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

In a large mixing bowl, combine softened unsalted butter and granulated sugar. Beat the mixture on medium speed for 2-3 minutes until light and fluffy.

Add a large egg and optional vanilla extract to the butter-sugar mixture, then mix on low speed until well combined.

In a separate bowl, whisk together all-purpose flour, baking soda, and salt. Gradually add this dry mixture into the wet batter, mixing on low speed until the dough forms.

Using a cookie scoop or tablespoon, portion about 2 tablespoons of dough onto your prepared trays, spacing them about 2 inches apart.

Press a drained pineapple ring into the center of each dough mound and sprinkle with additional sugar.

Bake for 11 to 13 minutes, until the edges turn golden and centers appear set.

Allow the cookies to cool for a few minutes before transferring to a wire rack.