Preheat Oven: Preheat your oven to 350°F (175°C). Line a 12-cup muffin tin with non-stick spray or grease well.

Prepare the Topping: In each muffin cup, pour about 1 teaspoon of melted butter, then sprinkle 1 teaspoon of brown sugar over the butter. Place half of a pineapple ring in each cup, and then place a maraschino cherry in the center of each pineapple half.

Prepare the Sugar Cookie Dough: In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. Beat in the egg and vanilla extract until well combined.

Mix Dry Ingredients: In another bowl, whisk together the flour, baking powder, baking soda, and salt. Gradually add the dry ingredients to the wet mixture, mixing until just combined.

Assemble the Cookies: Roll the cookie dough into 1-inch balls and slightly flatten them. Place a flattened ball of dough on top of each pineapple slice in the muffin tin.

Bake: Bake in the preheated oven for 12-15 minutes, or until the edges of the cookies are lightly golden and the cookie dough is cooked through.

Cool and Invert: Allow the cookies to cool in the tin for about 5 minutes. Carefully run a knife around the edges of each cookie and invert the muffin tin onto a wire rack, letting the cookies release upside down.

Serve: Enjoy warm or at room temperature.