This gluten free pineapple upside down cake is soft, buttery, and loaded with caramelized pineapple on top. It tastes just like the classic version, and no one will ever guess it’s gluten free.

Pineapple upside down cake has always been one of those nostalgic, crowd-pleasing desserts. But if you eat gluten free, you probably haven’t had a good one in a while.

That’s exactly why I wanted to make this recipe. A version that’s simple, uses easy to find ingredients, and actually delivers on taste and texture.

The brown sugar and butter create this sticky, caramel-like layer on the bottom of the pan. When you flip the cake over, it becomes the most beautiful topping.

It’s a great dessert for a family dinner, a weekend treat, or anytime you want something a little special without spending hours in the kitchen.

Why You’ll Love This Recipe

It’s Gluten Free and Nobody Will Know – This pineapple upside down cake is so soft and moist that even your pickiest friends won’t be able to tell it’s made with gluten free flour.

That Caramelized Pineapple Topping Is Unreal – When the butter and brown sugar melt together under those pineapple rings in the oven, they create a sticky, golden caramel layer that looks and tastes absolutely incredible.

It’s a Total Showstopper – The moment you flip this cake over and reveal those perfectly arranged pineapple rings with bright red cherries in the center, everyone in the room is going to be impressed.

Uses Simple Pantry Ingredients – You don’t need anything fancy here, just basic baking staples and a can of pineapple rings, which means you can whip this up without a special trip to the store.

Ingredients

For the Topping

1/4 cup Unsalted Butter
2/3 cup Light Brown Sugar, packed
1 (20 oz) can Pineapple Rings, drained and patted dry
7 Maraschino Cherries

For the Cake

1 1/2 cups Gluten Free 1-to-1 Baking Flour
3/4 cup Granulated Sugar
1 1/2 tsp Baking Powder
1/2 tsp Salt
1/3 cup Vegetable Oil
2 Large Eggs, room temperature
1/2 cup Whole Milk, room temperature
2 tbsp Pineapple Juice (from the can)
1 tsp Vanilla Extract

How to Make

Step 1

Preheat your oven to 350°F. Place the unsalted butter in a 9-inch round cake pan and set it in the oven for a few minutes until the butter melts. Remove the pan, tilt to coat the bottom evenly, then sprinkle the light brown sugar in an even layer over the melted butter.

Step 2

Arrange the pineapple rings in a single layer over the brown sugar, fitting them snugly. Place a maraschino cherry in the center of each ring and in any gaps. Set the pan aside.

Step 3

In a large bowl, whisk together the gluten free 1-to-1 baking flour, granulated sugar, baking powder, and salt.

Step 4

In a separate bowl, whisk together the vegetable oil, eggs, whole milk, pineapple juice, and vanilla extract until smooth.

Step 5

Pour the wet ingredients into the dry ingredients and stir with a spatula until just combined and no streaks of flour remain. Do not overmix.

Step 6

Pour the batter gently over the pineapple arrangement in the pan, spreading it into an even layer.

Step 7

Bake for 38-43 minutes, or until the top is golden and a toothpick inserted in the center comes out clean. Let the cake cool in the pan for exactly 5 minutes, then place a serving plate on top and carefully flip it over. Lift the pan away and serve warm or at room temperature.

Helpful Tips

Pat the Pineapple Rings Dry

After you drain the pineapple rings, lay them out on a few layers of paper towels and pat the tops dry too. This step matters more than you’d think because extra moisture sitting between the fruit and the brown sugar will make the topping thin and runny instead of sticky and caramelized.

If the rings are still wet when they go into the pan, that water turns to steam in the oven and can make the bottom of your cake soggy. Take an extra minute here and you’ll end up with a much better looking and better tasting topping once you flip the cake.

Use Room Temperature Eggs and Milk

The recipe calls for room temperature eggs and milk for a good reason. Cold ingredients don’t blend together as smoothly, and with gluten free flour you really want everything to combine evenly so the texture comes out right.

If you forgot to set them out ahead of time, just place the eggs in a bowl of warm (not hot) water for about 10 minutes. For the milk, pour it into a microwave safe cup and heat it for about 15 seconds, just enough to take the chill off.

This small step helps the batter come together quickly so you don’t have to stir as much, which also helps you avoid overmixing.

Spread the Brown Sugar Evenly

When you sprinkle the brown sugar over the melted butter, take a moment to spread it into a flat, even layer using your fingers or the back of a spoon. If it clumps up in some spots and is thin in others, the topping will caramelize unevenly and some areas will be too dark while others barely have any flavor.

Make sure the brown sugar is packed when you measure it. Loosely scooped brown sugar gives you less than you need and the caramel layer will end up too thin to really coat the pineapple nicely.

Frequently Asked Questions

Can I use fresh pineapple instead of canned?

You can, but canned pineapple rings work better here because they’re uniform in size and thickness, which helps them fit neatly in the pan. Fresh pineapple also has more moisture and acidity, which can make the topping a bit watery and affect how the caramel sets.

If you do go with fresh, slice the rings about 1/4 inch thick, pat them very dry with paper towels, and keep in mind you won’t have pineapple juice from a can – so you’d need to squeeze a little juice from the fresh fruit for the batter.