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

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

Add 1 tablespoon brown sugar into each muffin cup and press a maraschino cherry into the center of the brown sugar in each cup.

Add a heaping tablespoon of crushed pineapple on top and compact it into an even layer using the back of a spoon.

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

Fill each muffin cup with the batter, 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.

Cool cupcakes for at least 5 minutes, then invert the muffin cups onto waxed paper. Serve with the pineapple and cherry sides up.