Preheat your oven to 350°F and line a baking sheet with parchment paper.

In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy, about 2-3 minutes. Add the egg and vanilla extract, mixing until well combined.

In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add this dry mixture to the wet ingredients, stirring gently until just combined.

In a small bowl, mix the drained crushed pineapple with the packed brown sugar until evenly coated.

Scoop about 1 tablespoon of cookie dough, flatten it slightly, place a teaspoon of the pineapple mixture in the center, and fold the dough around it to form a ball. Place on the baking sheet and press a maraschino cherry into the center of each ball.

Bake in the preheated oven for 10-12 minutes, or until the edges are lightly golden. Allow to cool on the baking sheet for about 5 minutes before transferring to a wire rack.