Preheat your oven to 350°F (175°C).
Melt 1/4 cup of unsalted butter and pour it into a 9-inch round cake pan, spreading it evenly over the bottom.
Sprinkle the brown sugar evenly over the melted butter in the cake pan.
Arrange the Pineapple and Cherries:
Arrange the pineapple slices in a single layer over the brown sugar, fitting them snugly into the pan.
Place a maraschino cherry in the center of each pineapple slice and in any gaps between the slices. Set aside.
Make the Cake Batter:
In a medium bowl, whisk together the all-purpose flour, baking powder, and salt. Set aside.
In a large bowl, cream together 1/2 cup of softened unsalted butter and 3/4 cup of granulated sugar until light and fluffy.
Beat in the eggs, one at a time, then stir in the vanilla extract.
Combine Wet and Dry Ingredients:
Gradually add the flour mixture to the butter mixture, alternating with additions of pineapple juice and milk.
Mix until just combined, being careful not to overmix.
Assemble the Cake:
Pour the batter evenly over the arranged pineapple slices and cherries in the cake pan.
Spread the batter gently with a spatula to ensure it covers the fruit evenly.
Bake the Cake:
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