Preheat oven to 350 degrees Fahrenheit (175 degrees Celsius).

Melt 0.25 cup butter in a 9-inch round cake pan and sprinkle brown sugar evenly over the base.

Arrange pineapple slices on top of the sugar and place a maraschino cherry in the center of each ring.

In a medium bowl, whisk together flour, baking powder, and salt.

In a separate large bowl, cream 0.5 cup softened butter and granulated sugar until light and fluffy.

Beat in the egg and vanilla extract until well combined.

Gradually add the flour mixture to the creamed mixture, alternating with milk, beginning and ending with the dry ingredients.

Spread the batter evenly over the pineapple slices in the cake pan.

Bake for 40 to 45 minutes, or until a toothpick inserted into the center of the cake comes out clean.

Cool the cake in the pan for 10 minutes, then run a knife around the edges and invert onto a serving plate.