All it takes is five ingredients to make my easy pineapple upside-down cake recipe, which includes a super moist and buttery yellow cake with juicy glazed pineapple slices and a cherry on top (yes, really).
Pineapple upside down cake was a regular around most dinner tables when I was a girl, and it was even a regular in the school cafeteria! The flavor of a buttery cake, topped with brown sugar and that glazed slice of pineapple on top with a cherry in the center – what’s not to love? The brown sugar caramelizes on top of the cake so each bite is fluffy, moist, and so deliciously sweet.
The way I make this cake is as easy as they come and you can pull off a nostalgic showstopper in no time flat! Folks usually ask me how I get it so super moist and the secret is a crazy trick I use. Today, I’m going to share my secret with you, along with the fact that it actually began as a mistake and led me to have the reputation of making the moistest pineapple upside-down cake around!
- Cake mix (yellow cake or pineapple supreme plus ingredients)
- Maraschino cherries
- Pineapple slices
- Brown sugar
- Unsalted butter
How to Make Easy Pineapple Upside Down Cake
Turn your oven to 350 and while we are mixing up the cake batter, place a stick of butter in a 9×13-inch baking dish and place it in the preheating oven so it melts.
Now, we’re going to go by the box instructions on how to make our cake with one exception.
Drain the juice from your pineapple can and use that as part of the water. My can of pineapple yielded just over a 3/4-cup of juice so according to my package, I’m going to add enough water to make 1 1/3 cup of liquid (in place of plain water) to add.
From there, simply follow the directions on your box of cake mix to prepare the mix and set it aside. Adding in this pineapple juice is going to make our cake so moist and flavorful!
Once your batter is mixed, remove the pan from the oven. Your butter should be nice and melted like this.
Sprinkle about a cup of brown sugar over the melted butter in your cake pan.
Until it looks like this. If you need to use more than a cup you can.
Arrange pineapple slices on top of the sugar, putting a maraschino cherry in the center of each pineapple ring.
If you don’t have cherries, don’t feel like you need to go buy them special just for this. Just make it with pineapple slices only and it will still be delicious.
Gently pour your cake batter over the canned pineapple slices.
Now place this in your 350-degree oven for about 45 minutes.
Once your cake looks done, make sure you can press on the center and it springs back a bit before you remove it from the oven (or just use the toothpick trick. Insert a toothpick in the center, if it comes out clean your cake is done).
Once you remove the cake from the oven, let it sit in the pan for 10 minutes, and then invert the cake onto your surface of choice.
A cutting board is a perfect thing to serve this cake on if you don’t have a tray or cake holder big enough. I just go with the cutting board because it is sturdy enough for transport.
Tip For Super Moist Cake
Now here is how I accidentally made the moistest pineapple upside-down cake ever.
I made one, was running late, and had to take it to dinner at someone’s house. In order to transport it, I stuck toothpicks in it all over, like in this picture (look closely to see toothpicks).
Then I covered it in cling wrap before actually letting it cool (running late, ya know…). I tucked it in the back seat of my car and headed off while all of that lovely pineapple and brown sugar-scented steam made a futile attempt to evaporate.
Kinda like this.
Now everyone knows you’re supposed to let cakes cool completely before covering, right? Well, off I went, traveling along while my poor cake oozed steam only to have it accumulate on the wrapping and drop back down into the cake as I hit bump after bump. When I got there, my cling wrap was dry again and my cake…well…
It was the moistest pineapple upside-down cake anyone had ever eaten. 🙂
Since that day, I’ve gotten complaints anytime I don’t fix it this way so we just keep on repeating history.
And you know what? I think you deserve a slice of easy pineapple upside-down cake today. 😉
- Store leftover pineapple cake in an airtight container in the fridge for up to 5 days. If you can believe it, the cake tastes even better a few days later as the caramelized pineapple juices continue to soak into the cake.
- You can also freeze leftovers for up to 3 months. Thaw slices in the fridge overnight before serving.
- Serve your pineapple upside-down cake with whipped cream (here’s my homemade recipe) or a scoop of vanilla ice cream.
- If you have leftover pineapple, chop the slices up into and add them to the cake batter.
- I recommend using canned pineapple instead of fresh pineapple, as we want the can’s pineapple juice to give the cake extra pineapple flavor.
- If you have trouble flipping your cake, run a thin butter knife around the edges and be patient. Banging or thrusting can break the cake, which no one wants!
- If your pineapple slices and cherries are extra moist, quickly blot them with a paper towel before arranging them over the brown sugar. The extra moisture can lead to a wet cake.
- For extra flavor, sprinkle ground cinnamon over the brown sugar.
- Substitute the maraschino cherries for candy ginger pieces or cranberries for something different.
- To make this gluten-free, simply use a gluten-free cake mix instead.
You may also enjoy these pineapple recipes:
Vanilla Wafer Pineapple Pudding
- 1 box yellow cake mix or pineapple supreme cake mix
- 1 can pineapple slices
- 1 stick butter
- 1 jar cherries optional
- 1 cup brown sugar
- Preheat the oven to 350 degrees. Place the stick of butter in a 9x13-inch baking dish and put this in the oven while it preheats for just a few minutes until the butter is melted.1 stick butter
- Once the butter is melted, carefully remove the pan from the oven and sprinkle brown sugar all over the top of the melted butter. Place the pineapple slices on top of the brown sugar, reserving the pineapple juice. Place a cherry in the center of each pineapple slice.1 can pineapple slices, 1 jar cherries, 1 cup brown sugar
- Prepare the cake mix as directed on the package, substituting pineapple juice for some of the water. Slowly pour the cake batter over the pineapple slices and cherries.1 box yellow cake mix
- Bake at 350 for 45 minutes or until a toothpick inserted in the cake comes out clean.
- For an even more moist cake, place toothpicks in the corners and center of the cake and cover it with cling wrap or aluminum foil before it has cooled completely.
I just now made this cake for a cookout this afternoon. It came out of the pan beautifully! It’s sitting underneath the plastic wrap now. I can’t wait to see what it tastes like! Thank you for sharing your recipe!!
I hope everyone enjoyed it Karen!!
Can I make this the night before? Or is it better when just made?
Need to know! Soon!
Pineapple upside down cake is my favorite cake of all time, and I used to make it very similar to this, but I have found a way to make it even better. Use crushed pineapple instead of rings, and no cherries. I hand mix the batter with a wisk, and instead of using oil, use the same amount of extremely softened butter or margarine that your cake mix calls for. I use whatever juice I can squeeze out of the crushed pineapple and add water to make it one cup as well. After your batter is mixed, stir in my secret ingredient, 1 tsp of almond extract. Make sure you bake it in a skillet for the best southern pineapple upside down cake ever.
A tip from my my mother in law. Put the pineapple and cherries in after you melt the butter in the pan but before putting in the brown sugar, it makes the top look prettier since the sugar won’t brown up the pineapple and cherries as much. Very nice as a round cake presented on a nice glass plate. I love the idea of using crushed pineapple and condensed milk too! Your pictures and story were great, thanks for sharing them!
HI Jill. Try evaporated milk instead of condensed milk or you’ll have a pineapple upside down tres leches cake (which doesn’t sound so bad if you think about it).
I made this tonight, and my family loves it! I also left the pan on the cake as it cooled. My son who hates coconut and anything that feels “funny” in his mouth told me that he didn’t like the topping (I used crushed pineapple). After I told him what it was, he got another HUGE piece! I am bookmarking this page! Thanks for the recipe!
Omg!!! Ive never made a pineapple upside down cake and this was the easiest recipe i had found. I made this cake this morning and Omg wow unbeliveable moistness and sooooo delicious! I didnt have whole pineapple slices though so i used a can of crushed pineapple. I love how you provide step by step instructions and pictures 🙂 simply amazing moist pineapple upsode down cake and not such a bad turn out for me considering its my first pineapple upside .down cake. Do you have a recipe for homemade snickers bars? or have you ever attempted to make them? keep up the awesome work and the fantastic illustrations of your recipes
I made this recipe and it was a HUGE hit! thank you so much for posting it, It really did come out moist. Instead of using the wrap as you suggested, I just placed the pan back on the cake as it cooled. Worked the same way