Pineapple Upside Down Cupcakes


1/4 cup butter
1/4 cup light brown sugar
1 tablespoon light corn syrup
20 oz canned pineapple rings in 100% pineapple juice, drain and reserve juice for batter

Cake Batter:
1/4 cup sugar
1/4 cup butter, at room temperature
1 cup flour
1 egg, at room temperature
1/2 cup pineapple juice
1 1/2 teaspoons baking powder
1 teaspoon vanilla

Preheat oven to 350. Butter or spray (with cooking spray with flour) 10 wells in a cupcake pan. Cut a 1/2 inch chunk out of 10 pineapple slices and place the slices (not the little chunks) individually in 10 cupcake wells. They should lie flat in the pan and look like a “whole” ring again. In a small saucepan, melt and stir together butter, brown sugar and corn syrup. Cook over low heat about 5 minutes or until it thickens slightly. Stir thoroughly to combine. Pour about one teaspoon of this topping into the bottom of each pineapple ring covered cupcake well. In a medium sized mixing bowl, cream together the butter and the sugar until fluffy. Add the egg and vanilla and mix thoroughly. Add the baking powder, mix briefly then add the flour alternately with the pineapple juice. Pour about 1/3 to 1/2 cup of batter over each pineapple slice and bake for 20 minutes. Cool 20 minutes in pan then invert over a baking rack. You may want to place parchment paper or a towel under the rack because they may drip. Serve on a plate, pineapple side up.

My thoughts:

A friend from out of town is coming over for dinner tonight with her husband and little girl and I wanted to make something fun for dessert that I could make ahead of time. I debated about making a pineapple upside down cake but cupcakes sounded more fun. All of the recipes I found called for crushed pineapple in syrup or pineapple tidbits and a basic yellow cake recipe but this wasn’t exactly what I had in mind. What I really wanted were cupcakes with a whole pineapple slice on top, so much prettier than just pineapple chunks or crushed pineapple. I realized that if I just took a little chunk out of each ring I could get them to lie flat in the bottom of each cupcake. I also thought that a buttery brown sugar glaze sounded more appetizing than simple heavy syrup so I made a sugar glaze, adding a bit of corn syrup to keep it from getting grainy. For the cake I made a simple cake batter substituting pineapple juice for milk for extra pineapple flavor. It’s not a fluffy cake, but it has a nice texture. I created the recipe to yield ten so you shouldn’t end up with much, if any, pineapple slices or bits of juice leftover. I was pleased with how well my first attempt came out. They are simple, not too sweet and very pineapple-y.


  1. Wow, these look so yummy! I love pineapple upside down cake and these cupcakes seem so perfect. How ingenius is that? Thanks for the recipe, will have to make this one day!

  2. Will defanitely try this one out someday. How very intersting,pineapple upside down “cup cakes” !!!!! Good job…

  3. great idea! thanks for sharing, I love pineapple and want to make this VERY soon.

  4. oh, i love them! how cute. this is a much better idea than a whole cake, i think.

  5. christelpistol

    oh my… ima need you to come to my house and make me a batch of these RIGHT now!

  6. A maraschino cherry atop each would be an added bonus.

  7. Since this is the anniversary of the van pool rollover two years ago, this will be a perfect treat to bring. Thanks for the tip on making the ring smaller!

  8. I saw this recipe and thought “I have to try this!” so I did and the results were amazing very delicious! Thanks for the great recipe

  9. Your cupcakes were a huge hit at our cookout last weekend! thanks!

  10. The cupcakes turned out great. I used a boxed pineapple cake mix. I will be making these again. Gail

  11. I just made a recipe with crushed pineapple, and these look SO much better! I’ll definitely be altering my recipe next time! Everyone at work (and my boyfriend) LOVE the cupcake idea, vs. the cake. Much easier to share!

  12. What a great idea!!

  13. Rosa's Yummy Yums

    It is a good idea to create portions instead of having a huge cake! Very nice…

  14. These are great! I just posted an upside down cake this week and love the idea of making them into cupcake form. Thanks for the idea!

  15. you are a genius- what a great idea!

  16. I made these today for the first time and they were delicious! I also added the maraschino cherries and they turned out perfect. I will definitely be back to the site for more recipes!

  17. Thank you, these came out perfect for a Cinco de Mayo party I went to today! I garnished each with a strawberry slice. 🙂

  18. hi rach,
    great idea! but what can you use/add more of if you dont have corn syrup?

  19. Jenn-I recommend using corn syrup, there is really no subsitution that will work in the recipe.

  20. Jenn: The reason for the corn syrup is to prevent the brown sugar from crystallizing, leaving you with something that's silkier and not crunchy. The reason why is acts like a "chaperone" preventing the sucrose molecules from growing. You can try honey for the recipe as honey contains a few different sugars. (TRY is the key word)