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
⅓ cup vegetable oil
1 tablespoon confectioners’ sugar for dusting, or as needed
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.
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.
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.
Pour batter into the muffin cups, filling them to the top; do not overfill.
Bake in the preheated oven until a toothpick inserted into the center of a cupcake comes out clean, about 20 minutes.
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.
Credit: All Recipes