In a medium skillet over medium heat, melt 2 tablespoons of unsalted butter with 1/3 cup of brown sugar until it bubbles, about 2-3 minutes. Stir in 1 cup of chopped pineapple and cook for an additional 2-3 minutes.

In a large mixing bowl, cream together 1/2 cup of unsalted butter and 1/2 cup of granulated sugar until light and fluffy, about 3-4 minutes. Add 1 room temperature egg and a splash of vanilla extract.

Gradually blend in 1 cup of all-purpose flour and 1/2 teaspoon of baking soda until just combined.

Preheat your oven to 350°F (175°C) and spread the caramelized pineapple mixture evenly across the bottom of a prepared baking sheet.

Dollop spoonfuls of the cookie dough on top of the pineapple.

Place the baking sheet in the preheated oven and bake for 12-15 minutes, or until the edges are golden brown.

Once baked, allow the cookies to cool in the pan for about 5 minutes before transferring them to a wire rack to cool completely.