Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper.

In a small saucepan, melt the brown sugar over medium heat until bubbly. Add the pineapple rings and cook for 2-3 minutes until caramelized. Remove from heat.

Place the caramelized pineapple rings on the prepared baking sheet and place a maraschino cherry in the center of each ring.

In a mixing bowl, cream together the softened butter and granulated sugar until light and fluffy.

Add the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.

In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture, mixing until just combined.

Drop spoonfuls of the cookie dough over the pineapple rings on the baking sheet, covering them evenly.

Bake in the preheated oven for 15-20 minutes or until the cookies are golden brown.

Allow the cookies to cool for a few minutes before inverting onto a serving plate.