Pineapple Upside Down Cake

filed under: Cakes on June 17, 2019

This Pineapple Upside Down Cake doesn’t look like your average cake. I used a fun method to create a pretty design that always gets oohhs and aahhh’s! Completely from-scratch and using the best ingredients mean that not only will this cake look beautiful, but it will taste amazing!

Pineapple Upside Down Cake

Pineapple Upside Down Cake

This is not your average Pineapple Upside Down Cake! There are two main factors that set it apart.

  • Ingredients – I opted for a completely from-scratch cake using the best ingredients I could find. Real pineapple and of course, real butter! Challenge Butter is made the right way, using the freshest milk from the happiest cows. (You know this homesteader loves that!) Challenge butter is the only major U.S. dairy product company that controls the whole process when it comes to making butter and I love buying the very best when it comes to my baking.
  • Design – I opted to cut my pineapple in long strips and layer it instead of the traditional circle cut design. I also left out the maraschino cherries. After testing this recipe over and over again, I found that the cherries were not necessary for the taste (they actually added an overly sweet – artificial – flavor) and definitely not necessary for presentation purposes.

Rose Design Pineapple Upside Down Cake

How to Make the Pineapple Design

Let’s talk about that crisscross pattern that almost looks like a pretty flower! It is very easy to do. Cut your pineapple (as directed below) and then layer the long slices in your prepared skillet. I used a 12-inch cast iron skillet for this recipe which means using about 1 1/2 pineapples. After making this pineapple dessert several times I found that while the cleaner slices you get when you are closer to the core of the pineapple look best, you don’t have enough of them to have a consistent design. I opted to use the biggest outer slices of the pineapple on the edges of the pan and then work in towards the center of the pan with the smaller pieces. There is a video below showing how to do that!

How to Cut Pineapple

How to Cut Pineapple for Pineapple Upside Down Cake

Start with a cutting board and a very sharp knife.

Place the pineapple on its side and cut off the bottom. When you set the pineapple upright, this will help it to sit flat on your cutting board. I opted to leave the top on for the first few cuts to make it easier to hold.

Stand the pineapple up on the cutting board and starting on the side and press your knife down through the outer layer.

Turn the pineapple a little and make another cut. Continue this around the pineapple until the outer layer is completely removed. If there are any imperfections cut those off. The pineapple should resemble a hexagon.

Now start cutting the slices for the cake. I like mine about 1/4 inch thick. Make a cut, starting from the top and moving to the bottom of the pineapple. Set the long piece aside. Turn the pineapple and make your next cut, going completely around the pineapple until you reach the core. The outside slices will be wider and the slices near the core will be thinner.

Set the cutting board aside and prepare the topping.

Topping for Pineapple Upside Down Cake

Easy Pineapple Upside Down Cake Topping

Two ingredients make up the beautifully caramelized topping for this cake: brown sugar and butter.

Melt butter and pour it into the 12-inch skillet.

Measure out 1 cup of packed brown sugar then sprinkle that over the butter.

How easy is that?

Now it’s time to lay out the pineapple pattern.

Flower Pattern Upside Down Cake

How to Make the Pineapple “Flower” Design

Starting around the outside of the skillet, place your first pineapple slice. I used the widest slices here. Lay the slice down and feel free to cheat up the sides of the pan a bit. Press down gently and then lay the next slice, making sure to overlap a bit. Continue this around the pan until you get to the center. Be sure there is no brown sugar topping peaking through. (Video below)

If you want to add maraschino cherries to this cake, now is the time. I tried adding the cherries around the edge of the pan in a large circle as well as sprinkling them randomly over the pineapple. We liked how the circle design looked best. I used 1 entire jar of maraschino cherries, about 1/2 cup. (As I mentioned above, we didn’t like the added flavor of the cherries and opted to leave them out of the final design.)

How to Make Pineapple Upsidedown Cake

Prepare the cake batter and then pour it over the pineapple slices. Use a spatula and smooth out the batter making sure it covers all the pineapple slices. Place the cake in the oven for 38-42 minutes, or until the center doesn’t jiggle and the bottom is nicely golden brown. If you happen to notice that the cake is browning too fast, you can carefully place foil over the cake for the last 10 minutes.

Pineapple Upside Down Cake with "Flower" Design

When the cake is done baking, carefully remove it from the oven and let it sit for five minutes. After five minutes, place the serving platter over the cake face-down. Make sure to use a platter that is bigger than the skillet! With one hand flat on the bottom of the platter and the other gripping the handle of the skillet (make sure you have a sturdy oven mitt on!) flip the cake over so that the platter is now on the table and the skillet is upside down. Carefully lift the skillet being sure to let all of the glorious brown sugar glaze drip onto the cake.

The Best Pineapple Upside Down Cake

How Do You Serve Pineapple Upside Down Cake?

This cake is best served warm in my opinion, but my kids did enjoy it chilled. If you want, you can drizzle a little maraschino juice over the cake. We have also served it with vanilla bean ice cream! (When the cake is completely from scratch and the ingredients are so pure, it’s best to compliment it with a real vanilla ice cream.)

Easy Pineapple Upside down Cake

Cut a slice and get ready for gasps of delight. Just look at the crumb! The topping and the natural juices from the pineapple ensure that every last bite this cake will be moist and loaded with pure flavor.

5 from 2 votes
Pineapple Upside Down Cake
Pineapple Upside Down Cake
Prep Time
15 mins
Cook Time
40 mins
Course: Dessert
Cuisine: American
Keyword: Pineapple Upside Down Cake
Servings: 8 people
Author: Amanda Rettke
  • 2 1/4 cups (281g) all-purpose flour
  • 1 1/2 cups (300g) granulated sugar
  • 3 1/2 tsp. baking powder
  • 1 tsp. salt
  • 1 1/4 cup milk
  • 1/8 cup vegetable oil
  • 1/2 cup (1 stick or 113g) Challenge Butter, softened
  • 1 tbsp. vanilla extract
  • 3 large eggs
  • 1/2 cup (1 stick or 113g) Challenge Butter, melted
  • 1 cup brown sugar, packed
  • 2 pineapples, cut into long slices
  1. Preheat oven to 350°. Get out a 12-inch cast iron skillet.

  2. In a medium bowl, sift together flour, sugar, baking powder, and salt. Set aside.
  3. Place softened butter into a stand mixer and mix on medium for 1-2 minutes.
  4. Place dry ingredients into the stand mixer and combine with butter for 30 seconds.
  5. Add milk, oil, vanilla, and eggs and mix on medium-high until ingredients are combined.
  1. Pour melted butter into an ungreased skillet. Sprinkle the brown sugar evenly over the butter.
  1. Take the long slices of pineapple and start layering them around the edge of the pan, directly over the butter and brown sugar. It is fine to sneak them up the sides a bit. Continue layering pineapple around the pan working towards the center, making sure there is no brown sugar coming through.
  2. Pour prepared cake batter over the pineapple.
  3. Place skillet in the oven for 38-42 minutes, or until the bottom is browned and the center does not jiggle. You can test the cake with a toothpick; just insert it and if you remove it with any wet batter, the cake is not done.
  4. When the cake is done, remove from oven and let sit for a couple of minutes. Take a large serving platter and place it face-down on the hot skillet. With one hand held flat on the bottom of the platter and the other holding the handle of the skillet (using a hot pad! The skillet will be hot), flip the cake over. Once the platter is firmly on the counter, use both hands to gently lift the skillet away.

  5. Serve immediately.

Recipe Video

Recipe Notes

You can find Challenge Butter here. (Clickable Link)

Thank you for supporting the brands that support us here at iambaker! It has been a dream of mine to partner with Challenge Butter and I am just thrilled to be able to share a product that I love and use!

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  • Susan Chouinard says:

    Do you have to use a cast iron skillet? Is there a substitute? This is my first comment.

  • Karen Scott says:

    What I do not like about Challenge butter is that they refuse to put the paper wrapping on the butter precisely. So, it requires guesswork to figure out where one tablespoon, etc, should be and that’s a problem if you aren’t using whole cubes in a recipe. Any other butter that I buy is able to do this, so why can’t Challenge?

  • Nancy Hackett says:

    Can you use a box cake mix?

  • Winni says:

    Pineapple is one my favourite fruit. Cake in the pictures is looking very good. Never tried a pineapple cake but after seeing this i will try pineapple cake.

  • Sue Clements says:

    canthis recipe be made in anything other than a cast iron pan?

  • Christopher says:

    Hello Amanda!Pineapple are my favourite, inducing it in Cake Recipe is a great idea.btw Thankyou for your Recipe.Farhat sweet pineapple cake Is amazing for a try.

  • Vicki Entrekin says:

    Oh! That looks SO good!!

  • Chilidog1947 says:

    Sue Clements, I don’t think this particular cake works with any other type of pan. An iron skillet is heavy enough that the cake doesn’t over cook on the bottom before it is done on top. Iron distributes the heat really well.

  • Ronak Mehta says:

    I tried out cake with the above recipe. The cake was very soft and tasty. Thank you.

  • Aletha Carter says:

    what type of mike should I use buttermilk or regular milk

    • Elizabeth Keeney says:

      Hi, Aletha! I work with iambaker and am happy to help with questions. Use regular whole milk for the best results in this recipe. I hope this helps, and have a great day!