Preheat the oven to 350?F (175?C).

In a small saucepan, combine the brown sugar and pineapple rings over medium heat until the sugar is dissolved and the pineapple is slightly caramelized.

Remove from heat and set aside.

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

Add the egg and vanilla extract, mixing until well combined.

In a separate bowl, whisk together the flour, baking soda, and salt.

Gradually add the dry ingredients to the wet mixture, stirring until just combined.

Spoon the caramelized pineapple mixture onto a baking sheet lined with parchment paper, forming small circles.

Place a maraschino cherry in the center of each pineapple ring.

Top each with a spoonful of cookie dough, covering the pineapple and cherry.

Bake in the preheated oven for 10-12 minutes or until golden brown.

Allow to cool slightly before serving.