Pineapple Upside Down Cupcakes

pineapple upside down cupcakes

I am constantly inspired by everything around me but more than anything, I am inspired by my heritage and family traditions.  Pineapple upside down cake is such a classic Southern dish that was served countless times in my house.  It was only natural that I would see fit to create these pineapple upside down cupcakes.  I was always so mesmerized by the creation of this dessert as a child.  I would watch the cake bake in the oven not knowing the unique surprise beneath that awaited me.

pineapple upside down cupcakes
When my mom flipped the cake over to reveal the gorgeous decorative pineapple and cherry topping, I would stare in awe.  The cake just seemed so special, so sacred.  
pineapple upside down cupcakes

Sometimes playing around with sacred childhood memories can be dangerous but I always loved taking the recipes I grew up with and making them my own, which now brings me to these little lovelies, my pineapple upside down cupcakes.  They are seriously the perfect cupcake.  

pineapple upside down cupcakes

The base is a moist sour cream cake mildly flavored with rum to give it an extra kick.  Topping it with a pineapple buttercream made it even better but the real surprise is what is underneath.  Little small chunks of pineapple ready to eat with every bite.  

Now don’t you want some of that? 
pineapple upside down cupcakes

Pineapple Upside Down Cupcakes

Yield: Makes 24 cupcakes

Pineapple Upside Down Cupcakes


  • 1 stick unsalted butter, softened
  • 1 cup granulated sugar
  • 3 large eggs
  • 1 tablespoon oil
  • 1 1/2 cup cake flour
  • 1/4 teaspoon salt
  • 1/4 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/2 cup sour cream
  • 2 teaspoons vanilla extract
  • 1 teaspoon rum
  • 1 cup brown sugar
  • 1 can (8.25 ounces) pineapple bits, drained (save the juice) or fresh pineapple if in season
  • 1 stick melted butter
  • 1 stick unsalted butter, softened
  • 4 ounces cream cheese, softened
  • 2 cups confectioner's sugar
  • 2 tablespoons crushed pineapple
  • 1 teaspoon vanilla extract
  • 1-2 tablespoon pineapple juice


  1. Preheat oven to 350 degrees.
  2. For the cake batter, add butter and sugar to bowl of a mixer and beat on medium high until well incorporated and light and fluffy (about 4-5 minutes).
  3. Next add in eggs one at a time then oil and beat until well mixed.
  4. Sift together cake flour, salt, baking powder, and baking soda.
  5. In a separate bowl, add sour cream, vanilla extract, and rum.
  6. Alternate flour mixture and sour cream mixtures to mixer, ending with the flour mixture, and beat each addition until batter is well mixed without overmixing.
  7. To assemble cupcakes, Line muffin/cupcake pans with cupcake liners.
  8. Spoon 1 teaspoon of melted butter into the bottom of each liner.
  9. Top the butter with 1 teaspoon of brown sugar.
  10. Then spoon 1 teaspoon of crushed pineapple over the brown sugar and spread out on the bottom of the liner.
  11. Next using a ice cream scooper, add cake batter to each cupcake liner over the crushed pineapple. The liner should be filled about 3 quarters of the way.
  12. Bake for 20-24 minutes or until a toothpick inserted into the center of the cupcakes comes out clean.
  13. Allow the cupcakes to cool in the pans for 10 minutes then remove the cupcakes from the pans and place them on a cooling rack to cool completely.
  14. While cupcakes cool, add butter, cream cheese and confectioners sugar to bowl of a mixer and mix on high for 2 minutes.
  15. Next add crushed pineapple, vanilla extract and pineapple juice in small amounts to frosting (make sure frosting isn't too loose as pineapple juice is added) and mix until ready to frost.
  16. Frost each cupcake once it is completely cool and enjoy!
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  1. Beautiful cupcakes Jocelyn! I love those pineapple flowers- so pretty!

  2. Mm..these exotic cupcakes seem to be very tasty!

  3. These look to die for… I do was always amazed by the flip of an up-side-down cake

  4. I love these!! So pretty and I’m sure they taste sooo good!

  5. Gorgeous! I cannot wait to make these for my mom. Pineapple Upside Down Cake was her absolute favorite dessert from her childhood. Apparently, my grandma had a knack for it. :)

  6. These are beautiful! Wishing I could have a HUGE bite!

  7. I do want some of that! Especially that pineapple buttercream — YUM. :)

    Stephanie @ Girl Versus Dough

  8. Your cupcake take on the classic pineapple upside down cake is brilliant! Love the touch of rum. :D

  9. So pretty!!!

  10. Rum and chunks of pineapple seal the deal for me! They’re gorgeous and your family would be proud you took your memories from childhood and created these!

  11. i miss eating these :)

  12. These look so amazing!! And so gorgeous, love the topper. I definitely need to try these ASAP. They seem so perfectly summery!
    Rachel @

  13. oh my goodness, those look delicious!!! Pineapples such a perfect summer fruit, I could put it in anything! :) Thanks for sharing!

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  15. Oh my.. You make me wanna run in the kitchen and re-bake these cupcakes immediately!! They look amazing!!! Especially the decoration totally rocks :)

  16. These are such creative cupcakes in so many ways, Jocelyn. You did an amazing job turning a cake of varied tastes and textures into a cupcake! The brown sugar,butter, and pineapple base that goes in before the batter is perfect for the upside down effect! And the pineapple flower….beautiful!

  17. These cupcakes are off da chain!! :) I am usually very rebellious when it comes to following recipes exactly. I did everything like you suggested … I put half of a marachino cherry in the middle, on the bottom of 12 of the cupcakes the other 12 I did like your’s…I even had enough batter to make two (extra) small torte cakes I put the same ingredients on the bottom,put the bottoms together with the icing in the middle and ….delightful! I lovvvve the pineapple flower tutorial as well they turned out sooo cute. Thank you for sharing , what I consider to be the most precious gift we possess in our kitchens’ as women, grandmas’ recipes’. :)

  18. Very clever, Jocelyn! Imaginative and I’m sure delicious! Great post and beautiful photos!


  19. Hi Jocelyn

    When you remove the cupcake from the liner, does the pineapple fall off.


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