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pineapple upside-down cake

I gotta tell you–I get so boring in the summertime. As soon as that warm weather hits and a bright blue sky becomes de rigeur and not something worth stopping the presses over, any near-religious attraction I had to the shiny and the new goes into hibernation until the fall. Do I want to start a sourdough that will take seven days to make? Well, since you asked, not really. How about that baked pasta dish that been buzzing like a bee in my bonnet for weeks? Um, well, maybe. If it rains or something and there’s nothing else to do. Do I want to try some new, crazy variant on a classic cake with cardamom? No, no, no!

pineapple tire

Well, then what do I want to do? I want to go to the beach, and I want to go to barbeques. I’ve got goals, you see: I want to perfect the mint julep this summer and uncover a way to travel with all the trappings of a freshly squeezed Tom Collins. I want to bring buckets of just-made slaw, make more of my famous vegetable skewers that could fit on eight grills and I want to arrive with the kind of cake you don’t have to make a big deal out of; no frosting, no filling, no baubles, jimmies or piping and a minimal number of bowls. The kind of cake you’ve been eating your whole life yet a bite of it in the off-season will bring you back to a lazy spring weekend and a pinata filled with airline bottles of Petron.

If you’ve stopped eating pineapple-upside down cake because you were rightly scared off by the seventies wallpaper-like pattern of rubbery pineapple rings filled with unnaturally bright maraschino cherries and the bland, almost pointless cake within that are all-too-accepted as the bakery standard, fear not, you can start again. Just two things separate a great pineapple upside down cake from a cake with, uh, pineapples on top are two things, three if you include the absence of red fruit-like gems: fresh pineapple and a layer of freshly-made caramel.

pineapple upsided

Don’t be put off by the caramel; if you have a 10-inch cast iron pan, you can make it right in the bottom, and use that as your baking dish. If not, it’s only one extra dish and takes less than five minutes to make. Fresh pineapple is the real turning point, though, and I was deeply saddened to not be able to find any this weekend (that is, until after I made the cake, naturally). It’s sharp, tropical flavor is unmatched by canned version, but in a jam, the can is your friend as it also comes packaged with the pineapple juice required for the cake.

And that’s all the fancy there is to this. You can make and bake in about an hour and a half, tops, and be that much more welcome anywhere you go. I know I was.

packed and ready

livestrongThis cake is my contribution to Barbara Harris’ of WinosandFoodies.com A Taste of Yellow Event, in which food bloggers from all over the globe create a yellow food to show support for Lance Armstrong’s LIVESTRONG Day, May 16. The event is grassroots advocacy initiative to unify people affected by cancer and to raise awareness about cancer survivorship issues on a national level and in local communities across the country. You can make a donation to the Lance Armstrong Foundation over here.

Pineapple Upside-Down Cake
Adapted from Gourmet, February 2000

The original recipe for this cake had three teaspoons of cardamom in it, alternately loved and loathed by recipe reviewers. Having no interest in a chai-flavored cake — or chai-flavored anything, ever –I took it out and was left with the most flawless and easy go-to upside down cake, something I look forward to making every summer.

Topping:
1/2 medium pineapple, peeled, quartered lengthwise, and cored
6 tablespoons (85 grams) unsalted butter
3/4 cup (145 grams) packed light brown sugar

Batter:
1 1/2 cups (190 grams) all-purpose flour
2 teaspoons baking powder
1/4 teaspoon salt
6 tablespoons (85 grams) unsalted butter, softened
1 cup (200 grams) granulated sugar
2 large eggs
1 teaspoon vanilla
1 tablespoon (15 ml) dark rum
1/2 cup (120 ml) unsweetened pineapple juice
2 tablespoons (30 ml) dark rum for sprinkling over cake

Special equipment: A well-seasoned 10-inch cast-iron skillet. If you lack a cast-iron skillet of this size, make the caramel in a small pot and scrape it into the bottom of a similarly-sized cake pan. (I used a 9″ cake pan in the pictures above.)

Preheat oven to 350°F (175°C).

Make topping: Cut pineapple crosswise into 3/8-inch-thick pieces. Melt butter in skillet. Add brown sugar and simmer over moderate heat, stirring, four minutes. Remove from heat. Arrange pineapple on top of sugar mixture in concentric circles, overlapping pieces slightly.

Make batter: Sift together flour, baking powder, and salt. Beat butter in a large bowl with an electric mixer until light and fluffy, then gradually beat in granulated sugar. Add eggs, one at a time, beating well after each addition. Beat in vanilla and rum. Add half of flour mixture and beat on low speed just until blended. Beat in pineapple juice, then add remaining flour mixture, beating just until blended. (Batter may appear slightly curdled.)

Spoon batter over pineapple topping and spread evenly. Bake cake in middle of oven until golden and a tester comes out clean, about 45 minutes. Let cake stand in skillet five minutes. Invert a plate over skillet and invert cake onto plate (keeping plate and skillet firmly pressed together). Replace any pineapple stuck to bottom of skillet. Sprinkle rum over cake and cool on plate on a rack.

Serve cake just warm or at room temperature.

Do ahead: Cake may be made one day ahead and chilled, covered. Bring to room temperature before serving.

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211 comments on pineapple upside-down cake

  1. My empanada’s were stolen. My heart is completely broken. All I want is an empanada. I am so depressed. Please make more, I promise not to lose them this time.

    Oh, and BTW, that cake was tasty! Yum.

  2. Ooops, premature posting. But, I would love to try it one day. Though, baked pineapple and cake, I don’t know how I’d do with that kind of combo. It’s all about the texture. Is the cake overly wet or just the right amount of softness? Also, is the pineapple really sticky in your mouth with the caramel?

  3. mmmmmm. I LOVE that you wrote about Pineapple Upside Down Cake. This has been a favorite of mine since i was little and so many people are all “Pineapple WHAT cake? Never heard of it.” My recipe is a little different, but probably a mixture of the ‘boring’ and this, which sounds wonderful and i WILL have to try sometime!

  4. Mary — The cake carrier I use is actually a 10″ Kaiser springform pan, but when you pop the side off, you can use it to carry more than cheesecake. I wouldn’t call it the most rugged of carriers (I don’t trust the handle and instead drop the whole thing in a bag), but certainly more pretty than others that I’ve seen.

    Joc — It’s not my fault you let Tim make you cocktails and proceeded to forget the empanadas. Sounds like the early birds got the egg. ;) Speaking of, when Alex and I left at 9, it was still a fairly civilized affair. Then RGD came over last night having not been home yet from the day before. You people make me feel old.

    Jenifer — I don’t think it’s really sticky. The caramel sinks in a bit, because it’s baked right into the cake. It just adds extra flavor and an ever-so-slight crunch to the top. You just know I’m dying to make the caramel next time with salted butter, btw. I’ll let you all know if I do.

  5. I think we must have an ESP(N) thing going on. I’ve been wanting to make a pineapple upside down cake for a few weeks now, and here you are with a recipe for exactly that! Thank goodness the boyfriend isn’t allergic to pineapple.

  6. I made this once over the winter with gingerbread spices and I concur, it’s delish, would’ve never thought of it for summer, but the pineapple’s perfect. I think I sprinkled some extra sugar on top and bruleed it b/c I felt like the top wasn’t as pretty as I’d like.

  7. This looks very similar to Ina’s plum cake she made for me the other day (me and millions of other viewers). I’m guessing it’s basically the same, just a different fruit and different liquor. Yumm.

  8. Yes! In fact, I’ve always wanted to make Ina’s plum cake but 1) Alex is wrongly put off by plums in desserts (he won’t be after this summer, I promise) and2) I remember reading a blog where someone hadn’t loved the recipe. I’ve long forgotten what it was. I think Ina also makes an apple version, but she calls it her “tarte tatin cake.” I’d like to try another version of this, however, and I’m thinking of either playing around with mangoes, strawberries or even pears.

    Merecedes — Gingerbread spices, I’ve never heard of that! Perhaps the caramom addition isn’t as off-base as I’d thought.

    Brandon — Ha! I can’t even lift my own. And the 7.5 qt. Dutch oven counts as my bicep curls any day I wash it.

  9. Looks gorgeous! I just love pineapple upside-down cake… yum! Oh, and if you are serious about perfecting your mint julep this summer, here’s an idea for you: I had the most delicious mint julep of my life recently at a nearby restaurant, and it was so absolutely simple. They filled a glass with a few scoops of a homemade mint sorbet, then poured a couple shots of classic Kentucky Rebel Yell Whiskey on top! The sorbet melted into a cloudy and fragrant alcoholic pool of deliciousness that I simply cannot give justice to with words. Give it a try! I just need to find a really good mint sorbet recipe now…

  10. Pineapple upside-down cake should be in everyone’s repertoire. I have a friend who requests it regularly but refers to it as “bend-over cake” (English is not her first language). I love your recipe, particularly the rum — and I love the idea of using salted butter. I sometimes make it with browned butter, and with freshly-grated nutmeg — more subtle than cardamom, and perfect with pineapple, I think.

  11. something very strange happened…i swear i had left a comment earlier…seems to have vanished ! well this is a beautiful entry for a taste of yellow, although i’m not a big fan of pineapples and specially upsidedowns i like your twist with the caramel and omitting those scary n gaudy cherries. this one has got me rethinking my choices.

  12. Nor, this sounds truly wonderful, but being a simple, benighted European I have to ask: how much is 3/4 of a stick of butter? How much butter is there in a stick, anyway? I’d love to know the weight – I’ve spent too much time pressing butter into a measuring cup and getting it out again to be really happy with cup measurements…. Apart from that, the cake looks and sound great, and I’d love to try it!

  13. great Taste of Yellow cake! and i’ll just have to take your word on the caramel… its a daunting task in a small apartment kitchen with a microstove

  14. Mangoes would be delish. I wonder what liquor would go well with that ? Maybe rum again. Pears and brandy would be a good combo. Obviously I don’t cook/bake, I just like to find good alcohol pairings for you. :)

  15. Ok Deb I think I’m channeling you. I made a pineapple upside down cake this weekend! I used the Joy of Cooking recipe (pecans – no red cherry things). It was delicious but yours looks like I have to try it. Another cake is in my future!!!

  16. The thought of that tart pineapple up against the sweet caramel just made me drool a little bit before I caught it. Must go in the recipe queue.

  17. I’m such a ham for this cake (ha ha.)
    I saw these cute leetle tiny pineapple upside-down (indiv.) cake pans at Sur La Table the other day.

    The strange thing is, no matter how old I grow, this cake always makes me smile and think of Amelia Bedilia.

    See you in Coney Island in June?

  18. This looks great! Since you owned up to using canned pineapple, how much did you use? Yeah, I know fresh is better. But so is being lazy sometimes.

  19. No comment on the post…well, I do like pineapple upside down cake and probably haven’t had it in….oh, at least a few years, if not more – so I suppose I am due for some soon….but really have to say that Alex not thinking plums in desserts are any good is pure craziness!!! I have this great plum pudding cake that my fiance’s mom has passed to us and in August when the plums are plentiful here, I will risk the discomfort of raising the house temperature yet another few degrees just to bake it! I can scrounge up the recipe if you like, but it sounds like you have plans for plums in baked goods already!

  20. I just made this for my boyfriend’s birthday… and it was DELICIOUS. I hardly ever make cakes, but this was a huge hit. I didn’t have dark rum, so I used spiced rum…. it came out great. I already have requests for a repeat performance.

  21. Mmm.. Made this last night and between the boyfriend and I it is nearly gone.

    I added coconut extract, coconut shavings and extra vanilla to the batter. Plus, thought about adding a bit of coconut milk to make a Pina Colada type deal.

    Thanks for the great recipe!

  22. I made this cake last week since it was finals week for my classmates. The first time I made it I found it to be TOO sweet. So I cut the sugar in half and used a 1/2 cup of pineapple juice concentrate. The cake was great – it was almost juicy – the pineapple flavor quite pronounced. I highly recommend the change.

  23. Excellent recipe! I’m thinking it’s one of the best I’ve come across…..ever. The pineapple juice in the batter make it a number of steps past fantastic.

  24. Do not do not do not use a springform. Trust your instincts and ignore comments on epicurious that say a springform works. I wish I had. I lost all the caramel and my oven is a disaster and I want to cry.

  25. I JUST pulled this out of my oven. And I can’t tell you how excited I am about it!

    This was one of those ‘go to’ recipes my mom always made when I was growing up. She felt that dinner wasn’t complete without some sort of dessert on hand.

    I had a hankering, and used your little search feature. (I can’t tell you how many times you’ve had exactly what I was looking for!)

    One little tidbit to add as to why this is so exciting. I didn’t have a 9″ round cake pan, and though I know it would work in a rectangular one.. I wanted round!

    What I did have, was a clay bowl that Ive been too scared to use.

    I used it. It came out great!
    Thanks for helping conquer my own cooking fear!

    MK

  26. I made this yesterday for a BBQ. I doubled the recipe, used fresh pineapple, 9 inch rounds in a convection oven next to each other and also omitted the cardamom and I gotta say, you saved me again. I loved PUDC (pineapple upside down cake) as a kid, but knew that just wouldn’t fly with the adult me let alone my equally picky friends. it was a kabob and grilled pineapple bbq, so this was the perfect reason to try it out – and it was a hit! it was easy (I did it last minute after a day of canning pickles) and it was flawless. I cooked the caramel a smidge longer than suggested to get it a bit darker and found it to really work well for travel and have moist without the sog. thank you a million!

  27. Deb – hold on to your hat, because I am about to blow your mind. I made this cake for Thanksgiving…as a Cranberry Upside-Down Cake. Exactly this recipe, but anytime you see the word ‘pineapple,’ replace with ‘cranberry’ and replace all instances of ‘rum’ with ‘brandy.’ I used 100% cranberry juice in the batter and it turned a really beautiful shade of pink. The cake is gorgeous and it has kind of nice, sour pucker to it. I hope you’ll try it!

  28. The plum cake sounds good but my boyfriend won’t eat anything by Ina because the whole BAREFOOT Contessa thing creeps him out.

    I’m currently making this cake. However, my batter seemed kind of dry. I could be wrong because this is my first from scratch cake. I’ve only ever made boxed cake.

    Wish me luck!

  29. It was terrible!!! =( I think my oven is broken. The center was completely raw but the outside half was dense and overcooked like a brick. I’ve never made a cake in this apartment. I think I’m going to make a box cake to make sure it’s my oven and not just me.

  30. Dear Deb,
    I discovered your site about 3 weeks ago and have been reading it diligently every day since. The thing that really attracted me to your kitchen was not the mouthwatering photos but your writing, whose level of excellence makes your site truly stand out. One can find any number of great pictures on the net; a long, grammatically sound sentence, however, let alone subtle play word or self reliable humor that does not need the ubiquitous smiley face to indicate to the simple minded reader that this is the place to laugh, is a rarity on the Internet.
    You do not use language solely as a coarse tool for conveying information; you do not use language, you create with it: the atmosphere, the taste, the mood, the texture, the very soul of the cooking experience – all these things come not from your photos, but from your writing. Oh, I don’t underestimate the importance of a beautiful photo, but I belong to the school that dispenses with the truism that “a picture is worth a thousand words.” No, a picture is worthless without a thousand words to bring it alive, to make your experience ours, at least in the world of cooking.
    Thank you for making our experience complete.

    I did not realize the expression of my admiration would take up so much space. This is my first time participating in a site like this and I don’t know what the rules about posting are. Please forgive me if I am violating the posting etiquette. The real reason for this post was to relate my experience with the pine apple cake. I’ll start another one for it.

  31. Now for the cake, finally:

    This is my first experience with the upsidedown pineapple cake, both eating and baking it. I am not a novice baker however.

    Things that I had to change:
    Used dark brown sugar instead of light (that’s what I had in the cupboard)
    Used a 12” cast iron skillet (don’t have a smaller one)
    Used orange juice from a freshly squeezed orange (forgot to buy pineapple juice)
    Used fresh pineapple but one that had already been peeled and cored (sold in the fresh produce isle, along with other precut, cleaned, peeled, etc. fruit). While this is not as flavorful as the pineapple you peel and core yourself, it is infinitely better than the canned variety.

    Things that presented unexpected difficulty:
    The caramel: While I’d done tons of work with all sorts of sugar/water combinations, I’d never had a chance to make the butter caramel, nor had I used brown sugar for it before. First of all, I went about it the wrong way, I guess. Not having read you directions carefully, I put the butter and sugar in the skillet together (as I would with water based caramel). So the butter was melting along with the sugar. Since I was used to making water/white sugar caramel, I was using the same process: let dissolve on low heat, bring to the caramel consistency on high. Apparently this does not work with butter and brown sugar. Somehow everything took much less time than I had expected. (The additional difficulty, was that since it was brown sugar, I could not go by the color indication of the state of the caramel – it was dark from the start). So I realized that the caramel was ready when the smoke started rising from it quite heavily. I should have turned it off about two minutes earlier. As it was, it was almost burnt. But I decided that the sweetness of the pineapple will dilute the intensity of the caramel.

    The rest of the preparations went smoothly. (By the way, you mentioned that the batter might look curdled in the end. I think to avoid it, one should be very careful when adding the vanilla/rum to the butter/egg mixture. Add it almost drop by drop, mixing well after each addition, to prevent butter from separating. After that step, the batter should end up smooth and pretty. Also, I folded the last addition of the flour mixture with a spatula).

    Even though I had a large skillet, the batter filled it nicely.
    The baking time was about 47 minutes.

    The cake was a very beautiful color: amber/golden. I almost did not want turn it upside down.

    The cake came out very easily, surprisingly, with only one piece stuck.

    The caramel, as I suspected, was overcooked and patches between the pineapple looked nearly black. However, these pieces were a delicious excuse for picking off the cake while waiting for it to cool down.
    With a superhuman effort I resisted cutting it until this morning (It came out of the oven last night around midnight).

    Today I had a slice for breakfast: heavenly!!!!!!!!! I had no idea that this is what a pineapple cake tastes like. To be honest, I used to be suspicious of the whole idea: wouldn’t pineapple get soggy?, wouldn’t the tropical taste be too much with the rich batter?, etc.

    Well, after today, I am certainly a convert.

    I will make this cake again, but with some changes:

    Definitely less sugar in the batter next time. The caramel and the pineapple itself provide plenty of sweetness.

    I will sprinkle the rum on the hot cake while it is still in the skillet, before being turned out. I found that the rum did not penetrate the layer of the caramel and stayed mostly on top of the pineapple.

    I will leave the skillet size as is, however. The cake rose nicely, the overall height is about 1.5 inches, which is perfect for this very rich cake.

    Overall, very pleased with the experience; will repeat. Thank you so much!

  32. OMG! This was the BEST PUSD cake EVERRRRRRRRR!
    I made it for a funeral today. The fresh pineapple and seasoned cast iron skillet method def makes all the difference. I must admit, I was terrified to flip it onto the platter because once I did… I couldn’t really see the middle of the cake to tell if the center was REALLY done. But of course… it was perfect! My cake didn’t look as perfect as the pic, but close enough. I received so many requests for the recipe. I will make this again and again.

  33. I was looking for desserts and this was selected for me by the “Surprise Me” gadget. What a good choice it was too. It is just delicious. I used the fresh pineapple and also added the dreaded cardamom, but only a half tsp; barely noticeble. My only problem (and it was indeed my problem) was tipping it out of the pan. My plate was exactly the same diameter as the pan and it slipped as I turned it out. Half was on the counter and the other half on the plate. Grrrrr!
    Fortunately, it broke exactly in half so I was able to rescue it with my long metal spatula and glue it back together with the caramel and hide it under some well placed pieces of pineapple. Moral of the story? Mind the plate size!

  34. I found this site while looking for a pineapple upside-down cake recipe and I’m very glad I did. I made it tonight, and it was fantastic! I don’t bake very often, and still I had no trouble making this. I love how the caramel makes the outside chewy. I will make this again and share the under-appreciated dessert with friends and family. Thanks!

    Oh and your writing and photography are deliciously mouthwatering.

  35. I just clicked on this to see if it’s anything like the P.U. cake I always make. Well, it IS the one I always make. But I’ve made a few tweaks over the years, and I like it even better now.

    Sometimes I use coconut oil (the healthy kind) instead of butter in the cake part. Tastes really nice with the rum and pineapple. I also cut the amount of sugar in the cake by at least a third, and make a little less caramel. Pineapple is already so sweet, the cake hardly needs two cups of sugar on top of it.

    I think you should consider the cardamom. It doesn’t make your cake taste like chai at all. Far from it. I do 1.5 tsp of it. I think it’s what makes the recipe unique. People can’t usually pinpoin what it is, only that it’s got a special flavour.

  36. I made this cake last night (for the season finale of Lost!) — it was my first experience making or eating pineapple upside down cake, and it was excellent! I was a little worried, because the sides of the cake were getting a little blackened looking in the oven, but it turned out perfectly, though I would probably cook it about three minutes or so less. I used dark brown sugar, which made the caramel a little bitter, but it was delicious (and I tossed a little salt into the butter/sugar mixture, because I love salted caramel). Thanks for the recipe, Deb! I can’t wait to make it again.

  37. Hello –
    I know that this might be a little belated, but can someone provide some more information about how to do a proper caramel and what to look for? I tried my first caramel a little while back and completely made it burnt and bitter (unfortunately not realizing it until I added it to my pie and bit into it, ruining the whole thing) Since then, I am deathly afraid of caramels. Help!

    1. Hi Christina — My friend David has a great caramel tutorial, with pictures. I bet it will help. And everyone burns it the first time — just dump it and start again if it happens. It’s otherwise (as you found) impossible to lose that burnt flavor.

  38. I’ve been looking for the *perfect* pineapple upside down cake, have made a few and gotten close but this recipe……..THIS ONE is absolutely THE best upside down cake I have EVER tasted.

    After the first bite I thought I’d died and gone to sweet, buttery heaven, it’s just THAT good!!!

    Thank-you soooooooooooooooooooooo much for sharing!!

  39. hey deb, long-time listener/first time caller here. just put the cake into my oven, only to realize that the recipe says 3/4 STICKS of butter, not 3/4 cup. will let you know how it turns out.

  40. My boyfriend’s birthday is coming up and I want to make this cake but I want it to be vegan. Does anyone think this wouldn’t come out as well if I used egg replacer instead of eggs (and earth balance instead of butter)???

  41. Hi,
    I made this cake for Thanksgiving. Turned out pretty well—flavors were good, but no crackly caramel on top at all. Guess I better view that tutorial from your friend David, because I wouldn’t even call this *flavor* caramel. When I was making the caramel in the iron skillet, it was like a weird little science experiment; it was very shloopy and rolly-polly,slipping all around the skillet. The cake itself was mostly good, but a little mooshy on top. Also, the pineapple was a little tough; I used fresh, but maybe it was a little too thick here and there. Maybe i just didn’t bake it long enough. Sigh. Next time… Thanks for the recipe though!

  42. Hello again. Just looked at your friend’s tutorial on making caramel. Hmm. Very clear now, when I made the PUD cake, I did NOT make caramel…

  43. for vegans, I would recommend replacing butter with coconut oil, but I’ve never made this particular recipe with coconut oil, so I can’t be certain.

    I made this lovely cake for a Hawaiian themed office party, and it was all gone in the blink of an eye. It disappeared so quickly that I didn’t even get to taste test it, though I’m pretty sure it came out well, judging from my coworkers’ comments.
    After getting home, I decided to make another one just for myself, and decided to double (no, actually triple) the amount of rum in the cake batter. (It essentially turned into a very delicate rum cake with pineapples on top, which is also delicious)

    By the way, the first time I made this cake, I didn’t realize how much syrup would come out of the pan when the cake was turned over, so I made a huge sticky mess on the kitchen counter. Now I know why you included keeping the plate and skillet firmly pressed together in the instructions.

    1. Hi Cristina — Don’t be intimidated by the stove top caramel; this isn’t like one for candy making, where the temperature has to be exactly right. It’s really about getting the ingredients together into a smooth sauce. As for the Ad Hoc recipe, I can’t imagine it being any less than perfect. (I can’t wait to pick up that book but am not buying a single new cookbook until I crack the cover of the last 10 I’ve bought.) It’s Thomas Keller, after all. That said, I’ve made upside down cakes that had you throw everything in the bottom of the pan and promised that they would caramelize in the oven; sometimes they did, sometimes they didn’t. There’s an extra “security” layer in doing it separately.

  44. I made this last night minus the additional rum on top of the cake, and it was fantastic! Tastes grown-up, but my 10 yr. old loved it too. I made the “caramel” in a separate pan and poured it into a cake pan, since I don’t have a seasoned iron skillet. Turned out beautifully. I live in high altitude, so I reduced the baking soda by 1/4 tsp. Thanks for the recipe!

  45. Absolutely fantastic recipe! The caramel looked somewhat separated in the pan, but baked perfectly. My pineapple was really sweet so I cut the sugar in half and it was well balanced. This cake was easy to assemble and what a beautiful presentation. And, thanks for the great tip to carry and serve the cake in a springform pan.

  46. My mom sent me a giant pineapple as part of a fruit basket for Easter. I live alone and don’t generally eat lots of raw pineapple. That week that it so happened that I also needed to bake a cake for a co-worker’s promotion party. I’ve always loved your recipes, so I knew to come looking here for a solution to my two-part dilemma. The pineapple upside-down cake worked beautifully. Easy and delicious! The caramel seemed to slide down and concentrate mostly in the “crust” of the cake, making that part even more divine than the rest.

  47. My hubby loves PUD cake and makes a skillet version (but with a cake mix). We decided to have a PUD cake “throw down” last night. Hands down, this recipe blew his out the water. Everyone who had some loved it. Thanks again for your great posts.

  48. So I know this recipe is three years old now, but I just tried it for my first attempt at making a pineapple upside down cake. It was delicious for sure! Thanks for sharing. I still think I like raw pineapple better though; Any other fruit suggestions for a good upside down cake?

  49. I was looking for a pineapple upside down cake recipe to bring to a friends house and this one sounded delicious – and it was! I only had a 12″ cast iron and ended up needing to cut the baking time down by 10 minutes. Otherwise everything worked just as well. Thanks!

  50. I was thinking of making two of these, then layering one on top of the other for a two-layered cake. Do you think this will work? Or will the top cake be too hard to place on top of the bottom one?

  51. I made this yesterday as an apple upside down cake and it worked very well! I layered about 3 thinly-sliced apples on top of the caramel, swapped the pineapple juice in the batter for apple juice, added 1/2 tsp. of cinnamon, and omitted the rum. Definitely worth a try if you’ve got apples on hand! I served it with a scoop of vanilla ice cream and a sprinkle of cinnamon and it smelled amaaaazing.

  52. I just made this as apple cake (thanks, Darcy, for the encouragement) and it looks gorgeous. I fanned out the apple slices and inserted a few cranberry jewels; used cider in place of pineapple juice and apple brandy in place of rum. Won’t know till tonight (Thanksgiving) how it tastes; wish me luck on getting it safely on and off the subway.

  53. Is the caramel supposed to harden after you remove it from the heat? I cooked it for the 4 minutes but I’m worried because it’s pretty hard and I’m not sure if it will soften up as the cake cooks?

  54. It did soften and it was EXCELLENT! I made it for a friend’s birthday and took it to our favorite hole in the wall bar, which is always a great way to make new “friends.” Thanks for a great recipe!

  55. I have been a fan of yours for a long time. I made this tonight. It was phenomenal, according to two experts who claim pineapple upside down cake to be their life long favorite. Thanks and kudos to you.

  56. Thanks so much for this wonderful recipe. I made the cake for dinner tonight — using fresh pineapple. I used an old well-seasoned cast iron pan and the cake came out beautifully. The consistency of the cake is great. The pineapple topping is perfect. I served it topped with some whipping cream. It was a big hit and definitely a recipe I will use again.

  57. What exactly is the definition of a “well-seasoned” cast iron skillet? I’m not too familiar with them. My roommate has one that I was planning to use … but I’m not sure if it’s “well-seasoned.” If it hasn’t been used much, then should I just use another pan? Would a glass pan work?

  58. Okay, so I have decided to stop looking for recipes anywhere else but on your blog! I’ve made your cocoa brownies, blondies (delicious by the way!), and granola bars – and they all came out perfectly. And now this cake, which was so good. Thanks so much for the great recipes!

  59. I just popped this out of our iron skillet that we don’t use enough. Left out the rum and used a 12 inch skillet. It was done in 30 minutes. I was praying as I tipped it over the plate because I was sure it would stick. Miracle of miracles it popped out perfectly! This dessert,along with banana pudding was a standard growing up with my southern Mama. this was my first time making it myself-and also my first fresh pineapple. I can’t believe how awesomely good fresh pineapple is! Can’t wait for hubby to get home to try it. Thanks for a great recipe!

  60. Today is National Pineapple Upside Down Cake Day (yes, it really is). Anyway, this was always my Dad’s favorite dessert, and your version tastes exactly like the one my mom made for him on his birthdays. Thanks for bringing back some fond memories…

  61. My sister and I just made this cake yesterday for Easter. Ok, it was mostly my sister who made it but I helped with the pineapple. We found these gorgeous pineapples at the store and decided to make fresh pineapple upside down cake. My sister was lamenting having left behind her Wolfgang Puck version so we went to the internet and finally found your recipe. And are we glad we did. The cake was easy to put together. I pureed the trimmings with a scant bit of water to make a frothy pineapple juice. The batter never broke or curdled. A little trouble getting all of it out the pan , but it was fixable. The cake was perfectly moist, just right in sweetness and absolutely delicious. It was a perfect ending to an outdoor Easter cookout. Thanks for sharing this recipe.

  62. You ladies mean Ina’s plum cake tatin, don’t you?? Ohhhhh, I’ve wanted for ages to make THAT! I had so much trouble finding good fresh plums at the market; they’re apparently really susceptible to pest problems, japanese beatles, etc and birds love them. If anyone’s had any luck with it, please let me know how it turns out. And this pineapple cake sounds heavenly. Will have to use it as an excuse to buy a springform! :)

  63. thanks for this recipe! too much fruit that needed to be consumed over the weekend – late spring is such a tough season – turned into having a wonderful cake (and tons of strawberry smoothies). having been a lurker/avid reader i just wanted to send kudos for this recipe. i never thought that pineapple cake would be this good! if someone would have told me about it, i would, admittedly, have looked doubtful. having neither rum nor pineapple juice in the house i substituted those with ginger syrup and orange juice. worked perfectly well, tasted fab and the ginger, as the rum would have done, gave the cake a subtle kick.

  64. I just made this cake and it is the favourite thing I’ve ever made! Thank you so much for this recipe, I’ve mentioned you in my blog about it! I love that you did this for Livestrong, too – so appropriate!!

  65. Deb:
    Used your new suggestion (Oh, where did I see it?) about using barley flour . . . used 1 cup all-purpose and 1/2 cup barley AND added a bit of fresh ground sea salt to the caramel AND used only 3/4 cup sugar (PUDCs are very sweet anyway) AND THIS IS THE BEST PUDC I EVER, EVER TASTED! Quick cake, amazingly delicious cake . . . what’s not to love?!?

    Thanks for this and all the adventures you’ve encouraged me to take. Good luck on the book . . . I wait with baited breath although I have 3 fat binders of your recipes WITH pix already! :-)

  66. I’ve made this cake twice! It’s delicious and moist and pretty hard to get wrong. I only changed two things, I did use canned pineapple, because I refuse to buy a 10$ pineapple. But more importantly, the rum! I put in exact amounts the first time around, but when I made it the second time, with my mom egging me on, I doubled the total rum.
    It was absolutely wonderful. I would prompt everyone to be generous and let the rum flow!

    Thanks for the fantastic recipe!

  67. wahh~~ *sulk*. I under estimated my stove and burnt the caramel, which in turn boiled the butter and the two refuse to blend together.

    I used fresh pineapple I froze, chopped walnut to fill the gaps, and thrown some chopped mangoes into the batter. I also only used 3/4c sugar in the cake. Due to lack of pineapple juice, I used 1/4c lemon juice + 1/4c rum. I also used 2 whole + 1 white of med eggs instead of 2 large (if you microwave the yolk, it taste like boiled egg yolk…except the exploding part).

    I like the fact it’s moist and think it taste MUCH better the second day when the pineapple, caramel and rum have made peace with each other and blended together.The cake’s a bit dense, think I put too much liquid in =(

  68. p.s. this is the first time I made your cake and was unwilling to share, and my friends think it’s the best cake yet. I think the chopped walnut give it an extra crunch, and mango in the batter made it more fruity, and I stand by the believe it taste better the second day when the flavors blends and when cold (it’s the summer!). I finished 1/2 of it myself in 1.5 days while my friends bribed me with Chinese snacks and finished the other half. Dangerously tasty.

  69. I’m trying this recipe but with cupcakes, so I can mail them to my dad. I don’t know if it will work but it’s worth the try, right?

  70. Two of your cakes within a week!
    For the first time in my life, I baked a cake – the caramel cake you have a recipe to here. I suppose I mixed the batter a little too vigorously and thoroughly, and the temperature was too high (because Fahrenheit is not the same as Celsius and I was overly excited!), but the cake tasted just fine. It just cracked in the middle. Yes, I am a complete novice.
    Today I baked this cake, and it looks just perfect! I haven’t tasted it yet, but my gut tells me it will be just fine.
    Thank you so much! Your great food photographs and detailed instructions finally got me to try my hand at baking :)

  71. I love this cake – it’s moist and delicious and always turns out well.

    One complaint though – I wish you (and other American chefs) wouldn’t use “sticks” of butter as quantities in your recipes. I’m in Canada and I buy butter by the pound. It’s one block. One stick = 1/4 lb, I know that, but when it gets down to 3/4 of a stick, I have to get out the calculator. I know it’s a small thing, but it would be nice if you could use cups or grams.

  72. I made two of these cakes for a big family get together. The best pineapple upside down cake I have ever had. The cake is very moist and tender. Also it is very easy to make. This cake will become a tradition.

  73. I *love* pineapple upside down cake. I love it so much that I made it as one of the first cakes ever that my daughter ate. And I used this recipe…fantastic. She loved it so much that she’s asked for it to be her birthday cake. So this week, I’ll take the request on as pineapple upside down mini-cakes. We’ll see how they turn out!

  74. Aha! I found the ‘comment’ space! I made this last night and it was a big hit! Our friend is a super cook and hard to impress ~ they all loved it! The rum in the batter was perfect and the gooey topping was mouth watering ~ I topped it with a whip cream dollop ~ I’ll definitely make this again! Thank you!

  75. IMPORTANT!!! Using an antique Wagner “10”- ~12″ round and verifying my oven temp, the cake was done in ~20min- cast iron gains and retains heat exponentially, adjust recipe accordingly- in a “8” ~10″, I would check at 15 or 20 min.

  76. I just got all set to make this cake and then realized that you call for the butter in “stick” measurements- only problem with that is that I have two different sized sticks of butter at home- one is 8 tablespoons= a stick, the other 4 tablespoons= a stick. If I need 3/4 of a stick, should I be using 6 tables spoons of butter or 3? Help!

  77. The spring like weather we’re having here in Charleston inspired me to try this cake, It tasted wonderful! It was also really quick and easy to make. I made the mistake and tried to bake it in my fav flower shaped la forme springform pan. The butter melted out and I thought I would burn the house down. After an hour or two of cleaning it out..I wrapped the bottom of the pan in foil, put it on baking sheet and it went back in. It still turned out great! I was making two more for friends and although they were a bit fluffier, they all survived! Thanks for sharing this great recipe!

  78. I have been married 22 yrs and my husband has spent the WHOLE time telling me how much he loved his grandmother’s cake. Naturally, I knew better than to try to compete with a lovely dead lady and little boy memories. But, today I bit the bullet and tried this recipe. As the look of rapture spread over hubby’s face, I felt the ground give a little tremble when the LOL turned over in her grave. Rest in peace!

  79. Hi Everyone,
    OMG have made many recipes from your site when ever I make anything I use your site first. Most dishes made never last through the night… Thanks for all the great recipes …; )

  80. Do you have a suggestion for which dark rum to use when baking? I made a rum cake once using Myer’s, and it seemed so strong… Granted, I know it was a rum cake, so it should be rum-my, but I hope you can give an example. Thank you!

    1. I don’t have a choice brand, and usually don’t use the very best stuff for baking. If you’re nervous about the flavor (I really don’t remember this having any lingering rum-y flavor, but it’s also been a few years since I made it!), you can always halve it. Good luck!

  81. I saw a few people in the comments used a 12″ skillet instead of a 10″ skillet, but do you think the cake would fit in a 9″ skillet? I am planning on making this for my mother in law’s birthday next month and I have 9″ cake pans if it seems like it would be too big, but just wondering if I can get away with it? Any thoughts or others who have tried it in a 9″ skillet?

  82. Hi deb! Should we butter the cake pan before adding everything? I can’t wait to make it! Looks so delicious!
    -Tina :)

  83. Made this tonight using gluten free flour (Namaste Perfect Flour Blend). It was wonderful!! I used a Princess House skillet that is stove top and oven safe. It worked great! My mom would be proud!!

  84. I’ve just made this for my son as pineapple upside down cake is his favourite. I have always made it with tinned pineapple, golden syrup and a standard sponge recipe, which is nice enough but not exactly wow. This recipe has certainly jazzed up our old favourite. The caramel, pineapple and rum work really well together and the sponge is lovely and light. My son has already had 2 portions, I’m not expecting any leftovers for tomorrow.

  85. This is the perfect PUD! I’ve made it a handful of times and it’s on my favorites list of baked things (I’m a baker). Everyone loves it. They think I’m a magician! I’m bringing it to a 4th of July potluck tomorrow. I can’t wait!

  86. I saw Martha Stewart making this earlier on her show and want to try it myself. The problem is, I don’t have an oven yet. Can I use a steamer?

  87. Hi.was searching for the recipe for Pineapple Upside cake with macadamia nut filling which is sold at Dole’s Plantation in HI, made by Ted’s Bakery on the North Shore. Your recipe is the one which Google presented…sounds heavenly…do you happen to include the macadamia nut filling at all?? I will try your recipe as my Grandchildren fell in love with it at Dole’s….. Thanks!

  88. Hi Deb, I love your site so much. Thank you! I’ve made several of your recipes and they are always fantastic. I’ve also impressed many non-baking Jews with your challah.
    I made this cake tonight (it is my first cake, ever) and found that it was too sweet and that the caramel didn’t come out right. As I was cooking the butter and sugar in the pan to make the caramel, they wouldn’t blend well, but after 4 minutes at medium-high heat, it seemed too dark, so I decided it must be done. However, in the finished cake, the caramel is much darker than that in your photos, and it tastes extremely, almost sickly, sweet. What do you think I might have done wrong with the caramel? Could it be burned? I did use salted butter instead of unsalted, but I don’t know if this could be related. Finally, how might I modify the recipe to be less sweet?

    I can’t tell you how impressed I am with your writing and recipes. Very high quality.

  89. My husband volunteered my baking services for his father-in-laws birthday party. Instead of the tired old white or chocolate cake I decided to make pineapple upside down cake instead. For once I followed a recipe exactly. It was good. Thank you for this recipe.

  90. I always wanted to try this cake, ever since I saw this famous Desperate Housewives episode where Gabrielle tries to bake one herself so her husband doesn’t find out she’s been spending time with Bree Van de Kamp. Thank you, this recipe makes it look much easier than on DH! I’ll try it soon!
    Love,
    S

  91. My fiance improvised pineapple/red+greenpepper/redonion/cayennepepper puree to top red snapper yesterday (yes, I AM boasting). Now I want to make a mini version of this cake w leftover canned pineapple. Unfortunately/fortunately I have abstained from alcohol for, well, it will be one year on October 24th. Are there any rum alternatives for former rummies?

  92. WOW… I just did it tonight. First the smell in the kitchen was amazing. It was ready in about 40 min in the oven. Decorated with some pineapple leaves…. It is amazing on taste. Thank you!

  93. Just made this, and it’s a great recipe. Husband loved loved loved it. I personally don’t like overly sweet desserts, but I used the entire amount of sugar in the recipe, and it tasted good to my taste. Also, I used brandy (didn’t have rum) and it was fine. Lastly I baked it using a springform, which actually worked out fine. A little of the caramel oozed out and got a bit burned (our sensitive smoke detectors went off) but I put a cookiesheet underneath to catch the drips, and problem solved. Springform made it very easy to turn out.

  94. This recipe rocks. Especially with a fresh pineapple. Wow. Very easy and, since it only uses approx half a fresh pineapple, good way to use one that has become “over ripe” on one end. Did this for a friend’s birthday today and RAVE REVIEWS. A little vanilla ice cream on the side doesn’t hurt.

  95. Two things:
    Madeline — note that any alcohol used in a recipe like this loses its alcohol content in the baking. Only the rum flavor remains, and frankly I could not detect it anyhow. You might substitute an equivalent amt of other liquid and be fine.
    Otherwise– have to say the cast iron skillet worked like a dream here.

  96. I’ve made this for my husband twice this week and its our dessert for Thanksgiving! Thanks for all the yummy recipes. I haven’t tried one yet that didn’t turn out exactly as it should!!

  97. OH. MY GOODNESS. I made this tonight because I had a rogue pineapple I was afraid would go bad before we could eat it, and all I can say is this is hands down the best pineapple upside down cake I have ever made in my life. I made some slight alterations to mine…I added a t. of almond extract, & 1t. of cinnamon. I can’t imagine this cake without either, they were great additions. I will say, mine was not set in the center and I wasn’t completely thrilled with the graininess from the sugar in the caramel sauce (I cooked it for the full 5 minutes). I’m wondering if I didn’t use enough pineapple, and I also used a 9″ pie plate. Perhaps that extra inch of surface space would have helped the cake cook thoroughly. I’m sure it’s by no fault of yours, and more my mistake. But regardless, this cake was phenomenal, even my boyfriend commented on how amazing it was and he isn’t a big sweets person. This is not the first recipe I have made off your blog and it certainly will not be the last. I’m pinning and telling the world. :)

  98. Omg! I must say. I was looking for an PUSD cake recipe..and I went through several that just didn’t interest me. But this one did! I’m better at cooking than baking. But after following the recipe precisely (with a few additions) it turned out fantastic! I made it yesterday and its over today. So I didn’t have a 9inch pan so I used a heart shaped baking tin. Haha..the. Batter fit quite perfectly.

    Additions I made to the recipe.
    Well firstly I used dark brown sugar because that’s what I had. And the caramel turned out so delicious I just ate it off the remainder. From the cooking spoon as it dried.

    Secondly I added 1/2 cup of finelly shredded sweetened coconut. Since I did not have dark rum. I only had white and coconut rum, I thought coconut rum would be a nice addition to the cake. And I sprinkled it on top after the cake was done and flipped.

    I am not sure if the coconut rum made all the difference in the batter but, I know it tasted fantastic!

    I don’t usually post on blogs but this recipe needed appreciation! I am inspired to bake more!

    Thanks!

  99. Late to this party, but thought I’d share: took your suggestion on your cranberry-caramel upside-down cake and made this one instead, substituting 2c+ of fresh cranberries for the pineapple, orange juice for the pineapple juice, and brandy for the rum (I think the rum would’ve worked fine, but I didn’t have any). Dropped some cloves in with the berries/butter/sugar mixture; added a bunch of cinnamon to the cake batter. Came out FABULOUS. Much prettier than the average upside-down cake thanks to the jewel-like cranberries, and delicious. People tried a sliver, then cut themselves a big piece and went out into the living room to tell their friends. This is a cake to make lots of and stash in the freezer for suddenly-announced potlucks…it’s that good and that lovely. Thanks!

  100. I just wanted to note that for the past three years, this has been the ONLY cake my significant other has wanted for his birthday. We use Bacardi 8 spiced rum, and it is our preferred option but other spiced rums work as well.

  101. Pineapple Upside Down Cake has been a staple in my kitchen for the last .. many years..Before that it was a treat in my Father’s kitchen (we did not trust Mother to cook..she liked to experment) All I ever cook this cake in is a cast iron fry pan.. but then again all my fry pans are cast iron. I have used it for breakfast, when in a pinch to the delight of the children. I often use other fruit than pineapple. Peach is tee best and Damson plums (the little prune plums) work well. Such a versatile recipe, and oh so yummy. No rum in mine when the children were small.. but now.. well.

  102. This cake was absolutely fab! I decided to add 1/2 tsp of cardamom and I am so glad that I did. I made this for my mom’s birthday & she LOVED it! I was afraid to put too much rum on top but next time I won’t be and might even add some crushed pineapple or shove even more rings on top.
    Thanks for sharing – your site is always my go to place when I need inspiration. You never let me down Deb! ‘cept now I’m vegan (except when it came time to cut this cake). Any chance you’ll be adding a vegan friendly category to the mix??

  103. I just made this cake and it is so good! The cake is light and fluffy and not to sweet. Thank you for sharing your recipe. This is keeper.

  104. I made this in a 9 inch cake pan (regular depth), cooked the caramel as directed and spread it into the bottom of the pan, then poured the cake batter on top. I bake a lot and know my oven’s quirks re heating, so I used a lower temp, rack in the middle of the oven. After 15 minutes, the top was browning too quickly, and at 20 minutes, the caramel started bubbling up and then over the edges and onto the oven floor. Lots of smoke….and I decided to remove the cake before it was done. Nice flavor….cake batter was a keeper. I suggest using a deeper cake pan or reducing the amount of the caramel. Even if there hadn’t been overflow, the ratio of caramel to cake is a lot more than the classic upside down cake.

  105. P.S. Re post #145…….I took the partially baked cake, put it into a greased 9 x 13 inch baking pan and baked it the next morning @325 for about 18 minutes…turned out well.

  106. I just took this out of the oven! I used a cast iron skillet. The turn over was a little tricky by myself with a hot skillet but I managed. The only modification I made was adding a little cinnamon to the caramel and using Cap’t Morgans spiced rum instead of dark. I thought it would have more caramel running over but looks and smells delish! It turned out dense, moist and tender with a sweet, almost crunchy topping. I think I’ll add a little more rum next time ;)

  107. I made the cake with canned pineapple and it was lovely! The cake base was perfect with half the amount of sugar called for and (an accidental) 2 extra tablespoons of butter. I also reduced the caramel by half and creamed instead of melted the butter and sugar.

  108. I live on the souther Caribbean coast of Costa Rica, and our annual pineapple crop is swamping me. I found your recipe today after searching for what seemed forever for a pineapple upside-down cake that did not list as ingredients: 1 boxed yellow cake mix and 1 can of tinned pineapple. Thank you, thank you, thank you.

    I used miel de caña, a kind of local cane syrup, instead of light brown sugar, and caramelized it with butter in my handy cast iron pan/ pot. The cake is in the oven and it smells heavenly.

  109. I know I can leave out the rum since I don’t have any, but I was wondering, how would the flavor be if I subbed in bourbon instead, which I do have? If I don’t hear back before Sunday, I’m just going for it. :)

  110. Reply to myself if anyone was curious: bourbon worked out great. I added some to the caramel-making process, the amount in the cake batter itself, but skipped the drizzle.

  111. Making this right now for my family, it’s in the oven and also the first time I make a cake from scratch. My family lives on gourmet recipes so I’m justtttt a little scared how it’s going to turn out but the cake batter tastes already extremely good… Not that I tried it or anything ;) I’ll post the reactions afterwhen everything is done!

  112. Just made this with some coconut cream in the caramel and the batter, a scattering of dried coconut with the pineapple, and almost a tsp of cardamom. The cardamom is overpowering the coconut flavor I was going for, but it all tastes so amazing, I don’t care. Coconut cream may well become a regular part of many caramel sauces to come. Trying really hard to not eat a third piece right now!

  113. I’ve only been looking at your blog for a couple days. My daughter sent me here. She’s made a few of your recipes from the blog and / or your book when she visits.

    Out of curiosity i looked up this recipe. It’s pretty close to mine (originally from mom but with mods). I use the darker brown sugar and sometimes demerara sugar. I also add the pecans and maraschino cherries although the cherries are probably more for appearance on a kind of drab brown cake than anything else. I’ve never used rum but I’ve made a note on my recipe to try that.

  114. If I don’t want to use the rum should I substitute or just leave it out? Bunch of recovering alcoholics in my family, lol.

  115. I haven’t either, and that’s why I was horrified (that, and it was for my son’s birthday)! It was baking, rising well, looked good but not quite done after about 35 minutes… then when the timer went off at 40 min., it just…. liquefied. I’ve never seen anything like it! We ended up letting it cool, inverting the goo into a glass pan, and microwaving it into something like a dense cookie, but it was not quite what we expected. Anyone know what on earth could have happened?

    1. Becca — It sounds like it wasn’t baked through. I mean, if there’s wet batter, it needs to be baked longer. A tester needs to come out clean. Do you have an oven thermometer?

  116. Yes, and I really have baked other things successfully before! :) This was just bizarre– I know a tester needs to come out clean, but this went from almost ready to absolute liquid– like it reverted from cake back to batter. My mother, also a successful baker, and I were just stumped. Could anything like too much or too little of something make this happen, or maybe old baking powder… or too much humidity.. or an altitude issue?

    1. Becca — Are you at a higher altitude? Because I’ve always lived at seal level, more or less, it’s definitely one of those things that stumps me more as a baker because I haven’t experienced it firsthand.

  117. We are in the mountains, but only at about 2,000 feet, so I’ve never had to adjust recipes before. But maybe it was a quirky mix of factors that all came together to create… well, chaos! Just wish I knew, because what was left was still great, so I’d love to try it again.

  118. Hey there Deb, I attempted this recipe this weekend for my mother’s birthday cake, and we all LOVED it! I recently discovered that some grocery stores carry maraschino cherries that have no dye or preservatives, and I couldn’t resist adding them – Heavenly! I did run into an issue with the caramel, though. I made the caramel in a calphalon skillet (melted the butter first, added the sugar) and then poured it into a 9″ cake pan after a 4 minute simmer with constant stirring. It was smooth, poured OK and started to stiffen up fairly quickly, but never completely hardened as I was assembling the cake on top of it. When I de-panned the cake, the caramel had drifted to the center (so a six inch circle of caramel in the middle of a nine inch cake) and had turned quite grainy. Any thoughts on why this happened, and how to fix it? I assume the drift-to-center resulted from a dip in the pan, but the grainy caramel? I’m not sure what I did wrong there. Thanks!

  119. Thanks so much! The Pampered Chef has a one-pan recipe for this, but it uses cake mix and yes, cherries. Love yours more, I have to try it! TPC has a new piece of stoneware that can go from the stovetop to the microwave and they’re touting that for their PUDcake and I’m going to use it for this. Many thanks again! (Full disclosure: I do sell TPC products but this is a sincere comment, I’m so glad to find a REAL cake recipe for this!)

  120. I’m sorry, there is no substitute on this green earth for my moms (from the box and can) pineapple upside down cake. I’ve had lots of them from those who fancied themselves really good (no box) cooks. They always taste like golden cake or worse golden cake with pineapple juice. Mom used boxed SPICE cake. And yes. Maraschino cherries. Hers was never rubber but moist and delicious. The brown sugar and butter at the bottom (née top) did wonders for skinned knees and that particular summer sadness little girls get when their friends flat leave for the cousin who has a pool.

  121. First of all, a comment to Charleen about printing. I highlight the recipe, right click and copy it, then email it to myself. Voila! No comments!

    I made it this Sunday and had no rum (we can’t buy alcoholic bevs on Sundays!), but I just soldiered on without it. The caramel sauce in the cast iron skillet was heavenly. The cake rose up beautifully and came out completely onto the plate! Exclamation point because I’ve never made an upside down cake before! I can’t believe how simple the whole process was. And with just all purpose flour, not cake flour. Anyway the cake was enjoyed by all who were lucky enough to get a slice. One person did suggest I at least sprinkle some pineapple juice over the cooked cake since I had no rum. Most said, with their mouths full, not to bother. Thanks!

  122. Oh, and it’s possible that the person’s cake liquified (mentioned in the comments above) because she used 3/4 cup of butter instead of 3/4 of a stick. I almost did because I usually see it written in cups. Just a thought.

    1. Hm… that’s a good point. Becca, does that sound like what could have happened?

      Lauren — Hm, grainy sounds off. I mean, I don’t think of this as a completely smooth caramel once it hits the cake (crumbs, bits of pineapple, etc.) but it shouldn’t taste gritty or anything.

      Dawn, Charleen and anyone who would like to print a recipe — There is a print template for each recipe. You get to it by clicking on the “Print” link underneath each recipe, before the comments begin. It’s usually one page, two pages for longer recipes.

  123. I just made this today, it came out excellent! I used a 12in cast iron pan (that all that I had), so it was thinner and wider, was done in 40 min. I followed the recipe exactly, other than I used 3/4 cup of sugar in the batter vs the full cup and it is plenty sweet, I may do half a cup of sugar next time. thank you!

  124. This is the absolute best pineapple upside down cake ever!!!

    I have had such a craving for it lately and decided to make it for Thanksgiving. (Eh, not traditional, but who cares!)

    Thanks, Deb!

  125. My husband and I made this cake last night for my birthday on a whim – and it was probably the BEST cake I’ve made in months! Truly fantastic recipe, thank you so much!

  126. Do you think that this recipe would work in a 9×13 pan? I want to make it this weekend, but I am living internationally and have limited cookware options. Thanks!

  127. Hi Deb, thank you for all the fabulous recipes you put out. Love that you are thorough in your explanations. I have attempted this cake twice now and have failed to make a smooth caramel (your Paris caramel sauce is a staple in our fridge and I have mastered that). I don’t own a cast iron skillet so I have tried to make the caramel in a non stick little pot and poured it into my 9-inch cake pan. Both times, I was careful of gently melting the butter and then adding the light brown sugar, and I whisked it continuously for 4-6mins but still ended up with a grainy texture. At about 6mins, the toffee started to ball up so I simply just poured it into my baking pan. Mind you, the rest of the cake baked up beautifully and the texture of the caramel on top of the cake was alright after it got inverted. Please help if you get a chance. Thanks!

  128. made this cake today for easter tomorrow.. actually made 2.. i got this bright idea to use a whole stick of butter and a whole cup of brown sugar.. and it was not necessary at all. next time i will stick with the original recipe.. also, i used the fresh pineapple. super tasty! thanks for the great recipe

  129. I made this cake for my dad for his birthday. Normally he claims to not care too much about sweets (if it weren’t for my mom’s sweet tooth I’d swear I was adopted!) but growing up pineapple upside down cake was always his favorite. When he ate this cake he claimed that it was the best he’d ever had and he wasn’t just “blowing smoke”. He even said I was allowed to move back home if I ever needed too haha. Great cake! Thanks! My caramel took almost twice as long to come together but I blame my crappy pan for that. For the cast iron does it require extensive cleaning afterward and reseasoning? Thanks!

  130. I totally agree about chai…….no thanks!
    I love upside-down cake, and I tripled this recipe last weekend; one cake for a party, one for a new mom, and one to keep. I bought 2 small pineapples, but it wasn’t enough (I like lots of fruit), so I also used canned pineapple on one, and added some fresh blueberries. Well, everyone at the party loved it, but they didn’t know what they had missed. When we tried the cake with fresh pineapple, there was just NO comparison! I think most fresh or frozen fruits would yield better results than canned, here. This recipe is a keeper!
    (By the way, I used a Passover cake recipe to make an upside-down cake for the Seder once and it worked out quite well.)

  131. Just made this with peaches from my front yard. Love the way the top (which becomes the bottom) has a sweet crusty thing happening. I made mine in a 9 inch springform pan and… peaches are a lot juicier than pineapple… Don’t put a juicy fruit in the pan until ready to pour the batter over!! it started leaking before I could get it into the oven! Still tasted fantastic, however. This is a bang-up recipe!

  132. At Christmas time, my dad makes a pear and cranberry upside down cake. Fresh pears and fresh cranberries instead of pineapple and pear juice instead of pineapple juice. It is amazing and delicious.

  133. Oops. I interpreted the 3/4 stick butter as 3/4 cup of butter that was missing its measurement term. (I know, I should know better than to think a 2007 recipe hadn’t been corrected by now!) Can that please be clarified up in the ingredients? After a bit of searching the comments post-baking/dinner/consumption, with the question still stuck in my mind, I unearthed the sad detail that it *is* supposedly to be 3/4 of an 8-tablespoon stick, so 6 tablespoons rather than 12. The good news is that the cake was totally fine baked with 12 tablespoons of butter. (Full disclosure: I made the cake with this batter and the cranberry upside-down cake topping, as you suggested in the cranberry upside-down cake recipe.) Many raves at Christmas Eve dinner tonight. Hmm. OK, so perhaps the confusing line should stay. Maybe it’s better with twice as much butter!

  134. Yikes, sorry for the trouble. This is indeed an old recipe and I try not to use the “stick” measurement these days because it’s very confusing and not consistent from place to place. Now fixed. Glad it was still delicious.

  135. This cake is definitely a winner. I almost found it to be too sweet but with a glass of milk, it was the perfect end to a New Year’s Day, dinner. I thought about cutting the sugar next time, but it was so good as is, I would hate to mess with it! Thanks for sharing such amazing recipes and tips.

  136. My one recommendation for anyone going to try this would be to let the cake cool longer than 5 minutes before popping it out of the pan. It looked gorgeous with the caramel drippings but I would have preferred to let the topping set (As shown in pictures above)

  137. I made this for a family dinner and it was delicious…my mom kept saying how good it was. I thought about reducing the rum on top but didn’t…and I am really glad I didn’t, it was a great touch.

  138. Love this Cake! Anything I try to bake never turns out, so if I can make it anyone can! I didnt use a skillet but a 9″ baking pan. I dont put in rum as I dont drink and never have alcohol around. I used canned pinapple which also gives me the juice. I am making it for the second time as I am in love :). Thank you for sharing.

  139. My husband and I loved this cake! Only problem was when I tried to flip it upside down the bottom layer all stuck to my cast-iron pan – do you have any ideas for what I might have done wrong? It was still delicious – we just ate it right-side up out of the pan :)

  140. Hm idk if anyone here has tried it with this recipe, but if you’re having trouble with the caramel America’s Test Kitchen makes theirs right in the cake pan by mixing the butter/sugar in the bottom of the pan and then layering the pineapple and batter right on top of it.

    Also @ Vanessa: you might want to try flipping the cake put earlier. If the caramel cools down too much it will stick (bUT at the same time if it’s too hot the cake will break).

  141. This is one of my all time favorite desserts. It is so much better than the pineapple upside down cake of my childhood memories. Fresh pineapple and homemade caramel are delicious, of course, but I think it’s the pineapple juice as the liquid in the cake that pushes it over the edge from good to great – the pineapple flavor is infused throughout the whole cake. Of course, I *do* love pineapple.

    I make it without a cast-iron skillet and without rum (replaced with more pineapple juice in the batter). It turns out great each time – both physically out of the pan and taste-wise!

  142. This looks awesome and is next on my to-make list. Can you please add weights? Thank you! (And thank you for letting your readers know we can just go ahead and ask that. It means a lot to us.)

  143. Delicious, made this last night for my sister in laws last minute birthday party at my house. The BEST pineapple upside down cake I’ve ever made and this is one of my favorite cakes.

  144. I made this last night and it is phenomenal! I have never cooked a cake in my cast iron skillet before, but it worked great. In a few months, I can’t wait to try this with fresh, local peaches!

  145. Wow this is fabulous! We had a rapidly declining pineapple and people coming for dinner in hours; when we got to what to make for dessert, my husband said jokingly “Pineapple Upside-Down Cake?” I went for the challenge and with this recipe totally won! The caramel + pineapple combo is just divine and the simple cake with the pineapple juice baked in was just the perfect compliment. Thank you again, Deb!

  146. have made this a few times now for my now 94 year old father in law. Today was his birthday so I made this again. No rum for him and I had no pineapple juice, so I buzzed some pineapple scraps (fresh) in the vitamix and pureed it smooth. Used that in place of the juice along with one T water to replace the rum. all I can say is fabulous! My fahter in law has eaten his fair share of PUDC over the years and this is his favorite.

    Thanks

  147. I just made this (came out of the oven about an hour ago). I’m not sure what I did wrong, but the caramel didn’t cook into the cake as much as it created a soupy layer on the bottom/top. When I inverted it it stayed intact, but once on the plate it was crumbly, breaking off into chunks around the edges. Maybe I cooked it too long?

    The flavor is good, a little sweet for my taste, but the consistency of both the caramel and cake weren’t what I was expecting. Deb’s recipes are always spot on, so I’m sure it was a mistake on my part, but until I make it again I’m not sure what I did.

  148. I forgot to include that if you’re using a cake pan instead of the skillet, does the cake pan need to be greased/floured beforehand – thanks!

  149. I made this tonight, sans rum and using canned pineapple. Only needed 40 minutes baking time. A very excellent dessert which I will make again. Thanks, Deb!

  150. This was absolutely delish. Moist cake, dripping with caramel pineapple rum magic! Only problem; it disappeared so quickly. Thanks for this recipe.

  151. I live in Uganda where there is fresh pineapple all year round, and this cake… I used not to like pineapple upside-down cake at all, but this cake is in my top ten cakes of all time. I used pineapple puree instead of juice because I was too lazy to strain it, and switched half of the butter for plain yogurt because I ran out of butter. Delicious both ways!

  152. I wishes I had listened to Karen (post no. 39)….
    I bought a brand new, “leak-proof” springform, especially to make this cake, and now the bottom of my oven is smoking black with caramel still leaking from my cake… And yes, I want to cry :-((

  153. Wooooooow! You are my absolute favorite food blogger and this is my go-to site for new recipes. It all works perfectly and turns out great. I like that the instructions are detailed enough to know you’re not doing something wrong (e.g. batter-may-appear-curdled comment). I brought this cake to a potluck tonight and it was a sure hit. Best thing is … Even before I made it, I knew it would be good, just because I found it on your website. I’ve been following you for a few years now and just wanted to say: Thank you!!

    My family loved watermelon+vegetable+feta salad – even my dad, who would never eat fruit and vegetables together! :-) Watermelon lemonade in summertime is the best, my friends couldn’t get enough of the key-lime meltaways on our sight-seeing tour of Slovenia and I just had a couple of the consummate chocolate chip cookies last week. On my to-do list: cranberry pie with pecan crumble. Can’t wait! Thank you again for your work. You have definitely changed my cooking for the better and I look forward to what is to come!

  154. I’ve made this three or four years in a row now for my husband’s birthday. It always turns out flawless. It comes together easily by hand and is no-fuss. Thanks for the stand-by!