Ingredients:

  • 1/2 cup unsalted butter, melted
  • 3/4 cup light brown sugar, packed
  • 1 can (20 oz) pineapple slices in juice
  • 10 maraschino cherries, patted dry
  • 1 1/2 cups cake flour
  • 1 cup granulated sugar
  • 1 1/2 tsp baking powder
  • 1/4 tsp salt
  • 1/2 cup unsalted butter, softened
  • 2 large eggs
  • 1 tsp vanilla extract
  • 2 tbsp reserved pineapple juice

Instructions:

  1. Preheat the oven to 350°F (180°C).
  2. Pour 1/2 cup melted unsalted butter into the bottom of a 9-inch cast iron skillet or round cake pan and stir in 3/4 cup packed light brown sugar until it forms a smooth, thick paste; spread the mixture evenly across the bottom.
  3. Place one pineapple ring from the 20 oz can in the center of the pan and surround it with six more rings, slightly overlapping; nestle one dried maraschino cherry into the center of each ring and place remaining cherries in the gaps.
  4. In a medium bowl, whisk together 1 1/2 cups cake flour, 1 1/2 tsp baking powder, and 1/4 tsp salt.
  5. In a separate large bowl, cream 1/2 cup softened unsalted butter and 1 cup granulated sugar until light and fluffy.
  6. Beat 2 large eggs into the butter mixture one at a time, then stir in 1 tsp vanilla extract and 2 tbsp reserved pineapple juice.
  7. Gradually fold the dry flour mixture into the wet ingredients until just combined, taking care not to overmix.
  8. Carefully spoon the batter over the arranged fruit, smoothing the top with a spatula to ensure no fruit is exposed.
  9. Bake for 35 to 40 minutes; test for doneness by inserting a toothpick into the outer edge of the cake; it should come out clean or with a few moist crumbs.
  10. Remove the pan from the oven and let it rest for 5 minutes.
  11. Run a knife around the edges, place a large plate over the pan, and firmly flip it over; lift the pan slowly to reveal the caramelized topping.