Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper.

In a large mixing bowl, cream the softened unsalted butter and granulated sugar until light and fluffy, about 3-5 minutes.

Add in one large egg and the vanilla extract, beating until fully incorporated.

Whisk together the all-purpose flour, baking soda, and salt in a separate bowl. Gradually add to the wet mixture, stirring until a soft dough forms.

Scoop about 1½ tablespoons of dough, roll into a ball, and flatten slightly. Place on lined sheets 2 inches apart.

Press a pineapple ring into the center of each cookie disk and sprinkle with additional sugar before baking.

Bake for 12-14 minutes until edges are golden brown and pineapple is caramelized. Keep an eye on them!

Let the cookies cool on the sheets for 5 minutes before transferring to a wire rack.