Preheat the oven to 350°F (175°C) and prepare a muffin tin with cupcake liners.
In a saucepan, melt the butter with brown sugar over medium heat until bubbly; pour evenly into muffin cups. Place a pineapple ring in each and top with a cherry.
In a mixing bowl, cream together granulated sugar and softened butter until fluffy. Add eggs one at a time, mixing well after each addition.
In another bowl, combine flour, baking powder, and salt. Gradually add this dry mixture alternately with milk to the wet mixture until well combined.
Spoon batter over pineapple rings in muffin cups, filling each about three-quarters full.
Bake for 20-25 minutes until golden brown. Allow to cool in the pan for 5 minutes before transferring to wire racks.