Fresh Pineapple Upside Down Cake

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Fresh Pineapple Upside Down Cake (traditional and gluten free recipes) by Barefeet In The Kitchen

Fresh pineapple is sliced thin and then baked in a caramelized brown sugar and butter sauce that soaks into a rich, buttery cake. This cake is like no other pineapple upside down cake you’ve ever tasted.

Pineapple has been in abundance all month and we’ve been eating it every chance we get. When my husband suggested a pineapple cake, I jumped at the chance to make something new.

My boys went a little crazy over this cake. Truth told, I sliced a wedge right before dinner, to take a photograph, and I wound up eating almost the whole slice as I was serving the dinner plates. It might have killed my appetite for dinner, but it was completely worth it!

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Enjoy the summer’s fresh pineapple with more great pineapple recipes:

Hawaiian Grilled Chicken Sandwiches

Pineapple Jalapeño Salsa

Roasted Sweet Potatoes with Pineapple

Pineapple Mojito Fruit Salad

Teriyaki Chicken with Pineapple

Pineapple Chicken Tacos

Fresh Pineapple Upside Down Cake (traditional and GF recipes) by Barefeet In The Kitchen

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Fresh Pineapple Upside Down Cake

4.80 from 5 votes
Recipe adapted from and with thanks to Gourmet via Smitten Kitchen
Prep Time: 15 minutes
Cook Time: 50 minutes
Total Time: 1 hour 5 minutes
Servings: 8 servings


  • 1 small pineapple peeled, quartered lengthwise, and cored
  • 6 tablespoons butter
  • ¾ cup light brown sugar
  • cups all-purpose flour*
  • 2 teaspoons baking powder
  • ¼ teaspoon kosher salt
  • 6 tablespoons butter softened
  • 1 cup sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • ½ cup unsweetened pineapple juice

*Gluten-Free Alternative

  • 1 cup brown rice flour
  • ½ cup tapioca starch
  • ¼ cup potato starch


  • Preheat over to 350°F. Cut the pineapple quarters into 1/3" thick slices. Combine the sugar and the butter in a saucepan (or cast iron skillet – see note), over medium heat. When the butter has melted, stir to combine and continue stirring while the sauce simmers for 4 minutes. When the sugar and butter have combined and are bubbly, smooth and thick, remove from the heat. Pour the caramelized sugar mixture into a 9" round pan, spread with a spatula to coat the bottom of the pan. Arrange the pineapple slices on top of the caramel in a single layer.
  • Whisk together the flours, baking powder, and salt. Beat the butter in a mixing bowl until light and fluffy. Gradually add the sugar, then the eggs, one at a time, beating well after each addition. Add the vanilla and half the flour mixture, beating on low speed just until blended. Add the pineapple juice, beat to combine and then add the rest of the flour, beating just until blended. (Batter may appear slightly curdled after adding the pineapple juice, it is fine.)
  • Pour the batter over the pineapple slices and spread evenly. Bake the cake in the middle of the oven, until the top is a deep golden brown and a tester comes out clean, about 45-50 minutes. (The cake should not shake or wobble when removed from the oven.) Let the cake cool in the pan for 5 minutes, before inverting a plate over the pan and then inverting the cake onto the plate, keep the plate and pan firmly pressed together while turning. Replace any pineapple that might have stuck to the bottom of the pan. Serve warm or at room temperature. Enjoy!


I made this cake in a 9″ round cake pan. It can also be made in a well-seasoned cast iron skillet. You can make the caramel in the skillet and then bake the cake in the same skillet.


Calories: 608kcal · Carbohydrates: 106g · Protein: 6g · Fat: 19g · Saturated Fat: 11g · Polyunsaturated Fat: 1g · Monounsaturated Fat: 5g · Trans Fat: 1g · Cholesterol: 86mg · Sodium: 237mg · Potassium: 426mg · Fiber: 3g · Sugar: 58g · Vitamin A: 651IU · Vitamin C: 56mg · Calcium: 98mg · Iron: 2mg
Tried this recipe?Mention @barefeetkitchen or tag #barefeetkitchen!

ONE YEAR AGO TODAY: 100+ Paleo Recipes

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THREE YEARS AGO TODAY: Homemade Vanilla Ice Cream

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Mary Younkin

Mary Younkin

Hi, I’m Mary. I’m the author, cook, photographer, and travel lover behind the scenes here at Barefeet In The Kitchen. I'm also the author of three cookbooks dedicated to making cooking from scratch as simple as possible.

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  1. Karen @ The Food Charlatan says

    This looks beautiful Mary! I love the thick pineapple slices. 1000 times better than the canned pineapple upside down cake i'm used to. And thank you for not putting maraschino cherries on this…they have their place in the world, just not on pineapple cake 🙂

  2. D Gideon says

    I wish I could post how beautiful mine turned out. Being diabetic I made this as sugar free as possible, using splenda-like sugar and the splenda-like brown sugar which is half the sugar of regular brown sugar plus you only use 1/2 what the recipe calls. For the liquid I used a little juice from the fresh pineapple and the rest milk. Sooo yummy, all things in moderation =) Thanks for the gr8 recipe.

  3. Vincy says

    Thank you so much for this recipe…our cake turned out as beautiful and yummy as you showed..our mom's bday turned out as a double treat with that cake…will bake more cake for more loved ones..Thanks once again for sharing this recipe.

  4. The Country Gourmet says

    Hello ! Thank you for this recipe. I am getting ready to make it and noticed it doesn't have any gums or psyllium in the recipe. Does this work without it and if so can you tell me why. I didn't see buttermilk or sour cream which I know when used sometimes eliminates the need for the use of gums in quick breads.

    • Mary says

      I've found that xanthan gum is not necessary in many baked goods. This recipe works beautifully without it. If you are leery of not using it, feel free to add a teaspoon of xanthan to the dry ingredients in this recipe.

  5. Alex says

    I used the Bob’s Red Mill 1 to 1 gluten free flour that I had but was short, so I added some tapioca flour and some cassava flour to make the 1 3/4 c. Batter was sooooo thick I added a little extra pineapple juice but it was still like rubber that had to be firmly spread over the pineapple. I didn’t have a 9 in pan so I used a 10 in springform pan… must not have latched it tight enough, cause it leaked quite a bit of the butter and sugar mixture. Still turned out very nicely, and I was lucky that I had been gifted a Maui Gold pineapple from relative who had visited Hawaii. I’m thinking that I would use the smaller pan next time, and less butter and sugar for the glaze base. It is plenty sweet enough with 1/3 to 1/2 of what I started with. I also cut the sugar with1/2 c stevia in the cake.

  6. Weiss girls says

    Just came across this recipe to use for leftover crushed pineapple from Thanksgiving. The cake is wonderful and tastes delicious days later heated up for 30 seconds after the fridge. Thank you!

  7. s says

    amazing recipe! it was a huge hit, I easily halved the sugar in the cake. The texture of the cake and the rise was so good. I am now making birthday cake with the same recipe.

  8. Janet Ritts says

    Loved the look of your lemon bars but no ingredient amounts were given. What am I missing. New to your website.

  9. Jill says

    I made this cake last night with some leftover pineapple that had been cut into small cubes and in the fridge for a day or two. It came out absolutely amazing! Seriously an awesome recipe especially that you can use fresh instead of canned pineapple 🙂5 stars

  10. meagan says

    I substituted almond flour for the brown rice flour and arrowroot starch for the tapioca because it’s what I had on hand. Swapped out 1/2 white sugar with monkfruit to lower the sugar content, and I probably could have done more without noticing if anyone is interested in lowering the sugar. It was superb! I used a spring-form pan, and the sugar/butter definitely leaked all over the sheet pan I put beneath it, so I recommend a different technique– but it did not take away from the flavor at all. So yummy! Thank you.5 stars

  11. Jill P. says

    Thank you for sharing this recipe, this is my favorite recipe for this type of cake! Definitely a staple cake for me…I always bake it gluten free since I have Celiac disease and it comes out flawless every time 🙂 The juice really makes the difference!5 stars

  12. Lori says

    I adore pineapple so I knew I had to give this a go. Boy am I glad I did! It’s divine. I’m not much of a baker, but this turned out fantastic. I will never buy a boxed pineapple upside down cake mix again! (And if I could bottle the smell in my house right now..😋)5 stars