Pineapple Upside Down Cupcakes

Apparently the number one food of the 1920’s was pineapple upside down cake so for our 1920’s party, I made cupcakes!  I found a delicious recipe on:

Let’s dive into the recipe:

12 slices of fresh pineapple
Maraschino cherries
1 cup brown sugar
1 stick unsalted butter
1/4 cup pineapple juice (blended from fresh pineapple)
1/2 teaspoon ground cinnamon

1 vanilla cake mix (and ingredients for it)

Making the pineapple topping
1) Melt the butter in a saucepan over medium-low heat
2) Add brown sugar and pineapple juice until it has dissolved, then remove from heat.
3) Mix cinnamon to the sugar mixture

Make the vanilla cake batter

Assembling the cupcakes
1) Butter the muffin pan or ramekin
2) Scoop 2-3 teaspoons of the sugar mixture into the bottom of the ramekin
3) Place a pineapple slice on top & a cherry in the middle
4) Spoon batter into the ramekin until three-quarters full
5) Bake for 20 minutes or until a skewer inserted into the middle comes out clean
6) Allow cakes to cool for 10 minutes before serving

I followed these directions exactly and it turned out delicious.  I made some in my silicone cupcake pan and some in ramekins. They were both perfect and delicious.

This dessert fits into my general thoughts of everything is better bite size!  Mmm mmm.

Happy eating!



  1. My Mom didn’t cook very much but one of the things she did make was pineapple upside down cake. I have very fond memories of that and of my Mom from my childhood. Looks yummy!

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