Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper or silicone baking mats to ensure the cookies don’t stick and bake evenly.

In a small bowl, mix the drained crushed pineapple, brown sugar, and melted butter until well combined. Once mixed, drop small spoonfuls (about 1 teaspoon each) of the pineapple mixture onto the prepared baking sheet, spacing them about 2 inches apart. The pineapple topping will spread and caramelize as it bakes, giving the cookies a delightful tropical flavor.

In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy, which should take about 2–3 minutes. Beat in the egg and vanilla extract until smooth and well incorporated.

In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Add 2–3 tablespoons of the reserved pineapple juice to the dough, 1 tablespoon at a time, until the dough reaches a soft, scoopable consistency. The pineapple juice adds a subtle fruitiness to the dough, enhancing the overall tropical theme of the cookies.

Scoop about 1 tablespoon of cookie dough and roll it into a ball. Place the dough ball directly on top of each pineapple topping dollop. Gently press down on the dough to slightly flatten it, helping it adhere to the pineapple layer. The dough should slightly cover the pineapple mixture, but leave the edges exposed to allow for even caramelization.

Bake for 10–12 minutes, or until the edges of the cookies are lightly golden and the cookies are set. Remove the baking sheet from the oven and let the cookies cool for about 5 minutes on the baking sheet to firm up before flipping them.

Carefully flip each cookie over using a spatula to reveal the caramelized pineapple topping underneath. Let the cookies cool completely before serving to allow the pineapple to fully set and give the cookies a chance to firm up.