Drain the crushed pineapple thoroughly. In a small bowl, mix the brown sugar with the pineapple, coating the fruit well. Set aside.
In a large mixing bowl, beat the softened unsalted butter and granulated sugar together using an electric mixer on medium speed until light and fluffy, about 3 to 4 minutes.
Add the eggs one at a time, beating well after each addition. Stir in the vanilla extract.
In a separate bowl, whisk together the all-purpose flour, baking powder, baking soda, and salt.
Gradually add the dry ingredients to the butter mixture, mixing on low speed until just combined. Avoid over-mixing.
Line a baking sheet with parchment paper or a silicone baking mat. Drop about a tablespoon of cookie dough onto the sheet, spacing about 2 inches apart. Flatten each mound slightly.
Spoon a small amount of the pineapple and brown sugar mixture onto each cookie, pressing gently into the dough. Place a maraschino cherry on top of each cookie.
Preheat oven to 350°F (175°C). Bake cookies for 12-15 minutes or until edges turn golden brown and the pineapple topping caramelizes.
Allow cookies to cool on the baking sheet for 5 minutes before transferring to a cooling rack. Serve warm or at room temperature.