
Upside down cakes are simply cakes that when flipped over have some kind of topping. Generally speaking, there is fruit on top that has been baked with the cake. The most common type of upside-down cake is the pineapple upside down cake. Why is it so popular? I like to think it is popular because the tangy-ness from a baked pineapple offsets the sweet baked cherries, plus that delicious and moist yellow cake makes everything just come together. I believe using a yellow cake is the traditional pineapple upside down cake. In this recipe, I will use pineapples, maraschino cherries, and a yellow cake recipe.

I’ve read in several cookbooks that raspberries, plums, peaches, etc. all work for upside-down cakes as well. You can change up the fruits if you are feeling adventurous!
Follow these steps to make a delicious pineapple upside down cake:
- Spread brown sugar.
- Place the pineapples and cherries in pan.
- Make batter and pour it into pan.
- Bake and enjoy!
That’s all it takes to make some good pineapple upside down cake. Of course, you need to take some time to make the batter, so that might be an extra 3 side steps. Either way, let’s get down to this recipe!
Spread the Brown Sugar
The first step is to grease a 9-inch round pan. Initially, I wasn’t going to grease the pan partly because I felt the caramel would help it slide out. Then I realized it is better to be safe than sorry. So, I greased the pan. After you grease the pan go ahead and sprinkle some brown sugar on the bottom of the pan. You basically want a thin layer on the entire bottom.

Story time: when I did my first trial run, I decided to melt the brown sugar to see if that helped flavor-wise. The problem I ran into was that I couldn’t exactly tell when the brown sugar was caramelized. I got it to a nice deep brown color (as pictured below).

However, after I baked the cake, the brown sugar turned almost black (as pictured below).

The cake and everything else looked fine, but the cooked brown sugar made everything look burnt. The taste was interesting. It’s like the brown sugar had taken the sweetness out of the pineapple. This gave us a sour pineapple and an ok cherry flavor. Definitely not what I wanted, so I opted back to the traditional method of letting the sugar melt while it cooks. Maybe next time I’ll see if I can make melted brown sugar work (hahaha!).
Place the Pineapples and Cherries
The next step is to align the pineapple slices all over the pan. I started by decorating the center and then halving the pineapples to decorate the sides. Place the cherries in the center of the pineapples. You can also squeeze some cherries in between the pineapple slices for extra cherry goodness. Honestly, I forgot to add the cherries in between the slices as well. Whether you put cherries everywhere or only in the center pineapples, it will look great.
Make the Batter
Go ahead and make the batter. It’s a simple batter that requires you to cream the butter and sugar then add in the wet ingredients and finally the dry ingredients. This recipe doesn’t look like it gives you a lot of batter; but trust me you don’t need a whole lot when you have pineapples stacked at the bottom.
In my first trial run, I added way more batter. It ended up baking a little lopsided and overflowing. It took a while to bake all the way through and so I think that may have contributed to the blackish sugar.
Once the batter is mixed, go ahead and pour it on top of the pineapples and cherries we have prepared. It should leave a little bit of space between the top of the batter and the top of the pan. Don’t worry, when it bakes it will cover the pineapples that look like they are sticking out.

Also, in the first trial the batter was a little thicker. After taste testing, I realized that the best cakes are light and fluffy. The density of this cake was more akin to a pound cake. A dessert that holds its own. Maybe a little too thick for this pineapple upside down cake. But, hey that’s why I test these things out!
Bake & Enjoy the Pineapple Upside Down Cake!
Once it is fully baked, a knife or toothpick inserted will come out clean. It should be golden brown. Let it cool for a about 10 minutes or so and then flip it over onto a plate. The finished cake should look like the picture below.

This recipe gives you a moist and springy cake to go along with the pineapples and cherries. Unfortunately, I didn’t get to take a picture of a slice because it was all gone before I remembered.
The pineapple juice in the cake really adds a level of pineapple flavor to the cake so it’s not just a vanilla cake with pineapples and cherries. I also think pineapple juice helps retain the moisture in the cake.
My first trial came out too dense for my liking. The black sugar looking stuff also made the pineapples sour so there’s that too.
My second trial came out moist, but a little too soft to hold the pineapple and cherries when you flipped it out of the pan.
So, I basically started altering the second trial to see which ratio of ingredients gave me a strong, but bouncy cake as well as a nice subtle pineapple flavor. After several attempts I finally got it right. The recipe for the pineapple upside down cake is at the bottom of this post.
I have a whole bunch of recipes coming your way! For now, enjoy this pineapple upside down cake and see you soon!
Pineapple Upside Down Cake
20
minutes30
minutesIngredients
unsalted butter room temperature
eggs room temperature
granulated sugar
all purpose flour
baking powder
salt
vanilla extract
pineapple juice
pineapple slices
maraschino cherries
Directions
- Preheat the oven to 350℉. Prepare a 9-inch round cake pan with parchment paper or butter.
- Cake Batter
- In the bowl of a stand mixer, cream the butter and sugar until light and fluffy (about 1 minute).
- Add in the 2 eggs and combine.
- In a separate bowl, combine the flour, baking powder, and salt.
- In another bowl, combine the pineapple juice and vanilla extract.
- You will alternate between the flour mixture and the pineapple juice mixture. Add in 1/3 of the flour mix, then 1/2 of the juice mix, then 1/3 flour mix, then 1/2 juice mix, and finally the last of the flour and mix until combined.
- Brown Sugar Topping
- Melt the 3 tbsp butter and pour on to the bottom of the 9-inch pan.
- Sprinkle the 1/2 cup of brown sugar over the butter on the bottom.
- Place the slices of pineapple on the bottom (leaving room for the cherries in between.
- Place the cherries in between the pineapple slices and in the centers.
- Assembly
- Pour prepared batter over the brown sugar and pineapple topping.
- Bake in preheated oven for 25-30 minutes or until golden brown and an inserted tooth pick comes out clean.
- Let cool for 5 minutes before flipping over and enjoying!