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 – whats not to love?

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 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 having the reputation of making the moistest pineapple upside down cake around!

You’ll need: Cake mix (Yellow or Pineapple Supreme), cherries, pineapple slices, brown sugar, and butter. You’ll also need the ingredients your cake mix calls for.

Turn your oven on 350 and while we are mixing up the cake batter, place a stick of butter in a 9×13 inch pan and place in 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 and use that as part of the water. My can of pineapple yielded just over 3/4 of a 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. Set aside.  Adding in this juice is going to make our cake so flavorful!

Once your batter is mixed up, remove pan from oven. Your butter should be nice and melted like this.

Sprinkle about a cup of brown sugar over the butter in your pan.

Until it looks like this. If you need to use more than a cup you can.

Place your pineapple slices on top of the cake, putting a cherry in the center of each one. If you don’t have cherries, don’t feel like you need to go buy them special just for this, just make it pineapple only and it will still be delicious.

Gently pour your cake batter over the pineapple. Now place this in your 350 degree oven for about forty five 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 ten minutes and then turn out. A cutting board is the 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 transporting.

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 pineapple upside down cake today. 😉

Super Moist Pineapple Upside Down Cake

Ingredients

• 1 box Yellow Cake Mix or Pineapple Supreme Cake Mix
• 1 can Pineapple Slices make sure your can has at least six. I get the large so I can eat two!
• 1 stick butter
• 1 jar of cherries optional
• 1 C Brown Sugar

Instructions

• Preheat oven to 350 degrees. Place stick of butter in 9×13 inch pan and put this in the oven while it preheats for just a few minutes, until butter is melted. Once butter is melted, carefully remove from oven and sprinkle brown sugar all over top of melted butter in pan. Place pineapple slices on top of brown sugar, reserving pineapple juice. Place a cherry in the center of each pineapple slice.

• Prepare cake mix as directed on package, substituting pineapple juice for some of the water called for. Slowly pour cake mix over pineapple slices and cherries.

• Bake at 350 for forty five minutes, or until toothpick insterted in cake comes out clean.

• For moister cake, place toothpicks in corners and center of cake, then cover with cling wrap or aluminum foil before it has cooled completely.

This post was originally published in 2009. I updated the photos in 2020.

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