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Pineapple Upside Down Cake with Crushed Pineapple

  • Author: Kindly Unspoken
  • Prep Time: 7
  • Cook Time: 25
  • Total Time: 32 minutes
  • Yield: 2 8-inch round cakes 1x
  • Category: Dessert
  • Method: Bake
  • Cuisine: American


You’ll love my easy, delicious, and quick pineapple upside down cake with crushed pineapple. It’s made with a boxed yellow cake mix and double the pineapple in 30 minutes!


  • 1 box yellow cake mix, prepared as directed with exception noted below*
  • 1/3 cup of butter, melted
  • 1 cup of light brown sugar
  • 1/4 tsp vanilla
  • 1 20 oz can of pineapple tidbits, drained and juice reserved
  • 1 20 oz can of crushed pineapple, drained
  • 1 6 oz can of maraschino cherries, drained and stems removed


  • Preheat oven to 350 degrees (325 for dark or nonstick pan)
  • Spray 2 8″x3″ cake pans with non-stick spray and set aside. Open and drain both the pineapple tidbits and crushed pineapple in a colander, reserving 1 cup of juice for the cake mix.
  • In a microwave safe bowl or pot on the stove melt butter and add in brown sugar and vanilla. Place on stovetop over low-medium heat and stir for a minute or two until the brown sugar is well incorporated.
  • Immediately pour the butter and brown sugar mixture evenly into the bottom of the cake pans.
  • Next begin scooping the drained crushed pineapple on top of the brown sugar mixture in the bottom of both cake pans and carefully spread. Top with pineapple tidbits.
  • In a large mixing bowl, prepare cake mix as directed on the box. The only exception is that you will use pineapple juice instead of water. Once prepared, pour cake batter evenly into the two cake pans, ensuring all the pineapple is covered.
  • Bake in preheated oven for 25-35 minutes or until cakes are a light golden brown and a toothpick inserted into the center comes out clean.
  • Let cakes cool for 10 minutes in pan on a cooling rack. Next, place a plate or serving platter upside down on top of the cake pan and carefully turn over.
  • If desired, garnish the top of the cake with maraschino cherries that have been drained, cut in half, and had stems removed.
  • Let cake cool additional 20 minutes on cooling rack before serving or covering for later serving.
  • Slice cake, top with whipped cream or vanilla ice cream if desired, and enjoy!


  • Use reserved pineapple juice instead of water in cake mix
  • For optimal freshness, leftover cake should be refrigerated in a glass dome or covered with plastic wrap and refrigerated. It tastes great cold, but you can also reheat slices in the microwave for 15-30 seconds, if desired.

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