Pineapple Upside Down Cake for 150

pineapple upside down cake

Note: Recipe has been updated on February 11, 2009 to clarify some instructions and correct a typo.

When we moved to the country, we decided to join the local Volunteer Fire and Rescue Company. It took us a while to actually do it, but both Keith & I became members early this year. My role is strictly support and fund raising. For instance, I build our web site, I help with putting together flyers, brochures, with setting up fund-raiser dinners, breakfast, bake sales etc. Those activities are more critical than ever this year, as we are buying a much needed new fire tanker. Joining a volunteer fire company is a sure way to become more engaged in a new community and it allows you to give your time and your skills to your local community in a way that makes a difference: we help neighbors in emergencies.

This past week-end, WVFR offered an-all you can eat ham & oyster dinner as part of its continued efforts to raise money for our new tanker fund. I was working that night, cooking a 5-course dinner for 11 on a lovely hilltop house, I would not be able to participate. So I said I would bake one of my specialties: a pineapple upside-down cake.

I have a soft spot for upside-down cakes (something easily verifiable by looking at the list of cake recipes I posted so far); I love pineapple, one of the fruit growing at my childhood home; and I love the uncomplicated unsophisticated sheer goodness of a good pineapple upside down cake. Don’t get me wrong, I have eaten my share of unpalatable ones – generally too dry. But this cake is moist and flavorful.

I have found that it’s a popular cake at gathering (I rarely have any left over to take home); people of a certain age (over 40) reminiscence fondly about it (how their mom used to make one for their birthdays for example), and yet – not many people make it today. You can be pretty sure to see multiple plates of brownies at a pot-luck, but I have never seen another pineapple upside-down cake (as a matter of fact, a young 18-year old at that dinner had never seen one). It does take a little time to make, but really, not that much. Is this the butter in it that people are afraid of? Is this that there were too many poor versions that were made? For me, it’s one of those ideal, comforting, utterly delicious and homey cake that can be made in advance and is good at any time of the day, like a real homemade pound cake, as a matter of fact. And it’s so good for breakfast with a cup of strong coffee made stove-top in the percolator.

So, on Friday late morning, after picking up some farm eggs, flour, maraschino cherries and good milk at one of the local country stores, I arrived at the fire hall to use the kitchen and make lots of it. The day before, our Treasurer, our Chief and I had gone bulk-shopping for 200 in Winchester, but Costco simply did not have some of the items I needed – or had them in quantities that were simply too large for my purpose. So I stopped at Roy’s in Sperryville to round up what I needed.

The original recipe was printed in Saveur Magazine in December 1998, almost 10 years ago. I have saved all my issues of Saveur and often go back to them, but I have a particular fondness for the article accompanying the recipe: it was titled “The Convent Cook – Maria Tisdall rescued herself from restaurant hell – and answered the prayer of 65 nuns.” And it was the story of how this match made in heaven between Maria and the Benedictine sisters at Saint Walburgha monastery in New Jersey came to be. Only one recipe was published: the Pineapple Upside-Down Cake. The ingredients were for an 8” x 8” cake, but the picture showed a cake easily twice as big, as it displayed 20 pineapple rings. When I first made the recipe 10 years ago, I was fooled (thinking I was making a large cake) – and somewhat ticked when it was a small cake! Frankly, an 8” x 8” cake is grossly insufficient: it’s gone too fast. I always at least doubled the recipe, sometime tripling it. So in the end, I rewrote the recipe, making made some substitutions, omitting the almond extract and adding some of the pineapple juice and maraschino liquid to the topping – along with a few “tricks” of mine. The cake is rich, so a little goes a long way, but it keeps for several days in the fridge), and it freezes beautifully (cut it into individual portions first.)

And so Friday afternoon, I made four 19” x 13” cakes, each with 24 whole pineapple slices, for a total of 96 large squares. Because we had a lot of food and other desserts, I halved most of the portions in much more manageable size for dessert after such a large dinner. They were all eaten: nothing was left.

As usual, I urge you to buy the best ingredients you can afford. Specifically the quality of the eggs and butter make a huge difference!

pineapple upside down cake

Pineapple Upside Down Cake

Note: Recipe has been updated on February 11 to clarify some instructions and correct a typo.

Make a 19” x 13” cake or 24 large squares


  • 2 tablespoons canola oil to grease the pan
  • 24 tablespoons (i.e. 3 sticks) of unsalted butter (not margarine), soften to room temperature, and divided into 2 stick & 2 tablespoons (i.e. 18 T) for the caramel/topping and 6 T for the batter
  • 3 cups brown sugar
  • 24 pineapple rings – about 3 15-oz can pineapple rings in juice (not in syrup) (you may have a few rings left)
  • 1 8z jar maraschino cherries, pitted and stemmed
  • 1 cup + 2 Tablespoons of whole milk
  • ¾ cup canola oil
  • 2 teaspoons strong vanilla extract
  • 3 cups + 6 tablespoon of all purpose flour (I have used whole white wheat in the past and it’s perfectly acceptable)
  • 4 teaspoons baking powder
  • 1 ½ teaspoon salt
  • 2 ¼ cup sugar
  • 6 eggs


  1. Turn oven on to a temperature of 350 F
  2. Oil the pan with a pastry brush (or your fingers) using up to 3 tablespoons of the canola oil. Make sure to get the corners and sides well. Do not be stingy as you want the cake to unmold easily. Roughly chop 18 tablespoons of butter (2 sticks + 2 tablespoons) and scatter at the bottom of pan. Put pan in oven while it’s preheating. Keep an eye on it, and take it out of the oven as soon as butter is melted. It should do so before the oven reaches 350 F. Put the remaining 6 tablespoons of butter in a very large bowl on the stove where it’s warm to help it soften.
  3. Sprinkle the bottom of the pan with the brown sugar evenly, again making sure to reach all sides and corner. Lift the pineapple slices from the juice (reserve the juice) and arrange them in a grid pattern. Sprinkle 6 tablespoons of the pineapple juice over. Reserve the rest for another use (it’s perfectly good to drink, you know). Sprinkle two tablespoons of maraschino liquid from the jar over the pineapple. You could push one cherry in the center of each ring now, if you want, but they’ll look better if you do this after the cake has been baked.
  4. In a bowl, combine milk, the 3/4 cup canola oil and vanilla. In another bowl, sift together flour, baking poweder and salt.
  5. In the very large bowl where you set it to soften, beat together the remaining 6 tablespoons of butter (which should be very soft by now) and the sugar until light and pale lemon colored. It will look “mealy”. Beat in the eggs, one by one, then add the milk mixture, and the flour mixture (1 cup at a time) beating well after each addition. Pour batter over the pineapple rings, smoothing it out as necessary. It may looks like there is no enough batter: there is!
  6. Bake in the preheated oven until cake is golden and a toothpick or skewer comes out clean, 1 hour to 1 hour and 10 minutes. Remove from oven, let cool until you feel comfortable handling the pan.
  7. Now comes the tricky part: inverting the cake. Position the cake inside a rimmed cookie sheet (rim facing up). Put another rimmed cookie sheet on top of the cake (rim facing down). The cake is now sandwiched between two rimmed cookie sheet. Clamp the two cookie sheets together and invert the cake quickly and decisively but carefully. Remove the pan from the cake carefully. If necessary, use a spatula to remove any stuck ring and put it back on the cake. Scrape any caramel from the pan and put it on the cake.
  8. Push one cherry in the center of each ring.
  9. Let cool and cut into square s, one for each ring.

Voila! Not too bad for such a delicious comforting cake!

Locavore log: eggs, milk, butter – that’s it, I am afraid…

For the Recipe ONLY, in printable form, click: HERE

Individual Pineapple Upside Down Cake

Individual Pineapple Upside Down Cake

Update Dec 2008: following several questions on individual cakes and substitutes for Maraschino cherries, here is a picture on an individual cake using dry cranberries. Cute, no?

20 thoughts on “Pineapple Upside Down Cake for 150”

  • That cake look delicious !
    Do you think I should bake it for so long if I do it just for 2 persons ?
    You know I’m the queen of tiny portions…

  • Vanille, a cake about 1/3 the size should bake for about 35 minutes. A cake 2/3 the size for 50 minutes.

    I have made them individually too – and they are darling:, you can see a picture on my welcome web site page (left hand side). They turn out great and are very pretty! I don’t remember exactly how long I cooked them, I would say 25 to 30 minutes.

    Update 12/22/08: there is now a picture of an individual cake at the end of the post

  • I have a recipe for Apple Upside-Down cake that I am planning to make this week (recipe from BH&G Oct 2007) that has ingredients almost identical except no cherries, but ginger and cinnamon. Very small apples are listed to be halved, stems removed, cored. I am tempted to try for individual serving size. Your photos are always so tempting and delicious looking and I know the finished product is just as delicious as it looks.

  • Oui, oui, oui, en portion individuelle ça donne très bien aussi ! Il faut que j’essaie ça très bientôt. En fait, j’aime bien le motif de la tranche d’ananas et puis j’adore ça l’ananas ! Aurais-tu essayé avec un ananas frais ? Moins sucré, sans doute…Bon, j’arrête avec mes questions…Merci pour les temps de cuisson !

  • Desolee d’avoir mis si longtemps a repondre. L’ananas frais a une texture tres differente – je pense aussi qu’il ferait trop de jus en cuisant. Peut-etre le cuire avant de faire le gateau – au four ou a la poele?

  • Hi Sylvie. This sounds scrumptious…except for the Maraschino cherries, which have a bad reputation with me for being artificially colored (red dye #2 and all that) and maybe artificially flavored. Are there actually decent ones out there?

  • Originally posted 11/11/08

    Paula – I am not aware of “good” commercial maraschino cherries. But they are not difficult to make. Basically, in cherry season, pit, gently poach in sugar syrup on very low for 30 minutes to 1 hour or so. Let rest in syrup over night. Repeat – maybe only 15 to 20 minutes this time. Add a few drops of almond extract or Maraschino liqueur to syrup. Can in syrup for long term storage. Or keep in fridge for short term storage.

    At this time of the year, I would suggest to rehydrate dry cherries, or to use cranberries (fresh or dry).

  • Have you any hints for making this in a convection oven? I do the baking for my son’s coffee shop and want to use this recipe there, where the only oven is a convection one. Thanks.

  • Hello, Eileen: I am not sure it would be that different! My understanding is that convection oven cook a little faster (or same length of time but at a somewhat lower temperature) by really moving air around. See: This pineapple upside down cake is moist and will tolerate some temperature range. This is not a souffle! I would either follow the recipe once, testing for doneness earlier – maybe at the 45 minute mark? then adjusting based on the specific oven result the 2nd time. I otherwise assume that you bake other recipes in that convection oven? How did you adapt them? I would follow the same adaptation guidelines. Also, Don’t forget the oven manufacturer as a resource, either through their web site (where manuals are often on-line) or by calling them. Finally, there is always this calculator (use it at your own risks!):

    If you do try the cake, I would love to hear about how it turns out and how your customers receive it. Please: tell us!

    I am on my way out of the door to bake one myself for the monthly County Volunteer Fire & Rescue Association’s dinner which is held at our Firehall this month.

    Thanks for stopping by.

  • Hi Sylvie. We are having a shindig for about 30 for my partner’s 50th birthday this Saturday. This looks like what I’ve been searching for! My question is, where does one find a 13×19′ pan? Thank you! Ken

  • In one’s cupboard? All kidding aside, any kitchen store or old-fashioned hardware store should have something that works. I sometime use a large Pyrex dish or a doubled-up disposable alum pan (sold as caterer’s pan). While called “disposable” they are also fully “reusable”… for future cakes.
    Have fun! Happy celebration.

  • Thank you for your recipe…my sisters and I grew up making pineapple upside down cakes. My question is related to timing and storing. For a Saturday evening wedding, can I make these on Friday and leave them at room temperature? We are looking at spring and I don’t think hot weather will be an issue.

  • Linda, you will have to use your judgment and personal comfort level. But I can tell you that I do it all the time (as long as the temperature is moderate) as the cake does not get eaten entirely the day it is made. Also I have made it well ahead (several weeks) and froze it. The trick is to make sure the top (pineapple.butter/sugar) is frozen before you wrap the cake. Best wishes

  • Thank you Sylvie…I plan on trying this out several times before hand…much to my friends’ and coworkers’ delight!

  • Ann – absolutely! In fact the original recipe published in Saveur magazine (that I referenced in the post) was for an 8 x 8″ cake — which is WAY too small. happy baking!

  • The recipe is for a 19″x13″ pan. Do you have a pan twice that big? 19″ by 26″? I have never baked the cake in anything bigger than a 19×13, so I really don’t know:: why don’t you try and tell us? On the other hand if you want to double the batter and then pour it in 2 pans, each 19×13, then by all means… as long as your bowls are big enough to handle that much batter. Personally, I prefer to make multiple batches at once, using multiple bowls, so I end up with several bowls of batter, each ready for a 19×13 pans.

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