Preheat your oven to 350°F (175°C).
In a large bowl, cream together the softened butter, brown sugar, and granulated sugar until light and fluffy.
Add the eggs one at a time, mixing well after each addition, then stir in the vanilla extract.
In a separate bowl, whisk together the flour, baking soda, and salt.
Gradually add the dry ingredients to the creamed mixture, mixing just until combined.
Gently fold in the crushed pineapple until evenly distributed throughout the dough.
Drop rounded tablespoons of dough onto a parchment-lined baking sheet, leaving space between each cookie.
Bake in the preheated oven for about 10-12 minutes or until the edges are lightly golden.
Remove from the oven and let cool on the baking sheet for a few minutes before transferring them to a wire rack.
Top each cookie with a maraschino cherry while they are still warm.