Pineapple Upside Down Cake
A tender vanilla cake topped with caramelized pineapple rings and maraschino cherries. This classic American dessert features a buttery brown sugar glaze that creates a delicious caramel flavor when baked and inverted.
Ingredients
- ¼ cup unsalted butter melted
- ⅔ cup packed brown sugar
- 1 can 20 oz pineapple rings in juice, drained (reserve ¼ cup juice)
- Maraschino cherries about 10-12
- 1½ cups all-purpose flour
- 1 cup granulated sugar
- 2 teaspoons baking powder
- ½ teaspoon salt
- ¼ cup vegetable oil
- 1 cup milk
- 1 teaspoon vanilla extract
- 2 large eggs
Instructions
- Preheat your oven to 350°F (175°C) and position the rack in the center of the oven for even baking.
- Prepare the caramel base by pouring the melted butter into your 9-inch round cake pan, making sure it coats the entire bottom.
- Sprinkle the brown sugar evenly over the melted butter, creating a thin, consistent layer that will caramelize during baking.
- Arrange pineapple rings in a single layer on top of the brown sugar mixture—you should fit about 7 rings, with one in the center and six around it.
- Place a maraschino cherry in the center of each pineapple ring and in any gaps between rings for that classic look.
- In a large mixing bowl, whisk together the flour, granulated sugar, baking powder, and salt until well combined.
- Add the vegetable oil, milk, vanilla, and eggs to the dry ingredients and beat with an electric mixer on medium speed for 2 minutes until smooth.
- Stir in the reserved ¼ cup pineapple juice to infuse the batter with subtle pineapple flavor.
- Carefully pour the batter over the pineapple arrangement, making sure not to disturb the pattern.
- Bake for 30-35 minutes or until a toothpick inserted into the center comes out clean and the top is golden brown.
- Allow the cake to cool for exactly 5 minutes in the pan—this timing is crucial for successful release.
- Run a knife around the edge of the pan to loosen the cake, then place your serving plate upside down on top of the pan.
- Quickly but confidently flip the cake over onto the plate and wait 30 seconds before lifting the pan off to reveal your masterpiece.
- Let the cake cool for at least 15 minutes before serving to allow the caramel topping to set slightly.
Notes
- For the best caramelization, use dark brown sugar rather than light brown sugar.
- Fresh pineapple can be substituted, but canned works perfectly and is more consistent.
- This cake is best served slightly warm, but not hot, to maintain its structure.
- For extra flavor, add ½ teaspoon of cinnamon or ¼ teaspoon of nutmeg to the batter.
- The cake can be made up to a day ahead, but store at room temperature rather than refrigerating to prevent drying out.
- If you don’t have a round pan, a 9×9 inch square pan works too—just arrange the pineapple in a grid pattern.