Old-Fashioned Pineapple Upside Down Cake
Old-Fashioned Pineapple Upside Down Cake

Despite the fact that I love pineapple so much and have promised several times on this site to include it more regularly it's been a while since anything pineapple has shown it's sweet little chunks on these pages and for that I really have no excuse or explanation, but at last I've buckled down and made good on the promise and this wonderful, wonderful Old-Fashioned Pineapple Upside Down Cake will not disappoint!!

Making a pineapple upside down cake has been one of my goals for years but somehow I always talked myself out of trying it, feeling a little intimidated by the upside-downess of it all! Well folks, I'm here as a cautionary tale--DON'T BE LIKE ME!! For such a pretty and complicated looking cake, it isn't hard and un-molds like a dream. If, like me, you harbor anxiety towards the aforementioned tropical topsy-turvy confection, this is the one to try!

So, first you make a buttery, vanilla-enhanced caramel sauce and then coat the fresh pineapple in it, cooking it together until the pineapple begins to break down and releases its own sugary juices into that delightful caramel sauce.

Next you transfer the entire thing to a buttered cake pan, entirely covering the bottom with all that sticky pineapple and pineapple goo!!

Finally, you make a very easy butter cake batter, pour it on top of the pineapple and bake the whole thing for about an hour.

Once the cake cools, you hold your breath, invert onto a plate and voila! Upside down perfection!

The bottom of the cake is now the top and what a top it is--thick, sweet slices of caramelized pineapple that literally melt in your mouth. And the cake-- it's buttery, moist and deliciously infused by the caramel sauce. So simple and yet so full of a rich and complex flavor!

Each bite is a luscious blend of fruit and cake that's so homey and so comforting. One taste and you can instantly see why it's a classic--and just because I can cross this off my bucket list, doesn't mean I can't make this again...and again, right? Who's making up the rules, anyway?!!

Old-Fashioned Pineapple Upside Down Cake

Serves 8-10 
Prep Time:  40 minutes; Bake Time:  About 1 hour


  • 1 fresh pineapple, peeled, halved, cored and cut into 3/4 inch slices
  • 1 3/4 cups sugar
  • 1/2 cup water
  • 6 tablespoons unsalted butter, softened, plus 1 stick butter (1/2 cup) melted and cooled, plus additional butter for greasing the pan
  • 1 cup unbleached, all-purpose flour
  • 1 teaspoon baking powder
  • 1/4 teaspoon kosher salt
  • 2 large eggs, room temperature
  • 3 egg yolks, room temperature
  • 1 teaspoon vanilla extract

The Recipe

1.  Cut the pineapple slices in half and set aside.

2.  Into a medium saucepan, place 3/4 cup of the sugar. Add the water and swirl the pan to mix together the water and sugar, using your finger to make sure all the sugar is moistened by the water and that none is stuck to the bottom or sides of the pan. Turn the heat to high and cook the sugar water, not stirring it at all, allowing the mixture to come to a rolling boil. Boil for another 3-4 minutes, not stirring or moving the pan at all, until the mixture begins to caramelize and thicken--you'll notice the mixture will start off boiling rapidly but as it thickens will start to boil more slowly and some of the syrup will start to change color, especially around the edges.

3.  As soon as the mixture starts to change color, gently swirl the pan in a circular motion so the sugar gets evenly caramelized. Keep swirling until the caramel turns a medium golden brown and then lower the heat to low immediately. Carefully whisk in the 6 tablespoons of softened butter--it may bubble up and sputter. Then add in the pineapple and stir until it's coated with the caramel sauce. If some of the caramel hardens and sticks to the pan, don't worry--it will melt again as you continue to cook this. Turn up the heat to medium-high and bring to a boil. Once the mixture is boiling, turn the heat down to medium-low and simmer for 10-12 minutes, or until the pineapple turns golden brown and starts to release its juices into the caramel. Using a fork, transfer the pineapple to a plate and set aside. Turn the heat up to medium-high and boil the caramel sauce for another 2-3 minutes, or until the mixture turns thick and syrupy.

4.  Make sure the rack is in the center of the oven and preheat it to 350ºF. Very generously butter a 9-inch round cake pan.

5.  Place the pineapple into the pan in concentric circles, completely covering the bottom of the pan with the pineapple, cutting any pieces smaller in order to fill any gaps. If you need to, you can double the layer of pineapple a bit. Now pour the caramel syrup over it all and set the pan aside.

6.  Sift the flour, baking powder and salt together into a medium bowl. In a large bowl, place the eggs and egg yolks and whisk them together until well blended. Slowly whisk in the remaining 1 cup of sugar, the vanilla and then the melted and cooled butter. Fold in the flour mixture gently, using a rubber spatula, until the egg mixture and flour mixture are well combined.

7.  Pour the batter evenly over the pineapple in the pan, rapping the pan gently on the counter to remove any air bubbles and making sure that the batter fills in any of the crevices between the pineapple slices. Bake for 50-60 minutes, until the top of the cake looks golden brown and springs back when you press the middle with your finger. Let the cake cool in the pan on a rack for 30 minutes.

8.  Place a large rimmed plate on top of the cake pan and carefully turn the whole thing upside down. Lift off the cake pan. If any of the pineapple has stuck to the pan, remove and place it where it fits on the cake. Let the cake cool for at least another 30 minutes. You can serve this warm or at room temperature.

9.  Cake keeps covered at room temperature for up to 2 days and leftovers can be stored in an airtight container in the fridge for up to 5 days.


Note:  Recipe adapted from Flour by Joanne Chang. This recipe is perfect--I didn't change a thing!!




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