Preheat your oven to 350°F (175°C) and line a 12-cup muffin tin with paper liners. Alternatively, grease the muffin tin directly.

1. In a small bowl, mix together the melted butter and brown sugar. Spoon this mixture evenly into the bottom of each muffin cup.
2. Place one pineapple ring in each muffin cup over the sugar-butter mixture. If the pineapple rings are too large, cut them in half to fit. Place a maraschino cherry in the center of each pineapple ring.
3. In a medium bowl, whisk together the flour, granulated sugar, salt, and baking powder.
4. In a separate bowl, beat together the softened butter, milk, egg, and vanilla extract until smooth and well combined.
5. Gradually add the dry ingredients to the wet ingredients, mixing until just combined to form the cupcake batter.
6. Carefully spoon the batter into each muffin cup over the pineapple and cherry layer, filling each cup about 2/3 full.
7. Bake for 20-22 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
8. Remove from the oven and allow the cupcakes to cool in the tin for about 5 minutes. Then, run a knife around the edges of each cupcake to loosen it and invert them onto a serving platter.
9. Serve the cupcakes warm or at room temperature, garnished with additional pineapple if desired.