Pineapple Upside Down Cake From Scratch

Friday, March 30, 2012
Pineapple Upside Down Cake From Scratch recipe is a favorite dessert recipe. The fresh pineapple on top and in the cake makes this the most delicious dessert recipe. This is always a favorite at Christmas from Serena Bakes Simply From Scratch.

I made a Fresh Pineapple Upside Down Cake the other day because they are so good! 

Is there anything better than pineapple and caramalley goodness topped with cake? There couldn't possibly be! I have been perfecting this for a while and oh my is it good. 

Pineapple Upside Down Cake is moist with a perfect crumb. Truth be told I could eat the ring all the way around the outside, then the pineapples, and cake by myself. I love the way the caramel and cake come together with the flavor of pineapple, and create a little crunch along the caramelized sugary edge..

Here's how to make Fresh Pineapple Upside Down Cake From Scratch.

Sliced Pineapple for Pineapple Upside Down Cake from Serena Bakes Simply From Scratch.

Remove the skin off the pineapple and cut out the core.

Slice in half and then slice each half into 1/2" thick slices.

Pineapple Puree for Fresh Pineapple Upside Down Cake from Serena Bakes Simply From Scratch.

 Place 1/4 of the pineapple into a blender or food processor.

 Puree the pineapple until smooth.

  • 6 tablespoons Cold Butter Cut into tablespoon sized pieces 
  • 1/2 cup Brown Sugar
  • 1/2 cup Granulated Sugar 
On medium until light and fluffy.

Add 2 whole Eggs and beat until combined over medium.

Pineapple Upside Down Cake From Scratch pineapple puree, baking powder, salt, and vanilla in mixing bowl.


  • 2 teaspoons Baking Powder
  • 1/4 teaspoon Salt
  • 2 teaspoons Pure Vanilla Extract
  • Pineapple Puree 
Beat until light and fluffy.

Flour added to Pineapple Upside Down Cake batter from Serena Bakes Simply From Scratch.

Add 1 1/2 cups All-Purpose Flour or Whole Wheat Pastry Flour.

Mix on low until just barely combined. You should still see flour.

Stir in 2 tablespoons Milk and mix until combined.

Set Pineapple Upside Down Cake batter aside.

For the Caramel Pineapple Topping in a heavy duty skillet mix together:

  • 6 tablespoons Butter
  • 3/4 cup Brown Sugar
Cook over medium. Stir to combined.

Stir and cook over medium heat until the sugar and butter become smooth.

Fresh Pineapple Slices arranged over caramel topping in Cake Pan for Pineapple Upside Down Cake.

Pour  caramel mixture into the bottom of a 9" by at least 2" deep cake pan that was greased with butter well. 

Place pineapple on top of caramel.

Pineapple Cake Batter over the top of caramel mixture and fresh pineapple slices.

Top caramel/pineapple mixture with cake batter and place into 350 degree preheated oven for 45 minutes or until a tooth pick inserted into the center of the cake comes out clean.

Baked Fresh Pineapple Upside Down Cake From Scratch in pan.

Allow to cool for about 8 minutes before inverting onto a cake stand or plate. 

If cake sits too long it will not release from the pan. Too short of a time and the caramel will run off the edge of the cake. I find 8 minutes is just right.

Fresh Pineapple Upside Down Cake from Scratch is a family favorite dessert recipe! This cake recipe is super popular at Christmas. Delicious with vanilla ice cream or plain from Serena Bakes Simply From Scratch.

 Serve warm or at room temperature with a big scoop of vanilla ice cream.

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Yield: 10

Pineapple Upside Down Cake From Scratch

Pineapple Upside Down Cake recipe from scratch using fresh pineapple from Serena Bakes Simply From Scratch.
4.75 out of 5 based on 8 user ratings
prep time: 20 Mcook time: 45 Mtotal time: 65 M


Pineapple Cake Batter
  • 1 1/2 cups Whole Wheat Pastry Flour Or All Purpose Flour
  • 6 tablespoons Butter, Cold Sliced 1 Tablespoon Pieces
  • 1/2 cup Brown Sugar
  • 1/2 cup Granulated Sugar
  • 2 whole Eggs
  • 2 teaspoons Pure Vanilla Extract
  • 2 teaspoons Baking Powder
  • 1/4 teaspoon Salt
  • 1/2 cup Pineapple Puree (Place remaining 1/4 Whole Fresh Pineapple into Blender Or Food Processor and Process Until smooth, Measure)
  • 2 tablespoons Milk
Pineapple Caramel Topping
  • 3/4 whole Fresh Pineapple, Core Removed And Sliced Into 1/2" Thick Slices
  • 6 tablespoons Butter
  • 3/4 cup Brown Sugar


How to cook Pineapple Upside Down Cake From Scratch

Pineapple Cake Batter
  1. Preheat oven to 350 degree's. Heavily butter a 9" by 2" deep cake pan. Set pan aside.
  2. In a mixer fitted with a paddle attachment add butter and both sugars.
  3. Beat on medium until light and fluffy.
  4. Add eggs, and mix till combined. Add vanilla, pineapple puree, baking powder, and sea salt. Beat on medium until light and fluffy.
  5. Add all of the flour. Mix until just barely combined on low ( you should still see flour). Add the milk and mix until fully combined. Set aside.
Pineapple Caramel Topping
  1. In a heavy duty pan add butter, and brown sugar. Stir until combined. Cook over medium heat, stirring until sugar becomes smooth.
  2. Pour hot sugar mixture into well buttered pan. Top with pineapple slices.
  3. Cover with cake batter and place into preheated oven.
  4. Cook for 45 minutes or until a wooden toothpick comes out clean.
  5. Allow cake to cool 8 minutes in pan before inverting onto a cake plate.
  6. Enjoy warm or at room temperature with a scoop of vanilla ice cream.
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Created using The Recipes Generator

Pineapple Upside Down Cake recipe from scratch using fresh pineapple is a favorite dessert recipe from Serena Bakes Simply From Scratch.

Pineapple Upside Down Cake recipe from scratch using fresh pineapple is a favorite dessert recipe from Serena Bakes Simply From Scratch.


  1. I love this cake and appreciate this recipe so much, Serena.

  2. I love pineapple! My Mom used to make this all the time! Would you consider sharing it over at my linky party?

  3. OMGoodness girl, this looks wonderful. I love pineapple upside down cake. Have a great weekend!

  4. WOW! Your pineapple upside down cake looks gorgeous! YUP, I agreed that pineapple and caramel makes a great combo ! One have to try it to believe as I did! I have to bookmark this recipe , looks really tempting!!! Have a wonderful weekend , Serena! :)

  5. See..when I saw the pureed pineapple, I was thinking 'take the container off of the machine, remove the blade and stick a straw in that baby'. This looks fabulous!

  6. I always eat the ring first too! lol This cake looks gorgeous, Serena! Great photo tutorial. So now I am virtually stopping by for a slice and a cup of tea :) Have a great weekend, my sweet friend! xoxo

  7. This sounds absolutely delicious! How I would love a taste right now!

  8. Delicious pineapple upside down cake! I can hear it calling my name!

  9. oh yum. how perfect is this cake?!
    thank you for your thoughts for me today. i appreciate you being my blogging friend.
    enjoy that delicious cake!!!!

  10. This looks so yummy! It's making me want some now! Maybe I should ask for this cake for my upcoming birthday. :)

  11. Beautifully done, Serena! I haven't had this cake since I was a was one of my dad's favorites :)

  12. This looks great! I'd love for you to stop by my party!!

  13. Visiting from Addicted to Recipes Sunday Link Party #5.

  14. Serena, I love the idea of using pineapple! Thanks so much for sharing at Mix it up Monday :)

  15. This looks simply devine! I have never tried making upside down pinapple cake from sratch (I am truly inspired now). I would love for you to link up at my linky party via: to share this recipe with my readers.

    Mrs. Delightful

  16. I love pineapple upside down cake - it ranks right up there on my favorite list with red velvet. I'm so glad you managed to get everything back together on your blog! I can definitely understand what you went through (happened to me once gah!).

  17. Serena...This cake looks delicious! Pineapple upside down cake is one of my all time favorites. Can't wait to try this...XoXo

  18. This sounds like it would be a hit at our house! Thanks for sharing at Scrumptious Sunday!

    Addicted to Recipes

  19. This is one of my faves......Thanks for linking up @CountryMommaCooks…..hope to see you again tonight and have a wonderful weekend:)

  20. This looks amazing, yum! :)

  21. My batter turned out pretty thick, should I just add more milk until it is the right consistency?

  22. The batter is a pretty thick batter! I would not worry as long as you have measured the other ingredients you should have a wonderful cake!

  23. I ended up using applesauce instead of the pineapple puree for 2 reasons, 1 my son begged me to cut up the pineapple for him to eat and 2 I felt a little lazy. But it turned out GREAT! Lots of mmmm's and YUM! So I definitely will be making this again. Thanks for a great recipe.

  24. Awesome, I love you, Serena!

    I was searching for a pineapple upside down cake recipe from scratch using a fresh pineapple. I was appalled at how many recipes include horrendous box cake mixes or instant pudding - all totally uncontrollable and GMO/Monsanto ingredients.

    I was delighted when I found you and this recipe. Now I can use all organic ingredients, Himalayan salt and Trehalose (the super brain sugar) for the white sugar, so it is as healthy, as is known at this point in time. I so appreciate you, thank you.

    This is my husband's absolute favorite cake.

    Wishing you every blessing, Michele

  25. Hi Serena,

    I Found your recipe and it is exactly what I was looking for. I thought that I would make a suggestion though. My grandmother, mom and aunts all do not use cake pans. They simply add the batter to the melted caramel and butter, in the cast iron skillet...the heat is already there and the caramel gets almost candy like slightly chewy, but not hard and crunchy. Today is my son-n-laws B-day and he will love this.

    Thanks and happy cooking :-)


  26. Saw this on your FB page, and came here for the recipe....I never thought of adding pineapple puree to cake batter before...and I can imagine how the cake must have tasted....bookmarking your cake and awaiting for pineapples to hit the market!!

  27. Oh. My. Gosh. A from-scratch pineapple upside down cake...with fresh pineapple. I'm pretty sure you have created the perfect version of this classic cake. I'm with you- I would probably enjoy the outer crusty, caramelized outer part, and then work my way in! ;)

    I am horrified by your blog/template/computer problems. It looks like you resolved everything beautifully, but what a nightmare. I have been thinking about getting an external hard drive to store blog posts on. I back my blog up, but like you said, you can run into problems even if you do backups.

    Glad it's resolved, and thanks again for the luscious cake!

    Love, Joy

  28. About to try this delish looking receipe! Thank you for sharing!


  29. Make sure you read the recipe carefully. Cake pan must be 2" deep. Most are only 1 1/2" deep like mine and it spilled all over the over. Other than that it was delicious although a bit sweet even for my sweet tooth.

  30. can you use unbleached AP flour instead of whole wheat?

  31. You definitely can NOT use a 1 1/2 inch high 8 or 9 inch round cake pan. It will overflow. I used a Pampered Chef pan that is much wider and it still overboiled a little. But it does look amazing. Will be tasting it tomorrow when I give it to my SIL for his birthday!

  32. Due to COVID-19, like everyone else, we are staying home. My husband absolutely loves pineapple upside down cake! So, I was excited to come across this beauty that I can make with ingredients I have on hand. With one exception...pineapple. All I have is canned; do you think I would still have success with puréeing a cam maybe drain it a bit and add the liquid back for consistency and then using rings in the bottom of the pan?

    1. Yes! Canned will work. Just make sure to drain the rings well for the topping. Is your pineapple in juice? If so I would do exactly what you said. If it's in syrup I would reduce the sugar a little in the cake some to account for the additional sugar in the juice. -Serena

  33. I just made this. It tastes fantastic but the cake part came out more like a biscuit texture. Very heavy and crumbly. I wonder what I did wrong? My batter looks darker and thicker than your photo.

    1. Hi Cindy! My guess would be the flour maybe was more compacted so it measured heavier. Fluffing the flour with a knife before measuring can help. You could add a little more milk next time to get the batter to a consistency similar to cake mix. Did you use the whole wheat pastry flour? Thanks, Serena

  34. Great recipe! I used Bob's Redmill 1-1 GF flour, and it came out nice and moist. I also put some mango in with the pineapple and it is super yum - also added fresh grated ginger to the melted brown sugar/butter mix but the flavor didn't really come through. The brown sugar on mine is chewy/crispy on some parts, mostly the edges, but not over the whole top. I used a 10" cast iron skillet, and I'm wondering if the butter mixture got too hot, or if I should have cooked it longer, or if it's better to use a 9"??? The fork came out clean at 45 minutes and I was worried about the bottom burning so I took it out. It's still DELISH and I'm trying not to eat it all right now!


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