Pineapple upside down cupcakes are a delicious twist on the classic pineapple upside down cake. These cupcakes are made with a moist and fluffy pineapple cake base, topped with a rich and sticky pineapple glaze.

Pineapple Upside Down Cupcakes


  • ½C sweet cream butter, melted
  • 1 ½ C light brown sugar
  • 24 maraschino cherries
  • 1 can crushed pineapple, 20 oz
  • 1 package, 18.25 oz pineapple cake mix
  • 3 large eggs
  • 1 ½ C pineapple juice
  • ½ C canola oil
  • 1Tbsp powdered sugar, garnish

How to Make Pineapple Upside Down Cupcakes

  1. Position the oven rack in the middle of the oven.
  2. Preheat oven to 350 degrees.
  3. Prep muffin cups with nonstick baking spray.
  4. Add one teaspoon of melted butter in each of the muffin cups,
  5. Top the melted butter with one tablespoon of light brown sugar.
  6. Position one maraschino cherry in the center of the light brown sugar in each
    of the muffin cups.
  7. Use a tablespoon measuring spoon to measure out the crushed pineapple. (Heaping
  8. With the back of a spoon push down the crushed pineapple into the maraschino
    cherry/ brown sugar layer.
  9. Set aside.
  10. Add the pineapple cake mix to a mixer bowl. Mix in the eggs, pineapple juice,
    and oil with an electric mixer set on low until the cake mix is just moistened.
    (30 seconds)
  11. Increase the mixing speed to medium, mixing for 2 minutes.
  12. Scoop the prepared cake batter into each of the muffin wells. Fill just below
    the top of the muffin well. (Do not overfill.)
  13. Bake at 350 degrees for 20 minutes.
  14. Check to make sure the cupcakes are fully baked by inserting a toothpick in the
    center of the cupcake. If the toothpick comes out clean the cupcake is baked.
  15. Set the cupcakes on the counter to cool for about 5 minutes.
  16. Flip the baked cupcakes over on a cooling rack. (The cherry should be on the
    top of the cupcake.)
  17. Enjoy!

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Last Update: January 17, 2024