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Prepare the Topping:
Preheat your oven to 350°F (175°C).
In a 9-inch round cake pan, evenly coat the bottom with 1/4 cup melted unsalted butter.
Sprinkle 1/2 cup packed brown sugar over the melted butter.
Arrange the drained pineapple slices in a single layer over the sugar, pressing them snugly.
Place a maraschino cherry in the center of each pineapple slice and in any gaps.
Make the Cake Batter:
In a medium bowl, whisk together 1.5 cups flour, 1.5 tablespoons baking powder, and 1/4 teaspoon salt. Set aside.
In a large bowl, beat together 3/4 cup granulated sugar and 1/2 cup melted unsalted butter until light and fluffy.
Add the eggs one at a time, beating well after each addition, then mix in 1 teaspoon vanilla extract.
Gradually combine the dry ingredients with the wet ingredients, alternating with 1/4 cup milk and the reserved 1/2 cup pineapple juice. Mix just until combined; avoid overmixing.
Assemble and Bake:
Pour the batter evenly over the arranged pineapple and cherries in the pan, using a spatula to smooth it out.
Bake for 40-45 minutes, or until a toothpick inserted in the center comes out clean.
Allow the cake to cool in the pan for 10-15 minutes on a wire rack.
Flip and Serve:
Carefully run a knife around the edges of the cake to loosen it.
Place an upside-down serving plate over the cake pan and invert it gently to transfer the cake.
Lift off the cake pan to reveal the beautiful topping.
Enjoy:
Serve the Pineapple Upside-Down Cake warm or chilled. Feel free to add extra whipped cream or maraschino cherries for garnish before serving. Enjoy your delightful creation!
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