Pineapple Upside-Down Cake

Pineapple Upside-Down Cake
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pineapple upside-down cake
Let them eat cake!

We haven’t had a pineapple upside-down cake in years — well, maybe even decades — something we thought should be rectified with the recent arrival of fresh, ripe pineapple. You didn’t think we’d make pineapple upside-down cake with pineapple from a can, did you? The last time we ate some pineapple from a can, we couldn’t believe how bland and flavorless it was. No way is that going into our cake. And it shouldn’t go into yours, either.

Whenever we’re thinking of something we’ve not made before and for which we don’t have a recipe, we turn to The Joy of Cooking, by Irma S. Rombauer and Marion Rombauer Becker; it flat has recipes for almost everything. Once again, Joy saved us, although it did call for that canned “pineapple” we discussed earlier. We ignored that part.

We will say that when we first read this recipe, we were a bit daunted. It seemed difficult, with lots of bowls for this and that. Sifting here and there. Folding, folding, folding of ingredients. But, after a careful reading, we thought, “Hey, we can scratch this!” And you can, too. Trust us, and just follow along step by step. Warning: there is a lot of folding of ingredients.

Pineapple Upside-Down Cake

Yield: 1 cake (9-inch)

Pineapple Upside-Down Cake


  • 1 fresh pineapple
  • 6 Tbs unsalted butter
  • 3/4 cup (150g) brown sugar, packed
  • 1 dry pint raspberries (optional)
  • 1 cup (125g) cake flour
  • 1 tsp baking powder
  • 4 eggs, separated
  • 1 Tbs unsalted butter, melted
  • 1 tsp vanilla extract
  • Pinch cream of tartar (optional)
  • 1 cup (200 g) sugar

Abbreviated Instructions

Peel, slice, and core pineapple. Arrange slices in the bottom of a large (9-10 inch) skillet.

Add butter and brown sugar and place over low heat. Increase heat to medium as sugar dissolves and the pineapple releases its juices. Cook until liquid has the consistency of light syrup, about 20 minutes. Remove from heat.

Preheat oven to 350°F. Move a rack to the center of the oven.

Place raspberries, if using, in gaps between pineapple pieces. Set aside.

In a small bowl, sift together cake flour and baking powder. Set aside.

In another bowl, whisk egg yolks, vanilla, and the tablespoon of melted butter. Set aside.

In the bowl of a stand mixer fitted with the whisk attachment, beat egg whites and cream of tartar until stiff but not dry.

Fold sugar into whites, 1 tablespoon at a time. Fold egg yolk mixture into the whites. Fold in the flour mixture in four equal amounts.

Pour batter into skillet, covering the pineapple and sauce.

Bake 30 to 40 minutes, or until a skewer inserted into the center comes out dry.

Immediately invert cake onto a plate. Leave skillet in place for 5 minutes to allow the sauce to seep into the cake before removing.

Ingredient discussion:

Everything is better when you use fresh fruit, so, while pineapples are coming in fresh, go grab one for making this cake. It’s not that difficult to peel, slice and core a pineapple; just make sure you have a sharp knife. Unsalted butter is the only way to go for baking. It allows you, the chef, to choose the salt level you want, not the level of salt that someone else wants. You’ll note that we list a few things by weight. These, if you have a scale, will make you life easier: pour flour right into the sifter set over a bowl, measure brown sugar without packing, etc. The pinch of cream of tartar is to help stabilize the egg whites while whipping.

separated eggs
To save a bit on clean-up, separate the egg yolks into a small bowl and the whites into the mixer bowl.

Lastly, remember to separate your eggs while cold, then let the whites and yolks come to room temperature (about 30 minutes should do it). Ideally, when you separate them, place the yolks in a small bowl (big enough so you can still whisk them later) and the whites into the (scrupulously clean) bowl of a stand mixer.

Procedure in detail:

slicing pineapple
It’s really not too difficult to prep a pineapple. Just use a sharp knife.

Peel, slice, and core. Get out a large, sharp, chef’s knife and slice the top off the pineapple. Stand the pineapple on end and cut off the skin. Now go around the outside and trim out the eyes. Finally, slice off the bottom. You’ve peeled a pineapple. Yay! Now cut it into slices about 1/3 of an inch thick, cut each slice  into quarters, and trim away the core. Done. Not too bad, right? Taste. Very good, right?

Layer. Place the pineapple pieces in the bottom of a heavy oven-proof skillet (cast iron is ideal), fitting them in as tightly as you can. You may not use them all, or you may be able to sneak in a few more pieces as they cook and shrink. Otherwise, just munch on the remaining pieces and say you’re taste-testing to determine the exact amount of brown sugar needed.

cooking pineapple
Pineapple, butter, and brown sugar is all you need for a nice topping (bottoming?) for a cake.

Add butter and brown sugar. Place the butter on top of the pineapples pieces, followed by the brown sugar. If you have a very sweet pineapple, feel free to reduce the amount of brown sugar. Not so sweet, increase the amount of brown sugar. See, all that tasting paid off!

cooking pineapples
Cook the pineapple, butter, and sugar until nice and bubbly and syrupy.

Cook pineapple. Set the skillet over medium-low heat until the butter melts, the sugar is mostly dissolved and the pineapple is releasing its juices. Increase heat to medium and let simmer until the sauce thickens to the consistency of a light syrup (like maple syrup). If you have a thermometer, the temperature of the syrup will be around 118°F. Remove from heat.

Preheat oven to 350°F. Move a rack to the center of the oven.

adding raspberries
As the syrup cools, feel free to place a few accent bits of fruit in between the pineapple pieces. In this case, we used raspberries.

Place raspberries. If using, place raspberries in the gaps between the pineapple pieces. You’ll probably need just about a dry pint (6 oz). If you wish, you can use other types of fruit. We would avoid using maraschino cherries as they don’t taste like anything but syrup. Set aside.

sifting flour
Measure the flour right into the sifter along with the baking powder and sift.

Sift flour. Yes, break out the sifter from the back of the cupboard. Place the sifter in a medium bowl and put the cake flour into the sifter, followed by the baking powder. Then sift away. Set aside.

whisked egg yolks
Quickly whisk the egg yolks with the melted butter and vanilla extract (pure, natch).

Beat egg yolks. In a small bowl, use a whisk and beat the egg yolks with the vanilla and melted butter until uniform in color. A minute of whisking will be more than enough. Set aside the yolk mixture.

Measure sugar. If you haven’t done so already, measure out that cup of granulated sugar. Just leave it in a measuring cup until you need it.

whipped egg whites
The whites should look moist, but the peaks should be stiff and not slump over.

Whip egg whites. Place the egg whites and a pinch of cream of tartar into the bowl of a stand mixer fitted with the whisk attachment. Start the mixer on low, and, as the egg whites become frothy, increase the speed of the mixer, working up to full power. Whip until the whites are stiff, but still moist-looking. To check, just stop the mixer and lift up the whisk to see if the egg white peaks stay peaked.

folding in sugar
It seems like a lot of effort to fold in the sugar a tablespoon at a time, but it only takes a few minutes.
Once the sugar is folded in, you’ll have a meringue with the consistency of light marshmallow fluff.

Fold in sugar. Fold, fold, fold. And fold some more. This seems like overkill, but it’s not. What you need to do is to add that cup of sugar into the whites without the egg whites collapsing. The way to do that is to fold in the sugar a tablespoon at a time. Yes, one tablespoon of sugar sprinkled on top, then folded in. Then another tablespoon of sugar, more folding. The folding stage goes pretty quickly, so this really is easier than it sounds. All that folding allows the sugar to dissolve into the egg whites and not collapse them. By the time you get to the end, your egg whites will have the consistency of a light marshmallow fluff.

adding egg yolks
Ah, much faster to fold in the egg yolk mixture.

Fold in egg yolks. Compared to the last step, this is easy and fast. Pour the egg yolk mixture over the egg whites and fold it in until uniform in color. Remember to scrape the bottom of the bowl, as unmixed ingredients tend to lurk there.

folding in flour
As with the sugar, fold in the flour in multiple additions, in this case four. All this folding makes for a light cake.

Fold in flour. Yes, more folding. Fold in the flour mixture in four equal amounts. While folding, watch for those pockets of flour that seem to hide in the batter. Once you’ve folded in the flour, the batter is ready.

pineapple upside-down cake ready for baking
Pour the batter over the pineapple and sauce, then bake.

Pour over pineapple. Pour the batter over the pineapple and sauce in the skillet, making sure to cover everything.

baked pineapple upside-down cake
The cake will be light brown, spring back to the touch, and a skewer in the center will come out clean.

Bake. Slide the cake into the oven and bake 30 to 40 minutes, or until the cake is light brown, springs back when you touch it, and a skewer inserted into the center comes out clean.

Invert. Immediately upon removing the cake from the oven, place a large serving plate over the top, and, in one motion (using hot pads, of course), lift up the cake and platter and flip over. Let it rest upside down for 5 minutes so the caramel sauce seeps into the cake before removing the skillet.

pineapple upside-down cake
Flip, and let cool before serving.

Cool. Let cake cool completely before slicing.

 When you read the instructions, this cake may seem daunting, especially all that folding, but, really, it’s not all that difficult. Plus, it makes a nice moist cake that will please everyone who likes pineapple. The cake is exceptionally light and tasty. We were worried that it might be dry, but with that caramel sauce soaked into the cake, our worries were unfounded. Instead, it was nice and moist, and, by using fresh pineapple, it had a lot of fruit flavor. Three stars because of the amount of folding required, but five stars for tastiness, which averages out to four stars!
Worth the trouble?

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