Old Fashioned Pineapple Upside Down Cake

This classic dessert recipe comes from a mid 1930s cookbook. I've adapted the recipe a bit just to make it easier. I hope you enjoy this old-fashioned favorite!

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Table of Contents

• ❤️ Why you'll love it
• 🧾 Ingredients
• 📖 Variations
• 🔪 Instructions
• 🥫 Storage
• 💭 Things to know
• 👩‍🍳 FAQs
• 📚 Related recipes
• 🍽️ Serve with...
• 📞 The last word
• 📖 Recipe
• 💬 Comments

❤️ Why you'll love it

• The classic recipe tastes just like when mom used to make it!
• Bake in a pan or a cast iron skillet—whatever you prefer.
• Easy-to-follow cake recipe, even for inexperienced bakers!

Pineapple-upside down cake is made with airy, buttery cake, juicy pineapple slices, and sweet maraschino cherries. It's all baked in a sticky brown sugar glaze.

This is a dessert fit both for casual family dinners and special occasions.

Decades of food fads have come and gone, but this old-fashioned recipe has stuck around for a reason. It's simply a good cake—no ifs, ands, or buts about it!

🧾 Ingredients

This is an overview of the ingredients. You'll find the full measurements and instructions in the green recipe card (printable) at the bottom of the page.

📖 Variations

Every family thinks that their original recipe is the best pineapple upside down cake—and that's part of what makes it special! Here are some of the most popular variations to try:

• Upgrade the vanilla flavor by swapping extract for vanilla bean paste!
• Or, replace the vanilla with almond extract.
• You can use bourbon instead of rum if you prefer it.
• Use fresh pineapples and cherries instead of canned ones.
• Instead of pineapple juice, you can use regular milk or sour cream in its place (though, I prefer the subtle pineapple flavor in the cake!)
• Some people like to add a pinch of nutmeg or cinnamon to the brown sugar mixture.
• Pecans add a deliciously buttery crunch to the cake, but you could also use macadamia nuts, or omit them altogether.

🔪 Instructions

This is an overview of the instructions. Full instructions are in the green recipe card at the bottom of the page.

1. Spread the sugar and melted butter mixture in the bottom of the pan.
2. Add the pineapple rings, cherries, and pecans.
3. Spoon the cake batter over top of the fruit and nuts.
4. Bake and flip the pineapple upside-down cake onto a serving plate.

🥫 Storage

Put leftovers in an airtight container, or cover them with plastic wrap.

Here's my secret: use tin foil if you're trying to hide a few slices all to yourself... but don't be surprised if your family still sniffs 'em out!

Store the pineapple upside down cake leftovers in the refrigerator for up to three days.

You can also freeze them for about a month. (Just thaw in the refrigerator before enjoying.)

💭 Things to know

Expert Tip: Splurge a bit and use really good pineapple—the cake's named after it, for goodness sake! The vintage recipes used pineapple in heavy syrup, and I think it tastes best that way!

• Don't use canned chunks of pineapple. They're a little too watery and tend to fall out of the cake during the flipping process!
• Fancy Luxardo cherries are soaked in a super thick, cherry syrup—they're my favorite in this recipe!
• Cold eggs separate more easily than those at room temperature.
• I like to crack the eggs over a separate cup, first, placing the egg yolk in a small bowl and dumping the egg white from the cup into another bowl after each egg. That way, in case you get any shell or egg yolk in the white, you don't ruin a whole batch!
• Feel free to use salted or unsalted butter, whatever you have.
• If you can flip your bowl upside down over your head and the egg whites don't fall on your face, they're properly whipped to stiff peak stage.
• The stiffly beaten egg whites make a typically dense cake super delicate and fluffy. Very carefully fold them into the batter using a spatula, and only mix until just combined. Too heavy of a hand will cause the air you just whipped into the whites to deflate.
• The cake can overcook really quickly, so don't get distracted during baking!
• When testing for doneness with a toothpick, don't poke all the way into the caramel layer at the bottom of the skillet. Just go far enough to test the cake. Some moist crumbs are fine, but you shouldn't see any wet batter.

Here are some tips to cleanly flip the cake over and upside right:

1. Cool the cake for around five minutes, but no more than ten, so that the sauce at the bottom of the pan can thicken up a bit.
2. Grab a pan larger than the one you baked the cake in, or another serving vessel large enough to hold the whole cake.
3. Place the pan or serving plate on top of the pineapple upside-down cake pan/skillet, with the top of the plate facing (what will become) the bottom of the cake.
4. Hold the two dishes together firmly, and confidently flip them over. It helps to move in one, swift motion, rather than a slow, unsteady turn.
5. Set the serving plate down on the counter and let it sit as is for a minute so that the caramelly pineapple topping has time to "unstick" itself from the bottom of the pan.
6. Finally, gently pull the baking pan off from the top of the cake and reveal your beautiful and delicious pineapple cake!

👩‍🍳 FAQs

📚 Related recipes

• America's favorite cake with a twist—Pineapple Upside Down Cheesecake is everything you crave about the classic, but creamy!
• No-Bake Pineapple Cream Cheese Pie is light, fluffy, fruity, and perfect for summer—but best of all: it only takes about five minutes to prep!
• Sheet cake recipes are so simple to make, and this Lemon Sheet Cake is no different! However, it's the fluffy, light, lemony whipped topping that makes it oh-so-cravable.

🍽️ Serve with...

Pineapple upside down cake is a classic. I like it with 1960s entrees like meatloaf or salisbury steak. I'll add some fried potatoes and maybe some broccoli casserole to round out the meal.

📞 The last word

If you're looking for the best pineapple upside down cake from scratch then you've found it!

Pineapple upside down cake recipes are iconic classics that come with many variations.

The original one is my favorite, there's just something about a thick, caramel syrup combined with juicy pineapple, and feather light sponge cake that no other recipe can touch.

I love this for dessert when we have the burrito casserole. There's just something about the combination.

Next time try this chocolate upside down cake.

If you click on the number of servings in the recipe card you can adjust the measurements up or down for the exact number of servings you need. Don't forget that you can click on "add to collection" to save it to your own, private recipe box!

If you love this recipe please give it 5 stars! ⭐️⭐️⭐️⭐️⭐️

📖 Recipe

This post and recipe have been updated from the original 2008 version for better user experience. Last updated August 31, 2022 for new images and editorial content.