Pineapple Upside Down Cake Recipe

pineapple upside down cake

I love pineapple upside down cake; and what’s not to love? It is moist, packed with delicious pineapple–a fruit that single-handedly defines what the spring and summer months are all about in terms of flavor–encased in a thick, caramelized brown sugar crust, and so delightfully sweet. I had not had a pineapple upside down cake in so long, but thought it would be the perfect dessert to ring in the beginning of spring, and with it, warm weather and fond thoughts of juicy, delicious fruit.

pineapple upside down cake top

Instead of making one large pineapple upside down cake, I decided to make two small cakes in round cake pans, completely changing up the look of the traditional square cake. While I did have a square pan that would have been perfect for the cake, having never made a pineapple upside down cake before, I was apprehensive about how the whole flipping an entire cake over process was going to play out. My initial thoughts on it: oh hell no; also: cake everywhere.

Luckily, the cakes flipped perfectly and I have no messy cake incidents to report. A thick layer of melted butter at the bottom of a pan apparently works wonders to form a barrier between a fluffy cake and its pan. This, combined with running a knife around the cake right after it comes out of the oven makes for an easy cake-flip.

pineapple upside down cake closeup

My pineapple upside down cake looks a little different than it’s supposed to, but I can explain! Aside from it being round, I used dark brown sugar instead of light brown sugar. This made for a much darker cake, but a cake just as delicious as any other pineapple upside down cake I have had.

This cake is super easy to make; so easy that it actually comes from a box with just a few adjustments.

pineapple upside down cake slice

Pineapple Upside Down Cake Recipe


  • 1/4 cup unsalted butter
  • 1 cup packed light brown sugar (dark brown sugar will work, but your cake will come out much darker)
  • 1 can (20oz) pineapple slices in juice, drained into a measuring cup with juice reserved
  • 1 jar (6oz) maraschino cheeries without stems, drained
  • 1 box yellow cake mix (I used Pillsbury, any brand will do)
  • Vegetable oil and eggs as called for on cake mix box


  1. Preheat oven to 350° F. Melt butter in 13×9″ baking pan, checking on it every minute until thoroughly melted.
  2. Crumble brown sugar over melted butter. Then, gently press pineapple slices on brown sugar and press a cherry in the center of each pineapple slice. Arrange remaining cherries around the pineapple slices.
  3. Add water to reserved pineapple juice to measure 1 cup. Make cake batter as directed on cake mix box, substituting your pineapple juice mixture for the water. Then, pour cake batter over the pineapple slices and cherries.
  4. Bake cake for about 45 minutes, or until toothpick inserted into the center comes out clean.
  5. Once the cake is finished baking, run a knife around the cake pan to loosen cake. Place a heatproof plate upside down onto your cake pan and turn the plate and pan over, flipping the cake. Leave the pan over the cake for about 5 minutes to the brown sugar and butter can melt over the rest of the cake.

pineapple upside down cake slice side

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About Holly

In addition to being the driving force behind Woman Tribune, Holly is a self-taught web designer, gamer, and wannabe baker living in NEPA with her fiance and 5 cats.

5 thoughts on “Pineapple Upside Down Cake Recipe

    1. Good luck if you ever do venture out into the upside down cake world, and thanks for letting me know about your Friday Food Frenzy feature. I just added this recipe and will definitely take a look around.

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