Prepare the Oven and Pan:
Preheat your oven to 350°F (175°C).
Line two baking sheets with parchment paper.
Make the Cookie Dough:
Cream Butter and Sugar: In a large bowl, cream together the softened butter and granulated sugar until light and fluffy.
Add Wet Ingredients: Beat in the egg and vanilla extract until well combined.
Combine Dry Ingredients: In a separate bowl, whisk together the flour, baking powder, baking soda, and salt.
Mix Wet and Dry: Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Do not overmix.
Prepare the Topping and Assemble Cookies:
Melt Butter and Sugar: In a small saucepan over medium heat, melt the butter and brown sugar until bubbly and well combined.
Assemble: Place a spoonful of the butter-sugar mixture onto each prepared baking sheet. Top with a pineapple slice and a maraschino cherry.
Add Cookie Dough: Scoop a spoonful of cookie dough onto each pineapple slice and spread it out slightly.
Bake the Cookies:
Bake: Bake for 12-15 minutes, or until the edges are golden brown.
Cool: Let cool on the baking sheet for a few minutes before transferring to a wire rack to cool completely.
Prep Time: 20 minutes | Cook Time: 12-15 minutes | Total Time: 35-40 minutes
Kcal: Varies | Servings: About 24 cookies