gluten-free pineapple upside down cupcakes |

Gluten-Free Pineapple Upside Down Cupcakes with Maraschino Cherry Frosting

The classic flavors of a gluten-free pineapple upside down cake simplified into a cupcake topped with a maraschino cherry buttercream frosting.
Course Dessert
Cuisine American
Keyword gluten-free cupcakes, gluten-free pineapple upside down cake
Prep Time 10 minutes
Cook Time 21 minutes
Total Time 31 minutes
Servings 12 cupcakes
Calories 268 kcal



  • box of your favorite gluten-free yellow cake I like Pillsbury gluten-free cake mix
  • 15 oz can of crushed pineapple in its own juice
  • 16 oz jar of maraschino cherries
  • brown sugar optional


  • 3 cups powdered sugar confectioners sugar
  • 1/2 cup 1 stick butter
  • 1/2 teaspoon almond extract
  • 1/4 cup maraschino cherry juice
  • red food coloring optional
US Customary - Metric



  1. Preheat the oven to the temperature listed on the cake mix. (Mine was baked at 350 degrees)
  2. Drain the pineapple, saving the juice in a separate bowl/cup.
  3. Chop one cup of cherries.
  4. Add the required ingredients for the cake mix. Using the pineapple juice in place of the water. If there is not enough pineapple juice, add water to the juice to achieve the proper amount. Mix until fully combined.
  5. Add the pineapple and cherries to the batter and mix until fully combined.
  6. Line cupcake pan with cupcake liners. You can also use cooking spray if you have not cupcake liners.
  7. Spray liners with cooking spray and sprinkle the bottom of the liners with brown sugar. (optional)
  8. Fill the cups with two scoops of cake batter. I use a cookie scoop.
  9. Bake according to the direction on the box of cake mix. (Mine cooked 21 minutes)


  1. In a standing mixer fitted with a whisk, mix together sugar and butter. Mix on low speed until well blended and then increase speed to medium and beat for another 3 minutes.
  2. Add almond flavoring and cherry juice and continue to beat on medium speed for 1 more minute.

Recipe Notes

Mama says, "Check all of your labels!"

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Nutrition Facts
Gluten-Free Pineapple Upside Down Cupcakes with Maraschino Cherry Frosting
Amount Per Serving (1 cupcake)
Calories 268 Calories from Fat 63
% Daily Value*
Total Fat 7g 11%
Saturated Fat 4g 20%
Cholesterol 20mg 7%
Sodium 70mg 3%
Potassium 51mg 1%
Total Carbohydrates 51g 17%
Dietary Fiber 1g 4%
Sugars 49g
Vitamin A 5.4%
Vitamin C 4%
Calcium 2.8%
Iron 1.6%
* Percent Daily Values are based on a 2000 calorie diet.