Go Back
Here is what you need for the old fashioned pineapple upside-down cake: - 1 can (20 oz) sliced pineapple in juice, drained - 1/4 cup unsalted butter (½ stick) - 1/2 cup packed brown sugar - 10 maraschino cherries (optional) - 1 1/2 cups all-purpose flour - 1 cup granulated sugar - 1/2 cup unsalted butter, softened - 2 large eggs - 1 teaspoon vanilla extract - 1/2 cup whole milk - 1 1/2 teaspoons baking powder - 1/4 teaspoon salt

Old Fashioned Pineapple Upside-Down Cake

Craving a sweet treat that brings back memories? Discover the delightful Old Fashioned Pineapple Upside-Down Cake! This classic dessert features caramelized pineapple and a moist, fluffy base that's easy to make. With simple steps and tips for perfecting your cake, you'll impress everyone with this nostalgic dish.
Print Recipe Pin Recipe

Ingredients
  

1 can (20 oz) sliced pineapple in juice, drained

1/4 cup unsalted butter (½ stick)

1/2 cup packed brown sugar

10 maraschino cherries (optional)

1 1/2 cups all-purpose flour

1 cup granulated sugar

1/2 cup unsalted butter, softened

2 large eggs

1 teaspoon vanilla extract

1/2 cup whole milk

1 1/2 teaspoons baking powder

1/4 teaspoon salt

Instructions
 

Preheat the oven to 350°F (175°C). Grease a 9-inch round cake pan with butter.

    In a small saucepan, melt 1/4 cup of butter over medium heat. Add the brown sugar and stir until it forms a smooth caramel. Pour the mixture into the bottom of the prepared cake pan, spreading it evenly.

      Arrange the pineapple slices on top of the caramel and place a maraschino cherry in the center of each pineapple slice (if using). Set aside.

        In a large mixing bowl, cream the softened butter and granulated sugar together until light and fluffy, about 3-4 minutes.

          Add the eggs one at a time, beating well after each addition. Stir in the vanilla extract.

            In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the butter mixture, alternating with the milk, starting and ending with the flour mixture. Mix until just combined.

              Pour the batter over the arranged pineapple slices, spreading it evenly with a spatula.

                Bake in the preheated oven for 35-40 minutes or until a toothpick inserted into the center comes out clean.

                  Allow the cake to cool in the pan for 10 minutes. Then, carefully invert it onto a serving plate, letting the caramel run down over the cake.

                    Let cool slightly before slicing and serving.

                      Prep Time: 20 minutes | Total Time: 1 hour | Servings: 8

                        - Presentation Tips: Dust with powdered sugar and serve with a dollop of whipped cream on the side for an elegant touch.