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Boozy Pineapple Upside Down Cake - Gluten Free

Vacation vibes with a dash of tropical is sort of where this boozy cake recipe is meant to take you. 
Prep Time15 mins
Cook Time1 hr
Total Time1 hr 15 mins
Course: Dessert
Cuisine: American
Keyword: gluten free cake, gluten free pineapple cake, pineapple cake from scratch, upside down cake
Servings: 8 servings
Calories: 359kcal
Author: Jen Pinkston


  • 4 eggs
  • 1 c coconut sugar
  • c crushed pineapple
  • c pineapple juice
  • 1 tsp vanilla
  • ½ tsp apple cider vinegar
  • c dark rum
  • 1 ¾ c gluten free all purpose flour blend
  • ½ c arrowroot flour or potato starch
  • 1 tsp baking soda
  • 1 ½ tsp baking powder
  • Pinch of salt
  • 3 tbsp coconut oil melted
  • 3 tbsp brown sugar
  • 6 pineapple rings
  • Real maraschino cherries cut in half


  • Preheat oven to 350 and pour melted coconut oil into a glass 9” baking dish.
  • Sprinkle brown sugar into the pan evenly over the coconut oil.
  • Add pineapple slices and cherries in the center of the pineapple slices and between them.
  • In a heavy duty mixer, combine sugar and eggs until mixed well.
  • Add remaining ingredients and mix well for at least 2 minutes*.
  • Pour the batter over the pineapple slices and bake for 55-65 minutes** Cover the cake with aluminum foil if the cake starts to get too brown.
  • When you pull your cake out run a knife along the outside edges. If your cake has slightly poofed at all on top, you can cut it to make an even surface for when you flip.
  • Watch for the liquid at the bottom to stop bubbling, then place your serving platter on top of the pan and carefully flip.
  • Allow to cake to release from the pan, you should begin to see the fruit pull away so can remove it.
  • Best served slightly warm. Top with a scoop  of vanilla bean ice cream if desired.


*Well mixed batter is key in gluten free cakes.
**Because there is a lot of liquid in this cake your best bet is to cook until a toothpick comes out clean, then cook for 5-10 more minutes. This will ensure it is baked fully and you don’t end up with a mushy texture.


Calories: 359kcal | Carbohydrates: 64g | Protein: 6g | Fat: 8g | Saturated Fat: 5g | Cholesterol: 82mg | Sodium: 326mg | Potassium: 161mg | Fiber: 4g | Sugar: 32g | Vitamin A: 164IU | Vitamin C: 9mg | Calcium: 96mg | Iron: 2mg