I am sharing with you our family recipe for Pineapple Upside Down Cake. It’s not much different than many recipes I have seen over the years. However, there are a couple of different ingredients that make this cake FANTASTIC! Seriously, loved by everyone who eats it! My own son always states, “How is it that I don’t really care for pineapple, yet I LOVE this cake?!”
Step by Step Instructions~With pictures:
The directions in recipe format are included below, but I wanted to share step by step pictures. I think making a pineapple upside down cake for the first time (or if you don’t make it very often) can be a very intimidating recipe. It actually is much easier than most people think!
Start out preheating your oven to 350 degrees. Put a stick of butter in your 9 X 13 pan. Put in oven (you can do this while preheating) to melt.
While the butter is melting, I open the can of pineapple slices and strain over a bowl to reserve the juice for later. Let that sit while you are completing the next steps so it has time to drain sufficiently.
When the butter is completely melted, remove it from the oven.
Next, pour the brown sugar evenly over the melted butter. The recipe calls for about 1 1/2 cups of brown sugar. I play with this a little. I tend to use a bit more to make a thicker topping.
Now you will add the pineapple slices on top of the brown sugar mixture. If you want the cake to look more uniform, I would suggest using six pineapple slices. When making it just for my family I go ahead and cut the other slices in half to add them to the cake as well (this just doesn’t look as pretty if you do this, but gives your more pineapple.)
After placing the pineapple rings on the mixture, open the can of crushed pineapples and strain them over the same bowl. Once again, you are reserving this juice for later in the recipe.
While the crushed pineapple is draining, you will want to place cherries in the middle of the rings. ***Remember to place the cherries upside down so that when you turn the cake over it will look prettier to see the tops of the cherries.
Now it is time to add the crushed pineapple in all of the areas that are still exposed with the brown sugar and butter mixture.
Next you will blend the cake mix. (you can start this step earlier if you wish to have it blending while you are working on the topping. This will just depend on what method you use for mixing.) When I first started making this recipe (which was handed down by mom–which was handed down by her mom….you get the picture), I did not have a mixer. Thus, when I first began I followed the recipe directions in this order.
I use a yellow cake mix. You can make it from scratch, but seriously, you do not need to. If you follow these next steps, you will have a very moist cake that tastes delicious!
Follow the instructions on the back of the cake box ***EXCEPT***, substitute the reserved pineapple juice in place of the water. I laugh at this point, because my first time making pineapple upside down cake was a disaster. My mother told me to substitute the pineapple juice … so I did. However, I substituted it for the oil….not a good turnout! You still need oil!!!
After blending according to the directions on the box, you will layer the cake mix over the topping mixture.
Once you have poured all of the cake batter over the topping, you will bake at 350 degrees for 35-50 minutes. I understand that this is a very large amount of a time gap for baking. I initially set the timer for 35 minutes. This cake always takes longer than a simple cake mix. I then check it at 35 minutes (with the toothpick test) and then reset the timer at 5 minute intervals. PLEASE DON’T FORGET TO SET YOUR TIME EACH TIME YOU RESET! You have put a lot of work into this cake, so be careful to continue setting the timer.
Once the cake is done baking, remove from oven and let cool for about 5 minutes. While it is cooling, you need to get a long cake plate, cookie sheet or large tray in which to invert the cake on. In my example today, I covered mine in foil, as I was traveling with it and wanted to be able to secure it well for travel. I prefer to not use a foil liner as it is not as pretty.
When you are ready to turn the cake over, place your large tray over the top of the cake.
Carefully turn the cake over, while holding on to the tray underneath to flip.
Next, you will carefully lift the cake dish from the top of the cake You may need to let it sit for a minute for all of the topping to drop from the cake pan to the serving dish. I then use a butter knife to place gently under one edge of the cake pan to help lift the cake pan up and away from the cake.
And there you have it!!! A wonderful cake that has been a family favorite for years. It even makes it onto the birthday list many times!
Once you have tried this recipe, let me know how yours turns out!
Pineapple Upside Down Cake
- 1 Stick of Butter
- 1 Box of Yellow Cake Mix
- 1- 20 oz. can of Pineapple Slices in Heavy Syrup
- 1- 20 oz. can of Crushed Pineapple in Heavy Syrup
- 1 1/2 Cup Brown Sugar
- 4-5 Maraschino Cherries - cut in half
- 3 Eggs
- 1/3 Cup Vegetable Oil
- Preheat oven to 350 degrees.
- Place stick of butter in 9 X 11 baking pan and put in oven to melt.
- Drain both cans of pineapple ***Reserve the pineapple juice.
- After butter is melted, remove from oven. Spread brown sugar evenly over the melted butter. Place pineapple rings on top of brown sugar. Place cherry halves, upside down, inside each pineapple ring. Add crushed pineapple in all areas of brown sugar that is not occupied by pineapple rings.
- Mix cake batter, following directions on box EXCEPT for the water. Substitute the reserved pineapple juice for the water.
- Spread batter evenly over pineapples. Bake at 350 for at least 35 minutes. This type of cake usually takes longer than stated on box. Insert toothpick in cake after 35 minutes to check if cake is baked completely through. I usually have to bake mine for 40 to 55 minutes, however, I set the timer at 5 minute intervals to check. Each oven will vary.