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Gather all ingredients. 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.