Fresh Pineapple Upside Down Cake From Scratch

Friday, March 30, 2012
Fresh Pineapple Upside Down Cake From Scratch
In celebration of my new web address  I made a Fresh Pineapple Upside Down Cake! 

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. The 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 edge..

This would have been posted earlier in the week but I was in a total state of melt down as I was playing around with the design of the blog when some how I managed to delete my template and anything that kept my blog functioning. After 2 days of stressing, worrying, and slaving I think I have it back to operational. There are still somethings I could improve but hopefully it works well for now. Please let me know if you notice any kinks I can try to resolve. I thought I was smart and backed up my template but for some reason it had an error I couldn't resolve so I had a total overhaul. I am just so thankful to be back to share this wonderful cake recipe with all of you and celebrate the new blog space.

Are you ready to make Fresh Pineapple Upside Down Cake From Scratch?

Remove the skin off the pineapple and the core.
 Slice in half and then slice each half into 1/2" thick slices.
 Place 1/4 of the pineapple into a blender or food processor.
 Puree the pineapple until smooth.
Beat cold butter and sugar on medium until light and fluffy. Add eggs and beat until combined over medium.
Add baking powder, salt, pineapple puree, and vanilla.  Beat until light and fluffy.
Add all of the flour and mix on low until just barely combined. You should still see flour.
Add milk and mix until combined.
For bottom of pan: In a heavy duty skillet mix butter and brown sugar together and cook over medium. Stir to combined.
Stir and cook over medium heat until the sugar and butter become smooth.
Pour  caramel mixture into the bottom of a 9" by 2" deep cake pan that was greased with butter well. Place pineapple on top of caramel.
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.
Allow to cool for about 4 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 4 minutes is just right.
 Serve warm or at room temperature with a big scoop of vanilla ice cream.

Yield: 10 ServingsPin it

Pineapple Upside Cake From Scratch

Pineapple Upside Down Cake recipe from scratch using fresh pineapple.
4.9 out of 5 based on 7 user ratings
prep time: 20 MINScook time: 45 MINStotal time: 65 mins


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 Sea 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
  • 7 tablespoons Butter
  • 3/4 cup Brown Sugar
  • 1 tablespoon Brown Sugar


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. Beat on medium until light and fluffy. 
  3. Add eggs, and mix till combined. Add vanilla, pineapple puree, baking powder, and sea salt. Beat on medium until light and fluffy. 
  4. 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. Cover with cake batter and place into preheated oven.
  3. Cook for 45 minutes or until a wooden toothpick comes out clean.
  4. Allow cake to cool 8 minutes in pan before inverting onto a cake plate.
  5. Enjoy warm or at room temperature with a scoop of vanilla ice cream.
fat (grams)
carbs (grams)
protein (grams)
sugar (grams)
Created using The Recipes Generator
Fresh Pineapple Upside Down Cake


  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 wonderful.Will try it out sometime

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

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

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

  16. 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

  17. 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!).

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

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

    Addicted to Recipes

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

  21. This looks amazing, yum! :)

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

  23. 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!

  24. 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.

  25. 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

  26. 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 :-)


  27. 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!!

  28. 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

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


  30. 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.

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


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