Preheat your oven to 350°F (175°C). Line a large baking sheet with parchment paper to prevent sticking and ensure even baking. Set aside.
In a large mixing bowl, cream together the softened butter and granulated sugar using a hand mixer or stand mixer on medium speed for about 2–3 minutes. The mixture should be pale and fluffy, indicating that air has been incorporated for a light cookie texture.
Add in the egg and vanilla extract. Continue mixing on medium speed until the egg is fully incorporated and the batter is smooth and creamy. Scrape down the sides of the bowl as needed.
In a separate bowl, whisk together the all-purpose flour, baking powder, and salt until evenly combined. This ensures the leavening is distributed throughout the dough.
Gradually add the dry mixture into the butter mixture, mixing on low speed and increasing as needed until a soft, pliable dough forms. Avoid overmixing, which can toughen the cookies.
Scoop out approximately 2 tablespoons of dough and roll into a ball. Flatten each ball into a round disk using your hands or the bottom of a glass. Place each round on the prepared baking sheet, spaced evenly apart.
Gently press a well-drained pineapple ring on top of each dough disk, centering it carefully. The pineapple should slightly press into the dough but still rest mostly on top.
Place one maraschino cherry in the center hole of each pineapple ring. Make sure the cherries are patted dry to prevent excess moisture from spreading during baking.
