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Portteus Family Pineapple Upside-Down Cake

Photo by Rohan Portteus

Pineapple upside-down cake has been a traditional Portteus family dessert for decades now. It all started with my father who, at the age of nine, requested a pineapple upside-down cake for his birthday back in the ‘70s. This single request kickstarted a family favorite recipe that is made every year. 

My grandmother first introduced me to the recipe when I was nine, the same age as my father when he first had this cake. She sat me down in the kitchen while she walked down the hall and pulled out her old tattered recipe book from the shelves. She leafed through the pages until she found the page labeled “pineapple upside-down cake,” the title written in her swoopy handwriting that I could barely read.

She employed me to grab the ingredients from the cabinet and then helped me up to the counter to watch her prepare the dish. 

I watched her melt the butter over the stove and helped her pour the brown sugar into the pan. Next, I was in charge of placing the cherries and pineapple into the dish, laying them out in a matrix of pineapple rings with cherries in the gaps between the pineapple rounds.

While I set this up, my grandmother told me stories of my father making this same cake when he was nine. I watched her slowly pour the batter over the rings, in awe of the dessert we were creating. 

As soon as I heard the ding of her timer, I rushed to the oven with mitts in my hand. In a rush, we flipped the cake over revealing the beautiful pattern of the cake and wafting the scent of pineapple throughout the house. Although the pineapples were a mess and the cherries were bleeding all over, my grandmother held me tight and told me how proud she was of our creation.

Even now we use the same pan to melt the butter as we did those long years ago. I truly value these moments with my grandmother now, and the recipe lives on still in that same recipe book.



  • 1  (20oz) can dole pineapple rings 
  • 1  (6oz) jar maraschino cherries 
  • 1 box yellow cake mix 
  • 1 stick of butter 
  • 1  cup brown sugar 
  • Ingredients required for cake mix (water, oil and eggs)



  1. Preheat the oven to the temperature listed on the boxed cake mix
  2. Grease a 9×13 baking dish
  3. In a microwave-safe bowl, melt the stick of butter then pour it into the baking dish 
  4. Pour the brown sugar into the same baking dish and mix until evenly combined, then spread the mixture evenly across the whole pan
  5. Next open the can of pineapples, straining any leftover juice into a measuring cup
  6. Place pineapple rings in a grid pattern, covering the whole pan 
  7. Open a can of cherries and dry thoroughly
  8. Place cherries inside each ring
  9. Let the baking dish sit and begin making the cake, following the instructions on the box
  10. Swap out the water required for cake with leftover pineapple juice from the can
  11. Beat cake mix with a hand mixer until completely smooth
  12. Pour batter into the baking dish in an even layer over the pineapples and cherries
  13. Place cake in oven for time listed on cake box 
  14. Once out of the oven, let cake rest for 15 minutes
  15. Place a baking sheet over the top of the dish
  16. Carefully but quickly flip the pan and allow the cake to separate from the baking dish on its own
  17. Leave the pineapple upside-down cake on the counter for 5 minutes after flipping, allowing the caramelized sugar to set
  18. Slice into square pieces, and serve with vanilla ice cream 

Note: the pineapple rings may not fit perfectly in the pan, if not just half them and continue with a halved version of the pattern chosen

Note: any juice left in the cherries will discolor the pineapples and bleed through the batter 

Note: add water if not enough pineapple juice 

Note: cooking time may vary due to swaps in the batter formula; check if done with a toothpick

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About the Contributor
Rohan Portteus
Rohan Portteus, Reporter
Who are your favorite music artists?  Lana Del Rey, Fiona Apple, Fleetwood Mac Where's the next place on your travel bucket list and why?  Thailand to visit the elephant rehab centers. What causes are you passionate about? Gender inequalities.