Preheat oven to 350°F (180°C) and line two baking sheets with parchment paper to prevent sticking.

In a large mixing bowl, cream together softened butter and granulated sugar for 2-3 minutes until light and fluffy.

Add egg and vanilla extract to the creamed mixture. Beat until completely smooth without any streaks.

In a separate bowl, whisk together flour, baking soda, and salt until evenly distributed.

Gradually mix the dry ingredients into the wet mixture, stirring just until a soft dough forms. Avoid overmixing.

Scoop about 2 tablespoons of dough for each cookie and place on prepared baking sheets, leaving 2 inches of space between each mound.

Press one pineapple ring gently but firmly into the center of each dough mound, flattening slightly. Trim or halve rings if needed.

Generously sprinkle additional sugar on top of each pineapple ring to enhance caramelization during baking.

Bake for 11-13 minutes or until edges are golden and centers appear set but still soft.

Let cookies cool on baking sheet for 5 minutes to firm up, then carefully transfer to a wire rack using a thin spatula. Cool completely before serving or storing.