Pineapple Upside Down Cake

A Pineapple Upside Down Cake is a classic dessert that features a distinctive presentation. The cake is assembled by placing pineapple slices and maraschino cherries in a layer at the bottom of a cake pan in caramelized sugar. A sweet, buttery batter is then poured over the fruit layer. After baking, the cake is flipped upside down onto a serving platter, resulting in a beautiful display where the caramelized fruit becomes the top of the cake. The result is a delicious cake with a caramelized pineapple topping. It’s a timeless dessert that combines the sweetness of caramelized fruit with a moist and flavorful cake.
This dessert is one Chef Brian’s all-time favorites that he forgot all about until becoming a member of his partner’s family. Her Aunt Dawn made a pineapple upside down cake as a dessert for Thanksgiving, and from there it became a necessity at all future family events. Full from dinner or not, there’s always room for Pineapple Upside Down Cake.
To make this Pineapple Upside Down Cake recipe, start by greasing a 10″ cake pan with butter then set aside.
Preheat your oven to 350 degrees Fahrenheit.
Melt 1/2 cups of unsalted butter over, over low heat, in a medium saucepan. Add 3/4 cups of brown sugar to the butter and heat until the brown sugar is melted into the butter. Swirl the pan occasionally until the caramel is an amber color, about 2-3 minutes more. Immediately pour the caramel into the prepared cake pan.
Allow the caramel to cool slightly before arranging the pineapple slices and cherries over top of the caramel. Set the cake pan aside again while preparing the cake batter.
In a mixing bowl, whisk together flour, baking powder, and salt.
Using an electric mixer, beat the butter and remaining sugar together until light and fluffy, this takes about 5 minutes over medium high speed. Start on a low speed until the sugar is incorporated into the sugar, as not to make a mess. Add eggs one at a time, beating well after each addition. Add milk and vanilla, continue to mix in the mixer. Carefully and slowly, add your dry ingredients to the batter and mix until the batter is smooth (about two minutes).
Pour the cake batter over the caramel, cherry, and pineapple in the cake pan. Place the Pineapple Upside Down cake into the oven.
Bake the cake for about one hour or until the cake is golden and it passes the toothpick test. If you don’t know what the toothpick test is, it is putting a toothpick into the center of a cake. If the toothpick comes out clean then the cake is done, if you pull it out and it still has batter on it then it needs more time.
Remove the cake from the oven and place on a cooling rack for at least 30 minutes.
The whole point of Pineapple Upside Down Cake is to invert your cake before slicing and serving it. Carefully invert the cake onto a cake platter then allow the cake to reach room temperature.
Pineapple Upside Down Cake is excellent warm, at room temperature, and cold. It all comes down to preference here.
Enjoy your sweet, moist, dense, flavorful, and classic Pineapple Upside Down Cake!