
I’m bringing you guys this Gluten Free Pineapple Upside Down Cake recipe right in time for Christmas. I made it for Thanksgiving and ate half the cake by myself. It was that delicious. Don’t judge me. This was my first time making a cake from scratch (aside from mini ramekin cakes), and I’m proud of the way it came out. I researched recipes to get an idea of the ingredients used. Then came up with my own recipe. I’m making some adjustments based on taste and sharing my recipe with you guys.

No one will know that this cake is gluten free unless you tell them. I used gluten free measure for measure flour just like in my Sweet Skillet Cornbread Recipe and there was no difference in taste. Speaking of skillets, I made my Pineapple Upside Down Cake in a cast iron skillet. Why? Because everything just tastes better in a cast iron skillet lol. Seriously though, the butter and sugar caramelized beautifully in the skillet. Just look at it!

A little note about the glaze- you can adjust the brown sugar range depending on your sweet tooth. I used 3/4 cups and found it to be a little too much. I think a half cup would be the sweet spot. No pun intended. But if you love you some sugar, then use the whole 3/4 cups. Enough talking though. Let’s get to this recipe. I even have a YouTube video for you guys featuring this cake and everything on this plate. So you have inspiration for a whole holiday meal. Enjoy!
Gluten Free Pineapple Upside Down Cake
Ingredients
Topping
- 6 tbs butter (salted)
- 1/2-3/4 cup dark brown sugar (packed)
- 20 oz can of pineapple slices (juice reserved)
- 7 maraschino cherries (stems removed)
Cake Batter
- 6 tbsp butter (salted, room temperature)
- 1 cup cane sugar
- 2 eggs (large)
- 1 tsp pure vanilla extract
- 1 1/2 cups gluten free flour
- 2 tsp baking powder
- dash of sea salt
- 1/2-3/4 cup pineapple juice
Equipment
Instructions
Topping
- Preheat oven to 350 degrees
- Melt the butter in a 10 inch cast iron skillet or cake pan.
- Add the brown sugar to the pan and simmer on low until the sugar melts into the butter. Stir constantly to avoid scorching.
- Remove the pan from the heat, and add the pineapple rings to the butter and sugar mixture. 7 rings should do the trick.
- Add a single maraschino cherry to the center of each pineapple ring.
- Set aside
Cake Batter
- Mix flour, baking powder and salt in a small bowl with a fork and set aside.
- In a large bowl, beat the butter until light & fluffy.
- Gradually add the cane sugar to the bowl and continue to beat until the mixture fluffs back up.
- Add the eggs to the mixture and beat until everything is well blended.
- Add the vanilla extract and continue to beat.
- Gradually add the mixture of flour, baking powder and salt to the bowl and beat on low speed.
- Add the pineapple juice to the bowl, starting with half cup. Beat until the batter is smooth and everything is well combined. Add a little more pineapple juice if the batter is too thick.
- Pour the cake batter over the pineapple topping, spreading evenly with a baking spatula.
- Bake the cake for 35-45 minutes until brown, and an inserted fork comes out clean.
- Let the cake cool for 10-15 minutes.
- Place a cake plate over the skillet and flip the cake onto the cake plate. Replace any topping stuck in the pan.