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double layer pineapple upside down cake

Pineapple Upside Down Cake

Pineapple upside down cake was something I had never tried until I was 43 years old. I had seen it, but never tried it. It wasn’t something that appealed to me for some reason. My significant other loves pineapple upside down cake and said that was what he wanted for his birthday. I agreed to make it for him. And I have loved this cake ever since. I can’t believe I never tried it before. On a better note, think of all the calories I saved by NOT eating it before recently.

Truthfully, this cake is delicious. The brown sugar on top caramelizes with the butter in the pan and is absolutely amazing. The pineapples bring sweetness and give the cake the best consistency, it’s juicy and very tasty.

As far as cake baking goes, this requires an extra step or two. You could make this cake from scratch which I have done before. It tasted great. However, you can skip a bunch of steps by using a box cake like Betty Crocker yellow cake mix or pineapple cake mix, making this a huge time saver for preparation and cleanup.

Getting started, you will need to prepare your pan for your top layer of the cake. The top will actually be the bottom and you will start there. This is confusing, but this is where the upside down cake comes from. You will pour the melted butter into the cake pan, then sprinkle brown sugar evenly on top of butter. The artistic portion is arranging the pineapple slices on top of brown sugar. Finally, you will place a maraschino cherry in the middle of each pineapple slice (you could also substitute with a pecan for each pineapple slice). I tend to do a cherry and pecan in each pineapple because I can’t decide which I prefer.

Once you prepare the cake batter, just pour it directly onto the pineapples and cherries. Now you are ready to bake the cake. Pretty easy, if you ask me.

As the cake is baking, you can prepare the pineapple cream cheese frosting. This tastes even better than it sounds by the way. The first time I made this, I went overboard with the pineapple juice. I wanted the frosting to have a really strong pineapple flavor. And it did. However, too much juice makes the frosting too wet. And wet frosting doesn’t stick well. It tasted out of this world fantastic, but it didn’t look as pretty as I had hoped.

pineapple upside down cake with cream cheese frosting

Once the cake has cooled, frost the edges of the cake with the pineapple cream cheese frosting. After that, I highly advise you to add chopped pecans to the frosting. The pecans give the frosting a crunch texture that really accentuates the taste of everything.

With so much yumminess on this cake, you truly don’t need anything else, but homemade whipped cream won’t hurt! If you throw caution to the wind and add whipped cream to a slice of this cake, you will be love it, trust me!

Pineapple Upside Down Cake

Easy Pineapple Upside Down Cake
Prep Time10 mins
Cook Time35 mins
Total Time45 mins
Course: Dessert
Keyword: autumn breakfast pancakes, easy cake, pineapple upside down cake
Servings: 8 people
Author: jenahoward


Pineapple Upside Down

  • 1/4 Cup Butter Melted
  • 1 Cup Brown Sugar
  • 1 Can Pineapple Slices in juice, drained Reserve the juice
  • 1 Jar Maraschino Cherries take stems off
  • 1 Box Yellow Cake or Pineapple Cake
  • 1/2 Cup Vegetable Oil
  • 3 Eggs
  • 8-10 Pecans if desired

Pineapple Cream Cheese Frosting

  • 8 oz Cream Cheese softened
  • 1/2 tbsp Pineapple Juice
  • 3 Cups Powdered Sugar
  • 1/2 Cup Pecans if desired


Pineapple Upside Down Cake

  • Preheat oven to 350 degrees and grease 13 x 9 pan
  • Pour melted butter into pan.
  • Sprinkle brown sugar evenly on top of butter.
  • Arrange pineapple slices on top of brown sugar.
  • Place a maraschino cherry in the middle of each pineapple slice (you could also substitute with a pecan for each pineapple slice).
  • Add enough water to reserved pineapple juice so that the liquid measures 1 cup.
  • Mix pineapple liquid, cake mix, oil, and eggs in a large bowl on medium speed for approx 2 minutes. Make sure there are no bumps.
  • Pour cake batter into prepared pan (directly on top of pineapples and cherries).
  • Bake for 35-40 minutes. Cake will be done when you insert a toothpick and it comes out clean.
  • Place a heatproof pan/plate upside down and place on top of pan. Holding both the plante and the pan, turn them over together and place the plate right side up on the counter. Keep pan turned upside for 5 minutes.
  • Remove pan and cool for 30 minutes.
  • Frost sides of cake with Pineapple Cream Cheese Frosting.
  • Cover frosting with chopped pecans, if desired.
  • Serve warm or cool (warm is so much better)!
  • This doesn't need a garnish, but homemade whipped cream tastes great on the side.
  • Enjoy!

Pineapple Cream Cheese Frosting

  • Put cream cheese, powdered sugar, and pineapple juice in a large bowl.
  • Mix well. Consistency should be frosting-like. If too wet, add more powdered sugar. Don't add too much pineapple juice. It will taste great, but the frosting will be too watery to stay on the cake.
easy pineapple upside down cake

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