Ingredients:

  • 1/2 cup (113g) Unsalted Butter (for topping)
  • 1 cup (200g) Light Brown Sugar, packed (for topping)
  • 1 (20 oz/567g) can Drained Pineapple Rings (in juice)
  • 8–10 Drained Maraschino Cherries
  • 1 3/4 cups (210g) All-Purpose Flour
  • 2 teaspoons Baking Powder
  • 1/2 teaspoon Salt
  • 1/2 cup (113g) Unsalted Butter, softened (for batter)
  • 1 cup (200g) Granulated Sugar
  • 2 Large Eggs, room temperature
  • 1 teaspoon Vanilla Extract
  • 1/2 cup (120ml) Milk (whole or 2%)
  • 2 tablespoons Reserved Pineapple Juice

Instructions:

  1. Preheat oven to 350°F (175°C). Reserve 2 tablespoons of pineapple juice from the can.
  2. In a small saucepan, melt the 1/2 cup butter over medium heat. Stir in the brown sugar until fully dissolved and bubbly (about 2 minutes). Pour this hot caramel mixture evenly over the bottom of a prepared 9-inch cake pan.
  3. Arrange the drained pineapple rings neatly over the caramel base. Place one cherry in the center of each ring, and fill any gaps with extra cherries. Set the pan aside.
  4. Whisk together flour, baking powder, and salt in a medium bowl.
  5. In a separate large bowl, cream the softened butter and granulated sugar until light and fluffy (about 3 minutes). Beat in the eggs one at a time, followed by the vanilla extract.
  6. Combine the milk and the 2 tablespoons of reserved pineapple juice. Alternate adding the dry ingredients and the wet ingredients to the butter mixture, beginning and ending with the dry (e.g., 1/3 dry, 1/2 wet, 1/3 dry, 1/2 wet, 1/3 dry). Mix only until just combined—do not overmix!
  7. Carefully spoon the batter evenly over the pineapple and caramel layer in the pan. Gently spread to cover without disturbing the fruit too much.
  8. Bake for 40–45 minutes, or until a wooden skewer inserted into the centre comes out clean.
  9. Remove from oven and let cool in the pan on a wire rack for exactly 10 minutes.
  10. Place a serving plate larger than the cake pan upside down over the top of the cake pan. Wearing oven mitts, firmly grip both the pan and the plate together, and confidently flip the entire assembly over in one swift motion. Gently lift the pan off the cake.