Preheat the oven to 350°F (175°C) and place a rack in the middle of the oven.
Spray 24 muffin cups with cooking spray.
Spoon 1 teaspoon melted butter into each muffin cup, followed by 1 tablespoon of brown sugar, and a maraschino cherry.
Spoon a heaping tablespoon of crushed pineapple and compact it into an even layer.
Mix pineapple cake mix, pineapple juice, vegetable oil, and eggs in a large bowl with an electric mixer until moistened.
Pour batter into the muffin cups and bake until a toothpick inserted into the center of a cupcake comes out clean, approximately 20 minutes.
Allow cupcakes to cool on waxed paper, then serve with pineapple and cherry sides up, lightly dusted with confectioners’ sugar.