Gluten Free Pineapple Upside Down Cake Recipe
Updated May 08, 2025, Published Sep 10, 2019
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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.
Usually.
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
Ingredients
- 1 (20-ounce) can pineapple slices in pineapple juice
- 7 whole maraschino cherries
- 1½ cups gluten-free all-purpose flour blend, (make sure it contains xanthan gum)
- 1½ teaspoons baking powder
- ½ teaspoon baking soda
- ¾ teaspoon kosher or fine sea salt
- 3 large eggs, , separated
- 1 cup Wholesome Organic Cane Sugar
- 1½ teaspoons pure vanilla extract
- ½ cup unsalted butter
- 1 cup Wholesome Organic Brown Sugar, (light or dark), firmly packed
Instructions
- 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
Nutrition information is automatically calculated, so should only be used as an approximation.
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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!
That cake looks deliciously beautiful.
That cake looks deliciously beautiful.
ow, it looks so delicious.. that pineapple cake of yours looks fantastic.. pretty..
What a beautiful cake! And I love that cake stand and server – they are both so elegant!
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:)
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!
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, GlutenFreeFeed.com? It is kind of like Tastespotting, only gluten-free. Thanks, Carol!
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. :-)
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!