Preheat the oven to 350°F. Line a baking sheet with parchment paper and lightly spray with nonstick cooking spray. This helps the cookies release easily and keeps the pineapple topping from sticking during baking.

In a small bowl, stir brown sugar with melted butter until combined. Spoon small amounts onto the baking sheet. Spread gently into little circles. Place chopped pineapple and cherry halves over each brown sugar mixture.

In a large mixing bowl, beat softened butter and granulated sugar until light and fluffy. Add the egg and vanilla extract. Mix again until smooth and creamy with no streaks remaining in the batter.

In another bowl, whisk together flour, baking powder, and salt. Slowly add the dry mixture into the wet ingredients. Stir gently until a soft cookie dough forms. Avoid overmixing to keep the cookies tender.

Use a cookie scoop to place dough over each pineapple topping on the baking sheet. Gently flatten the dough slightly with your fingers. Make sure the pineapple mixture stays centered underneath each cookie.

Place the baking sheet into the preheated oven. Bake for 12 to 14 minutes until the edges turn lightly golden. The cookies should look soft in the center but set around the sides.

Allow the cookies to cool for five minutes on the baking sheet. Carefully flip each cookie upside down while still warm. Move them onto a cooling rack and let them cool completely before serving.