Step 1: Preheat the Oven

1. Preheat Oven: Preheat your oven to 350°F (175°C). Line baking sheets with parchment paper.

Step 2: Prepare the Cookie Dough

1. Cream Butter and Sugar: In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy.
2. Add Egg and Vanilla: Beat in the egg and vanilla extract until well combined.
3. Mix Dry Ingredients: In another bowl, whisk together the flour, baking soda, and salt.
4. Combine Mixtures: Gradually add the dry ingredients to the wet ingredients, mixing until just combined.

Step 3: Prepare the Topping

1. Prepare Pineapple: Cut the drained pineapple slices into smaller pieces if desired.
2. Mix Brown Sugar: In a small bowl, mix the brown sugar with a little bit of the pineapple juice to form a paste.

Step 4: Assemble the Cookies

1. Scoop Dough: Using a cookie scoop or tablespoon, drop cookie dough onto the prepared baking sheets, spacing them about 2 inches apart.
2. Add Topping: Press a piece of pineapple into the center of each cookie, then drizzle a small amount of the brown sugar mixture over the pineapple. Top each cookie with a maraschino cherry.

Step 5: Bake

1. Bake Cookies: Bake in the preheated oven for 12–15 minutes, or until the edges are lightly golden.
2. Cool: Allow the cookies to cool on the baking sheets for a few minutes before transferring them to a wire rack to cool completely.

Step 6: Serve

1. Enjoy: Serve the cookies warm or at room temperature.