Begin by preheating your oven to 350°F (175°C). In a mixing bowl, cream together softened butter and sugar until the mixture is light and fluffy, about 2-3 minutes. Beat in the egg until fully incorporated, then gradually mix in the dry ingredients: flour, baking powder, and salt. Be careful not to overmix; the dough should remain soft and smooth.

In a skillet over medium heat, melt 2 tablespoons of butter and add an equal amount of brown sugar, stirring until combined. Place the pineapple rings into the skillet, allowing them to caramelize for about 2-3 minutes on each side, or until they are golden and fragrant. Once caramelized, remove from heat and set aside to cool slightly.

Line a baking sheet with parchment paper for easy cleanup. Place a caramelized pineapple ring in the center of each cookie space on the sheet. Top each ring with a cherry for a vibrant finish. Using a tablespoon, scoop a generous amount of cookie dough around each pineapple and cherry, creating a little nest of sweetness around the toppings.

Transfer the baking sheet into the preheated oven and bake the Pineapple Upside-Down Cookies for 12-15 minutes. Keep an eye on them and look for a golden-brown edge and a dome shape—this indicates they are perfectly baked. The aroma of the caramelized pineapple will fill your kitchen, reminiscent of a tropical paradise.

Once baked, allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack. Enjoy them warm for the best flavor, as the chewy cookies will be complemented by the juicy pineapple and sweet cherry. These Pineapple Upside-Down Cookies are sure to be a hit at any gathering or a delightful treat just for you!