Super Moist Pineapple Upside Down Cake
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!
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.
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.
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.
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!
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.
Or if you eat half of it on the way to the pan….
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…
Gently pour your cake batter over the pineapple.
Until it looks like this. Now place this in your 350 degree oven for about forty five minutes.
I have cake boards which I cover in foil and use to turn my cakes out onto.
Its 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~)
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.
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.
Oh my lord. I am about to eat my computer.
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…
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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Posted by Christy Jordan
on Feb 4 2009. Filed under Cake.
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I love PUC! I make it in my Mama’s cast iron skillet but only because thats the way she always did it.. and ya know if I did it any different my daddy would not think it was any good.. cause change is bad.. baaad I tell ya! I too use the pineapple juice as part of the water. Good stuff Maynard.
I’ve used dark brown sugar but it was kinda nasty. I’ve also used the Pineapple cake mix..something else I won’t do again.
Somehow, it doesn’t sound so appealing when you call it PUC. (Pronounce it phonetically!)
LOL! Christy really needs an edit function on here…
~snickers~
HEY BILL!!!
You know, if you ever don’t comment on a recipe, I get to thinking I’ve done something wrong! lol
Cast Iron skillets make prime pineapple cakes, but I like the really big’uns!! lol
Great minds think alike on the pineapple juice, too!!!!
ATTABOY! ~giggle~
so I don’t worry about being all pc!
Anyone else I would have worried that might sound condescending to, but you’re just “our Bill”
Gratefully,
Christy
I use my cast iron skillet too. I also use the Yellow butter cake instead of regular cake and before I add the pineapple layer to the butter and brown sugar, I add pecans–now it is Southern!
Great cake any way ya slice it. CajunLou
Love thos pecans but my doctor said no.
(
I was wondering about the sugar. I have both in my pantry and considered using dark brown. I’m glad I didn’t. The cake is in the oven now and I can’t wait.
What a great idea to cover the cake with wrap!! I’m going to make this tonight for sure..yummmy
YAY!!! Let me know how you like it and have a great dinner!!!!
Gratefully,
Christy
OMG! If I hadn’t given up on any hopes of weight loss before this recipe then this one would have done it for sure! This Yankee is *addicted* to all of Christy’s recipes and this one will be added to the favorites. I am now in touch with my inner southerner (who is well fed and very happy LOL).
What did I do before I found you? Well other than take out…
Oh Les, you just made me grin so big my cheeks are hurting!!! Keep that inner Southerner pushed up to the dinner table for me, I’ll go around and refill tea glasses and keep the plates full!!!!
You’ve just absolutely filled me with joy with this comment!
Gratefully,
Christy
OH MY GOSH!!!! I have been so hungry for a pineapple upside down cake lately. I even looked at a mix for it 2 nights ago at the store. I have never made one so didn’t realize how easy it would be. This is going on my list to make really soon. Thanks for all the wonderful recipes on you blog. I get so tired of the same old thing–now we can have new stuff regularly thanks to you. I am from Louisiana so I do gumbo, jambalaya, creole and such all the time. I love good old southern food!! Thanks again. Sheila
OOOOOOOOOOOOOOOOOH yeah, easy peasy!!!! AND YOU DESERVE A PINEAPPLE UPSIDE DOWN CAKE!!!
I see how hard you work, I see what all you do for others, by golly you’ve earned this!!!
Thank you so much for reading Southern Plate and taking the time to comment!!!! I really appreciate you, Sheila!!!
Gratefully,
Christy
My birthday is coming up on the 25th and I swear- I have been looking thru your site and I have about 9 cakes i want to make for my birthday cake- I cant POSSIBLY choose between them!!!!
I’m on a DIET for goodness sake and my B-Day cake has to be super-special for me to go off it for cake.
I’m a chocoholic(love, love, LOVE Dark chocolate and the more the better) but I also LOVE pineapple and coconut as well and the cake recipes just keep on coming!!!!!!!!
What am I going to do???????
Suggestions for me for “THE SUPREMELY BEST BIRTHDAY CAKE EVER”??????
Girrrl, I feel your pain here!
My birthday is next week and not only am I gonna have to bake the cake (if I decide I want one) but I am also going to be having a birthday/pity party at home since it will be just me and the two kids with the husband off at a conference in Disney World. I have a million things to do that day with school, home, SP, and chauffeuring kids. Although normally I really try to be optimistic (and succeed!), I gotta tell ya, that birthday is gonna suck (for lack of a better word)and this is the first year I have dreaded my “special day”.
Now you know darn well I’m gonna milk that one for the next few decades – at least!
Hmmmm, let me think of my personal favorites for birthday cakes.
1. Daddy’s Coconut Cake (Wow,is this good! I wish I could just make it in a big old vat and dive in!)
2. Yellow Cake With Old Fashioned Peanut Butter Icing (see story in that post to understand)
3. Mandarin Orange Cake (alright, this might be my first choice!)
4. Coca Cola Cake (If you are a chocolate lover – stand back and prepare to die happy!)
5. Good N Easy Cake (the homemade whipped cream in that recipe is a must!!!)
6. Butterfinger cake. Okay now, if you are baking it yourself and you have never had butterfinger cake, I have to make this my top one to suggest to you because it is INCREDIBLY easy and I cannot even begin to tell you how incredibly decadent it tastes.
Wow, basically I was no help here, lol!
All these recipes are on the site, though! lol
HAPPY BIRTHDAY!!!
Happy Happy Happy Happy Birthday, BIRTHDAY!
Happy Happy Happy Happy Birthday, BIRTHDAY!
Happy Happy Happy, Happy Happy Happy Happy!
Happy, Birthday, To you!!!!!!!!!
(it sounds better when I sing it instead of typing it!)
Christy, Happy Birthday next week, how you going to get all those candles on a cake? (hahahaha) smiles: Love you site and love your post and humor…your awesome
norm
Awwww- How sweet!!! Thanks Christy!!!
I sing so badly it would even sound bad in typing!!
but Happy Birthday to YOU as well…
And yes- every one of those cakes made it to my list along WITH the Chocolate Velvet Cake.
I have to work on MY birthday as well this year- so I’ll be making my cake the weekend after….or the two days before. (Notice I’m taking TWO days instead of just the one birthday to make up for me having to work on the actual DAY. Have to compensate somehow).
Some times my Daughter makes me a cake- but last year she didn’t and i didn’t get one at all…….so this year I’m making sure I get a cake by doing it myself.
I’ll be turning 49…….Ummmm, I meant 27….yes- that’s it- 27.
Oh- btw- do you have a secret recipe for Chocolate Fudge cake with Chocolate frosting that you might share with us?
I like Coca Cola cake- but I really like the thick fudgy kind of frosting- not the pouring kind. And altho extremely rich- Coca Cola cake just isn’t dark chocolate enough for my BIRTHDAY cake!!!
Thanks Christy- I have sent all my friends to your site for these yummy gems!!!!!
I’m off today so i think I’m doing a whole Christy Recipe day. And i may even MAKE dessert.
Gotcha covered, sis!
http://www.southernplate.com/2008/07/chocolate-pound-cake-with-fudge-glaze.html
This is the fudge icing that you boil, it is actually a form of fudge and you have to spread it quickly because it starts hardening up pretty quick. Remember those old fashioned cakes where the icing would break off in hunks? That is this icing!
And here…. is the peanut butter version of the same stuff. Oh my lord is it ever good. I like that chocolate icing just on a plain old yellow cake!
http://www.southernplate.com/2008/07/yellow-cake-with-old-fashioned-peanut.html
Okay now add Chocolate Cobbler to the list as well.
*sigh*……
LOL- yep added that one to my list while I was just perusing again……..UmmmmmmmThe list is getting longer…not being narrowed down….I may have to celebrate my birthday EVERY month this year since i can’t decide.
LOL
And now I’m REALLY hungry.
OMG what a great cake, made it last night. I only got one small piece as the daughter, her husband and the 3 grandboys eat it with ice cold milk. I did make one small change I added the cherry juice to the cake batter always done it that way. Something else I tried and like way too much, I put some home made carmel between the cake batter and the pineapple, just a light layer.
Thanks for the Memories (BH)
norm
you have must have been reading my mind down here. I was so wanting a Pineapple Upside down cake. You know this cake gets even better the longer you keep it. But at my house it does not last very long. Thanks so much for sharing. God bless and Happy Cooking
)
Just the way I make the pineapple upside down cake too!
I make a peach upside down cake in my iron skillet that is a favorite around here.
I am going to try that little accidental discovery of yours, covering before completely cool, though.
Those are somtimes the best ones. Plus some of the best cakes I made before are those that crack all up.
Thanks for the recipe.
Have a great day.
Pam
I absolutely love Pineapple Upside Down Cake, but have never made it because I thought it would be hard or I would need a special pan.
I will be add these ingrediants to my grocery list and baking a pineapple upside down cake for my family (1 husband/3 boys) this weekend.
Yummy! If I had all the ingredients this would already be in the oven. Unfortunately I don’t, and it’s snowing bad outside, plus I have a sick kid, so I can’t go get the stuff (me in my best pouty voice). As soon as all is well in my house again, I’m rushing to get the stuff to make this! This looks even better than the one my mom makes. Don’t tell her I said that
I don’t think I have ever had this cake before. I know, gasp! A southern girl like me who has never tried pineapple upside down cake. I am going to have to blow my diet and try this one soon. Thanks for the great receipes, Christy! They are all great!
You know this is a faithful recipe here.
Oh, Christy…one of my favorite cakes. I have got to get the stuff to make this this weekend. This is a family favorite here.
I do my cake the exact same way! Usually I’ll leave out the cherries unless we have them on hand. But I’ll usually take the leftover pineapples and chop them up (kinda like canned crushed pineapple) and add that into the cake batter, so there are little bites of pineapple throughout the cake. Mmmmmmm!
I’m sick as a dog and need some comfort food. This means a stop at the grocery store for the pineapple upside down cake ingredients! My 11 year daughter who is an aspiring baker will be delighted to make it! Lucky me and thank you, Christy -
Beth in PA
Hey neighbor! I just had to click the link in your email, to see if you made yours like I make mine. Yup, you sure do! Except I use butter flavor cake mix, real unsalted butter instead of margarine, and I don’t ever use cherries. My husband’s grandmother taught me how to make this cake. I make mine in a rectangle Pyrex dish. I don’t turn mine out or cover my cake with plastic wrap. My Pyrex dishes have lids, so I let the pan cool enough to keep the lid from melting, then I cover the dish.
I have the stuff at home to make one. I’ll have to do that Friday, my first day off of work this week. Thanks for the idea!
Well Christy, Please don’t think of yourself as getting older.
Your just getting better girl. You know what they say about fine wine, well you just pour your self a glass, enjoy your day, as bask in the glow of hubby and kids treating you like a queen.
Happy Birthday, and may it be a wonderful day….
Wow! Looks sooooo good. I have some pineapple chunks at home, I think it would work with those just as well as rings.
I actually made upside down cake with your peach preserve recipe. I didn’t watch the peaches close enough and they got too caramelized to eat as preserve so I made it into upside down cake and it was so good and STICKY! Yum!
oh man… my knees are knocking! This looks amazing!
Thankyou for sharing this… can’t wait to try this for my honey!
I just made the butterfinger cake tonight. Now I gotta give most of it away cause I can’t eat it lol.
Hey Christy,
Your cake brought memories to my mind about my mom’s own pineapple upside down cake. Only she doesn’t use the cake mix for hers. I guess I’ll have to ask her for the recipe one of these days. Thanks for sharing this one with us! It does look yummy!
Happy Birthday Christy, this is just like I have always made my pineapple upside down cake too, but will add the little trick of steaming it to see what that does… and pecans always make everything just a little better if you have them, hahahaha
hugs from Oklahoma
Jo the grandma from Sapulpa
My husband just made me a pineapple upside down cake tonight — and my birthday is coming up too! Mine is Friday the 6th. That’s why February is the best month!
Except for this really cold weather we are having
Oh.My.Word.This.Cake.Is.Too.Good.For.Words!
You make your JUST like mine except…that I myself made a mistake once and bought crushed pineapple instead of sliced once and I thought it made the cake even better!!! The crushed pineapple gets really chewy and carmelized and just makes the cake even that much better. Yummy in MY tummy!!! LOL
My daughter and I are looking for recipes to cook something sweet every week and this recipe has made it to the top of the list for this weekend. We will let you know how it comes out. Sounds delicious.
Donna
Marine Mom
I helped my sons make this for a Cub Scout banquet tonight. The boys, with a parent’s help, were to make cakes/desserts to be auctioned off. The night ended with this cake taking the highest bid of all the cakes – and was talked about during one of the speeches! It was so easy to make and my boys (7&9)have now proclaimed themselves bakers. Thanks so much for a great recipe!
Hugs,
Jamie
Hey – I made this a few weeks ago – it was great – I most always use fresh pineapple for my cakes so I then used my pineapple orange breakfast juice as part of the liquid….it was the best Pineapple Upside Down Cake – I will make this again over my homemade batter version! I check your website every day for supper ideas – Thanks for all the good recipes!
I’ve been trying to think what I keep on hand that could take the place of the cherries, which I never have. Maybe raisins and then it would look like sunflowers. I’ll have to try that.
Yum!!! I mostly make it like you (with the juices and stuff), BUT I had no idea I could “cover it” to make it even moister. Yum, yum! What a funny, but yummy tip!
I’m new to this site, think I saw it on Southern Savers. And I love it!! You have such a terrific personality and your posts are not only fantastic, but hilarious! Girl, you have got to take your show on the road (if you haven’t already!)
I’ve got a list going of all the recipes I want to try of yours…and this one is going on the top!
Thanks for the terrific Southern Recipes!! I’m a follower for life!!
Amy
We loved it! It turned out just like you said it would.
Hi again Christy! Just wanted to let you know I tried this cake a few weeks ago and my 5-year ( the one who was eating all the apple chips from the apple butter!) decided he wanted THIS cake for his luau-themed birthday party tomorrow! Now, if that’s not a compliment, I don’t know what is!
I’m really looking forward to trying more of your recipes. I’ve been referring so many people to your blog! …Especially after getting an email from you and seeing what a great friendly personality you really do have! 
. Thanks again for all your stories & recipes! 
For those wanting a slightly less sweet cake, I use a Bisquick recipe. It has a denser, almost pound cake-like density. Everyone’s always loved my cakes. I just personally like it better than using a box cake, allowing the sweetness to come from the fruits and the brown sugar rather than the cake itself. The recipe below makes one 8-9″ cake:
1 1/2 c BIsquick
1/2 c sugar
1 egg
1 tsp vanilla
2 tbs butter, softened
1/2 c pineapple juice
As you would any other pineapple upside-down cake recipe, melt butter, add brown sugar (I always use dark, but it seems a lot of people on here like light, so whichever), then the pineapple and cherries. Combine all the cake ingredients above in a bowl and mix on medium for about 3 minutes until it is very well mixed. Pour over the pineapple and bake for 25-35 mins at 350.
That should be it. I hope you’re willing to take the few extra steps to make a homemade (well, sort of, given the Bisquick
) cake! It’s worth it – trust me! 
Christy,
When I tried to turn out this wonderful cake, the topping stuck to the pan! Instead of the beautiful presentation, I had to scrape the topping off and try to evenly smear/ plop it on the cake. It still tasted great, but looked lousey. How can I make sure that doesn’t happen next time?
I love Southern Plate!