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!

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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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46 thoughts on “Gluten Free Pineapple Upside-Down Cake

    • Hmmmm I wonder? Maybe a measuring issue? Are you scooping your flour using a measuring cup or spooning into the cup? Check out these gluten free baking FAQs and see if any of these apply to how you prepared ingredients for this cake. I’m assuming that you were using my gfJules Flour and no other substitutions were made with ingredients and your oven temperature has been checked recently?

  1. Used your flour, followed the directions exactly…and it’s PERFECT!!! It’s just like I remember. Thank you Jules for bringing this family favorite back!

  2. Hola from the land of enchantment Jules,
    I finally got the nerve to try baking this cake. While it was good l think I made a couple of mistakes. The cake was dense and the pineapples and cherries had no color, l think l over baked the cake. I use fresh pineapple and cherries and brought new baking soda and powder to have all fresh ingredients. I think l either added to much almond flour or beat the eggs too long. I didn’t have a scale to weigh the flour so l convert the 135 grams of the flour to cups (135 gram equal to one cup 3 tablespoons and 1/4tsp). Either way my cake turned out very dense. I read you guidance for baking at high attitudes because l live in Albuquerque (we’re at a high attitude here) and it mentioned not over beating the eggs which l think l did…oh well. I will be trying the recipe again with some minor changes. Now l just have get the nerve to start baking the bread and the many order goodies that you bake!!

    (PS…this is really my name????????)

  3. I was told to go gf while being treated for chronic Lyme so this is all new to me. It’s a tough world you live in, Jules you are a God sent! I was also told no sugar or dairy. I may still do the cream cheese but could I replace the brown sugar with coconut sugar?
    I also wanted to ask about programmable bread machines. I finally concurred healthy and yummy homemade bread for my family now I have to start again gf.

    • Hi Nancy,
      I truly hope the anti-inflammatory diet will help with your Lyme. I know that can be so painful and debilitating but the diet can provide at least some relief. As for this recipe, yes! You can absolutely use coconut sugar and all my recipes are written to be dairy-free, so I’d suggest looking for a vegan (dairy-free) substitute at the grocery store. There are several brands available now and you should be able to find one or ask your store to carry it for you.
      Regarding the bread machines, have a look at this review I did of a couple of my favorites — they both produce wonderful results and work really well with my bread mix (naturally gluten-free, dairy-free and sugar-free already). I hope that helps you get to enjoying yummy homemade GF bread very soon!!!
      All the best,

  4. I made this cake but since I cannot tolerate nuts or rice, I used my own flour mix and per Jules suggestion, I subbed white buckwheat flour for the almond. It turned out better than fabulous. The raw pineapple flavors the cake batter as it bakes giving you an awesome pineapple flavored cake throughout. Wonderful! Oh, I used Ranier cherries.