Easy Pineapple Upside-Down Cake

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!

Recipe Ingredients

• 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.

Recipe Tip

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.

Storage

• 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.

Recipe Notes

• 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 pineapple chunks 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:

Pineapple Cobbler

Cherry Pineapple Dump Cake

Pineapple Poke Cake

Pineapple Pumpkin Smoothie

Vanilla Wafer Pineapple Pudding 

 

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