Ingredients:

  • 1/2 cup (113g) unsalted butter, softened (for topping)
  • 3/4 cup (150g) packed dark brown sugar
  • 1 can (20 oz) pineapple slices in juice, drained (reserve 1/4 cup juice)
  • 9 Maraschino cherries, patted dry
  • 1 1/2 cups (190g) all-purpose flour
  • 1 1/2 tsp baking powder
  • 1/4 tsp fine sea salt
  • 1 cup (200g) granulated white sugar
  • 1/2 cup (113g) unsalted butter, softened (for batter)
  • 2 large eggs, room temperature
  • 1 tsp pure vanilla extract
  • 1/4 tsp almond extract
  • 1/2 cup (120ml) whole milk
  • 1/4 cup reserved pineapple juice

Instructions:

  1. Preheat the oven. Set your oven to 175°C (350°F). Make sure the rack is in the center position for even heat distribution.
  2. Prepare the Foundation. Spread the 113g of softened butter for the topping evenly across the bottom and about 1 cm up the sides of your 9 inch pan.
  3. Create the Caramel Layer. Sprinkle the 150g dark brown sugar evenly over the butter. Use your fingers to press it down slightly into the butter until it looks like wet sand.
  4. Arrange the Fruit. Place the drained pineapple slices on top of the sugar. I like to put one in the center and others around it. Pop a dried cherry into the center of each ring. Press them down firmly so they stay put when you pour the batter.
  5. Whisk Dry Ingredients. In a medium bowl, combine the 190g flour, baking powder, and salt. Use a whisk to ensure there are no lumps — we want this cake to be silky.
  6. Cream Butter and Sugar. In a large bowl, beat the remaining 113g softened butter and 200g granulated sugar. Do this for at least 3 minutes until the mixture looks pale and fluffy.
  7. Incorporate Eggs. Beat in the eggs one at a time, then stir in the vanilla and almond extracts.
  8. Combine Wet and Dry. Alternately add the flour mixture, milk, and the reserved 1/4 cup of pineapple juice to the creamed mixture, beginning and ending with the flour mixture. Mix until just combined.
  9. Assemble and Bake. Carefully spread the batter over the pineapple slices in the pan. Bake for 45 minutes, or until a toothpick inserted into the center of the cake comes out clean.
  10. Cool and Invert. Cool the cake in the pan on a wire rack for 10 minutes. Run a knife around the edge, place a serving plate over the pan, and confidently invert the cake. Let the pan sit for a minute before lifting to allow the caramel to drizzle down.