Preheat your oven to 350°F (175°C). Prepare either 24 regular-size muffin cups or 12 larger muffin cups by spraying them with cooking spray.
Cut each pineapple slice from the can into 4 pieces and set them aside.
In a large mixing bowl, combine the cake mix, vegetable oil, eggs, and the reserved pineapple juice. Use an electric mixer on low speed for 30 seconds, then switch to medium speed and beat for an additional 2 minutes, scraping the bowl occasionally.
In a separate small bowl, stir together the melted butter and brown sugar until well combined.
Spoon 1 1/2 teaspoons of the butter-sugar mixture into each prepared muffin cup.
Place two pineapple pieces on top of the butter-sugar mixture in each cup, and then add a halved maraschino cherry, cut side up, in the center.
Spoon 1/4 cup of the cake batter into each muffin cup, covering the pineapple and cherry.
Bake in the preheated oven for 20 to 25 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
Allow the cupcakes to cool in the muffin tin for 5 minutes, then run a knife around the edge of each cupcake to loosen them. Invert the muffin tin onto a cookie sheet to release the cupcakes, allowing them to cool slightly before serving.
For a larger batch, simply modify the recipe to use a 12-muffin pan.
Conclusion:

With just a few simple steps, you can create these irresistibly moist and flavorful Pineapple Upside-Down Cupcakes. Bursting with tropical flavors from the pineapple and cherries, these treats are bound to become a family favorite. Whether enjoyed warm or at room temperature, these homemade delights are sure to bring a taste of paradise to any occasion. Dive in and enjoy the sweet simplicity of these delightful cupcakes!