Pineapple Upside Down Cup Cakes

While I was shopping for the ingredients for the Peanut Butter Brownies, I got to thinking about someother favorite deserts and realized I only need a few cherries and some pineapple slices to create this one in the same afternoon.  To further justify making this dessert, it is one of my personal favorites and the next day I would be going to a memorial day pool party and this seemed like the perfect treat to share.  And its because we would be sharing I turned this into cupcakes instead of baking in a large pan – although I did make a little extra batter and put an 8×8 cake in the oven as well to share with the team at work – and this works just as well in a larger pan as they do as cup cakes.

If you do choose to make a larger cake, feel free to ignore the icing.  In my world, cupcakes need icing but a normal pineapple upside down cake does not.  It certianly won’t hurt the cake but the rum, butter and sugar topping is more than enough sweet for the larger presentation.



Pineapple Upside Down Cup Cakes

I firmly believe this is a perfect desert – the cake is light and airy, topping gives a bit of crunch and sweet and the acidity from the pineapple with hints of rum throughout hit all of the right notes.





1 stick unsalted butter

1 cup brown sugar

2 TBs Dark Rum 



1 stick of softened butter

1 cup sugar

1 1/2 cups flour

2 Teaspoons baking powder

Pinch of salt

2 large eggs

1 TBs Vanilla

2 TBs Dark Rum

1/2 cup Pineapple Juice



1 stick softened butter

3 Tbs pineapple juice – reserved from slices

2 TBs plus Pineapple Rum

3 1/2 cups powdered sugar



Maraschino Cherries with stem


Equipment Required

Cupcake baking sheet

Measuring utensils





Piping bag or large Ziplock plastic bag




Preheat oven to 350 degrees

Topping –

Melt butter in small skillet over medium heat.  When melted, add sugar and rum and stir until fully incorporated.  This mix will bubble but don’t let it get too hot and turn to carmel or worse…Heat may need to be adjusted to low as this process should take around 5 minutes to ensure a smooth topping.  Once mix is dark in color and takes on a shiny smooth texture, remove from heat and allow to cool slightly.

Batter –

Begin by beating butter and sugar with paddle attachement until mix is light and fluffy.  Add eggs one at a time – adding the next after each is fully incorporated.  Next, add Vanilla, Rum and Pineapple juice and mix well.  Lastly, sift flour, salt and baking powder together and slowly add this mixture to the mixer.  Once all has been incorporated, if the mixture appears a bit thick – i.e. thicker than pancake batter – it can be thinned by adding a bit more rum or pineapple juice, which ever you prefer.  (I added more rum.)  The batter may look a bit chunky or curdled because of the pineapple juice – don’t worry, this is normal.

To assemble and bake –

Place 2 teaspoons of sugar topping mixture into each cup cake hole on the baking sheet.  Next, cut 1/4 out of your pineapple slices and place the 3/4 remaining ring, in a ring shape, in the hole on this topping.  Finally, place batter ontop of topping and pineapple mixture, leaving about 1/4 of the cup cake mold not filled with batter as these will rise slighty during baking.

Bake cup cakes for 25 – 30 minutes.  (I recommend putting a bit of foil under the baking pan as the sugar mixture may bubble and boil over the sides of the pan.)  Remove from the oven with nicely browned on top to a rich golden hue.

Let rest for about 10 minutes then turn pan over onto a large serving dish or half bake sheet to allow topping to melt down the sides of each cupcake.  Let these cool to room temperature.


Icing –

This is an easy one – place all ingredients in mixing bowl with wire whip attachement and mix well.  We are looking for a very smooth consistency with this icing.  As all ingredients incorporate, if the icing seems a bit “chunky”, just keep adding rum until it is a firm but smooth texture.



To Finish –

Arrange cupcakes on a serving tray and pipe a bit of icing in the middle of each cup cake.  Top with a cherry and enjoy!

*Personal Recipe Disclaimer – I think its important to give credit when it is due.  While I test, tweak and refine all recipes before I post to ensure I think it’s the best version, there is almost always inspiration or a base recipe from a cookbook, family/friends or from the internet used as an initial guide.  Even though I work as a “chef”, one of the chefs greatest tools for inspiration are other chefs and cooks creating and posting wonderful ideas.  Thanks to all of you out there for the inspiration and for those that give this a try, I hope you enjoy my version.  

Recipes cited to create this one:

For the batter –

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