Preheat the oven to 350°F (175°C). In a mixing bowl, cream together the softened butter and brown sugar until light and fluffy.

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

In another bowl, whisk together the flour, baking soda, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until just combined.

In a small saucepan, melt the butter and brown sugar over medium heat until bubbly. Stir in the pineapple rings and cherries, allowing them to caramelize for about 2-3 minutes.

Scoop the cookie dough onto a baking sheet lined with parchment paper, making sure to leave space between each cookie.

Place a caramelized pineapple ring and a cherry half on top of each cookie dough scoop.

Bake in the preheated oven for 10-12 minutes or until the edges are golden brown. Let cool on the baking sheet for a few minutes before transferring to a wire rack.