1. Begin by preheating your oven to 350°F (175°C) and lining two baking sheets with parchment paper.
2. In a mixing bowl, cream the softened butter and granulated sugar together until the mixture becomes light and fluffy, approximately 3-4 minutes.
3. Incorporate the egg and vanilla extract, mixing until everything is well blended.
4. In a separate bowl, combine the all-purpose flour, baking powder, baking soda, and salt, whisking to mix thoroughly.
5. Gradually add the dry mixture into the creamed butter mixture, stirring gently until just combined without overmixing.
6. In a small saucepan, melt ¼ cup of unsalted butter along with the brown sugar over medium heat, stirring continuously until bubbly and smooth.
7. Spoon about a tablespoon of the butter-sugar mixture into the center of each cookie spot on the prepared baking sheets, then place a pineapple slice on top of each.
8. Position a maraschino cherry in the center of each pineapple slice for that classic look.
9. Scoop about 1 tablespoon of cookie dough and gently spread it over each pineapple slice, ensuring to cover it slightly while keeping some of the fruit visible.
10. Bake in the preheated oven for 12-15 minutes, or until the cookie edges turn a light golden brown. Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack for complete cooling.
11. Enjoy your delicious tropical-inspired cookies warm or at room temperature!
Prep Time: 15 minutes
Cook Time: 15 minutes
Total Time: 30 minutes
Yield: 24 cookies
