Gluten Free Pineapple Upside-Down Cake

Gluten Free Pineapple Upside-Down Cake

Pineapple Upside-Down Cake is one of the most iconic desserts around. Which is one reason why I just had to make a gluten free Pineapple Upside-Down Cake a delicious reality.

The tradition of baking a cake with fruit on the bottom, which is then flipped onto a pan, dates back to early cast iron cooking over an open flame. But the first record of the ultimate fruit-on-the-bottom-flipped-upside-down cake — Pineapple Upside-Down Cake — is traced back only to the early 1920s.

gluten free pineapple upside down cake with cherries

An engineer employed by James Dole (of Dole canned pineapple fame) invented a pineapple slicing machine in 1911 and thus began the mass production of the perfectly round, lovely rings we all associate with this famous flipped cake, punctuated by bright red maraschino cherries, of course.

For my gluten free Pineapple Upside-Down Cake, I diverted a bit from the typical. One reason is that I had fresh pineapple and fresh is always best. I also happened at the market upon some delicious organic Rainier cherries (is there anything better than fresh-picked cherries?!).

gluten free pineapple upside down cake with cherry bowl

The taste produced by the happy marriage of these two fresh fruits is nothing short of delightful. I promise you that you will notice a difference when you skip the canned rings and sickeningly sweet maraschinos (for more reasons to avoid these high fructose corn syrup, Red Dye #4 soaked candied cherries, go here). Promise.

gluten free pineapple upside down cake whole

The resulting cake (or individual cakes) beckon with gorgeously natural pineapple rings, real cherries and a flavorful crumb that could only come from homemade. Arrange your fruits in any pattern you like — don’t feel bound by conventional rounds or perfectly spaced berries. Make it your own. Make it beautiful.

gluten free pineapple upside down cake

Whether you buy or make your own almond or gluten-free oat flour, using one of those flours in addition to the base of my gfJules Gluten Free All Purpose Flour makes this recipe healthier while adding a subtle, something extra to the flavor that I think you’ll really like. No oils in this recipe, either. You’re welcome.

Pineapple Upside Down CherriesBake in individual ramekins or one large round or rectangle — remember, it’s your own creation. And you won’t know just how lovely it is until after it’s baked and flipped, but the surprise will be worth it. I’d love to see your version, so drop me a line or leave a comment below; you may just provide inspiration for someone else’s Pineapple Upside-Down Cake!

Gluten Free Pineapple Upside Down cherry top

Gluten free pineapple upside down cake square

Gluten Free Pineapple Upside-Down Cake

Yield: One 9 inch cake or four ramekins
Prep Time: 30 minutes
Cook Time: 45 minutes
Total Time: 1 hour 15 minutes


  • (make your own)
  • 1 cup gfJules™ All Purpose Gluten Free Flour
  • 1 tsp. baking powder
  • ½ tsp. baking soda
  • ¼ tsp. salt
  • 1 cup light brown sugar + 3-4 Tbs. extra to sprinkle for topping
  • 5 eggs
  • 1/2 cup cream cheese, dairy or non-dairy – room temperature (Follow Your Heart®)
  • ½ cup vanilla yogurt, dairy or non-dairy (So Delicious®)
  • 2 Tbs. pineapple juice**
  • 1 tsp. pure vanilla extract
  • 1 handful pitted cherries (Dark Sweet or Rainier work well)
  • 1 fresh pineapple, cut into slices


Preheat oven to 350° F (static) or 325° F (convection).

Lightly oil, then sprinkle the bottoms of one 9 –inch round cake pan or 4 small ramekins with 3-4 tablespoons brown sugar.

Arrange pineapple rings to cover the bottoms of the pans and insert cherries into the centers of the rings or between rings in any decorative pattern.  Set aside.

In a large bowl, whisk together all dry ingredients including 1 cup brown sugar, then set aside.

Cut two other pineapple rings into chunks, then purée in a blender or food processor.  Remove 2 tablespoons of liquid and set aside. (Use any leftovers in a smoothie or fruity cocktail!)

In a large mixing bowl, beat the eggs until light, approximately 3 minutes.

Add the cream cheese, yogurt, pineapple juice and vanilla extract, mixing until well blended. Slowly add the dry ingredients, mixing an additional 2 minutes after all ingredients are combined. The batter will be smooth, but thin.

Pour the batter into the prepared cake pan(s), completely covering the pineapple rings and sugar.

Bake for 40-45 minutes for 9-inch pan or 30 minutes for small ramekins. Test with a toothpick or cake tester before removing from oven – continue cooking until tester inserted into the cakes comes out clean or with dry crumbs attached.

If the cake has mounded in the center during baking, lay a large knife on the top of the cake pan and saw gently across to evenly cut the bottom of the cake so it sits flat once inverted.

Invert cake(s) onto plates to cool (loosen with a butter knife around the edges) until the cakes drop.

Serve warm or cold.

I hope you love this recipe as much as we do!

Pin it for later!

This gluten free Pineapple Upside-Down Cake is magical! Fresh pineapple and cherries, moist yogurt and less fat: you'll wish you'd doubled the recipe!

This gluten free Pineapple Upside-Down Cake is magical! Fresh pinapple and cherries, moist yogurt and less fat: you'll wish you doubled the recipe!


gluten free pineapple upside-down cake
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Gluten Free Pineapple Upside-Down Cake
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48 thoughts on “Gluten Free Pineapple Upside-Down Cake

  1. I am so HAPPY to find your new site. I have been so angry at how your “partners” ripped you off. You seem to be doing even better with this site. A wealth of information and I can again get my favorite flour.

    Also, it works to go through Amazon as there is no hassle as previously about shipping to Hawaii.


    • Hi Ellie – Aloha to you, as well!
      I’m so glad you found my new site too!! We are definitely in a better place with my new company and website (so glad you like it!). We are happy to ship to Hawaii for you — just glad you’ll get your favorite flour back to do all kinds of yummy baking!!!

  2. Pingback: Gluten-Free Pineapple Upside Down Cake Recipes

  3. Pingback: Pineapple Upside Down Cakes! | All Gluten-Free Desserts...All the Time

  4. Oh, I’m going to try this. I actually just used my go-to pineapple upside cake recipe and Jules flour (with fresh pineapple) and it came out light and marvelous – rather like sponge cake. Hubby called it a ‘keeper’ and I can’t wait to compare it to your recipe. Thank you Jules!

    • Sandra, I totally understand! We have run nutritionals on some recipes, particularly my lentil recipes, but we don’t have anyone on staff who can run these for each recipe (and I definitely don’t have time!). It’s something I’d love to be able to offer, and hopefully in the future we can. In the meantime, all of my ebooks have the nutritionals run – why don’t you take a look at those?

  5. Yum! Not only does this look incredible but the picture is absolutely beautiful! Keep up the great work :)

  6. Pineapple upside down cake is one of my favorites! I’ve never thought of using ramekins and making individuals ones – great idea!

  7. I’m glad you came up with gluten free recipes like this Upside Down Pineapple Cake and others! Will make this real soon and can’t wait!

  8. By chance, have you made this recipe with Ener-G Egg Replacer? I generally have found that recipes with three or more eggs don’t transfer so well to egg free baking and was wondering if this would unfortunately be true in this case too. If you’ve got any other substitute ideas that are also gluten, dairy and egg free, I’d be interested.


    • Michele – I agree that 3 or more eggs to substitute doesn’t usually lend itself to a good result. If you have my newest cookbook, Free for All Cooking, I’d recommend making my egg-free cake and using some pineapple juice in place of some liquids, then doing the same pineapple/cherry rings and sugar topping. It’ll make a delicious, no compromise cake for you!

        • Rebekah – I wouldn’t recommend it with such a large proportion of this recipe being eggs. Even if you halved the recipe, the proportion of eggs would still remain the same. Of course you can always try it and prove me wrong though! ;)

  9. Oh my! My grandmother used to make a killer pineapple upside down cake. I can’t wait to make this gluten free version.

  10. If I have gf oats AND almonds, how do I decide which one to use? Can you please describe the difference, Jules? Thanks for the recipe – I’m so excited to try it!

    • Great question Stacy! To me, the almond meal/flour cake was more dense and had a slightly nutty taste and texture. The oat flour cake was lighter. I frankly couldn’t decide which I liked better, and the gluten-eating taste-testers at the party said they could barely discern a difference, but that they were both delicious! Let me know which you choose!

  11. Wow is all i can say. Great recipe. I had it with a caramel rum infused sauce and it was gf heaven! Thanks Jules ounce again you’ve outdone yourself!

    • Sue – I’ve found pineapples everywhere lately for only $2.99! That calls for several Pineapple Upside-Down Cakes, if you ask me!

  12. Oh, lovely, Jules! I think individual pineapple upside down cakes are super special. Kim made some a while back over at Cook IT Allergy Free. And, inspired by Kim, I made “medium-sized” pineapple cakes a little bit after that. I didn’t use fresh pineapple though … that really makes this recipe delectable, I’m sure. Love all the photos! I’m going to pretend this is a belated birthday cake for me, okay? ;-)


    • Shirley- absolutely. Since I didn’t get to make the Chocolate Beer cake for your birthday, you can count anything you want as my “virtual” cake for your special day, my friend! :)

  13. I love – love – love your flour and it is the only gluten-free flour blend I have purchased since I gave up mixing my own. Pineapple Upside-Down Cake is one of my favorites because we had it regularly when I was growing up. Needless to say, I haven’t had any since going gluten-free 6 years ago! However, I’m also limiting my dairy to low lactose and I’m allergic to soy. Is there something I can use in place of the cream cheese?
    Thanks so much!

    • Sharon – to replace the dairy or soy cream cheese, I’d suggest something like Earth Balance Mindful Mayo. The moisture levels will be different and the products won’t behave exactly the same, but it should still work for you, while being both dairy and soy-free. Let me know how it turns out – it’s an awesome cake, so I can’t wait to hear how you like it with the sub!

  14. Yummy! This is my husband’s fave. I’d love to make him individual cakes to take on the road! Thanks another great recipe, Jules!

    • Thanks Carla! I hope he enjoys it! I really had fun with the individual ramekins – they’re pretty and pretty handy! :)

  15. Tried your flour today for the first time. Made our favorite Chocolate Chocolate Chip Cookies. Turned out just like the originals in look and taste! Thanks.

    • Yay Jeanette!!! So glad you made truly amazing GF chocolate chip cookies with my flour! Life is too short to suffer through bad chocolate chip cookies, you know? Thanks for sharing & happy GF baking from now on!

  16. I LOVE Pineapple Upside Down Cake, but I haven’t had it since going gluten-free. Thank you for another fantastic recipe that uses my favorite So Delicious products in the ingredients, too! I cannot wait to make this! (More accurately, I cannot wait to eat it!)

    • Alaine, I love those So Delicious products – they’ve opened up so many dairy-free baking opportunities! Enjoy the recipe!

    • Same here Alaine! Thanks you for posting this. I missed pineapple upside down cake! Really looking forward to baking this!