Preheat your oven to 350°F (175°C) and gather all the ingredients.

Melt 1/4 cup of butter in a 9-inch round cake pan. Sprinkle 1 cup of brown sugar evenly over the melted butter. Arrange the pineapple rings on top and place a cherry in each center.

In a mixing bowl, cream together 1 cup of granulated sugar and 1/2 cup of softened butter until light and fluffy. Add the eggs one at a time, beating well after each addition. Stir in 1 teaspoon of vanilla extract.

Alternate adding the dry ingredients (1 cup of flour, 2 teaspoons of baking powder, and 1/2 teaspoon of salt) with 1/2 cup of milk until well combined.

Pour the batter over the arranged pineapple and cherries in the cake pan. Bake for 30 minutes or until a toothpick inserted in the center comes out clean.

Allow the cake to cool for a few minutes before inverting it onto a serving plate. Serve warm or at room temperature.