Description

Homemade Pineapple Upside Down Cake is a classic dessert featuring caramelized pineapple rings and cherries baked beneath a soft, buttery vanilla cake. Once flipped, the glossy brown sugar pineapple topping creates a stunning presentation and delivers rich, nostalgic flavor in every bite.

Ingredients

For the Topping:

¼ cup unsalted butter, melted
½ cup brown sugar
6–8 canned pineapple rings (juice reserved)
6–8 maraschino cherries

For the Cake Batter:

1 ½ cups all-purpose flour
¾ cup granulated sugar
1 ½ teaspoons baking powder
¼ teaspoon salt
½ cup unsalted butter, softened
2 large eggs
½ cup milk (or reserved pineapple juice)
1 teaspoon vanilla extract

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Instructions

Preheat oven to 350°F (175°C). Grease a 9-inch round cake pan.
Pour melted butter evenly into the bottom of the pan. Sprinkle brown sugar evenly over the butter.
Arrange pineapple rings over the brown sugar layer and place a cherry in the center of each ring.
In a medium bowl, whisk together flour, baking powder, and salt.
In a large bowl, cream softened butter and granulated sugar until light and fluffy.
Beat in eggs one at a time, then stir in vanilla extract.
Add dry ingredients alternately with milk (or pineapple juice), mixing just until combined.
Carefully spread batter evenly over the pineapple layer.
Bake for 40–45 minutes, or until a toothpick inserted in the center comes out clean.
Cool in the pan for 10–15 minutes.
Run a knife around the edges and carefully invert the cake onto a serving plate while still warm.

Notes

Flip the cake while warm to prevent sticking.Avoid overmixing to keep the cake tender.Add a splash of rum extract for a tropical twist.A cast iron skillet can be used for even caramelization.