Recipe: Pineapple Upside-Down Cupcakes

Our contributor, Lauren of Crave. Indulge. Satisfy., is back with a delicious new recipe….

Sweet pineapple, brown sugar, butter and a cherry center are the star ingredients of one of my favorite traditional summer cakes, Pineapple Upside-Down.  Today I’m re-inventing this cake as a mini version.  Typically when I think of Pineapple Upside-Down Cake I think of pineapple rings with a cherry in the middle, which is beautiful when baking a large cake.  For this recipe, I decided crushed pineapple would be the way to go for these individual treats.

Pineapple Upside-Down Cupcake by Lauren Kapeluck  |

What makes the Pineapple Upside-Down cake so special is the pairing of the pineapple with melted butter and brown sugar to create a gooey golden topping when these cakes are baked and turned over.  I threw in some chopped walnuts for a little crunch and texture, which were a great addition to these cakes.  For the actual cake batter I used a combination of both granulated and brown sugars to carry out the brown sugar flavor from the pineapple mixture.

Pineapple Upside-Down Cupcake by Lauren Kapeluck  |

Since I had never baked a mini version of a Pineapple Upside-Down Cake before, I wanted to experiment with baking these in the muffin pan.  I lined half the pan with paper liners and the other half I sprayed with baking spray and assembled directly in the pan.  As it turns out both cakes came out nicely and tasted delicious, but visually I prefer the look of the cakes that were baked directly in the pan because they had a golden brown outside.  The cakes baked in the liners lost some of the golden look once the paper was removed.  The liners also got a little soggy with the gooey topping, and removing the liners added another step since you have to remove the paper in order to reveal the beautiful tops of these cakes.  So there’s my take on the experiment, but I’ll leave the “liner vs. no liner” decision up to you when you try this recipe.

Pineapple Upside-Down Cupcake by Lauren Kapeluck  |

A bonus to making these cupcakes is there is no icing involved so you can safely serve these cupcakes at an outdoor summer event and not have to worry about any buttercream getting soft and melting in the heat.  These cupcakes are beautiful on their own without any decorations, with the bright yellow pineapple and the red cherry center.  Wouldn’t these cupcakes be the perfect addition to a summer pool party our luau?

Pineapple Upside-Down Cupcake by Lauren Kapeluck  |

recipe by Lauren Kapeluck
(makes 24)

For the cake:
2 sticks unsalted butter, softened
1 1/2 cups granulated sugar
1/2 cup packed brown sugar
3 eggs
2 1/2 cups all-purpose flour
1 tsp baking powder
1/2 tsp baking soda
1/2 tsp salt
1 tsp vanilla
1 cup sour cream


  1. Preheat oven to 350 degrees.
  2. Spray muffin pans with baking spray (I use Baker’s Joy). You could also line the pans with cupcake liners.
  3. In medium bowl combine all dry ingredients: flour, baking powder, baking soda and salt, mix well and set aside.
  4. In bowl of stand mixer beat butter and sugars on medium speed until light and fluffy.
  5. Add eggs one at a time and beat until combined, scraping sides of bowl as necessary.
  6. Add vanilla and mix.
  7. Add in half of the dry ingredients and mix, scraping sides of bowl.
  8. Add in sour cream and mix until well combined.
  9. Add in the rest of the dry ingredients and mix another minute until well combined.

Pineapple Mixture:

1/2 stick unsalted butter, melted
1/2 cup packed brown sugar
2 (8oz) cans crushed pineapple, drained
1/2 cup chopped walnuts
12 maraschino cherries, cut in half

  1. In large bowl mix melted butter and brown sugar.
  2. Add pineapple and walnuts and mix well.

To assemble the cupcakes:

  1. Place half of a maraschino cherry cut side up in the center of prepared muffin pan.
  2. Spoon pineapple mixture around the cherry.
  3. Place a scoop of cake batter on top of the pineapple mixture.
  4. Bake for 20-22 minutes until toothpick inserted in center comes out clean.
  5. Let cupcakes cool in pans for about 10 minutes.
  6. Run a knife around the cupcakes in the pan and then invert onto wire rack to continue cooling.

These cupcakes are delicious served warm but can also be enjoyed at room temperature, or even with a scoop of ice cream! Hope you all enjoy and have a wonderful summer!

Lauren Kapeluck , CONTRIBUTOR

Lauren is a monthly contributor for The Cake Blog. She is a self-taught baker and lover of all things sugar. Read more about Lauren on her bio page.


  1. 1


    Hello! Thank you for sharing with us your perfect recipe, I’ll definitely try this at home, I was really looking for something new for my kids who always go to school and I really wanted to bring with them my home made recipe as their snacks because I don’t want them to buy anywhere in canteen or outside the school. I have already copied it in my recipe notebook. Thank you so much for this and I’m looking forward for you more recipes to post.


  2. 5

    Sehnaaz says

    These look delicious. I’ve one question for you. How many grams is the butter? They don’t sell sticks (butter) in my country. Many thanks in advance.
    I really want to try these!!

    I hope hearing from you!

    Kind regards,

  3. 9

    Karen says

    I made these today and they were DELICIOUS!! My family gobbled them up! They came out looking just like the picture. I made them without the paper liners. Thanks for sharing the recipe!

  4. 11


    These look great! Have you tried the tin cupcake liners? I find for moister items like muffins those work well. Perhaps they would brown better than paper?

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