Preheat the oven to 350°F (175°C) and line a muffin tin with cupcake liners.
Melt butter and brown sugar in a saucepan. Spoon a small amount of caramel into each cupcake liner.
Place one pineapple ring in each liner, topping with a maraschino cherry.
In a medium bowl, whisk the dry ingredients. In another bowl, cream butter and sugar, then add eggs, vanilla, and pineapple.
Add dry ingredients alternately with milk. Spoon batter over the pineapple.
Bake for 18-20 minutes, then cool for 5 minutes.
Invert onto a platter to reveal the caramelized pineapple topping.