Pineapple Upside Down Cake (2024)

This post may contain affiliate links. As an Amazon Associate I earn from qualifying purchases. Please read my disclosure policy.

Jump to RecipeJump to Video

My easy Pineapple Upside Down Cake recipe has received hundreds of 5-star reviews, and for good reason!Made with a soft, fluffy, and simple vanilla cake base and a beautiful crown of caramelized pineapple and maraschino cherries, this classic recipe is slated to be a staple in your baking repertoire. Includes a how-to video.

The Perfect Easy Pineapple Upside Down Cake

There are a lot of cake recipes on this blog, and a fair share of unique cake recipes as well (zebra cake and my ice cream cake certainly come to mind). However, I’m not sure any is quite as unique and demanding of attention as this pineapple upside down cake.

A true showstopper, it’s a moist and flavorful vanilla cake crowned with golden, caramelized pineapple rings and cherry jewels. It’s also surprisingly simple to make and you don’t have to bother with frosting or decorating the same way you would a classic layer cake.

Why You’ll Love This Recipe

Easy to make. No fussy techniques, no fancy ingredients, this recipe is a good one for beginners and well-seasoned bakers alike.
A true classic. This is the classic dessert you might remember from your childhood.
It’s beautiful! There’s no denying a freshly flipped upside-down cake is a sight to behold; both its beauty and taste make it a showstopper for any dessert table.
Unique. From the unique way in which it’s baked (upside-down!) to the caramelized crown of tropical fruits, this recipe stands out from your basic cake recipe.

I think you’re going to love this one, so let’s get to it.

What You Need

The cake is made of basic pantry staples, nothing fussy, fancy, or difficult to find, and the beautiful bottom-turned-top is a stunning crown of caramelized fruit. You’ll recognize most of the ingredients, but as you know I like to discuss them a bit before we get to the baking.

Pineapple Rings. You can use fresh or canned rings. Canned are the traditional and easier choice, and are what I use here.
Maraschino cherries. Don’t substitute fresh cherries. Maraschino cherries add classic are essential as they’re soaked in a syrup that lends much flavor to the surface of the cake. If you do opt to substitute a fresh cherry, just expect a different flavor.
Sugar. The topping is made with light brown sugar, which lends a subtle rich flavor to the caramelized topping (thanks to the small amount of molasses in the sugar). The cake uses only granulated sugar.
Flour. I use all-purpose flour, but you may substitute cake flour. If doing so, how you substitute depends on how you weigh your ingredients. If you use a scale, the weight will be the same for cake flour, but if you are using a measuring cup, you will need a bit more cake flour than the recipe calls for. Here is a helpful resource for substituting cake flour for all-purpose flour.
Milk. My preference is to use milk in the cake batter. I’ve tried the recipe with pineapple juice (leftover juice from the can of pineapple slices) and did not enjoy the cake as much when made this way. However, a number of readers have written that they’ve substituted all or half of the milk with pineapple juice and enjoyed it that way, so feel free to experiment!

SAM’S TIP: Make sure to blot your pineapple slices well with paper towels before placing them in your pie plate. This will absorb any excess liquid. If you skip this step it could make your cake soggy.

This section is just an overview of the ingredients I used and why (for those of you who are as nerdy about what goes into making a cake as I am!). For the full recipe please scroll down to the bottom of the post!

How to Make the Best Pineapple Upside Down Cake

The steps are simple and straightforward and I don’t think you’ll struggle, but let’s go over them before we begin:

Prepare your pan. Pour melted butter into the pie plate and make sure you spoon or brush a bit up the sides of the plate as well. Sprinkle brown sugar evenly overtop the butter.
Layer the fruit. Arrange the pineapple rings and cherries over the pie plate and around the edge, too.
Make the cake batter. This is a simple but sturdy vanilla cake batter (the same one used for my marble cake) that you’ll make by creaming the sugar and butter, adding eggs and vanilla, then gradually alternating adding the dry ingredients and milk until the batter is combined.
Bake. To avoid the cake over-browning, you’ll want to check it at the 30 minute mark and loosely tent with foil (I also use this technique in my banana cake).
Flip & serve. Let the cake cool for just 10-15 minutes before inverting onto a serving platter (more on that below). Don’t let the cake cool too long, or it may stick to the pie plate.

Avoid a too-dense, dry cake: This recipe is a bit denser than your average cake (it must be to not collapse under the weight of the fruit once flipped) but it should not feel too dense or dry. There are two culprits to watch for that could cause your cake to turn out this way: 1) Over-mixing the dry ingredients (just stir until the wet and dry ingredients are combined, don’t overdo it!) and 2) over-baking the cake. Even a few minutes too long in the oven can make your cake dense and dry. Some ovens also run hotter than they say they are, so watch for that too as this can cause your cake to cook too fast and dry out!

How to Flip this Cake

This was a popular question when I first published this cake and I want to address it here (though I also show how to flip the cake in my video). The biggest takeaways should be to make sure you use oven mitts and use a plate that’s larger than your cake so that any juices don’t run off the side!

Allow your cake to cool for 10-15 minutes before you attempt inversion. If any of the cake has baked into the edge of your pie plate or cake pan, first use a knife to gently loosen the edges and free them from the pan.
Place your cake platter (or any plate that’s larger than your cake) over the pan — plate surface should be facing your vanilla cake layer.
Using oven mitts(it will be hot!)carefully and firmly grip both the side of the cake platter and the cake pan on either side.
Carefully but quickly flip everything over so that the bottom of the cake pan is facing upwards, and then set down your cake platter and carefully remove the cake pan (careful, it will still be hot!)

And that is it!This cake tastes best warm, so while you still want it to cool a bit, I don’t recommend waiting too long to dig in or making it very far in advance of serving!

Frequently Asked Questions

Can I use a cast iron pan to bake this?

Yes! Many of my readers have baked their own cakes in 9-10″ cast iron skillets instead of the pie plate. One thing worth noting is that the baking time will likely be shorter, as cast iron will cook much faster. Keep an eye on your cake if baking this way and check it sooner than indicated in the recipe.

How do I keep my cake from sticking to the pan?

The butter and sugar coating should keep the cake from sticking to the pan. However, before flipping the cake I like to take a butter knife and, if any place where I see actual cake (not fruit) making contact with the pie plate, I gently loosen it so that it won’t stick. The fruit should also come out quite easily, but if a ring or tow sticks, no big deal, just gently pry it from the pie plate and place it back on the top of the cake, there should be a clear indent showing you exactly where it belongs. ☺️

Pineapple Upside Down Cake

This show-stopping retro pineapple upside down cake recipe is made with simple pantry staples, yet yields a moist and fluffy cake topped with gorgeous cherry-filled pineapple rings! Recipe includes a how-to video.

4.93 from 512 votes

Print Pin Rate

Course: Dessert

Cuisine: American

Prep Time: 25 minutes minutes

Cook Time: 45 minutes minutes

Ingredients

Topping

▢ ¼ cup (60 g) salted butter melted
▢ ½ cup (100 g) brown sugar light or dark (I usually use light) tightly packed
▢ 10 pineapple slices patted dry (a 20oz can is typically enough)
▢ maraschino cherries

Vanilla Cake

▢ ½ cup (115 g) unsalted butter softened to room temperature
▢ ¾ cup (150 g) granulated sugar
▢ 2 large eggs room temperature preferred
▢ 1 teaspoon vanilla extract
▢ 1 ½ cups (195 g) all-purpose flour
▢ 1 ½ teaspoons baking powder
▢ ¼ teaspoon salt
▢ ½ cup (120 ml) whole milk room temperature preferred

Recommended Equipment

▢
Pie plate
▢
Mixing bowls

Instructions

Preheat oven to 350F (175C)
Pour melted butter into 9.5-10" pie plate or deep cake pan, make sure it entirely covers the bottom of the pan and use a spoon or spatula to grease the sides of the pan.
¼ cup (60 g) salted butter
Sprinkle brown sugar evenly over butter mixture. Arrange pineapple slices over the bottom of the pan, slice leftover slices in half and arrange up the sides of the pan, as seen in photo.
½ cup (100 g) brown sugar, 10 pineapple slices
Place cherries in center of pineapple rings and as desired in empty spaces. Set aside.
maraschino cherries
To prepare vanilla cake, beat butter and sugar in medium-sized bowl until creamy and well-combined.
½ cup (115 g) unsalted butter, ¾ cup (150 g) granulated sugar
Add eggs, beating one at a time until combined.
2 large eggs
Stir in vanilla extract.
1 teaspoon vanilla extract
In a separate bowl, whisk together flour, baking powder, and salt.
1 ½ cups (195 g) all-purpose flour, 1 ½ teaspoons baking powder, ¼ teaspoon salt
Alternate adding flour and milk to the wet ingredients, starting and ending with flour and mixing until just combined after each addition (I prefer to do this part by hand with a spatula to be sure not to overmix).
½ cup (120 ml) whole milk
Pour batter evenly over prepared cake pan over the pineapple/cherry layer.
Bake on 350F (175C) for 30 minutes. At the 30 minute mark, loosely cover with foil and continue to bake (still on 350F/175C) for another 15 minutes, until a toothpick inserted in the center comes out mostly clean with few crumbs (total cook time for cake will be 45 minutes).
Allow to cool for 10-15 minutes and then carefully invert cake onto serving platter (careful, it will still be very hot!).
Allow to cool before cutting and enjoying, but don’t wait too long as this cake tastes wonderful (best!) warm from the oven!

Notes

Milk

I use and recommend whole milk, but many readers have substituted lower-fat milk or almond milk with success. Some readers have substituted the milk in this recipe with pineapple juice, I think the difference in taste is negligible and prefer the texture of the cake when made with milk, but it can be done.

Gluten Free

Readers have commented that they have successfully made this recipe by using a 1:1 substitution of all-purpose gluten free cup4cup flour.

Serving & Storing

Pineapple upside-down cake tastes best fresh and doesn’t keep as well as most layer cakes. However, if you wish to keep it, cover it with foil or plastic wrap or place in an airtight container and refrigerate for up to three days. You may also wrap tightly and freeze for several weeks.

Nutrition

Nutritional information is based on third-party calculations and should be considered an estimate only. Actual nutritional content will vary based upon brands used, measuring methods, cooking method, portion sizes, and more.

Tried this recipe? Show me on Instagram!Mention @SugarSpun_Sam or tag #sugarspunrun!

I originally shared this recipe in 2017. It has been updated to include more helpful photos, notes, and information and a new video, but the recipe remains the same.

More Cakes You Might Like

Chantilly Cake
Tres Leches Cake
Strawberry Cake
Lemon Blueberry Cake