Trina’s Pineapple Upside-Down Cake
There are some desserts that never go out of style, and pineapple upside-down cake is one of them. It’s simple, nostalgic, and beautiful without requiring much fuss—which is probably part of the reason it has remained a favorite for so many years.
My version starts with a homemade 1-2-3-4 cake batter, layered over buttery brown sugar, pineapple rings, and cherries. Once it comes out of the oven and you turn it over, all of that goodness becomes a sweet, caramelized topping.
It’s the kind of cake that looks impressive on the table but is surprisingly simple to make. And even better, you probably already have most of what you need in your kitchen!
Trina’s Pineapple Upside-Down Cake
Makes: One 9-inch round cake
Oven: 350°F
Bake Time: Approximately 35–45 minutes
For the Cake
½ cup (1 stick) butter, softened
1 cup sugar
1½ cups cake flour
1½ teaspoons baking powder
¼ teaspoon salt
2 eggs
½ cup milk
½ teaspoon vanilla extract
¼ teaspoon almond extract
For the Pineapple Topping
¼ cup butter
½ cup packed brown sugar
1 can sliced pineapple, drained
Maraschino cherries
Instructions
1. Prepare the pan.
Preheat your oven to 350°F. Place ¼ cup of butter in a 9-inch round cake pan and allow it to melt. You can do this over very low heat if your pan is stovetop-safe, or simply melt the butter separately and pour it into the pan.
Sprinkle the brown sugar evenly over the melted butter.
2. Arrange the pineapple.
Arrange the pineapple slices over the brown sugar mixture in whatever pattern you like. You can leave the rings whole or cut some of them to help fill the pan.
Place a maraschino cherry in the center of each pineapple ring and anywhere else you’d like a little extra color.
3. Make the cake batter.
Cream the softened butter and sugar together until light and fluffy.
In a separate bowl, combine the cake flour, baking powder, and salt.
Add the eggs to the butter mixture and mix well. Gradually add the dry ingredients and milk, alternating between the two, and mix until combined.
Stir in the vanilla and almond extracts.
4. Assemble the cake.
Gently pour the cake batter over the arranged pineapple and cherries, spreading it evenly without disturbing the fruit underneath.
5. Bake.
Bake for approximately 35–45 minutes, or until a toothpick inserted into the center of the cake comes out clean.
6. The best part—flip it!
Remove the cake from the oven and carefully invert it onto a serving plate while it is still warm. Leave the pan over the cake for a few minutes before lifting it away. This gives that buttery brown sugar topping a chance to settle beautifully over the cake.
Serve warm or allow it to cool before slicing.