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

In a large mixing bowl, beat ½ cup of softened unsalted butter with 1 cup of granulated sugar for 2-3 minutes until light and fluffy.

Add 1 large egg and 1 teaspoon of vanilla extract to the butter-sugar mixture and mix on low speed until fully incorporated.

In a separate bowl, whisk together 1 ½ cups of all-purpose flour, 1 teaspoon of baking soda, and ½ teaspoon of salt. Gradually add to the wet ingredients and mix until a soft dough forms.

Using a cookie scoop, drop mounds of dough onto the prepared baking trays, spacing them about 2 inches apart.

Press a well-drained canned pineapple ring into each cookie mound and sprinkle with additional sugar if desired.

Bake for 11-13 minutes until the edges are golden brown and the center remains soft.

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