Classic Pineapple Upside-Down (Printable Version)

A buttery vanilla cake crowned with caramelized pineapple rings and cherries for a stunning golden dessert.

# What You Need:

→ Topping

01 - 1/4 cup unsalted butter
02 - 3/4 cup light brown sugar, packed
03 - 8–10 canned pineapple rings, drained
04 - 8–10 maraschino cherries

→ Cake Batter

05 - 1/2 cup unsalted butter, softened
06 - 1 cup granulated sugar
07 - 2 large eggs
08 - 1 teaspoon vanilla extract
09 - 1 1/2 cups all-purpose flour
10 - 1 1/2 teaspoons baking powder
11 - 1/2 teaspoon salt
12 - 1/2 cup whole milk

# Directions:

01 - Preheat the oven to 350°F (175°C). Grease a 9-inch round cake pan thoroughly.
02 - Melt 1/4 cup butter and pour it evenly into the bottom of the prepared cake pan. Sprinkle the packed light brown sugar over the melted butter.
03 - Place pineapple rings evenly over the sugar mixture. Position a maraschino cherry in the center of each pineapple ring.
04 - In a mixing bowl, beat softened butter and granulated sugar together until the mixture is light and fluffy.
05 - Add the eggs one at a time into the creamed butter and sugar, mixing thoroughly after each addition. Stir in vanilla extract.
06 - Whisk together all-purpose flour, baking powder, and salt in a separate bowl until evenly combined.
07 - Add the flour mixture to the batter in three parts, alternating with the milk. Begin and end with the flour mixture, mixing until just combined after each addition.
08 - Pour and evenly spread the batter over the arranged pineapple and cherries in the pan, smoothing the surface with a spatula.
09 - Bake in the preheated oven for 38 to 42 minutes, or until a toothpick inserted into the center emerges clean.
10 - Allow the cake to cool in the pan for 10 minutes. Run a knife around the edges to loosen, then invert the cake onto a serving plate. Serve warm or at room temperature.

# Expert Advice:

01 -
  • The caramelized topping tastes like candy but happens almost by accident, making you feel like a pastry genius.
  • It's genuinely easy to make but looks impressive enough that people will ask for the recipe.
  • Flipping it over never gets old—every single time feels like a small celebration.
02 -
  • The 10-minute cool-down in the pan is not negotiable—flip it too early and the cake tears, too late and the caramel sticks permanently to the pan.
  • If a pineapple ring slips during the flip, calmly pick it up and set it back in place on the warm cake—the residual heat will make it stick.
03 -
  • If you want to make this ahead, bake the cake the morning of serving and leave it in the pan until an hour before you need it—the caramel stays softer and more beautiful this way.
  • The secret to a cake that doesn't sink in the middle is not overbaking and not opening the oven door before 35 minutes have passed.
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