A bright, sunshiny gluten free pineapple upside down cake, made with super flavorful pineapple slices in caramelized sugar that adds sweetness and zest to the buttery yellow cake below. Grab that can of pineapple slices, and let’s get baking!

What makes this gluten free pineapple upside down cake special

A tender and moist gluten free pineapple upside down cake that’s simply bursting with pineapple flavor, this cake is so impressive but almost couldn’t be easier. It comes out of the pan so readily, too, whether you use a classic round cake pan or a springform pan.

This isn’t just some yellow cake with pineapples on top. The bottom (which becomes the top, of course, then you turn it upside down) is packed with pineapple juice, maraschino cherries, and their juices are mixed with rich brown sugar and melted butter.

Our basic gluten free yellow cake mix is all we need for a buttery cake bottom that’s ready to soak up all those juices, and baked with some of its own.

The bottom layer, which becomes the top layer after baking and turning out, keeps the cake almost impossibly moist during baking and thereafter. Plus, the bottom-turned-top layer makes the cake look way more difficult than it actually is.

Baking this particular cake with pineapple juice in place of water or milk adds an acid that also helps keep this upside down cake especially tender.

Pineapple upside down cake on a white plate

Ingredients for a gluten free upside down pineapple cake

  • Sliced pineapple and juices – For this recipe, we need canned pineapple rings packed in their own juice. No sticky liquid with added sugars, please! And be sure to reserve the juice from the can when you remove the pineapple slices, since it goes into the cake base.
  • Maraschino cherries – I like to use Silver Palate brand maraschino cherries, since there are no dyes. The cherries are less unnaturally red, though, but they taste better.
  • Brown sugar – The brown sugar is combined with melted butter to make a grainy, delicious sugar paste that the pineapple slices are nestled into. It caramelizes in the oven and makes the pineapple slices heavenly.
  • Salt – Salt brings out the flavors of the dish, and balances the sweetness.
  • Unsalted butter – There’s melted unsalted butter mixed with brown sugar in this recipe, and then room temperature unsalted butter used in the yellow cake that forms the base of the upside down cake.
  • Gluten free flour – I like Better Batter’s classic all purpose gluten free flour blend here, since it makes a perfectly tender, but not overly fragile cake, that stays fresh for days.
  • Milk powder – Adding some dry milk to the cake adds the richness of milk without using milk as the liquid. That way, we can use pineapple juice that flavors the cake perfectly.
  • Baking powder and baking soda – These are the chemical leaveners that help the cake rise. Make sure they’re fresh, and measure carefully!
  • Granulated sugar – Sugar adds sweetness but also tenderizes the yellow cake base.
  • Eggs – Eggs add some rise and plenty of richness to your pineapple upside down cake. They also help bind the cake ingredients together.

Tips for making a beautiful gf pineapple upside down cake

Measure your gluten free flour like a pro

Measure your flour by weight, not volume, using a simple digital kitchen scale. Otherwise, you’re likely to overmeasure it, and end up with a stiff, dry cake.

Canned pineapple vs. fresh pineapple slices

I recommend only using canned pineapple slices that are packed in their own juice (not a sugary syrup), not fresh pineapple. Fresh pineapple may not be quite as ripe, fragrant, or sweet as canned, and we are asking a lot of each slice!

Blot your pineapple to prevent sogginess

We want the liquid from the canned pineapple slices in the base vanilla cake layer, but not on the top of the cake (which we bake as the bottom). Be sure to blot those slices dry with a paper towel lightly, to rid them of extra moisture without leaving behind any paper towel residue.

Choosing the right cake pan for an upside down cake

You don’t need to use a springform pan for this gluten free upside down cake recipe. In fact, I prefer using a standard cake pan since the smooth edges make for a cleaner release.

I’m also not really the biggest fan of springform pans in general. I have a super terrific the-Williams-Sonoma-salesperson-swore-it-was-the-best springform pan, and I still made a mess when I used it for this cake (okay, it’s really no different when I use it for anything else). The version in the standard 9-inch round cake pan was a much more relaxing experience overall, and it was still beautiful.

How do you get your pineapple upside down cake out of the cake pan?

If you’re afraid of upside down cakes because you’re just so sure they’ll never come out of the pan like they should and you’ll feel like a total failure (oh, wait—maybe that’s just me?), this is the upside down cake for you. It slips right out of the pan, and you feel like a million bucks. Trust me.

Don’t rush to flip your pineapple upside down cake

Be sure to let your cake cool in the pan, so it can firm up before you turn it over (or, you know, upside down). Otherwise, it may fall not make the trip in one piece!

Gluten Free Pineapple Upside Down Cake, Step by Step

How to store a gluten free pineapple upside down cake

Like any cake, this upside down cake is best the same day it’s baked. But it can be refrigerated for 24 hours if tightly wrapped with plastic wrap or in a tightly sealed container.

Can you freeze a gluten free pineapple upside down cake?

You can freeze a pineapple upside down cake, but the moisture in the cake may mean some ice crystals form on the pineapple. If it weeps at all as it cools, just blot it dry before serving it.

Gluten free upside down pineapple cake: substitutions

Gluten free, dairy free pineapple upside down cake

Try using coconut milk powder in place of the powdered milk in the cake batter, and vegan butter in place of the unsalted butter. My favorite brands of vegan butter are Melt and Miyoko’s Kitchen.

Gluten free, egg free pineapple upside down cake

To make this cake without eggs, try replacing the 2 eggs with 2 “chia eggs.” Place 2 tablespoons of ground white chia seeds in a small bowl, and mix in 2 tablespoons lukewarm water. Mix, and allow to gel before adding to the cake when you would add the eggs. You may see some flecks of chia seeds in the baked cake, but you won’t taste them.

A close up of a piece of pineapple upside down cake on a plate


Is pineapple gluten free?

Yes! Pineapple, the fruit, is naturally gluten free. Like any other naturally gluten free food, it is safe on a gluten free diet unless it’s contaminated with gluten-containing ingredients.

Is canned pineapple gluten free?

Yes, unless it’s a mixture of pineapple and something else gluten-containing, pineapple in a can should only have two to three ingredients: pineapple, pineapple juice, and maybe pineapple juice concentrate.

Is pineapple juice gluten free?

Yes, pure pineapple juice is gluten free. Enjoy it!

What’s the best gluten free flour for a pineapple upside down cake?

I like this cake with Better Batter’s classic gluten free flour blend, since it provides the best texture for this very moist, somewhat fragile cake. You can still use Cup4Cup gluten free flour blend, my other main recommended all purpose gluten free flour blend, which will make a slightly less sturdy cake.

Can I make a gluten free pineapple upside down cake with almond flour?

You can probably make a pineapple upside down cake using almond flour, but not using this recipe. This recipe must be made with an all purpose gluten free flour blend, not a single ingredient like almond flour.

Can I use pineapple chunks instead of slices for this gluten free pineapple upside down cake recipe?

You might be able to make this recipe using pineapple chunks if you use only the whole chunks from the can (not any crushed bits and pieces), and keep them from clumping together when you add the vanilla cake batter on top.

Can I use this recipe to make gluten free pineapple upside down cupcakes?

I’ve never made this recipe into cupcakes, and I honestly don’t know how it would work to divide the pineapples and cake batter that way. Maybe it’s possible if you use pineapple chunks, and place them on top, rather than on the bottom?

Why is my gluten free pineapple cake soggy?

Did you blot your pineapple slices dry, and measure your liquid carefully? You may not need all of the pineapple juice from the can.

Can I flip my gluten free pineapple upside down cake when the pan is still hot?

No, you definitely want to wait until the cake has cooled down before turning the cake upside down, or it won’t turn out in one piece. If the pan is still hot, the cake is still hot.

Gluten free pineapple upside down cake recipe


Classic Gluten Free Pineapple Upside Down Cake

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Use this gluten free pineapple upside down cake to make a classic treat for your family. This gf upside down cake looks like hard work, but it's so easy.
Course Cake, Dessert
Cuisine American
Keyword gluten free pineapple upside down cake
Prep Time 20 minutes
Cook Time 45 minutes
Resting time 30 minutes
Total Time 1 hour 35 minutes
Servings 1 9-inch cake
Author Nicole Hunn


For the pineapple layer

  • 1 20-ounce can sliced pineapple in its own juices
  • 7 maraschino cherries I used Silver Palate brand, which has no dyes and no preservatives (optional)
  • ¾ cup packed light brown sugar
  • teaspoon kosher salt
  • 6 tablespoons unsalted butter melted

For the cake batter

  • 1 ½ cups all purpose gluten free flour blend (I used Better Batter; please click thru for details on appropriate blends)
  • ¾ teaspoon xanthan gum omit if your blend already contains it
  • 7 tablespoons milk powder nonfat or whole milk
  • 1 teaspoon baking powder
  • ½ teaspoon baking soda
  • ¼ teaspoon kosher salt
  • 1 cup granulated sugar
  • 8 tablespoons unsalted butter at room temperature
  • 2 eggs at room temperature, beaten
  • cup pineapple juice at room temperature (See Recipe Notes)


  • Preheat your oven to 350°F. Grease a 10-inch cast iron skillet, 9-inch round cake pan or 9-inch springform pan and set it aside.

Prepare the pineapple layer.

  • Remove the pineapple slices from the can and blot them as dry as possible with paper towels. Reserve the juice from the can for the cake batter.
  • Remove the cherries from the jar, remove any stems and blot them dry as well.
  • Place the brown sugar and salt in a medium-size bowl and mix to combine. Add the melted butter, and mix until a thick, grainy paste forms.
  • Transfer the brown sugar and butter mixture to the prepared baking pan, and spread into an even layer with a spoon or small offset spatula.
  • Place one pineapple ring in the very center of the pan, on top of the brown sugar mixture. Arrange as many more of the pineapple rings in a single layer around the center ring as possible without overlapping them at all.
  • Slice the remaining pineapple rings into quarters and arrange the pieces in gaps between the rings and along the edges of the pan, climbing up the sides.
  • Place a maraschino cherry in the center of each whole pineapple ring. Set the pan aside.

Make the cake batter.

  • In a large bowl, place the flour, xanthan gum, milk powder, baking powder, baking soda, salt, and sugar, and whisk to combine well.
  • Create a well in the center of the dry ingredients and add the butter, eggs and pineapple juice, mixing to combine after each addition. The batter should be thick but smooth.
  • Scrape the batter into the baking pan on top of the pineapple layer and spread into an even layer with a wet spatula, taking care not to disturb the pineapples or cherries. If using a springform pan, wrap the bottom tightly with heavy-duty aluminum foil as it will leak during baking.

Bake the cake.

  • Place the pan in the center of the preheated oven and bake until a toothpick inserted in the center of the cake (but without reaching all the way to the pineapple layer on the bottom) comes out with a few moist crumbs attached (about 45 minutes, less for a cast iron skillet).
  • Remove the cake from the oven and allow to cool in the baking pan until cool to the touch (at least 30 minutes).
  • Invert the cooled cake onto a serving platter, removing the pan (or springform pan bottom) slowly so as not to disturb the pineapple layer. The cake should come out of the pan readily.
  • Allow to cool completely before slicing and serving.


About the pineapple juice.

The pineapple juice you use in this recipe is reserved from the pineapple slices, with water or more juice added as needed to make the proper volume.

Cake concept/method from allrecipes.com. Cake batter adapted from my Gluten Free Make-Your-Own-Vanilla-Cake-Mix recipe.

The post Classic Gluten Free Pineapple Upside Down Cake appeared first on Gluten Free on a Shoestring.

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