Ingredients:

  • ½ cup (1 stick) (113g) unsalted butter, cut into pieces
  • 1 cup (200g) packed light brown sugar
  • 1 (20 ounce) can pineapple slices in juice, drained (reserve 1/4 cup of the juice)
  • Maraschino cherries, halved
  • 1 ½ cups (192g) all-purpose flour
  • 1 ½ teaspoons baking powder
  • ¼ teaspoon salt
  • ½ cup (113g) unsalted butter, softened
  • ¾ cup (150g) granulated sugar
  • 2 large eggs
  • ½ teaspoon vanilla extract
  • ½ cup (120ml) milk
  • ¼ cup Reserved pineapple juice

Instructions:

  1. Preheat oven to 350°F (175°C). Grease and flour the cake pan.
  2. Melt butter in the cake pan on the stovetop over medium heat. Stir in brown sugar until dissolved and evenly combined. Cook, stirring constantly, for 1-2 minutes until smooth and bubbly. Remove from heat.
  3. Arrange pineapple slices in a decorative pattern over the caramel. Place a cherry half in the center of each pineapple ring and in any gaps.
  4. In a medium bowl, whisk together flour, baking powder, and salt.
  5. In a separate large bowl, cream together softened butter and granulated sugar until light and fluffy using an electric mixer.
  6. Beat in the eggs one at a time, then stir in vanilla extract and reserved pineapple juice.
  7. Gradually add the dry ingredients to the wet ingredients, alternating with the milk, beginning and ending with the dry ingredients. Mix until just combined. Do not overmix.
  8. Gently pour the cake batter over the pineapple and cherry layer, spreading evenly.
  9. Bake for 45-55 minutes, or until a toothpick inserted into the center comes out clean.
  10. Let the cake cool in the pan for 10 minutes. Run a knife around the edge of the pan to loosen the cake. Place a serving plate over the pan and carefully invert the cake onto the plate.
  11. Let the pineapple upside down cake cool slightly before serving.