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Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes

These pineapple upside down cupcakes are great to make for family gatherings or as treats to pack into lunches. It’s an easy recipe; adaptations can be made to make this completely from scratch. This is just a yummy simplified version!


  • cooking spray
  • ½ cup butter, melted
  • 1 ½ cups brown sugar
  • 24 maraschino cherries
  • 1 (20 ounce) can crushed pineapple
  • 1 (18.25 ounce) package pineapple cake mix (such as Duncan Hines® Pineapple Supreme)
  • 1 ⅓ cups pineapple juice
  • cup vegetable oil
  • 3 eggs
  • 1 tablespoon confectioners’ sugar for dusting, or as needed


  1. Preheat the oven to 350 degrees F (175 degrees C). Move an oven rack to the middle of the oven. Spray 24 muffin cups with cooking spray.

  2. Spoon 1 teaspoon melted butter into the bottom of each sprayed muffin cup. Spoon 1 tablespoon brown sugar into each muffin cup. Press a maraschino cherry into the center of the brown sugar in each muffin cup. Spoon a heaping tablespoon of crushed pineapple on top and compact it with the back of a spoon into an even layer.

  3. Mix pineapple cake mix, pineapple juice, vegetable oil, and eggs in a large bowl with an electric mixer on low speed until moistened, about 30 seconds. Increase speed to medium; mix for 2 minutes.

  4. Pour batter into the muffin cups, filling them to the top; do not overfill.

  5. Bake in the preheated oven until a toothpick inserted into the center of a cupcake comes out clean, about 20 minutes.

  6. Line a work surface with waxed paper. Allow cupcakes to cool at least 5 minutes before inverting muffin cups onto the waxed paper; serve with pineapple and cherry sides up. Sprinkle cupcakes lightly with confectioners’ sugar before serving.

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