1. Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
2. In a large mixing bowl, cream together the butter and granulated sugar until light and fluffy, about 3-4 minutes.
3. Add in the eggs, one at a time, beating well after each addition. Stir in the vanilla extract.
4. In another bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture, mixing until just combined.
5. Gently fold in the well-drained crushed pineapple, ensuring even distribution throughout the dough.
6. In a small saucepan, melt the brown sugar over medium heat until it begins to caramelize, then remove from heat.
7. Spoon small dollops of the caramelized brown sugar onto the prepared baking sheet, leaving enough space for each cookie to spread.
8. Drop rounded tablespoons of the cookie dough over the caramelized sugar, pressing lightly to flatten.
9. If desired, place a maraschino cherry in the center of each cookie for a pop of color and flavor.
10. Bake for 10-12 minutes, or until the edges are golden brown. Allow cookies to cool on the baking sheet for a few minutes before transferring to a wire rack.

One tip I learned from my grandmother is to always keep an eye on the caramelizing sugar—it’s a fine line between perfectly caramelized and burnt! Patience and attentiveness are the keys to achieving that perfect balance.