Gluten free Pineapple Upside Down Cake

Gluten Free Pineapple Upside Down Cake Recipe

I’m all for the innovations in food that chefs come up with. I’m fascinated by the unusual flavor combos like pink peppercorn ice cream and the remaking of classic dishes.


However, some classics are classic for a reason; they invoke childhood memories, bring a sense of continuity and comfort in a world that changes at the speed of light, and, well, they became classic because they simply taste great!

Take pineapple upside down cake.  I have seen chefs and foodies attempt to make this classic cake “better” by grilling or roasting fresh pineapple, making a hard caramel that cracks like crème brulee topping and adding “interesting” ingredients to update this time-honored favorite.

While I am sure that roasted or grilled fresh pineapple or expensive rum may add something to the cake, I have to say when I eat a slice of pineapple upside down cake I want it to remind me of the way my grandmother made it – with perfect slices of canned pineapple, brown sugar, and bright red maraschino cherries that create a stained glass effect on the top of the cake.  I want the cake to be moist and light, but not too light. I want to be transported to a time when my family sat around my paternal grandparents’ dining room table, catching up, telling old stories (for maybe the hundredth time), and having the sense of belonging to something much greater than myself.

I guess this is just another reason why I am not really cool enough to be considered a “foodie.”

The only updates I have made to my grandmother’s pineapple upside down cake is to make it gluten-free (using my gluten-free flour) and to use pineapple slices canned in pineapple juice instead of heavy syrup. I also chose to use organic butter, organic eggs, and organic sugars (I used Wholesome sugars). And because my grandmother loved me and would above all else want me to remain free from harm, I know she would approve.  To make this cake dairy-free, substitute the butter with a good-quality non-dairy butter substitute, like Earth Balance.

Gluten free Pineapple Upside Down Cake Recipe

4.34 from 9 votes
Gluten free Pineapple Upside Down Cake
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Gluten Free Pineapple Upside Down Cake Recipe

Prep Time25 mins
Cook Time45 mins
Cool time2 mins
Total Time1 hr 10 mins
Course: Dessert
Cuisine: American
Servings: 12 servings
Calories: 302kcal
Author: Gluten Free & More


  • 1 (20-ounce) can pineapple slices in pineapple juice
  • 7 whole maraschino cherries
  • cups gluten-free all-purpose flour blend (make sure it contains xanthan gum)
  • teaspoons baking powder
  • ½ teaspoon baking soda
  • ¾ teaspoon kosher or fine sea salt
  • 3 large eggs , separated
  • 1 cup Wholesome Organic Cane Sugar
  • teaspoons pure vanilla extract
  • ½ cup unsalted butter
  • 1 cup Wholesome Organic Brown Sugar (light or dark), firmly packed


  • Preheat the oven to 350 degrees.
  • Drain the canned pineapple, reserving ½ cup of the juice. Lay the pineapple slices (you should have 10 slices) and the maraschino cherries on a layer of paper towel and pat them dry with another paper towel. Cut 3 of the pineapple slices in half.
  • Whisk together the gluten-free flour, baking powder, baking soda and salt in a large mixing bowl.
  • In a medium mixing bowl whisk together the egg yolks, granulated sugar, reserved ½ cup of pineapple juice and vanilla until smooth. Add this mixture to the dry ingredients and combine well.
  • With an electric mixer, beat the egg whites until stiff but not dry. Fold the egg whites into the batter, combining well.
  • In a 10-inch cast iron skillet, melt the butter over medium heat. When melted, carefully swirl the pan so that the butter coats the sides of the pan. Add the brown sugar and cook, stirring, until the sugar has melted into the butter and is lump free, about 1 minute.
  • Let the sugar mixture cool very slightly then lay in the pineapple slices carefully so you do not burn yourself. Start with the center, put one whole pineapple slice in the center then arrange the other six whole slices around it. Place the halve slices in the spaces between the whole slices around the outer edge, the curved side facing toward the center. Place a whole maraschino cherry in the center of each of the whole pineapple slices.
  • Pour the batter over the pineapples and cherries and bake for 40-45 minutes or until golden brown and a toothpick inserted in the center comes out clean.
  • Let the cake cool for 2 minutes, run a knife around the outer edge, then invert on a serving platter and let it finish cooling. Make sure you do not let the cake cool too long before inverting or the caramel will harden and the pineapple slices will stick to the bottom of the pan.


Nutrition Facts
Gluten Free Pineapple Upside Down Cake Recipe
Amount Per Serving
Calories 302 Calories from Fat 81
% Daily Value*
Fat 9g14%
Saturated Fat 5g25%
Cholesterol 61mg20%
Sodium 213mg9%
Potassium 148mg4%
Carbohydrates 54g18%
Fiber 2g8%
Sugar 42g47%
Protein 3g6%
Vitamin A 320IU6%
Vitamin C 4.5mg5%
Calcium 64mg6%
Iron 1mg6%
* Percent Daily Values are based on a 2000 calorie diet.

The views and opinions expressed on this blog are purely the blog owner’s. This blog accepts free manufacturers’ samples and forms of cash advertising, sponsorship, paid insertions or other forms of compensation. Affiliate links may be included in this post.

Disclaimer: All nutrition facts on Gluten Free & More are meant only as a guide and may differ depending on product brands used or ingredient substitutions. Some errors may occur, so you are encouraged to confirm the recipe’s ingredient and nutrition suitability for your own diet.
Have you tried this recipe? Give it a star rating and let us know your thoughts in the Ratings & Reviews section below.
Tags: Cake Cherries Dairy Free Old Fashioned Pineapple Upside Down Wholesome Sweeteners
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  1. Hänni
    August 2, 2010

    Carol, lovely cake. Not sure I can get in on the canned pineapple bandwagon (as opposed to fresh), but am glad for your traditional take. One of the best things about you is your lack of "foodie" pretension!

  2. sensiblecooking
    August 2, 2010

    That cake looks deliciously beautiful.

  3. sensiblecooking
    August 2, 2010

    That cake looks deliciously beautiful.

  4. Jam
    August 2, 2010

    ow, it looks so delicious.. that pineapple cake of yours looks fantastic.. pretty..

  5. Lisa (bakebikeblog)
    August 3, 2010

    What a beautiful cake! And I love that cake stand and server – they are both so elegant!

    August 3, 2010

    Carol, your pineapple upside down cake is just gorgeous. I like how you refer to stained glass, that paints such a pretty picture. By the way, I consider you a foodie……one with excellent taste. Your mom would be proud:)

  7. Kim - Cook It Allergy Free
    August 3, 2010

    Ahh! Carol, as if you haven't already, you just stole my heart even more! lol! The one dessert that i equate my grandma and my childhood to is her Pineapple upside Down cake. It was (and still is) one of my favorite cakes. All of my friends and family know this. A funny story…last summer, for my birthday, unbeknownst to each other, I had 3 different friends AND my mother-in-law all make me their own versions of this cake because they all know it is my fave!!! I actually got a little sick of it for a while (well, a very short while) because I ate so much of it during my bday week!
    Your recipe looks great – will definitely be trying it!

  8. Jenn/CinnamonQuill
    August 5, 2010

    Yes, this is such a classic. No need to mess with the classics! While I love all kinds of nuances and add-ins to make something extra special, I also love the basics. Nothing like 'em!

    Would it be alright if I featured one of these cake photos on my new site, It is kind of like Tastespotting, only gluten-free. Thanks, Carol!

  9. Carolyn - What Life Dishes Out
    August 15, 2010

    This looks delicious and it's been forever since I've had a pineapple upside down cake!! I bet I could also sub peaches instead of pineapple. I happen to have TONS of peaches that I need to do something with. Hmmmm….this just may be dessert tonight. :-)

  10. Bren
    August 15, 2010

    Okay i think i found the perfect recipe to make using your flour! Will be tasked for next week when I return to ATL! Yes, finally found what I wanted to make. This looks moist, which is what I look for!

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  12. Vicki Hibbs
    April 16, 2011

    OH….MY……GOSH………..I am floating in heaven~~~~~ Thank you ~Thank you~ Thank you!!!! This recipie was so easy to prepare and so delish!!!!

  13. A Marie
    June 10, 2011

    I would like to know if I can use another pan other than cast iron. I don’t have a cast iron pan.
    Thank you
    A Marie

    1. suzette
      April 18, 2012

      Just make the syrup in a saucepan and pour into a fluted flan tin or similar, it works for me

  14. suzette
    April 18, 2012

    This cake is delicious. I had to put in cherries in the gaps to make sure everyone got plenty! I have made this ahead and frozen it. I cooked it, turned it out when cool enough, washed out the pan and greased it. put the cake back in (upside down as when it baked the first time. covered with wrap and froze. the day i wanted it i got it out the freezer. let it defrost at room temperature for a few hours, pre-heated the oven to the original cake baking temperature and popped it in the oven 15 minutes before the end of the main course. i turned it out straight away and it was delicious, hot and no work on that particular day at all!

    1. Gluten Free & More
      April 18, 2012

      Wow – thanks for the tip. Great do-ahead advice. Glad you liked the cake, it is a family favorite around here!

  15. Charlene M.
    August 28, 2012

    Hi Carol, I’m new to your blog. I found you doing a search for some gluten free recipes. I found your GF Fried chicken recipe which led me to your GF Pineapple Upside down cake. Your link to the
    “Carol’s Amazing All Purpose Gluten Free Flour” is taking me to an ice cream recipe. Can you help me find the flour mixture recipe? Thanks so much!

  16. Karen Molloy
    November 10, 2012

    I made this cake today for guests, and it was FANTASTIC!! Even my non-gf guests thought it was the best cake they had had in quite a while!
    Thanks for the recipe!

    1. Gluten Free & More
      November 11, 2012

      You are very welcome Karen!

  17. Debbie N
    December 10, 2012

    Thank you for sharing EVERYTHING GF on your website. I made the pineapple upside down cake for my family and they loved it! (I’m the lone GF in my household.) I also made two batches of your baking flour (one for me and one for a GF co-worker). She made some awesome chocolate chip cookies with the GF flour – tastes like they’re made from regular flour…yummy! You have saved my Christmas baking season! Thank you!

    1. Gluten Free & More
      December 12, 2012

      Thank you Debbie! Happy Holidays to you and yours!

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  20. September 12, 2016

    On this recipe i have gluten free flour however i dont know that it has xantham gum so how much should i add?

    1. Gluten Free & More
      October 14, 2016

      Hello Violet,
      I would just add a teaspoon xanthan gum. Enjoy!

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  25. MassillonMaid
    September 13, 2019

    Carol, just came across the pineapple upside down cake recipe; thank you for that. The site displays the nutritional information: 300 calories per serving. However, it does not tell us how many servings are in the finished cake.. Thank you in advance for the additional information.

    1. Gluten Free & More
      September 16, 2019

      Hi there!
      The servings are listed towards the top of the recipe, underneath the prep time, cook time, etc. This cake serves 12.

  26. Jen
    September 13, 2019

    This sounds fabulous! And you’re right…don’t mess with the classics. It can be fun, I suppose, but in the end, just go with it, no matter how “squick” it man turn some people. They’re beloved for a reason! (And living in rural Ohio…believe me, canned is often the only way we can get the delectable pineapple into the house!)

    It’s kind of a shame I’m running across this so late on Friday…would be fun to bring to tomorrow night’s barn party! (Seriously.) Next year. ;)

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