Double Pineapple Upside-Down Cake

Double Pineapple Upside-Down Cake

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  • Total: 65 mins
  • Prep: 25 mins
  • Cook: 40 mins
  • Yield: 24 pieces (24 servings)

I bet you didn’t think it could get any better than the brown sugar and buttery taste on the top of a pineapple upside-down cake. Just wait until you taste the incredibly moist the cake portion you’ll get with this recipe. By adding crushed pineapple in its juice not only adds extra moistness to the cake, but it also ups the pineapple flavor.


  • 6 tablespoons butter
  • 1 cup brown sugar (packed)
  • 1 (20-ounce) can pineapple slices (drained)
  • 1 jar maraschino cherries
  • 3 eggs
  • 1/3 cup vegetable oil (or coconut oil; melted and cooled butter works, too)
  • 1 (20-ounce) can crushed pineapple (undrained)
  • 1 box yellow cake mix (for a 2-layer cake)

Steps to Make It

  1. Gather the ingredients.

  2. Preheat the oven to 350 F.

  3. Melt 3 tablespoons in 2-round cake pans or all 6 tablespoons of butter in a 9 x 13 pan in the oven.

  4. Remove the pan(s) from the oven and sprinkle the bottom(s) with the brown sugar. Use a spoon to evenly spread it.

  5. Decoratively arrange the pineapple slices on top of the brown sugar. Fill in the spaces with the maraschino cherries.

  6. In a bowl, break the eggs. Add the coconut oil and crushed pineapple. Stir them together.

  7. Pour the cake mix on top of the wet ingredients. Mix for at least 2 minutes. Don’t worry if the crushed pineapple becomes even finer.

  8. Carefully, pour the batter in the prepared pan(s).

  9. Bake the cake(s) for about 40 minutes or until done.

  10. Remove them from the oven. Very carefully invert the cake(s) onto a serving platter or plate.

  11. Serve your Double Pineapple Upside-Down Cake warm or room temperature topped with whipped cream.

  12. Enjoy!


  • Depending on how many people I serve at a time is how I decide which pans to use to bake this cake. It’s a big help to have one cake to eat and the other to put in the freezer for later.