Begin by draining the crushed pineapple thoroughly to avoid soggy cookies. Set it aside while you prepare the dough.
In a large bowl, use an electric mixer to cream together the softened unsalted butter, granulated sugar, and brown sugar until the mixture is light and fluffy, about 3-4 minutes on medium speed.
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 flour mixture to the wet ingredients, mixing just until combined. Avoid overmixing.
Gently fold the drained crushed pineapple into the cookie dough, distributing it evenly without breaking it down too much.
Line your baking sheet with parchment paper or a silicone baking mat. Using a spoon or cookie scoop, drop dollops of dough spaced about 2 inches apart.
Sprinkle a small pinch of brown sugar on top of each cookie dough ball. Then, press a maraschino cherry gently into the center of each cookie, pushing it slightly into the dough.
Bake at 350°F (175°C) for 12-15 minutes, or until the edges are golden and the cookies have set.
Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a cooling rack.