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

In a large mixing bowl, cream together the softened butter and granulated sugar for about 3-4 minutes until light and fluffy.

Crack the egg into the creamed mixture and add the vanilla extract, beating until fully incorporated.

In a separate bowl, whisk together the flour, baking soda, and salt, and then gradually mix into the wet ingredients until just combined.

Scoop and roll the cookie dough into balls, placing them on the prepared baking sheets, and flatten slightly.

Press a pineapple ring on top of each flattened dough ball, securing gently.

Sprinkle additional sugar over each pineapple ring.

Bake in the preheated oven for 12 to 14 minutes until the edges are golden brown and the centers are soft.

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

Enjoy your Pineapple Upside Sugar Cookies once they have cooled!