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Pineapple Upside Down Cake

April 2, 2013

Pinapple Upside Down Cake 026

This is by far the most delicious Pineapple Upside Down Cake I have made.

For a good part of last summer I made several Pineapple Upside Down Cakes and was not overly pleased with anyone of them, even one that my mother had made on a regular basis.  I don’t know exactly what happened to my taste buds over the years but they were not likin’ what I was makin’.  Then miraculously in the September Bon Appetit  issue, they had a Pineapple Upside Down cake that looked amazing!   How did they know that I was on a quest to find a good recipe?  So I made it for a dinner party last fall and I haven’t looked back.

I follow the recipe from Bon Appetit exact but I am including the recipe, notes and pictures here to help you along.  I think the fresh pineapple and the dark brown sugar is what really sets this recipe apart from all others.

The only thing that you absolutely need is a 10 inch cake pan with 2 inch sides.  Not something you always have in your cupboard but a must for this recipe.  It is a large cake.

Pineapple Upside Down Cake ( by Bon Appetit Pineapple Upside Down Cake)

for the Caramel:

1-1/4 cups packed dark brown sugar

1/2 cup (1 stick/4 ounces) butter, cut up into small pieces

1/4 cup bourbon (I used Evan Williams Kentucky Straight Bourbon Whiskey: this was the smallest bottle available for a reasonable price.  We are not bourbon drinkers but if you are use the best that you have!

for the Cake:

1 medium pineapple

1-2/3 cups cake flour (the recipe on-line says 1-1/3 cups but the magazine recipe, stated here, is the amount I used)

2 teaspoons baking powder

1 teaspoon kosher salt

1/8 teaspoon ground cardamom

1 cup sugar

1/2 cup (1 stick/4 ounces) butter, softened and cut up

2 teaspoons vanilla

2 large eggs

1 cup sour cream


Coat cake pan with canola oil spray and set aside.  Put brown sugar and butter in a medium saucepan, over medium heat and cook, whisking frequently, until mixture is bubbling and sugar is completely dissolved.  Boil, whisking frequently, until caramel thickens, and pulls away from the sides of the pan, about 3 minutes.

Remove from the heat and add bourbon.  Mixture will boil up so be careful.  Put pan with caramel back on medium heat and return caramel to a boil, stirring frequently.  Cook for 1 minute.  Pour caramel into prepared cake pan and swirl pan until bottom is completely covered with caramel.

Preheat oven to 350 degrees.


Cut top and bottom off of pineapple.  Using a sharp knife, cut skin off a section at a time, removing as much of the brown eyes as possible.  Cut 1/4 inch thick slices of pineapple.  Using a very sharp paring knife, trim slices into a nice round and cut out the core with the tip of the knife.  OR if you are lucky enough to have this handy Donut Cutter like I did (thoughtfully given to me by my daughter) position the middle part of the cutter over the core and press down firmly over the slice of pineapple.  It works absolutely perfectly!  By this time the caramel should be at room temperature.  Arrange pineapple rings decoratively on top of caramel in cake pan.  Do not overlap.  Cut rings into smaller pieces to fill in any gaps, if you like.


Place flour, baking powder, salt and cardamom into a medium sieve that has been placed over a medium bowl.  Sift flour mixture into bowl underneath, using a whisk.  Combine eggs and vanilla in a medium bowl.  Put butter in bowl of your electric mixer and start beating.  Measure out sugar and set sour cream aside.  Add sugar to butter and beat for 5  minutes until light and fluffy.  Scrape down sides and bottom of bowl.  Beat for another 1 minute.  Add egg mixture and beat for 2 minutes until light and fluffy.  Scrape down sides and bottom of bowl and beat for another 1 minute.

Add flour mixture alternately with sour cream, ending with sour cream.  Mix until just combined.  Scrape sides and bottom of bowl and beat for another 30 seconds.  Pour batter into prepared pan and smooth top.

Bake cake for 50 – 60 minutes.  50 minutes worked for me.  When testing the cake with a toothpick, do not insert all the way down into the cake.  Only insert about 1/2 way down into the cake.  Otherwise you will insert the toothpick into the pineapple and caramel, the toothpick will come out moist and you will think that the cake is not done.  The cake will also pull away from the sides of the pan slightly when done.  Transfer cake to a wire rack and let cool for 30 minutes.

Run a sharp knife around sides of pan to loosen cake and invert cake, carefully,  onto a large plate.

Cake can be made 8 hours ahead.  Cover with a cake dome and let stand at room temperature.   I did this when I had my dinner party and it worked out really well.  Serve with whipped cream!

butter and brown sugar for caramel:

Pinapple Upside Down Cake 001


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caramel boiling:

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caramel in the cake pan:

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cut top and bottom off of pineapple:

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cutting skin off:

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slicing pineapple:

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using the donut cutter:

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using the paring knife method:

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finished rings of pineapple:

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pineapple slices onto caramel:

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cake: mise en place

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finished batter:

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into the pan:

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cake out of oven:

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cake out of pan:

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