Pineapple Upside Down Cake Recipe

June 4, 2009 10 Comments

Pineapple Upside Down Cake Recipe

Pineapple Upside Down Cake

When I was a kid I was given my choice of cake my mom would make for my birthday. I’m not sure why but I always asked for pineapple upside down cake. It may be that I just liked the taste of pineapple with a classic yellow cake mix or it was the only cake my mom knew how to make. I’m not sure.

Yesterday was my birthday, and my 11 year old daughter asked me what kind of cake I would like.  I flashed back to when I was her age and requested pineapple upside down cake and sure enough she made it for me with very little help on my part. All I did was facilitate her getting the cast iron skillet into the oven, removing it and flipping it onto a plate. The rest she did herself with some additional help from her friend Duncan as in Duncan Hines Moist Classic Yellow Cake. I was impressed.

Now you can make your own cake batter from scratch, and I will post a recipe for that too but when in a hurry or are just a kid doing it for the first time, there is nothing wrong with a little commercial cake mix. It just cuts out a few steps and speeds up the process.

When my mom made her pineapple upside down cake, she used a rectangular bake pan and crushed pineapple but for this recipe, we used a large cast iron skillet and pineapple slices. My mom always served her pineapple upside down cake with real whip cream so I taught my daughter how to make it herself.

We prepared a great dinner of grilled steaks with a port wine demi glace sauce, steamed yellow squash and rice pilaf, but the highlight of the meal and the one that took me back to my childhood was the cake. It was a great night.

Important: Although my daughter prepared most of this cake by herself, I was still there watching what she was doing especially since she was working with the stove top and oven.

Pineapple Upside Down Cake Recipe

Prep Time: 30 minutes

Cook Time: 30 minutes

Total Time: 1 hour

Yield: 8-10 serving

Pineapple Upside Down Cake Recipe


2/3 cup butter

3/4 cup brown sugar

1 can of pineapple slices

Some maraschino cherries

1 box of your favorite yellow cake mix

To Make Yellow Cake from Scratch

6.5 oz. sifted cake flour

1 and 1/2 teaspoons baking powder

1/2 teaspoon salt

4 oz (1 stick unsalted butter) at cool room temperature

1 cups sugar

2 large eggs plus

1 teaspoons vanilla

1/2 cup milk (for pineapple upside down cake substitute pineapple juice for the milk)

How To Prepare At Home

I used a large cast iron pan because it is heavy and I can stick it into the oven without having to worry about it burning the bottom of the cake. You can prepare the topping in a sauce pan and transfer it to a cake pan with 2 inch high sides but then you have two pans to clean up.

1) Preheat your oven to 350°F degrees.

2) Heat your pan over medium heat, add the butter and brown sugar to it and let the brown sugar melt and the mixture start to boil. My daughter asked me how to measure out 2/3 cup of butter and I told her she can let it come to room temperature and use a measuring cup or look at the butter wrapper for the conveniently marked measurements. She opted for the second idea.

3) When the butter and brown sugar start boiling, remove from heat and start adding whole pineapple slices to the bottom of the pan. Cut some remaining slices in half and line the edge of the cast iron pan with the half pieces. Add some cherries to the holes in the whole pineapple slices and you are ready for the yellow cake batter.

4) Prepare the box of yellow cake mix following the directions on the box. The recipe my daughter followed called for three eggs and for some reason she only added two but the end result was fine. I'm not sure how the third egg would have changed the taste, but her version was delicious.

5) When the cake batter is ready, pour the cake mix into the cast iron pan and bake for the amount of time suggested on the cake box. You know it's done when you can stick a toothpick into the cake and it comes out clean. My daughter's cake took a little longer than the recipe said it would which is why the toothpick test is a better indicator.

6) When the cake is done, remove it from the oven and immediately loosen the side of the cake from the pan with a dinner knife and let it cool for a few minutes. Once cooled down some, place a plate on top of the pan and flip it over. It should come out easily looking delicious and ready to eat.

7) Whip up some homemade whip cream, add some birthday candles and you are ready to blow.

To Make Yellow Cake from Scratch

This cake is made using The Creaming Method, where fats are mixed with sugar to form a mixture that is either smooth and creamy (cookie dough) or light and fluffy (cakes).

1) Whisk the flour, baking powder and salt together really well. Set aside.

2) Whisk the vanilla and milk together and set aside.

3) In the bowl of a stand mixer fitted with the paddle attachment, cream the butter on medium speed. Add the sugar, and continue to cream until light and fluffy. Scrape the bowl as necessary.

4) Add each egg, one at a time, mixing on low to begin with and then increasing the speed to medium or medium-high. Scrape the bowl between additions.

5) With the mixer on the lowest speed, add half of the flour mixture. Beat until just incorporated.

6) Add half the milk mixture, and mix in on low speed. Scrape the bowl and mix for a few more seconds.

7) Add half of the remaining flour mixture, followed by the rest of the milk. Finish by adding the rest of the flour, and beat until just incorporated.

8) Spoon the batter evenly over the pineapple layer and smooth gently.

9) Follow the directions for baking pineapple upside down cake, above.

Last modified on Thu 17 July 2014 8:44 am

Filed in: Dessert Recipes

Comments (10)

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  1. Lilian .A.Onyango says:

    once i have my stove this will be the first cake am going to bake,i love pineapples and the cake makes my mouth watery and it looks yummy!

  2. kelly amirault says:

    I was planning on making something today, just not sure what! at midnite last nite hubby asked me if I could make a cake with pineapple slices…lol. So, this morning that is jsut what I did. It is awesome! I used a french vanilla mix tho(too warm to start from scratch today) and I decided to use a bundt pan just to be different. I cut the pineapple rings in half and molded them around the pan the tucked in cherries then the sauce and then cake! It is deeeee lish!!!

  3. RG says:

    Hi Kelly, glad it all worked out for you. It really is a simple recipe and “deeee lish”!

  4. dodie d. says:

    going to make this p.m. first time for me. I love these cakes!

  5. RG says:

    Great, let us know how it turns out for you. RG

  6. cherie connell says:

    I am really excited I just made this with a french Vanilla cake mix I have been craving it for some while it sure smells good! Thanks for the quick recipe.

    You are welcome cherie – RG

  7. stephanie says:

    did you know that there is now a cake mix for pineapple cake – duncan hines makes it! makes for a really great pineapple upside down cake. For added moistness and flavor, drain the pineapple and save the juice, add enough water to make the amount of water the cake mix call for and use this for the liquid. For years I have made the cakes with pineapple rings, but one time, i didn’t have anything but crushed pineapple, so that is what i used – the family loves it that way, you get pineapple in every bite of the cake! That’s the only way i make it now!

    Hi Stephanie, sounds good and thanks for sharing this information with us. – RG

  8. lizzy says:

    i ate one of those before! my family loves them.i was going to make one right now for an occassion,but i forget what the recipe was since it was a long time i had made one (about 2 years or so).anyway,thanks!!! :)lol

  9. Hapenny says:

    I had some time to make the cake so I marinated the pineapple in spicy rum and used the mixture of pineapple juice and rum to add to my cake mix. Used a mixture of dark cherries and marischino (sp) cherries and topped it with whipping cream. So good! Also, I agree that the pineapple upside down cake mix is good. Just make a few adaptations to it for my taste and used Irish Unsalted butter.

  10. CakenGifts says:

    Best Pineapple Cake ever…!!!

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