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Preheat your oven to 350°F (180°C) and line your baking trays with parchment paper.
Cream the softened unsalted butter and granulated sugar together until light and fluffy, about 2-3 minutes.
Add the large egg and vanilla extract, beating well until combined.
Whisk together the all-purpose flour, baking soda, and salt in a separate bowl, then gradually mix into the wet mixture until a soft dough forms.
Scoop 2 tablespoons of dough for each cookie and place on the prepared trays, leaving space between each.
Press a pineapple ring gently into each dough mound, flattening slightly.
Sprinkle additional sugar generously on top of the pineapple rings.
Bake for 11-13 minutes, or until edges are golden and centers are set.
Cool the cookies on the tray for a few minutes before transferring to a wire rack for complete cooling.