Gluten-Free Pineapple Upside Down Cake


Lots of things look great up-side down.


Let’s see….this guy


Screw you, physics!

Screw you, physics!


This ambigram…

I’m such a hipster sign!

This cirque du soleil dancer….

Gravity defying guy: “Can you do that in YOUR Yoga class??” No one likes a show off, ya know.


And this Upside down Pineapple Cake! Talk about Up-side down Mojo.
pineapple upside down cake


I’ll let you in on a secret, I have totally been in a funk since letting our rescue dog go, and I figured when things feel upside down, maybe the best thing to do, is make some Upside Down Pineapple Cake! Desserts are great at patching up souls in my experience, especially when shared with friends over coffee. At a coffee shop known with hunky looking guys walking in every few minutes.

With maraschino cherries, brown sugar and buttery goodness, I was marooned like Tom Hanks in that movie, on a island of sugary, crumbly, pineapple-y benevolence. Did I mention this is gluten-free? It didn’t make me want to disavow “gluten free” baking or make me go “what on God’s earth is this??”. Actually, wait, it did make me say “what on God’s earth is this??”. It was super moist, easy to whip up and is incredibly satisfying.

pineapple upside down cake

pineapple upside down cake

pineapple upside down cake

Here’s the recipe for the “Upside Down Pineapple Cake…I can’t believe it’s gluten-free!”



Prep Time: 20 minutes

Cook Time: 50 minutes

Total Time: 1 hour, 10 minutes

Yield: 8 servings & fork-dropping goodness.


    For the Topping:
  • 1/4 cup melted butter
  • 1/2 cup brown sugar (trust me when I say don't use white sugar - you won't see the glaze!)
  • 10-12 slices canned pineapple, drained (don't chuck the juice just yet! You'll need it for the cake)
  • 12-15 maraschino cherries
    For the Cake:
  • 1 2/3 cup gluten free all-purpose flour, I prefer King Arthur's Gluten-Free Flour
  • 1/2 tsp baking powder
  • 1/4 tsp baking soda
  • 1/2 tsp salt
  • 1/2 cup melted butter
  • 3/4 cup brown sugar
  • 1/4 cup granulated sugar, aka white sugar
  • 1 egg
  • 1/4 cup vanilla yogurt (I used plain yogurt, that works fine too)
  • 1/2 cup milk, room temperature (for dairy-free version, use Cashew milk, it turned out pretty creamy!)
  • 1/4 cup pineapple juice (from the canned pineapple)
  • 1 tbsp pure vanilla extract (or you can use 1 vanilla pod & extract seeds)


  1. Preheat oven to 350 degrees F.
  2. Prep your topping: In a 8-9 inch pie pan (ensure your pan has depth), layer 1/4 cup melted butter and spread 1/2 cup brown sugar on top. Arrange the pineapple slices on the mixture, with the cherries in the open spaces between slices and inside the holes.
  3. Prep the cake: Start with the dry ingredients - In a medium bowl, whisk together the flour, baking powder, baking soda and salt.
  4. Now prep the wet ingredients - In a large bowl, whisk together 1/2 cup melted butter, 3/4 cup brown sugar and granulated sugar. Ensure there are no clumps. Add the egg, yogurt, milk, pineapple juice, vanilla extract.
  5. Add the dry ingredients to the wet mixture to make your cake batter.
  6. Pour the batter over the pineapple slices and bake for 45-65 minutes. You want to bake it until a toothpick comes out clean (or ghetto-style it like I do with a butter knife). If you notice the cake getting too brown, cover with aluminum foil.
  7. Cool cake in the pan for 15-20 minutes before inverting onto a cake plate.
  8. Serve warm or room temperature & it's ok to drop your fork in speechless glee.

Like this recipe or have something to add? Like or Comment below!

Also published on Medium.

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