix in the vanilla. Now, you’ll gently alternate adding the dry mix and the milk/pineapple juice mixture, starting and ending with the dry ingredients. Mix only until it comes together. Seriously, stop mixing once the streaks disappear.

Step 3: The Flip!

Carefully pour that beautiful, thick batter right over your fruit layer. Bake this treasure for about 35 to 40 minutes. You know it’s done when a tester comes out clean. Now, the crucial part: let it cool in the pan for exactly 10 minutes. No more, no less! After that short wait, grab a serving plate, put it upside down over the pan, and working carefully with oven mitts—it’s hot!—flip the whole thing over. Lift that pan off slowly. If any little pineapples decided to stay behind, just nudge them back into place. Perfection!

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Tips for a No Stick Pineapple Upside Down Cake Tips Release

Sticking is the arch-nemesis of this cake, but we are prepared! The number one tip, which we do right in the instructions, is making sure that base of melted butter and brown sugar completely blankets the bottom of your pan. That buttery layer melts the sugar into a gorgeous, non-stick lacquer. If you’re using a standard aluminum cake pan, this works wonders. However, if you choose a cast iron skillet—which gives the best, most even heat, by the way—you still need that sugar/butter barrier. Also, remember to let it cool for those crucial 10 minutes! If you flip it too hot, things slide around. If you wait too long, the caramel can set too hard and pull the cake apart when you try to unmold it.

Making Your Pineapple Upside Down Cake Even Better

We’ve nailed the classic, but you know me—I love giving recipes that little extra nudge to make them truly *yours*. This simple fruit cake is already amazing, but a few tweaks can take it from great to unforgettable, especially when you’re entertaining or need a stunning centerpiece for a potluck. Building on this reliable base gives you total confidence whether you’re hosting a big crowd or just making a weeknight treat. If you enjoy making amazing things for people, you should definitely check out my tips for easy entertaining, too!

Variations on the Classic Pineapple Upside Down Cake Recipe

The recipe calls for standard milk, but swapping that out for coconut milk is a game-changer for a more tropical vibe! It adds a subtle richness without changing the structure too much. If you want to lean into that warm spice profile, try whisking just 1/4 teaspoon of ground cinnamon into your dry flour mix. It pairs so beautifully with the brown sugar caramel. Honestly, sometimes I even add a tiny pinch of freshly grated nutmeg, which really wakes up the sweet pineapple flavor.

Serving Suggestions for Your Caramelized Pineapple Cake

Now that you’ve successfully executed this stunning, upside-down masterpiece, it’s time to serve it! This Caramelized Pineapple Cake just screams retro comfort, right? It’s naturally beautiful sitting on that platter, but honestly, I think it needs a cool counterpart. Serving it warm is non-negotiable for me—that’s when the caramel is perfectly soft and gooey. I almost always pair a slice with a big scoop of good quality vanilla ice cream to cut through that sweetness. The contrast between the warm, tropical cake and the cold, creamy ice cream? Heavenly. If you’re not an ice cream fan, a dollop of freshly whipped cream is equally fabulous. Don’t forget to snap a picture before you dig in; this is one dessert worth showing off! If you love rich desserts like this, you might also adore my recipe for creamy bread pudding!

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If you end up snapping photos of your beautiful flip, come share them over on my Facebook page! I love seeing your successes at Pure Cooking Joy.

Storage and Reheating Instructions for Leftover Pineapple Upside Down Cake

So, you have leftovers? Lucky you! Since this pineapple upside down cake is so wonderfully moist, we need to treat it right. If you have any left over, cover the serving plate tightly with plastic wrap or transfer a slice to an airtight container. It usually keeps well at room temperature for about a day, but if it’s warm where you are, pop it into the fridge. Don’t worry about the topping getting a little sticky; that’s normal for fruit cakes!

When you’re ready for a second slice, skip the microwave if you can! That tends to make the cake dry. Instead, I gently warm small pieces in a toaster oven for just a few minutes until the caramel is soft again. If you absolutely must use the microwave, go in short 10-second bursts!

Frequently Asked Questions About This Easy Pineapple Upside Down Cake

I know you bakers out there always have questions when you get to the bottom of a post, especially with a retro pineapple dessert that looks this good! That’s totally fine. I gather up the most common things folks ask me about making this **Easy Pineapple Upside Down Cake** from scratch. If you’re worried about timing or pan size, trust me, I’ve got the answers. We want this cake to be a guaranteed win every time you pull it out of the oven. For more general baking advice, you can always browse my full blog archive!

Can I make this Pineapple Upside Down Cake in a Bundt Pan?

Oh, absolutely! Bundt pans are gorgeous for this, though they are deeper than our standard 9-inch round pan. Since the batter will be piled higher, you definitely need to adjust your baking time. While the 9-inch cake cooks in about 40 minutes, the Bundt version will likely need closer to 50 or 55 minutes. Always test it with that toothpick! Because of the intricate shape, make sure you grease and flour that pan extra well—we don’t want any part of that beautiful fruit topping sticking to those nooks and crannies.

What is the best pan size for this Classic Pineapple Upside Down Cake Recipe?

For this exact amount of batter, the best pan size is either a standard 9-inch round cake pan or a 10-inch cast iron skillet. The skillet is wonderful because it transfers heat so evenly, giving you that deeply golden edge. If you use something significantly smaller, like an 8-inch pan, the cake will be super thick, and you’ll need to add another 10 to 15 minutes of baking time. If you use a larger 9×13 pan, the layer will be too thin and will bake in under 30 minutes, so watch it carefully!

Estimated Nutritional Data for One Serving

I always like to give a snapshot of what we’re working with. Remember, these final numbers for our pineapple upside down cake can shift a tiny bit depending on the brands you use, especially with the canned fruit! The data below is just an estimate based on the ingredients listed. Don’t stress too much about macros when you’re sinking your teeth into such a comforting classic dessert, but here’s the breakdown!

• Serving Size: 1 slice
• Calories: 380
• Sugar: 30g
• Fat: 19g
• Protein: 4g
• Carbohydrates: 50g

Basically, it’s a rich, buttery treat meant for enjoying with friends!

Share Your Pineapple Upside Down Cake Creations

Listen, I poured my heart into making this the most reliable, incredibly moist **pineapple upside down cake** recipe out there for you. Now it’s time for the best part: checking out your results! I genuinely thrive on feedback. When you leave a comment below telling me how it went—maybe you tried the coconut milk variation, or maybe you perfected the flip—it helps every other home cook who comes here seeking confidence for their own kitchen adventures.

Please, try to leave a star rating if you loved this retro dessert, and if you snapped a photo of that gorgeous caramelized flip, tag me on social media! Knowing that this dessert brought a moment of pure cooking joy to your table makes all the difference in the world to me. I love connecting with you all! For more about my mission to bring joy back to the kitchen, check out my About Page if you haven’t already.

Classic Moist Pineapple Upside Down Cake Recipe

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This is the best pineapple upside down cake recipe, delivering a moist, tender crumb and a perfectly caramelized pineapple and cherry topping. It is a nostalgic, showstopper dessert that is easy to make from scratch.

• Author: purejoyalex
• Prep Time: 15 min
• Cook Time: 40 min
• Total Time: 55 min
• Yield: 8 servings 1x
• Category: Dessert
• Method: Baking
• Cuisine: American
• Diet: Vegetarian

Ingredients

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• 1/2 cup unsalted butter, melted
• 3/4 cup packed light brown sugar
• 1 (20 ounce) can pineapple slices in juice, drained (reserve 3 tablespoons juice)
• 10 maraschino cherries
• 1 1/2 cups all-purpose flour
• 1 1/2 teaspoons baking powder
• 1/2 teaspoon salt
• 1/2 cup granulated sugar
• 1/2 cup unsalted butter, softened
• 2 large eggs
• 1 teaspoon vanilla extract
• 1/2 cup milk
• 3 tablespoons reserved pineapple juice

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Instructions

1. Preheat your oven to 350 degrees F. You will need a 9-inch round cake pan or a 10-inch cast iron skillet.
2. Prepare the topping: Pour the 1/2 cup melted butter into the bottom of your pan. Sprinkle the 3/4 cup brown sugar evenly over the butter.
3. Arrange the pineapple slices on top of the brown sugar mixture. Place one maraschino cherry in the center of each pineapple ring, and place remaining cherries around the edges.
4. Prepare the cake batter: In a medium bowl, whisk together the flour, baking powder, and salt. Set this aside.
5. In a large bowl, cream together the 1/2 cup softened butter and 1/2 cup granulated sugar until light and fluffy. Beat in the eggs one at a time, then mix in the vanilla extract.
6. In a small bowl, whisk together the milk and the 3 tablespoons of reserved pineapple juice.
7. Gradually add the dry ingredients to the wet ingredients, alternating with the milk mixture, beginning and ending with the dry ingredients. Mix until just combined; do not overmix.
8. Carefully pour the cake batter over the pineapple and cherry layer in the pan. Spread the batter evenly.
9. Bake for 35 to 40 minutes, or until a toothpick inserted into the center comes out clean.
10. Let the cake cool in the pan on a wire rack for 10 minutes.
11. Place a serving plate upside down over the cake pan. Wearing oven mitts, carefully flip the pan and plate over together. Lift the pan off the cake. If any fruit sticks, gently place it back onto the cake.
12. Serve warm, perhaps with vanilla ice cream.

Notes

• To prevent sticking, make sure the butter and brown sugar completely cover the bottom of the pan before adding the fruit.
• If you are using a cast iron skillet, ensure it is completely cool before flipping to prevent burns.
• For an extra tropical flavor, substitute 1/4 cup of the milk with coconut milk.

Nutrition

• Serving Size: 1 slice
• Calories: 380
• Sugar: 30g
• Sodium: 250mg
• Fat: 19g
• Saturated Fat: 11g
• Unsaturated Fat: 8g
• Trans Fat: 0.5g
• Carbohydrates: 50g
• Fiber: 1g
• Protein: 4g
• Cholesterol: 85mg