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.
Developed centuries ago, this classic cake has stood the test of time.
These 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!
This delicious dessert consists of a fluffy white vanilla cake made with fresh pineapple, brown sugar and butter for the caramelization.
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 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.
This awesome cake deserves to be put on a pedestal. 😉
Use any 8 Inch baking pan that isn't a springform pan.
Lesson learned when you make these types of upside down cakes because 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. 🙂
Bake it in a regular 8" buttered cake pan to get ultimate results.
I love bringing back classics and these cakes are not as hard to make as you would think.
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.
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.
Let's Party!
You might love these cake classics too!
Super-Moist Chocolate Cake with Chocolate Buttercream Frosting
Ultimate Carrot Cake
Pumpkin Magic Custard Cake
Decadent Red Wine Chocolate Cake
"American Beauty" Retro Red Velvet Cake
Streusel Coffee Cake Pound Cake
Dark Chocolate Texas Sheet Cake
Super-Moist Vanilla Cake with Vanilla Buttercream Frosting
Ultimate Fresh Pineapple Upside Down Cake
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 ⅓ inch thick
Vanilla Cake
- 1 stick (½ 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 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:
- 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.
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
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 🙂
Thank you so much!
Love pineapple upside down cake! This looks so yummy. Pinning!
Thank you so much Carole! You are so sweet! I hope you find lots of goodies! xo
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.
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.
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.
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.
Great to hear Sherry. I'm so happy you found it,tried it and loved it. 🙂 Thanks so much.
This is one of the best recipes I have ever found! The carmelization ofthe pineapple is key! Thank you soooo much for sharing! Yummy!!!!
Hi Sarah-Jane! It would be 1 & 1/2 cups of butter. Hope you enjoy!
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
I’ll use a 9” pan next time. The 8” makes a mess
So glad you enjoyed it Sherry! Thank you so much!!
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!
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!
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.
yessssss. i'm in love with upside down cakes and all that delicious gooey caramel <3
Aww thank you Liz! 🙂
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!!
Thank you Katherine! 🙂 So happy for you btw! Mama of 3!
That caramelization!!! Yum! This isn’t something I’d think to make, but now it will be!!
Omgosh, I forgot how much I loved this cake Leanne! It's definitely a keeper!! I hope you try it!
Thank you so much Maria! I love using the fresh fruits as much as possible too!
Thank you and yes 2 slices for you!! 🙂
thank you so much Annie!! 🙂
This is one of our all-time favorite cakes! That caramelization is everything!! Pretty photos, my friend! 🙂
The word ultimate says it all. This looks simply incredible! Two slices for me please!
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:)
This is truly the real deal Kim! Love that caramelization! I've never made a pineapple upside down cake, but now it is definitely on my list! Thanks for an awesome recipe!