Step 1: Prepare the Pineapple Topping
• Melt Butter: In a small saucepan over medium heat, melt the 2 tablespoons of butter. Add the diced pineapple and brown sugar, stirring to combine.
• Cook: Cook for 3-5 minutes until the pineapple is softened and the mixture is bubbly. Remove from heat and let cool slightly.

Step 2: Prepare the Cookie Dough
• Preheat Oven: Preheat your oven to 350°F (175°C). Line baking sheets with parchment paper.
• Cream Butter and Sugars: In a large mixing bowl, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy.
• Add Eggs and Vanilla: Beat in the eggs one at a time, followed by the vanilla extract, mixing until well combined.
• Mix Dry Ingredients: In another bowl, whisk together the flour, baking soda, baking powder, and salt.
• Combine Mixtures: Gradually add the dry ingredients to the wet ingredients, mixing until just combined.

Step 3: Assemble and Bake the Cookies
• Scoop Dough: Use a cookie scoop or tablespoon to drop dough onto the prepared baking sheets, spacing them about 2 inches apart.
• Add Pineapple Topping: Make a small indentation in the center of each cookie dough mound and spoon a small amount of the pineapple mixture into the indentation. Top each with a maraschino cherry.
• Bake: Bake in the preheated oven for 10-12 minutes, or until the edges are lightly golden and the centers are set. The cookies may look slightly underbaked but will firm up as they cool.

Step 4: Cool and Serve
• Cool: Remove the cookies from the oven and let them cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely.
• Enjoy: Serve warm or at room temperature, and enjoy the delightful flavors of pineapple upside-down cake in cookie form!