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Preheat the oven: Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper or silicone baking mats.
Prepare the cookie dough: In a medium bowl, whisk together the flour, baking soda, and salt. In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy. Add the egg, vanilla extract, and milk, and beat until combined. Gradually add the dry ingredients and mix until just combined.
Shape the cookie dough: Scoop tablespoon-sized portions of dough and roll them into balls. Place the dough balls onto the prepared baking sheets, spacing them about 2 inches apart.
Prepare the topping: Gently press the dough balls down slightly with the back of a spoon to flatten them. Take half of a pineapple ring and place it in the center of each cookie dough ball. Sprinkle each pineapple ring with a small amount of brown sugar. Place a maraschino cherry on top of each pineapple ring.
Bake the cookies: Bake the cookies for 12-15 minutes or until the edges are golden brown. Remove the cookies from the oven and let them cool on the baking sheet for a few minutes before transferring them to a wire rack to cool completely.
Serve and enjoy: These cookies are best served fresh, but you can store them in an airtight container for up to 3 days.