Preheat your oven to 350°F (180°C) and line your baking trays with parchment paper.

Combine softened unsalted butter with granulated sugar in a large mixing bowl and cream together for 2–3 minutes until light and fluffy.

Add in the large egg and optional vanilla extract to the creamed mixture and beat until combined.

Whisk together all-purpose flour, baking soda, and salt in a separate bowl, then gradually add to the wet ingredients.

Using a cookie scoop or tablespoon, portion out 2 tablespoons of dough for each cookie on the prepared trays.

Press a well-drained pineapple ring into each cookie dough mound, and sprinkle with additional sugar.

Bake for 11–13 minutes until edges are golden brown and centers are set.

Allow cookies to cool on the tray for 5 minutes before transferring to a wire rack.