Gluten Free Pineapple Upside Down Cupcake Recipe

12 Servings
45 min

This super easy pineapple upside down cupcake recipe will be the favorite in your home! We made it with Gluten Free cake mix.

Spray the cupcake pan completely covering all sides and bottom with nonstick spray.

Melt the butter and sugar in the saucepan until melted and combined. Do not let it burn. Use a nonstick saucepan if you have one.

Use the round already cut pineapple slices from a can because it works better and keeps the batter at bay in the extra large muffin tin. You will need 12 slices.

Add the melted mixture to the bottom of each cupcake and then add the pineapples and cherry. Press it into the sugar mixture. Then add the batter using a spoon.

When it is baked, it looks like this. Using the side of the knife, slide it around the edge of the cupcake which will loosen the cupcake to turn them over. Then, using a platter or cooking rack facing the cupcake pan and turn it over to release the cupcakes. If anything sticks, you can easily remove them from the pan and add it to the top of the cupcake. Let cool on a drying rack.

GLUTEN FREE PINEAPPLE UPSIDE DOWN CUPCAKE RECIPE Finish product - They turned out delicious and great for a party or a special evening with the family.

Gluten Free Pineapple Upside Down Cupcake Recipe
Recipe details
  • 12  Servings
  • Prep time: 15 Minutes Cook time: 30 Minutes Total time: 45 min
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  • 1 box Gluten Free yellow box cake mix
  • 1 jar of Maraschino Cherries
  • 2 cans of the Pineapple slices - cut out a little piece of fit in the cupcake tin
  • 1/3 cup Unsalted Butter
  • 2/3 cup packed Brown Sugar
  • 2 large non-stick Muffin Pans
Preheat oven to 350 degrees. Then, I sprayed each cupcake pan hole with a nonstick spray. Go up the sides so the cake doesn't stick anywhere.
Melt the butter and mix in the brown sugar in a saucepan.
Pour the brown sugar mixture into each muffin area evenly in all 12 large cupcake tins. Then, I added 1 pineapple (if it doesn't fit, cut out a little piece of fit in the cupcake tin) and 1 full-size cherry to each cupcake and pressed it into the brown sugar.
Follow instructions on the box and make the batter. With a large spoon, add the batter to the top of the pineapples and cherries. Slowly so the pineapples or cherry do not move inside.
Bake for 20-25 minutes or until the cake batter is not sticking to the toothpick. This is how it looks.
Let cool for 10 minutes and take a knife and separate the outer edge of the cupcake to separate from the pan.
Then use a cooling rack or platter and place the top over the muffin and turn it over. The cupcakes should fall right out.
Let cool completely or eat warm, your choice.
  • Use a traditional gluten-free cake mix, not almond flour-based. It will take heavy and will not be able to turn out from the pan properly.
Sabrina's Organizing
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    How do you use 7 pineapple slices in 12 muffin holes?

    • Sabrina's Organizing Sabrina's Organizing on Mar 18, 2023

      It was a typo. It should be 1 pineapple and I cherry in each hole of a jumbo muffin pan. I updated the recipe instructions. Thanks for catching that.

  • Cheryl Cheryl on Jul 04, 2023

    Goodness, I can’t believe I’ve never thought of making pineapple upside down cake as cupcakes! Thanks so much! I can’t wait to make these!