Cherry Pineapple Upside Down Cake

This cake was a complete fluke.

Cherry Pineapple Upside Downcake

You ever had that experience where you found a bunch, of what seems to be, unlikely ingredients that actually works well together? I stumbled across a bag of frozen cherries that I was actually going to use for another purpose but as I stared at the bag for a while I remember something I had in college that a friend made that I absolutely fell in love with. It was a dump cake, if I am remembering correctly. It was kind of like this cake but backwards. She took a can of cherry filling and crushed pineapple and mixed it together and used yellow cake mix as a crumble that was crunchy, yet moist and buttery. To this day I still don’t know how she made the topping the way it was. So, I thought I take that same idea and flip it again making Cherry Pineapple Upside Down Cake. What do you think, huh?

Cherry Pineapple Upside Down Cake

While I was thinking about my old college friend that made this cake, I started remembering all the horrible food choices that I made that I wish I could go back and change. Let’s see, I use to eat cake and juice for breakfast; I used to eat fast food probably 3-4 times a week; and I just ate whatever I wanted when I wanted. Sure I attempted to work out from time to time but it never was consistent. Now, I make better food choices. I am not as consistent as I wish I were but I am working on it. It is hard to stay consistent when you have a mind that is always coming up with ideas like this! I honestly do pray that the things I come up with don’t work out so I don’t get tempted to eat the entire batch of cookies or half the cake.

Cherry Pineapple Upside Down Cake

A new trick that I have learned that works out well for me is I store whatever sweets I make in the freezer. I guess it’s that whole out of mind out of sight deal. It works too, until I have to go in the freezer. The good thing is that the baked good is frozen so I can’t just eat it. But now, I have an awesome place where I give these tempting desserts away. Thank you Ms. Michelle for taking my food to your job! At least it is out of my house. I can sleep better at night. This cake is super buttery, moist, sweet, and tart. The flavor is enough to keep you up dreaming.

Cherry Pineapple Upside Down Cake

Cherry Pineapple Upside Down Cake

Cherry Pineapple Upside Down Cake


  • 1 lb. frozen unsweetened cherries
  • 1 tsp. lemon zest
  • 1 tbsp. fresh lemon juice
  • 1/2 c. sugar
  • 2/3 c. crushed pineapple
  • 1/4 c. water
  • 1 tbsp. cornstarch
  • 1 Box Duncan Hines Yellow Cake Mix
  • 3 eggs
  • 1 stick butter, melted
  • 1 c. water
  • 1/2 tsp. almond extract
  • 3/4 c. crushed pineapple


  1. Preheat oven to 350 Degrees
  2. In a medium sauce pan combine the frozen cherries and sugar. Stir on medium heat. The cherries will begin to release its liquid. Add the lemon zest and juice. Continue to stir as more liquid is released. In a small ramekin add the 1/4 cup of water and tbsp. of cornstarch and stir until dissolved. Pour into the cherry mixture. Add the crushed pineapple (2/3 cups). Allow to simmer on low to medium heat for 10-15 minutes. The sauce will thicken. Set aside.
  3. In a separate bowl, combine the cake mix and blend in the eggs, melted butter and water until smooth. Add the almond extract and the 3/4 cups of crushed pineapple.
  4. In a medium sized cast iron skillet, spray the entire pan with baking spray. Pour in just enough of the cherry glaze to cover the bottom of the pan (about half). Reserve the rest.
  5. Pour in the cake batter on top of the cherry glaze. Place the pan on top of a baking sheet because the glaze may bubble a little bit. Bake in a preheated oven for 25-30 minutes or until toothpick is inserted in the middle of the cake and it comes out clean.
  6. Allow to cool for 10-15 minutes. Take a plate and place it on top of the pan and flip it upside down and the cake should come out smooth. Pour the rest of the cherry glaze on top of the cake and serve.


  1. says

    Do you add the 3/4 cup of crushed pineapple and almond extract to the cake mix? There are two different measurements of crushed pineapple listed in your recipe but it doesn’t really specify in your instructions which goes to the glaze or cake mix.

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