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You are here: Home / Recipes / Cakes and Cupcakes / Fresh Pineapple Upside-Down Cake

Fresh Pineapple Upside-Down Cake

June 21, 2011 Updated April 4, 2023 14 Comments

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I have been lucky enough to visit Tahiti with my parents a few times.  On one particular trip we were staying on the island of Moorea, one of their friends owned a pineapple plantation and brought up a few pineapples for our breakfast.  I had never tasted pineapple so sweet and juicy.  It was like eating candy.  I told him that I was going to eat at least one pineapple a day while I was in Tahiti.  Later in the day he brought me a pineapple for everyday that I was going to be there.
My mother was kind enough to cut the pineapple for me every morning.  Which can be a time consuming event.  She had the system down and could cut a pineapple in just a few minutes.  After a few days my tongue was so sore.  That didn’t stop me.  I ate one pineapple everyday.
How I wish I had some Tahitian pineapple for my Dad’s father’s Day Dessert.

Let’s start with the brown sugar pineapple glaze.  We will put this layer on the bottom of the pan.  When the cakes is cooked it will be flipped over onto a serving platter.  So the bottom will then be the top.
You will need fresh pineapple, cream, butter, brown sugar, rum or rum extract and pecans.
Click here to see how to cut a pineapple.  Slice into 1/4-inch slices.  You can cut them thicker if you would like.
In a medium size sauce pan, melt the butter.
Add brown sugar.
And cream.
Bring mixture to a boil stirring constantly.
Add rum or rum extract.
You will need an 10-inch round…something.  I’m using a spring form pan.  A cast iron skillet works great, but mine isn’t quite big enough.
Butter the sides and bottom.  I’m lazy so I just sprayed with a non-stick spray.
Pour the brown sugar caramel glaze into the bottom of the prepared pan.
Cover the bottom completely.
Arrange the pineapple and pecans on top of the brown sugar glaze.  You can omit the pecans, but I love, love, love them.
I try to squeeze on as many pineapple slices and pecans that I can.
Set aside while you prepare the cake batter.
No I don’t use a cake mix…ugh.
You will need cake flour, sugar, butter, eggs, coconut milk, salt, baking powder and vanilla.
In a medium size mixing bowl whisk together the flour, salt and baking powder.  Set aside.
In a large mixing bowl, beat the butter and sugar together.
Beat for 3 minutes.

Add 1/3 of the flour and mix until well blended.  
Repeat until you have added all of the flour mixture.
Add the eggs one at a time beating well after each addition.
The mixture will be thick and creamy.
Add the coconut milk.  You could also use pineapple juice or just plain milk.
Add the vanilla and beat well.
Gently spoon the cake batter over the pineapple, pecans and brown sugar glaze.

Place in a preheated 350 degree oven for 40-45 minutes.
When the cake springs back after being gently touched, remove from oven and let cool for about 30 minutes.
Carefully invert the cake onto a serving platter.
I like to eat this cake warm with a scoop of coconut ice cream.

Fresh Pineapple Upside-Down Cake

Pineapple bottom layer:
1/4 cup (1/2-stick) unsalted butter
1/2 cup firmly packed brown sugar
2 tablespoons cream
2 tablespoons rum or 1 teaspoon rum extract
fresh pineapple, peeled, cored and sliced
1/4 cup pecan halves
Cake Layer:
2 cups sifted cake flour
2 teaspoons baking powder
1/4 teaspoon salt
1/2 cup (1 stick) unsalted butter
1 cup sugar
2 large eggs
2 teaspoons vanilla extract
1 cup coconut milk
Preheat oven to 350 degrees.  Butter a 10-inch cast iron skillet or spring form pan.  Set aside.
To prepare the pineapple bottom, place the butter, brown sugar and cream in a saucepan.  Bring to a boil and stir until smooth and creamy. Add rum or rum extract.  Pour brown sugar mixture into prepared pan.  Spread evenly over the bottom.  Arrange pineapple slices and pecans on top of the glaze.  Set aside.
To make the cake layer:  sift together the flour, baking powder and salt.  Set aside.
Cream the butter and sugar until fluffy, about 3 minutes.  Add 1/3 of the dry mixture at a time beating well after each addition.  Add the eggs, 1 at a time, beating well after each addition.  Add the vanilla and coconut milk  and beat well.  Pour the batter over the pineapple layer and smooth the top. 
Bake for 40-45 minutes or until deep golden brown and a toothpick inserted into the center comes out clean.  Cool for 30 minutes on a rack, then turn out onto a serving plate.  Serves 8-12.

My father is will be 79 in July, 2011.  He is still trying to return to Tahiti one last time to serve a mission.  My mother is resisting.  Perhaps he could just return for a 2 week vacation instead of an 18 month mission…with me!

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Filed Under: Cakes and Cupcakes, Dessert Tagged With: coconut, Dessert, pineapple

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Comments

  1. Ethnie wright says

    February 24, 2025 at 2:56 pm

    Not that you’d remember me, it’s been 25 years and i was pretty shy, But i went to a couple of parties in high school at your home. You always created such a fun, welcoming atmosphere with, of course, delicious food. While a few of your recipes have become birthday or holiday staples, the one that delights and surprises me every time we make it is this pineapple upside down cake. We’ve made this cake over the last few years. Last night my kids made it. It was amazing!! Thank you for the pictures and walking us through each of your recipes. You’re now teaching my kids to bake! All the best!!

    Reply
    • Janet Barton says

      March 14, 2025 at 9:51 pm

      Hi Ethnie, Of course I remember you. You’re sister as my son Ryan to a dance (Poor girl). We have so many great memories of the parties and crazy teenage nights in our home. It was so much fun having so many wonderful teens hang out!
      I’m so impressed that you are teaching your children how to cook. Bravo! I haven’t made the pineapple upside down cake for years. I need to make it again. It is one of my dad’s favorite treats! Thank you so much for your kind comment. You made my day!

      Reply
  2. Anonymous says

    May 23, 2014 at 12:49 pm

    I made this cake yesterday – followed the recipe exactly (except I added a few cherries for the classic look) – and it was amazing! Thank you so much for posting the recipe. It was easy to follow and a huge hit with all of my dinner guests! I am eating a piece for breakfast with my coffee right now – melt in your mouth delicious!

    Reply
    • Janet Barton says

      May 24, 2014 at 2:43 am

      I was just wondering if anyone knew this recipe existed. The photo's were taken in my early years of photography and they aren't the best, but the recipe is amazing! Thank you so much. Perfect breakfast cake.

      Reply
    • Anonymous says

      May 31, 2014 at 11:16 am

      I found the recipe because I specifically searched for "fresh pineapple" cake – and I picked it because your story was so cute and the instructions and pictures were great (I am the one who posted the comment last week). I am making this same cake again right now!!! I am actually going to try it in a cast iron skillet this time. I will let you know how it turns out.

      Reply
    • Janet Barton says

      June 1, 2014 at 11:34 pm

      I want to try it in a cast iron skillet as well. I'm so glad you found my site.

      Reply
    • Anonymous says

      June 3, 2014 at 4:28 pm

      Hello again. I tired the recipe in a cast iron skillet this time – it turned out great – but will give it a 9.5 instead of a 10 – only because a very small piece stuck to the skillet when I turned it out, it took a bit longer to cool and the pineapple layer didn't have quite as nice of a finish. I prefer the springfoam pan over the cast iron skillet. It was still excellent though! I checked out some of your other posts and yes indeed your photography has vastly improved – absolutely gorgeous! I can't wait to try some of your other recipes. Thank you for all that you do!

      Reply
    • Janet Barton says

      June 4, 2014 at 3:24 pm

      Great information. Thank you so much.

      Reply
  3. Anonymous says

    December 26, 2012 at 6:39 am

    I made this today for christmas. I have made many pineapple upside down cakes, and came across this recipe as I wanted a recipe that used coconut milk in the batter. This is definitely a winner! Good job! I will definitely use this recipe again. I did have a couple adjustments. I omitted the cream from the topping. I used blueberries instead of nuts. Also, I added cinnamon and dried cherries to the cake batter. Thank you for sharing. Pineapple upside down cake has to be my favorite cake.

    Reply
  4. Janet@simplysogood says

    August 1, 2011 at 4:35 pm

    Thank you anonymous. The correction is made. I'm so sorry for the mistake. It requires 1/2 cup butter. I really need to be better at proof reading.

    Reply
  5. Anonymous says

    August 1, 2011 at 12:44 am

    I was really excited to make this cake. And actually I am almost done. However in your cake recipe you forgot to include butter. So I am not sure how much to use. Please correct this error.

    Reply
  6. Janet@simplysogood says

    June 25, 2011 at 7:08 pm

    Oh you poor thing. I remember going one full week without keeping anything down. It was aweful. This will pass. Congratulations!

    Reply
  7. Amanda and Chase England says

    June 23, 2011 at 9:57 pm

    I have been morning sick and haven't desired food in about 5 weeks, but this cake has given me a craving!!

    Reply
  8. Martina(Dulce de Leche) says

    June 22, 2011 at 8:49 am

    Beautiful cake!!!yesterday I watched Desperate Housewives,and Bree baked same cake:))I must try it!!:)

    Reply

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