Super Moist Pineapple Upside Down Cake

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Pineapple Upside Down Cake is a regular aound most southern dinner tables and when I was a girl, 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! Everyone whose had my pineapple upside down cake goes on and on about how moist it is and how they just don’t know what I do to get it so moist! Today, I’m going to share my secret with you – and the fact that it was a complete and total mistake that led me to having the reputation of making the moistest pineapple upside down cake around!

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You’ll need: Cake mix (Yellow or Pineapple Supreme), cherries, pineapple slices, brown sugar, and margarine (not pictured).

Note: The only reason why I have name brand pineapple slices for this recipe is that I was at my mother’s earlier and raided her pantry for them :). Y’all know I don’t buy name brand pineapple!

You’ll also need the ingredients your cake mix calls for.

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Turn your oven on 350 and while we are mixing up the cake batter, place a stick of margarine in a 9×13 inch pan and place in preheating oven so it melts.

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Now, we’re going to go by tbe 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.

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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.

Then we add the vegetable oil and eggs according to the box and mix it up well.

Adding in this juice is going to make our cake so flavorful!

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

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

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

Or if you eat half of it on the way to the pan….

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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 :).

Thank goodness there is always a slice or two of pineapple left in the can!!! I’m eating that right now…

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Gently pour your cake batter over the pineapple.

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Until it looks like this. Now place this in your 350 degree oven for about forty five minutes.

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I have cake boards which I cover in foil and use to turn my cakes out onto.

dscn4194Its just a thin piece of wood I had my dad cut for me.

I have them in all different sizes (I often like to make really big cakes!) and they come in so handy!

(This one was in my daughter’s room. I covered it in foil before the photo so you wouldn’t see all of the stick people she drew on it with her markers. We’re trying to look professional here ~laughs hysterically~)

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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).

Let sit on the counter for ten minutes.

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After about ten minutes, turn your cake pan upside down onto your cake board (or whatever you are turning it out onto).

I usually make a 13×18 inch pineapple upside down cake so thats why my board is so big.

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Oh my lord. I am about to eat my computer.

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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).

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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.

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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…

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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…

Hey, whatever works for you! ~grins~

Pineapple Upside Down Cake


  • 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 margarine
  • 1 jar of cherries (optional)
  • 1 C Brown Sugar

In 9×13 inch pan, melt butter. Once butter is melted, sprinkle brown sugar all over bottom of 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, cover before it has cooled completely.


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Comments

  1. Denise says

    I just made this with an extra half box cake mix and ingredients. It was super delicious and everyone loved it!!! I added two egg whites with the extra half box to make the cake extra fluffy.

  2. Connie Smith says

    I love it! I knew somebody said they were going to make and it take it for a ride. (Is that really part of the recipe?) How far do we need to drive and just how many bumps for it to be done? ;-)

  3. Robin K. says

    Christy, I made your recipe just as you show and it was the best ever. My husband who normally would prefer a chocolate cake loved it as well and now when I say I’m going to make the pineapple upside down cake he says “oh good” :)

  4. says

    For Nancy ~ Butter will work just fine and probably up the flavor a titch.

    Christy, I’m with Connie and need to know how long of a ride and how many bumps ’til it’s done?

    Seriously, thanks so much for another hilarious story! I already know the recipe will be fabulous; it’s how I already make mine except for the ride at the end. I think I’ll try Mike’s suggestion and use evaporated milk next time. (I always cook ours in a big cast iron skillet, so I’ll just keep doin’ that.)

    Oh! And Christy, is that a vintage cake pan you’re using here? It sho’ is purty! :-D

  5. louanne says

    I make the same way , also they make a pineapple cake mix now if you can find them, I still add the extra juice. I have also used crushed pineapple it works great and you get pineapple in every bite .

  6. Vicki in GA says

    Margarine?
    Why?

    What kind do you use?

    Reason I’m asking is I haven’t had margarine in the house for years and years.
    In fact, since I left home when I was 18 years old. I’m now 66!

  7. Jen says

    Anyone ever try to make pineapple upside-down cupcakes??? I love the cake but I’m the only one of my family that does and the last thing I need is a whole cake in the house.

  8. Laura says

    This cake was delicious! I made it yesterday for my Dad’s 82nd birthday. I did use butter instead of margarine, and I added a few half slices of pineapple (everyone likes the pineapple on top!) Thanks for something so good & easy!

  9. Jasmin says

    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

  10. Hope says

    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

  11. Ginny says

    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!

  12. Jill says

    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!

  13. Emilee says

    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.

  14. Karen says

    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!!

  15. Aicha says

    My husband has been asking for a pineapple upside down cake for forever. I found this recipe and made it today. First time making it and my husband said it was SO good. I used condensed milk and the juice from the can like others suggested. Very yummy.
    I’m going to try individual cakes in a muffin tin next time.

  16. katlvr99 says

    Thank you for posting this recipe. I planned on making a Pineapple Upside Down Cake from scratch, but, oooopppssss, silly me, I forgot to buy Vanilla. Quick thinker that I am sometimes, I decided too look for a recipe on the internet using a box cake mix.

    I haven’t tried it yet, but I wanted to thank you not only for posting it,but for making me laugh. You never know who needs it. Thank you.

    Just waiting for me cake to cool…….yummmmmyyyyy.

  17. katlvr99 says

    Magnificent, it came out excellent. Very, very FLAVORFUL AND MOIST. I also put a can of mixed fruit , drained with the pineapple as I didn’t have but one can of pineapple and it just didn’t seem like enough pineapple.

    Thank you again for sharing.

  18. Kevin says

    I made this cake for my wife since pineapple upside down cake is her fav. She loved it! She thought it was the best pineapple upside down cake she ever tasted. I was her hero! LOL!

  19. Laura Smith says

    What a super easy cake and the house smells delicious. My kids are hanging around the oven waiting for it to finish baking. (Didn’t tell them it needs a nap before they can devour it). I used pomegranate instead of cherries in the pineapple rings. Hoping it turns out as wonderful as all the previous reviews. Thanks for posting.

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