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

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

Add the room-temperature egg and vanilla extract, mixing gently to combine.

In a separate bowl, whisk together the all-purpose flour, baking soda, and salt. Gradually incorporate the dry mixture into the wet ingredients until a soft dough forms.

Using a cookie scoop, portion out the dough into 1½ tablespoon balls on the prepared baking sheets, flatten slightly, and top each with a pineapple ring, pressing gently.

Sprinkle additional sugar on top of each pineapple ring if desired.

Bake for 12-14 minutes, until golden around the edges and soft in the center.

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