Upside Down Pineapple Cupcakes

If you follow me on Twitter then you have been reading all my teasers about these cupcakes.  Well the waiting is over and they have arrived!!! All in their finest. I may be a bit biased as they have Plaid cupcake papers, but I think these are some fine looking pastries! Cupcakes are an all time favorite.  So when you think of creating something new and fun, traditional cupcakes might not come to mind.  I can tell you though these are no traditional cupcakes you see before you.  These cupcakes are all ready for summer!

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I don’t know about you but I think these cupcakes are just about the most amazing morsels of all the summertime flavor favorites.  Everyone has a grandmother that makes Upside Down Pineapple Cakes.  They are dripping in brown sugar and pineapple wonderfulness.  All those wonderful memories are captured in this cupcake.  Dense sweet cake topped with pineapple buttercream and pineapple chunks cooked in a brown sugar butter glaze, all topped with that beauty of a Cherry!

Although this is not a sponsored post I do have to give a shout out to my friends at Dole Foods!  They had one of the best booths at BlogHer Food and I have to admit I went back more than once for Chocolate covered frozen bananas!!! Since they were so sweet and had such a nice booth I made sure to purchase Dole Pineapple Chunks.  {The Tid-bits were not available in my store.}  They truly are a superior fruit company and using quality ingredients is very important to me here at the P and P Kitchen.

These cupcakes are very easy to make and they have a really great “Wow!” factor if you need a fun dessert to show off with.  Throw a Luau style party if you have to, just to make these cupcakes.  I am really really happy with the results! Whenever I am developing a new recipe I always have my fingers and toes crossed hoping that they will be a success. And I can proudly say that these are fabulous!  The frosting and the pineapple glaze are really the showstoppers of these cupcakes.  Brown Sugar, butter, pineapple…… totally in love!

So run out to the store and Pick up some Dole Pineapple and get to baking! You will have an amazing crowd pleasing cupcake at your hands!


  • For the cupcakes
  • 1 20oz can of pineapple chunks and reserved juice
  • 1 box mix of yellow cake
  • 1/3 cup oil
  • 1/4 cup pineapple juice
  • 3/4 cup water
  • 2 eggs
  • 3 tbs brown sugar
  • for the frosting
  • 4 cups powdered sugar
  • 1 cup (2 sticks) Butter
  • 2 tbsp pineapple juice
  • 1 tsp vanilla
  • for the glaze
  • 3 tbsp butter
  • 1/4 cup brown sugar packed
  • 3 tbsp pineapple juice
  • 1/2 of the can of pineapple chunks {I snacked on the other half}
  • maraschino cherries well drained for garnish


  • Cupcakes:
  • preheat oven to 350
  • line 18 cupcake liners in muffin tin
  • in a mixing bowl combine all the ingredients for the cupcakes except the brown sugar and mix
  • add the brown sugar and swirl through the batter making rings
  • fill each cupcake liner 2/3 full
  • bake for 20 min
  • let cool completely before frosting
  • Frosting:
  • in a mixer with the paddle attachment
  • cream the sticks of butter and powdered sugar
  • add the pineapple juice and vanilla
  • add more pineapple juice if needed for consistency
  • beat for 5-10 min for completely smooth frosting
  • Pipe or spread on cooled cupcakes
  • Glaze:
  • in a saucepan melt the butter and brown sugar
  • add the pineapple juice and fruit chunks
  • cook over medium heat for 5-7 min until the sugar starts to caramelize and the pineapples get a nice golden color
  • let cool completely {Do Not Put in fridge to speed up cooling this will cause the butter to solidify again}
  • place completely room temp pineapples on each cupcake and drizzle some of the glaze on each
  • top with a cherry
  • Enjoy!
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