Something has always intrigued me about pineapple upside-down cake. Much like an apple tartin there is the promise of luscious fruit coated in a gooey caramel like substance supported by pastry to help soak it up. Yet with the pineapple upside-down cake, there is the pineapple - a fruit I love in all forms from raw to cooked to in my drinks and then there is the cake in contrast to the thin more pie-crust like underpinning to the apple tartin which looks perfect to soak up the pineapple juices and offer some balance. 

At the same time, photos of pineapple upside-down cakes have never impressed me, often dotted with maraschino cherries, looking dated and generally unappealing.

The other week I was flipping through cookbooks looking for an unusual cake to bake for a friend's birthday. And I came across this gorgeous photo in my Flour Bakery cookbook. I knew I had finally found a pineapple upside-down cake I wanted to try. I ended up making another cake for my friend which requires another attempt before I can share with you. 

Last week I managed to find a reasonably ripe pineapple and snagged with the joyful anticipation that I could make this cake over the weekend. 

I was nervous about the recipe as after the pineapple is cut, it requires making a caramel from scratch which sounds daunting. Every time I see someone make on on a cooking show they seem to burn it and need to start all over. I have made caramel before, but more of a cheaters version employing condensed milk but it was easy and yielded perfect caramel for dipping apples into. But while wordy and seemingly complex, the detail and specificity actually makes the recipe easy to master. I kept my phone handy to use as a timer for each timed phase, as timing is important. The results were perfect. 

I was beyond delighted with how the cake turned out. The pineapple was tender, yet not mushy, the caramel sweet and gooey coating the pineapple and seeping into the cake; the cake was buttery and tender, soft yet with an ever so slight crispy cut on the very bottom. In addition to tasting wonderful the cake had a wonderful mouth feel. Next time I make it I might sneak a pinch of salt and/or a splash of coconut rum in the caramel before pouring it over the pineapple. 

You should most definitely make this cake. 

Old-Fashioned Pineapple Upside-Down Cake 

From Flour: Spectacular Recipes from Boston's Four Bakery + Cafe (with some extra notes from us)

Makes one 9" cake (Serves 10) 


1 pineapple 
1 3/4 cups (350 grams) sugar
1/2 cup (120 grams) water
6 Tablespoons (3/4 stick/86 grams) softened unsalted butter
1/2 cup (1 stick/114 grams), melted and cooled butter
1 cup (140 grams) unbleached all-purpose flour
1 teaspoon baking powder
1/4 teaspoon salt
2 eggs, at room temperature
3 egg yolks, at room temperature
1 teaspoon vanilla extract 


Using a serrated knife, peel, halve and core the pineapple, then cut into 3/4-inch-thick slices (so you get rounds). Cut the slices in half (or leave as half circles if you prefer) . Note to core the pineapple: cut it in half lengthwise and then cut a "v" in the center around the core to remove it. 

Put 3/4 cup (150 grams) of the sugar in the bottom of a medium saucepan. Add the water and gently swirl pan to moisten the sugar; if necessary, poke your fingers around the bottom of the pan to make sure all of the sugar is moistened. (Note: there is no flame yet) Place the pan over high heat and leave it undisturbed until the contents come to a rolling boil. Then continue to boil rapidly without moving the pan until the sugar syrup starts to caramelize. This will take 3 to 4 minutes: the sugar syrup will boil furiously; then as it thickens, it will boil more languidly; and then you will see some of the syrup start to color and darken around the edge of the pan. 

When you see color in the pan, gently swirl the pan in a circular motion so the sugar caramelized evenly, and then keep swirling gently until the caramel is a medium golden brown. Turn down the heat to low and whisk in the 6 tablespoons of room temperature butter; be careful, as the caramel may sputter and steam. You do not want to come in contact with the mixture as it is very hot. Carefully add the pineapple and stir until it is coated with the caramel (you can use a fork to place the pineapple in the pan and to turn the pieces over to coat vs stirring). Don't worry if some of the caramel hardens; it will re-liquify as it continues to cook. Turn up the heat to a medium-high and bring to a boil. Then turn down the heat to a medium-low and simmer for 8 to 12 minutes, or until the pineapple turns golden brown. The pineapple will release juice and liquify the caramel. Using a fork, transfer the pineapple to a plate. Continue to boil the remaining liquid on medium-high heat for 2 to 3 minutes, or until thick and syrupy. 

Position rack int he center of the oven, and heat the oven to 350°F. Generously butter a 9-inch round cake pan.

Add all of the pineapple and the caramel syrup to the prepared pan, arranging the pineapple in concentric circles and covering as much of the bottom of the pan as possible. Cut the pineapple pieces smaller to fill in any gaps, and double layer the pineapple if there is extra. 

In a medium bowl, sift together the flour, baking powder and salt. In a large bowl (or stand mixer), which together eggs and egg yolks until blended, then slowly whisk in the remaining 1 cup (200 grams) sugar, the vanilla, and the 1/2 cup melted butter. Using a rubber spatula, fold the flour mixture into the egg mixture just until well combined. 

Pour the batter evenly over the pineapple in the cake pan. Tap the pan gently on a countertop to get rid of any air bubbles in the batter and to make sure the batter fills in any crevices in the pineapple and settles into the bottom of the pan. 

Bake for 50 - 60 minutes, or until the top is golden brown and springs back when pressed in the middle with a fingertip. Let cook in the pan on a wire rack for about 30 minutes, or until cool enough to handle. 

Place a serving plate upside down on top of the cake pan, then holding the pan and the plate tightly together, carefully invert them. Life the cake pan. If some of the pineapple sticks to the pan, remove it and replace it in is place on top of the cake. Let the cake cool for at least another 30 minutes, then serve warm or at room temperature. 

The cake can be stored in an airtight container at room temperature for up to 2 days.