Preheat your oven to 350°F (175°C).

In a small saucepan, melt the butter over low heat. Add the brown sugar and stir until combined and smooth.

Grease your cookie sheet or line it with parchment paper.

Pour the melted mixture onto the bottom of the prepared pan. Place the pineapple rings on top and add a maraschino cherry in the center of each ring.

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

Beat in the eggs one at a time, followed by the vanilla extract.

In a separate bowl, combine the flour, baking soda, and salt. Gradually add this to the wet mixture, mixing until fully combined.

Using a cookie scoop or your hands, drop spoonfuls of dough onto the pineapple rings in the pan, ensuring they cover the pineapple but leave space for spreading.

Bake in the preheated oven for 12-15 minutes or until the edges are golden brown.

Let the cookies cool in the pan for about 5 minutes before carefully inverting the pan onto a cooling rack or serving platter.