Fresh Pineapple Upside Down Cake

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This Ultimate Fresh Pineapple Upside Down Cake has caramelized fresh pineapple basking in a rich butter brown sugar gooiness atop a fluffy vanilla cake.  So much caramelized yumminess, it’s insane.

Perfect for Mother’s Day and summer dessert deliciousness! You may want to check out this Pineapple Coconut Banana Bread and this Heavenly Hash Pineapple Fluff Dessert too!

Fresh Pineapple Upside Down Cake recipe homemade

How Did Upside Down Cakes Come About?

Developed centuries ago, this Classic Pineapple Cake has stood the test of time. These kinds of cakes used to be cooked in cast iron skillets over an open fire. Then, fruit and sugar was added to the bottom of the skillet and cake batter was poured over the mixture.

Once cooked, flipping it over onto a plate not only released the cake from the skillet, but showed how pretty the caramelized fruit was on top.  Ta-dahhhh!

Fresh Pineapple Upside Down Cake recipe homemade

Why We Love This Fresh Pineapple Upside Down Cake!

  • I LOVE the Classic Desserts!  That’s why this awesome pineapple cake deserves to be put on a pedestal.
  • Got fresh pineapple? How can we resist it in this upside down cake recipe!
  • The caramelization of the pineapples and brown sugar and butter in the cake is amazing!
  • The hardest part is cutting up the pineapple!  Here’s how, but you can use canned pineapple, but we love the fresh pineapple idea!
  • Perfect summer baking dessert after dinner!
  • Impressive!

Ultimate Fresh Pineapple Upside Down Cake

This delicious upside down dessert consists of a fluffy white vanilla cake made with fresh pineapple, brown sugar and butter for the caramelization.

With this dessert recipe, you basically cook the fruit with the butter and brown sugar until tender and then place it in the bottom of your pan.  Make and dollop the cake batter on top and then smooth out. Bake away! Leave to stand for 5 minutes then turn out onto your platter.

But of course, if you don’t have fresh pineapple, you can absolutely use canned pineapple. I had a fresh pineapple on hand I bought at the grocery (ALDI) and have wanted to make this vintage recipe with them to put on the blog, so here we are.

Finally getting to it.  There’s like a million desserts I want to make, but this is one I definitely wanted to share with you.

Fresh Pineapple Upside Down Cake recipe homemade

Ingredients You Need

Bottom of Cake

  • brown sugar

Caramelized Fresh Pineapple

  • brown sugar
  • unsalted butter 
  • 1 large pineapple—peeled quartered, cored and sliced ⅓ inch thick (You may want to cut the pineapple up smaller if you want smaller chunks.)

Vanilla Cake

Fresh Pineapple Upside Down Cake recipe homemade

How to Make Pineapple Upside Down Cake

Pan Preparation

  1. Preheat the oven to 350°.
  2. Butter a deep dish 8-inch or 9-inch round cake pan. Sprinkle the bottom with 2 tablespoons of the brown sugar.

Caramelized Fresh Pineapple

  1. In a large skillet, combine ¾ cup of brown sugar with ½ stick of butter and cook over moderately low heat until the butter is melted. Add the pineapple and cook over moderately low heat, stirring occasionally, about 20 minutes or pineapple is tender. Using a slotted spoon, arrange the slices in the cake pan, overlapping them if necessary, then pour the pan juices over the pineapple, set aside.

Vanilla Cake

  1. In a medium bowl, whisk together the flour baking powder, baking soda and salt, set aside.
  2. In a large bowl, whisk together yogurt, eggs, vanilla, set aside.
  3. Using mixer, mix together the softened butter and sugar for 2 minutes on medium speed and then add in the yogurt/egg mixture and mix together.
  4. Add flour mixture to the yogurt mixture and mix just until combined and no lumps appear.
  5. Spoon the batter over the pineapple and spread it evenly.
  6. Bake for about 40 minutes, until the cake is deep golden. Let cool for 5 minutes on a rack. Run a knife around the edge of the cake, invert it onto a plate and remove the pan.Replace any pineapple that may have stuck to the pan. Serve warm or at room temperature.

Fresh Pineapple Upside Down Cake recipe homemade

Use Any 8 Inch Baking Pan that isn’t a Springform Pan

  • Lesson learned!  When you make these types of upside down cakes, Once things start heating up, that glorious butter brown sugar glaze is going to drip and spill in your stove and make a huge mess in your oven.  Then you’ll probably be mad at me.  So I’m letting you know it’s best not to use a springform pan if possible. 🙂
  • Bake it in a regular 8″ buttered cake pan to get ultimate results.

Ultimate Fresh Pineapple Upside Down Cake

Serve warm or room temp.  We love fresh whipped cream with cherries with ours, but you could add a yummy scoop of vanilla ice cream and caramel topping, whipped cream and a cherry to delight in the Absolute Ultimate Fresh Pineapple Upside Down Cake treat.

You may want to try this Pineapple Express Margarita too! 🙂  Let’s Party!

More Cake Classics!  

Ultimate Fresh Pineapple Upside Down Cake

Ultimate Fresh Pineapple Upside Down Cake

Kim Lange
This Ultimate Fresh Pineapple Upside Down Cake has caramelized fresh pineapple basking in a rich butter brown sugar gooiness atop a fluffy vanilla cake and it's INSANE!
3.89 from 34 votes
Course Dessert
Servings 12 Slices
Calories 157 kcal

Ingredients
  

Bottom of Cake:

  • 2 Tablespoons brown sugar

Caramelized Pineapple:

  • ¾ cup brown sugar
  • ½ stick unsalted butter softened
  • 1 large pineapple—peeled quartered, cored and sliced 1/3 inch thick (You may want to cut the pineapple up smaller if you want smaller chunks.)

Vanilla Cake

  • 1 stick (1/2 cup) unsalted butter very softened
  • ¾ cup granulated sugar
  • ½ cup Greek yogurt or sour cream
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1 ¼ cups all-purpose flour
  • ½ teaspoon baking powder
  • ¼ teaspoon baking soda
  • ½ teaspoon salt

Instructions
 

  • Pan Preparation:
  • Preheat the oven to 350°.
  • Butter an deep dish 8-inch or 9-inch round cake pan. Sprinkle the bottom with 2 tablespoons of the brown sugar.

Carmelized Pineapple:

  • In a large skillet, combine 3/4 cup of brown sugar with 1/2 stick of butter and cook over moderately low heat until the butter is melted. Add the pineapple and cook over moderately low heat, stirring occasionally, about 20 minutes or pineapple is tender. Using a slotted spoon, arrange the slices in the cake pan, overlapping them if necessary, then pour the pan juices over the pineapple, set aside.

Vanilla Cake:

  • In a medium bowl, whisk together the flour baking powder, baking soda and salt, set aside.
  • In a large bowl, whisk together yogurt, eggs, vanilla, set aside.
    Using mixer, mix together the softened butter and sugar for 2 minutes on medium speed and then add in the yogurt/egg mixture and mix together.
    Add flour mixture to the yogurt mixture and mix just until combined and no lumps appear.
  • Spoon the batter over the pineapple and spread it evenly.
  • Bake for about 40 minutes, until the cake is deep golden. Let cool for 5 minutes on a rack. Run a knife around the edge of the cake, invert it onto a plate and remove the pan.
  • Replace any pineapple that may have stuck to the pan. Serve warm or at room temperature.

Notes

Canned pineapple can be used as well.

Nutrition

Calories: 157kcalCarbohydrates: 38gProtein: 1gFat: 1gSaturated Fat: 1gSodium: 125mgPotassium: 49mgFiber: 1gSugar: 28gCalcium: 22mgIron: 1mg
Keyword cake, pineapple, summer desserts, vanilla cake
Tried This Recipe?Let us know how it was by commenting below!

33 Comments

  1. That is wonderful to hear Jo! I’m so happy you all enjoyed it for your husband’s birthday! Tell him ‘Happy Birthday’ from me and thank you so much for trying it!! xo

  2. Aloha Kim,
    I specifically sought out to find a recipe that used fresh pineapple rather than canned since I prefer fresh, and it’s what I had on hand. Thank you for taking the time to create and share this recipe. Yours is hands-down, the MOST delicious pineapple upside down cake I’ve ever had! This is my first time making one (my husband requested pineapple upside down cake for his birthday this year), yet it was simple to make, and we both really enjoyed it. I would make this recipe again 🙂

  3. My husband of 50 years always like me making a pineapple upside down cake, but I’ve never made one with fresh pineapple, but today is the day after finding this recipe. I’m giving you five stars without even a taste as I am quite impressed with your technique. So here goes. Will mark your blog and see what else you have going on. Thanks.

  4. Thanks Kim! I’m getting ready to make this now for a lunch get together at my dad’s tomorrow. I was worried I was missing something. Recipe looks delicious and I can’t wait to try it. I am in charge of dessert and wanted to make something with stuff I already had on hand. I found your recipe because I also had a pineapple from Aldi that I needed to use. Lol! This looks so much better than the overly sweet recipes using canned pineapple. I also love that the cake is from scratch and not a box mix since I never purchase those so none sitting around.

  5. No the center should not be wobbly, so it’s good that you put it back in the oven. It should be firm on top. I hope it worked out for you after putting it back in the oven Cindy.

  6. Hi, I’m just about finished baking, but the center is still wobbly after 40 minutes so ive put it back in for another 10. Is this a mistake? Not sure how these cakes bake.

  7. This is one of the best recipes I have ever found! The carmelization ofthe pineapple is key! Thank you soooo much for sharing! Yummy!!!!

  8. Hi, I’m making this cake today, very excited to try it! Would you please share what the measurements are for 1 stick and 1/2 stick of butter?
    Thanks & regards Sarah-Jane

  9. I have made some awesome recipes from Pinterest, but this one is the bomb!! The pineapple is to die for and the cake truly is insane! So glad I found you! Thank you for this incredibly yummy recipe!

  10. I’m so thrilled you enjoyed it Ravonda! I like the idea of cutting up the pineapple smaller like you did or even crush it up a bit for a different texture. Thank you so much for being so sweet!

  11. This turned out quite well. I was concerned that it could stick, so despite the warning not to use a springform pan, I went that direction anyway, but lined it with parchment paper and it worked beautifully. I followed the recipe except that I chopped my pineapple quite small before carmelizing.

    I loved the way you decorated it and did the same. The piped whipping cream gives it a wow factor and complements the cake well.

    This was a really good cake! Love that it uses fresh pineapple and isn’t a huge cake.

  12. These are the times I wish my hubby liked pineapple. This was one of my dad’s favorites–wish I could make it for him <3 Yours is gorgeous!!

  13. I love the use of fresh pineapple Kim. To be honest, I’m not a huge fan canned fruits and veggies. This is certainly a delicious classic and I so love the pretty pictures:)

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