Pineapple Upside Down Cupcakes


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

  • Step 1

    Move an oven rack into the middle of the oven. Preheat oven to 350 degrees F (175 degrees C).


  • Step 2

    Spray 24 muffin cups with cooking spray.

  • Step 3

    Line a work surface with waxed paper.

  • Step 4

    Spoon 1 teaspoon melted butter into the bottom of each sprayed muffin cup.

  • Step 5

    Spoon 1 tablespoon brown sugar in each muffin cup.

  • Step 6

    Press a maraschino cherry into the center of the brown sugar in each muffin cup.

  • Step 7

    Spoon a heaping tablespoon of crushed pineapple over the cherry and compact it with the back of a spoon into an even layer.

  • Step 8

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

  • Step 9

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

  • Step 10

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

  • Step 11

    Allow cupcakes to cool at least 5 minutes before inverting muffin cups onto the waxed paper to release. Serve with pineapple and cherry sides up. Sprinkle cupcakes lightly with confectioners’ sugar.

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