Somehow we got on the subject of pineapple upside down cake in our household recently. I’m reminded of baby showers and 1950’s parties when I think about it. I haven’t eaten it since a baby shower years ago! Anyway, it sounded fascinating to our 4 year old and,  by golly, it just so happened that we had ALL of the ingredients except butter and rum! (I never run out of butter!) So I hit the store and then we rocked out this sweet cake, gluten-free style.

Gluten free pineapple upside down cake! Yum!

Perfect as a Hawaiian sunset, this cake uses fresh pineapples and cherries. I used Emeril Lagasse’s recipe, but substituted a few things:

Instead of using the 2 different flours, I used 2 cups of gluten-free “Pamela’s Products Baking & Pancake Mix,” which I buy at Target. I’ve made my own gluten free all-purpose flour mixes before, but I really do enjoy the convenience and the exceptional taste of Pamela’s. I also added 1 tsp of xanthan gum and sifted all the dry ingredients together. Finally, I substituted some praline pecans (candied pecans) instead of plain pecans. Everything else I did the same. You definitely need to do the alternating of the wet and dry ingredients. It makes for a lighter cake. OMG it’s soo delicious!

Looks like an alien, tastes like heaven. Gluten free pineapple upside down cake.

Pineapple upside down cake

Prep Time: 35 minutes

Cook Time: 45 minutes

Total Time: 1 hour, 20 minutes

Yield: 6 to 8 servings


  • 1/2 ripe medium pineapple, peeled, cored, eyes removed and sliced into 1/2-inch rounds (about 4 or 5 slices)
  • 3/4 cup (1 1/2 sticks) unsalted butter, room temperature
  • 3/4 cup light brown sugar
  • 14 praline pecan halves
  • 2 cups gluten free baking mix (I prefer Pamela's Ultimate Baking Mix found at Target of all places. It includes a variety of gluten free flours and baking powder, baking soda and xanthan gum)
  • 1/2 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/4 teaspoon salt
  • 1 cup granulated sugar
  • 2 eggs
  • 1 cup buttermilk
  • 1 1/2 teaspoons vanilla extract
  • 1 tablespoon dark rum
  • 4 fresh cherries, halved and pits removed


  1. Melt 4 tablespoons of the butter in a 10-inch cast iron skillet, over medium heat. Add the brown sugarand stir to combine. Increase the heat to medium high and cook until the sugar mixture is bubbly, about 2 minutes.
  2. Arrange pineapple slices in the skillet in a pleasing pattern and continue to cook for 2 minutes, or until the sugar mixture turns an amber color. Turn the pineapple slices over and remove the pan from the heat. (The mixture will continue to cook even though the heat is off.)
  3. Arrange the pecan halves in the spaces between the rings. Set aside to cool slightly.
  4. Preheat the oven to 375 degrees F.
  5. Sift together the flours, baking powder, baking soda, and salt in a medium mixing bowl.
  6. In the bowl of an electric mixer, cream together the remaining 1/2 cup butter and the granulated sugar until light and fluffy. Add the eggs, 1 at a time, mixing just until incorporated.
  7. Add the flour mixture and buttermilk alternately in 3 batches, mixing at low speed after each addition until just combined. (Don't skip this step!) Stir in the vanilla and rum.
  8. Spoon the batter evenly over the pineapple slices in the skillet. Bake in the middle of the oven until golden brown and a tester comes out clean, about 35 to 45 minutes.
  9. Cool the cake in the skillet on a wire rack for 4 minutes only. Run a thin knife around the edge of the cake and, wearing oven mitts and working quickly, invert the cake onto a cake plate, keeping plate and skillet firmly pressed together. Carefully lift the skillet off cake and replace any fruit stuck to the bottom of the skillet, if necessary. Arrange the fresh cherry halves, cut side down, into the top of the cake, in the center of the pineapple rings.
  10. Serve cake warm or at room temperature.

Pineapple rings with the center cut out
Arranged pineapples and pecans on top of butter and brown sugar

Sift dry ingredients together, then alternate wet and dry ingredients while mixing together.
Pour batter over the pineapple, pecans, brown sugar and butter in the cast iron pan.
Pit and cut fresh cherries in half.
Turn upside down onto serving platter after cooling for 4 minutes.

Gluten free pineapple upside down cake! Yum!