Prepare the Topping

1. Preheat Oven: Set your oven to 350°F (175°C). Grease a 9-inch round cake pan with butter or nonstick spray.
2. Create the Caramelized Base: Pour the melted butter into the bottom of the pan and sprinkle the brown sugar evenly over it.
3. Arrange the Pineapple Rings: Place the pineapple slices in a single layer over the sugar, spacing them evenly.
4. Add the Cherries: Place a maraschino cherry in the center of each pineapple ring for a pop of color.

Make the Cake Batter

1. Combine Dry Ingredients: In a medium bowl, whisk together the flour, baking powder, and salt.
2. Cream Butter and Sugar: In a separate large bowl, beat the softened butter and sugar together until light and fluffy.
3. Add Eggs: Beat in the eggs, one at a time, mixing well after each addition.
4. Incorporate Liquids: Stir in the vanilla extract, pineapple juice, and milk.
5. Mix the Batter: Gradually add the dry ingredients to the wet ingredients, mixing until just combined.

Assemble and Bake

1. Pour the Batter: Carefully pour the cake batter over the pineapple topping, spreading it evenly.
2. Bake: Place the cake in the oven and bake for 35-40 minutes, or until a toothpick inserted into the center comes out clean.
3. Cool Slightly: Remove the cake from the oven and let it cool in the pan for about 10 minutes.
4. Flip the Cake: Run a knife around the edges of the pan to loosen the cake. Place a serving plate over the pan, then quickly flip it upside down. Let it sit for a minute before gently lifting the pan off.