Pineapple Upside Down Cake, Gluten Free

Once upon a time I hated pineapple upside-down cake.  It tasted and looked like  Jiffy Mix met a can of sweetened pineapple, went out on a really bad date and fell into a deep dish, head first.

I’d forget after a while and make it again like it was something new and different.   And I still didn’t like it.  Even when I moved  past Jiffy Mix to decent yellow cakes, fresh pineapple and caramelized sugar, it still lacked something. Mostly it reminded me of school lunch fare.  Beige.

Still, I was hopeful that I might try just one more time (hope springs eternal or my brain is wired like Dilbert).  And I’m glad not only that I did, but had the foresight to write it all out as I was making it up.

This cake rocks.  I wanted to eat the whole thing in one sitting and had to actually psyche myself into leaving some of it for tomorrow – and for photos.

A splat of whipped cream on top is like dressing the thing up in couture, but more affordable.  The cake can be made in a single-ish bowl with just a whisk.  You don’t have to drag out the giant mixer and mess up every utensil known to woman.  You can make it at 5PM and eat it at 6PM.  And if you have a can of pineapple  (yep, back to the can) in juice – not syrup –  in the cupboard, chances are you have everything to make it with.  Really best served slightly warm.


Gluten Free Canteen Pineapple Upside Down Cake

  • handful of chopped pecans (optional, but tasty)
  • 2/3 cup brown sugar
  • large can of crushed pineapple drained
  • 4 tablespoons butter, melted  (topping)
  • 177 grams gluten free flour (20 grams almond flour plus 35 grams brown rice flour plus 55 grams potato starch and 67 grams gluten free oat flour) (about 1 1/2 cups)
  • 2 teaspoons baking powder
  • pinch baking soda
  • 1/2 teaspoon really good salt
  • 93 grams superfine white sugar (about 1/2 cup)
  • 6 tablespoons butter, melted (yes, again – for the batter)
  • 1 tablespoon of pineapple juice
  • 1 teaspoon vanilla
  • 1/2 cup of sour cream
  • 1 tablespoon buttermilk
  • 2 eggs

Preheat the oven to 350.

Butter an 8×8 or 9×9 square or round cake pan.

Place the pecans and brown sugar evenly over the bottom of the pan.  Melt 4 tablespoons butter.  Drizzle the butter over the sugar/nut mixture.   Add the pineapple on top and make sure to spread it to the edges.  Try not to move the bottom layers around after that.

Meantime, blend the dry ingredients together with a whisk which also lightens up the GF flour mixture.  Whisk the wet ingredients in a separate bowl (I use a large Pyrex glass cup and start with measuring the sour cream and then add the other wet ingredients).

Pour wet stuff into the dry stuff and whisk until mostly no lumps remain.  Spoon over the pineapple mixture.  Use a spatula to get every last bit.

Pop the pan on the counter to remove any air bubbles.  Place in the middle of the oven.

Bake at 350 for about 15 minutes and then crank the oven up to 375 degrees.  Bake for about 20 minutes more or until a toothpick comes out clean.  After 18 minutes keep an eye on it.

Remove from oven and get your serving plate ready.  Gently using a butter knife,  loosen the edge of the cake.  Using potholders, place the plate on top of the hot pan and in one single quick motion flip the whole thing.  Over the sink just in case….

Gently place on the counter and tap the pan with the butter knife to help it out onto the plate.  Carefully lift the pan (use those potholders if you don’t have fingers of steel) and take any remaining gooey pieces of the topping and just smoosh them back on the cake.  Don’t worry – while it is warm, you can fix all the blemishes if there are any.

Serve slightly warm with tons of whipped cream and prepare to swoon.

And as usual – if you make any of these recipes, or even if you make them your way (yay!) post a photo on the GF Canteen’s FB page here.



  1. You make me want to take up gluten free baking — just in case! Because none of your recipes seem limiting at all! I’ve never had a pineapple cake that wasn’t, as you say, “beige.” If you say this one is great, I believe you.

  2. I have never heard a cake described as beige kind of a funny way to describe but so true.
    We enjoy a pineapple upside down cake maybe once a year, just seems like a lot of work for a cake that usually only the hubby and I will eat. Going to give yours a go and see if the kids will try. Yours really doesn’t look like the beige cake we are used to 🙂

  3. This looks awesome!!

  4. I just made this cake and looks amazing. we just flipped it out of the pan and the look on our faces when it worked! We haven’t tried it yet, because it’s still too hot, but I am looking forward to trying it! 😉

  5. I’m assuming we don’t need to do the vanilla twice?

    • GlutenFreeCanteen says:

      indeed! only once. I’ll fix it. thanks for the catch.

      • Also you should get a hash tag for Instagram because that’s where I post pics of your stuff and would love to tag you. This was amazing by the way and you’re right, very difficult not to eat the whole thing in one sitting. I love your combo of flours that you do – things taste fluffy and not gritty and totally real instead of gluten freeish.
        I also tried making the crossaints but they were more like crescent rolls – flavor was amazing though.

      • GlutenFreeCanteen says:

        Hi Katy. Glad you liked the cake. It is really good, isn’t it?! So happy your tried the croissants. And no worries. After a few more tries they should be way closer to croissant than crescent. It is not easy to laminate dough with butter just right, especially a GF dough. But it will happen. It took me a few months to even get that far when I started. But it’s worth it. So glad you liked the flavor.

  6. chewtek says:

    Trying to pin recipes, but the pin button is not showing up on the pin photos. You have some very tasty looking recipes that I want to save and share.