Description

This classic Pineapple Upside Down Cake features caramelized pineapple slices and maraschino cherries atop a moist, buttery cake. The brown sugar and butter base create a rich, sticky topping that soaks into the cake when inverted, making every slice bursting with tropical sweetness and a hint of vanilla. Perfect for a warm dessert served with whipped cream or ice cream.

Ingredients

Scale

For the Topping

1/4 cup butter
2/3 cup packed brown sugar
9 pineapple slices from a 20-oz can, drained (reserve juice)
9 maraschino cherries

For the Cake Batter

1 1/3 cups all-purpose flour
1 cup granulated sugar
1/3 cup butter, softened
1 1/2 teaspoons baking powder
1/2 teaspoon salt
3/4 cup milk
1/4 cup reserved pineapple juice
1 large egg
1 teaspoon vanilla extract

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Instructions

Prepare the Topping: Heat your oven to 350°F (175°C). Melt 1/4 cup of butter in the microwave and pour it into a 9-inch square baking pan. Evenly sprinkle 2/3 cup packed brown sugar over the melted butter. Arrange the drained pineapple slices on top of the brown sugar, and place a maraschino cherry in the center of each pineapple slice to create the signature look.
Make the Cake Batter: In a medium bowl, combine 1 1/3 cups flour, 1 cup granulated sugar, 1/3 cup softened butter, 1 1/2 teaspoons baking powder, and 1/2 teaspoon salt. Using an electric mixer, beat the mixture on low speed for 40 seconds to blend, then increase to high speed and beat for 3 minutes until the batter is smooth and well combined. Add 3/4 cup milk, 1/4 cup reserved pineapple juice, 1 large egg, and 1 teaspoon vanilla extract, mixing well after each addition.
Assemble and Bake: Pour the prepared cake batter evenly over the arranged pineapple slices and cherries in the baking pan. Place the pan in the preheated oven and bake for 45 to 50 minutes, or until a toothpick inserted into the center of the cake comes out clean.
Invert and Serve: Once baked, immediately cover the pan with a serving plate or platter, then carefully invert the pan to release the cake so that the pineapple side is facing up. Let the cake sit for a few minutes to allow the topping to drizzle over the cake. Slice and serve warm. It’s delightful when topped with whipped cream or ice cream. Store any leftovers covered, either at room temperature or in the refrigerator.

Notes

Use fresh pineapple slices if preferred, but canned pineapple works well and adds sweetness.
Reserve the pineapple juice from the can to add moisture and flavor to the cake batter.
Ensure the butter and brown sugar mixture is evenly spread to create a consistent caramelized topping.
You can add a pinch of cinnamon or nutmeg to the batter for extra warmth and depth of flavor.
For best texture, serve the cake warm; leftovers reheat well in a microwave or oven.