- 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.