Pineapple Upside-down Cupcakes

I have to admit, I was initially skeptical about these cupcakes when I first looked at the recipe. After all, it was a simple, box cake mix recipe. However, to my surprise, these little treats turned out to be the moistest and most delicious cupcakes I have had in a long time.

My friend discovered the recipe and requested that I bake them for her. Being a good friend and also excited for an excuse to bake, I whipped up a dozen of them. The cupcakes turned out so good that my partner and I couldn’t resist indulging in two each. To prevent ourselves from devouring the rest, I promptly packed them up to take to school the following day.

The cupcakes were a hit with my colleague Ginger, and my friend Tina was so impressed with them that she refused to share hers. So, without further ado, here’s the recipe:

Pineapple Upside-down Cupcakes

Prep Time 15 minutes
Cook Time 25 minutes
Total Time 40 minutes


  • 2 large sized muffin tins (6 hole)
  • baking spray


  • 1 cup brown sugar
  • 1 stick butter
  • 1 can pineapple rings
  • 1 bottle maraschino cherries

For the Batter:

  • 1 box yellow cake mix
  • 1 small box french vanilla instant pudding
  • 4 eggs
  • 2/3 cup water
  • 1/3 cup pineapple juice
  • 1/2 cup oil


  • Spray the tins with baking spray and preheat the oven to 375 degrees. In a sauce pan, put the brown sugar and butter together and melt until fully blended. Now put 2 Tbs. of the sugar mixture in the bottom of the muffin tins. Add a ring of pineapple to each and put a maraschino cherry in the middle of the ring. Then make the batter.

For the Batter:

  • Mix the ingredients for the batter together and beat on medium for 2 minutes. Fill each muffin tin until they are 3/4 full and bake for 20 – 25 minutes. Place a sheet of parchment out on your counter and then turn over the muffin tin onto the parchment. Let cool for a few minutes. We liked to eat them warm. I promise, you won’t be disappointed.
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