The Prettiest Pineapple Upside-Down Cake, Ever

Updated March 25, 2017
This spin on traditional pineapple upside-down cake is layered with loveliness and stacked with sweetness. MORE+ LESS-

Pineapple upside-down cake is a classic with rings of pineapples and cherries drenched in caramel and baked underneath a moist yellow cake. Flip it over and, voila! It’s hard to improve on a classic, but that doesn’t mean we can’t try! This pineapple upside-down layer cake is simply two cakes stacked together with whipped cream. It’s still super simple, but all the more irresistible.

For this recipe, you’ll need a box of Betty Crocker yellow cake mix, oil, eggs, canned pineapple rings, maraschino cherries, butter and brown sugar. For the homemade whipped cream, you’ll need heavy whipping cream, sugar and vanilla.


First, heat your oven to 350? and prepare the cake pans. Grease two round 9-inch pans with nonstick spray and then divide the melted butter between the two pans, making sure to cover the entire bottom. Sprinkle the brown sugar over the butter. Add six pineapple rings to each pan and place a maraschino cherry in the center of each ring.


In a large bowl, beat the cake mix, oil, pineapple juice and eggs until batter is smooth.


Pour the cake batter into the prepared cake pans, dividing the batter evenly between the two pans. Use a spatula to smooth out the batter over the pineapple rings. Bake cakes until they’re golden and baked all the way through, about 30 minutes.

Let the cakes cool in the pan for 15 minutes. Then, carefully flip them onto a wire rack to cool completely.


Using a medium bowl, beat the heavy whipping cream, sugar, and vanilla with an electric mixer until thick and soft peaks form. If the cakes seem too fragile to handle, chill in the fridge for 30 minutes to firm up. When you’re ready to assemble the cake, transfer one of the layers to a cake stand or large plate and cover with one cup of the whipping cream mixture.


Place the second cake layer carefully on top. Decorate with swirls of whipped cream, chopped walnuts, and more cherries, or however you desire. Chill in the fridge for 30 minutes, then slice and serve!