A retro recipe that’s here to stay: this Pineapple Upside Down Cake is AMAZING. So supremely moist and soft, with a caramelized pineapple and maraschino cherry topping, it’s perfect for get-togethers, BBQs, potlucks, and any occasion!
You guys – this cake!
I’ve been tinkering around with pineapple upside down cake recipes lately and I had yet to find one I liked. For some, the cake was a little too dry – others, there wasn’t enough pineapple flavor or general pizzazz. I even found one recipe on the internet using dried cranberries in place of the maraschino cherries which is a crime against humanity and threatens the welfare of the world. Yeah, they’re neon red and full of sugar, but maraschino cherries are essential for this cake!
But after some trial and error – and pawning the guinea pig cakes to my apartment complex’s front office – I have found The One. And like when you find your human soulmate, I found my cake soulmate and this is it.
The cake part of this phenomenal piece of heaven is so supremely moist, fluffy and soft with a hint of pineapple flavor. The topping/bottom of the cake is just perfect: gooey, caramelized brown sugary pineapple slices and juicy cherries. The only thing that may be missing from this cake is a heaping scoop of vanilla ice cream. Just sayin’.
Whatever you do, promise me you’ll make this cake and love me forever?
The BEST Pineapple Upside Down Cake
Ingredients
- FOR THE TOPPING:
- 1/4 cup salted butter melted
- 1/2 cup brown sugar
- 5-7 pineapple rings drained and juice reserved
- Maraschino cherries without stems
- FOR THE CAKE:
- 3 Tbsp vegetable oil
- 3/4 cup granulated sugar
- 1 large egg
- 1/2 tsp salt
- 2 tsp baking powder
- 1 tsp vanilla extract
- 1⅓ cups all-purpose flour
- 1/4 cup full-fat sour cream or Greek yogurt
- 1/2 cup milk
- 1/4 cup pineapple juice
Instructions
- Preheat your oven to 350 degrees F. Lightly grease the bottom and sides of a 9" round cake pan with cooking spray. In a small bowl, combine the melted butter and brown sugar and pour the mixture into the bottom of the cake pan, spreading it out evenly. Arrange the pineapple rings around the pan and place maraschino cherries in between. Set aside briefly.
- In the bowl of a stand mixer, cream together the oil and granulated sugar until moistened. Beat in the egg, salt, baking powder, and vanilla until combined. Beat in the sour cream. Gradually add some of the milk, alternating with the flour until a soft batter comes together. Gently beat in the pineapple juice last.
- Carefully pour the batter over the pineapples in the pan, careful not to disturb their placement. Bake for approx. 40-45 minutes or until the cake appears set, is light golden brown, and a toothpick inserted near the center comes out clean or with moist, not wet, crumbs. Cool for 10-15 minutes, then very carefully invert the cake onto a platter or plate. Serve warm or room temperature.
I made this cake a couple weeks ago and I have had an actual dream about it since then – it’s that good.
Have a super sweet day!
xo, Hayley
cakespy says
It’s a classic for a reason: it has that iconic look and inimitable flavor! Looks like a fine specimen indeed, my friend.
Sean Mahan says
You sure know how to sell a cake! I got curious to try it even before actually reading the recipe!! My weekend just got a new goal: to make this cake!
thedomesticrebel says
Sean, this cake was so amazing! I have made it twice since posting this recipe because it is my new favorite!
Debby says
Hey what do you think about adding coffee flavor to the cake?
thedomesticrebel says
Hi Debby, I personally don’t care for the idea of pineapple and coffee together, but you could try adding instant espresso to it if you’re feeling adventurous!
Gab Watson says
This cake looks amazing! I want to make it this weekend for fourth of July! My question is this: what kind of milk should I use? We have unsweetened vanilla almond milk, will this work? Or should I get other milk? Thanks!!
Johnnyangel says
try it with a little bit of coconut oil in place of some of the melted butter
Joyce says
I made this cake in my cast iron skillet this weekend and it was DELISH! Fairly simple to make as well. I will definitely be making another again very soon.
thedomesticrebel says
Love the idea of making this in a cast iron! Thanks, Joyce! Glad you loved the cake 🙂
Gloria says
Made this today in cake pan. Came out beautifully. I wasn’t sure it would do without my iron skillet which I no longer have. . Will be making again. A long favorite in our family. Thank you for the recipe.
Stela says
Have you ever tried doubling the cake? I need enough for about 20 people. Probably best to make two cakes but thought I’d ask.
thedomesticrebel says
Hi Stela, I would make two separate cakes!
Juliette says
Thank you for sharing your recipe with us, I made it today it’s cooling now my husband and i will be having it for dessert! Will update on taste later.
Juliette says
This cake was awesome, delicious,and moist!
Juliette says
This cake was moist and delicious!
Daisy says
Omg sooo yummy , moist and my family loved it
Thank you !!
Stacy Janelle says
Can you make this cake in a 13×9 inch pan?
thedomesticrebel says
Yes! You’ll need more pineapple and cherries, however, and the cake may be thinner.
Ashley Whitehead says
Thanks for the amazing recipe! This was my first attempt at a pineapple upside down cake and your recipe helped me knock it out of the park! Very moist, excellent flavor on the crust, and the flavor was not overbearing. I’m making it again asap!
thedomesticrebel says
So glad to hear that, Ashley!
Erick Vernotico says
Is there a reason I couldn’t just double? A 9” round is much smaller than a 9×13” actually it’s just about double. If I stayed with the above measurements the cake would be very thin.
Amber says
Agreed. I’m going to double the recipe.
Alaa' Obeidat says
I tried this recipe and ot was to sweet for me suggest to decrease the amount of sugar to half for people who don’t like sweet ,the cake batter is amazing
Bianca says
Made this for my mom who is a pineapple upside down lover. It was the “best pineapple upside down cake” she’s ever had. I also loved it and will never use another recipe again. Thank you!
thedomesticrebel says
Bianca, I am so glad you and your mom loved it! Thank you!
Zaida says
Hayley! This cake is so delicious! My husband has been begging me for a pineapple upside down cake for years. My last attempt with another recipe wasn’t so great. But, this! It’s moist, dense, yet light and the batter smelled amazing. I think i will add a little rum extract to the butter/sugar mixture next time!
Tracey says
The recipe is amazing!!! I have made it several times! I love it!! Thanks for sharing it!
Jolynne says
Cake is in the oven as I type! Made it for my husband’s birthday. It’s his faforite…hope he loves it!!
Eman says
Yes, the best! Notvdry atvall. I made it in a larger oval pan becuase i needed to use up some fresh pineapple and so I wanted to have a large surface area for the pineapple. Diced the fresh pineapple and followedvthe recipe and it is perfect. The oil in the cake keeps the cake part moist, while the butter in the bottom gives it the right flavor. I hate butter cakes that get so dry the next day.
Thank you
thedomesticrebel says
Hi Eman, I am so glad you enjoyed! This sounds amazing with fresh pineapple!
Tonya says
This was my 1st time ever making this cake and not only was it super easy but this cake was very moist and super tasty!! Will make again for sure!
Marcelle Lowder says
Made this yesterday and it’s gone today. Very good cake, moist and delicious. Followed the recipe exactly and extremely pleased with the results.
thedomesticrebel says
Glad to hear you loved it, Marcelle!
Emma C says
Hello! I’m going to be making this most likely next week! Can you make it in a bundt pan or do you suggest a flat cake pan?
thedomesticrebel says
Hi Emma, I have not tried this in a Bundt pan, so I would probably stick to the flat cake pan!
Emma C says
Thank you!
Maria Sorrenti says
i am not sure i like the idea of oil in the cake. I made it and my cake was lop sided and flat on the top…what did i do wrong? Seems dense, is that the way it supposed to be? I will try it and hopefully the flavors are there.
thedomesticrebel says
Hi Maria, the oil definitely helps with moisture! It is kind of a flat cake. Hopefully you enjoy the flavor.
Leslie Kupfer says
Hi Hayley,
Baked this cake today and although it is still cooling, it is a beautiful sight to behold! I did use thoroughly drained crushed pineapple instead of rings, cut the cherries in half before placing them, and added coarsely chopped, toasted pecans (just because that is what my Grandmothers and Mom always did.) We are anxiously awaiting enjoying a piece of heavenly cake, thanks to you and your endeavors to create a perfect Pineapple Upside Down Cake!
Drema says
Going to make this cake today for a church bible study group. I’m using an iron skillet. A#8 size . Do I need to double the cake recipe?
SJ Spear says
Oh yes, yes, yes! You’ve nailed it with this recipe. I made this cake this week for my DIL’s Birthday. Pineapple upside down cake is her favorite so this was a high stake baking venture for me! I made it as directed (chose full fat sour cream) and it was perfect. A five star rating for sure!
Tiffany says
Have you ever tried making these in cupcake tins? If so, do you know how long they bake for?
thedomesticrebel says
Hi Tiffany! I have not but I’m sure it’ll work! Just maybe bake for 15 minutes or so, checking at the 15 min mark and increasing by one minute increments if not done.
Mary says
When I made individual pineapple upside down cakes, I used the larger muffin tins because the pineapple rings were too big for regular cupcake tins and the cakes come out a nice size. They came out great and were a huge hit for a birthday luncheon I had for a group of lady friends.
Heather says
Delicious! For those curious, I used a Bundt pan and it turned out excellent! I did, however, make a little extra brown sugar / butter mixture, and used a can of “pineapple tidbits” instead of rings as that’s what we had on hand! Oh, and added a touch of cinnamon! Yum!
Heather says
I’m not sure what went wrong in this recipe, I am an avid baker, followed this recipe to a T, and it went horribly. The top of the cake before you flip it almost burnt and bubbles in the middle and still wasn’t done.
thedomesticrebel says
Hi Heather, it sounds like your oven runs very hot. Next time, you can tent the top of the cake with foil to prevent it from browning too quickly!
3mountaingirl says
I had to scroll thru a bagillion comments where zero people had a problem before finally finding this one that matched my own. I have two round aluminum wilson cake pans and one lone steel round cake pan and used that for this recipe and I swear it looked so very done, to the point I was hovering around the oven for the last 5 minutes afraid it was going to burn for how brown it was on top. I resisted the urge to pull it early, and when the timer went off I pulled the beautiful looking cake out, stabbed it with a toothpick, and the toothpick came out 100% clean….figured that was perfect but maybe that was a sign a less novice baker would have read as not ready? My cake was done around the edges and not done inside, heartbreaking. To anyone reading this, please read the gagillion, near 100% five star reviews that mention how fool proof this recipe is. My failure was exactly that, mine, and I suspect a product of either the steel pan or my oven’s heat. Just bummed bc it was a “pandemic” bake but looking forward to my redemption, next time will cover this with foil, use my wilson cake pans, and maybe even cut away part of the top to inspect as its going to end up on the bottom anyway.
thedomesticrebel says
Hi 3mountaingirl, was your steel pan dark by chance? If so, that would explain why the edges are done but the middle may be underbaked. Dark metal conducts heat super quickly, resulting in super browned bottoms and edges but not quite done centers. I recommend light metal baking pans for this.
Bieke says
Hello!
I’m trying the recipe next week. Do I have to use fresh pineapple or canned
Greetings from Belgium!
Bieke says
Hello!
I’m trying the recipe next week. Do I have to use fresh pineapple or canned
Greetings from Belgium!
thedomesticrebel says
Canned!
Amy Rankin says
My youngest son requested pineapple upside down cake for his birthday. I had never made one and decided to give this recipe a try. It was delicious! The consistency of the cake was wonderful! Everyone loved it!
Faith says
I would like to make this for a group of about 100 . I am thinking multiple 13×9…. any suggestions before I move forward. Thanks
thedomesticrebel says
Hi Faith, yes, I would definitely do multiples of a 9×13 pan. It may be easier to use pineapple tidbits and chop your maraschino cherries to spread over instead of using pineapple rings.
Rachael Walton says
How does this keep? I’m making it for an event and would like to make it the night before… would I refrigerate it and then take it out and let it warm to room temp before serving? Thought? 🙂
thedomesticrebel says
Hi Rachael, it keeps well! I would do exactly what you stated – refrigerate airtight and come to room temperature, or you could definitely leave it out but covered.
Margie says
Hi! Can I use cake flour instead of regular flour or will this mess up the recipe?
thedomesticrebel says
Hi Margie, I would stick to all-purpose flour.
Gigi says
I just made it for hubbies birthday. Can’t wait to taste it 😋
Gigi says
This cake was so delicious and very moist 😋, hubby loved it as well! Will be making this one again.
Robyn U says
Hello! This looks awesome and I can’t wait to try it! 2 questions: first, could I use fresh pineapple if I made them tidbit size? And secondly, I noticed you didn’t mix all your dry ingredients together…
It got really good reviews so I’m excited!
Thanks,
Robyn
thedomesticrebel says
Hi Robyn! Yes, I do not require the dry ingredients be mixed together before adding to the moist ingredients, but you can if you’d like! As far as the pineapple goes, I do not see why you couldn’t use fresh pineapple! I think it’d be delicious! Just remember you do need some pineapple juice for the cake batter.
Susan says
I made this cake for family during the Coronavirus quarantine. I did not have the traditional can of pineapple rings but did have a 8 oz can of crushed pineapple that I used. It was a big hit. Everyone thought it was delicious and gave everyone more pineapple. The only criticism was it needed more cherries.
thedomesticrebel says
Hi Susan, yay, I am so glad your family enjoyed the cake with crushed pineapple! I like mine with extra cherries, too 🙂
Debi says
Made this today and love it.
Brenda Formsma says
This was absolutely delicious! I’ve been baking a lot during the Stay at Home order and had a can of pineapple in the cupboard so thought I would give it a try. No cherries but used a few blackberries. My husband and I devoured half of it for dessert tonight. So yummy!
thedomesticrebel says
Brenda, I LOVE the idea of using blackberries! Thanks so much and glad you enjoyed!
Norma Vieira says
I have just read through this recipe and know how delicious it is going to be for Sunday’s Easter dinner. Sometimes, one just knows. My kids and I will love it! However, my husband is vegan so I will also be baking a vegan carrot cake. Do you have any suggestions to make this cake vegan? I usually use flax meal for egg substitutes but everything I bake usually ends up having a weird texture.
thedomesticrebel says
Hi Norma! Hm, I don’t have a ton of experience baking things vegan so I can’t say for sure. The flax egg would have been my recommendation.
Candi says
Made this tonight…Absolutely delicious!! Hubby raved about it. Went by recipe except used crushed pineapple. Will definitely make again.
thedomesticrebel says
Hi Candi, I am so glad you and your hubby loved it! Happy Easter!
Sherry Jones says
This was great !!
Marnie Marfil says
This was so easy and tasted ammmmmazing !!
Lysa B. says
Hello, this does sound great. I have yet to have time to try a homemade one. I usually make the Pineapple Supreme one by Duncan Hines and add pineapple juice as well as a box of instant vanilla pudding. Always works and my cake is a hit and requested often. But, I have some time now with the stay at home order. So want to try something different. BUT, I do all of mine in a 9x 13 pan. I saw a question about the 9×13 pan. Does anyone know id you double the recipe if that works? Hate to waste ingredients at this time of need and that not be the answer. Baking supplies in my area are very sparse right now but may just give it a try but thought I would ask just in case anyone tried and knew.
Thanks some much and stay safe and healthy everyone!!!
thedomesticrebel says
Hi Lysa! I would just double all of the ingredients to make this in a 9×13 pan! As written now, it would be wayyyy too thin in a 9×13 so you’d want to double all the ingredients for sure. Check it for doneness around the 20-25 minute mark.
E Tahir says
This recipe is super easy and the cake super moist and delicious ….definitely a keeper….I used fat free sour cream and it was fine.
Mandy says
Hi there! I plan on making this cake on tomorrow night. Does it need to be refrigerated? I have very little space in the fridge and am hoping to leave it covered on the counter.
thedomesticrebel says
Hi Mandy! It can absolutely be left on the counter. Just keep it covered to ensure it stays moist and doesn’t dry out.
Charlene Rolland says
OMG thank you..this cake is Delicious! I double the recipe and came out beautifully from a 9 x 13 inch pan.
Ana says
Hello everyone. I’m from Panama and it’s my firts time doing pineapple upside down cake. It taste so good and was so easy to do it. It looks beautiful too. I’m so happy. Tks for the recipe I really like it.
Andrea says
Hello, I want to make this cake for my husband’s 50th birthday (Hawaii Five-0 theme). Has anyone done this as a bundt? If so, does it need to be modified and/or doubled? Thanks!
thedomesticrebel says
Hi Andrea, good idea! Since this doesn’t yield a lot of batter, I would double the cake batter recipe. Maybe use pineapple tidbits and cherries along the bottom of the Bundt pan, then pour batter on top. Just grease really well!
Eleanor says
Hello, I’d like to add either Hennessy Cognac or some rum to this recipe. How do you suggest I do that – as a substitute for a particular ingredient or just added at a certain time. I’m assuming about a 1/2 cup of either. Your thoughts on this would be much appreciated!
thedomesticrebel says
Hi Elanor! You could use it in place of the pineapple juice, but then the cake wouldn’t be super pineapple-y.
Seli says
I accidentally doubled the sour cream so I halved the milk x( hopefully it comes out okay!!
Katz says
My Husband’s Mom has been making him Pineapple Upside Down Cake for years. Her recipe is very good! However, he was very impressed with this recipe! He wants to have it again and that is saying something amazing about this recipe, thank you!
Liza says
This is my go-to recipe now and it’s a hit with everyone who is lucky enough to get some.
I would like to make a gluten free version and wonder if you have any recommendations.
Thanks
Grace L Smith says
You need look no further!!! This is it…the best, I went exactly by the recipe although I did mix the flour with the salt and baking powder beforehand. I made it my cast iron skillet and it was PERFECTION. Now, I’ve had my own cake business back in the day, but always try new things, this is perfect. It baked up nice and golden brown. A true KEEPER!!! Yes, I love you forever now!
Thilini says
Hello from Australia! Could I substitute glacé cherries for the maraschino cherries (which are not readily available here unfortunately)? Or would you recommend using a tin of black cherries In syrup as the substitute? We also have frozen cherries so that might work as well? Thank you in advance!
thedomesticrebel says
Hi Thilini! Whatever sweetened, pitted cherry you have will work! I believe glace cherries are very similar if not the same as maraschino cherries!
Liz says
Hi, there!
I just put this cake into the oven and am wondering if the batter is supposed to be pretty loose or if my scale is on the fritz????? You’re pictures are AMAZING!!!
thedomesticrebel says
Batter should be somewhat loose! I am sure it’ll be fine!
Lindsay Phillips says
I’m looking forward to making this cake for my boyfriend’s birthday! Pineapple Upside Down is his favorite, and this is the first time I’m baking something for him! My question is, I dont have a stand mixer, just a hand held at the moment. Any suggestion to make sure I don’t over mix or any general tips?
thedomesticrebel says
Hi Lindsay! A good rule of thumb is to just barely combine the cake ingredients. You shouldn’t see any more streaks of flour in the batter, but don’t go overboard in mixing everything in, either. It can lead to a tough cake! A hand mixer will be just fine. Sometimes to ensure I don’t go overboard on accident, I’ll mix the flour and dry ingredients in by hand. Hope this helps, and Happy Birthday to your boyfriend!
Shirley says
I’m love to bake and on weekends when I’m free from taking care of my grandchildren, I would look for a recipe to bake. I was craving for a pineapple upside down cake so went ahead and search for a recipe. Found your recipe and it’s amazingly good. Love the moist but dense texture of the cake. I used crushed pineapple since that’s what I have in my pantry. Next time I’ll make it with sliced pineapple and cherries.
Debbie says
I haven’t made a pineapple upside down cake for years and was pleased to find this recipe! It turned out wonderful! The cake was moist and the pineapple topping was tasty!
Bee says
This looks UH-MAZING! I am definitely going to try it next week. If I wanted to use this for just a regular cake, would I sub the pineapple juice for milk?
Thanks!
Bee says
Also, can I use coconut oil for this cake?
thedomesticrebel says
Hi Bee, I believe it would be just fine to use coconut oil in place of the vegetable oil.
thedomesticrebel says
Hi Bee, yes, you could use milk!
Mary says
Your recipe sounds perfect! However, my dilemma… I have a 8 1/2” cake pan & I fear spillage because it is too small (I’ve read that is a common occurrence) can I use a glass pie pan? I fear that the bottom “topping” will not brown &carmelize effectively with glass. I am a seasoned baker… but haven’t been interested in making a pineapple up/down cake, but my husband has been wanting one… your recipe stands out from others.
thedomesticrebel says
Hi Mary, you’re right, the glass won’t have it caramelize as much but it will still work. Just maybe increase the baking time longer due to the glass not conducting heat as evenly as a metal baking pan. An additional 3-5 minutes or so should work.
Ann says
I’m excited to try this recipe! I’d like to use this cake to make a layered sheet cake with whipped cream. Do you think it’ll hold up? Will it still be moist after refrigeration? It’ll probably need to be refrigerated because of the whipped cream.
thedomesticrebel says
Hi Ann, yes, I would double the recipe for a sheet cake though. And if there is whipped cream, I would refrigerate.
Amy says
I have a 9 inch springform pan will that work or will it be too big?
Amy says
I am think big as far as too tall…..
thedomesticrebel says
I think that will work!
Tobi Sandoval says
I don’t know where I went wrong but this cake came out incredibly dense and tough. I think, perhaps, I may have over mixed the batter by a LOT. Still, recipe gets 4 stars because that was user error and it still tasted delicious. I’m going to try again in the future. Next time I’ll mix by hand.
Becky says
Delicious cake. Almost as good as my Mom’s. Thank you!
Gabby says
Hi! I am thinking about making this for the weekend! I was wondering what type of milk to use? We have unsweetened vanilla almond milk right now…would this work? Looks delicious!!! I hope my cake turns out like this !
thedomesticrebel says
Hi Gabby, almond milk should work! Otherwise I would recommend cow’s milk – whole or 2% is best, but 1% would work.
Gab Watson says
Thank you so much for the quick reply! I am so excited to try it out…and even more excited to eat it!!
Melissa says
This was DELISH! I added 2 tsp of cinnamon and used an 8×8 square glass pan. Will definitely make again.