Pineapple Upside Down Cake Classic Recipe

Is there anything more frustrating than making a meal that only half the family will touch? I’ve been there, staring at a plate of lovingly prepared food while my kids push it around. We all need a win sometimes, a recipe that feels like a hug and gets everyone to the table without a fuss. If you’re looking for another surefire hit, you must try our Pineapple Upside-Down Banana Cake Bread.

That’s where our Pineapple Upside Down Cake Classic comes in. It’s the retro dessert that solves two problems: it’s a spectacular treat, and it’s secretly a picky-eater magnet. The magic is in the flip—turning a pan of caramelized fruit into a stunning cake never gets old. Let’s make something joyful together.

Recipe Overview

• Cuisine: American
• Category: Dessert
• Prep Time: 20 minutes
• Cook Time: 40 minutes
• Total Time: 1 hour
• Servings: 8

Why Even My Picky Eaters Love This!

I get it. New textures and mixed-up foods can be a hard no for little ones. This cake is different. First, it’s visually a sure thing. Those golden pineapple rings and bright red maraschino cherries are like edible art. Kids know exactly what they’re getting.

Second, the taste is pure, simple comfort. The brown sugar topping bakes into a sticky, sweet glaze that soaks into the soft cake. Every bite is consistent and familiar. It’s a dessert that feels special but isn’t the least bit intimidating. It’s a total crowd-pleaser.

Our Family-Friendly Ingredient List

I promise, no fancy stuff here. You probably have most of this in your pantry right now. The short list is part of what makes this recipe a keeper for busy families. For another easy, tropical treat that uses similar pantry staples, check out these Tropical Carrot Banana Pineapple Muffins.

• 1/2 cup (1 stick) unsalted butter
• 1 cup packed light brown sugar
• 1 can (20 oz) pineapple rings in juice (you’ll use the juice!)
• 1 jar of maraschino cherries
• 1 1/2 cups all-purpose flour
• 1 cup granulated sugar
• 1/2 cup milk (whole or 2% works great)
• 1/3 cup reserved pineapple juice
• 1/3 cup vegetable oil
• 2 large eggs
• 2 tsp baking powder
• 1 tsp vanilla extract
• 1/4 tsp salt

How to Get the Kids Involved in Cooking This

Getting kids in the kitchen builds confidence and makes them more likely to try the final product. For this cake, I have two favorite jobs for my helpers.

The first is arranging the fruit. Let them place the pineapple rings in the pan and put a cherry in the center of each one. It’s like a tasty puzzle. The second is the big moment: the flip! When the cake is baked and cooled just enough, let them hold the plate while you (with oven mitts!) confidently invert the pan. Their gasp of delight is the best part.

The Full Step-by-Step Instructions

Don’t let the “upside down” part worry you. It’s much easier than it looks. Just follow these simple steps for a perfect result every time.

1. Preheat your oven to 350°F (175°C). Get out a 9-inch round cake pan or a 10-inch cast iron skillet.
2. Melt the 1/2 cup of butter in the microwave or a small saucepan. Pour it directly into your cake pan and swirl it to coat the bottom.
3. Sprinkle the packed brown sugar evenly over the melted butter. This will become your amazing caramel layer.
4. Drain the can of pineapple rings, but SAVE the juice! Place the rings in a single layer on top of the brown sugar. Put one maraschino cherry in the center of each ring.
5. In a large bowl, whisk together the flour, granulated sugar, baking powder, and salt.
6. In another bowl, whisk the eggs, milk, 1/3 cup of the reserved pineapple juice, oil, and vanilla until smooth.
7. Pour the wet ingredients into the dry ingredients. Gently stir with a spatula until just combined. A few lumps are okay—overmixing makes a tough cake.
8. Carefully spoon the batter over the arranged fruit in the pan and smooth the top.
9. Bake for 35-45 minutes, until the top is golden and a toothpick inserted into the center comes out clean.
10. This is crucial: let the cake cool in the pan on a wire rack for only 10-15 minutes. Any longer and the topping will stick. Run a knife around the edge, place a serving plate on top, and flip it over in one confident motion. Lift off the pan and behold the magic!

Fun Twists for Different Tastes

Once you’ve mastered the classic, it’s fun to play around. Here are a few ideas we love.

For a nutty crunch, sprinkle chopped pecans or walnuts over the brown sugar layer before adding the fruit. If you have a kid who’s unsure about the cherries, just leave them out—it’s still delicious. For the adults, a tiny sprinkle of flaky sea salt on the warm topping is incredible. You can even use fresh pineapple slices if you have them, but simmer them in a little water first to soften.

Storing & Reheating (Perfect for Busy Nights)

This cake stays moist for days, making it a fantastic make-ahead dessert.

Once completely cool, cover it tightly with plastic wrap or store it in a cake carrier at room temperature for up to 2 days. For longer storage, you can keep it in the fridge for up to 5 days. My favorite trick? Gently reheating a single slice in the microwave for 10-15 seconds. It makes the caramel topping gooey and fresh-baked all over again.

Nutrition Notes

Let’s be real—this is a treat! But it’s made with real ingredients, and that’s something. Here’s a quick look per serving.

• Calories: ~380
• Total Fat: 14g
• Using pineapple in juice (not heavy syrup) keeps added sugar in check.
• The eggs and milk add a bit of protein.
• It’s a dessert we can feel good about serving for a special family moment.

FREQUENTLY ASKED QUESTIONS

Can I make this cake ahead of time?

Absolutely! Bake it, let it cool completely, and cover it well. It actually tastes even better the next day as the flavors meld. Just do the flip while it’s still warm from the oven, then store it.

My topping stuck to the pan! What did I do wrong?

Don’t worry, this happens to everyone once. Usually, it means the cake cooled too long in the pan before flipping. Next time, stick to that 10-15 minute cooling window. Also, make sure you used enough butter under the brown sugar.

Can I use a boxed cake mix?

You sure can! It’s a great shortcut. Prepare a yellow cake mix according to the box directions, then pour it over your arranged fruit and bake as directed. It turns out wonderfully.

There you have it—the ultimate retro dessert that’s stood the test of time for a reason. It’s simple, stunning, and has a nearly 100% success rate with the toughest critics (our kids!). The moment you flip that pan and reveal the glistening, fruity top is pure kitchen magic. If you love banana-based treats with a delicious crumb topping, our Coffee Cake Banana Muffins are another family favorite.

This Pineapple Upside Down Cake Classic is more than just a recipe. It’s a way to create a happy, shared memory around the table. And on those chaotic days, that’s a win we all deserve. I’d love to know if this was a hit with your family! Please leave a comment and rating below!